Moisture-curable polyurethane compositions containing aldimine-containing compounds

FIELD: chemistry.

SUBSTANCE: invention relates to a moisture-curable composition for adhesive compounds, sealing compounds, coatings or linings, application thereof as an adhesive, sealing compound or coating, a cured composition obtained by reacting water with such a composition, methods of gluing bases and sealing using said composition, as well as adhesive and sealed articles made using said methods, respectively. The moisture-curable composition contains (i) at least one isocyanate-containing polyurethane polymer P, which is obtained from at least one polyisocyanate and at least one polyol, and (ii) at least one aldimine-containing compound of formula (I): .

EFFECT: preparation of compounds which are stable during storage, can be quickly moisture-cured without bubbles, do not cause smells during curing and are suitable for use as precursors of synthetic materials.

25 cl, 34 ex, 10 tbl

Description

The technical field

The invention relates to the field of aldimines and moisture curing polyurethane polymers.

The level of technology

Polyurethane compositions are precursors to synthetic materials, which for a long time are used, for example, as adhesives, sealants, coatings and linings. Usually they include containing isocyanatomethyl polymer derived from polyols and polyisocyanates, which are mixed with other components and to the application stored in the absence of moisture. This song is called one-component composition, it cures when exposed to moisture on a synthetic material. These in themselves known systems have the disadvantage that when they are curing, followed by the release of carbon dioxide (CO₂) the reaction of isocyanate groups with water, the cured synthetic material can begin the formation of undesirable gas bubbles; this happens in particular when the curing rate is high. To suppress the formation of bubbles during curing isocyanatomethyl compositions in the composition can be added blocked amines, for example in the form of aldimines as a so-called "latent amines" or "latent hardeners". Upon contact with moisture blocked amino latent the of tergites hydrolyzed and then react with the isocyanate groups of the composition without allocation of CO ₂. The use of aldimines as latent hardeners in isocyanatomethyl composica described, for example, in patent US 3420800. However, the presence aldimine fraught with the danger that the composition due to the outbreak of premature reaction between alliminum and isocyanate groups will be stable when stored for only a short time or it might not be stable.

Known for containing aldimine composition based on isocyanates, distinguished by good storage stability, as, for example, described in documents US 4469831, US 4853454 and US 5087661. In document WO 2004/013200 A1 describes containing polyamideimide compositions, which are stable in storage and which, if moisture otverzhdajutsja odorless. The composition described in the above publications have the disadvantage that they are for curing relatively a lot of water, which is twice more than in the case when present in the composition isocyanatomethyl polyurethane polymer cures without latent hardener, i.e. in the direct reaction of isocyanate groups with water. In the case of curing with moisture of the air composition hardens from outside to inside, and the water required for the curing reaction must diffuse through becoming thicker layer of synthetic material; therefore, the availability of water, especially when the use of the drop of thick layers of the composition, becomes the limiting factor already after a short time of reaction curing. Therefore, increased consumption of water leading to the curing of the crosslinking reactions automatically leads to slower curing.

Isocyanatobenzene compositions which require curing less water than the system described above, is known. So, in patents US 4108842, US 4404379 and US 6136942 describes compositions which contain reaction products of polyisocyanates and amidofunctional of aldimines, or cyclonically as their tautomeric forms, and which quickly otverzhdajutsja adding moisture and can be applied, for example, as adhesives, sealants or coatings. However, the composition described in the above-mentioned publications, have poor stability during storage. This is due to the fact that they contained a protected amino group, in the form of alvinovich or cyclonically groups do not remain completely inert towards isocyanate groups, and slow to respond to them, particularly with reactive aromatic isocyanate groups, in the absence of moisture, and thereby cause an increase in viscosity, which already after a short time can make the composition unusable. In addition, when applying the compositions have an unpleasant smell due to the emitted during curing (as a result of hydrolysis alvinegro) aldehydes, and so are limitedly applicable, especially in the interior of the applicable limited. In addition, compositions according to the US 6136942 in utverzhdenii form have problems with lightfastness.

Detailed description of the invention

In this regard, the present invention is to develop compositions that are stable during storage, quickly and without bubbles otverzhdajutsja with the introduction of moisture during curing does not cause the formation of odor and are suitable as precursors of synthetic materials. It was unexpectedly found that this problem is solved eliminatorias connection on p. 1 of the claims.

These compositions have excellent storage stability. Adding moisture they quickly otverzhdajutsja without the formation of bubbles and odorless. They are suitable as precursors of synthetic materials, in particular for use as adhesives, sealants, coatings and linings, which can also be used in applications involving no odor, such as bonding, sealing, coating or flooring inside vehicles or buildings, and which have very good properties, in particular, high early strength. Other forms of implementation are subject to the following independent claims. Other advantageous form of implementation, the image is etenia emerge from the dependent claims.

Ways of carrying out the invention

The object of the invention are compositions that include at least one containing isocyanatomethyl the polymerPand at least one eliminatorias compound of formula (I). This isocyanatomethyl polyurethane polymerPobtained from at least one MDI and at least one polyol.

In the formula (I), m denotes an integer from 1 to 4, p is an integer from 1 to 6, and q denotes an integer from 0 to 5, with the proviso that the sum of p and q is from 2 to 6. Further, R¹means any monovalent hydrocarbon residue with 6-30 C atoms, which may contain at least one heteroatom, in particular in the form of a simple oxygen of the ether, or R¹means the Deputy of the formula (II).

Thus R⁶means a divalent hydrocarbon residue with 2 to 20 C atoms, which may contain at least one heteroatom, in particular in the form of a simple oxygen ether. R⁷means monovalent hydrocarbon residue with 1-20 atoms C.

Further, R²and R³mean either two independent from each other Deputy, who represent a monovalent hydrocarbon residue with 1 to 12 C atoms, or R²and R³the place constitute the only Deputy, represents a divalent hydrocarbon residue with 4 to 20 C atoms, which is part of a carbocyclic ring with 5 to 8, preferably 6 atoms C. This carbocyclic ring may in any case be substituted.

Further, R⁴means (m+1)-valent hydrocarbon residue with 2 to 12 C atoms, which may contain at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen.

Further, R⁵means either (p+q)-valent organic residue (the residue may contain heteroatoms and may be obtained by removing (p+q) NCO-groups of R⁵-[NCO]_p+qor R⁵means N, NR¹⁴, O, OC(O)O, Si, P(O)O₃or SO₂. Thus R¹⁴means monovalent hydrocarbon residue with 1-20 atoms C.

In addition, X represents O, S or N-R⁸and here R⁸means any monovalent hydrocarbon residue with 1-20 C atoms, which may contain at least one group of ester of carboxylic acid, a nitrile, a nitro-group, a group of ester phosphonic acid, sulfonic group or the group of ester sulfonic acid or means the Deputy of the formula (III).

The dotted line in formulas indicate connection with the above substituents.

Containing aldimine connected to the e of the formula (I) can be obtained by reaction of at least one aldimine formula (XI), containing active hydrogen, with at least one polyisocyanateD. When this bearing active hydrogen reactive group aldimine formula (XI) is reacted in the reaction of joining with one or more isocyanate groups MDIDwith the formation of eliminatorias the compounds of formula (I), hereinafter also called the "product of accession". The term "active hydrogen" in this document means capable of deprotonation of the hydrogen atom linked to the nitrogen atom, oxygen or sulfur. The term "reactive group containing active hydrogen"means a functional group bearing an active hydrogen, in particular primary or secondary amino group, hydroxyl group, mercaptopropyl or group of urea. These distinctive properties of substances, as eliminatethe" or "isocyanatomethyl"indicates that these substances are specified functional groups, i.e. aldimine group or isocyanate group. The prefix "poly" in the designation of substances, for example, "polyamidimide", "polyamine, polyisocyanate or polyol" in this document indicates that the corresponding substance is formally molecule contains more than one functional group which brought his name.

R¹, R^{2 , R3, R4and X and m have the meanings already described for containing aldimine the compounds of formula (I).}

Aldimine formula (XI) can be obtained from at least one sterically constrained aliphatic aldehydeAand at least one aliphatic amineBcorresponding to the formula [H₂N]_m-R⁴-XH, which, along with one or more primary amino groups includes another reactive group containing active hydrogen.

The interaction between the aldehydeAand AminBoccurs in the condensation reaction with elimination of water. Such condensation reaction is well known and is described, for example, in Houben-Weyl, "Methods der organischen Chemie", Vol. XI/2, page 73ff. This aldehydeAused in stoichiometric amount or in a stoichiometric excess in relation to the primary amino groups AminB. Usually such the condensation reaction is conducted in the presence of a solvent, whereby formed during the reaction, water is diverted azeotrope. However, for aldimines formula (XI) is the preferred way to obtain without the use of solvents, and formed by condensation water is drained from the reaction mixture directly by application of vacuum. Upon receipt in the absence of solvent becomes unnecessary Stripping of the solvent on okoncane the receipt, that simplifies the process of obtaining. In addition, this aldimine has no residual solvent, which could be the cause of odor.

To obtain aldimine formula (XI) used at least one sterically hindered aliphatic aldehyde A formula (IV).

In the formula (IV) R¹, R²and R³have the same value as what is described for formula (I).

AldehydeAhas no smell. Under the substance "unscented" means a substance that has such a weak smell, that it is for most people imperceptible, that is not perceived by the nose.

AldehydeAget, for example, from carboxylic acids R¹-COOH and β-hydroxyaldehyde formula (V) in the esterification reaction. This esterification can be carried out by known methods described, for example, in Houben-Weyl "Methods der organischen Chemie", Vol. VIII, p. 516-528. β-Hydroxyaldehyde formula (V) are obtained, for example, in the cross-aldol condensation of formaldehyde (or oligomeric forms of formaldehyde as paraformaldehyde or 1,3,5-trioxane) and the aldehyde of formula (VI).

In formulas (V) and (VI) R²and R³shall have the same meaning as described for formula (I).

Obtaining aldehydeAis carried out preferably without solvent. While β-hydroxyaldehyde formula (V) and without the use of solvents is directly in the reaction with carboxylic acid, and formed by the esterification of the water is removed in vacuum. In addition, it is preferable to carry out the aldol condensation and esterification leading to the aldehydeA,from the source materials in a common process step, for example, in one reactor.

Suitable carboxylic acids R¹-COOH for the esterification of β-hydroxyaldehyde formula (V) should be mentioned, for example, the following: saturated aliphatic carboxylic acids, such as enanthic acid, Caprylic acid, pelargonia acid, capric acid, undecanoate acid, lauric acid, tridecanoate acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachnid acid; monounsaturated aliphatic carboxylic acids, as palmitoleic acid, butyric acid, erucic acid; polyunsaturated aliphatic carboxylic acid, linoleic acid, linolenic acid, liquid, stearic acid, arachidonic acid; cycloaliphatic carboxylic acids, such as cyclohexanecarbonyl acid; arylaliphatic carboxylic acid, as phenylacetic acid; aromatic carboxylic acids as benzoic acid, naphthoic acid, tolarova acid, anisic acid; isomers e is their acid; mixtures of fatty acids obtained from technical saponification of natural oils and fats, such as rapeseed oil, sunflower oil, linseed oil, olive oil, coconut oil, oil from the seeds of the oil palm and palm oil; and complex monoalkylamines and arrowie esters of dicarboxylic acids, which are obtained by simple esterification of dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, Emelyanova acid, cork acid, azelaic acid, sabotinova acid, 1,12-dodecandioic, maleic acid, fumaric acid, hexahydrophthalic acid, hexahydrophthalic acid, hexahydroterephthalate acid, 3,6,9-trioxadecyl, and similar derivatives of polyethylene glycol, alcohols such as methanol, ethanol, propanol, butanol, and higher homologs and isomers of these alcohols.

Preferred are Caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, butyric acid, linoleic acid, linolenic acid, isomers of these acids, as well as technical mixtures of fatty acids that contain these acids. Especially preferred lauric acid.

