Aldimines and aldimine-containing compositions

FIELD: chemistry.

SUBSTANCE: in formula :

A denotes either an amine residue after removing n primary n aliphatic amino groups and m HX- groups, or together with R7 denotes a (n+2)-valent hydrocarbon residue with 3-20 carbon atoms, which optionally contains at least one heteroatom, particularly in form of oxygen an ether or tertiary amine nitrogen; n equals 1-4, m equals 0-4; under the condition that (m+n) equals 2-5; R1 and R2 either, independently of each other, each denote a univalent hydrocarbon residue with 1-12 carbon atoms, or together denote a divalent hydrocarbon residue with 4-12 carbon atoms, which is part of an optionally substituted carbocycle with 5-8, preferably 6, carbon atoms; R3 denotes a hydrogen atom or an alkyl group or an arylalkyl group or an alkoxycarbonyl group, particularly with 1-12 carbon atoms; X denotes O or S, or N-R6, or N-R7, where values of radicals R4-R6 are given in the claim. The invention also relates to a curable or cured composition containing said compound, use of the compound in adhesives, sealants, filling compounds, coatings and an article containing the curable composition.

EFFECT: higher compound properties.

21 cl, 13 tbl, 48 ex

 

The technical field to which the invention relates.

The present invention relates to the field of aldimines.

The level of technology

Aldimine are condensation products of primary amines and aldehydes, and they are already a well-known class of compounds. Upon contact with water aldimine can be either hydrolyzed to the corresponding amines and aldehydes. Based on this particular, they can be used as a protected form amines or aldehydes. So, aldimine use, for example, in polyurethane chemistry, where they serve as activated by the moisture cross-linking agents, the so-called "blocked amines" or "latent hardeners", for one - or two-component containing the isocyanate group of songs.

The advantages of using aldimines as latent hardeners in the case of containing isocyanate groups systems consist in particular in that it is possible to avoid the occurrence of undesirable gas bubbles, since the curing reaction in the case of the blocked amines in contrast to the direct reaction of the isocyanate with moisture - is not emitting carbon dioxide (CO2), and that you can reach higher speeds the curing and/or longer times of "disclosure". The use of aldimines as latent from the of eruditely, in the case of containing the isocyanate group of compositions, however, can also cause problems. In the case of one-component compositions, the storage stability may be severely limited due to the presence of aldimine. Depending on to get aldimine and again emitted from the curing reaction of aldehydes, composition, moreover, can have a very strong smell, which is intolerable in many applications.

In the international application WO 2004/013088 A1 describes odorless polyamidimide derived from primary polyamines and deprived smell of aldehydes. In the international application WO 2007/036571 A1 describes odorless aldimine containing at least one hydroxyl group, mercaptopropyl or secondary amino group, which also receive from deprived smell of aldehydes. These odorless aldehydes in polymer compositions, in particular in polyurethane compositions, can have a strong plasticizing effect, which may be undesirable. Relatively high molecular weight aldehydes, in addition, leads to that obtained from them aldimine as latent hardeners to be used in relatively large quantities, which may make costly their application.

Description of the invention

Objectives the th of the present invention to provide a new aldimines, which can be used as latent curing agents in curable compositions, in particular, in the case of one - or two-component containing the isocyanate group of songs.

Unexpectedly found that this problem can be solved at the expense of aldimine according to claim 1 claims, which have favorable properties. While we are talking about mostly liquid at room temperature, the compounds that barely have aldehydic odor and which is obtained from easily accessible starting compounds according to one method of primary amines and spatial difficult, having at least one tertiary amino group of aliphatic aldehydes. Aldimine have good thermal stability. Their tertiary amino group has a surprisingly low basicity and, under certain conditions, can exhibit catalytic activity in chemical reaction systems.

These aldimine, for example, suitable as latent hardeners in the case of curable compositions, which are reactive towards amines groups such as epoxy groups, anhydrite group and, in particular, isocyanate group. In particular, they are very compatible in polyurethane compositions and have a small plasticizing action.

Another object of the present invention are, on the one hand, aldimine is about 11 claims and on the other hand, contains antiminority compounds indicated in paragraph 15 and paragraph 20 of the claims, which are the products of transformation of aldimines.

The next object of the present invention are curable compositions containing the described aldimine and/or compounds containing antiminority, item 22 and item 23 of the claims.

Finally, the method of receiving aldimines on p.12 of the formula of the invention, the cured composition according to item 30 of the claims and application p and p claims, as well as the product on p formula of the invention are objects of the present invention.

Other aspects of this invention are the object of other independent claims. Particularly preferred forms of the invention are object of the dependent claims.

Ways of carrying out the invention

The object of the present invention are aldimine formula (I):

where

And means or the remainder of an amine after removal of n primary aliphatic amino groups and m NH-groups

or together with R7means (n+2)-valent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen is;

n denotes 1 or 2, or 3, or 4, preferably 1 or 2, and

m denotes 0 or 1, or 2, or 3, or 4,

provided that the sum (m+n) is 2 or 3, or 4, or 5;

R1and R2

or, independently of one another, represent each a monovalent hydrocarbon residue with 1 to 12 carbon atoms,

or together denote divalent hydrocarbon residue with 4 to 12 carbon atoms, which is part replaced, if necessary, carbocycle from 5 to 8, preferably 6, carbon atoms;

R3means a hydrogen atom or alkyl group, or arylalkyl group, or alkoxycarbonyl group, in particular, with 1-12 carbon atoms;

R4and R5

or, independently lrug from each other, represent each a monovalent aliphatic, cycloaliphatic or arylaliphatic residue with 1-20 carbon atoms which does not contain hydroxyl groups and which, if necessary, contains heteroatoms in the form of a simple oxygen ether or tertiary amine nitrogen,

or together denote divalent aliphatic residue with 3 to 20 carbon atoms, which is part replaced, if necessary, a heterocycle with 5 to 8, preferably 6, atoms in the cycle, and this cycle does not contain a hydroxyl group and, together with the nitrogen atom, if necessary, contains other heteroatom the s in the form of a simple oxygen ether or tertiary amine nitrogen;

X is O or S or N-R6or N-R7,

where R6

either means monovalent hydrocarbon residue with 1-20 carbon atoms, which contains, if necessary, at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,

either means the Deputy of the formula (II):

where

p denotes 0 or an integer from 1 to 10000 and

In means (p+1)-valent hydrocarbon residue, which, if necessary, contains a simple oxygen ether, tertiary amine nitrogen, hydroxyl groups, secondary amino groups or mercaptopropyl; and

R7together with a means (n+2)-valent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen.

The dotted line in formulas, according to this document, represent, respectively, the relationship between the Deputy and related to him the remainder of the molecule.

The term "primary amino group" means, according to this document, the amino group in the form of NH2group, which is associated with one organic residue. The term "secondary amino group" means and what infogruppu, in which the nitrogen atom is linked to two organic residues, which can also be a common part of the cycle. The term "tertiary amino group" means an amino group in which the nitrogen atom is linked to three organic residues, and two of these residues can also be a common part of the cycle (=tertiary amine nitrogen).

The term "aliphatic" refers to amine or amino group, where the nitrogen atom is linked exclusively with aliphatic, cycloaliphatic or arylaliphatic remains.

The term "active hydrogen" means, according to this document, the hydrogen atom of hydroxyl group, mercaptopropyl or secondary amino group.

R1and R2in the formula (I) preferably represent each a methyl group.

R3in the formula (I) preferably denotes a hydrogen atom.

R4and R5preferably do not contain tertiary amine nitrogen.

According to one form of realization of aldimines formula (I), the index m denotes 1 or 2, or 3, or 4, preferably 1. Such aldimine, therefore, contain at least one active hydrogen.

Especially preferred aldimine formula (I) with at least one active hydrogen are aldimine formula (Ia):

where

And1does not contain active hydrogen and does not contain the primary is haunted amino group and

either means a divalent hydrocarbon residue with 2 to 20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen,

or together with R9means trivalent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen;

X1means O or S or N-R8or N-R9,

where R8

either means monovalent hydrocarbon residue with 1-20 carbon atoms, which, if necessary, contains at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,

either means the Deputy of the formula (IIa):

where1means divalent, if necessary, oxygen-containing simple ether or tertiary amine nitrogen, a hydrocarbon residue with 2 to 12 carbon atoms; and

R9together with a1means trivalent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of oxygen, the issue is on ether or tertiary amine nitrogen;

and R1, R2, R3, R4and R5have the specified values.

According to another form of realization of aldimines formula (I), the index m denotes zero and the index n represents 2 or 3, or 4. Such aldimine are polyamidimide. Beginning with the prefix "poly" names of substances, such as polyamidimide, polyamine or polyisocyanate according to the present document, means substances which formally contain two or more available in their name the functional groups in the molecule.

Especially preferred aldimine formula (I) with m=0 are aldimine formula (Ib):

where

t represents 2 or 3, preferably 2;

And2means the residue polyamine with t primary amino groups after removal of the t primary amino groups and contains no active hydrogen;

and R1, R2, R3, R4and R5have the specified values.

Aldimine formula (Ib) do not contain active hydrogen.

Aldimine formula (I) are obtained by reacting at least one amine of formula (III) with at least one spatial difficult aliphatic aldehyde ALD of formula (IV):

where

Xandmeans O or S or N-R6aor N-R7,

where R6a

either means the Deputy of the formula (III'):

and m, n, A, B, R1, R2, R3, R4, R5and R have the specified values.

The interaction between the amine of formula (III) and an aldehyde ALD of formula (IV) occurs in the condensation reaction with elimination of water. Such condensation reaction is already known and described, for example, the manual Houben-Weyl, ”Methods der organischen Chemie”, Vol.XI/2, page 73ff. The aldehyde ALD in respect to the primary amine In the amine groups is used in stoichiometric amount or in a stoichiometric excess. Usually such the condensation reaction is carried out in the presence of a solvent, with which the azeotrope is removed formed during the reaction water. To obtain aldimines formula (I), however, preferred is a method for eliminating the use of solvents, and formed during the condensation reaction water is removed from the reaction mixture directly with the help of vacuum. By obtaining without the use of a solvent is unnecessary Stripping of the solvent is carried out after receiving that simplifies the process of obtaining. Tomoreover, aldimine is thus, free of residual solvent, which may cause nuisance odor.

As the amine In a suitable connections, which, together with one or more primary amino groups, have at least one that includes active hydrogen, a reactive group in the form of hydroxyl groups, mercaptopropyl or secondary amino group. Examples of amines with reactive group containing more than one active hydrogen, are:

- aliphatic amines containing more than one secondary amino group and one or more primary amino groups, as N,N'-bis(3-aminopropyl)Ethylenediamine, Triethylenetetramine (THETA), Tetraethylenepentamine (TERA), pentamethylenebis and higher homologues linear polyethylenimine, N,N'-bis(3-aminopropyl)Ethylenediamine, products, obtained by repeated cyanoethylidene or cyanobutane and subsequent hydrogenation of primary di - and polyamines with several primary amino groups as N,N'-bis(3-aminopropyl)Ethylenediamine, N,N'bis(3-aminopropyl)-1,4-diaminobutane, N,N'-bis(3-aminopropyl)-2-methyl-1,5-pentanediamine, N,N'-bis(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine and polyethylenimine different degrees of polymerization (range of molecular weights from 500 g/mol to 1,000,000 g/mol), which, for example, available under the trade name Lupasol® by BASF in the East form or in the form of aqueous solutions, moreover, these polyethylenimine, along with primary and secondary amino groups, also contain tertiary amino groups;

- hydroxyamine containing more than one hydroxyl group and one or more primary amino groups, in particular, derivatives polyalkoxysiloxanes trivalent or more vysokoudoynyh alcohols or polyalkoxysiloxanes polyamines, and amino sugar, such as glucosamine or galactosamine;

- hydroxyproline containing at least one hydroxyl group and at least one secondary amino group obtained by cyanoethylidene or cyanobutane and subsequent hydrogenation hydroxyamino as N-hydroxyethyl-1,2-amandemen, N-hydroxypropyl-1,2-amandemen, N-hydroxyethyl-1,3-propandiamine, N3-hydroxyethyl-1,3-pentanediamine.

As the amine In a suitable, then, polyamine that include two or more primary aliphatic amino group. Examples of amines with more than three primary aliphatic amino groups are polyvinylene or containing primary amino groups of the copolymers, for example copolymers of allylamine and (meth)acrylates.

As Amin particularly suitable are, first, amines B1 of the formula (IIIa):

where

X1Ameans O or S or N-R8aor N-R9,

where R8a

the means for monovalent hydrocarbon residue with 1-20 carbon atoms, which, if necessary, contains at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,

either means the Deputy of the formula (IIIa'):

and1In1and R9have the specified values.

Amines B1 are suitable, in particular, to obtain aldimines formula (Ia).

Examples of the amines B1 are:

connection with one or two primary aliphatic amino groups and one secondary amino group, such as N-methyl-1,2-amandemen, N-ethyl-1,2-amandemen, N-butyl-1,2-amandemen, N-hexyl-1,2-amandemen, N-(2-ethylhexyl)-1,2-amandemen, N-cyclohexyl-1,2-amandemen, 4-aminomethylpyridine, 3-(4-aminobutyl)piperidine, N-(2-amino-ethyl)piperazine, Diethylenetriamine (DETA), bisexualchristian (VNMC), 3-(2-amino-ethyl)aminopropylation; di - and triamine obtained by cyanoethylidene or cyanobutane and subsequent hydrogenation of primary mono - and diamines, such as N-methyl-1,3-propandiamine, N-ethyl-1,3-propandiamine, N-butyl-1,3-propandiamine, N-hexyl-1,3-propandiamine, N-(2-ethylhexyl)-1,3-propandiamine, N-dodecyl-1,3-propandiamine, N-cyclohexyl-1,3-propandiamine, 3-methylamino-1-pentylamine, 3-ethylamino-1-pentylamine, 3-butylamino-1-pentylamine, 3-hexylamino-1-pentiumi is, 3-(2-ethylhexyl)amino-1-pentylamine, 3-dodecylamino-1-pentylamine, 3-cyclohexylamino-1-pentylamine, dipropylenetriamine (DPTA), N3-(3-AMINOPHENYL)-1,3-pentanediamine, N5-(3-aminopropyl)-2-methyl-1,5-pentanediamine, N5-(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine; and fatty diamines, as the N-cocoalkyl-1,3-propandiamine, N-oleyl-1,3-the propandiamine, N-coulcil-1,3-propandiamine, N-tallowalkyl-1,3-propandiamine or N-(C16-22-alkyl)-1,3-propandiamine that, for example, available under the trade name Duomeen® by the company Akzo Nobel; the products of the reactions proceed by Michael aliphatic primary di - or triamino with Acrylonitrile, diesters of maleic acid or fumaric acid diesters tarakanovas acid, esters of acrylic acid and methacrylic acid, inorganic salts of acrylic acid and methacrylic acid and diesters basis of itaconic acid, which interact in a molar ratio of 1:1;

- aliphatic hydroxyamine, as, for example, 2-aminoethanol, 2-methylaminoethanol (= 2-amino-1-propanol), 1-amino-2-propanol, 3-amino-1-propanol, 4-amino-1-butanol, 4-amino-2-butanol, 2-amino-2-methylpropanol, 5-amino-1-pentanol, 6-amino-1-hexanol, 7-amino-1-heptanol, 8-amino-1-octanol, 10-amino-1-decanol, 12-amino-1-dodecanol, 4-(2-amino-ethyl)-2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethylcyclohexanol; containing primary amino derivatives of glycols, such as diethylenglycol is l, dipropyleneglycol, dibutylamino and higher oligomers and polymers of these glycols, for example, 2-(2-aminoethoxy)ethanol, triethylene glycol-monoamin (= 2-(2-(2-aminoethoxy)ethoxy)ethanol), α-(2-hydroxymethylene)-ω-(2-aminomethylated)poly(oxy(methyl-1,2-ethandiyl)); containing one hydroxyl group and one primary amino group derived polyalkoxysiloxanes trivalent or more vysokoudoynyh alcohols; products obtained by a single cyanoethylidene and subsequent hydrogenation of glycols, for example, 3-(2 hydroxyethoxy)Propylamine, 3-(2-(2-hydroxyethoxy)ethoxy)Propylamine and 3-(6-hydroxyhexyloxy)-Propylamine;

- aliphatic mercaptamine, as, for example, 2-aminoethanethiol (group probably facilitates), 3-aminopropanol, 4-amino-1-butanethiol, 6-amino-1-hexanethiol, 8-amino-1-octanethiol, 10-amino-1-decanter, 12-amino-1-dodecanthiol and amenitiesair as 2-amino-2-deoxy-6-thioglucose.

As Amin B1 preferred are N-methyl-1,2-amandemen, N-ethyl-1,2-amandemen, N-cyclohexyl-1,2-amandemen, N-methyl-1,3-propandiamine, N-ethyl-1,3-propandiamine, N-butyl-1,3-propandiamine, N-cyclohexyl-1,3-propandiamine, 4-aminomethylpyridine, 3-(4-aminobutyl)piperidine, DETA, DPTA, BHMT and fatty diamines, as the N-cocoalkyl-1,3-propandiamine, N-oleyl-1,3-propandiamine N-coulcil-1,3-propandiamine and N-tallowalkyl-1,3-propandiamine; products obtained by reaction of the join is in Michael aliphatic primary diamines with diesters of maleic acid and fumaric acid, esters of acrylic acid and methacrylic acid, inorganic salts of acrylic acid and methacrylic acid, preferably with maleic acid diesters, in particular, dimethyl, diethyl, dipropionyl and debutalbum ether maleic acid, and esters of acrylic acid, in particular with methyl ester of acrylic acid, which interact in a molar ratio of 1:1; and aliphatic hydroxy - or mercaptoamines, in which the primary amino group separated from the hydroxyl group or mercaptopropyl chain of at least 5 atoms, or cycle, in particular, 5-amino-1-pentanol, 6-amino-1-hexanol and their higher homologues, 4-(2-amino-ethyl)-2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 2-(2-aminoethoxy)ethanol, triethylene glycol-monoamin and higher oligomers and polymers, 3-(2-hydroxyethoxy)Propylamine, 3-(2-(2-hydroxyethoxy)ethoxy)Propylamine and 3-(6-hydroxyhexyloxy)Propylamine.

As Amin B1 especially preferred are amines which are selected from the group consisting of N-methyl-1,2-academia, N-ethyl-1,2-academia, N-cyclohexyl-1,2-academia, N-methyl-1,3-propandiamine, N-ethyl-1,3-propandiamine, N-butyl-1,3-propandiamine, N-cyclohexyl-1,3-propandiamine, 4-aminomethylpyridine, 3-(4-aminobutyl)piperidine, DETA, DPTA, BHMT, fatty diamines, as the N-cocoalkyl-1,3-propandiamine, N-oleyl-1,3-propanedione is, N-coulcil-1,3-propandiamine and N-tallowalkyl-1,3-propandiamine, 5-amino-1-pentanol, 6-amino-1-hexanol, 4-(2-amino-ethyl)-2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 2-(2-aminoethoxy)ethanol, triethylene glycol-monoamine, 3-(2-hydroxyethoxy)Propylamine, 3-(2-(2-hydroxyethoxy)ethoxy)Propylamine and 3-(6-hydroxyhexyloxy)Propylamine.

As Amin particularly suitable are, secondly, amines B2 of formula (IIIb):

where a2and t have the specified values.

Amines B2 are suitable, in particular, to obtain aldimines formula (Ib).

Examples of amines B2 are:

- aliphatic, cycloaliphatic or arylaliphatic diamines, such as Ethylenediamine, 1,2-propandiamine, 1,3-propandiamine, 2-methyl-1,2-propandiamine, 2,2-dimethyl-1,3-propandiamine, 1,3-butanediamine, 1,4-butanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD), 1,6-hexanediamine, 2,5-dimethyl-1,6-hexanediamine, 2,2,4 - and 2,4,4-trimethylhexamethylenediamine (TMD), 1,7-heptadien, 1,8-octanediamine, 1,9-enantiomer, 1,10-decontamin, 1,11-undecanedioic, 1,12-dodecandioic and methylbis(3-aminopropyl)amine, 1,2-, 1,3 - and 1,4-diaminocyclohexane, bis(4-aminocyclohexane)methane, bis(4-amino-3-methylcyclohexyl)methane, bis(4-amino-3-ethylcyclohexyl)methane, bis(4-amino-3,5-dimethylcyclohexyl)methane, bis(4-amino-3-ethyl-5-methylcyclohex the forces)methane (M-MO), 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (= ISOPHORONEDIAMINE or ACCESSORIES>), 2 - and 4-methyl-1,3-diaminocyclohexane and mixtures thereof, 1,3 - and 1,4-bis(aminomethyl)cyclohexane, 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA), 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, and 1,3 - and 1,4-xylylenediamine;

- containing group of simple aliphatic ether diamines, for example, a simple bis(2-aminoethylamide) ether, 3,6-dioxaoctyl-1,8-diamine, 4,7-dioctadecyl-1,10-diamine, 4,7-dioctadecyl-2,9-diamine, 4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine and higher oligomers of these diamines, bis(3-aminopropyl)polytetrahydrofuran and other polytetrahydrofurans with molecular masses in the range from, for example, 350 to 5200, and polyoxyalkylene. The latter represent a more typical products obtained by aminating polyoxyalkylene and produced, for example, under the name Jeffamine® (firm Huntsman Chemicals), under the name of palifermin (BASF) or under the name PC Amine® (firm Nitroil). Particularly suitable polyoxyalkylene are Jeffamine® D-230, Jeffamine® D-400, Jeffamine® D-2000, Jeffamine®®D-4000, Jeffamine® XTJ-511, Jeffamine® ED-600, Jeffamine® ED-900, Jeffamine® ED-2003, Jeffamine® XTJ-568, Jeffamine® XTJ-569, Jeffamine® XTJ-523, Jeffamine® XTJ-536, Jeffamine® XTJ-542, Jeffamine® XTJ-559; polyetheramine D 230, polyetheramine D 400 and Polief the Ramin D 2000, PC Amine® DA 250, PC Amine® DA 400, PC Amine® DA 650 and PC Amine® DA 2000;

- aliphatic triamine as 4-aminomethyl-1,8-octanediamine, 1,3,5-Tris(aminomethyl)benzene, 1,3,5-Tris(aminomethyl)cyclohexane;

- polyoxyalkylene that more typically are products of the amination of polyoxyalkylene and are produced, for example, under the trade name Jeffamine® (firm Huntsman Chemicals), under the name of palifermin (BASF) or under the name PC Amine® (firm Nitroil), as, for example, Jeffamine® T-403, Jeffamine® T-5000; palifermin T-403, polyetheramine T-5000; and PC Amine® TA 403, PC Amine® TA-5000.

As Amin B2 are preferred polyamine, which is selected from the group consisting of 1,6-diamine, MPMD, DAMP, ACCESSORIES>, TMD, 1,3-xylylenediamine, 1,3-bis(aminomethyl)cyclohexane, bis(4-aminocyclohexane)methane, bis(4-amino-3-methylcyclohexyl)methane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane, 1,2-, 1,3 - and 1,4-diaminocyclohexane, 1,4-diamino-2,2,6-trimethylcyclohexane, 3,6-dioxaoctyl-1,8-diamine, 4,7-dioctadecyl-1,10-diamine, 4-aminomethyl-1,8-octanediamine and polyoxyalkylene with two or three amino groups, in particular, produced under the trade name Jeffamine® type D-230, D-400, D-2000, T-403 and T-5000 firm Huntsman, and similar compounds produced by BASF or Nitroil, as well as mixtures of these polyamines. As Amin B2 especially preferred are the criminal code of the above diamines.

To obtain aldimine formula (I), then, using at least one spatial hindered aliphatic aldehyde ALD of formula (IV):

where R1, R2, R3, R4and R5have the specified values.

Preferably, R1and R2each represent methyl group, and R3preferably means hydrogen atom.

Preferably, R4and R5each independently of one another, denote ethyl, propyl, isopropyl, butyl, 2-ethylhexyl, cyclohexyl or benzyl, or together with inclusion of the nitrogen atom they form a loop, in particular, pyrolidine, piperidinyl, morpholinyl or N-alkylpiperazine cycle, and this cycle, if necessary, replaced. Particularly preferably, R4and R5do not contain tertiary amine nitrogen.

The aldehydes ALD of the formula (IV) are obtained, in particular, as the reaction product of manniche or similar reactions, manniche α-aminoalkylsilane, as it is known from the literature; therefore, they can be called also the bases of manniche. Aldehyde Y1 of the formula (V), aldehyde Y2 of the formula (VI) and secondary aliphatic amine With formula (VII) when interacting with the removal of water with the formation of aldehyde ALD.

where R1, R2, R3, R4and R5the ima is t already specified values.