Suitable aldehydes of the formula (VI) to react with formaldehyde to obtain β-d is toxilogical formula (V) are for example, Isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, 2-methylvaleraldehyde, 2-ethylcapronaldehyde, cyclopentanecarboxaldehyde, cyclohexanecarboxaldehyde, 1,2,3,6-tetrahydrobenzaldehyde, 2-methyl-3-phenylpropionaldehyde, 2-phenyl-Propionaldehyde and diphenylacetaldehyde. Preferred Isobutyraldehyde.

Suitable β-hydroxyaldehyde formula (V) are, for example, reaction products of formaldehyde with aldehydes of the formula (VI)above as appropriate. Preferred 3-hydroxybenzaldehyde.

AminBis an aliphatic amine, which in addition to one or more primary amino group also includes another reactive group containing active hydrogen. In this document the term "primary amino group" means the NH₂the group, which is associated with organic residue, and the term "secondary amino group" means an NH-group, which is associated with two organic residues. The term "aliphatic amine" refers to compounds that contain at least one amino group that is associated with aliphatic, cycloaliphatic or arylaliphatic balance. Thus, they differ from aromatic amines in which the amino group is directly linked to an aromatic residue, such as, for example, in aniline or 2-aminopyridine.

Of the aminesBsuitable, for example, hereinafter called the connection:

- aliphatic hydroxyamine as 2-aminoethanol, 2-methylaminoethanol, 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-trimethyl-cyclohexanol; bearing a primary amino derivatives of glycols as diethylene glycol, dipropyleneglycol, dibutylamino and higher oligomers and polymers of these glycols, for example, 2-(2-aminoethoxy)-ethanol, triethylene glycol monoamine, α-(2-hydroxymethylene)-ω-(2-aminomethylated)-poly(oxymethyl-1,2-ethandiyl); bearing a hydroxyl group and one or more primary amino groups derived polyalkoxysiloxanes three - or polynuclear alcohols or polyalkoxysiloxanes diamines; products simple cyanoethylidene and subsequent hydrogenation of glycols, for example, 3-(2-hydroxyethoxy)-Propylamine, 3-(2-(2-hydroxyethoxy)-ethoxy)-Propylamine, 3-(6-hydroxyhexyloxy)-Propylamine;

- aliphatic mercaptamine as 2-aminoethanethiol (tsistamin), 3-aminopropanol, 4-amino-1-butanethiol, 6-amino-1-hexanethiol, 8-amino-1-octanethiol, 10-amino-1-decanter, 12-amino-1-dodecanethiol; amenitieshere as 2-amino-2-deoxy-6-thioglucose;

two - or polynuclear aliphatic amines, which in addition to one the or more primary amino groups are secondary amino group, 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-amandemen, 4-aminomethyl-piperidine, 3-(4-aminobutyl)-piperidine, N-AMINOETHYLPIPERAZINE, Diethylenetriamine (DETA), bis-hexamethylendiamine (BHMT); di - and triamine received by cyanoethylidene or cyanobutane 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-pentylamine, 3-(2-ethylhexyl)amino-1-pentylamine, 3-dodecylamino-1-pentylamine, 3-cyclohexylamino-1-pentylamine, dipropylenetriamine (DPTA), N3-(3-AMINOPHENYL)-1,3-pentadien, N5-(3-aminopropyl)-2-methyl-1,5-pentadien, N5-(3-amino-1-ethylpropyl)-2-methyl-1,5-pentazemin, and fatty diamines, as the N-cocoalkyl-1,3-propandiamine, N-oleyl-1,3-propandiamine, N-soya-alkyl-1,3-propandiamine, N-tallowalkyl-1,3-propandiamine or N-(C_16-22-alkyl)-1,3-propandiamine which can be purchased, for example, under the trademark Duomeen^®from Akzo Nobel; the products obtained by joining Michael at a molar ratio of 1:1 aliphatic primary di - or polyamines to Acrylonitrile, complex diesters maleine is Oh or fumaric acid, esters tarakanovas acid, esters of acrylic and methacrylic acid and esters basis of itaconic acid;

three times substituted urea, which contain one or more primary amino groups as N-(2-amino-ethyl)-etilenmocevina, N-(2-amino-ethyl)-propylenimine or N-(2-amino-ethyl)-N'-metalmachine.

Particularly suitable aliphatic hydroxy - and mercaptoamines are those in which the primary amino group separated from the hydroxyl or mercaptopropyl chain of at least 5 atoms, or ring, as, for example, 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, 2-(2-aminoethoxy)-ethanol, triethylene glycol monoamine, α-(2-hydroxymethylene)-ω-(2-aminomethylated)-poly(oxymethyl-1,2-ethandiyl), 3-(2-hydroxyethoxy)-Propylamine, 3-(2-(2-hydroxyethoxy)-ethoxy)-Propylamine, 3-(6-hydroxyhexyloxy)-Propylamine, 6-amino-1-hexanethiol, 8-amino-1-octandiol, 10-amino-1-decandiol and 12-amino-1-dodecanthiol.

As aminesBthe preferred two - or polyvalent aliphatic amines, which in addition to one or more primary amino groups contain a secondary amino group, in particular N-methyl-1,2-amandemen, N-ethyl-1,2-amandemen, N-cyclohexyl-1,2-shall mandamin, 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. Preferable aliphatic hydroxy - and mercaptoamines, in which the primary amino group separated from the hydroxyl or mercaptopropyl chain of at least 5 atoms, or ring, 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 monoamine and higher oligomers and polymers, 3-(2-hydroxyethoxy)-Propylamine, 3-(2-(2-hydroxyethoxy)-ethoxy)-Propylamine and 3-(6-hydroxyhexyloxy)-Propylamine.

The reaction between the aldehydeAand AminBgoes with the formation of hydroxyarginine, if AminBused hydroxyamine; mercaptoethylamine, if AminBused mercaptamine; aminoalkenes, if AminBuse two or polynuclear amines, which in addition to one or more primary amino groups contains one or more secondary amino groups; or with the formation of mcevisualaid, if AminBthe use triply substituted urea, which contains one or more primary amine groups.

In one embodiment, the implementation aldimine formula (XI) contain the N substituents-R⁸as Deputy X. Such aldimine formula (XI) can be obtained, resulting in the first stage, at least one sterically hindered aliphatic aldehydeAformula (IV) reaction with at least one two - or polynuclear aliphatic primary amineCformula [H₂N]_m-R⁴-NH₂with the formation of an intermediate product of the formula (VII), which in addition one or more alvinovich group also contains one primary amino group, and then the second step is bringing this intermediate product in the reaction of joining with a Michael acceptor of the formula (VIII) with respect to the number of double bonds among the NH_2-groups of 1:1. This produces aminoalkyl, which, along with one or more alliminum groups also contains at least one, preferably exactly one, a secondary amino group.

In the formula (VII) m, R¹, R², R³and R⁴have the same values as what is described for formula (I).

As a result of this form aldimine formula (XI)in which X represents residues N-R⁸and R⁸is a monovalent hydrocarbon ostad the m formula (IX) or (IX'). In formulas (VIII), (IX) and (IX') R⁹means the residue that is selected from the group consisting of-COOR¹³, -CN, -NO₂, -PO(OR¹³)₂, -SO₂R¹³and-SO₂OR¹³and R¹⁰means a hydrogen atom or a residue from the group consisting of-R¹³, -COOR¹³and-CH₂COOR¹³, R¹¹and R¹²independently from each other mean a hydrogen atom or a residue from the group consisting of-R¹³, -COOR¹³and-CN, and R¹³means monovalent hydrocarbon residue with 1-20 atoms C.

AminCis an aliphatic amine with at least two primary amino groups.

Examples of suitable aminesCare aliphatic polyamine, such as Ethylenediamine, 1,2 - and 1,3-propandiamine, 2-methyl-1,2-propandiamine, 2,2-dimethyl-1,3-propandiamine, 1,3 - and 1,4-butanediamine, 1,3 - and 1,5-pentanediamine, 2-butyl-2-ethyl-1,5-pentadien, 1,6-hexamethylenediamine were (HMDA), 2,2,4 - and 2,4,4-trimethylhexamethylenediamine and their mixtures (TMD), 1,7-heptadien, 1,8-octanediamine, 2,4-dimethyl-1,8-octanediamine, 4-aminomethyl-1,8-octanediamine, 1,9-enantiomer, 2-methyl-1,9-enantiomer, 5-methyl-1,9-enantiomer, 1,10-decontamin, isodecanoate, 1,11-undecanedioic, 1,12-dodecandioic, methyl-bis-(3-aminopropyl)amine, 1,5-diamino-2-methylpentane (MPMD), 1,3-diaminopentane (DAMP), 2,5-dimethyl-1,6-hexamethylenediamine were; cycloaliphatic polyamine as 1,2-, 1,3 - and 1,4-diaminocyclohexane, the IP-(4-aminocyclohexane)-methane (H ₁₂MDA), 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-methylcyclohexyl)-methane (M-MECA), 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (= ISOPHORONEDIAMINE, or ACCESSORIES>), 2 - and 4-methyl-1,3-diaminocyclohexane and their mixtures, 1,3 - and 1,4-bis-(aminomethyl)cyclohexane, 1,3,5-Tris-(aminomethyl)-cyclohexane, 1-cyclohexylamino-3-aminopropane, 2,5(2,6)-bis-(aminomethyl)-bicyclo[2.2.1]heptane (NBDA, production Mitsui Chemicals), 3(4),8(9)-bis-(aminomethyl)-tricyclo[5.2.1.0^2,6]decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane; arylaliphatic polyamine as 1,3-xylylenediamine (MXDA), 1,4-xylylenediamine (PXDA), 1,3,5-Tris-(aminomethyl)benzene, aliphatic polyamine containing a group of simple ether, such as a simple bis-2-aminoethylamide ether, 4,7-dioctadecyl-1,10-diamine, 4,9-dioxadodecane-1,12-diamine and higher oligomers; polyoxyalkylene with two theoretically or three amino groups, available in the sale, for example under the name Jeffamine^®(production of Huntsman Chemicals). Preferred are di - or triamine, in which the primary amino groups separated by a chain of at least 5 atoms, or ring, 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-dodecane the Jamin, 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[5.2.1.0^2,6]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, 1,3,5-Tris-(aminomethyl)benzene, as well as polyoxyalkylene with theoretically two or three amino groups, sold, for example under the name Jeffamine^®(production of Huntsman Chemicals).

Examples of suitable Michael acceptors of the formula (VIII) are complex diesters of maleic or fumaric acid, as dimethylmaleic, diethylmalonate, dibutylamine, diethylfumarate; complex diesters tarakanovas acid, as dimethylcarbonate; esters of acrylic or methacrylic acid as methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, tetrahydrofuryl(meth)acrylate, isobornyl(meth)acrylate; complex diesters basis of itaconic acid, as dimethylethanol; esters of cinnamic acid, as methylcinnamic; complex diesters vinylphosphonic acid as dimethyl ether vinylphosphonic acid; ester vinylsulfonic acid, in particular arrowy ether vinylsulfonic acid; vinyls lfany; vigilantly as Acrylonitrile, 2-pentenenitrile or fumaronitrile; 1-nitroethylenes as β-nitrosothiol; and condensation products of knoevenagel, as, for example, derived from complex diesters of malonic acid and aldehydes, such as formaldehyde, acetaldehyde or benzaldehyde. Preferred complex fluids maleic acid, esters of acrylic acid, complex fluids phosphonic acid and vigilantly.

The interaction of the aldehydeAwith AminCwith the formation of an intermediate product of the formula (VII) occurs in the condensation reaction with elimination of water, as already described above for the interaction of the aldehydeAwith AminB. Thus the stoichiometry between the aldehydeAand AminCis chosen so that m moles of aldehydeAhad 1 mol amineC, which contains m+1 mol of primary amino groups. The preferred method of obtaining without solvent, and formed by condensation water is removed from the reaction mixture by application of vacuum.

Reaction of the intermediate product of the formula (VII) with a Michael acceptor of the formula (VIII) is conducted, for example, the fact that the intermediate product in a stoichiometric or slightly oversexualization number mixed with a Michael acceptor of the formula (VIII) and the mixture is heated to a temperature of from 20 to 110°C until complete conversion of the intermediate products which act in algemin formula (XI). The reaction is preferably carried out without solvents.

In certain cases aldimine formula (XI) can be in equilibrium with cyclic forms, which for example is shown by formula (X). These cyclic form in the case of aminoalkenes are cyclic aminase, as, for example, imidazolidin or tetrahydropyrimidin; in the case of hydroxyarginine - cyclic aminoacetate, as, for example, oxazolidin or tetrahydrooxazolo; in the case of mercaptoethylamine - cyclic thiaminase, as, for example, thiazolidin or tetrahydrothiophene.

In the formula (X) m, R¹, R², R³, R⁴and X have the same values as described for formula (I).

It was unexpectedly found that the majority of aldimines formula (XI) are not prone to cyclization. In particular, for aminoalkenes using the methods of IR - and NMR-spectroscopy it is possible to show that these compounds are mainly in the form of open circuits, i.e. in aliminosa form, while cyclical, meaning that analnye forms, are absent or are present only in trace quantities. This differs from the behavior of aminoalkenes corresponding to the prior art, which are described, for example, in US 4404379 and US 6136942: those are always predominantly in the form of cycloamylose. Also, hydroxy - and mercaptoamines, in which the s primary amino group separated from hydroxy, accordingly mercaptopropyl chain of at least 5 atoms, or ring, does not detect cyclization. The almost total absence of cyclic structures in aldimine formula (XI) should be regarded as an advantage, in particular from the point of view of their application in isocyanatomethyl compositions, so as thereby aldimine are inherently contained in aminullah, oxazolidine and thioamines basic nitrogen atoms, which may degrade the stability isocyanatomethyl composition during storage.

Aldimine formula (XI) are odorless. In suitable conditions, in particular with the exclusion of moisture, they are stable during storage. When moisture aldimine group of aldimines can be either hydrolyzed through an intermediate stage, formally, to the amino groups, and allocates the corresponding aldehydeAused to obtain aldimine. Since this hydrolysis reaction is reversible and the chemical equilibrium is markedly shifted towards aldimine, should proceed from the fact that in the absence of active amines groups partially or completely hydrolyzed only part alvinovich groups.

As MDIDsuitable two - or polynuclear Monomeric and/or oligomeric aliphatic, cycloaliphatic, arylaliphatic and aromatic polyisocyanates of the formula (XII),

as, for example, 1,6-hexamethylenediisocyanate (HDI), 2-methylpentanediol-1,5-diisocyanate, 2,2,4 - and 2,4,4-trimethyl-1,6-hexamethylenediisocyanate (TMDI), 1,12-dodecyltrimethoxysilane, lysine diisocyanate and 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-mesitylenesulfonic, dimeric and trimeric isocyanates fatty acids, as 3,6-bis-(9-isocyanatophenyl)-4,5-di-(1-heptenyl)-cyclohexan (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 (polymer 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 group; modi is these two - and polynuclear isocyanates, containing ester -, urethane-, biuret-, allophanate, carbodiimide, uretonimine, oxadiazoline group or urea group; and isocyanatobenzene polyurethane polymers, i.e. containing more than one isocyanate group of the reaction products of polyisocyanates with substances containing two or more hydroxyl groups (the so-called "polyols"), as, for example, two - or polynuclear alcohols, glycols or aminoalcohols, polyhydroxybutyrate ethers, polyesters, polyacrylates, polycarbonates or paleogeography, in particular, polyethers.

The interaction between aldimines formula (XI) and polyisocyanateDwith the formation of the product of accession, meet the formula (I), is carried out in known conditions, which are typically used for the reaction between the reactive groups involved in the relevant transformations, for example, at a temperature of from 20 to 100°C. the Reaction is carried out using a solvent or preferably without solvents. It is possible, may optionally be used excipients, such as, for example, catalysts, initiators or stabilizers. For aminoacidemia reaction is carried out preferably at room temperature without catalyst, hydroxy-, mercapto - and mcevisualaid - when temperature is from 40 to 100°C and using a catalyst, what is used for the reaction between isocyanates and alcohols to form urethanes, for example ORGANOTIN compound, a complex of bismuth, a tertiary amine compound or a combination of such catalysts.

If the response of the merger between aldimines formula (XI) and polyisocyanateDto obtain eliminatorias the compounds of formula (I) is carried out with stoichiometric proportions, i.e., one molar equivalent of active hydrogen aldimine one molar equivalent of isocyanate groups MDIDeliminating the reactive group reacts completely, as a product of accession, meet the formula (I), is obtained polyamidimide. A simple way to get a variety of polyamidimide without needing to obtain the corresponding primary polyamines, which are only partially accessible in industry and Commerce. Depending on the structure, functionality and molecular weight MDIDand aldimines formula (XI) these polyamidimide may have very different properties; thus, they can be chosen according to the needs for specific applications.

If, on the contrary, the reaction of the merger between aldimines formula (XI) and polyisocyanateDheld in posteriorities conditions, i.e. when is the Eney than one molar equivalent of active hydrogen aldimine one molar equivalent of isocyanate groups MDI (which isocyanate groups will react only partially), the quality of the product attach it turns out heterofunctional compound, i.e. the compound of formula (I), which in addition to one or more alvinovich groups has one or more isocyanate groups. It is shown that the value of the index q is greater than 0.

Collected in this way the addition products of aldimines formula (XI) to the MDIDi.e. aldimine-containing compounds of the formula (I), does not smell, as aldimine formula (XI). In suitable conditions, in particular in the absence of moisture, they are stable when stored.

Aldimine formula (XI), and eliminatorias the compounds of formula (I) have a very wide scope. In principle, they can be used everywhere, where they can serve as a source of aldehydes of the formula (IV) and/or aminesB. In particular they can be used in functions protected amines, respectively, protected aldehydes, active aldehyde and/or amine systems, and there may purposefully protection may be removed. In particular, they find application in systems in which there are compounds that react with primary amines. Removing the protection is carried out hydrolytically, for example, by contact with water or moisture, in particular air moisture.

When moisture aldimine product group accession of the formula (I) can hydrolysates through an intermediate stage, formally to the amino groups, and allocates the corresponding aldehydeAused to obtain aldimine formula (XI). Since this hydrolysis reaction is reversible and the chemical equilibrium is markedly shifted towards aldimine, should proceed from the fact that in the absence of active amines groups partially or completely hydrolyzed only part alvinovich groups. The reaction of the isocyanate groups with gidrolizuemye alliminum groups do not have to go through the amino group. Needless to say, it is also possible reaction with the intermediate stages of hydrolysis. For example, it is possible to gidrolizuacy aldimine group in the form of polyamines directly reacted with isocyanate groups.

In addition, the composition includes isocyanatomethyl polyurethaneP. The term "polymer" refers here and throughout this document to a set of chemically identical but differ in the degree of polymerization, molecular weight and chain length of the macromolecules, which were obtained by polyreactive, as well as to derive such a set of macromolecules from polyeucte, i.e. to compounds, which were obtained by reactions, such as, for example, addition or substitution of functional groups of the above macromolecules and which may be chemically identical or chemically reading is unchanged. The term "polyurethane polymer" includes all polymers that are obtained by the method of diisocyanate polyaddition. It also includes polymers which almost do not contain or not contain urethane groups, such as simple polyetherurethane, complex polyetherurethane, simple palifermin, polyurea complex palifermin, polyisocyanurate, polycarbamide etc.

The term "predecessor synthetic material" in this document are indicated Monomeric, oligomeric or polymeric organic compounds (or homogeneous or heterogeneous compositions containing such compounds), which are contained in them available for polyreactive active groups capable, alone or together with other molecules to react with the formation of high-molecular synthetic material, organic polymers - a process that is commonly called "hardening" or "curing", regardless of whether taking place during the curing reaction to covalently or otherwise crosslinked structures.

The concept of "polyreactive" includes all types of reactions polyaddition, polycondensation and polymerization.

Polyurethane polymerPobtained by reaction of at least one polyol with at least one polyisocyanate. This is aimogasta can be bringing in the usual way polyol and a polyisocyanate in the reaction, for example, at temperatures from 50°C to 100°C, possibly with the addition of suitable catalysts, the polyisocyanate is dosed so that its isocyanate groups were in stoichiometric excess relative to the hydroxyl groups of the polyol. Excess MDI is selected so that the resulting polyurethane polymerPafter all react the hydroxyl group of the polyol, the content of free isocyanate groups remained equal, for example, 0.1 to 15 wt.%, in particular 0.5 to 5 wt.% in the calculation for the entire polyurethane polymerP. Perhaps polyurethane polymerPcan be obtained by the additional use of plasticizers, and used plasticizers do not contain active isocyanate groups.

As polyols to obtain such isocyanatobenzene polyurethane polymerPcan be used, for example, the following commercially available polyols or any mixtures thereof:

- polyoxyalkylene, also called simple polyether polyols 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-starter with two or more active Atmanivedanam, as, for example, water, ammonia or compounds with several OH or NH groups such as, for example, 1,2-ethanediol, 1,2 - and 1,3-propandiol, neopentylglycol, diethylene glycol, triethylene glycol, isomers of dipropyleneglycol and dipropyleneglycol, isomers of butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanol, 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 also be used as polyoxyalkylene with a low degree of unsaturation (measured by ASTM D-2849-69 and specified in milliequivalent unsaturation per gram of polyol (mV/g)), obtained, for example, using the so-called biocalorimetry complex catalysts (DMC catalysts), and polyoxyalkylene with a high degree of unsaturation obtained, for example, with the aid of anionic catalysts such as NaOH, KOH, CsOH or alkali alcoholate.

Especially suitable are polyoxyalkylene or polyoxyalkylene, in particular polyoxypropylene or polyoxypropylene.

Suitable, in particular, polyoxyalkylene or polyoxyalkylene with the degree of unsaturation of less than 0.02 µv/g and a molecular weight in the range of 1000-30000 g/mol, and polyoxin philandery and-trioli with a molecular weight of 400-8000 g/mol. The term "molecular weight" means herein an average molecular weight M_n.

Particularly suitable are also the so-called polyoxypropyleneamine with ethylene oxide at the end ("end EO, limit ethylene oxide). The latter are a special polyoxyethylene polyoxypropyleneglycol, which are obtained, for example, because a pure polyoxypropyleneamine, in particular polyoxypropylene and-trioli, upon completion of the reaction polipropilenovaya alkoxyaryl further with ethylene oxide, and so they contain primary hydroxyl groups.

- Simple polyether polyols grafted styrolacrylonitrile or acrylonitrilebutadiene.

- Complex polyether polyols, also called oligoesters obtained, for example, two - or trivalent alcohols, such as 1,2-ethanediol, diethylene glycol, 1,2-propandiol, dipropyleneglycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentylglycol, glycerol, 1,1,1-trimethylolpropane, or mixtures of the aforementioned alcohols with organic dicarboxylic acids or their anhydrides or esters, such as, for example, succinic acid, glutaric acid, adipic acid, cork acid, sabotinova acid, dodecadienol acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terephthal the Wai acid and hexahydrophthalic acid, or mixtures of the aforementioned acids, and also complex polyether polyols from lactones, such as ε-caprolactone.

- Polycarbonatediol, which is obtained by the above reaction, used for the formation of polyether polyols and alcohols with diallylmalonate, dellcorporate or phosgene.

- Polyacrylate and polymethacrylamide.

- Paleogeographical, also known as oligohydramnios, as, for example, polyhydroxyvalerate copolymers, ethylene-propylene, ethylene-butylene or ethylene-propylene-diene, which are produced, for example, by the company Kraton Polymers, or polyhydroxyvalerate copolymers of dienes such as 1,3-butadiene or mixtures of diene and vinyl monomers such as styrene, Acrylonitrile or isobutylene, or polyhydroxybutyrate polybutadiene, for example, those obtained by copolymerization of 1,3-butadiene and allyl alcohol.

- Polyhydroxyvalerate copolymers of Acrylonitrile with butadiene, which, for example, can be obtained from epoxides or aminoalcohols and copolymers of Acrylonitrile to polybutadiene with terminal carboxyl groups (marketed under the name Hycar^®CTBN firm Hanse Chemie).

These polyols have an average molecular weight 250-30000 g/mol, in particular 1000-30000 g/mol and an average OH functionality in the range from 1.6 to 3.