This interaction can either be achieved by using free reagents Y1, Y2 and according to formula (V), (VI) and (VII), or reagents can be used to partially or fully in derivational form. So, aldehyde Y1, for example, can be used in the form of enolate, in the form of a simple ester enol, in particular, in the form of a simple ester of silylene, or enamine. Aldehyde Y2 can be used, for example, in the form of oligomer in the case of formaldehyde, in particular, in the form of 1,3,5-trioxane or in the form of paraformaldehyde or in the form of a hydrate, polyacetale, acetal, N,O-acetal, aminal or polyamines. Secondary aliphatic amine With finally, you can use, for example, in the form of a salt, in particular, in the form of amine hydrochloride or hydrosulfate amine, or in the form of silylamine. Some reagents can be used in free form, and some of the reagents can be used in derivational form or can only come from derivatizing forms. When using reagents in derivational form aldehyde ALD, under certain conditions, is also formed in derivateservlet the form of, for example, in the form of a salt; in this case, by suitable treatment, it can translate into a free form according to the formula (IV). Depending on the circumstances, may be rational use in such reactions the transformation additionally vspomogatelny substances, such as Lewis acid or catalysts.

Next, the reaction conversion can be done as a one-step reaction, in which case all three reagent can react with each other; or, however, you can choose a sequential manner, first putting together two of the reagent and thus obtained intermediate product, and then subjecting the interaction with the third reagent, and the intermediate product you can select or not to select. As such intermediate products are suitable are, in particular, salts imine, which is produced by the interaction of the aldehyde Y2, free or derivational form, salt of the secondary aliphatic amine With and which can interact with the aldehyde Y1, free or derivational form, obtaining the appropriate salt of the aldehyde ALD of formula (IV). Such a sequential manner may have the advantage of making possible a more mild reaction conditions and at the same time leads to a higher yield of product.

Further, the interaction can be performed using solvents, particularly polar solvents, such as water or alcohols, or the interaction can be performed without use of solvents.

According to the preferred form done by the means, the interaction is carried out with the use of all reagents in a free form in the form of a single-stage reaction and the aldehyde ALD carried out after interaction purified by distillation. However, preferably do not use organic solvents.

As aldehyde Y1 of the formula (V) are suitable, for example, the following aldehydes: Isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, 2-methylvaleraldehyde, 2-ethylcaproic aldehyde, cyclopentanecarboxaldehyde, cyclohexanecarboxaldehyde, 1,2,3,6-tetrahydrobenzaldehyde, 2-methyl-3-phenylpropionic aldehyde, 2-phenylpropionic aldehyde and diphenylacetaldehyde. It is preferable to Isobutyraldehyde.

As aldehyde Y2 of the formula (VI) are suitable, for example, the following aldehydes: formaldehyde, acetaldehyde, propionic aldehyde, Butyraldehyde, Isobutyraldehyde, phenylacetaldehyde, benzaldehyde and substituted benzaldehyde, as well as esters of Glyoxylic acid, in particular, ethyl ester of Glyoxylic acid. Preferred is formaldehyde.

As an amine With formula (VII) are suitable, for example, the following secondary aliphatic amines include dimethylamine, diethylamine, dipropylamine, Diisopropylamine, dibutylamine, diisobutylamine, di-sec-butylamine, digoxigenin, di(2-ethylhexyl)amine, dicyclohexylamine, N-METI is butylamine, N-ethylbutylamine, N-methylcyclohexylamine, N-ethylcyclohexylamine, di-2-methoxyethylamine, pyrrolidine, piperidine, N-methylbenzylamine, N-isopropylbenzylamine, N-tert-butylbenzylamine, dibenzylamine, morpholine, 2,6-dimethylmorpholine, bis(3-dimethylaminopropyl)amine, N-methyl - or N-ethylpiperazin.

As Amin preferred are dimethylamine, diethylamine, Diisopropylamine, dibutylamine, diisobutylamine, N-methylcyclohexylamine, N-methylbenzylamine, N-isopropylbenzylamine, N-tert-butylbenzylamine, dibenzylamine, pyrrolidine, piperidine, morpholine and 2,6-dimethylmorpholine.

Preferably, the aldehyde ALD is obtained by interaction of Isobutyraldehyde as aldehyde Y1 of the formula (V), formaldehyde as the aldehyde Y2 of the formula (VI) and one of the amines selected from the group consisting of dimethylamine, diethylamine, Diisopropylamine, dibutylamine, diisobutylamine, N-methylcyclohexylamine, N-methylbenzylamine, N-isopropylbenzylamine, N-tert-butylbenzylamine, dibenzylamine, pyrrolidine, piperidine, research and 2,6-dimethylmorpholine, as an amine With formula (VII).

Preferred aldehydes ALD are 2,2-dimethyl-3-dimethylaminopropanol, 2,2-dimethyl-3-diethylaminopropyl, 2,2-dimethyl-3-dibutylaminoethanol, 2,2-dimethyl-3-(N-pyrrolidino)propanal, 2,2-dimethyl-3-(N-piperidino)propanal, 2,2-dimethyl-3-(N-morpholino)propanal, 2,dimethyl-3-(N-(2,6-dimethyl)morpholino)propanal, 2,2-dimethyl-3-(N-benzylmethylamine)propanal, 2,2-dimethyl-3-(N-benzylisoquinoline)propanol and 2,2-dimethyl-3-(N-cyclohexylethylamine)propanal. Preferred aldehydes ALD do not contain additional tertiary amine nitrogen, and have a relatively low basicity.

The aldehydes ALD of the formula (IV) have a number of special properties. So, they have good thermal stability, because the carbon atom in α-position to the aldehyde group does not bear a hydrogen atom and therefore it is not possible elimination of the secondary amine in the formation of the alkene. Further, they have unexpectedly good stability against oxidation by air oxygen. Further, their basicity toward the Central, located at position 3 of the tertiary amine nitrogen - unexpectedly clearly lower than expected in the case of aliphatic amines such structures; the value of the PKandmeasured in the case of a conjugate acid aldehyde ALD is a value of about 2 units lower than that of a conjugate acid is used to obtain the aldehyde ALD of the secondary amine C. These unexpected properties are possible associated with intramolecular 1,4-interaction between the amino group and aldehyde group (orbital overlap between the free electron pair of nitrogen and π - or π*-orbital of the carbonyl), as postulate P.Y. Johnson et a. (J. Org. Chem., Vol.40, Nr. 19, 1975; Seiten 2710-2720) on the basis of NMR and UV spectroscopic studies of β-aminoaldehyde.

Finally, aldehydes ALD, also with a relatively low molecular weight, have no or only minor aminopterin smell. This is unexpected for aldehydes property is a slight odor, probably arises, on the one hand, due to the aforementioned intramolecular 1,4-interaction, on the other hand, due to the spatial difficulties aldehyde group, which is a tertiary carbon atom.

Aldimine formula (I), as already described, can be obtained directly from amines and aldehydes ALD.

Aldimine formula (I), who as Deputy X contain the Deputy N-R6you can obtain, if necessary, a slightly different way than described so far. This way of synthesis is that the aldehyde ALD of formula (IV), in the first stage, is subjected to the interaction with two - or trivalent, preferably diatomic, aliphatic primary amines, which have already been described as amine B2, with formation of an intermediate product, which, along with one or two eliminarpremio, contains one or two, preferably one primary amino group. This intermediate product then, in the second stage, turn in aldimine form is s (I), just alkylating a primary amino group. For alkylation using, in particular, compounds with only one activated double bond, which can come in such a reaction, Michael reaction of accession with primary amines; such compounds are hereinafter referred to as a "Michael acceptor".

The interaction of the aldehyde ALD with amine B2, with the formation containing the primary amino group of the intermediate product, occurs in the condensation reaction with elimination of water, as described above in the case of interaction of the aldehyde ALD with an amine of formula (III). The stoichiometry between the aldehyde ALD and amine B2, however, is chosen so that the use of 1 mol of aldehyde ALD of 1 mol amine B2, which contains two primary amino groups, or so that use two moles of aldehyde ALD on one mole of the amine B2, which contains three primary amino groups. The amine B2 with respect to the amino groups is preferably asymmetric. Preferred is a method of obtaining without the use of solvent, and formed during the condensation water is removed from the reaction mixture using a vacuum.

Interaction containing a primary amino group of the intermediate product with a Michael acceptor is carried out, for example, mixing the intermediate product with a stoichiometric or slightly above stehe the metric quantity of a Michael acceptor and heating the mixture at temperatures from 20°C to 110°C until the complete conversion of the intermediate product in algemin formula (I). The conversion preferably occurs without the use of solvents.

As Amin B2, in the case of this receipt, preferred are the diamines in which the primary amino groups separated by a chain of at least 5 atoms, or cycle, in particular, 1,5-diamino-2-methylpentane, 1,6-hexamethylenediamine were, 2,2,4 - and 2,4,4-trimethylhexamethylenediamine and mixtures thereof, 1,10-decontamin, 1,12-dodecandioic, 1,3 - and 1,4-diaminocyclohexane, bis(4-aminocyclohexane)methane, bis(4-amino-3-methylcyclohexyl)methane, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane, 1,3 - and 1,4-bis(aminomethyl)cyclohexane, 2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,3 - and 1,4-xylylenediamine, as well as containing a group of simple aliphatic ether diamines and polyoxyalkylene.

Examples of suitable Michael acceptors are the diesters of maleic or fumaric acid, such as dimethylmaleic, diethylmalonate, dibutylamine, diethylfumarate; diesters tarakanovas acid, such as dimethylcarbonate; esters of acrylic or methacrylic acid such as methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, tetrahydrofuryl(meth)acrylate, isobornyl(meth)acrylate; diesters Iacono the th acid, such as dimethylethanol; esters of cinnamic acid, such as methylcinnamic; diesters vinylphosphonic acid, such as dimethyl ether vinylphosphonic acid; esters of vinylsulfonate, in particular, arrowie esters of vinylsulfonate; vinylsulfonic; wininit.ini, such as Acrylonitrile, 2-pentenenitrile or fumaronitrile; 1-nitroethylenes, such as β-nitrosothiol; and reaction products of condensation knoevenagel, such as those of diesters of malonic acid and aldehydes, such as formaldehyde, acetaldehyde or benzaldehyde. Preferred are diesters of malonic acid, esters of acrylic acid, diesters of phosphonic acid and wininit.ini.

The implementation of aldimines formula (I)which contain at least one group HX, can be, under certain conditions, in equilibrium with cyclic forms, as indicated in the formula (VIII), for example, for the case with index m=1. These cyclic form, in the case of aminoalkenes, represent a cyclic aminal, for example, imidazolidine or tetrahydropyrimidine; in the case of hydroxyarginine, represent a cyclic aminoacetate, for example, oxazolidine or tetrahydroazepine; in the case of mercaptoethylamine, represent a cyclic thiaminase, for example, thiazolidine or tetrahydrothiophene.

In the formula (VIII) n, A, R1, R2, R3, R4, R5and X have the specified values.

Unexpectedly, in most cases containing NH-groups aldimine formula (I) are not prone to cyclization. In particular, in the case of aminoalkenes, using IR and NMR spectroscopic methods shows that these compounds are predominantly acyclic, therefore, aldimine form, while cyclical, therefore, alinalina form is not found or is found only in trace quantities. Also hydroxy and mercaptoamines, in which the primary amino group separated from the hydroxyl group or mercaptopropyl chain of at least 5 atoms, or cycle, barely take the cyclization.

In the case of aldimines formula (I) refers to new, so far not described compounds with unexpected properties. They contain spatial complicated working antiminority which, if located in the α-position carbon atom does not contain a hydrogen atom and therefore can not tautomerization in inlinegroup. Because of this, these antiminority are especially well protected (locked) primary amino groups, which in excluding moisture show no show no or only minor reactivity with respect to compounds, reacciones the service to the amino groups. Next, aldimine formula (I) contain a tertiary amino group, which, under certain conditions, a chemical reaction systems can exhibit catalytic action; derived from tertiary amino group basicity of aldimines formula (I), however, is unexpectedly low. Next, aldimine formula (I), when a relatively low molecular weight, underlying aldehyde ALD, have no smell or have only minor aminopterin smell.

Aldimine formula (I) possess good thermal stability, because the carbon atom in α-position to alvinegro, as mentioned, does not bear a hydrogen atom and therefore the elimination of the secondary amine in the formation of the alkene is impossible.

Aldimine formula (I) in suitable conditions are stable during storage. When the access of moisture their antiminority through an intermediate stage formally can be either hydrolyzed to amino groups, and emits appropriate, used to obtain aldimines, aldehydes ALD of the formula (IV), which, as already indicated, have very little smell or no smell. Since this hydrolysis reaction is reversible and the chemical balance clearly shifted towards aldimine, we must proceed from the fact that in the absence of reactive towards amines compounds is only part of alvinegro partially or completely hydrolyzed. Unexpectedly, the hydrolysis of alvinegro, despite the presence of tertiary amino groups, can kataliziruetsa acids.

Aldimine formula (I) is obtained from easily accessible starting compounds according to relatively simple way. If when you receive them use flowable amines of the formula (III), the corresponding aldimine formula (I) are partially flowable compounds.

Aldimine formula (I) can be very widely applied. They can be used, for example, wherever they may serve as a source of aldehydes ALD of the formula (IV) or amines of formula (III). In particular, they can be used in functions protected amines, or protected aldehydes in reactive towards aldehydes and/or amines systems and there, if necessary, to purposefully remove the protection. In particular, they find application in systems in which there are compounds that react with primary amines. Remove protectors hydrolytically, for example, by bringing into contact with water or moisture, in particular, with air moisture. Unexpectedly, the hydrolysis of alvinegro, despite the presence of tertiary amino groups may similarly be kataliziruetsa with acids, as in the case of aldimines without tertiary amino groups in the molecule.

On the other hand, aldimine formula (I) is the index m is greater than zero are used in the synthesis of further functionalized with the reaction products of these aldimines. So, aldimine formula (I) with index m is greater than zero can be subjected to interaction with compounds that can react with the NC group, in particular, in the reaction of accession. Suitable compounds which such reactions proceed, include a reactive group, such as, for example, isocyanate group, epoxy group, anhydrite group, or more or less strongly activated double or triple bond such as (meth)acrylate group, acrylamide group, 1-tinykernel group, 1-propionylcarnitine group, maleimide group, citrullinemia groups, vinyl groups, Isopropenyl group or allyl group. Containing antiminority interaction products obtained from these reactions accession, if necessary, can be subjected to hydrolysis to aldehydes ALD of the formula (IV) and compounds with primary amino groups and then used for further reactions, for example for crosslinking reactions, and the hydrolysis reaction can be catalysed using acids.

Next, aldimine formula (I) with index m is greater than zero can be used for containing antiminority compounds which, for example, suitable as latent hardeners or as comonomers for reactive compositions, in particular compositions containing isocyanate the group.

Next, aldimine formula (I) can be used as catalysts for chemical reaction systems, for example, in the case of curable containing isocyanate group of compositions, in particular, to reduce the time of curing.

Finally, aldimine formula (I) can be used as a source of cationic compounds, Protheroe tertiary amino groups are partially or completely to ammonium group or alkylating to Quaternary ammonium groups. By protonation or alkylation of aldimines formula (I) receive aldimine formula (IX):

where

R10means a hydrogen atom or alkyl, cycloalkyl or arylalkyl residue with 1-20 carbon atoms;

X2means O or S or N-R11or N-R7,

where R11

either means monovalent hydrocarbon residue with 1-20 carbon atoms, which contains, if necessary, at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,

either means the Deputy of the formula (IX'):

and m, n, p, A, B, R1, R2, R3, R4and R5and R7have the specified values.

Aldimine formula (IX), then get on the basis of the od of the CSOs from the above amines of formula (III) and an aldehyde ALD of formula (IV), moreover, the tertiary amino group of the aldehyde ALD before interaction with the amine In a partially or fully protonium or alkylate.

For protonation of aldimines formula (I) or aldehydes ALD, you can use any acid Bronsted, as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, carboxylic acids such as acetic acid or benzoic acid, and sulfonic acids, such as methanesulfonate or p-toluensulfonate. For alkylation of aldimines formula (I) or aldehydes ALD can be used known alkylating means, in particular, meteorous means, as, for example, methyliodide, dimethylsulfate, dimethylphosphate, diazomethane, methyl ester ferternal acid or tetrafluoroboric trimethylhexane.

The person skilled in the art it is clear that the composition of the cationic aldimine formula (IX) include the anion, which compensates the positive charge aldimine.

Aldimine formula (I) or formula (IX) are particularly suitable as components of compositions based on isocyanates or epoxy resins, in particular, for use in adhesives, sealants, casting masses, coatings, decking for the floor, paint coatings, varnishes, primers, coatings or foams. Such compositions preferably contain at least one acid, in particular, the organization is organic carboxylic or sulfonic acid, or hydrolyzable to these acid compound, and acid unexpectedly catalyzes the hydrolysis of alvinegro, despite the presence of tertiary amino groups.

Aldimine formula (I) or aldimine formula (IX), in particular, are suitable as hardeners or as precursors of hardeners for one - or two-component containing isocyanate groups, compositions, such as adhesives, sealants, casting masses, coatings, flooring for the floor, coatings, varnishes, primers, coatings or foams.

As already mentioned, aldimine formula (I) contain spatial employed and not able to tautomerizations in inlinegroup antiminority, which are especially well protected (locked) primary amino groups. Together with compounds containing isocyanate groups, aldimine formula (I) with the exclusion of moisture can form stable during storage, that is substantially constant viscosity of the mixture. Particularly stable during storage are mixed with compounds which contain aliphatic isocyanate groups, and/or with compounds that - for example, with phenols contain blocked aromatic isocyanate groups.

The term "aliphatic(cue)" refers to isocyanate group or an isocyanate, when isocyanate is the first group is associated with aliphatic, cycloaliphatic or arylaliphatic balance, in contrast to the aromatic isocyanate or an aromatic isocyanate group, where the isocyanate group is associated with an aromatic residue.

Compositions containing isocyanate groups of the compounds and aldimines formula (I) react in contact with water during the hydrolysis of alvinegro, with the formation of compounds containing urea groups. This isocyanate groups react with primary amino groups, formally released by hydrolysis of alvinegro, and released aldehyde ALD. Excessive in relation to eliminarprem isocyanate groups react directly with moisture and form a urea group. When appropriate stoichiometry between isocyanate groups and eliminarpremio, as a result of these reactions, the composition cures; this process is also called curing. The reaction isocyante groups gidrolizuemye eliminarpremio this does not have to flow through free amino groups. Needless to say, it is also possible reaction with the intermediate stages of hydrolysis. For example, it is possible that gidrolizuacy alvinegro in the form of polyamines directly reacts with the isocyanate group. Suddenly, acid catalyzed hydrolysis alvinegro is not deteriorated due to the presence of tertiary amino groups.

The tertiary amino group of aldimines formula (I) can have a catalytic effect on the reaction of isocyanate groups and can therefore speed up the stitching. This accelerating effect is additionally supported by the fact that the tertiary amino group is localized in the aldehyde part aldimine. However, it is favorable that the basicity of the tertiary amine groups is relatively low, because the strongly basic tertiary amines can excessively accelerate the direct reaction of the isocyanate groups, in particular, with water that may violate impact during curing. During the hydrolysis of alvinegro released aldehydes ALD of the formula (IV)containing a tertiary amino group. On the basis of their relatively small size aldehydes ALD are very mobile in the cured composition, potentially further enhances its catalytic effect on the further isocyanate groups. After done curing, utverzhdenii compositions remain released aldehydes ALD. They are there excellent compatibility, not prone to wypadaniu and have only a slight plasticizing effect, which is often very beneficial.

Aldimine formula (I) can also be stored together with water, provided that aldimine kept separate from the isocyanate groups. Only when the mixture of water and aldimine comes into contact with isocyanate groups, fully hydrolysis proceeds. The reaction between aldimine formula (I) and the isocyanate groups is very slow compared to the reaction of the corresponding primary amines, namely when aldimine store together with water.

You can also use aldimines formula (I) or formula (IX) in the compositions, which otverzhdajutsja under the influence of heat, for example, due to the use of compounds with thermally labile blocked isocyanate groups. Next, you can use aldimines formula (I) or formula (IX) in the compositions, which are reactive or thermosetting hot-melt adhesives. Such adhesives contain molten, in particular, containing isocyanate groups, compounds; they are solid at room temperature and are applied in a warm or hot condition.

Another object of the present invention are containing antiminority connection AV, which represent addition products obtained by reacting at least one aldimine formula (I) with m=1, in particular at least one aldimine formula (Ia), with at least one compound D containing at least one, preferably two reactive groups which can react joining with a group of NC. Group NC Aldini the formulas (I) reacting the reaction of joining with one or more reactive groups of the compound D with the formation containing antiminority AV connection.

If the connection D contains at least two reactive groups, and this interaction is carried out stoichiometrically, i.e. with one mole equivalent of active hydrogen aldimine formula (I) per mol equivalent of the reactive groups of the compounds D - thanks to its reactive group is fully exposed to turning something as containing antiminority connection AV get polyamidimide. So, a simple way to get polyamidimide without needing to obtain the corresponding primary polyamines, which are technically and commercially only partially accessible. Depending on the structure, functionality and molecular weight compounds D and aldimines formula (I) these polyamidimide may have highly different properties; therefore, they can be adapted to the needs of a particular application. These polyamidimide, in particular, suitable as latent hardeners for containing the isocyanate group of songs.

Due to the non-stoichiometric interaction of aldimines formula (I) with compounds D can also be obtained containing antiminority connection AV, which, together with one or more eliminarpremio contain one or more additional available for polyeucte the reactive groups, the so-called heterofunctional compounds AV. Used less than one mole equivalent of active hydrogen aldimine formula (I) per mol equivalent of the reactive groups of the compounds D which contain at least two reactive groups. Connection D itself may be Homo - or heterofunctional. Such heterofunctional compounds AV, for example, applicable as comonomers or latent curing agents for reactive polymer compositions; or, in the case in which heterofunctional AV connection along at least one alvinegro contains at least one reactive group that can react with gidrolizuemye eliminarpremio when connecting molecules, also very applicable as a reactive polymeric composition. This, in particular, relates to a case containing antiminority AV connections, which additionally contain isocyanate groups.

As compounds D suitable substances which contain at least one, preferably more than one, of the following reactive groups that can react accession and which can be selected from the group consisting of isocyanate, isothiocyanate, cyclocarbonate, epoxy, apiculteur, sildenafik, acrylic, methacrylic, 1-tinycorelinux, 1-propionylcarnitine, maleimide, tetracenomycin, vinyl, Isopropenyl and allyl groups. It is also possible that the connection D contains different groups of these above-mentioned reactive groups. Preferred are isocyanate, epoxy, acrylic, maleimide, vinyl, Isopropenyl and allyl groups. Especially preferred are isocyanate groups.