Additionally these these polyols in obtaining polyurethane polymer Pcan be used a small amount of low molecular weight two - or polynuclear alcohols, such as 1,2-ethanediol, 1,2 - and 1,3-propandiol, neopentylglycol, diethylene glycol, triethylene glycol, isomers of dipropyleneglycol and dipropyleneglycol, isomers of butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanol, 1,3 - and 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, dimeric fatty alcohols, 1,1,1-trimethyloctane, 1,1,1-trimethylolpropane, glycerol, pentaerythritol, sugar alcohols like xylitol, sorbitol or mannitol, sugars as sucrose, other higher alcohols, low molecular weight products alkoxysilane the above two - and polynuclear alcohols, and also mixtures of the aforementioned alcohols.

As polyisocyanates to obtain such isocyanatobenzene polyurethane polymer used monomers or oligomers two - or polynuclear isocyanates, which were listed as polyisocyanatesDsuitable for receiving eliminatorias the compounds of formula (I). As polyisocyanates are suitable, in particular, MDI, HDI, TDI and IPDI.

As described above, present in the composition eliminatorias compound of formula (I) can be obtained separately and introduced into the composition as it is. However, it can also be obtained in situ, i.e. in the course of obtaining the composition, t is m, what is a suitable amount of at least one aldimine formula (XI) and at least one MDIDresult in reaction in situ, i.e. in the presence of other components of the composition. When the polyisocyanateDpreferably is isocyanatomethyl polyurethane polymerPwhat has been described in detail above.

Typically eliminatorias compound of formula (I) is present in an amount of from 0.1 to 30 wt.%, preferably from 0.5 to 20 wt.% and, in particular, from 1 to 10 wt.% in the calculation of the composition.

For the case when eliminatorias compound of formula (I) is a heterofunctional, its content can be more than 30 wt.%. In this case, its content may also reach almost to 100 wt.%, since this composition by adding water crosslinks. This occurs when m, q and p in the formula (I) are chosen so that m^*p ≤ q.

Advantageously, if the composition, in addition to eliminatorias the compounds of formula (I) and a polyurethane polymer P contains at least one catalystKAT-1. As catalystKAT-1suitable compounds that are stable when stored together with isocyanate groups and which accelerate leading to the curing of the composition of the reaction of the isocyanate groups, in particular the reaction with alliminum groups, as well as moisture. As suitable catalystsKAT-1 should be called acids, for example organic carboxylic acids such as benzoic acid, salicylic acid or 2-nitrobenzoic acid, anhydrides of organic carboxylic acids as phthalic anhydride or anhydride hexahydrophthalic acid, silloway ester of organic carboxylic acids, organic sulfonic acids, such as methanesulfonate acid, p-toluensulfonate acid or 4-dodecylbenzenesulfonic acid, or other organic or inorganic acids; metal compounds, for example, tin compounds, for example, dicarboxylate dialkylamino as the diacetate dibutylamine, bis-2-ethylhexanoate dibutylamine, dilaurate dibutylamine, dipalmitate dibutylamine, distearate dibutylamine, dioleate dibutylamine, delinat dibutylamine, delineat dibutylamine, deacetylation dibutylamine, maleate dibutylamine, dibutylamino-bis-octylamine, phthalate dibutylamine, dilaurate dimethylurea, diacetate dactylology or dilaurate dactylology, mercaptide dialkylamino, such as dibutylamine-bis-(2-ethylhexylphthalate) or dictyosome-bis-(2-ethylhexylphthalate), dibutyltindilaurate, monobutylether, alkylation, the oxide dibutylamine, the oxide dictyosome; carboxylate of tin(II), as octoate tin(II)2-ethylhexanoate, tin(II)laurate, tin(II)oleate, tin(II or is aftinet tin(II), Oksana divalent tin, as laurelbrooke, compounds of bismuth, as octoate bismuth(III), neodecanoate bismuth(III) or axinet bismuth(III); a weakly basic, tertiary amine compounds, such as simple 2,2'-disorganizational ester and other derivatives morpholino ether; and combinations of these compounds, in particular acids and compounds of metals or metal compounds and compounds containing amino groups.

Possibly, the composition comprises further components, which are typically used according to the prior art. In particular, the composition may contain one or more of the following auxiliary substances and additives:

- plasticizers, for example esters of organic carboxylic acids or their anhydrides, phthalates, such as dioctylphthalate or diisodecylphthalate, adipate, as, for example, dioctyladipate, sebacate, polyols, such as, for example, polyoxyalkylene or complex polyether polyols, esters of organic phosphoric and sulfonic acids or polybutene;

- solvents, for example ketones, such as acetone, methyl ethyl ketone, Diisobutylene, acetonylacetone, mesityloxide, as well as cyclic ketones, as methylcyclohexane and cyclohexanone; esters like ethyl acetate, propyl or butyl acetate, formate, propionate or malonate; ethers, such as keeeper, the Fira of alkoxysilane and dialkyl ethers, as diisopropyl ether, diethyl ether, disutility ether, dietilenglikoluretan ether, and ethylene glycol diethyl ether; aliphatic and aromatic hydrocarbons like toluene, xylene, heptane, octane, and various petroleum fractions like naphtha, white spirit, petroleum ether or benzene; halogenated hydrocarbons like methylene chloride; and N-alkylated lactams, such as N-methylpyrrolidone, N-cyclohexylpiperidine or N-dodecylmercaptan;

inorganic and organic fillers, such as ground or precipitated calcium carbonates, which may be covered with stearates, in particular highly dispersed coated calcium carbonate, carbon black, kaolin, aluminum oxide, silicic acid, powder or grain hollow PVC; fiber, for example, polyethylene; pigments;

- other, conventional in polyurethane chemistry, catalysts;

- reactive diluents and staplers, such as polyisocyanates, 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, oligomers and polymers of these polyisocyanates, in particular isocyanurate, carbodiimide, uretonimine, biuret, allophanate and iminoimidazolidine these polyisocyanates, the addition products of polyisocyanates to korotkie eznim the polyols, and dehydrated adipic acid and other dihydrazide;

- latent polyamine, as, for example, polyamidimide, polyetilene, polyanaline, polyoxazolines adsorbed on the zeolite or microencapsulated polyamine, and also complexes of amine-metal, preferably polyamidimide, obtained by the reaction of primary aliphatic polyamine with aldehydes, in particular aldehydeAas, for example, 2,2-dimethyl-3-acyloxymethyl, in particular 2,2-dimethyl-3-neurological, and also complexes methylenedianiline (MDA) and sodium chloride (manufactured in sale Crompton Chemical in the form of a dispersion in diethylhexylphthalate or diisodecylphthalate under the trade name Caytur^®21);

driers, as, for example, p-totalitarian and other active isocyanates, esters orthomorphisms acid, calcium oxide; VINYLTRIMETHOXYSILANE or other fast gidrolizirovanny silanes, such as, for example, organoalkoxysilanes that in the α-position of a silanol group-containing functional group, or molecular sieves;

the modifier rheological properties, such as thickeners, for example, compounds of urea, polyamide waxes, bentonites or pyrogenic silicic acids;

- adhesion promoters, in particular silanes, such as, for example, epoxysilane, vinylsilane, (meth)acryloyloxy, isocyanatobenzene, carbonatation, S-(and kilcarbery)-mercaptoethane and eliminazione, and also oligomeric forms of these silanes;

the stabilizers from the action of heat, light and UV radiation; fire retardants;

- surfactants, such as, for example, suturing, to contribute to spreading the funds to accelerate drying or defoamers;

- biocides, such as algaecides, fungicides or substances which inhibit fungal growth;

as well as other substances commonly used in isocyanatomethyl compositions.

In addition, the composition may include polymers containing hydrolyzable organoalkoxysilanes groups, which are referred to herein as "wilanowie groups". As examples of such polymers containing silane groups, should include the following: the reaction products isocyanatomethyl polyurethane polymers with active isocyanates by organoalkoxysilanes, as, for example, mercaptoethylamine or aminoalkylsilane described, for example, in US 3632557, in particular, the reaction products isocyanatomethyl polyurethane polymers from the reaction products, joining Michael aminoalkylsilanes and esters of maleic or fumaric acid, as described, for example, in EP 0403921 B1; the reaction products of gidrauxilirovania polymers having terminal double bonds, in particular polyoxyalkylene polymers with allyl end groups, with al what oxirane, described, for example, in US 3971751 and US 6207766; the reaction products of polymers containing active hydrogen atoms, such as hydroxyl or mercaptopropyl, isocyanatobenzene described, for example, in US 4345053 and US 5990257; polymers containing 3-(N-celelalte)-aminopropanoic groups, which are the reaction products of polymers containing 3-oxopropionate group, with aminoalkylsilane described, for example, in WO 2004/056905 A1.

The composition can also contain polymers, which have both isocyanate and silane groups.

The molar ratio between alliminum and isocyanate groups in the composition is preferably of 0.1 to 1.1, preferably of 0.25 to 1.0, particularly preferably 0.5 to 1.0.

Composition was prepared and stored in the absence of moisture. In a suitable airtight container or layout, as, for example, in a barrel, bottle or cartridge, it has excellent storage stability. In this document the term "stable storage" and "storage stability" in connection with the composition indicated condition, when the viscosity of the composition under suitable storage for the considered period of time does not change or changes only so that the composition remains applicable as defined.

Described composition is suitable as a synthetic precursor of the mother of the La.

If the composition is brought into contact with moisture, it solidifies with the formation of high molecular weight polyurethane polymer. Thus, the composition is a moisture curing and is called one-component moisture curing composition. Curing is based on the combination of different reactions of hydrolysis, addition and condensation between contained in the composition of the reactive groups, namely alliminum groups and isocyanate groups, and also the audience may wilanowie groups. Aldimine groups hydrolyzed to formally amino group and quickly react with isocyanate groups to form urea groups. Isocyanate groups react with each other with formation of urea groups and silane groups react with each other with the formation of siloxane groups. The reaction between gidrolizuemye alliminum groups and isocyanate groups is faster than the reaction of isocyanate groups with each other, and proceeds to complete or almost complete disappearance alvinovich groups. This gidrolizuacy aldimine do not need to react with isocyanate groups in the fully hydrolyzed form, i.e. as amino groups, but can also react with the isocyanate groups in the partially hydrolyzed form, for example, in the de pollinating groups. In addition to the moisture curing compositions contribute and also other factors, such as intense heat, for example, from 80 to 200°C, or UV radiation, or a combination of these factors.

Provided that there is enough moisture, the composition cures rapidly and completely to essentially non-adhesive mass. Curing proceeds without formation of bubbles, as the isocyanate groups are partially or completely reacted with gidrolizuemye alliminum groups, and therefore produced little CO₂or not formed. Curing is accelerated in the presence of catalysts, for example the above-mentioned organic carboxylic acids or sulfonic acids, for additional hydrolysis alvinovich groups, without causing the formation of bubbles. The moisture required for curing may take from the air (air moisture), and the composition is cured by diffusion of moisture from the outside in. However, you can also bring the composition into contact with the aqueous components, for example, by lubricating, for example, a polishing agent, by spraying or by immersion, or can be added to the aqueous composition components, for example, in the form of aqueous paste, which, for example, homogeneous or heterogeneous mixed with the composition in a static mixer.

Due to the absence of odor in Aldini the containing compounds of formula (I), composition before, during, and after curing has no smell. Thus, it can also be used in applications involving no smell, as, for example, for bonding, sealing, coating or lining inside vehicles or buildings.

The composition can be used for different purposes as a predecessor of synthetic material. In particular, it is suitable for use as an adhesive for bonding different bases, for example, for bonding of structural parts in the manufacture of motor vehicles, rail vehicles, ships or other industrial objects as different kinds of sealants, for example, for sealing joints in building constructions, as well as a coating or cladding for different products or different bases. As preferred coatings protective paint, varnish coating and the protective coating. From facing as preferred, it should be mentioned, in particular, flooring. Such facings get what the song is usually poured on the ground and level, where it cures to receive flooring. For example, these flooring are used for offices, residential premises, hospitals, schools, warehouses, automotive garages, and other private or industrial applications. As these applications have a place in the big PLO is Adah, the already paltry selection of substances from the deck leads to problems with health and/or smell, even if we are talking about applying on the open areas. Of course, a large part of the flooring is put in the interior, making small education smell is of special significance.

In one preferred embodiment, the implementation of the described compositions are applied as an adhesive or sealant.

When applied as an adhesive composition is applied on the basis ofS1and/orS2. Thus, the adhesive may be applied to one or the other, or on both bases. Then glued the parts together, then glue cures. Thus it is necessary to ensure that the connection parts took place during the so-called open time, to ensure that both the joined parts securely glued with each other.

When used as a sealant composition is applied between the bases of theS1andS2and then there is a cure. Usually sealant presoviet in the seam.

In both applications the basis ofS1and the basis ofS2may be the same or different.

Suitable basesS1orS2are, for example, inorganic bases such as glass, glass ceramic, concrete, mortar, brick, tile, plaster and natural stone such as granite or marble; metals is whether the alloys, as aluminum, steel, nonferrous metals, galvanized metals; organic bases, such as wood, synthetic materials, such as PVC, polycarbonates, PMMA, polyester, epoxy resins; coated with the basics, such as metals or alloys with a dusting powder; and also paints and varnishes, in particular automotive lacquers.

It is possible to apply adhesive or sealant, the basics can be pre-processed. This pre-processing includes, in particular, the processes of physical and/or chemical cleaning, such as grinding, sandblasting, brushing or the like, or processing cleaners or solvents, or the application of the adhesion promoter, the solution of the adhesion promoter or primer.

By "primer" herein means a composition suitable as a primer, which in addition to inactive volatile substances and optional solid additive contains at least one polymer and/or at least one substance with reactive groups and which is capable, when applied to the base to harden to a solid film having good adhesion with the layer thickness of typically 10-15 μm, and curing is carried out either by evaporation inactive volatile substances, such as solvent or water, or through chemical reaction, or by a combination of these factors, and Kotor which forms a good bond with done next layer, for example with glue or sealant.

The adhesive or sealant is preferably uniformly. The coating composition can be carried out in a wide temperature range. For example, the composition can be applied at room temperature, which is typical for elastic adhesive or sealant. However, the composition can also be applied at lower or higher temperatures. The latter is advantageous especially when the composition contains a highly viscous or fusible components which are usually present in the hot melt adhesives, for example, in a moderately hot melt (Warm-Melt and hot melt (Hot Melt) adhesives. Temperature mapping for moderately hot melt adhesives are, for example, from 40 to 80°C, and melt - from 80 to 200°C, in particular from 100 to 150°C.

After bonding or sealing of the fundamentalsS1andS2using the compositions have glued or sealed product. This product can be a structure, in particular ground or underground structure, or vehicle, for example, water or land vehicle, in particular a car, bus, truck, train or ship, or any part thereof.

In particular, if the composition is used as an adhesive for elastic bonding, it preferably has a pasty consistency with strukturnovyazkikh properties. This adhesive is applied on the basis of the approach is Asim device, preferably in the form of tracks that may be essentially circular or triangular cross-section. Suitable methods of applying the adhesive are, for example, application of the standard cartridges, which are manually or which operate on compressed air, or the application of barrels or tin containers with a pressure pump or extruder, possibly with the help of a robot for the application. Adhesive with good characteristics of the coating has a high resistance and a short ductility. This means that after the application saves the marked form, i.e. does not spread, and after a stop device for applying no or very short filaments, so that the basis is not contaminated.

The composition has a high early strength. For application, in particular as glue this means that the adhesive connection before full curing may to some extent be able to withstand that in industrial production, for example in car Assembly, has a great advantage, because the pasted items are already in a relatively short time due to the bonding can be installed in place and thereby bonded object can be moved without additional fixing and continue processing.

The composition in the cured state has a superb properties. For example, it has high is some elasticity and high tensile strength tensile. Its modulus of elasticity varies depending on the components used to produce compositions, such as polyols, polyisocyanates or polyamine, and can be installed in accordance with the requirements of the particular application, for example, high values for glue or low values for the sealant. Its adhesion to different bases is great that because of the rapid curing it is not taken for granted, since, according to experience, fast curing compositions are often too poorly prone to the formation of the clutch. With regard to resistance to the effects of aging, such as heat, sunlight or UV radiation, moisture, steam or the influence of chemicals, there are no deviations from the behavior typical of isocyanatomethyl polyurethane polymers in dry condition.

EXAMPLES

Description of measurement methods

Infrared spectrameasured on a Fourier transform infrared spectrometer 1600 firm Perkin-Elmer (horizontal ATR measuring cell with ZnSe crystal); the samples were applied diluted in the form of a film. The absorption bands are indicated in wave numbers (cm^-1) (measurement range: 4000-650 cm^-1).

Spectra¹H-NMRmeasured on the spectrometer type Bruker DPX-300 when 300,13 MHz; chemical shifts δ are indicated in ppm relative to tetrametric the Ana (TMS), the coupling constant J is specified in Hz. The binding schema (t, m) is given even when it is just about the picture of pseudocatalase.

Viscositymeasured on a viscometer thermostated with a conical disk Physica UM (cone diameter 20 mm, the angle of the solution cone of 1°, the distance between the apex of the cone and the plate of 0.05 mm, shear rate 10 to 1000^-1).

Full content alvinovich groups and free amino groupsin the resulting compounds (amine content determined by titrimetric (0,1N. HClO₄in glacial acetic acid, crystal violet indicator), it is always indicated in mmol NH₂/g (even when it says not only about the primary amino groups).

Aldimine formula (XI)

AldimineAL1

In a round flask under nitrogen atmosphere were placed 40,64 g (0,143 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 11,68 g (0.133 mol) of N-methyl-1,3-propandiamine, and the temperature of the reaction mixture was raised to 38°C. thereafter, the liquid components were removed in vacuo (10 mbar, 80°C). Received of 49.8 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine 5,20 mmol NH₂/year Product mainly is in the form of open-chain (aliminosa).

IR: 3329 (N-H), 2954, 2922, 2852, 789, 1736(=O) 1668(C=N), 1466, 1419, 1392, 1374, 1348, 1300, 1249, 1234, 1160, 1112, 1069, 1058, 1021, 996, 938, 886, 876, 820, 722.

¹H-NMR (CDCl₃, 300K): δ 7,53 (s, 1H, CH=N)to 4.01 (s, 2H, CH₂O)3,44 (t, 2H, CH=NCH₂CH₂), 2,58 (t, 2H, NHCH₂), 2,42 (s, 3H, CH₃NH), 2,30 (t, 2H, CH₂CO), 1,76 (t, 2H, CH=NCH₂CH₂), to 1.61 (m, 3H, CH₂CH₂CO and CH₃NHCH₂), of 1.27 (m, 16H, CH₃-(CH₂)₈-CH₂CH₂CO), 1,10 (s, 6H, C(CH₃)₂-CH₂O)to 0.89 (t, 3H, CH₃-(CH₂)₁₀-CO).

AldimineAL2

In a round flask under nitrogen atmosphere were placed 30,13 g (0,106 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 15,00 g (0,096 mol) N-cyclohexyl-1,3-propandiamine, and the temperature of the reaction mixture was raised to 36°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Obtained with 43.2 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine 4,39 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3308 (N-H), 2921, 2851, 2659, 1737 (C=O), 1668 (C=N), 1465, 1449, 1418, 1393, 1366, 1346, 1301, 1248, 1158, 1111, 1068, 1020, 1002, 938, 888, 845, 797, 721.

¹H-NMR (CDCl₃, 300 K): δ 7,53 (s, 1H, CH=N)to 4.01 (s, 2H, CH₂O)of 3.43 (t, 2H, CH=NCH₂CH₂), to 2.65 (t, 2H, NHCH₂), is 2.40 (s, 1H, Cy-C¹HNH), to 2.29 (t, 2H, CH₂CO)to 1.86 (m, 2H, 2Cy-H), 1,2 (m, 4H, 2Cy-H and CH=NCH₂CH₂), to 1.60 (m, 3H, CH₂CH₂CO and CH₃NHCH₂), of 1.26 (m, 22H, CH₃-(CH₂)₈-CH₂CH₂CO and 6Cy-H)of 1.09 (s, 6H, C(CH₃)₂-CH₂O)to 0.88 (t, 3H, CH₃-(CH₂)₁₀-CO).

AldimineAL3

In a round flask under nitrogen atmosphere were placed 69,31 g (0,244 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 14,72 g (0,112 mol) dipropylenetriamine, and the temperature of the reaction mixture was raised to 36°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Received 79,7 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having the amine content of 4.17 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3308(N-H), 2952, 2921, 2851, 1737(C=O), 1667(C=N), 1466, 1418, 1393, 1373, 1348, 1301, 1248, 1234, 1159, 1111, 1070, 1019, 1001, 936, 875, 722.

¹H-NMR (CDCl₃, 300K): δ 7,53 (s, 2H, CH=N)to 4.01 (s, 4H, CH₂O), 3,42 (t, 4 H, CH=NCH₂CH₂), 2,61 (t, 4H, NHCH₂), to 2.29 (t, 4H, CH₂CO), at 1.73 (m, 4H, CH=NCH₂CH₂), to 1.59 (m, 5H, CH₂CH₂CO and CH₂NHCH₂), a 1.25 (m, 32H, CH₃-(CH₂)₈-CH₂CH₂CO), of 1.09 (s, 12H, C(CH₃)₂-CH₂O)of 0.87 (t, 6H, CH₃-(CH₂)₁₀-CO).

AldimineAL4

In round number is in the atmosphere of nitrogen was placed 34,15 g (0,120 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 12,02 g (0,056 mol) bis-hexamethylendiamine (BHMT-HP; Invista), and the temperature of the reaction mixture was raised to 35°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Obtained by 43.6 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine 3,68 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 2922, 2851, 1737 (C=O), 1668 (C=N), 1465, 1417, 1393, 1373, 1340, 1248, 1234, 1159, 1111, 1020, 1003, 933, 870, 722.

¹H-NMR (CDCl₃, 300 K): δ 7,52 (s, 2H, CH=N), was 4.02 (s, 4H, CH₂O)to 3.36 (t, 4H, CH=NCH₂CH₂), at 2.59 (t, 4H, NHCH₂), to 2.29 (t, 4H, CH₂CO), 1,76-is 1.51 (m, 13H, CH=NCH₂CH₂, NHCH₂CH₂CH₂CH₂CO and CH₂NHCH₂), 1.27mm (m, 40H, CH₃-(CH₂)₈-CH₂CH₂CO and NHCH₂CH₂CH₂), 1,10 (s, 12H, C(CH₃)₂-CH₂O)to 0.88 (t, 6H, CH₃-(CH₂)₁₀-CO).

AldimineAL5

In a round flask under nitrogen atmosphere were placed 30,28 g (0,106 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added to 5.00 g (0,049 mol) Diethylenetriamine. Then the liquid components were removed in vacuo (10 mbar, 80°C). Received 33.1 g of colorless, thin liquid at room temperature is e, transparent liquid, odorless, having a content of the amine 4.07 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3348 (N-H), 2952, 2921, 2852, 1735 (C=O), 1668 (C=N), 1632, 1465, 1417, 1393, 1373, 1345, 1248, 1232, 1158, 1110, 1056, 1022, 1005, 986, 931, 903, 875, 820, 721.

AldimineAL6

In a round flask under nitrogen atmosphere were placed 20,97 g (0,074 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 10,00 g (0,067 mol) triethylenemelamine (Jeffamine^®XTA-250; Huntsman), and the temperature of the reaction mixture was raised to 33°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Received of 29.5 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine 2.21 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3444 Shire. (O-H), 2952, 2921, 2852, 1736 (C=O), 1668 (C=N), 1466, 1418, 1394, 1374, 1366, 1350, 1301, 1248, 1145, 1116, 1067, 1023, 998, 932, 890, 829,722.