Examples of suitable compounds D are:

two - or polyhydric, mono - and/or oligomeric aliphatic, cycloaliphatic, arylaliphatic and aromatic polyisocyanates such as 1,6-hexamethylenediisocyanate (HDI), 2-methylpentanediol-1,5-diisocyanate, 2,2,4 - and 2,4,4-trimethyl-1,6-hexamethylenediisocyanate (TMDI), 1,12-dodecyltrimethoxysilane, liaindizecign and diisocyanate complex lysine ester, cyclohexane-1,3 - and -1,4-diisocyanate and any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl (=isophorondiisocyanate or IPDI), perhydro-2,4'- and -4,4'-diphenylmethanediisocyanate (HMDI), 1,4-diisocyanato-2,2,6-trimethylcyclohexane (TMCDI), 1,3 - and 1,4-bis(isocyanatomethyl)cyclohexane, m - and p-xylylenediisocyanate (m - and p-XDI), 1,3,5-Tris(isocyanatomethyl)benzene, m - and p-tetramethyl-1,3 - and -1,4-xylylenediisocyanate (m - and p-TMXDI), bis(1-isocyanato-1-methylethyl)naphthalene, α,α,α',α',α"α-HEXAMETHYL-1,3,5-m is silentresident, isocyanates dimeric and trimeric fatty acids such as 3,6-bis(9-isocyanatophenyl)-4,5-di(1-heptenyl)cyclohexane (dimerisation), 2,4 - and 2,6-toluylenediisocyanate and any mixtures of these isomers (TDI), 4,4'-, 2,4'- and 2,2'-diphenylmethanediisocyanate and any mixtures of these isomers (MDI), mixtures of MDI and MDI homologs (polymeric MDI or PMDI), 1,3 - and 1,4-delete the entry, 2,3,5,6-tetramethyl-1,4-diisocyanates, naphthalene-1,5-diisocyanate (NDI), 3,3'-dimethyl-4,4'-diisocyanatobutane (TODI), Tris(4-isocyanatophenyl)methane, Tris(4-isocyanatophenyl)thiophosphate; oligomers of these isocyanates containing uretdione, which is or iminoimidazolidine groups; modified two - or polyhydric isocyanates containing ester, urea, urethane, biuret, allophanate, carbodiimide, uretonimine or oxidization group; and isocyanatobenzene polyurethanes, i.e. containing more than one isocyanate group interaction products of polyisocyanates containing two or more hydroxyl groups of substances (so-called "polyols"), as, for example, two - or polyhydric alcohols, glycols or aminoalcohols, polyhydroxybutyrate polyethers, polyesters, polyacrylates, polycarbonates or paleogeography, in particular, polyethers;

two - or polyhydric epoxides (polyepoxide), t is such as bis(2,3-amoxicillinbuy)ether; polyglycidyl ethers of polyhydric aliphatic and cycloaliphatic alcohols such as 1,4-butanediol, polypropylenglycol and 2,2-bis(4-hydroxycyclohexyl)propane; polyglycidyl ethers of polyhydric phenols, such as resorcinol, bis(4-hydroxyphenyl)methane (bisphenol F), 2,2-bis(4-hydroxyphenyl)propane (bisphenol a), 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, condensation products of phenols with formaldehyde, which are acidic conditions, such as phenomenology and kryzanowski, and these alcohols and phenols, or with polycarboxylic acids, such as dimer fatty acid, or their mixture, pre-elongated simple polyglycidyl esters; complex polyglycidyl esters of polybasic carboxylic acids, such as phthalic acid, terephthalic acid, tetrahydrophtalic acid and hexahydrophthalic acid; N-glycidyloxy derivatives of amines, amides and heterocyclic nitrogen bases, as N,N-diglycidylether, N,N-diglycidylether, N,N,O-triglycidyl-4-aminophenol, N,N,N',N'-tetraglycidyl(4-AMINOPHENYL)methane, triglycerine, tripyridyltriazine;

two - or polyhydric containing acrylic, methacrylic or acrylamide group compounds such as Tris(2-hydroxyethyl)isocyanurate three(meth)acrylate, Tris(2-hydroxyethyl)cyanurate-t and(meth)acrylate, N,N',N"-Tris(meth)acryloylmorpholine; two - or polyhydric acrylates and methacrylates of aliphatic polyethers, polyesters, novolacs, phenols, aliphatic or cycloaliphatic alcohols, glycols and complex polyetiological, and mono - and polyalkoxysiloxanes derivatives of the above compounds, for example, etilenglikoli(meth)acrylate, tetraethyleneglycol(meth)acrylate, tripropyleneglycol(meth)acrylate, polietilenglikoli(meth)acrylate, polypropyleneglycol(meth)acrylate, 1,4-butanediol(meth)acrylate, 1,6-hexanediol(meth)acrylate, neopentylglycol(meth)acrylate, trimethylolpropane(meth)acrylate, pentaerythrityl(meth)acrylate, dipentaerythritol(meth)acrylate, dipentaerythritol(meth)acrylate, dipentaerythritol(meth)acrylate; two or polyhydric acryl - or Methacrylonitrile polybutadienes, polyisoprenes or their block copolymers; adducts of two - or polyhydric epoxides, such as the above-mentioned epoxides with acrylic and methacrylic acid; two - or polyhydric polyurethane(meth)acrylates; two - or polyhydric acrylamide, such as N,N'-methylenebisacrylamide;

two - or polyhydric containing 1-tinykernel or 1-propionylcarnitine group connection;

two - or polyhydric containing maleimide or citrullinemia group compounds such to the to bis - and polybismaleimide from aliphatic, cycloaliphatic or aromatic di - and polyamines and of maleic anhydride or tarakanovas acid, for example, bis(maleimide) α,ω-dimer fatty acid, 4,4'-diphenylmethane(maleimide), 1,3-xylylenebis(citraconic); bis - and polybismaleimide of copolymers of butadiene and Acrylonitrile with terminal amino groups (for example, marketed under the name Hycar® ATBN firm a Noveon) and maleic anhydride or tarakanovas acid; two - or polyhydric adducts of di - and polyisocyanates with N-hydroxyethylamide; esters of two - or polyhydric alcohols and 6 maleimidomethyl acids;

two - or polyhydric containing vinyl and/or isopropylene group compounds such as 1,3 - and 1,4-divinylbenzene, diphenylsulfone, vinylketones, diallyldimethyl, 1,3-diisopropenylbenzene and 1,3,5-triisopropylbenzene, 3-(2-vinyloxyethoxy)styrene, diphenyldimethyl, triphenylethylene, triphenylmethanol, divinyltetramethyldisiloxane, 1,3-divinyl-1,3-diphenyl-1,3-dimethylsiloxane, 1,3-divinyltetramethyldisiloxane, divinyltetramethyldisiloxane, 4-vinyloxycarbonyl, Tris(4-vinyloxyethoxy)vinylsilane; two - or polyhydric simple vinyl and isopropanolamine esters, such as divinely ether, isopropylaniline ether, triethylenemelamine ether, potentiodynamic ether, GE is santiaguinos ether, octadecatrienoic ether, simple divinely ether diol dimer fatty acid and diphenylmethyl; divinelvie esters of dicarboxylic acids, for example, divinely ester of adipic acid;

two - or polyhydric containing allyl groups of compounds such as treelistener, triallylisocyanurate, triethylphosphate; two - or polyhydric simple allyl ethers of alcohols and glycols and their mono - and polyalkoxysiloxanes derivatives, for example, 1,4-bis(allyloxy)butane, 1,6-bis(allyloxy)hexane, triethylenemelamine ether, bisphenol-a-dellroy ether, 3,3'-diallyl-bisphenol-a-dellroy ether, 3,3'-gallivanter, trimethylolpropane ether, glycerinjelly ether, trimethylolpropane ether, pentaerythritoltetranitrate ether; two or polyatomic complex allyl ethers and allylamine carboxylic acids, for example, diallylphthalate, giallelis - and-terephthalate, diallylamine, diallylmalonate, diallylmalonate, diallylphthalate, diallylmalonate; the diatomic allylcarbamate, such as diallylmalonate, di - and dietilenglikoluretan; two - or polyhydric adducts of di - and polyisocyanates with glycidol, allyl alcohol or allylglycine, for example, 1,6-hexamethylenediisocyanate;

- as well as two - or polyhydric heterofunctional, i.e. containing the s, at least two different of the above reactive groups of compounds such as 4-alliancebernstein, 1-alkenylsilanes, such as virilization, propertization and isopropenylbenzene, 2-isocyanatoacetate, 1,2-dimethyl-3-isocyanatopropyl, p-isocyanatomethyl, m - and p-Isopropenyl-α,α-dimethylbenzylidene (m - and p-TMI), m - and p-ethynyl-α,α-dimethylbenzylidene, Isopropenyl-α,α,α',α'-tetramethylethylenediamine, simple glycemically ether, glycidoxypropyl, triglyceridemia, N-(trivinylcyclohexane)maleimide; heterofunctional adducts of di - and polyisocyanates with glycidol, allyl alcohol, allylglycine, N-hydroxyethylamide, hydroxyquinoline acrylates and methacrylates, such as 2-hydroxyethylacrylate and-methacrylate; heterofunctional adducts of mono - and polycarbamide di - and polyisocyanates with acrylic or methacrylic acid; heterofunctional adducts of two or epoxides with a polyhydric acrylic or methacrylic acid, mineralology ether, etilenglikolevye ether, mineralrelated, ethylene glycol(2-allylphenol)vinyl ether, allyl(meth)acrylate, vinylacetate, 2-vinyloxyethyl(meth)acrylate.

As compounds D, in particular, suitable two - or polyhydric alifaticheskii is, cycloaliphatic, arylaliphatic and aromatic isocyanates such as these Monomeric and oligomeric polyisocyanates and containing more than one isocyanate group interaction products of polyisocyanates with polyols, in particular, a simple polyether polyols complex polyether polyols polyacrylonitrile, polycarbonatediol, paleogeographical and mixtures of these polyols.

Depending on the reactive groups of the compounds D and containing active hydrogen group aldimine formula (I), characterized by containing antiminority connection AV reaction accession can be done nucleophile or radical. For reasons of simplicity, the term "reaction accession", in accordance with the present document must also include substitution reactions to the disclosure of the cycle, which, for example, occur in the case of epoxides with nucleophiles, as a result of this, not releasing nucleofug in the form of individual molecules, substitution reactions equivalent to that of the reactions of addition. The reaction accession flows nucleophile when bearing an active hydrogen reactive group aldimine as a nucleophile affects electrophilic reactive group of the compound D, for example, in the case of exposure of an amino group or hydroxyl group on isocyanat the th group. As an example of radical reactions of joining can be called a reaction mercaptopropyl with acrylic group, and for this kind of reaction accession, in General, the required forming radical initiator.

The interaction between aldimines formula (I) and compound (D) to obtain containing antiminority connection AV carried out under known conditions, which are usually used in the case of reactions between the reactive groups involved in the corresponding interaction, for example, at a temperature of 20-100°C. the Interaction is performed with the use of a solvent or, preferably without solvent. If necessary, you can share excipients as, for example, catalysts, initiators or stabilizers. Interaction with isocyanates in the case of aminoalkenes preferably carried out at room temperature without catalyst, in the case of hydroxy-, mercapto - and carbometalation carried out at a temperature of 40-100°C and using a catalyst, which is used in the case of the reaction of Aryanization between isocyanates and alcohols, for example, ORGANOTIN compounds, complexes of bismuth, tertiary amino compounds or combinations of such catalysts.

Received as described, containing antiminority connect the AV mode, such as aldimine formula (I), or almost completely devoid of smell. In suitable conditions, in particular, with the exclusion of moisture, they are stable during storage. Heterofunctional containing antiminority connection AV, which along with eliminarpremio contain additional, available for polyreactive reactive group is stable during storage at a time when they were isolated from causing reaction of these reactive groups of factors, such as, for example, heating or UV radiation.

When the access of moisture antiminority connections AV, containing antiminority, through an intermediate stage formally can be either hydrolyzed to the formation of amino groups, and is released appropriate to be used to obtain aldimine aldehyde ALD of formula (IV), which is also almost or completely devoid of smell. Since this hydrolysis reaction is reversible and the chemical balance clearly shifted towards aldimine, we must proceed from the fact that in the absence of reactive towards amine groups are partially or completely hydrolyzed only part of alvinegro. In the special case heterofunctional containing antiminority AV connections, which contain reactive towards amines, in particular, isocyanate group, gidrolizuacy antiminority react on Rotel, further, for example, with isocyanate groups with the formation of urea groups. In this case, come to the stitching heterofunctional containing antiminority connection AV, which is also without the participation of other substances can lead directly to utverzhdenii polymeric composition. The interaction of reactive towards amines groups gidrolizuemye eliminarpremio this does not have to occur on the amino groups. Of course, also possible interactions with intermediate stages of hydrolysis. For example, it is possible that gidrolizuacy alvinegro in the form of polyacetale directly reacts with reactive towards amines groups.

Containing antiminority AV connection can be used, for example, as a source of cation containing antiminority compounds, Protheroe tertiary amino groups are partially or completely to ammonium group or alkylating to Quaternary ammonium groups.

A preferred form of execution contains antiminority connection AV is containing antiminority compound AV1 of the formula (X):

where

u represents 0 or 1, or 2, or 3, or 4, or 5,

v means 1 or 2 or 3 or 4 or 5 or 6,

provided that the sum (u+v) is 2 or 3, or 4, Il is 5, or 6;

Q means the residue containing (u+v) isocyanate groups MDI after removal of all isocyanate groups;

and1X1, R1, R2, R3, R4and R5have the specified values.

Containing antiminority compound AV1 of the formula (X) are obtained by reacting at least one MDI formula (XI) with at least one containing only one active hydrogen aldimines already formulae (Ia):

In the formula (XI) Q, u and v have the specified values.

Suitable polyisocyanate of the formula (XI), according to one form of execution, is a containing isocyanate groups of the polyurethane polymer PUP.

The term "polymer" includes, according to this document, on the one hand, the combination of chemically uniform, but differ in respect of degree of polymerization, molecular weight and chain length of the macromolecules, which are obtained by polyreactive (polymerization, polyprionidae, polycondensation). The term includes, on the other hand, the derivative of such a set of macromolecules obtained by polyreactive therefore, compounds which are produced by the interaction, such as the reactions of addition or substitution of functional groups of the above macromolecules and to the which may be chemically uniform or chemically non-uniform. The term includes, further, also the so-called prepolymers, that is, reactive oligomeric prepolymers functional groups which participate in the synthesis of macromolecules.

The term "polyurethane polymer" includes all polymers which receive the so-called method diisocyanate polyaddition. It also includes such polymers, which are almost or completely devoid of urethane groups. Examples of polyurethane polymers are simple politicomilitary, complex politicomilitary, simple politicalstability, polycarbamide, complex politicalstability, polyisocyanurate and polycarbamide.

Suitable, containing isocyanate groups of the polyurethane polymer PUP is produced by the interaction of at least one polyol with at least one polyisocyanate.

As polyols to obtain a polyurethane polymer PUP can be used, for example, the following polyols or mixtures thereof:

- simple polyether polyols, also referred to as polyoxyalkylene or oligotherapy, which are polymerization products of ethylene oxide, 1,2-propylene oxide, 1,2 - or 2,3-butilenica, tetrahydrofuran or mixtures thereof, possibly polymerized with the aid of a molecule of initiator, such as water, ammonia, 1,2-ethanediol, 1,2 - and 1,3-propandiol, neopentyl is likely, diethylene glycol, triethylene glycol, the isomeric dipropyleneglycol and dipropyleneglycol, isomeric butandiol, pentandiol, hexandiol, heptanediol, octanediol, nonanediol, decanediol, undemandingly, 1,3 - and 1,4-cyclohexanedimethanol, bisphenol a, hydrogenated bisphenol a, 1,1,1-trimethyloctane, 1,1,1-trimethylolpropane, glycerol, aniline, and mixtures of the above compounds. Can be used as polyoxyalkylene, which have a low degree of unsaturation (determined according to ASTM D-2849-69 and specified in milliequivalent unsaturation per gram of polyol (mEq./g)), we get, for example, using the so-called catalysts based on double metallocyanide complex (DMC catalysts), as well as polyoxyalkylene with a higher degree of unsaturation obtained, for example, with the aid of anionic catalysts such as NaOH, KOH, CsOH or alkali metal alcoholate.

As a simple polyether polyols are particularly suitable polyoxyalkylene and-trioli, in particular, polyoxyalkylene. Especially suitable polyoxyalkylene - and-triolisme are polyoxyethylene - and-trioli and polyoxypropylene - and-trioli.

Particularly suitable are polyoxypropylene and-trioli with the degree of unsaturation lower than 0.02 mEq./g and a molecular weight in the range from 1000 g/mol to 30,000 g/m is al, and polyoxypropylene and-trioli with a molecular weight of from 400 g/mol to 8000 g/mol. The term "molecular weight" or "molecular weight" is always understood, according to this document, the average (srednecenovogo) molecular mass Mn. Particularly suitable are polyoxypropylene with the degree of unsaturation lower than 0.02 mEq./g and a molecular weight in the range from 1000 g/mol to 12000 g/mol, in particular from 1000 g/mol to 8000 g/mol. Such simple polyether polyols are produced, for example, under the trade name Acclaim® by the company Bayer.

Also particularly suitable are the so-called "blocked end EO-groups" (blocked end ethyleneoxide groups) polyoxypropylene and-trioli. The latter are a special Polyoxypropylenediamine that, for example, get alkoxylate clean polyoxypropyleneamine after polipropilenovaya with ethylene oxide, and due to this they contain primary hydroxyl groups;

- styrene-Acrylonitrile or Acrylonitrile-methyl methacrylate-grafted simple polyether polyols;

- complex polyether polyols, also referred to as oligoesters obtained by known methods, in particular by polycondensation reaction hydroxycarbonic acids or the reaction of polycondensation of aliphatic and/or the romantic polycarboxylic acids with diatomic or polyatomic alcohols.

In particular, suitable complex polyether polyols, which are obtained from diatomic, triatomic, in particular, diatomic alcohols, such as ethylene glycol, diethylene glycol, propylene glycol, dipropyleneglycol, neopentylglycol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-hexanediol, 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,12-hydroxystearates alcohol, 1,4-cyclohexanedimethanol, diol dimer fatty acid (dimetyl), neopentylglycol ether hydroxypivalic acid, glycerol, 1,1,1-trimethylolpropane or mixtures of the aforementioned alcohols, with organic di - or tricarboxylic acids, in particular dicarboxylic acids or their anhydrides or esters, such as, for example, succinic acid, glutaric acid, adipic acid, trimethyladipic acid, cork acid, azelaic acid, sabotinova acid, dodecadienol acid, maleic acid, fumaric acid, dimer fatty acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, dimethyl terephthalate, hexahydrophthalic acid, trimellitate acid and anhydride trimellitic acid or mixtures of the aforementioned acids, and also complex polyether polyols from lactones, such as, for example, ε-caprolactone, and initiators, such as the above-mentioned two - or trivalent alcohols.

Especially suitable for complex polyether polyols are complex polyetherdiol;

- polycarbonatediol, which is produced by the interaction of, for example, the above - used for the synthesis of complex polyether polyols - alcohols with diallylmalonate, such as dimethylcarbonate, dellcorporate as diphenylcarbonate, or phosgene.

Particularly suitable are polycarbonatediol;

containing at least two hydroxyl groups, block copolymers that contain at least two different block with the structure of a polyether, a complex of the polyester and/or polycarbonate of the above kind;

- polyacrylate and polymethacrylamide;

- polyhydroxybutyrate fats and oils, for example natural fats and oils, in particular castor oil; or obtained by chemical modification of natural fats and oils, the so - called oleochemical - polyols, for example, obtained by epoxidation of unsaturated oils and subsequent erection cycle with carboxylic acids or alcohols complex epoxypolyester, or simple epoxypolyester, or received by hydroformylation and hydrogenation of unsaturated oils polyols; or derived from natural fats and oils through a process of splitting, such as alcoholysis or ozonolysis and subsequent chemical bonding, for example, by transesterification or dimerization, such the resulting product is impressive cleavage or their derivatives, the polyols. Suitable cleavage products of natural fats and oils are, in particular, fatty acids and fatty alcohols, and fatty acid esters, particularly methyl esters (FAME), which, for example, you can derivateservlet by hydroformylation and hydrogenation with the formation of esters of fatty hydroxyacids;

- paleogeographical, also known as oligohydramnios, as, for example, polyhydroxybutyrate polyolefins, polyisobutylene, polyisoprene; polyhydroxyvalerate copolymers of ethylene and propylene, ethylene and butylene or ethylene, propylene and diene, which, for example, are issued by the company Kraton Polymers; polyhydroxybutyrate polymers of dienes, in particular, 1,3-butadiene, which, in particular, can also be obtained by anionic polymerization; polyhydroxyvalerate copolymers of dienes such as 1,3-butadiene, or mixtures of dienes and vinyl monomers such as styrene, Acrylonitrile, vinyl chloride, vinyl acetate, vinyl alcohol, isobutylene and isoprene, for example, polyhydroxyvalerate copolymers of Acrylonitrile and butadiene, which receive, for example, from copolymers of Acrylonitrile and butadiene with terminal carboxyl groups (commercially available under the name Hycar® CTBN from firm a Noveon) and epoxides or aminoalcohols; and the hydrogenated polyhydroxyphenols the national polymers or copolymers of dienes.

These polyols preferably have an average molecular weight 250-30000 g/mol, in particular 400-20000 g/mol, and preferably have an average HE is a functionality in the range from 1.6 to 3.

In addition to these aforementioned polyols, upon receipt of the polyurethane polymer PUP, you can share a small amount of low molecular weight two - or polyhydric alcohols, such as 1,2-ethanediol, 1,2 - and 1,3-propandiol, neopentylglycol, diethylene glycol, triethylene glycol, the isomeric dipropyleneglycol and dipropyleneglycol, isomeric butandiol, pentandiol, hexandiol, heptanediol, octanediol, nonanediol, decanediol, undemandingly, 1,3 - and 1,4-cyclohexanedimethanol, hydrogenated bisphenol a, dimeric fatty alcohols, such as diols dimeric fatty acid, 1,1,1-trimethyloctane, 1,1,1-trimethylolpropane, glycerin, pentaerythritol, low molecular weight products alkoxysilane the above two - and polyhydric alcohols, and also mixtures of the aforementioned alcohols.

As polyisocyanates to obtain a polyurethane polymer PUP is possible to use aliphatic, cycloaliphatic or aromatic polyisocyanates, in particular diisocyanates, for example, the following:

- Monomeric aliphatic diisocyanates, such as 1,6-hexamethylenediisocyanate (HDI), 2-methylpentanediol-1,5-diisocyanate, 2,2,4 - and 24.4-trimethyl-1,6-hexamethylenediisocyanate (TMDI), 1,10-decamethylenediamine, 1,12-dodecyltrimethoxysilane, liaindizecign and diisocyanate complex lysine ester, cyclohexane-1,3 - and -1,4-diisocyanate and any mixtures of these isomers, 1-methyl-2,4 - and -2,6-diisocyanatohexane and any mixtures of these isomers (HTDI or H6TDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl (=isophorondiisocyanate or IPDI), perhydro-2,4'- and -4,4'-diphenylmethanediisocyanate (HMDI or H12MDI), 1,4-diisocyanato-2,2,6-trimethylcyclohexane (TMCDI), 1,3 - and 1,4-bis(isocyanatomethyl)cyclohexane, m - and p-xylylenediisocyanate (m - and p-XDI), m - and p-tetramethyl-1,3 - and -1,4-xylylenediisocyanate (m - and p-TMXDI), bis(1-isocyanato-1-methylethyl)naphthalene;

- Monomeric aromatic diisocyanates, such as 2,4 - and 2,6-toluylenediisocyanate and any mixtures of these isomers (TDI), 4,4'-, 2,4'- and 2,2'-diphenylmethanediisocyanate and any mixtures of these isomers (MDI), 1,3 - and 1,4-delete the entry, 2,3,5,6-tetramethyl-1,4-diisocyanates, naphthalene-1,5-diisocyanate (NDI), 3,3'-dimethyl-4,4'-diisocyanatobutane (TODI), densityindependent (DADI);

the oligomers and polymers of the aforementioned Monomeric aliphatic or aromatic diisocyanates;

any mixtures of the aforementioned polyisocyanates.

Preferred are Monomeric diisocyanates, in particular, MDI, TDI, HDI and IPDI.

Obtaining a polyurethane polymer PUP carried out in a known manner directly from polisiya is the ATA and polyols or ways gradual accession, also known as reaction extension chain.

According to a preferred form of implementation, the polyurethane polymer PUP get in the reaction, at least one MDI and at least one polyol and isocyanate groups relative to the hydroxyl groups are in stoichiometric excess. The ratio between isocyanate and hydroxyl groups is preferably from 1.3 to 5, in particular from 1.5 to 3.

The interaction is mainly carried out at a temperature at which the used polyols, polyisocyanates and the resulting polyurethane polymer are in a liquid state.

The polyurethane polymer PUP has a molecular weight of preferably above 500 g/mol, in particular, that of from 1000 g/mol to 50000 g/mol, preferably one from 2000 g/mol to 30,000 g/mol.

Further, the polyurethane polymer PUP preferably has an average functionality in the range from 1.8 to 3.

Suitable for interaction with aldimines formula (I) a polyisocyanate of the formula (XI), according to another form of exercise, is a polyisocyanate PI in the form of a Monomeric diisocyanate or an oligomer of Monomeric diisocyanate or a derivative of a Monomeric diisocyanate, and are suitable for this same Monomeric diisocyanates, which are indicated as the e suitable for the production of a polyurethane polymer PUP.

As MDI PI is suitable oligomers or derivatives of Monomeric diisocyanates, in particular, HDI, IPDI, TDI and MDI. Commercially available types are, in particular, HDI-biuret, for example, as Desmodur® N 100 and N 3200 (Bayer), Tolonate® HDB and HDB-LV (Rhodia) and Duranate® 24A-100 (Asahi Kasei); HDI-isocyanurate, for example, as Desmodur® N 3300, N 3600 and N 3790 BA (all from Bayer), Tolonate® HDT, HDT-LV and HDT-LV2 (Rhodia), Duranate® TPA-100 and THA-100 (Asahi Kasei) and Coronate® HX (Nippon Polyurethane); HDI-uretdione, for example, as Desmodur® N 3400 (Bayer); HDI-iminoimidazolidine, for example, as Desmodur® XP 2410 (Bayer); HDI-allophanate, for example, as Desmodur® VP LS 2102 (Bayer); IPDI-isocyanurate, for example, in solution, as Desmodur® Z 4470 (Bayer), or in solid form, as Vestanat® T1890/100 (Degussa); TDI-oligomers, for example, as Desmodur® IL (Bayer)and mixed isocyanurate based on TDI/HDI, for example, as Desmodur® HL (Bayer). Further, particularly suitable are liquid at room temperature, the MDI form (the so-called "modified MDI"), which are mixtures of MDI with MDI derivatives, such as MDI-carbodiimide or MDI-uretonimine, or MDI urethanes, known, for example, under the trade names as Desmodur® CD, Desmodur® PF, Desmodur® PC (all from Bayer), as well as mixtures of MDI and MDI homologs (polymeric MDI or PMDI), manufactured under the trade names as Desmodur® VL, VL50, VL R10, VL R20 and Desmodur® VKS 20F (all from Bayer), Isonate® M 309, Voranate® M 229, Voranate M® 580 (all from Dow) or Lupranat® M 10 R (from BASF).