¹H-NMR (CDCl₃, 300 K): δ to 7.59 (s, 1H, CH=N), a 4.03 (s, 2H, CH₂O), 3,79-3,59 (m, 12H, HOCH₂CH₂OCH₂CH₂OCH₂CH₂N), 3,47 (s, 1H,HOCH₂), 2,31 (t, 2H, CH₂CO)to 1.61 (m, 2H, CH₂CH₂CO)of 1.27 (m, 16H, CH₃-(CH₂)₈-CH₂CH₂CO)to 1.11 (s, 6H, C(CH₃)₂-CH₂O)of 0.87 (t, 3H, CH₃-(CH₂)₁₀-CO)./p>

AldimineAL7

In a round flask under nitrogen atmosphere were placed 34,48 g (0,121 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel within 15 minutes was added 20,00 g (0,117 mol) of ISOPHORONEDIAMINE (Vestamin^®IPD, Degussa). Then the liquid components were removed in vacuo (10 mbar, 80°C). To the thus obtained colorless transparent oil at room temperature was added 25,25 g (0,121 mol) of isobutylacetate (SR-506, Sartomer). Left to mix for 30 minutes at room temperature, then the mixture was heated to 85°C and held at this temperature for 24 hours. Then volatile components were removed under high vacuum (100°C). Obtained by 72.0 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine to 3.09 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3322 (N-H), 2950, 2923, 2871, 2852, 1732 (C=O), 1668 (C=N), 1457, 1418, 1388, 1377, 1364, 1310, 1294, 1248, 1196, 1165, 1110, 1053, 1015, 987, 969, 942, 931, 914, 893, 863, 840, 796, 722.

AldimineAL8(comparison)

In a round flask under nitrogen atmosphere were placed 48,18 g (0,243 mol) 3-phenoxybenzaldehyde. Under intensive stirring from a dropping funnel over 5 minutes was added 20,00 g (0,227 mol) N-methyl-1,3-propandiamine, and the temperature of the reaction mixture was raised to 40°C. Then the liquid components were removed in vacuum 10 mbar, 80°C). Received of 63.7 g of light yellow, thin liquid at room temperature, transparent, strong-smelling liquid with amine content was 7.08 mmol NH₂/, the Product is mainly cyclic (tetrahydropyrimidines) form.

IR: 3270 (N-H), 3060, 3036, 2978, 2940, 2837, 2773, 2692, 1935, 1865, 1778, 1702, 1645, 1582, 1483, 1456, 1442, 1418, 1370, 1353, 1308, 1236, 1210, 1188, 1163, 1128, 1108, 1072, 1053, 1023, 990, 964, 937, 917, 900, 889, 877, 839, 775, 748, 690.

¹H-NMR (CDCl₃, 300 K): δ 7,42-7,28 (m, 5 Ar-H), 7,16-7,01 (m, 4 Ar-H), 3,74 (s, 1H, Ar-CH(NH)N), 3,14 (m, 2H, HNCH^eqH^axand CH₃NCH^eqH^ax), 2,78 (m, 1H, HNCH^eqH^ax), to 2.35 (m, 1H, CH₃NCH^eqH^ax), to 2.06 (s, 3H, CH₃N)1,90 (m, 1H, CH₃NCH₂CH^eqH^ax), was 1.58 (m, 2H, CH₃NCH₂CH^eqH^axandHNCH₂).

AldimineAL9

In a round flask under nitrogen atmosphere were placed 28,06 g (0,099 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring of the dropping funnel for 3 minutes added 10,00 g (0,095 mol) of 2-(2-aminoethoxy)-ethanol (Diglycolamine agent^®; Huntsman), and the temperature of the reaction mixture was raised to 40°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Received of 36.3 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having a content of the amine 2.58 mmol NH₂/, the Product is mainly in the form of an open chain is (aliminosa).

IR: 3435 Shire. (O-H), 2954, 2922, 2852, 1736 (C=O), 1668 (C=N), 1466, 1418, 1394, 1375, 1248, 1233, 1160, 1127, 1062, 1022, 933, 893, 813, 721.

¹H-NMR (CDCl₃, 300 K): δ to 7.59 (s, 1H, CH=N), a 4.03 (s, 2H, CH₂O), 3,71 (m, 4H, HOCH₂CH₂OCH₂CH₂N)to 3.58 (m, 4H, HOCH₂CH₂OCH₂CH₂N)2,44 (Shir. s, 1H,HOCH₂), is 2.30 (t, 2H, CH₂CO)to 1.61 (m, 2H, CH₂CH₂CO)of 1.26 (m, 16H, CH₃-(CH₂)₈- CH₂CH₂CO)to 1.11 (s, 6H, C(CH₃)₂-CH₂O)to 0.88 (t, 3H, CH₃-(CH₂)₁₀-CO).

AldimineAL10

In a round flask under nitrogen atmosphere were placed 34,51 g (0,121 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 33,39 g N-oleyl-1,3-propandiamine (Duomeen^®O, Akzo Nobel; amine number = 337 mg KOH/g), and the temperature of the reaction mixture was raised to 48°C. Then the liquid components were removed in vacuo (10 mbar, 80°C). Received and 65.7 g of colorless, thin liquid at room temperature, a transparent liquid, odorless, having the amine content of 3.07 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3307 (N-H), 3001, 2954, 2921, 2851, 1739 (C=O), 1668 (C=N), 1464, 1393, 1375, 1347, 1301, 1248, 1158, 1114, 1067, 1020, 1000, 968, 935, 889, 721.

¹H-NMR (CDCl₃, 300 K): δ 7,53 (t, J=1,2) and 7,51 (s) (total 1H (a ratio of about 0,85/0,15), CH=N), of 5.34 (m, 2H, CH₂CH=CHCH₂), to 4.01 (s, 2H, C ₂O)of 3.43 (t, 2H, CH=NCH₂CH₂), 2,60 (m, 4H, CH=NCH₂CH₂CH₂and NHCH₂), is 2.30 (t, 2H, CH₂CO), a 2.01 (m, 4H, CH₂CH=CHCH₂), a 1.75 (m, 2H, CH=NCH₂CH₂), to 1.60 (m, 3H, CH₂CH₂CO and CH₂NHCH₂), to 1.47 (m, 2H, CH₂NHCH₂CH₂), of 1.26 (m, 38H, other CH₂-group)of 1.09 (s, 6H, C(CH₃)₂-CH₂O)to 0.88 (t, 6H, both CH₃CH₂CH₂).

AldimineAL11

In a round flask under nitrogen atmosphere were placed 40,00 g (0,141 mol) of 2,2-dimethyl-3-euroelections. Under intensive stirring from a dropping funnel over 5 minutes was added 24,00 g (0,128 mol) of N-(2-ethylhexyl)-1,3-propandiamine (BASF), and the mixture was heated to 80°C and simultaneously the liquid components were removed in vacuo (10 mbar). Received 61,5 g of colorless, thin liquid at room temperature, clear liquid odorless with amine content of 4.12 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3322(N-H), 2955, 2922, 2870, 2852, 2824, 1738 (C=O), 1668 (C=N), 1464, 1393, 1376, 1342, 1300, 1248, 1235, 1157, 1114, 1069, 1020, 1000, 935, 894, 873, 766, 723.

AldimineAL12

In a round flask under nitrogen atmosphere were placed 35,00 g (0,123 mol) of 2,2-dimethyl-3-euroelections. With vigorous stirring for 5 minutes was added 36,31 g heated to 50°C N-tallowalkyl-1,3-propandiamine (Duomeen^®T, Akzo Nobel; aminosalicyclic = 346 mg KOH/g), the mixture was heated up to 80°C and simultaneously the liquid components were removed in vacuo (10 mbar). Received of 69.2 g of off-white solid at room temperature, odorless, having a content of the amine 3,20 mmol NH₂/, the Product is mainly in the form of open-chain (aliminosa).

IR: 3316 (N-H), 2954, 2919, 2851, 2815, 1739 (C=O), 1668 (C=N), 1464, 1393, 1375, 1347, 1300, 1248, 1233, 1158, 1128, 1114, 1068, 1021, 1000, 968, 936, 917, 889, 873, 721.

Eliminatorias the compounds of formula (I)

Eliminatorias connectionAV1

79,21 g (40,2 mmol OH) of polyoxypropylene (Acclaim^®4200 N, Bayer; OH number 28.5 mg KOH/g), 10,79 g (43,1 mmol) 4,4'-etilendiamindisuktsinatov (MDI; Desmodur^®44 MC L, Bayer) and 10.00 g of diisodecylphthalate (DIDP; Palatinol^®Z, BASF) at 80°C was brought into reaction with a polyurethane polymer with terminal NCO groups, having a content of free isocyanate groups of 1.86 wt.% and a viscosity at 20°C 24 PA·C. To this polymer at room temperature was added 8,51 g (22,1 mmol) aldimineAL1and the mixture was thoroughly stirred using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.). The obtained transparent, homogeneous, odorless liquid with a viscosity at 20°C to 40 PA·S.

Eliminatorias connectionAV2

79,21 g (40,2 mmol OH) of polyoxypropylene (Acclaim^®4200 N, Bayer; OH number 28.5 mg KOH/g), 10,79 g (43,1 mmol) 4,4'-etilendiamindisuktsinatov (MDI; Desmodur^®44 MC L, Bayer) and 10.00 g Hai is decylphthalate (DIDP; Palatinol^®Z, BASF) were brought to reaction at 80°C with the formation of the polyurethane polymer with terminal NCO-groups, with a content of free isocyanate groups of 1.86 wt.% and a viscosity at 20°C 24 PA·C. To this polymer at room temperature was added to 10.62 g (of 14.8 mmol) aldimineAL3and the mixture was thoroughly stirred using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.). The obtained transparent homogeneous odorless liquid with a viscosity at 20°C 29 PA·S.

Eliminatorias connectionAV3

In a round flask under nitrogen atmosphere were placed 1,74 g (a 13.9 mmol NCO) of 4,4'-diphenylmethanediisocyanate (MDI; Desmodur^®44 MC L, Bayer) and heated to 50°C. From the dropping funnel with vigorous stirring for 5 minutes was added 10,00 g (a 13.9 mmol) aldimineAL3and the mixture was stirred for one hour at 50°C. the Obtained colorless, thin liquid at room temperature, a transparent, odorless liquid with amine content is 2.37 mmol NH₂/g, which gave a neutral response on the moistened pH-indicator paper.

IR: 3300 (N-H), 2952, 2922, 2851, 1735 (C=O), 1664 (C=N), 1647, 1595, 1527, 1513, 1466, 1416, 1395, 1375, 1305, 1244, 1215, 1196, 1162, 1112, 1056, 1018, 1000, 939, 918, 851, 813, 777, 751, 721.

Eliminatorias connectionAV4

In a round flask under nitrogen atmosphere were placed 3,47 g (27.7 mmol NCO) of 4,4'-diphenylmethanediisocyanate (MDI; Desmodur^®44 MC L, Bayer) and heated to 50°C. From the drip in once with vigorous stirring for 5 minutes was added 10,00 g (a 13.9 mmol) aldimine AL3and the mixture was stirred for one hour at 50°C. the Obtained pale-yellow, thin liquid at room temperature, a transparent, odorless liquid, which gave a neutral response on the moistened pH-indicator paper.

IR: 3308 (N-H), 2954, 2922, 2852, 2266 (N=C=O), 1735 (C=O), 1665 (C=N), 1596, 1526, 1514, 1467, 1415, 1395, 1374, 1306, 1244, 1216, 1197, 1162, 1110, 1059, 1018, 1000, 940, 918, 854, 813, 781, 751, 721.

Eliminatorias connectionAV5

In a round flask under nitrogen atmosphere were placed 12,94 g (103,4 mmol NCO) of 4,4'-diphenylmethanediisocyanate (MDI; Desmodur^®44 MC L, Bayer) and heated to 50°C. From the dropping funnel with vigorous stirring for 10 minutes was added 42,16 g (of 51.7 mmol) aldimineAL4and the mixture was stirred for one hour at 50°C. the Obtained pale-yellow, thin liquid at room temperature, a transparent, odorless liquid, which gave a neutral response on the moistened pH-indicator paper.

IR: 3336 (N-H), 2922, 2852, 2265 (N=C=O), 1736 (C=O), 1666 (C=N), 1640, 1594, 1513, 1488, 1465, 1416, 1394, 1373, 1307, 1237, 1169, 1110, 1065, 1018, 1000, 932, 918, 848, 812, 776, 754, 723.