As MDI PI predpochtitel the s oligomers HDI and/or IPDI, in particular, isocyanurate.

The above oligomeric polyisocyanates PI are usually a mixture of substances with different degrees of oligomerization and/or chemical structures. Preferably, they have an average NCO-functionality of from 2.1 to 4.0 and, in particular, contain, which, iminoimidazolidine, uretdione, urethane, biuret, allophanate, carbodiimide, uretonimine or oxidization group. These oligomers preferably have a low content of Monomeric diisocyanates.

It is also possible that the polyisocyanate of the formula (XI)suitable for interaction with aldimines formula (Ia)represents a mixture consisting of at least one polyurethane polymer PUP and at least one MDI PI.

To obtain a compound AV1 of the formula (X)containing antiminority at least one polyisocyanate of the formula (XI) is subjected to interaction with at least one aldimine formula (Ia). For this fit the above aldimine formula (Ia), respectively, are preferred for this purpose form of execution, which are already described above in detail.

The MDI interaction of formula (XI) with aldimines formula (Ia), to obtain containing antiminority compound AV1 of the formula (X), carried out under conditions which are usually used in the case of the AE reactions between the respective, taking part in the interaction between the reactive groups and which are described above.

If this reaction accession perform stoichiometric, that is, using one mole equivalent of active hydrogen aldimine formula (Ia) one mole equivalent of isocyanate groups MDI formula (XI), due to which these reactive groups are experiencing a complete transformation-as a product of accession get the AV1 connection of the formula (X)containing antiminority, with index u, is equal to zero. This connection AV1 is polyamidimide.

If this reaction accession, on the contrary, carry out non-stoichiometric, that is, using less than one mole equivalent of active hydrogen aldimine formula (Ia) one mole equivalent of isocyanate groups MDI formula (XI), due to which the isocyanate groups are becoming only partially, the product of joining get heterofunctional connection, i.e. containing antiminority compound AV1 of the formula (X), which, along with one or more eliminarpremio still contains at least one isocyanate group. In this case, the index of u in the formula (X) is greater than zero.

Containing antiminority compound AV1 of the formula (X), which is contains isocyanate group - which, consequently, has an index of u in the formula (X) is greater than zero, on the basis of the stability during storage preferably receive, based on MDI formula (XI), which contains only aliphatic isocyanate groups.

Containing antiminority compound AV1 of the formula (X) in appropriate conditions, in particular, with the exclusion of moisture, stable during storage.

In the case of non-stoichiometric interaction of the polyurethane polymer PUP with aldimines formula (Ia), the group HX preferably reacts with commonly available in a polyurethane polymer PUP Monomeric diisocyanates. Thus, reduces the content of Monomeric diisocyanates in polyurethane polymer PUP.

Another preferred form of exercise containing antiminority connection AV is containing antiminority connection AV2 formula (XII):

where

And3does not contain active hydrogen and a primary amino group and

or

means a divalent hydrocarbon residue with 2 to 10 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen,

or

together with R12means trivalent hydrocarbon residue with 3-20 carbon atoms, which is th, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen;

X3means O or S or N-R11or N-R12,

where R12together with a3means trivalent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen;

and Q, u, v, R1, R2, R3, R4, R5, R10and R11have the specified values.

Containing antiminority connection AV2 formula (XII), according to one form of exercise, get on the basis of containing antiminority compound AV1 of the formula (X), which protonium or alkylate. For protonation or alkylation, you can use the same acid Bronsted, or alkylating the funds already described in the case of obtaining aldimines formula (IX).

According to another form of exercise, containing antiminority connection AV2 formula (XII) are obtained on the basis of aldimine formula (IX) with m=1 and n=1, which is subjected to interaction with polyisocyanate already formulae (XI).

A further object of the present invention are curable compositions, referred to in the following context also polyure anonymi compositions which contain at least one polyisocyanate, and either at least one aldimine formula (I) or formula (IX), or, at least, one containing antiminority the AV connection.

The term "polyisocyanate" includes, according to this document, compounds with two or more isocyanate groups, regardless of whether we are talking about a Monomeric diisocyanates, oligomeric-or polyisocyanates containing isocyanate groups of the polymers with relatively high molecular weight.

As aldimine formula (I) are suitable are described in detail above aldimine formula (I), respectively, a preferred form of execution of them, in particular, aldimine formula (Ia) or aldimine formula (Ib). Suitable aldimine formula (IX) as described above. As containing antiminority connection AV suitable are described in detail above, containing antiminority connection AV, respectively, a preferred form of execution of them, in particular, contains antiminority compound AV1 of the formula (X). As containing antiminority connections AV1 particularly suitable such, in which case the index u mean zero, therefore, polyamidimide.

Of aldimines formula (I), further, particularly suitable are those that receive from aldehydes ALD with relatively low basicity is. They, for their part, are products derived from amines With relatively low basicity, such as, in particular, morpholines, and N-alkylbenzenes. Aldehydes ALD with relatively low basicity are, in particular, 2,2-dimethyl-3-(N-morpholino)propanal, 2,2-dimethyl-3-(N-(2,6-dimethyl)morpholino)propanal, 2,2-dimethyl-3-(N-benzylmethylamine)propanol and 2,2-dimethyl-3-(N-benzylisoquinoline)propanal.

Preferred are curable composition containing at least one polyisocyanate and either at least one aldimine formula (I), or, at least, one containing antiminority the AV connection.

According to one form of realization, the curable composition is a single component.

The term "one-component" refers, according to this document, curable composition, in which all component parts of the composition store mixed in the same vessel, and which is stable when stored at room temperature over a longer period of time, therefore, in respect of its property for use or consumption by storing unchanged or only slightly changed, and which cures after application due to exposure to moisture and/or heat.

One-component curable composition comprises at least one polyisocyanate. Its isocyanate groups in the composition may be either in the form of free isocyanate groups or blocked isocyanate groups, or in a mixed form.

Under "blocked isocyanate group," according to this document, see isocyanate group, which due to the preliminary interaction of the free isocyanate groups are known from the prior art locking means, for example, phenol, ketoximes, pyrazole or W malonic acid, so greatly reduced its reactivity towards nucleophiles that it is stable when stored together with suitable hardeners at room temperature and only when exposed to heat and/or moisture begins to react with these hardeners, and a blocking means, depending on the type, is released or not released.

One-component curable composition can be vlagootverzhdaemykh and/or termotorgmash.

Under "termotorgmash composition according to the present document, understand composition with blocked isocyanate groups, which when heated to a suitable temperature, typically in the range from 120°C to 200°C, in special cases, at temperatures ranging from 80°C, isocyanate groups are activated so that with suitable hardeners p is oshodi stitching and thus, the curing. This process is also called thermal drying is usually carried out after application of the composition.

Isocyanate groups MDI-component curable compositions are preferably in the form of free isocyanate groups, in particular, in the form of free aliphatic isocyanate groups.

In one-component curable composition ratio between eliminarpremio and isocyanate groups is, in particular, from 0.1 to 1.1, preferably from 0.3 to 0.9, particularly preferably from 0.4 to 0.8 equivalent of alvinegro to the equivalent of isocyanate groups with isocyanate groups can be either in free or blocked form.

As a one-component curable composition, the preferred one-component vlagootverzhdaemykh composition that includes at least one containing aliphatic isocyanate groups of the polyisocyanate P1 and either at least one aldimine formula (I), or, at least, one containing antiminority the AV connection.

As MDI P1 is suitable, on the one hand, contains aliphatic isocyanate groups of the polyurethane polymer PUP1. Polyurethane polymer PUP1 obtained from polyols and polyisocyanates in the same manner as described above for the polyurethane is of alimera PUP. As polyols suitable already mentioned polyols and polyisocyanates suitable already mentioned aliphatic polyisocyanates, preferably Monomeric aliphatic diisocyanates, in particular, IPDI, HDI, TMDI and HMDI.

As MDI P1 is suitable, on the other hand, the polyisocyanates PI1 in the form of a Monomeric aliphatic diisocyanate or its oligomer, which have already been indicated above, in particular, the oligomer HDI or IPDI.

As MDI P1, then, suitable mixtures containing at least one polyurethane polymer PUP1 and at least one polyisocyanate PI1.

One-component vlagootverzhdaemykh composition, along with at least one polyisocyanate P1 includes, further, or at least one aldimine formula (I), or, at least, one containing antiminority connection AV. As aldimine formula (I) are preferred aldimine formula (Ib) and as containing antiminority connection AV preferred containing antiminority compound AV1 of the formula (X). Containing antiminority compound AV1 of the formula (X) can also be obtained in the composition in situ by adding aldimine formula (Ia) in a suitable non-stoichiometric amount of a composition containing at least one polyisocyanate P1, and the above image is formed steriade is antiminority connection AV1. In this part of the MDI P1 as MDI formula (XI) is embedded in the containing antiminority the AV1 connection.

If necessary, one-component vlagootverzhdaemykh composition contains other components, in particular, commonly used in polyurethane compositions, excipients and additives, for example, the following:

- plasticizers, for example esters of carboxylic acids, such as phthalates, for example, dioctylphthalate, diisononylphthalate or diisodecylphthalate, adipate, for example, dioctyladipate, azelate and Sabatini, organic esters of phosphoric acid and sulfonic acids or polybutene;

- directionspanel thermoplastic polymers, such as Homo - and copolymers of unsaturated monomers, in particular from the group consisting of ethylene, propylene, butylene, isobutylene, isoprene, vinyl acetate and alkyl(meth)acrylates, in particular polyethylene (PE), polypropylene (PP), polyisobutylene, copolymers of ethylene and vinyl acetate (EVA) and atactic poly-α-olefins (ARO);

- solvents;

inorganic and organic fillers, for example, ground or precipitated calcium carbonates, which, if necessary, coated with fatty acids, in particular stearates, barite (BaSO4also called heavy spar), quartz flour, whether kaolin is, aluminum oxide, aluminum hydroxide, silicic acid, in particular, highly dispersed silicic acid pyrolysis processes, carbon black, in particular, industrial produced soot (in the following context referred to as "soot"), polyvinylchloride (PVC powders or hollow beads;

fiber, for example, polyethylene;

- pigments, for example titanium dioxide or iron oxides;

the catalysts which accelerate the hydrolysis of alvinegro, in particular, acids, for example organic carboxylic acids such as benzoic acid, salicylic acid or 2-nitrobenzoic acid, anhydrides of organic acids, such as phthalic anhydride, the anhydride hexahydrophthalic acid and anhydride hexahydromethylphthalic acid, Silovye esters of organic carboxylic acids, organic sulfonic acids, such as methanesulfonate, p-toluensulfonate or 4-dodecylbenzenesulfonate, esters of sulfonic acids, other organic or inorganic acids or mixtures of the aforementioned acids and acid esters;

the catalysts which accelerate the reaction of isocyanate groups, for example, ORGANOTIN compounds such as dibutylaminoethanol, dibutyltindilaurate, dibutyltindilaurate, dibutyltindilaurate and dioctyladipate, bismuth compounds, such as tricoat bismuth and three is(neodecanoate) bismuth, and containing tertiary amino compounds such as simple 2,2'-disorganizational ether and 1,4-diazabicyclo[2.2.2]octane;

- rheology modifiers, such as, for example, thickeners or thixotropic agents, such as urea compounds, polyamide waxes, bentonites or pyrogenic silicic acids;

- reactive diluents and crosslinking agents, for example, Monomeric diisocyanates such as MDI, PMDI, TDI, HDI, 1,12-dodecyltrimethoxysilane, cyclohexane-1,3 - or -1,4-diisocyanate, IPDI, perhydro-2,4'- and -4,4'-diphenylmethanediisocyanate, 1,3 - and 1,4-tetramethylcyclopentadiene, as well as oligomers and derivatives of these polyisocyanates, in particular, in the form of isocyanurates, carbodiimides, uretonimine, Burlov, allophanate or iminoimidazolidine, adducts of Monomeric polyisocyanates with short-chain polyols, and also dehydrated adipic acid and other dihydrazide, as well as the polyisocyanates with blocked aromatic isocyanate groups, such as the types Desmocap® 11, 12, and 2540 XP (all from Bayer), and the types of Trixene® BI 7641, BI 7642, BI 7770, BI 7771, BI 7772, BI 7774 and BI 7779 (all from Baxenden);

- blocked amines, for example, in the form of ketimines, oxazolidines, enamines or other aldimines;

driers, as, for example, molecular sieves, calcium oxide, highly reactive isocyanates such as p-totalization, the esters of orthomorphisms acids is, alkoxysilanes, such as tetraethoxysilane, organoalkoxysilanes, such as VINYLTRIMETHOXYSILANE, and organoalkoxysilanes that in α-position to a silanol group containing a functional group;

-amplifiers adhesion, in particular, organoalkoxysilanes ("silanes"), as, for example, epoxysilane, vinylsilane, (meth)acrylicana, isocyanatobenzene, carbonatation, alkylsilanes, S-(alkylsulphonyl)mercaptoethane and eliminazione, and also oligomeric forms of these silanes;

- stabilizers against heat, light and UV radiation;

- inhibiting ignition of the substance;

- surface-active substances, such as wetting agents that encourage the spreading means, air release tool or antispyware;

- biocides, such as algaecides, fungicides or inhibiting the growth of fungi substances.

When using these other components mainly need to pay attention to the fact that they do not greatly impair the stability of the composition during storage. That is, that these component parts during storage could significantly cause leading to the joining of reactions such as hydrolysis of alvinegro or stitching isocyanate groups. This, in particular, means that all these component parts must not contain water or may contain, at most, trace amounts vodou to be efficient drying of physical or chemical means some parts before the introduction into the composition.

One-component vlagootverzhdaemykh composition preferably contains at least one catalyst. The catalyst, in particular, is one of these acids, such as acid Bronsted or salicylic acid, or one of these metal compounds, or one of these tertiary amines. In addition, it may be preferential use of various catalysts, respectively, different types of catalysts.

One-component lagouvardos composition was prepared and stored with exclusion of moisture. It is stable during storage, i.e. it can be stored with exclusion of moisture, in suitable packaging or a suitable device, such as, for example, a barrel, bucket, package, cartouche or bottle, for a period of time, e.g. several months, without changes, relevant for its use as, in its properties in respect of the application or its properties after curing. Depending on the consistency of the composition, the storage stability, you normally determined by viscosity measurements.

Antiminority aldimine formula (I) and/or containing antiminority connection AV have the ability to either hydrolyzed upon contact with moisture. Formally released the primary amino groups react with the isocyanate composition group the AMI with the formation of urea groups, and released the corresponding aldehyde ALD of formula (IV). Excessive in relation to eliminarprem isocyanate group directly react with moisture and form a urea group. Possibly available blocked isocyanate groups, in General, react upon release of the locking means of the formation of urea groups, and this reaction, under certain conditions, takes place only under the action of heat. As a result of these reactions, the composition solidifies with the formation of solid material; this process is also referred to as curing. The reaction of isocyanate groups with gidrolizuyutza aldimines this does not have to flow through free amino groups. Of course, also possible interactions with intermediate stages of hydrolysis. For example, it is possible that gidrolizuacy alvinegro in the form of polyamines directly reacts with the isocyanate group.

Necessary for the curing reaction water can occur from the air (humidity), or the composition can be brought into contact with water-containing component, for example, by spraying, or to the composition during application, you can add a water-containing component.

One-component vlagootverzhdaemykh composition cures upon contact with moisture, in General, without the formation of the bubble is. On the curing rate can be influenced through the type and quantity of one or more, if necessary, of existing catalysts, through prevailing during curing temperature, as well as through the humidity or the amount of added water.

According to another form of exercise, curable composition is two-component and contains at least one polyisocyanate P2 and either at least one aldimine formula (I), or, at least, one containing antiminority the AV connection.

The term "two-component", according to this document, indicate curable composition in which the component parts of the composition are in the form of two different components, which are stored in separated from other containers and which, accordingly, stable during storage. Both components are denoted as component K1 and a component K2. Only shortly before or during application of the composition both components are mixed with each other, after which the mixed composition is cured, and the curing, under certain conditions, flows, or supplemented only by moisture and/or heat.

Aldimine formula (I) or containing antiminority AV connection can be either an integral part of component K1 or part of the component K2, or part of both components is K1 and K2.

Component K1 two-component polyurethane composition as MDI contains at least one polyisocyanate P2.

As MDI P2 suitable polyisocyanate PI2 in the form of a Monomeric diisocyanate or an oligomer of Monomeric diisocyanate or a derivative of a Monomeric diisocyanate. As MDI PI2 fit the above polyisocyanates PI, and the preferred technical forms oligomeric IPDI, HDI and TDI, and, in particular, PMDI and liquid at room temperature, the MDI form.

As MDI P2, then suitable polyurethane polymer PUP, which is described above.

As MDI P2, finally, also suitable mixture of a polyurethane polymer PUP and polyisocyanates PI2, in particular, a mixture of at least one, based on MDI, polyurethane polymer PUP and at least one Monomeric and/or polymeric MDI.

Along with polyisocyanate P2, component K1 can contain at least one aldimine formula (I) or, at least, one containing antiminority connection AV. In this case, the polyisocyanate P2 preferably contains aliphatic isocyanate groups. Preferably, however, the component K1 does not contain neither aldimine formula (I)or containing antiminority the AV connection.

Component K2 of a two-component polyurethane to the notizie contains, at least one reactive towards isocyanate groups of the component part, in particular selected from the group consisting of water, polyamines, polyols, aminoalcohols, policylaw or blocked amines. Component K2 preferably contains at least one blocked amine in the form of at least one aldimine formula (I) or in the form of at least one containing antiminority connection AV. Suitable for this are described in detail above aldimine formula (I), respectively, and their preferred modes of implementation, in particular, aldimine formula (I) with the sum of the indices (m+n is 2 or 3, containing antiminority connection AV that do not contain isocyanate groups and have the functionality to interact with isocyanate groups, equal to 2 or 3. Especially preferred aldimine formulas (Ia) and (Ib), as well as containing antiminority compound AV1 of the formula (X) with index u=0 and the index v=2 or 3.

As polyamines, in the case of component K2, suitable primary aliphatic polyamine that already described as amines B2 of formula (IIIb); secondary aliphatic polyamine, as, for example, N,N'-dibutylethanolamine, N,N'-di-tert-butylethylenediamine, N,N'-diethyl-1,6-hexanediamine, 1-(1-methylethylamine)-3-(1-methylaminomethyl)-3,5,5-trimethylcyclohexane (Jeffink® 754 is t Huntsman), N4-cyclohexyl-2-methyl-N2-(2-methylpropyl)-2,4-pentanediamine, N,N'-dialkyl-1,3-xylylenediamine, bis(4-(N-alkylamino)cyclohexyl)methane, N-alkylated simple polyetheramines, for example, Jeffamine® SD-231, SD-401 SD-404 SD-2001 (all from Huntsman), the addition products according to Michael mentioned as examples of the primary aliphatic polyamines to Michael acceptors, as the diesters of maleic acid, diesters of fumaric acid diesters tarakanovas acid, esters of acrylic acid, esters of methacrylic acid, esters of cinnamic acid, diesters basis of itaconic acid diesters vinylphosphonic acid, arrowie esters of vinylsulfonate, vinylsulfonic, wininit.ini, 1-nitroethylenes or the reaction products of knoevenagel, for example, those derived from diesters of malonic acid and aldehydes, such as formaldehyde, acetaldehyde or benzaldehyde; aliphatic polyamine with primary and secondary amino groups, such as N-butyl-1,6-hexanediamine; primary and/or secondary aromatic polyamine, as, for example, m - and p-phenylenediamine; 4,4'-diaminodiphenylmethane (MDA), 3,3'-dichloro-4,4'-diaminodiphenylmethane (ILAC), mixtures of 3,5-dimethyldi-2,4 - and -2,6-toluenediamine (available as Ethacure® 300 firm Albemarle), mixtures of 3,5-diethyl-2,4 - and -2,6-toluenediamine (DETDA), 3,3',5,5'-tetraethyl-4,4'-diaminodiphenylmethane (M-DEA), 3,3',5,5'-tetraethyl-2,2'-dichloro-4,4'-diaminodiphenylmethane (M-CDEA), 3,3'-visapro the Il-5,5'-dimethyl-4,4'-diaminodiphenylmethane (M-MIPA.), 3,3',5,5'-tetraisopropyl-4,4'-diaminodiphenylmethane (M-DIPA), 4,4'-diaminodiphenylsulfone (DDS), 4-amino-N-(4-AMINOPHENYL)benzosulfimide, 5,5'-etilendiaminova acid, dimethyl(5,5'-methylenedinitramine), 1,3-propylenebis(4-aminobenzoate), 1,4-butylene(4-aminobenzoate), polytetramethylene(4-aminobenzoate) (available as Versalink® by the company Air Products), 1,2-bis(2-aminophenylthio)ethane, N,N'-dialkyl-p-phenylenediamine, N,N'-dialkyl-4,4'-diaminodiphenylmethane, 2-methylpropyl(4-chloro-3,5-diaminobenzoate) and tert-butyl(4-chloro-3,5-diaminobenzoate); and polyamine with more than three amino groups.

As polyols in component K2 fit the same polyols that are already listed as suitable for the production of a polyurethane polymer PUP, as well as the same low molecular weight two - or polyhydric alcohols listed above as suitable for joint use in obtaining a polyurethane polymer PUP.

As aminoalcohols in the case of component K2 is suitable compounds which contain at least one primary or secondary amino group and at least one hydroxyl group, such as aliphatic hydroxyamine, already mentioned above as suitable amines B1 to obtain aldimines formula (I), and, further, for example, diethanolamine, 2-(methylamino)ethanol, 2-(ethylamino)ethanol, 2-(butylamino)ETANA and 2-(cyclohexylamino)ethanol.

As policylaw in the case of component K2 is suitable, for example, known under the trade name Thiokol® liquid polymers with integral mercaptopropanol, for example, LP-3, LP-33 LP-980, LP-23 LP-55 LP-56 LP-12, LP-31, LP-32 LP-2 (Morton Thiokol; for example, manufactured by SPI Supplies, USA, or by the company Toray Fine Chemicals, Japan), and polyesters thiocarbonic acids, for example, pentaerythritoltetranitrate, trimethylpentanediol, glycolipoprotein, pentaerythrityl(3-mercaptopropionate), trimethylolpropane(3-mercaptopropionate), glycolide(3-mercaptopropionate).

Along with aldimine formula (I) and containing antiminority AV connections, you can also use other blocked amines as an integral part of the component K2, in particular, catimini, oxazolidines, enamines, and other aldimine. Such other aldimine receive from other aldehydes than the above-mentioned aldehydes ALD of the formula (IV), as, for example, Isobutyraldehyde or the reaction products of the esterification of carboxylic acids, such as lauric acid, 3-hydroxybenzaldehyde. Catimini, for example, is produced by the interaction of the above amines of formula (III) with ketones. Suitable oxazolidinone are, in particular, polyoxazolines, as, for example, the hardener OZ (Bayer). Suitable enamines receive, for example, by in the aimogasta amines with multiple secondary amino groups and aliphatic or cycloaliphatic aldehydes or ketones, which the carbon atom in α-position to a carbonyl group include, for example, one atom of hydrogen.

If necessary, the component K2 contains water, in particular, is necessary for hydrolysis of alvinegro and other blocked amino groups, the amount of water or part thereof.

Component K2, further preferably contains at least one catalyst in the form of ORGANOMETALLIC compounds and/or tertiary amine and/or acids, especially organic carboxylic or sulfonic acid.

Two-component polyurethane composition contains, if necessary, other components. In the case of component K1 is, in particular, auxiliary substances and additives described above for single-label vlagootverzhdaemykh composition. In the case of component K2, along with them, optionally other auxiliary substances and additives that are unable or only briefly able to be kept together with the free isocyanate groups. In particular, these catalysts, such as:

compounds of zinc, manganese, iron, chromium, cobalt, copper, Nickel, molybdenum, lead, cadmium, mercury, antimony, vanadium, titanium, zirconium, or potassium, such as zinc acetate(II)2-ethylhexanoate zinc(II)laurate zinc(II), oleate of zinc(II)naphthenate, zinc(II)acetylacetonate, zinc(II), salicylate zinc(II), 2-who telekanal manganese(II), 2-ethylhexanoate iron(III)acetylacetonate iron(III)2-ethylhexanoate chromium(III)naphthenate, cobalt(II)2-ethylhexanoate, cobalt(II)2-ethylhexanoate, copper(II)naphthenate, Nickel(II), neodecanoate finalstate, acetate of lead(II)2-ethylhexanoate, lead(II), neodecanoate of lead(II)acetylacetonate, lead(II), aluminum lactate, aluminum oleate, aluminum acetylacetonate(III), diisopropoxide(ethylacetoacetate), dialogsettings(ethylacetoacetate)dialogsettings(acetylacetonate), potassium acetate, octoate potassium; tertiary amines such as triethylamine, tributylamine, N-ethyldiethanolamine, N,N,N',N'-tetramethylethylenediamine, pentamethyldiethylenetriamine and their higher homologues, N,N,N',N'-tetramethylpropylenediamine, pentamethyldiethylenetriamine and their higher homologues, N,N,N',N'-tetramethyl-1,3-butanediamine, N,N,N',N'-tetramethyl-1,6-hexanediamine, bis(dimethylamino)methane, N N-dimethylbenzylamine, N,N-dimethylcyclohexylamine, N-methyldicyclohexylamine, N,N-dimethylhexylamine, bis(N,N-dimethylaminoethyl)adipate, N,N-dimethyl-2-phenylethylamine, Tris(3-dimethylaminopropyl)amine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), N-methylmorpholine, N-ethylmorpholine, N-commonfolk, N,N'-dimethylpiperazine, N-methyl-N'-dimethylaminomethylphenol, bis(dimethylaminoethyl)piperazine, 1,3,5-Tris(dimethylaminopropyl)hexahydrotriazine, bis(2-dimethylaminoethyl is new)ether; nitrogen-containing aromatic compounds such as 4-dimethylaminopyridine, N-Mei, N-vinylimidazole or 1,2-dimethylimidazole; amidine and guanidine, such as 1,1,3,3-tetramethylguanidine; tertiary amines containing active hydrogen atoms, such as triethanolamine, triisopropanolamine, N-methyldiethanolamine, N,N-dimethylethanolamine, 3-(dimethylamino)propertiesproperty, bis(3-(dimethylamino)propyl)isopropanolamine, bis(3-dimethylaminopropyl)amine, 3-(dimethylamino)propylboronic, Mannich bases of phenols, such as 2,4,6-Tris(dimethylaminomethyl)phenol or 2,4,6-Tris(3-(dimethylamino)propylaminoethyl)phenol, imidazoles, such as N-hydroxypropylamino or N-(3-aminopropyl)imidazole, as well as products alkoxysilane and polyalkoxysiloxanes of these compounds, for example, dimethylaminoethoxide; organic ammonium compounds such as the chloride designed or alkoxysilane tertiary amines; the so-called catalysts "delayed action", which are modifications of known catalysts based on metals or amines, such as the interaction products of tertiary amines and carboxylic acids or phenols, for example, 1,4-diazabicyclo[2.2.2]octane or DBU and formic acid or acetic acid; and combinations of these compounds, in particular compounds of metals and Tr is part of amines.

Getting the two components K1 and K2 are carried out separately from each other, in the case of component K1 with the exclusion of moisture. The two components K1 and K2 separately from each other stable during storage, that is, they, each, in suitable packaging or device, such as, for example, a barrel, bucket, package, cartouche or bottle before use can be stored for several months up to a year and longer, without modification, in the relevant paraphernalia least in respect to their respective properties.

To apply two-component polyurethane compositions of the two components K1 and K2 are mixed with each other. This should draw attention to the fact that the mixing ratio is chosen so that reactive towards isocyanate groups of the compound housed in a suitable ratio to the isocyanate groups of component K1. In particular, the ratio is from 0.1 to 1.1, preferably from 0.5 to 0.95, particularly preferably from 0.6 to 0.9 equivalent amount of available hydroxyl groups, amino groups, mercaptopropyl and protected amino groups per equivalent of isocyanate groups, protected amino groups in the form oxazolidinone groups are calculated twice. During curing of excess isocyanate groups react with moisture, in particular, with air moisture.

Pach is the W the two components K1 and K2 are carried out using a suitable method, for example, in a static mixer. Mixing can be performed continuously or periodically. The mixed composition is then applied to the substrate, if necessary, using a suitable means for applying. Thus it is necessary to pay attention to the fact that between the mixing components and the application was not too much time, because too strong a preliminary response component parts of the mixed composition before application may be degraded function utverzhdenii composition, for example, the fact that the adhesion to the substrate is obtained only unsatisfactory or delayed. The maximum period of time during which it should be applied to the mixed composition, called the "viability".

After mixing of the components K1 and K2 starts curing. Antiminority start already described to react with isocyanate groups, as soon as they come into contact with water. Water is either already present in the mixed composition as it is an integral part of the component K2 or because it is added to the mixture before or during the mixing of the two components K1 and K2-or water diffuses in the form of moisture air in the mixed composition. In the latter case, the specified reaction alvinegro with isocyanate groups flows from outside to inside, parallel is topline moisture from the air into the composition. As already mentioned, the reaction of isocyanate groups with gidrolizuemye eliminarpremio does not have to occur on free amino groups, and may also pass through an intermediate stage of hydrolysis. Similarly released reactive group other possibly present in the composition, blocked amines. Next, after mixing of the components K1 and K2, are contained in the composition of a hydroxyl group, mercaptopropyl and amino groups interact with the isocyanate groups. Excess isocyanate groups, in particular, react directly with water. As a result of these reactions mixed composition is subjected to the stitching and finally solidifies with the formation of solid material.

Curing described curable compositions is, in General, without the formation of bubbles at high speed curing. On the curing rate can be influenced by the type and amount of one or more, if necessary, present catalysts, predominant during curing temperature, and humidity or the amount of added water.

As mentioned above, the tertiary amino group of aldimines formula (I), or containing antiminority AV connections, can have a catalytic effect on the reaction of the isocyanate g is PP and therefore to accelerate the curing. Thus favorably to its basicity was relatively low, because the strongly basic tertiary amines worsen acid catalyzed hydrolysis of alvinegro and/or excessively can accelerate the direct reaction of the isocyanate groups, in particular, with water that can adversely affect the curing. The accelerating effect of the tertiary amine groups in the reaction of the isocyanate groups, in particular, on the response remaining after the reaction of alvinegro isocyanate groups available water, additionally supported by the fact that the tertiary amino group is localized in the aldehyde part aldimine. During the hydrolysis of alvinegro released aldehydes ALD of the formula (IV)containing a tertiary amino group. On the basis of their relatively small size, aldehydes ALD are very flexible in the cured composition, which potentially increases their catalytic effect on further isocyanate groups. Released aldehydes ALD remain, then, in utverzhdenii compositions shown in her excellent compatibility, not prone to wypadaniu and have only a slight plasticizing effect, which is often very beneficial. A further advantage of the described compositions is relatively slight smell of these aldimines and released at about the approved aldehydes ALD. Due to this composition before, during, and after curing, have only a slight odor.

As a result of these reactions with water, in particular, in the form of atmospheric humidity, the composition is subjected to the stitching and finally solidifies with the formation of solid material.

Preferred applications described curable compositions are one - or two-component adhesives, sealants, casting masses, coatings, flooring for the floor, coatings, varnishes, primers, coatings or foams. Separate applications must be briefly described, which, however, was in no way intended to limit other uses of these compositions.

According to one preferred form of implementation described curable compositions are used as elastic adhesives or sealants. In the case of this use, the content of MDI, preferably in the form containing isocyanate groups of the polyurethane polymer is a value in the range, in particular, 10-80 wt.%, preferably 15-70 wt.%, in terms of the whole composition.

Further, the curable composition, when used as an elastic adhesive or sealant, mainly contains at least one filler, and it has an effect on the rheological properties neo is approved composition, and also on the mechanical properties and surface quality utverzhdenii composition. Suitable fillers are already mentioned inorganic and organic fillers. Preferred are carbon black, calcium carbonates, whether kaolin, highly dispersed silicic acid, polyvinylchloride powders, as well as inhibiting inflammation fillers such as hydrates and hydroxides, in particular, the aluminum hydroxide. The content of the filler is a value in the range, in particular, 10-70 wt.%, preferably 20-60 wt.%, in terms of the whole composition. The advantage may be the use of a mixture of different fillers.

Further, the curable composition, when used as an elastic adhesive or sealant, mainly contains at least one of the previously mentioned catalysts which accelerate the hydrolysis of alvinegro, respectively, the reaction of the isocyanate groups. Particularly suitable are mixtures of organic acids and ORGANOMETALLIC compound or complex of a metal from an organic acid containing a tertiary amino compounds, or a mixture of organic acids, ORGANOMETALLIC compounds or complex metal containing tertiary amino compounds. Typical content of the catalyst generally ranges from 0.005 to 2 the ACC.%, in terms of the whole composition, and professional clear what the quantities used and for which catalysts are rational.

Elastic adhesive or sealant may be in the form of one-component or two-component compositions, and, accordingly, prepare and put the already described manner. One-component elastic adhesive or sealant preferably contains at least one polyurethane polymer PUP1.

Suitable uses one - or two-component elastic adhesive are, for example, bonding of structural elements in case of construction of surface and underground facilities and in the manufacture or repair of industrial products or consumer goods, in particular, Windows, appliances or vehicles, such as water and land vehicles, preferably automobiles, buses, trucks, trains, or ships, as well as bonding products, furniture, textile or packaging industry; or sealing of joints, seams or cavities in industrial manufacture or repair, or in the case of the above-ground or underground structures.

Suitable uses one - or two-component elastic sealant are, for example, sealing structure, in particular, the joints in the case is stroitelstva ground or underground structures, or sealing parts of a design, for example, Windows or flooring, or sealing industrial product, such as, for example, household machines or vehicles, in particular, water or land vehicle or its parts.

According to a further preferred form of implementation, one of the described curable compositions are used as the elastic coating. In the case of this application, the contents of the MDI is a value in the range, in particular, 10-80 wt.%, preferably 15-70 wt.%, in terms of the whole composition.

Further, the curable composition, when used as the elastic coating contains mainly of at least one filler, and the filler has an effect on the rheological properties of the uncured composition and also on the mechanical properties and surface quality utverzhdenii composition. Suitable are the inorganic and organic fillers. The preferred calcium carbonates, barite and quartz flour, as well as inhibiting inflammation fillers such as hydrates or hydroxides, in particular, the aluminum hydroxide. The content of the filler is a value in the range, in particular, 10-70 wt.%, preferably 20-60 wt.%, in terms of the whole composition. The advantage of mo is et to be the use of a mixture of different fillers.

Further, the curable composition, when used as the elastic coating mainly contains at least one catalyst. While suitable such catalysts and in the same quantities that are already listed as suitable parts of elastic adhesives and sealants.

Further, the curable composition, when used as the elastic coating mainly contains at least one other component from the already mentioned auxiliary substances and additives, in particular selected from the group consisting of pigments, contributing to the spreading means, antispyware and stabilizers.

Elastic coating may be in the form of one-component or two-component compositions, and it is prepared and applied, respectively, already described.

Composition mainly has a liquid consistency with good properties in respect to spreading. Due to this, it can be applied just as samarasekera coating on mostly flat surfaces, such as flooring.

If the finished floor, it is often about the structure of several distinct layers. A typical structure may begin, for example, with the so-called primers, which task is to prepare the basics of DL is elastic polyurethane coating. Then applied, for example, the specified composition in the form of an elastic layer, and this application can be implemented as one or more process operations depending on the quality framework and the desired thickness of the layer. Usually put a layer thickness of from 0.5 mm to 3 mm, in particular from 0.5 mm to 2 mm per coat. Finally, after that you can apply the so-called seal, which in a thin layer, for example, with a thickness from several micrometers up to several tenths of millimeters, again influences the surface quality of the flooring. It can be transparent or pigmented seal.

In the case of two-component coatings, the two components K1 and K2 before applying appropriately mixed with each other and the mixed composition is applied within its viability.

The application of the curable compositions in the form of the elastic coating is usually carried out by pouring on a covered basis and in a liquid state evenly distribute by means of, for example, squeegee or notched fittings for drip impregnation. The material can be further align and deaerate with needle roller. However, it is also possible mechanical drawing, for example, in the form of a spray application.

Suitable basis on which put is typically a composition is, for example, the R, concrete, cement, asphalt, steel, wood, ceramic or plastic, and the base may be pre-processed by cleaning, cleaning with a brush or by sandblasting, and/or may have a primer. As the primers used, for example, solutions of amplifiers adhesion or primer coating.

Described elastic coating can preferably be used for indoor or outdoor area of a structure or structures, such as flooring in interior spaces such as offices, industrial workshops, gymnasiums or the refrigerating chamber, or in the outdoor area of balconies, terraces, bridges, car parks or sports grounds and playgrounds.

According to the following preferred form of implementation, one of the described curable compositions are used as coatings, varnish or primer coating. In the case of this application, the polyisocyanate preferably represents either the polyisocyanate PI1, or the polyisocyanate PI2.

The term "ground floor", according to this document, see suitable as a pre-paint coating composition, which, along with directionspanel volatile substances and optional solid additives, contains at least one polymer and/the Lee, at least one substance with reactive groups and which when applied to a substrate capable of curing with the formation of a strong, well-adherent film with a thickness of typically at least 5 μm, and curing is carried out either by evaporation directionspublic volatile substances, such as solvents or water, or by chemical reaction, or by a combination of these factors, and which provides good adhesion for the next applied layer, for example, adhesive or sealant.

When used as a varnish, lacquer or primer coating is the preferred one-component compositions, and for reasons of stability during storage, they preferably contain only polyisocyanates with aliphatic isocyanate groups.

Further, the curable composition, when used as a varnish, lacquer or primer coating, mainly contains at least one other component from the already mentioned auxiliary substances and additives, in particular, at least one solvent. Suitable solvents are, for example, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyrate and mesityloxide, and cyclic ketones, such as cyclohex is anon and methylcyclohexane; esters such as methyl acetate, ethyl acetate, propyl, butyl acetate, tert-butyl acetate, formate, propionate or malonate; ethers, such as simple ketoesters, istherefore and simple dialkyl ethers, such as diisopropyl ether, diethyl ether, disutility ether, methyl tert-butyl ether, diethyl ether of diethylene glycol, and diethyl ether of ethylene glycol; aliphatic and aromatic hydrocarbons, such as toluene, xylene, heptane, octane, and petroleum fractions such as naphtha, white spirit, petroleum ether or benzene; halogenated hydrocarbons, such as dichloromethane; and N-alkylated lactams, such as N-organic N-cyclohexylpiperidine or N-dodecylmercaptan. The content of the solvent is, for example, a value in the range, in particular, 10-90 wt.%, preferably 20-80 wt.%, in terms of the whole composition.

Further, the curable composition, when used as a varnish, lacquer or primer coating may contain other components, in particular, triisocyanate, such as Tris(4-isocyanatophenyl)methane and Tris(4-isocyanatophenyl)thiophosphate; aminosilane, as, for example, 3-aminopropyltrimethoxysilane, N-(2-amino-ethyl)-3-aminopropyltrimethoxysilane, bis[3-(trimethoxysilyl)propyl]amine, 3-aminopropyltrimethoxysilane, 3-amino-methylpropionitrile, N-(2-amino-ethyl)-3-aminopropyltrimethoxysilane, 4-aminobutyraldehyde, 4-aminophthalonitrile, 4-amino-3-methylbutyronitrile, 4-amino-3,3-dimethylethoxysilane, 4-amino-3,3-dimethylaminobenzonitrile, [3-(2-aminoethylamino)propyl]trimethoxysilane (=4,7,10-triazacyclononane), 2-AMINOETHYLPIPERAZINE, 2-aminoethylaminomethyl, aminomethyltransferase, aminomethylenemalonate, aminoethylaminomethyl, 7-amino-4-exaggerated.amoxicillin, N-(methyl)-3-aminopropyltrimethoxysilane, N-(n-butyl)-3-aminopropyltrimethoxysilane; Tris[3-(trimethoxysilyl)propyl]amine, 1,3,5-Tris[3-(trimethoxysilyl)propyl]-1,3,5-triazine-2,4,6(1H,3H,5H)Trion-urea (=Tris(3-(trimethoxysilyl)propyl)isocyanurate)and related analogues, in which the methoxy group is replaced by ethoxypropane or isopropoxycarbonyl; mercaptoethane, as, for example, 3-mercaptopropionylglycine or 3-mercaptopropionate, epoxysilane, as, for example, 3-glycidylmethacrylate, 3-glycidylmethacrylate; ureidopenicillin, as well as adducts of amino - and/or mercaptoethanol with epoxides or epoxysilane, for example, with 3-glycidylmethacrylate; titanates, preferably those that include at least one associated with the titanium atom via an oxygen bond-t is tan Deputy, in particular, alkoxygroup, sulphonate group, carboxylate group, dialkylphosphate group, dialkylphosphate group or acetylacetonato group, and in the case of multiple substituents they may be the same or mixed with each other. Examples of such titanates are manufactured by Kenrich Petrochemicals under the trade name Ken-React® KR TTS, KR 7, KR 9S, KR 12, KR 26S, KR 33DS, KR 38S, KR 39DS, KR 44, KR 134S, KR 138S, KR 158FS, KR 212, KR 238S, KR 262ES, KR 138D, KR 158D, KR 238T, KR 238M, KR 238A, KR 238J, KR 262A, interfere 38J, KR 55, interfere 01, interfere 09, 12 interfere, interfere 38, Interfere 44, interfere 97, interfere 99, KR OPPR and KR OPP2, as well as manufactured by DuPont under the trade name Tyzor® ET, TPT, NPT, BTM, AA, AA-75, AA-95, AA-105, TE, ETAM and OGT.

Described varnish, lacquer or primer coating mainly containing at least one adhesion promoter in the form of the already mentioned silanes or titanates.

Described varnish, lacquer or primer coating mainly containing at least one of the previously mentioned catalysts.

Described varnish, lacquer or primer coating is usually applied to the substrate using a brush, felt, cloth, sponge or sprayer. This application is carried out manually or automatically, in particular by using the robots.

Described varnish, lacquer or primer coating react upon contact with water, particularly in view of the moisture in the air, already described way, and other reactive towards water components, such as, for example, contains titanate or silane group of compounds also react with water. In addition, carried out after coating, under certain conditions, start to evaporate the contained volatile solvents. In future, the substrate is formed of a strong, well-adherent film. Its thickness is mainly about 5-100 μm, in particular 10 to 50 microns.

The primer coating is mainly used as a bonding bridge for polymer compositions in the form of adhesives, sealants or coatings, such as, for example, the decking for the floor, in particular, polymeric compositions based on polyurethane with isocyanate groups and/or wilanowie groups.

Another aspect of the present invention relates to a method for bonding a substrate S1 to a substrate S2, which comprises the following stages:

i) applying the above-described curable composition on a substrate S1;

ii) bringing the applied composition into contact with a substrate S2 within an unlimited connection time;

or

i') applying the above composition to a substrate S1 and the substrate S2;

ii') bringing the applied composition into contact with each other for an unlimited connection time;

moreover, the subst is at S2 consists of the same material, as the substrate S1, or other material.

Another aspect of the present invention relates to a method of sealing. It includes the following stage:

i) applying the above-described curable composition between a substrate S1 and a substrate S2, so that the composition was kept in contact with the substrate S1 and the substrate S2;

moreover, the substrate S2 consists of the same material as the substrate S1, or other material.

Usually sealant zapressovyvajutsja in the so-called junction.

Another aspect of the present invention relates to a method for coating a substrate S1. It includes the following stage:

I') applying the above-described curable composition on a substrate S1 for an unlimited connection time.

In the case of these three methods are suitable substrates S1 and/or S2 are, for example, inorganic substrates such as glass, glass ceramic, concrete, mortar, brick, tile, plaster, and natural stones such as granite or marble; metals or alloys such as aluminum, steel, nonferrous metals, galvanized metals; organic substrates such as leather, cloth, paper, wood, associated with resin wood materials, composite materials, resin-textile, plastics, such as polyvinyl chloride (unplasticized and plasticized PVC), copolymers of Acrylonitrile, baladie the a and styrene (ABS), SMC (sheet molded materials), polycarbonate (PC), polyamide (PA), polyesters, emission spectra obtained for pure (polymethyl methacrylate), epoxy resins, polyurethanes (PUR), Polyoxymethylene (RUM), polyolefins (PO), in particular, treated on the surface with plasma, corona discharge or flame polyethylene (PE) or polypropylene (PP), copolymers of ethylene and propylene (EPM) and ternary copolymers of ethylene, propylene and diene (EPDM); substrates coated with a coating such as powder coated metals or alloys; and paints and varnishes, in particular, automotive lacquers.

The substrate, if necessary, before applying the composition can be subjected to pre-treatment. This kind of pre-treatment include, in particular, physical and/or chemical cleaning methods, such as grinding, sandblasting, brushing or the like, or treatment with cleaners or solvents, or the application of the adhesion promoter, the solution of the adhesion promoter or primer coating.

In the case of two-component composition, the two components K1 and K2 are mixed together shortly before application.

If termotorgmash composition applied composition then in the case of bonding, sealing or coating is subjected to a hot drying by heating it at a suitable temperature.

Application hotwired the emnd composition is carried out in a wide range of temperatures. For example, the composition can be applied at room temperature, which is typical for elastic adhesive or sealant. However, the composition can be applied also at lower and at higher temperatures. The latter in particular preferred when the composition contains a high-viscosity or melting the components that are usually found in hot-melt adhesives, such as Caloplaca adhesives (deplorable) or hot-melt adhesives (termoraspad). Temperature of application in the case of deplorable are in the range from 40°C to 80°C, in the case of thermoreceptive they are in the range of from 85°C to 200°C.

When using these described methods for bonding, sealing or coating, respectively, resulting from the use of one of these compositions in the form of one - or two-component adhesives, sealants, casting masses, coatings, flooring, paint, varnish, primers, coatings or foam - receive the product.

This product is, in particular, the design, particularly the design of above-ground or underground structures, or industrial product, or consumer goods, in particular, window, household machine or vehicle, in particular, water or land vehicle, preferably a car, bus, truck or to ABL, or assembling parts of the vehicle, or an item of furniture, textile or packaging industry.

EXAMPLES

1. Description of measurement methods

The viscosity is measured using a temperature-controlled viscometer type "cone-plane" Physica UM (cone diameter 20 mm, cone angle 1°, the distance between the apex of the cone and the plane of 0.05 mm, shear rate 10-1000-1).

The amine content, i.e. the total content of amino groups and blocked amino groups (alvinegro) in the resulting compounds, determine titrimetrically (using 0.1 G. HClO4in glacial acetic acid, against crystal violet) and always indicate in mmol N/g

The value of the PKandfor a conjugate acid Mannich bases is approximately determined by the potential of incomplete neutralization in potentiometric titration of approximately 1 mmol Mannich bases in 50 ml of water, or, where not possible, in 50 ml of a mixture of water and isopropanol in a ratio of 1:1, using 0.1 G. of HCl, and measured values in a mixture of water and isopropanol using standard substances recalculate the expected values in pure water.

Infrared spectra shoot at the instrument FT-IR 1600 Perkin-Elmer, solids in the form of press products with KBr in the direct radiation and liquid oils in the form of undiluted films (the EU is and you done by dissolving the substance in CH2Cl2and evaporation of the solvent) on the horizontal unified measurement node ATR using a ZnSe-crystal; the absorption bands are indicated in wave numbers (cm-1) (measurement range: 4000-650 cm-1); additive sh (shoulder) indicates appear in the form of a shoulder lane, the addition of br (ush.) indicates a broad band.

1H-NMR spectra shoot with a spectrometer type Bruker DPX-300 when 300,13 MHz; chemical shifts δ are indicated in ppm relative to tetramethylsilane (TMS), constant interaction J are specified in Hz; original samples and samples of pseudosatellite not differ.

2. Obtaining aldehydes

2,2-Dimethyl-3-(N-pyrrolidino)propanal

In a round bottom flask under nitrogen atmosphere was placed 51,0 g (to 0.72 mol) of pyrrolidine and dissolved in 100 ml of absolute ethanol. With good stirring and cooling with ice from a dropping funnel slowly added dropwise 40.6 g (0.40 mol) of 96%sulfuric acid, and pay attention to the fact that the temperature of the resulting suspension did not rise above 50°C. Then add to 23.8 g (0,79 mol) of paraformaldehyde and of 54.5 g (0,76 mol) of Isobutyraldehyde and the reaction mixture is stirred for 2 hours at an oil bath at a temperature of 120 ºC under reflux. Transparent reaction solution ohlajdauche room temperature, treated with 500 ml of 10%aqueous solution of sodium sulfite and alkalinized 10 N. NaOH solution. The organic phase is separated using a separating funnel and put aside. The aqueous phase is extracted with twice 50 ml of ethyl acetate, the extracts dried over anhydrous Na2SO4and concentrate. The combined organic phases fractionary in vacuum. Output: 79,2 g (71% of theory) in the form of colorless, transparent, with aminopterin smell fluids containing amine 6,34 mmol N/g and a viscosity of 3 MPa·s at 20°C.