Eliminatorias connectionAV6

In a round flask under nitrogen atmosphere were placed 10,00 g (51,4 mmol NCO) of the trimer of 1,6-hexamethylenediisocyanate (Desmodur^®N-3300, Bayer; the content of NCO-groups = 21,61 wt.%), dissolved in 47,05 g of dry ethyl acetate. At room temperature from a dropping funnel with vigorous stirring for 10 minutes, we use the and 37,05 g (to 102.9 mmol) aldimine AL3and the mixture was stirred for one hour. The obtained colorless, thin liquid at room temperature, a transparent, odorless liquid with amine content of 1.11 mmol NH₂/g, which gave a neutral response on the moistened pH-indicator paper.

IR: 3422 (N-H), 3308 (N-H), 2954, 2924, 2853, 1727 (C=O), 1689, 1651, 1600, 1579, 1528, 1462, 1377, 1334, 1272, 1161, 1121, 1072, 1039, 995, 948, 870, 764, 742, 704.

Composition (precursors of synthetic material)

Examples 1 to 7 and example 8 (comparison)

Each sample was weighed 100.0 g of polyurethane polymerPPI, the receipt of which is described below, in a polypropylene Cup with screw cap and placed in an atmosphere of dry nitrogen. To this was added 0.3 g of a solution of salicylic acid (5% wt. in dioctyladipate)and specified in table 1 aldimine formula (XI) in the specified amount, the mixture was thoroughly stirred using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.), immediately thereafter poured into an interior coated with varnish aluminum tube and sealed it closed. The number of added aldimine formula (XI) in all the examples corresponds to the ratio between the isocyanate groups in the polyurethane polymer and the amount of the reactive groups (aldimine group plus amino or hydroxyl group) in aldimine 1.0/0,7.

Polyurethane polymerPP1produces the following way:

1300 g of polyoxypropylene (Acclaim^®4200 N, Bayer; OH number 28.5 mg KOH/g), 2600 g polyoxypropyleneamine polyoxyethylene (Caradol^®MD34-02, Shell; OH number of 35.0 mg KOH/g), 605 g of 4,4'-etilendiamindisuktsinatov (MDI; Desmodur^®44 MC L, Bayer) and 500 g of diisodecylphthalate (DIDP; Palatinol^®Z, BASF) were brought to reaction at 80°C with the formation of the polyurethane polymer with terminal NCO groups and a content of free isocyanate groups 2,07% wt. and a viscosity at 20°C 48 PA·S.

Obtained composition was tested for stability during storage, during the formation of crusts, blisters, odor and mechanical properties after curing.

The storage stabilitywas determined from the change in the viscosity when stored in warm. For this purpose, the predecessor of the synthetic material in a closed tube was kept in an oven at 60°C and measured its viscosity for the first time in 12 hours, and the second time after 7 days of storage. The storage stability is expressed through the percentage increase of the second viscosity values compared to the first.

The results are given in table 1.

Table 1 The composition and the storage stability of the precursors of synthetic material
Example	Aldimine formula (I)	Additive aldimine [g]		The viscosity increase [%]a
Standardb	-	-	-	16
1	AL1	6,6	1,0/0,7	18
2	AL2	7,9	1,0/0,7	26
3	AL3	8,3	1,0/0,7	18
4	AL4	9,4	1,0/0,7	25
5	AL5	8,5	1,0/0,7	27
6	AL6	7,8	1,0/0,7	13
7	AL7	11,2	1,0/0,7	23
8 (comparison)	AL8	a 4.9	1,0/0,7	42
a= (viscosity after 7 DN/ viscosity after 12 hours - 1)×100% breference example without aldimine

From table 1 it is evident that the compositions of examples 1-7, which include aldimine-containing compounds of the formula (I), obtained in situ from a polyurethane polymerPP1and aldiminesAL1-AL7formula (XI), have an increased viscosity after storage, comparable to the composition of the reference example, which is not included eliminatorias connection. In contrast, the viscosity of the precursor of the synthetic material of comparative example 8, which includes eliminatorias connection corresponding to the prior art, obtained in situ from a polyurethane polymerPP1and aldimineAL8increases noticeably stronger.

To determine thetime of formation of a crust(curing time to tack-free, "tack-free time") a small portion was kept for 12 hours at 60°C predecessor of synthetic material having a room temperature, caused by the thick layer is 3 mm to cardboard and at 23°C and relative humidity of 50% was defined time, want to make when lightly touch the surface of the synthetic material by pipette from LDPE first time the pipette did not have any residue.

To determine themechanical propertiesafter curing, the other part was kept for 12 hours at 60°C predecessor synthetic material is then cast as a film thickness of about 2 mm PTFE coated metal sheet, after which the film is allowed to cure to an elastic synthetic material for 7 days at 23°C and relative humidity of 50%. Obtained a synthetic film experience according to DIN EN 53504 on the ultimate tensile strength, ultimate elongation and modulus E (rate of pulling of 200 mm/min). In addition, qualitatively assessed the formation of bubbles (number of bubbles that are formed during curing of the film), and smell (defined out of line from a distance of 10 cm, first swietlicki the film again to fully utverzhdenii film).The lightfastnessdetermined that utverzhdennuyu synthetic film within two weeks kept in sunlight at 23°C and relative humidity of 50% and an exposed surface was tested for the decomposition of the polymer.

The results are given in table 2.

Table 2 shows that the compositions of examples 1-7, which included appropriate, obtained in situ, eliminatorias compound of formula (I) according to the invention, overidealize quickly and without the formation of bubbles, had no smell and in dry condition was encountered light resistance and good mechanical properties. In contrast, the predecessor of the synthetic material of comparative example 8, which had obtained in situ eliminatorias connection corresponding to the prior art, utverjdala slower and with partial formation of bubbles was not permanent and had a strong smell.

Examples 9 and 10

Every time one of these in table 3 eliminatorias compounds of formula (I) was given in these quantities together with the polyurethane polymerPP2, the receipt of which is described below, in a polypropylene Cup with screw cap and placed in a nitrogen atmosphere. To this was added 0.3 g of a solution of salicylic acid (5% wt. in dioctyladipate), the mixture was thoroughly stirred using a centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.), immediately thereafter poured into an interior coated with lacquer aluminium tube, which was tightly closed. The number of added eliminatorias the compounds of formula (I) suitable for the t to the ratio between the isocyanate groups in the polyurethane polymer and alliminum groups in the compound of formula (I), equal to 1/1.

Polyurethane polymerPP2received as follows:

3960 g polyoxypropylene (Acclaim^®4200 N, Bayer; OH number 28.5 mg KOH/g), 540 g of 4,4'-etilendiamindisuktsinatov (MDI; Desmodur^®44 MC L, Bayer) and 500 g of diisodecylphthalate (DIDP; Palatinol^®Z, BASF) at 80°C resulted in the reaction with the formation of the polyurethane polymer with terminal NCO-groups, with a content of free isocyanate groups defined titrimetric, to 1.86 wt.% and a viscosity at 20°C 24 PA·S.

Obtained predecessors synthetic material was tested as described in example 1 methods for stability during storage, during the formation of crusts, blisters, odor and mechanical properties after curing and adhesion by the method described for p is the iMER 24. The results are given in table 4.

From table 4 it is seen that the predecessors of synthetic material of examples 9 and 10, which are received respectively from eliminatorias compounds of formula (I)AV1andAV2when storing detect a very slight increase in viscosity. When applying they otverzhdajutsja quickly and without the formation of bubbles, no smell and in dry condition has good mechanical properties.

Predecessors of synthetic material, used as adhesives

Examples 11 to 18 and example 19 (comparison)

For each example are listed in table 5 substances in the indicated amounts (in parts by weight) were processed in a vacuum mixer in the absence of moisture to contain no lumps homogeneous paste, the paste is immediately introduced into an interior coated with varnish aluminum cartridge and the cartridge tightly closed. Polyurethane polymersPP1andPP2received as described in example 1 and example 9, respectively.

PolyamidimidePA1was obtained by condensation reaction between 1,6-hexamethylenediamine were and 2,2-dimethyl-3-lauroylsarcosine (at a molar ratio of amino and aldehyde groups 1:1,05), he had an amine content to 2.94 mmol NH₂/year

PolyamidimidePA2was obtained by condensation reaction between the alpha, omega-polyoxypropylene what Ndjamena (Jeffamine ^®D-230, Huntsman; amine content = 8,29 mmol NH₂/g) and 2,2-dimethyl-3-lauroylsarcosine (at a molar ratio of amino and aldehyde groups 1:1,05), he had an amine content of 2.50 mmol NH₂/year

The ratio between the isocyanate groups in the polyurethane polymer and the amount of the reactive groups (aldimine group plus amino and hydroxyl groups) in eliminatorias the compounds of formula (I), aldimine formula (XI), and polyaluminum for all the samples was 1.0/0,7.

Obtained in this way, the adhesives were tested at the time of formation of a crust, the smell, the mechanical properties after curing and adhesion to glass. The results are given in table 6.

The shore hardnesswas determined according to DIN 53505.

Testing the tensile strength of the tensile and shear for each dimension corresponding 2 glass plates with a thickness of 6 mm, a width of 25 mm and a length of 75 mm float glass; firm Rocholl, Schönbrunn, Germany) was pre-treated with Sika activator^®(available in sale Sika Shweiz AG). After drying for 10 minutes the plate using a suitable form of PTFE was set relative to each other with a vertical distance of 5 mm so that they overlap in the head part 10 mm Region of overlap between the plates was filled with adhesive, and the adhesive was activated on the sides of the plates. The glue was utverjdala within 7 days at 23°C and relative humidity of 50%, then use the machine for tensile test was determined breaking strength at a constant shear rate of 20 mm/min according to DIN EN 1465. The values shown are the average of three measurements.

Adhesion to glass was determined by the picture of a break on the test samples used for determination of ultimate strength in tension and shear after the test. Gap, cohesive 100%, that is trapped completely in the glue, it was estimated by the value "1", and cohesion at 0%, then there is a gap that occurred entirely between the surface of the glass and glue and adhesive which, it was estimated by the value "5". Adhesion with the values of cohesive rupture less than 75% was regarded as unsatisfactory.

Other tests were carried out as described in example 1.

From table 6 it follows that the adhesives of examples 11-18, including eliminatorias the compounds of formula (I), which were obtained during floor the treatment of glue ( in situfrom aldimines formula (XI) and polyurethane polymersPP1orPP2(examples 11-15) and to obtain glue (examples 16-18), and put in the glue part in combination with polyaluminum, otverzhdajutsja quickly, have no smell and in dry condition have very good mechanical properties. In contrast, the adhesive of comparative example 36, which includes eliminatorias connection corresponding to the prior art, obtained in situ from aldimineAL8and polyurethane polymerPP1, cures slower, has a strong odor and has poor adhesion to the glass.

Examples 20 to 22 and example 23 (comparative)

For each of the examples listed in table 7 substances in the indicated amounts (in parts by weight)were processed in a vacuum mixer in the absence of moisture to contain no lumps, homogeneous paste, which was immediately put in covered inside with lacquer aluminium cartridge, and the cartridge tightly closed.

Polyurethane polymerPP2received as described in example 9.

Polyurethane polymerPP3received as follows:

2000 g of polyoxypropylene (Acclaim^®4200 N, Bayer; OH number 28.5 mg KOH/g), 1935 polyoxypropylene (Acclaim^®6300 N, Bayer; OH number of 28.0 mg KOH/g), 535 g of 4,4'-etilendiamindisuktsinatov (MDI; Desmodur^®44 MC L, Bayer) and 500 g of diisodecylphthalate (DIDP; Palatinol^®Z, BASF) were brought to reaction at 80°C to obtain a polyurethane polymer with terminal NCO-groups, the content of free isocyanate groups defined titrimetric, of 1.84 wt.% and a viscosity at 20°C 56 PA·S.

PolyamidimidePA2received as described in example 11.