Alternative receiving

In a round bottom flask under nitrogen atmosphere is placed to 59.8 g (to 0.72 mol) of 36%aqueous solution of formaldehyde and 53.8 g (0.75 mol) of Isobutyraldehyde. With good stirring and cooling with ice from a dropping funnel slowly added dropwise 51,0 g (to 0.72 mol) of pyrrolidine, and pay attention to the fact that the temperature of the reaction mixture did not rise above 20°C. after the addition was finished leave to mix for one hour at room temperature. The resulting turbid, colorless reaction mixture is stirred for 18 hours at an oil bath at a temperature of 100ºC under reflux, cooled to room temperature and the phases are separated using a separating funnel. The organic phase without further processing practioner the Ute in a vacuum. The product is distilled at a temperature of the top (columns) 80°C and a pressure of 17 kPa. Output: 95,9 g (86% of theory); colourless transparent liquid with amine content 6,34 mmol N/g

pKa≈ 9,2.

IR: 2962, 2928(shoulder), 2873, 2782 (SNO), 1724 (C=O), 1460, 1400, 1362, 1351, 1327, 1293, 1238, 1202, 1141, 1114, 1059, 1036, 1002, 965, 916, 906, 874, 774.

1H-NMR (CDCl3, 300 K) δ of 9.56 (s, 1H, CHO), 2,63 (s, 2H, NCH2C(CH3)2), 2.49 USD (m, 4H, NCH2CH2cycle.), 1,71 (m, 4H, NCH2CH2cycle.), a 1.08 (s, 6H, CH2C(CH3)2).

2,2-Dimethyl-3-(N-morpholino)propanal

In a round bottom flask under nitrogen atmosphere was placed 83,1 g (1.00 mol) of 36%aqueous solution of formaldehyde and 75.0 g (1.04 mol) of Isobutyraldehyde. With good stirring and cooling with ice from a dropping funnel slowly added dropwise to 87.1 g (1.00 mol) of the research, and pay attention to the fact that the temperature of the reaction mixture did not rise above 20°C. after the addition was finished leave to mix for one hour at room temperature. The resulting clear, colorless reaction mixture is stirred for 18 hours at an oil bath at 100°C under reflux, cooled to room temperature and the phases are separated using a separating funnel. The organic phase without further processing fractionary in vacuum. The product is distilled under pace is the atur top (columns) 97°C and a pressure of 14 mbar. Output: 145,5 g (85% of theory) as a colorless transparent liquid, almost devoid of smell, with the content of the amine 5,72 mmol N/g and a viscosity of 11 MPa·s at 20°C.

pKa≈ 6,3.

IR: 2958, 2981, 2850, 2803, 2695 (Cho, 1979, 1722 (C=O), 1455, 1402, 1374, 1361, 1319, 1280, 1268, 1206, 1137, 1115, 1070, 1035, 1015, 951, 906, 864, 801, 774.

1H-NMR (CDCl3, 300 K) δ of 9.55 (s, 1H, CHO), 3,63 (d, J=9,4, 4H, OCH2cycle.), 2,47 (s, 2H, NCH2C(CH3)2), is 2.44 (m, 4H, NCH2cycle.), a 1.08 (s, 6H, CH2C(CH3)2).

2,2-Dimethyl-3-(N-(2,6-dimethyl)morpholino)propanal

Under the same conditions as in the case of receiving 2,2-dimethyl-3-(N-morpholino)propanal, of 41.7 g (0.50 mol) of 36%aqueous solution of formaldehyde are subjected to interaction of 37.9 g (of 0.53 mol) of Isobutyraldehyde and 57.6 g (0.50 mol) of 2,6-dimethylmorpholine (BASF; mixture of isomers) and process. The product is distilled at a temperature of the top (columns) 104°C and a pressure of 20 mbar. Output: 80,8 g (81% of theory) as a colorless transparent with weak aminopterin smell of the liquid, which has an amine content of 4.99 mmol N/g

pKa≈ 5,9.

IR: 2970, 2933, 2868, 2799, 2771(shoulder), 2727, 2700(shoulder) (SNO), 2627, 1724 (C=O), 1456, 1403, 1373, 1362(shoulder), 1320, 1281, 1240, 1216(shoulder), 1178, 1144, 1077, 1042, 1003, 967, 946, 916, 887(shoulder), 879, 860, 837, 799, 773.

1H-NMR (CDCl3, 300 K) δ of 9.55 (s, 1H, CHO), 3,59 (ddcv, J=10,0/6,3/2,3, 2H, OCHCH3), to 2.57 (arcs, J=10,5/2,1, 2×1H from CH(CH3)-CH2N)2,44 (s, 2H, NCH2C(CH3)sub> 2), to 1.86 (DD, J=11.4 in/10,0, 2×1H from CH(CH3)-CH2N)a 1.11 (d, J=6,3, 6H, OCHCH3), was 1.06 (s, 6H, NCH2C(CH3)2).

2,2-Dimethyl-3-(N-benzylmethylamine)propanal

Under the same conditions as in the case of receiving 2,2-dimethyl-3-(N-morpholino)propanal, 39,2 g (0.47 mol) of 36%aqueous formaldehyde solution is subjected to interaction with a 35.6 g (0.49 mol) of Isobutyraldehyde and to 57.0 g (0.47 mol) of N-benzylmethylamine and process. The product is distilled at a temperature of the top (columns) 74°C and a pressure of 4·10-2mbar. Output: 80,6 g (83% of theory) as a colorless transparent and almost devoid of the smell of the liquid, which has an amine content of 4.83 mmol N/g

pKa≈ 7,2.

IR: 3084, 3060, 3026, 2962, 2928, 2870, 2840, 2784, 2700 (SNO), 1950, 1876, 1808, 1722 (C=O), 1654, 1602, 1584, 1542, 1494, 1452, 1420, 1398, 1362, 1316, 1290, 1256, 1172, 1118, 1074, 1038, 1024, 1002, 976, 948, 916, 910, 880, 856, 826, 774, 738, 698, 670.

1H-NMR (CDCl3, 300 K) δ 9,52 (s, 1H, CHO), 7,33-7,20 (m, 5H, Ph-H), 3,51 (s, 2H, Ph-CH2-N)at 2.59 (s, 2H, NCH2C(CH3)2), of 2.16 (s, 3H, NCH3), with 1.07 (s, 6H, NCH2C(CH3)2).

2,2-Dimethyl-3-(N-benzylisoquinoline)propanal

Under the same conditions as in the case of receiving 2,2-dimethyl-3-(N-morpholino)propanal, 28,0 g (0.34 mol) of 36%aqueous formaldehyde solution is subjected to interaction with 25.4 g (0.35 mol) of Isobutyraldehyde and 50.0 g (0.34 mol) of N-benzylisoquinoline and process. The product is distilled at a temperature of the top (columns) 100°C and a pressure of 4·10 -2mbar. Output: 48.6 g (62% of theory) in the form of a pale yellow, transparent and almost devoid of the smell of the liquid, which has an amine content to 4.28 mmol N/g

pKa≈ 6,6.

IR: 3084, 3060, 3026, 2962, 2929, 2869, 2823(shoulder), 2806, 2699 (SNO), 1948, 1869, 1722 (C=O), 1602, 1584, 1540, 1494, 1460, 1452, 1398, 1385, 1362, 1320, 1252, 1234, 1207, 1164, 1118, 1093, 1074, 1056, 1027, 1003, 965, 906, 877, 826, 772, 730, 697, 668.

1H-NMR (CDCl3, 300 K) δ 9,39 (s, 1H, CHO), 7,32-7,17 (m, 5H, Ph-H), 3,53 (s, 2H, Ph-CH2-N), 2,73 (Sept., J=6,6, 1H, NCH(CH3)2), 2,59 (s, 2H, NCH2C(CH3)2), and 1.00 (s, 6H, NCH2C(CH3)2), 2,73 (d, J=6,6, 6H, NCH(CH3)2).

2,2-Dimethyl-3-(N-cyclohexylethylamine)propanal

Under the same conditions as in the case of receiving 2,2-dimethyl-3-(N-morpholino)propanal, to 36.8 g (0.44 mol) of 36%aqueous formaldehyde solution is subjected to interaction with the 33.4 g (0.46 mol) of Isobutyraldehyde and 50.0 g (0.44 mol) of N-cyclohexylethylamine and process. The product is distilled at a temperature of the top (columns) 69°C and a pressure of 4·10-2mbar. Yield: 65.8 g (76 % of theory) in the form of colorless, transparent and odorless amine liquid, which has an amine content 4,94 mmol N/g

pKa≈ 8,4.

IR: 2925, 2851, 2796, 2685 (SNO), 1723 (C=O), 1464, 1450, 1422, 1396, 1376, 1381, 1344, 1319(shoulder), 1262, 1200, 1177, 1143, 1110, 1072, 1057(shoulder), 1045, 1025, 1004, 987, 960, 916, 890, 878, 859, 836, 784, 772.

1H-NMR (CDCl3, 300 K) δ of 9.55 (s, 1H, CHO), to 2.55 (s, 2H, NCH2C(CH3)2), 2,22 (m, 1H, NCHcycle.), of 2.20 (s, 3H, NCHsub> 3), of 1.74 (m, 4 Cy-H), to 1.60 (m, 1 Cy-H), 1,28-1,08 (m, 5 Cy-H)of 1.06 (s, 6H, CH2C(CH3)2).

N-(2,2-Dimethyl-3-oxopropyl)-N-methylpyrrolidine iodide

In nitrogen atmosphere 1.18 g (7.5 mmol) of 2,2-dimethyl-3-(N-pyrrolidino)propanal and 1.06 g (7.5 mmol) of methyliodide weighed into a glass (glass for pills), close it and shake well when turning. The mixture immediately becomes cloudy; a few minutes later at the bottom of the glass begins to accumulate sediment in white. The glass is allowed to stand at room temperature. After 90 minutes all content crystallizes in the form of white crystals.

IR (press product with KBr): 3042, 3002, 2982, 2958, 2890, 2874, 2838, 2734, 1754, 1720 (C=O), 1682, 1478, 1466, 1450, 1436, 1424, 1400, 1382, 1364, 1344, 1310, 1276, 1234, 1182, 1166, 1150, 1108, 1058, 1032, 1000, 974, 944, 916, 878, 820, 768, 732.

1H-NMR (D2O, 300 K) δ 9,65 (s, 1H, CHO), 3,81 (s, 2H, NCH2C(CH3)2), and 3,69 3,53 (2×m, 2×2H, NCH2CH2cycle.), with 2.93 (s, 3H, NCH3), 2,22 (m, 4H, NCH2CH2cycle.), of 1.34 (s, 6H, CH2C(CH3)2).

N-(2,2-Dimethyl-3-oxopropyl)-N-methylmorpholine iodide

In nitrogen atmosphere of 1.03 g (5.9 mmol) of 2,2-dimethyl-3-(N-morpholino)propanal and 0,83 g (5.9 mmol) of methyliodide weighed into a glass (glass for pills), close it and shake well when turning. The mixture becomes cloudy within 10 seconds; a few minutes later at the bottom of the glass begins to accumulate sediment is logo color. The glass is allowed to stand at room temperature for one hour and then heated to a temperature of 60°C. After 2 hours all content crystallizes in the form of white crystals.

IR (press product with KBr): 3018, 2976, 2958, 2872, 2812, 2724, 1768(shoulder), 1722 (C=O), 1685, 1476, 1462, 1420, 1400, 1384, 1370, 1312, 1280, 1248, 1220, 1176, 1144, 1120, 1082, 1066, 1039, 1016, 988, 952, 914, 900, 884, 868, 812, 772.

1H-NMR (D2O, 300 K) δ for 9.64 (s, 1H, CHO), 4,06 (m, 4H, OCH2cycle.), a 3.87 (s, 2H, NCH2C(CH3)2), and 3.72 (m, 4H, NCH2cycle.), is 3.21 (s, 3H, NCH3), to 1.37 (s, 6H, CH2C(CH3)2).

3. Getting aldimines

Example 1: aldimine a-1

In a round bottom flask under nitrogen atmosphere was placed 23.3 g of 1,6-diamine (70% in water; the content of amine 12,16 mmol N/g). Under intensive stirring of the dropping funnel type of 47.0 g of 2,2-dimethyl-3-(N-morpholino)propanal. Then the volatile component parts removed in vacuo (10 mbar, 80°C). Output: 57,2 g of clear colorless oil with an amine content 10,10 mmol N/g and a viscosity of 45 MPa·s at 20°C.

IR: 2961, 2926, 2872, 2858, 2804(shoulder), 2779, 1665 (C=N), 1459, 1446(shoulder), 1392, 1360, 1338, 1292, 1239, 1199, 1191, 1139, 1116, 1060, 1032, 1001, 964, 937, 905, 875, 727.

1H-NMR (CDCl3, 300 K) δ of 7.55 (t, J=1,2, 2H, CH=N), 3,34 (t×d, J=1,2/7,1, 4H, CH=N-CH2), 2.49 USD (m, 12H,cycle.CH2CH2NCH2C(CH3)), 1,71 (m, 8H,cycle.CH2CH2NCH2C(CH3)), and 1.56 (m, 4H, CH=N-CH2CH22CH2CH2), with 1.07 (s, 12H, CH2C(CH3)2).

Example 2: aldimine a-2

Under the same conditions as described in example 1 of 31.8 g of 1,6-diamine (70% in water; the content of amine 12,16 mmol N/g) is subjected to interaction with 71,0 g of 2,2-dimethyl-3-(N-morpholino)propanal. Output: 86,3 g of clear colorless oil with an amine content 9,19 mmol N/g and a viscosity of 145 MPa·s at 20°C.

IR: 2954, 2926, 2849, 2805, 2762(shoulder), 2687, 1980, 1665 (C=N), 1454, 1395, 1375, 1358, 1332, 1317, 1282, 1267, 1204, 1135, 1117, 1070, 1036, 1012, 944, 933, 882, 864, 802, 776(shoulder), 728.

1H-NMR (CDCl3, 300 K) δ 7,53 (t, J=1,2, 2H, CH=N)to 3.64 (d, J=9,3, 8H, OCH2cycle.), to 3.34 (m, 4H, CH=N-CH2), the 2.46 (m, 8H, NCH2cycle.), was 2.34 (s, 4H, NCH2C(CH3)2), of 1.57 (m, 4H, CH=N-CH2CH2), of 1.28 (m, 4H, CH=N-CH2CH2CH2), was 1.06 (s, 12H, CH2C(CH3)2).

Example 3: aldimine a-3

Under the same conditions as described in example 1 of 31.4 g of polyetherdiamine (Polyoxypropylenediamine with an average molecular weight of about 240 g/mol; Jeffamine® D-230, Hunstman; the content of amine 8,29 mmol N/g) is subjected to interaction with 20,0 g of 2,2-dimethyl-3-(N-morpholino)propanal. Output: of 31.4 g of a clear colorless oil with an amine content 7,14 mmol N/g and a viscosity of 170 MPa·s at 20°C.

IR: 2961, 2926, 2887, 2850, 2803, 2763(shoulder), 2690, 1980, 1663 (C=N), 1454, 1373, 1316, 1282, 1268, 1204, 1135(shoulder), 1114, 1070, 1036, 1012, 1001(shoulder), 946(shoulder), 929, 897, 882 864, 802, 775, 665.

1H-NMR (CDCl3, 300 K) δ EUR 7.57 (s, 2H, CH=N)to 3.64 (m, 8H, OCH2cycle.), 3,6-3,1 (m, about 12H, OCH2CH(CH3)), 2,46 (m, 8H, NCH2cycle.), was 2.34 (s, 4H, NCH2C(CH3)2), 1,18-0,97 (m, approximately 24H, OCH2CH(CH3and CH2C(CH3)2).

Example 4: aldimine a-4

Under the same conditions as described in example 1, 14,55 g of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/g) is subjected to interaction with 30,00 g of 2,2-dimethyl-3-(N-morpholino)propanal. Output: of 40.9 g of a clear colorless oil with an amine content 8,29 mmol N/g and a viscosity of 6.8 PA·s at 20°C.

IR: 2952, 2914, 2908, 2894, 2849, 2805, 2764(shoulder), 1980, 1663 (C=N), 1454, 1396(shoulder), 1377, 1361, 1352(shoulder), 1332, 1317, 1282, 1267, 1204, 1136, 1116, 1070, 1051, 1036, 1012, 968, 928, 881, 864, 802.

1H-NMR (CDCl3, 300 K) δ to 7.61 and 7.60 (2×s, the ratio is about 3/1, 1H, CH=N [isomer]), 7,49 (2×s, the ratio is about 3/1, 1H, CH=N [isomer]), to 3.64 (m, 8H, OCH2cycle.), 3,30 (m, 1H, CH=N-CHcycle.), 3,12 and 3,01 (2×d, J=11,1, 2H, CH=N-CH2Ccycle.), 2,47 (m, 8H, NCH2cycle.), was 2.34 (s, 4H, NCH2C(CH3)2), 1,53-0,85 (m, 27H, CH2cycle.and CH3).

Example 5: aldimine A-5

Under the same conditions as described in example 1, 6.25 g of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/g) will versaut interaction from 15.00 g of 2,2-dimethyl-3-(N-(2,6-dimethyl)morpholino)propanal. Yield: 19.7 g of a clear colorless oil with an amine content 7,33 mmol N/g and a viscosity of 10.5 PA·s at 20°C.

IR: 2968, 2952, 2930, 2907, 2862, 2808, 2769(shoulder), 2731, 2624, 1727, 1664 (C=N), 1456, 1396(shoulder), 1374, 1363, 1320, 1280, 1248, 1230, 1216, 1178, 1144, 1082, 1040, 1000, 968, 939, 916, 878, 864, 838, 803, 774.

1H-NMR (CDCl3, 300 K) δ to 7.61 and of 7.48 (2×m, 2×1H, CH=N), 3,62 (m, 4H, OCHCH3), and 3.31 (approximately 0,5H, CH=N-CH2Ccycle.[isomer]), or 3.28 (m, 1H, CH=N-CH=cycle.), 3,11 and 3,01 (2×d, J=11,1, about 1,5H, CH=N-CH2Ccycle.[isomer]), 2,62 (d, J=10,0, 4H from NCH2cycle.), 2,32 and 2,31 (2×s, 4H, NCH2C(CH3)2), 1.89 and is 1.81 (2×d, J=10,0, 4H from NCH2cycle.), 1,6-0,8 (m, 39H, CH2cycle.and all CH3).

Example 6: aldimine A-6

Under the same conditions as described in example 1, 6,07 g of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/g) is subjected to interaction with 15,00 g of 2,2-dimethyl-3-(N-benzylmethylamine)propanal. Yield: 19.7 g of a clear colorless oil with an amine content of 7.24 mmol N/g and a viscosity of 2.8 PA·s at 20°C.

IR: 3084, 3060, 3026, 2948, 2916, 2864, 2838, 2806, 2782, 2708, 1944, 1871, 1807, 1726, 1664 (C=N), 1602, 1585, 1541, 1494, 1452, 1418, 1386, 1377, 1362, 1322, 1260, 1249(shoulder), 1203(shoulder), 1188, 1168, 1120, 1074, 1036, 1026, 1000, 974, 939(shoulder), 904, 890, 858, 824, 736, 696, 670.

1H-NMR (CDCl3, 300 K) δ 7,63 and 7.50 (2×s, the ratio is about 3/1, 1H, CH=N [isomer]), 7,49 (m, 1H, CH=N), 7,34-to 7.18 (m, 10 Ph-H), 3,52, and 3,51 (2×s, 2×2H, PhCH 2N)3,30 (approximately 0,5H, CH=N-CH2Ccycle.[isomer]), with 3.27 (m, 1H, CH=N-CHcycle.), 3,10 and 2,99 (2×d, J=11,1, about 1,5H, CH=N-CH2Ccycle.[isomer]), 2,47 and 2.46 (2×s, 2×2H, NCH2C(CH3)2), 2,17 and 2.16 (2×s, 2×2H, NCH3), 1,6-0,8 (m, 27H, CH2cycle.and all C-CH3).

Example 7: aldimine a-7

Under the same conditions as described in example 1, 5.34 g of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/g) is subjected to interaction with 15,00 g of 2,2-dimethyl-3-(N-benzylisoquinoline)propanal. Yield: 19.2 g of a transparent pale yellow "honey" with the content of the amine 6,56 mmol N/g and a viscosity of 150 PA·s at 20°C.

IR: 3082, 3060, 3024, 2958, 2922, 2864, 2816, 2710, 1944, 1872, 1805, 1662 (C=N), 1602, 1585, 1494, 1460, 1452(shoulder), 1386, 1362, 1320, 1299, 1240, 1205(shoulder), 1164, 1116, 1092, 1074, 1054, 1026, 998, 966, 940, 890, 845, 826, 774, 728, 696.

1H-NMR (CDCl3, 300 K) δ 7,56 and 7,53 (2×s, the ratio is about 3/1, 1H, CH=N [isomer]), 7,41 (m, 1H, CH=N), 7,34-7,14 (m, 10 Ph-H), 3,59 and 3.57 (2×s, 2×2H, PhCH2N)3,18 (m, 1H, CH=N-CHcycle.), 2,98, and 2,89 (2×d, J=11,0, 2H, CH=N-CH2Ccycle.), 2,77 (m, 2H, NCH(CH3)2), is 2.44 (s, 4H, NCH2C(CH3)2), 1,6-0,8 (m, 39H, CH2cycle.and all CH3).

Example 8: aldimine a-8

Under the same conditions as described in example 1 of 6.31 g of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/is) is subjected to interaction with 15,00 g of 2,2-dimethyl-3-(N-cyclohexylethylamine)propanal. Output: a 19.6 g of colorless transparent "honey" with the content of the amine 7,38 mmol N/g and a viscosity of 28 PA·s at 20°C.

IR: 2924, 2850, 2807, 1726, 1664 (C=N), 1462(shoulder), 1450, 1378, 1362, 1345(shoulder), 1315(shoulder), 1260, 1200, 1176, 1140, 1116, 1103(shoulder), 1071(shoulder), 1044, 1026, 1001(shoulder), 986, 971(shoulder), 940(shoulder), 917, 890, 860, 836, 785.

1H-NMR (CDCl3, 300 K) δ of 7.64 and 7.62 (2×s, the ratio is about 3/1, 1H, CH=N [isomer]), to 7.50 (m, 1H, CH=N), 3,33 (approximately 0,5H, CH=N-CH2Ccycle.[isomer]), or 3.28 (m, 1H, CH=N-CHcycle.), 3,13 and 3,01 (2×d, J=11,1, about 1,5H, CH=N-CH2Ccycle.[isomer]), is 2.40 (s, 4H, NCH2C(CH3)2), of 2.23 (m, 8H, N(CH3)CHcycle.), of 1.74 (m, 8 Cy-H), to 1.59 (m, 2 Cy-H), 1,4-0,9 (m, 37H, Cy-H all C-CH3).

Example 9: aldimine A-9

Under the same conditions as described in example 1 9,05 g 2-(2-aminoethoxy)ethanol (DGA; Diglycolamine® Agent, Huntsman; amine content 9,39 mmol N/g) is subjected to interaction with 15,00 g of 2,2-dimethyl-3-(N-morpholino)propanal. Output: 22,5 g of clear colorless oil with an amine content to 7.61 mmol N/g and a viscosity of 130 MPa·s at 20°C.

IR: 3415 ush. (HE), 2953, 2919, 2887, 2850, 2805, 1665 (C=N), 1454, 1397, 1376, 1358, 1335, 1318, 1282, 1268, 1228 ush., 1206, 1115, 1068, 1036, 1012, 949, 927, 883, 863, 802.

1H-NMR (CDCl3, 300 K) δ 7,63 (t, J=1,3, 1H, CH=N), 3.75 to 3,55 (m, 12H, OCH2cycle.and HOCH2CH2OCH2CH2N=CH), 2,47 (m, 4H, NCH2cycle.), 2,43 (USS, 1H, OH), a 2.36 (s, 2H, NCH2C(CH3)2), with 1.07 (s, 6H, CH2C(CH3)2).

Example 10: aldimine A-10

Under the same conditions as described in example 1, 17,38 g of N-cyclohexyl-1,3-propandiamine (BASF; the content of amine 12,84 mmol N/g) subjected to the interaction of 20.00 g of 2,2-dimethyl-3-(N-morpholino)propanal. Output: 35,3 g of clear colorless oil with an amine content of 9.56 mmol N/g and a viscosity of 52 MPa·s at 20°C.

IR: 3304 ush. (NH), 2952(shoulder), 2924, 2849, 2808, 2687, 1726, 1664 (C=N), 1450, 1396, 1376(shoulder), 1360, 1349(shoulder), 1332, 1317, 1282, 1267, 1204, 1134, 1116, 1070, 1036, 1012, 932 ush., 886, 864, 846, 802, 735 ush.

Example 11: aldimine A-11

In pear-shaped flask 2.15 g (7.1 mmol) of N-(2,2-dimethyl-3-oxopropyl)-N-methylpyrrolidine iodide, in an atmosphere of nitrogen, dissolved in about 2 ml of water and to the solution was added with stirring of 0.58 g (3.5 mmol) of 1,6-diamine (70% in water; the content of amine 12,16 mmol N/g). Then the resulting clear, colorless solution is heated on an oil bath and volatile component parts removed in vacuo (10 mbar, 80°C). Get transparent vitreous product is a pale yellow color.

Alternative receiving

In nitrogen atmosphere 1,00 g aldimine a-1 and 0.73 g (5.1 mmol) of methyliodide weighed into a glass (for pills), close it and shake well when turning. The mixture immediately weakly turbid; a few minutes later at the bottom of the glass begins to accumulate sediment in the form of a pale yellow oil. The glass is left to stand for one hour at anatoy temperature and then heated to 60°C. After 2 hours all content solidifies in the form of a glassy oil is light yellow in color.

IR: 2962, 2928, 2852, 2834(shoulder), 2780(shoulder), 1724 (C=O), 1664 (C=N), 1460, 1386, 1366, 1342, 1306, 1262, 1222, 1168, 1142, 1114, 1098, 1042, 1002, 970, 942, 928, 904, 890, 824, 789, 730.

1H-NMR (D2O, 300 K) δ 7,88 (s, 2H, CH=N), 3.68 and 3,51 (2×m, 8H and 4H,cycle.CH2CH2N(CH3)CH2C(CH3)2), of 3.48 (t, J=7,0, 4H, CH=N-CH2), of 2.97 (s, 6H, NCH3), 2,20 (USM, 8H,cycle.CH2CH2N)to 1.59 (m, 4H, CH=N-CH2CH2), to 1.31 (m, 16H, CH=N-CH2CH2CH2and CH2C(CH3)2).

Comparative example 12: aldimine A-12

In a round bottom flask under nitrogen atmosphere place of 50.9 g (0.18 mol), distilled 2,2-dimethyl-3-euroelections. Under intensive stirring of the heated dropping funnel slowly add 10.0 g (0,17 mol N) 1,6-diamine (BASF; the content of amine 17,04 mmol N/g), and the mixture is heated and quickly becomes cloudy. Then the volatile component parts removed in vacuo (10 mbar, 80°C). Output: 57,7 g of a clear oil pale yellow color with the content of the amine to 2.94 mmol N/g

Comparative example 13: aldimine A-13

Under the same conditions as described in example 12, of 74.3 g (0.26 mol), distilled 2,2-dimethyl-3-euroelections subjected to interaction with 30.0 g (0.25 mol N) polyetherdiamine (Polyoxypropylenediamine with an average molecular weight of about 240 g/mol; Jeffamine® D-30, Huntsman; amine content 8,29 mmol N/g). Output: of 99.5 g of a clear oil pale yellow color with amine content of 2.50 mmol N/g

Comparative example 14: aldimine A-14

Under the same conditions as described in example 12, 55,0 g (to 0.19 mol), distilled 2,2-dimethyl-3-euroelections subjected to interaction with 15.6 g (0.18 mol N) 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (ISOPHORONEDIAMINE accessories > or; Vestamin® IPD, Degussa; the content of amine 11,67 mmol N/g). Output: 67,1 g of clear colorless oil with an amine content by 2.73 mmol N/g

4. Getting connections AV1

Example 15: aldimine a-15

In the first stage, 590 g of polyol Acclaim® 4200 N (polypropyleneoxide, HE is the number 28.5 mg KOH/g; Bayer), 1180 g of polyol Caradol® MD34-02 (polypropyleneoxide, IT is the number is to 35.0 mg KOH/g; Shell) and 230 g of isophoronediisocyanate (IPDI; Vestanat® IPDI, Degussa), according to a known method at a temperature of 80°C is subjected to interaction with the receipt containing terminal NCO-groups of the polyurethane polymer with titrimetrically specific content of free isocyanate groups of 2.1 wt.% and a viscosity of 22 PA·s at 20°C.

To 10,00 g of this polyurethane polymer (5.0 mEq. NCO) at room temperature add 1,31 g (5.0 mmol) aldimine A-9, obtained according to example 9, the mixture was mixed thoroughly using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.) and then heated to a temperature of 60°C. After 24 hours in the FTIR spectrum (at 2265 cm-1no longer detect NCO-bands. Get transparent homogeneous and devoid of odor liquid with amine content of 0.44 mmol N/g and a viscosity of 110 PA·s at 20°C.

IR: 3340 ush. (NH), 2967, 2929, 2893(shoulder), 2864, 1720 (C=O), 1666 (C=N), 1529, 1454, 1372, 1344, 1299, 1282, 1239, 1094, 1013, 925, 908(shoulder), 865, 835, 775, 660.

5. Getting curable compositions

Examples 16 to 20 and comparative example 21

In a glass made of polypropylene with screw lock using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTeck Inc.; 1 minute at 2500 rpm) mixed polyurethane polymer 1, receipt of which is described below, with aldimines, and catalyst to the formation of homogeneous mass thus obtained mass immediately fill varnished inside the aluminum tube and sealed. Used aldimine and types of catalyst in the case of each of the examples listed in table 1 mass parts.

Polyurethane polymer 1 was prepared as follows:

590 g of Polyol Acclaim® 4200 N (polypropyleneoxide, HE is the number 28.5 mg KOH/g; Bayer), 1180 g of polyol Caradol® MD34-02 (polypropyleneoxide, IT is the number is to 35.0 mg KOH/g; Shell) and 230 g of isophoronediisocyanate (IPDI; Vestanat® IPDI, Degussa), according to a known method at a temperature of 80°C is subjected to interaction with the receipt containing NCO-terminal g is uppy polyurethane polymer with titrimetrically specific content of free isocyanate groups of 2.1 wt.% and viscosity. 22 PA·s at 20°C.

The ratio between isocyanate groups and blocked amino groups in the case of all examples is 1.0/0,7.

Table 1
The composition of examples 16 to 20 and comparative example 21
Example161718192021 (comparison)
Polyurethane polymer 150,050,050,050,050,050,0
AldimineA-4, 4,21A-5, 4,79A-6, 4,89A-7, of 5.40A-8, 4,74-
The acid catalystand0,050,050,050,050,05-
The catalyst based on tinb0,050,050,050,050,05
andsalicylic acid;
bwt.% dibutyltindilaurate in diisodecylphthalate

The thus obtained compositions are experiencing in terms of stability during storage, the time of formation of a surface film, and mechanical properties after curing.

The storage stability is determined by the change in viscosity during heat aging. This composition is kept in a sealed tube in a furnace at a temperature of 60°C and measure the viscosity at 20°C, for the first time after 4 hours and again after 7 days of storage duration. The storage stability is obtained from the increase in the percent of the second viscosity value in relation to the first.

To measure the time of formation of the surface film (time to extinction tack-free, tack-free time without") a small portion of seasoned for 4 hours at 60°C composition is applied to the cardboard with a layer thickness of approximately 2 mm and under normal climatic conditions (temperature 23ºC±1OC, relative humidity 50%±5%) determine the time, which lasts up until when lightly touch the surface of the composition with POM is using a pipette from low density polyethylene (LDPE) for the first time no more remnants of the pipette.

To determine the mechanical properties with the use of most of the compositions have film thickness of 3 mm, pouring the composition into a flat shape of PTFE and otorita within 7 days under normal weather conditions. Get transparent, non-sticky and elastic polyurethane film, which do not contain bubbles. From films cut on the stamp samples for testing in the form of a double blade length 75 mm, when the length of the jumper 30 mm and the width of the lintel 4 mm, and subjected to the test according to DIN EN 53504 on the tensile strength, elongation at break and E-modulus (tensile 0.5 to 5%) (stretch speed: 200 mm/min).

The results of these tests are presented in table 2.

Table 2
Properties of the compositions of examples 16 to 20 and comparative example 21
Example161718192021 (comparison)
Viscosity after 4 hours (PA·s)21,821,0a 21.523,124,5 19,0
Viscosity after 7 days (PA·s)23,621,721,723,826,5to 19.9
The viscosity increase (%)and831385
During the formation of a surface film (min)6065707560>480
Tensile strength (MPa)4,1a 3.93,43,63,6n.b.b
Elongation at break (%)520500510530590n.b.b
E-modulus (MPa)1,71,31,41,2n.b.b
and=(viscosity after 7 days/viscosity 4 hours later)-1)×100%;
bnot defined

Examples 22-27:

Elastic one-component (1K) sealants (e.g., for expansion joints)

In the case of each example, the respective components according to table 3, in the above mass parts without pre-drying process using a vacuum mixer, with the exclusion of moisture air, to contain no lumps homogeneous paste it immediately fill lacquered inside aluminum and cartouche cartouche tightly closed.

Polyurethane polymer 1 are as described in example 16.

Urea thickener was prepared as follows:

In a vacuum mixer is placed 3000 g diisodecylphthalate (DIDP; Palatinol® Z, BASF) and 480 g of 4,4'-etilendiamindisuktsinatov (MDI; Desmodur® 44 MC L, Bayer) and slightly heated. Then slowly, with vigorous stirring, added dropwise 270 g monomethylamine. The resulting paste is stirred further for one hour in vacuum and cooled.

The ratio between the isocyanate groups and the amount of blocked amino groups (and oxazolidinone groups consider doubly) with what is in the case of all examples 1,0/0,67.

Table 3
The composition of the elastic one-component polyurethane (1K-PUR) sealants
Example222324 (EUR.)25 (EUR.)26 (EUR.)27 (EUR.)
Polyurethane polymer 124,024,024,024,024,024,0
AldimineA-3, 2,25A-4, 1,93A-13, 3,22A-14, 2,95--
Oxazolidinand----0,99-
The plasticizerb2,152,471,181,453,41 the 4.7
Chalk38,038,038,038,038,038,0
Gwith28,028,028,028,028,028,0
Titanium dioxide4,54,54,54,54,54,5
Epoxysilaned0,20,20,20,20,20,2
The acid catalyste0,60,60,60,60,6-
The catalyst based on tinf0,30,30,3 0,30,30,6
andhardener OZ, Bayer; amine content = 4,05 mmol/g;
bdiisodecylphthalate (DIDP; Palatinol® Z, BASF);
withurea thickener;
d3-glycidoxypropyltrimethoxysilane (Dynasylan® GLYEO, Degussa);
esalicylic acid (5 wt.% in dioctyladipate);
fdibutyltindilaurate (5 wt.% in diisodecylphthalate)

The thus obtained sealants facing in relation to the time of formation of a surface film, the speed of curing, adhesive, paint and mechanical properties after curing.

During the formation of a surface film determined as described in example 16.

The rate of curing determine, applying sealant cartouche-gun through the round end (hole 10 mm) in a horizontal, loose cone length of about 50 mm and a thickness in the mid 30 mm fixed on the wall a piece of cardboard, leave for 7 days under normal weather conditions, then in the middle vertically cut and determine the thickness of the cured layer using a scale ruler.

Stickiness is determined by pressure of the thumb on Mature within one day, respectively, for 3 days in the sample for testing your finger on the shore, and the ATEM purely quantitatively evaluate, how long the test remains stuck to the thumb on the raised hand (stickiness high/medium/low/no).

Staining assessed by size (large/middle/small/no) fat ring which is formed a week after the application of the sample to test on shore And on the sheet of paper on which was applied the fresh sample for testing.

To determine the mechanical properties after curing is measured hardness shore a, tensile strength, elongation at break and stress at elongation of about 100%. Shore a hardness As determined according to DIN 53505 using hardened within 14 days under normal weather conditions of samples for testing. For testing against other mechanical properties of the sealant 2 hours after getting pressed with a press from obtaining a film thickness of approximately 2 mm, film utverjdayut within 14 days under normal weather conditions, and test according to DIN EN 53504 on the tensile strength, elongation at break and stress at elongation of about 100% (stretch speed: 200 mm/min).

The test results presented in table 4.

Table 4
Properties of Elasti the ing 1K-PUR sealants
Example222324 (EUR.)25 (EUR.)26 (EUR.)27 (EUR.)
During the formation of a surface film (minutes)509016524590>480
Full cure (mm)10866158*
Adhesion after 1 dayaveragenohighminorhighhigh
Stickiness after 3 daysaveragenohighnoaveragehigh
Stainingnoaverageaverageaveragelarge
Hardness shore a283621313527
Tensile strength (MPa)2,73,02,52,61,41,9
Elongation at break (%)1000930104010005301000
Stress at 100%elongation (MPa)0,50,60,40,40,60,4
*clear bubbles

Example 28 and comparative examples 29-31:

Elastic 1K - adhesives (for example, for a con is e.g., installation)

In the case of each example, the respective components according to table 5, these mass parts without pre-drying process using a vacuum mixer, with the exclusion of moisture air, to contain no lumps homogeneous paste it immediately fill lacquered inside aluminum and cartouche cartouche tightly closed.

Polyurethane polymer 1, respectively, urea thickener receive, as described in example 16, respectively, in example 22.

The ratio between the isocyanate groups and the amount of blocked amino groups (and oxazolidinone think twice) is in the case of all examples 1,0/0,52.

Table 5
The composition of the elastic 1K-PUR-adhesives
Example2829 (EUR.)30 (..)31 (EUR.)
Polyurethane polymer 135,035,035,035,0
AldimineA-4, 2,73A-14,
4,17
- -
Oxazolidinand--1,40-
A crosslinking agentb0,80,80,80,8
Chalk27,027,027,027,0
Gwithof 28.2726,8329,6031,50
Titanium dioxide4,54,54,54,5
Epoxysilaned0,20,20,20,2
The acid catalyste1,01,01,0-
The catalyst based on tinf0,50,5 0,51,0
andhardener OZ, Bayer; amine content = 4,05 mmol/g;
bHDI-trimerized (Desmodur® N 3600, Bayer), NCO content = 23.0 wt.%;
withurea thickener;
d3-glycidoxypropyltrimethoxysilane (Dynasylan® GLYEO, Degussa);
esalicylic acid (5 wt.% in dioctyladipate);
fdibutyltindilaurate (5 wt.% in diisodecylphthalate)

Thus the resulting adhesives are experiencing in relation to the time of formation of a surface film, full speed curing, dyeing and mechanical properties after curing, as described in example 22, and instead of voltage in case of voltage tensile 100% is specified, the E-modulus (tensile 0.5 to 5%). The test results presented in table 6.

Table 6
The elastic properties 1K-PUR-adhesives
Example2829 (EUR.)30 (..)31 (EUR.)
During the formation of a surface film (min)7019050Full cure (mm)88129
Stainingsmallsmallsmalllarge
Hardness shore a43434345
Tensile strength (MPa)2,52,21,4Ni*
Elongation at break (%)620640320Ni*
E-modulus (MPa)3,73,03,7Ni*
*immeasurable because of the strong bubble

Examples 32-37 and comparative examples 38-40: two-component (2K) casting masses

In the case of each example, the corresponding integral part of componenta K2, according to table 7, in the specified mass parts without pre-drying is weighed in a glass made of polyethylene with screw stopper and using a centrifugal mixer (SpeedMixer™ DAC 150, FkackTek Inc.; 2 minutes at 3000 rpm./min), stirred until the formation of homogeneous cream.

Table 7
The composition of two-component polyurethane casting mass
Example32333435363738 (EUR.)39 (EUR.)40 (EUR.)
Component K1:
PMDIa30,430,829,730,232,8of 31.829,2 28,929,7
Component K2:
Castor oilb22,522,522,522,522,522,522,522,522,5
Diol dimer fatty acidwithof 17.5of 17.5of 17.5of 17.5of 17.5of 17.5of 17.5of 17.522,5
Triold4,754,754,754,754,754,754,754,754,75
AldimineA-1, 5,0A-2, 5,0A-3, 5,0A-4, 5,0A-9, 5,0A-10, 5,0A-12,
5,0
A-13,
5,0
-
The acid catalyste0,250,250,250,250,250,250,250,250,25
Chalkf50,050,050,050,050,050,050,050,050,0
aDesmodur® VKS 20 F, Bayer; NCO content = 30.0 wt.%;
bHE is number = 165 mg KOH/g;
withSovermol® 908, Cognis; HE-number = 200 mg KOH/g;
dDesmophen® 4011 T, Bayer; OH number = 550 mg KOH/g;
esalicylic acid (5 wt.% in dioctyladipate);
fOmyacarb® 5-GU, Omya.

To it add specified in table 7 mass parts PMDI in ka is este component K1 and stirred for 30 seconds at 3000 rpm./min). The ratio between the isocyanate groups of component K1 and the amount of the reactive groups (hydroxyl groups and antiminority) component K2 is always 1.1.

The thus obtained two-component polyurethane casting masses experience in terms of speed curing, mechanical properties and formation of bubbles.

Table 8
Properties of two-component polyurethane casting mass
Example32333435363738 (EUR.)39 (EUR.)40 (EUR.)
The lack of stickiness (min)and102030223038385848
Hardness shore D after 1 day818481 828877586060
Hardness shore D after 3 days879390879292727375
Shore a hardness after 7 days919493919694838482
Hardness shore D; subjected to annealingb889494919696898685
Tensile strength (MPa)of 21.931,223,220,2 32,322,711,011,08,1
Elongation at break (%)36162055657560
E-modulus (MPa)61074057050583064010085100
Bubblesnonononononononoa lot
andthe time until the lack of stickiness (time to extinction tack-free);
bthe curing 4 hours at 105°C for samples to be tested, hardened for 7 days at normal is somaticheskih conditions.

An indication of the speed of curing get, first, by determining the time until disappearance tack-free surface, which was measured in the same manner as during the formation of a surface film, as described in example 16. Secondly, for the further course of curing monitored by periodic measurements of shore hardness D according to DIN 53505.

Determination of tensile strength, and elongation at break and E-modulus (tensile 0.5 to 3%) is carried out according to DIN EN 53504 using the obtained watering films with a thickness of approximately 2 mm, which otverzhdajutsja within 7 days under normal weather conditions (stretch speed: 10 mm/min).

Blistering quantitatively evaluated on the basis of the number of bubbles that appear when cured film with a thickness of 2 μm under normal weather conditions.

The results of these tests are presented in table 8.

Examples 41-43: two-component semi-structural adhesives

In the case of each example, the corresponding compound of the component K2, according to table 9, in the above mass parts without pre-drying is weighed into a beaker made of polypropylene with screw stopper and using a centrifugal mixer (SpeedMixer™ DAC 150, FkackTek Inc.; 2 minutes at 3000 rpm./min), stirred until the formation of Homo is built of cream. To it add specified in table 9 mass parts PMDI as a component K1 and stirred for 30 seconds at 3000 rpm).

Table 9
The composition of the semi-structural 2K-PUR-adhesives
Example414243
Component K1:
PMDIa25,025,425,0
Component K2:
Castor oilb22,522,422,4
Diol dimer fatty acidwith7,5--
PPG 1000d12,522,422,4
Triole2,25,25 2,25
AldimineA-2, 5,0A-4, 5,0A-9, 5,0
The acid catalystf0,250,250,25
Chalkg50,050,050,0
aDesmodur® VKS 20 F, Bayer; NCO content = 30.0 wt.%;
bHE is number = 165 mg KOH/g;
withSovermol® 908, Cognis; HE-number = 200 mg KOH/g;
dDesmophen® 1112 BD, Bayer; HE-number = 112 mg KOH/g;
eDesmophen® 4011 T, Bayer; HE-number = 550 mg KOH/g;
fsalicylic acid (5 wt.% in dioctyladipate);
gOmyacarb® 5-GU, Omya.

The ratio between the isocyanate groups of component K1 and the amount of the reactive groups (hydroxyl groups and antiminority) component K2 is always 1.1.

The thus obtained two-component polyurethane adhesives are experiencing in terms of speed curing, mechanical properties and formation of bubbles, as described in example 32. The test results presented in table 10.

Tab the Itza 10
The semi-structural properties of two-component polyurethane adhesives
Example414243
The lack of stickiness (min)and233735
Hardness shore D after 1 day544956
Hardness shore D after 3 days747271
Hardness shore D after 7 days797881
Hardness shore D; subjected to annealingb727475
Tensile strength (MPa)10,29,510,2
Elongation at break (%)538664
E-module (the PA) 854991
Bubblesnonono
andthe time until the lack of stickiness (time to extinction tack-free in minutes);
bthe curing 4 hours at 105°C for samples to be tested, hardened within 7 days under normal weather conditions.

Examples 44-45 and comparative example 46: Elastic one-component coating (for example, in the case of flooring)

In the case of each example, the corresponding part of the weight of the coating, according to table 11, in the specified mass parts without pre-drying is weighed in a glass made of polyethylene with screw stopper and using a centrifugal mixer (SpeedMixer™ DAC 150, FkackTek Inc.; 2 minutes at 2500 rpm./min), mix, mix immediately fill varnished inside the aluminum tube and seal. The corresponding ratio between eliminarpremio and isocyanate groups (ratio aldimine/NCO) is indicated in table 11.

Polyurethane polymer 2 was prepared as follows:

1060 g Polyoxypropylene (Desmophen® 1111 BD, Bayer; IT is the number is byr111.4 mg KOH/g), 650 g polyoxypropylene Ndola (Desmophen® 2061 BD, Bayer; IT is the number is to 56.1 mg KOH/g), 770 g of isophoronediisocyanate (Vestanat® IPDI, Degussa) and 0.25 g of dioctyladipate at a temperature of 80°C is subjected to interaction, gaining containing terminal NCO-groups of the polyurethane polymer with a content of free isocyanate groups of 6.8 wt.%/

Table 11
Part one-component polyurethane masses for coatings
Example444546 (EUR.)
Polyurethane polymer 250,050,050,0
IPDI-trimerizedand24,024,024,0
AldimineA-2, 21,0A-4, 21,0A-12, 21, 0mm
The acid catalystb1,51,51,5
Amine catalystwith0,750,750,75
The catalyst based on tind0,750,750,75
The none2,02,02,0
The ratio aldimine/NCO0,750,700,49
and45 wt.% IPDI-trimerized (Vestanat® T 1890/100, Degussa; NCO content = 17.3 wt.%) in xylene;
bsalicylic acid (5 wt.% in dioctyladipate);
with2,2'-disorganizational ether (DABCO®DMDEE catalyst; Air Products);
d10 wt.% dibutyltindilaurate in diisodecylphthalate;
eBYK-088 (BYK-Chemie/ALTANA).

The thus obtained one-component polyurethane compound for coating experience in terms of stability during storage, the time of formation of surface films, mechanical properties, blistering and odors.

The storage stability is determined by comparing the viscosity of the mass of the coating before and after storage at elevated temperature. The weight of the coating is kept in a sealed tube in a furnace at a temperature of 40°C and measure its viscosity, for the first time 2 hours after cooking the second time after 24 days of age.

During the formation of a surface film determined as described in example 16. The mechanical properties determined in the same manner as described in example 16, and the curing time under normal weather conditions is, in the case of samples for testing shore 28 days, film - 21 days.

The odor assess quantitatively by smell at a distance of 10 cm from utverzhdenii film.

The results of these tests are presented in table 12.

55D
Table 12
Properties of one-component polyurethane masses for coatings
Example444546 (EUR.)
The viscosity before storage (MPa·s)380640220
The viscosity after storage (MPa·s)7801120350
During the formation of a surface film (min)3178160
The shore hardness (a or D)87A69A
Tensile strength (MPa)15,923,08,8
Elongation at break (%)350260310
E-modulus (MPa)8526018
Bubblesnonobit
Odornonono

Example 47: Elastic two-component coating (for example, in the case of flooring)

To obtain the component K1, 64 massdata (mass) polyurethane polymer 2, 32 mass 45 wt.% solution of IPDI-triseriata in xylene (Vestanat® T 1890/100, Degussa; with the content of 17.3 wt.% NCO), 1 mass acid catalyst (5 wt.% salicylic acid dioctyladipate), 0,5 mass amine catalyst (2,2'-disorganizational ether, DABCO®DMDEE catalyst, Air Products), 1 mass catalyst based on tin (10 wt.% dibutyltindilaurate in diisodecylphthalate) and 1, MASC the non (BYK-088, BYK-Chemie/ALTANA) without pre-drying is weighed in the cartouche of polypropylene and stirred using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.; 30 seconds at 2500 rpm). To the mixture of 19.5 mass aldimine A-5 as a component K2 and stirred for 30 seconds at 2500 rpm). The ratio between the isocyanate groups of component K1 and the amount of the reactive groups (hydroxyl groups and antiminority) component K2 is 1.1.