The ratio between the isocyanate groups in the polyurethane polymer and the amount of the reactive groups (aldimine group plus amino and hydroxyl groups) in eliminatorias the compound of formula (I) [including the converted amino]aldimine formula (XI), and polyamidimide for all examples is 1.0/0.45 respectively.

Thus obtained adhesive felt at the time of crust formation, early strength and mechanical properties after curing. The results are given in table 8.

Cohesive strength("green strength") determine elali as follows: for each test, two glass plates with dimensions 40×100×6 mm pre-processed on the side which will be pasted, Sika activator^®(available in sale Sika Schweiz AG). After 10 minutes of drying on one of the plates parallel to the longitudinal edge of the applied adhesive in the form of a track with a triangular cross-section. After about a minute the applied adhesive was pressed to the second glass plate through the machine for tensile test (Zwick) to the thickness of the adhesive 5 mm (which corresponds to the width of the glue about 1 cm), then kept at 23°C and relative humidity of 50%. In this way there was obtained 2 times on three samples for testing and every three of them had cohesive strength through 4 and 7 hours of curing, respectively. For this purpose, the samples for testing were detached from each other through the machine for tensile tests at a constant speed strain 200 mm/min, recording the maximum force (in n/mm of length of the strip), and determined the absorption of energy to break (j) by integrating the curve of the force-elongation before rupture of the sample, the obtained values were averaged over three samples.

From table 8 it is seen that the adhesives of examples 20-22, including eliminatorias the compounds of formula (I), which in the examples 20 and 21 were obtained in the course of obtaining glue (in situfrom aldimines formula (XI) and polyurethane polymersPP2orPP3and in the example 22 to obtain glue, and was introduced into the glue with polyaluminum, find quick education cohesive strength, i.e. high cohesive strength, and after full curing possess very good mechanical properties. In contrast, the adhesive of comparative example 23, the relevant prior art, which as eliminatorias join includes only Valdimir has a noticeable slower formation of cohesive strength at comparable mechanical properties after full cure.

Predecessors of synthetic material, applicable as germ is tics

Examples 24 to 31 and example 32 (comparison)

For each of the examples listed in table 9 substances in the indicated amounts (in parts by weight) were processed in a vacuum mixer in the absence of moisture to contain no lumps smooth paste, paste immediately filled aluminum cartridge, covered inside with lacquer, and the cartridge tightly closed.

Polyurethane polymerPP4received as follows:

At 80°C resulted in the reaction 3560 g polyoxypropylene (Acclaim^®4200 N, Bayer; OH number of 28.1 mg KOH/g), 1000 g polyoxypropylene (Acclaim^®6300, Bayer; OH number of 28.0 mg KOH/g) and 440 g of toluylene diisocyanate (TDI; Desmodur^®T 80 P, Bayer) to obtain a polyurethane polymer with terminal NCO-groups, the content of free isocyanate groups defined titrimetric, 2.21 wt.% and a viscosity at 20°C 14 PA·S.

Polyurethane polymerPP5was prepared as follows.

At 80°C resulted in the reaction 4560 g polyoxypropylene (Acclaim^®4200 N, Bayer; OH number of 28.1 mg KOH/g) and 440 g of toluylene diisocyanate (TDI; Desmodur^®T 80 P, Bayer) to obtain a polyurethane polymer with terminal NCO groups and a content of free isocyanate groups defined titrimetric, 2.22 wt.% and a viscosity at 20°C 11 PA·S.

PolyamidimidePA2received as described in example 11.

The urea thickener was obtained as follows : the m:

In a vacuum mixer was 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 with vigorous stirring dropwise slowly added 270 g of monomethylamine. The resulting paste was continued to stir for one hour in vacuum and cooled.

The ratio between the isocyanate groups in the polyurethane polymer and the amount of the reactive groups (aldimine group plus amino and hydroxyl groups) in aldimine formula (XI), and polyaluminum for all the samples was 1.0/0,67.

Obtained in this way sealants tested at the time of crust formation, full speed curing and mechanical properties after curing. Speed full curing was determined that the sealant using gun-spray gun through a round tip (hole 10 mm) were applied to a wall-mounted piece of cardboard in the form of a horizontal, freely hanging cone with a length of about 50 mm and a thickness in the mid 30 mm, left for 7 days under normal conditions, then cut vertically in the middle and ruler measured the thickness of the cured layer of sealant. The shore hardness was determined according to DIN 53505 samples for testing, otverzhdayushchikhsya within 14 days in normal conditions. Other tests were carried out as described in example 1 and example 11.

The results of the IP is itani are given in table 10.

From table 10 it follows that the sealants according to the image is the shadow of examples 24-31, including eliminatorias the compounds of formula (I), which were obtained in the course of obtaining sealants (in situfrom aldimines formula (XI) and polyurethane polymersPP4orPP5, otverzhdajutsja quickly and in dry condition have very good mechanical properties, in particular high elasticity and low stress at 100%elongation. On the contrary, the sealant of comparative example 32, corresponding to the prior art, which contains polyamidimidePA2, cures more slowly and in dry condition has a less favorable mechanical properties.

Predecessors of synthetic material, applicable as coatings

Example 33

A mixture of 1 g of modified carbodiimide MDI (Desmodur^®CD, Bayer), 5,1 g eliminatorias connectionAV6, 0.1 g 3-glycidoxypropyltrimethoxysilane and salicylic acid on the tip of a spatula was diluted with ethyl acetate until a solids content of 50 wt.%, the resulting solution was brush applied a very thin layer on cleansed heptane glass plate (float glass; firm Rocholl, Schönbrunn, Germany) and kept under standard conditions (23°C, 50%relative humidity). After 45 minutes were formed not give tack-free, glossy-transparent and well linked the film to completely dry the surface is firm. The remaining extra Nakanoshima the solution was left to be stored for several weeks in an airtight vessel without significantly increasing the viscosity.

Example 34

A mixture of 1 g of polyurethane polymerPP6, the receipt of which is described below, 0,67 g eliminatorias connectionAV6, 0.1 g 3-glycidoxypropyltrimethoxysilane and salicylic acid on the tip of a spatula was diluted with ethyl acetate until a solids content of 50 wt.%, the resulting solution was applied by brush a thin layer on cleansed heptane glass plate (float glass; firm Rocholl, Schönbrunn, Germany) and kept under standard conditions (23°C, 50%relative humidity). After 70 minutes were formed not give tack-free, glossy-transparent and well linked film with a completely dry surface. The remaining extra Nakanoshima the solution was left to be stored for several weeks in an airtight vessel without significantly increasing the viscosity.

Polyurethane polymerPP6received as follows:

1 g polyoxypropylene (Desmophen^®1112 BD, Bayer; OH number 112 mg KOH/g), 4,06 g of IPDI trimer (Vestanat^®T 1890/100, Degussa) and of 5.06 g of ethyl acetate in a known manner brought into reaction at 60°C with the formation of the polyurethane polymer with a content of free isocyanate groups defined titrimetric, 3,94 wt.%.

1. Moisture curing composition for compositions of adhesives, sealants, coatings or cladding, including
(i) at least one isocyanatomethyl polyurethane polymer P, which is obtained from at least one MDI and at least one polyol; and
(ii) at least one eliminatorias compound of the formula

where m denotes an integer from 2 to 4,
p means an integer from 1 to 6, and
q denotes an integer from 0 to 5,
provided that p+q = 2 to 6;
and R¹means monovalent hydrocarbon residue with 6-30 atoms With,
R²and R³mean independently from each other monovalent hydrocarbon residue with 1 to 12 atoms;
R⁴means (m+1)-valent hydrocarbon residue with 2 to 12 atoms, which may contain at least one heteroatom, in particular in the form of a simple oxygen ether or tertiary amine nitrogen,
R⁵means (p+q)-valent organic residue, possibly containing heteroatoms in the form of ester, urea, urethane, biuret, allophanate, carbodiimide, uretonimine or oxidization groups or isocyanurate, which is obtained by removing (p+q) NCO-groups of R⁵-[NCO]_p+q,
and X is O or N-R⁸,
where R⁸means H or a monovalent hydrocarbon residue with 1-20 at the Mami C, which may contain at least one group of ester carboxylic acid, or
Deputy of the formula (III)

2. The composition according to claim 1, wherein R²and R³the same and, in particular, means each metal group.

3. The composition according to claim 1 or 2, characterized in that m=2.

4. The composition according to claim 1 or 2, wherein X means any monovalent hydrocarbon residue with 1-20 C atoms, or N-R⁸where R⁸means monovalent hydrocarbon residue of the formula (IX) or (IX')

where R⁹means balance-COOR¹³where R¹³means monovalent hydrocarbon residue with 1-20 C atoms,
R¹⁰means a hydrogen atom, and
R¹¹and R¹²independently from each other mean a hydrogen atom or-COOR¹³where R¹³means monovalent hydrocarbon residue with 1-20 atoms C.

5. The composition according to claim 1 or 2, wherein X is O.

6. The composition according to claim 1 or 2, characterized in that the compound of formula (I) obtained by reaction aldimine formula (XI) with polyisocyanate (D formula (XII)

7. The composition according to claim 6, characterized in that aldimine formula (XI) used in relation to one molar equivalent of active is th hydrogen aldimine one molar equivalent of isocyanate groups MDI D.

8. The composition according to claim 6, characterized in that aldimine formula (XI) used in respect of less than one molar equivalent of active hydrogen aldimine one molar equivalent of isocyanate groups MDI D.

9. The composition according to claim 6, characterized in that the polyisocyanate which is used for obtaining the polyurethane polymer P is MDI, HDI, TDI or IPDI.

10. The composition according to claim 1 or 2, characterized in that the composition additionally contains at least one polymer having organoalkoxysilanes group.

11. The composition according to claim 1 or 2, characterized in that the total proportion of all eliminatorias compounds of formula (I) is from 0.1 to 30 wt.%, preferably from 0.5 to 20 wt.% in particular from 1 to 10 wt.%, by weight of the composition.

12. The composition according to claim 1 or 2, characterized in that the index q indicates a value greater zero.

13. The composition according to item 12, characterized in that the total proportion of all eliminatorias compounds of formula (I) is from 0.1 to 100 wt.%, in particular from 30 to 100 wt.%, by weight of the composition.

14. The composition according to claim 1 or 2, characterized in that the molar ratio between alliminum and isocyanate groups in the composition is 0.1 to 1.1, preferably of 0.25 to 1.0, particularly preferably 0.5 to 1.0.

15. The cured composition as an adhesive, sealant, coating or veneering obtained by reaction what their water with a composition according to one of claims 1 to 14.

16. The use of a composition according to one of claims 1 to 14 as an adhesive, sealant or coating.

17. The application of article 16, characterized in that it is carried out inside vehicles or buildings.

18. The application of article 16 or 17 as an adhesive, sealant or coating in industrial production, or for repairs, or construction of underground or above-ground structures, or for interior decoration of vehicles or buildings.

19. Method of bonding bases of S1 and S2, which includes stages
the coating composition according to one of claims 1 to 14 on the surface of the base S1,
contacting the substrate surface S2 with a composition, which is based on S1,
curing the composition by contact with moisture, and the basics of S1 and S2 are the same or different from each other.

20. Method of sealing, which includes stages
the coating composition according to one of claims 1 to 14 between the base surface S1 and the basics S2,
curing the composition by contact with moisture, and the basics of S1 and S2 are the same or different from each other.

21. The method according to claim 19, characterized in that at least one of the bases of S1 or S2 is glass, glass ceramic, concrete, mortar, burnt bricks, tiles, plaster, natural stone like granite or marble; metal or alloy such as aluminum, steel, nonferrous metal, Zinkova the hydrated metal; organic base such as wood, synthetic material like PVC, polycarbonates, PMMA, polyester, epoxy resin; a base with a coating such as metal or alloy with powder coating; paint or varnish, in particular automotive lacquer.

22. A laminated product, which is obtained by the method of bonding according to claim 19 or 21.

23. A laminated product according to item 22, wherein the product is a vehicle, in particular a water or land vehicle, preferably a car, bus, truck, train or ship, or any part thereof.

24. Encapsulated product obtained by the method of sealing according to claim 20 or 21.

25. Encapsulated product according to paragraph 24, characterized in that it is a vehicle or building.