Polyurethane polymer 2 receive, as described in example 44.

The thus obtained two-component polyurethane adhesive for coating facing in relation to time, to lack of adhesiveness, mechanical properties after curing and formation of blisters and odors.

Time before the lack of stickiness determined in the same manner as during the formation of a surface film according to example 16. The mechanical properties determined in the same manner as described in example 16, and the curing time under normal weather conditions sample for testing shore is 28 days, film - 14 days. Blisters and odor define, as described in example 44.

The results of these tests are presented in table 13.

Table 13
Properties of two-component polyurethane compound for coating
Example47
The time until the lack of stickiness (min)135
Hardness shore a87
Tensile strength (MPa)9,5
Elongation at break (%)370
E-modulus (MPa)34
Bubblesno
Odorno

Example 48: one-component paint (suitable as a varnish or primer coating)

The mixture of 1.00 g of polyurethane polymer 3, the receipt of which is described below, 0.29 grams aldimine a-4 0.10 g of 3-glycidoxypropyltrimethoxysilane and on the tip of a spatula of salicylic acid diluted with ethyl acetate until a solids content of 50 wt.%/

Polyurethane polymer 3 was prepared as follows:

1,00 g Polyoxypropylene (Desmophen® 1112 BD, Bayer; HE-number = 112 mg KOH/g), 4,06 g IPDI-triseriata (Vestanat® T 1890/100, Degussa) and of 5.06 g this is lazette, according to a known method at a temperature of 60°C is subjected to interaction, receiving a polyurethane polymer with titrimetrically specific content of free isocyanate groups of 5.7 wt.%

A small portion of the resulting solution using a brush apply a thin layer to cleansed heptane glass plate (float glass; firm Rocholl, Schönbrunn, Germany) and incubated under normal weather conditions. After 30 minutes of non-adhesive forms, brilliantly transparent and well adherent film with a completely dry surface. After 3 days, the film shows the hardness determined according to the method of the pencil (hardness scratching on Wolff-Wibron, measured according to ISO 15184), from 6N to 7H. The adhesion of the film to the glass is excellent (no peeling when scratched with a pencil hardness N).

Another part of the solution in the manner described is applied to the other glass plate and incubated under normal weather conditions. After 30 minutes on the deposited film is applied one-component polyurethane adhesive (SikaTack® Ultrafast manufactured by Sika Schweiz AG) in the form of a "triangular" corrugated tape and the glass plate was incubated for 7 days under normal weather conditions, and the adhesive is subjected to curing. Then test the adherence of the adhesive gomero the Anna tape to the base, notching corrugated tape with a knife at one end of the bleed to the basics, hold the cut end of the hand and then gently and slowly, otstaiva in the direction of the other end of the corrugated strip, remove, respectively, are separated from their bases, and corrugated ribbon systematically make an incision with a knife perpendicular to the direction of stretching when it is exposed to the risk of rupture. Adhesion of corrugated tape is excellent; the gap is 100% in the case of an adhesive (cohesive fracture).

Excessive residual, not the applied solution is maintained in sealed relation to the climatic conditions of the vessel for several weeks without significant increase in viscosity.

1. Aldimine used as a latent curing agent containing isocyanate groups, systems, formulas (I)

where And means
or the remainder of an amine after removal of n primary aliphatic amino groups and m NH-groups,
or together with R7means (n+2)-valent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen;
n denotes 1 or 2, or 3, or 4, preferably 1 or 2,
m means 0, 1, or 2, or 3, or 4
provided that the sum is a (m+n) mean 2, or 3 or 4 or 5;
R1and R2or, independently of one another, denote each a monovalent hydrocarbon residue with 1 to 12 carbon atoms,
or together denote divalent hydrocarbon residue with 4 to 12 carbon atoms, which is part replaced, if necessary, carbocycle from 5 to 8, preferably 6, carbon atoms;
R3means a hydrogen atom, or alkyl group, or arylalkyl group, or alkoxycarbonyl group, in particular, with 1-12 carbon atoms;
R4and R5or, independently of one another, denote each a monovalent aliphatic, cycloaliphatic or arylaliphatic residue with 1-20 carbon atoms which does not contain hydroxyl groups and which, if necessary, contains heteroatoms in the form of a simple oxygen ether or tertiary amine nitrogen,
or together denote divalent aliphatic residue with 3 to 20 carbon atoms, which is part replaced, if necessary, a heterocycle with 5 to 8, preferably 6, atoms in the cycle, and this cycle does not contain a hydroxyl group and, together with the nitrogen atom, if necessary, contain other heteroatoms in the form of a simple oxygen ether or tertiary amine nitrogen; provided that when m=0 and n=3, R4and R5do not have tertiary amine nitrogen,
the means O or S, or N-R6or N-R7,
where R6either means monovalent hydrocarbon residue with 1-20 carbon atoms, which contains, if necessary, at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,
either means the Deputy of the formula (II)

where p denotes 0 or an integer from 1 to 10000 and
In means (p+1)-valent hydrocarbon residue, which, if necessary, contains a simple oxygen ether, tertiary amine nitrogen, hydroxyl groups, secondary amino groups or mercaptopropyl.

2. Aldimine formula (I) according to claim 1, wherein m=1 or 2, or 3, or 4.

3. Aldimine formula (I) according to claim 2, characterized in that it is aldimine formula (Ia)

where a1does not contain active hydrogen and does not contain a primary amino group and
together with R9means trivalent hydrocarbon residue with 3-20 carbon atoms, which, if necessary, contains at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen;
X1means O or S or N-R8or N-R9,
where R8either means monovalent hydrocarbon residue with 1-20 at the Mami carbon which, if necessary, contains at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,
either means the Deputy of the formula (IIa)

where1means divalent, if necessary, oxygen-containing simple ether or tertiary amine nitrogen, a hydrocarbon residue with 2 to 12 carbon atoms.

4. Aldimine formula (I) according to claim 1, characterized in that m=0.

5. Aldimine formula (I) according to claim 4, characterized in that it is aldimine formula (Ib)

where t represents 2 or 3, preferably 2;
And2means the residue polyamine with t primary amino groups after removal of the t primary amino groups and does not contain active hydrogen.

6. Aldimine formula (I) according to one of the preceding paragraphs, wherein R1and R2each denote methyl.

7. Aldimine formula (I) according to one of claims 1 to 5, characterized in that R is hydrogen.

8. Aldimine formula (I) according to one of claims 1 to 5, wherein R4and R5
either each independently of one another denote ethyl, propyl, isopropyl, butyl, 2-ethylhexyl, cyclohexyl or benzyl,
or together with inclusion of the nitrogen atom form a loop, in particular, pyrolidine piperidinyl, morpholinyl or N-alkylpiperazine cycle, and this cycle, if necessary, replaced.

9. Aldimine formula (I) according to one of claims 1 to 5, characterized in that a represents the residue of an amine selected from the group consisting of N-methyl-1,2-academia, N-ethyl-1,2-academia, N-cyclohexyl-1,2-academia, N-methyl-1,3-propandiamine, N-ethyl-1,3-propandiamine, N-butyl-1,3-propandiamine, N-cyclohexyl-1,3-propandiamine, 4-aminomethylpyridine, 3-(4-aminobutyl)piperidine, Diethylenetriamine (DETA), dipropylenetriamine (DPTA), bisexualchristian (VNMC), fatty diamines, such as N-cocoalkyl-1,3-propandiamine, N-oleyl-1,3-propandiamine, N-coulcil-1,3-propandiamine and N-tallowalkyl-1,3-propandiamine, 5-amino-1-pentanol, 6-amino-1-hexanol, 4-(2-amino-ethyl)-2-hydroxyethylbenzene, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 2-(2-aminoethoxy)ethanol, triethylene glycol-monoamine, 3-(2 hydroxyethoxy)Propylamine, 3-(2-(2-hydroxyethoxy)ethoxy)Propylamine and 3-(6-hydroxyhexyloxy)Propylamine.

10. Aldimine formula (I) according to one of claims 1 to 5, characterized in that a represents the residue of an amine selected from the group consisting of 1,6-diamine, 1,5-diamino-2-methylpentane (MPMD), 1,3-pentanediamine (DAMP), 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (=ISOPHORONEDIAMINE or ACCESSORIES>), 2,2,4 - and 2,4,4-trimethylhexamethylenediamine (TMD), 1,3-xylylenediamine, 1,3-bis(aminomethyl)cyclohexane, bis(-aminocyclohexane)methane, bis(4-amino-3-methylcyclohexyl)methane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane, 1,2-, 1,3 - and 1,4-diaminocyclohexane, 1,4-diamino-2,2,6-trimethylcyclohexane, 3,6-dioxaoctyl-1,8-diamine, 4,7-dioctadecyl-1,10-diamine, 4-aminomethyl-1,8-octanediamine and polyoxyalkylene with two or three amino groups, and mixtures of these amines.

11. Aldimine formula (IX)

retrieved from aldimine formula (I) according to one of claims 1 to 10 by protonation or alkylation,
where R10means a hydrogen atom or alkyl, cycloalkyl or arylalkyl residue with 1-20 carbon atoms;
X2means O or S or N-R11or N-R7;
R11either means monovalent hydrocarbon residue with 1-20 carbon atoms, which, if necessary, contains at least one group of the ether carboxylic acid, a nitrile group, a nitro-group, group, ester phosphonic acid, alphagroup or ether sulfonic acids,
either means the Deputy of the formula (IX')

12. Containing antiminority connection AV, produced by the interaction of at least one aldimine formula (I) according to claim 1, with m=1, in particular at least one aldimine formula (Ia)at least one compound D containing at least one reactionsto the one group, which can react joining with a group of NC aldimine formula (I)and compound D is selected from Monomeric polyisocyanates and containing more than one isocyanate group of products of interaction of polyisocyanates with polyols.

13. Containing antiminority connection AV in item 12, characterized in that the reactive group of the compound D is selected from the group consisting of isocyanate groups.

14. Containing antiminority connection AV in item 12 or 13, characterized in that it is a containing antiminority connection VI formula (X)

where u represents 0 or 1, or 2, or 3, or 4, or 5,
v means 1 or 2 or 3 or 4 or 5 or 6,
provided that the sum (u+v) is 2 or 3, or 4, or 5, or 6;
Q means the residue containing (u+v) isocyanate groups MDI after removal of all isocyanate groups.

15. Containing antiminority the AV connection on 14, characterized in that it contains (u+v) isocyanate groups of the polyisocyanate is containing isocyanate groups of the polyurethane polymer PUP, which is obtained by reacting at least one polyol with at least one polyisocyanate.

16. Containing antiminority the AV connection on 14, characterized in that it contains (u+v) isocyanate groups of the polyisocyanate which m is a polyisocyanate PI in the form of a Monomeric diisocyanate, or a derivative of a Monomeric diisocyanate, in particular, is a derivative of 1,6-hexamethylenediisocyanate (HDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl (=isophorondiisocyanate or IPDI), 2,4 - and 2,6-toluylene diisocyanate and any mixtures of these isomers (TDI)and 4,4'-, 2,4'- and 2,2'-diphenylmethanediisocyanate and any mixtures of these isomers (MDI).

17. Curable composition containing at least one aldimine according to one of claims 1 to 11.

18. Curable composition according to 17, characterized in that it is a two-component composition consisting of component K1, containing at least one polyisocyanate, and component K2, containing at least one aldimine formula (I) according to claim 1.

19. The cured composition obtained by the reaction-curable composition according to one of PP-18 and water, in particular, in the form of moisture in the air.

20. Application aldimine according to one of claims 1 to 11 in adhesives, sealants, casting masses, coatings.

21. The product containing curable composition according to one of p, 18.

22. The product according to item 21, wherein the product is a structure, in particular the construction of aboveground or underground structures, or industrial product, or a consumer product, in particular a window, a household car, or vehicle, in particular water or on the roadways to the vehicle, preferably, car, bus, truck, or ship, or assembling parts of the vehicle, or an item of furniture, textile or packaging industry.



 

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SUBSTANCE: disclosed material contains the following components, wt %: inorganic fibre 20-40, rubber 3-12, low-molecular weight polyisobutylene 0.1-1.0 and foamed vermiculite with packed density of 28-80 g/l, obtained by treating the starting vermiculite with hydrogen peroxide with concentration of not less than 35% - the balance. Also disclosed is a method of producing said material, wherein foamed vermiculite is mixed with inorganic fibre and water to obtain a first mixture. The rubber and the low-molecular weight polisobutylene are then mixed to obtain a second mixture. The first and second mixtures are mixed to obtain a mixture from which the material is formed.

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FIELD: chemistry.

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FIELD: chemistry.

SUBSTANCE: present invention relates to a curable composition consisting of two components K1 and K2, which contain (a) at least one aromatic polyisocyanate P, which contains isocyanate groups, (b) at least one dialdimine A of formula , where X is a diamine residue DA with two primary amino groups after separating said two amino groups; and Y1 and Y2 are independently a univalent hydrocarbon residue with 1-12 C atoms; and Y3 is a univalent hydrocarbon residue which optionally has at least one heteroatom, particularly oxygen in form of an ether, a carbonyl or ester group, and (c) compounds which are reactive with respect to isocyanate groups, particularly water and/or polyols and/or polyamines, under the condition that at least one of the two primary amino groups of diamine DA is an aliphatic amino group, and that two primary amino groups of diamine DA differ from each other either by the number of hydrogen atoms at the carbon atoms (Cα), which are in the α-position to the corresponding amino group, at least one, or the number hydrogen atoms at the carbon atoms (Cβ), which are in the β-to the corresponding amino group, at least two. Described also is a curable composition obtained after reacting said composition with water, use of the disclosed compositions as an adhesive, a sealant, filling compound or coating, methods of gluing, sealing and coating using said curable composition, and an article which is glued, sealed or coated using said methods.

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23 cl, 10 tbl, 24 ex

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26 cl, 3 dwg, 7 tbl, 2 ex

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1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to particles, such as microparticles, and compositions, such as coating compositions and sealing compositions, which contain such particles. Disclosed is a particle whose outer surface is coated with a thin coating having film thickness of less than 25 mcm, wherein the (I) the thin coating contains a reaction product of (a) an aminoplastic resin and (b) a compound containing functional groups which are reactive with respect to the aminoplastic resin; or (II) the thin coating contains a sulphur-containing polymer. The compound (b) or sulphur-containing polymer contains thiol groups (polythiol, dithiol). The particle is a lightweight particle having specific weight of not more than 0.7 g/cm3 before applying the thin coating. The sulphur-containing polymer is a reaction product of the aminoplastic resin and a polyol, which preferably contains dithiol. The invention also relates to a method of using the particles, which involves adding the particles to a composition containing a binder in which the particles are dispersed. The invention also relates to a composition containing (a) a sulphur-containing polymeric binder; and (b) lightweight particles having specific weight of not more than 0.7 g/cm3 before applying the thin coating which are dispersed in the binder. The composition has specific weight of less than 1.0 or less than 0.9 or less than 0.85 g/cm3 and after deposition onto a substrate and curing turns into a curable composition which is characterised by: (i) swelling value of not more than 40 vol. % after immersion for one week at 140°F and ambient pressure in jet reference fluid (JRF) type 1; (ii) an elongation of at least 80% when measured according to AMS 3269a; and (iii) tensile strength of at least 2000 MPa when measured according to AS 5127/1a 7.7. The invention also relates to an aerospace vehicle having at least one slit sealed by a sealant made from said composition.

EFFECT: obtaining a composition which is capable of forming a film having resistance to weather elements such as moisture and temperature, and at least partially blocks such materials as water, fuel and other liquids and gases, and the curable sealant compositions have low temperature of elasticity and high tensile strength.

16 cl, 2 dwg, 4 tbl

FIELD: chemistry.

SUBSTANCE: method involves depositing an adhesive system onto one or more pieces of wood-based material and joining one or more pieces with one or more additional pieces of the material. The adhesive system contains one component which contains starch, and another component which contains one or more polymers belonging to a group comprising polyvinyl amine, copolymers poly(vinyl alcohol-co-vinyl amine), poly(vinyl alcohol-co-vinyl formamide), polyallyl amine, polyethylene imine, polyamido amine and polyvinyl formamide. The two components are deposited on the wood-based material as unmixed separate components. The adhesive system further contains one or more polymers containing acetoacetylated polyvinyl alcohol.

EFFECT: use of the adhesive system enables to produce such wood-based products as boards based on chips, particles or fibres or boards based on aligned long chips.

19 cl, 1 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to aldimines of formula (I)

where A does not contain active hydrogen and a primary amine group, or together with R7 denotes a (n+2)-valent hydrocarbon radical containing 3-20 carbon atoms and, if necessary, at least one heteroatom in form of oxygen of an ether group or nitrogen or a tertiary amine group; n equals 1, 2, 3 or 4; m equals 0,1, 2, 3 or 4; R1 and R2 each denotes a univalent hydrocarbon residue with 1-12 carbon atoms or together denote a divalent hydrocarbon radical which is part of a carbocyclic ring with 5-8 carbon atoms; R3 denotes H or alkyl; R4 and R5 independently denote CH3 or a univalent aliphatic radical containing 2-12 carbon atoms and optionally hydroxy groups; X denotes O, S, N-R6, or N-R7, where R6 denotes a univalent hydrocarbon radical containing 1-20 carbon atoms and having at least one hydroxy group; as well as curable compositions containing such aldimines and use of said compositions.

EFFECT: obtaining novel aldimines which can be used as curing agents in curable compositions.

22 cl, 18 ex, 6 tbl

FIELD: chemistry.

SUBSTANCE: composition contains one or more urethane prepolymers, having isocyanate residues, one or more compounds which catalyse the reaction of isocyanate residues with water or a compound which contains active hydrogen and one or more alpha-hydrocarbyl silane compounds. The urethane propolymer additionally contains a silane functional group. The composition additionally contains a compound or a polymer, containing silane residues. The composition additionally contains one or more compounds which catalyse silanol condensation. The composition is deposited onto the surface of glass or plastic with a coating or onto the surface of a substrate to obtain a sealant, then brought into contact and the composition is then hardened. The composition is placed between the glass or plastic with coating and the substrate. The sealing composition is used for binding an unprimed surface with a coating, such as a window lintel with glass with a transparent plastic, coated with an abrasive-resistant coating or with glass or plastic with a coating, additionally coated with glass cement, such as ceramic or organic glass cement.

EFFECT: improved composition properties.

10 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: method of gluing involves processing the surfaces to be glued, applying the glue, pressing the components together and solidification of the glue. The glued surfaces are processed through external heating of the glued components until formation of a 0.5-2.0 mm deep coked layer. The glue joint works at temperature conditions at which material of one or both of the components undergoes thermal decomposition.

EFFECT: method improves adhesion characteristics of gluing carbon fibre reinforced plastic, as well as other composites with heat-resistant filler, increases reliability of operation, particularly glued heat shielding of sockets and reduces their weight.

1 tbl, 2 dwg

FIELD: process engineering.

SUBSTANCE: invention relates to woodworking. Proposed method comprises pressing the stack of two or more boards wherein every board has surface layer and base layer. Surface layer side stays in contact with base layer side. Aforesaid sides in contact have fast-curing glue arranged there between that comprises(a) emulsion polymer selected from the group consisting of latex of butadiene-styrene rubber, latex of modified butadiene-styrene rubber, polyvinyl acetate, ethylene vinyl acetate and combination thereof, and (b) cross-linking compound. Pressing consist in application of uniform pressure to the stack, perpendicular to its surface, at ambient temperature for time equal to, at least 0.1 min, without hot pressing.

EFFECT: pressing of wood lamina materials at ambient temperature using glues not containing formaldehydes.

19 cl, 12 ex, 3 tbl, 3 dwg

FIELD: chemistry.

SUBSTANCE: invention can be used in rubber industry to make rubber-metal articles, particularly water-resistant articles used at high temperatures (up to 90°C). The invention relates to a method of gluing rubber to metal through a cold curing method, which involves applying a layer of glue onto a processed metal surface. Rubber is glued to the metal using a ternary adhesive composition: a first layer of Chemosil 211 glue is applied onto a processed metal surface and dried, a second layer of Chemosil 221 or Chemosil 222 glue is applied on the first layer and dried, and two layers of 88 KR glue are applied on each processed metal and rubber surfaces, drying each of the layers and then gluing the surfaces.

EFFECT: higher bonding strength of polar raw rubber-based rubber with a metal alloy while maintaining high adhesiveness and adhesion strength when the article is used in water at high temperatures.

2 cl, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of gluing vulcanised rubber to each other and can be used in rubber industry. The method of gluing different types of vulcanised rubber to each other involves application of polychloroprene rubber based glue onto vulcanised rubber surfaces to be glued and then bringing the surfaces into contact. The base of the polychloroprene glue used is nairit NT or nairit DP combined with butyl phenolformaldehyde resin in 88NT or 88SA adhesive. Before application onto the surface, the adhesive is mixed with a trichloroethylphosphate or trichloropropylphosphate modifier in amount of 0.05-2.0 pts. wt per 100 pts. wt of the adhesive, and after application, the adhesive film is dried at room temperature for 1-2 minutes and the surfaces to be glued are brought into contact under a load for 24 hours.

EFFECT: increased strength of the glue joint when gluing vulcanised rubber and simplification of the gluing process.

2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: method of gluing vulcanised rubber of the same type to each other involves depositing glue based on polychloroprene rubber on the surfaces to be glued and subsequently bringing the surfaces into contact. 88NT or 88SA glue based on polychloroprene rubber nairite NT or nairite DP combined with butylphenol formaldehyde resin is used. Before depositing the glue onto the surface, a modifier which is ortho-phenylenediamine is added to the glue in amount of 0.5-3.0 pts. wt per 100 pts. wt of glue, and after deposition, the glue film is dried at room temperature for 1-2 minutes. The glued surfaces are brought into contact under a load for 24 hours. Rubber based on SKI-3, SKEPT-40, SKN-18 and neoprene is glued.

EFFECT: increased strength of the glue joint when gluing vulcanised rubber and simplification of the gluing process.

2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: method of bonding vulcanised rubber of the same type to each other involves depositing glue based on polychloroprene rubber on the surfaces to be glued together, as well as 88NT or 88SA glue based on polychloroprene rubber nairite NT or nairite DP combined with butylphenol formaldehyde resin. Before depositing onto the surface, a modifier which is paraoxydiphenylamine is added to the glue in amount of 0.3-4.0 pts. wt per 100 pts. wt of glue, and after depositing, the glue film is dried at room temperature for 1-2 minutes, and the surfaces are brought into contact under a load for 24 hours. Rubber based on SKI-3, SKEPT-40, SKN-18M and neoprene AS is glued together.

EFFECT: increased strength of the glued joint when gluing vulcanised rubber of the same type, simplification of the gluing process.

2 tbl, 2 ex

FIELD: technological processes.

SUBSTANCE: synthetic glue is applied on the surface of parts from wood materials, glued surfaces are joined until glue hardens completely, at that glued parts are located between plates of electrostatic field capacitor so that power lines of electrostatic field are directed perpendicular to glue line and treated in electrostatic field with intensity of 2.16-9.5·102 V/cm, and glue applied on glued surfaces is polyvinyl acetate PVAC or epoxy K-153.

EFFECT: higher strength of glued connections of wood materials and higher speed of glue line hardening.

2 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to a curable composition consisting of two components K1 and K2, which contain (a) at least one aromatic polyisocyanate P, which contains isocyanate groups, (b) at least one dialdimine A of formula , where X is a diamine residue DA with two primary amino groups after separating said two amino groups; and Y1 and Y2 are independently a univalent hydrocarbon residue with 1-12 C atoms; and Y3 is a univalent hydrocarbon residue which optionally has at least one heteroatom, particularly oxygen in form of an ether, a carbonyl or ester group, and (c) compounds which are reactive with respect to isocyanate groups, particularly water and/or polyols and/or polyamines, under the condition that at least one of the two primary amino groups of diamine DA is an aliphatic amino group, and that two primary amino groups of diamine DA differ from each other either by the number of hydrogen atoms at the carbon atoms (Cα), which are in the α-position to the corresponding amino group, at least one, or the number hydrogen atoms at the carbon atoms (Cβ), which are in the β-to the corresponding amino group, at least two. Described also is a curable composition obtained after reacting said composition with water, use of the disclosed compositions as an adhesive, a sealant, filling compound or coating, methods of gluing, sealing and coating using said curable composition, and an article which is glued, sealed or coated using said methods.

EFFECT: obtaining moisture-curable polyurethane compositions which are stable during storage, are characterised by long curing time before gluing and high rate of hardening and harden without bubbles.

23 cl, 10 tbl, 24 ex

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