Hardening composition

FIELD: building materials.

SUBSTANCE: invention relates to a hardening composition used in building industry. The composition comprising a polymer with two or more thiol groups per a molecule, compound with two or more isocyanate groups per a molecule, carbon black and calcium carbonate involves additionally a filling agent wherein silicic acid or silicate is the main component or organic filling agent wherein ground powdered carbon as the main component. The composition shows satisfactory stability in storing the basic compound and the hardening capacity even after storing the basic compound and, except for, it forms the hardened join with sufficient rupture strength limit, hardness and properties of barrier for gas. The composition comprises a hydrocarbon plasticizer and an organometallic compound preferably that provides highly effective hardening properties in combination with higher mechanical strength and properties of barrier for gas. Proposed hardening composition can be used as sealing material in manufacturing isolating glasses, frames, windows for transportation means, glues and covers.

EFFECT: improved and valuable technical properties of composition.

9 cl, 12 tbl, 11 ex

 

The technical field

The present invention relates to a curing composition. In particular, the present invention relates to a curing composition suitable for sealing composition having sufficient strength and barrier properties to gas.

Background of invention

Formerly known curing composition consisting of a polymer, especially polysulfide polymers having two or more tylnej groups on the molecule and the metal-containing oxidizing agent, for example, PbO2or MnO2have excellent barrier properties against water vapor and gases, superior adhesion and excellent resistance to weathering and, in addition, have sufficient strength. Therefore, such cured compositions used for years as a protective sealant for construction, civil engineering, automobiles, aircraft or the like, the sealant compositions for the production of insulating glass, adhesives or compositions for coatings.

In particular, with regard to sealing compositions for the production of insulating glass, as described in the publication of unexamined patent application of Japan No. 9-217008 and the like, the above-described cured compositions have a tensile strength of 100-200 N/cm 2in terms of the properties and satisfactory barrier properties to gas, and therefore have a wide use in sections, for example, as sealing compounds for the production of insulating glass, which requires sufficient strength and barrier properties to gas.

Cured compositions comprising polymers having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups in the molecule have sufficient dynamic strength. In addition, similarly cured compositions comprising polymers having two or more tylnej groups in the molecule, a metal-containing oxidizing agents, even when the cured composition is exposed to outdoor conditions (outdoors) during a long period of time after application, the surface of the hardened compositions do not get dirty, so are excellent protivofaznaya properties and, in addition, also exhibit excellent adhesion. Cured compositions comprising polymers having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups per molecule, is used as the sealant compositions based on polysulfides, consisting of diastereomer polysulfide polymer and polyisocyanate compounds, and used as sealing compounds for buildings, civil engineering and the like, adhesives or compositions for coatings. Since the cured composition consisting of a polymer having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups in the molecule, does not include a metal-containing oxidizing agent, therefore, they are not harmful to the environment, and replacing cured systems with a metal-containing oxidizing agent to other systems is becoming widespread in recent years.

However, when sealing compounds based on polysulfide and polyisocyanate compounds are used as sealing compounds for the production of insulating glass, the window frames of vehicles and the like, and have the same composition as in cured compositions based on metal-containing oxidizing agent, the tensile strength at break and hardness of the hardened compositions are low, and therefore the resulting cured compositions have unsatisfactory properties. In addition, sealing compounds on the basis of polysulfide and polyisocyanate compounds have poor barrier properties to gas. It is known that carbon black is used as usilivaya the material to increase the hardness of the sealant compositions based on polysulfides. When the amount of carbon black used as a reinforcing material, increase, increases the tensile strength at break. However, there are problems in that the storage stability of the base connection is greatly diminished, and technological properties after storage base connections are also deteriorate.

Description of the invention

Cured composition of the present invention is a cured composition containing a polymer having two or more tylnej groups in the molecule, and a compound having two or more isocyanate groups per molecule, and black carbon, and optionally containing a filler, the main component of which is silicic acid or silicate, or additionally containing organic filler, the main ingredient of which is powdered coal.

In addition, the cured composition of the present invention preferably contains a polymer having two or more tylnej groups on the molecule, the compound having two or more isocyanate groups per molecule, and carbon soot and additionally contains a filler, the main ingredient of which is silicic acid or silicate, or further comprises an organic filler, the main ingredient of which is the ISM is lenny in powder coal, moreover, the composition of the hydrocarbon plasticizer is used as a plasticizer and ORGANOMETALLIC compound used as the curing catalyst, so that it may be received effectively cured composition having additionally excellent mechanical strength and barrier properties to gas.

The best way of carrying out the invention

Cured composition of the present invention contains a polymer having two or more tylnej groups on the molecule, the compound having two or more isocyanate groups per molecule, and carbon soot and additionally contains a filler, the main ingredient of which is silicic acid or silicate, or further comprises an organic filler, the main ingredient of which is powdered coal.

In addition, the cured composition of the present invention preferably contains a polymer having two or more tylnej groups on the molecule, the compound having two or more isocyanate groups per molecule, and carbon soot and additionally contains a filler, the main ingredient of which is silicic acid or silicate, or contains an organic filler, the main ingredient of which is powdered coal, and in this it is notizie hydrocarbon plasticizer is used as a plasticizer and ORGANOMETALLIC compound include in its composition as a catalyst.

The polymer having two or more tylnej groups in the molecule, and a compound having two or more isocyanate groups per molecule, in the cured compositions of the present invention form thiourethane communication through interaction between the thiol groups and isocyanate groups, and through this composition cures at room temperature.

Polymers, compounds and the like relating to the cured compositions of the present invention will be described below.

First, (a) will be described polymer having two or more tylnej groups on the molecule.

The polymer having two or more tylnej groups in the molecule may be a polymer having two or more tylnej groups in the molecule and containing ether linkage, simple thioester bond, a disulfide bond, urethane bond and/or complex the ester linkage in the main chain.

Preferred examples of the above polymers having two or more tylnej groups in the molecule include polyoxyalkylene described in the publication of examined patent application of Japan No. 47-48279, and polymercaptan described in U.S. patent No. 4092293 and publication of examined patent application of Japan No. 46-3389. Other examples of polymers having two or more tylnej groups in the molecule include having terminal thiol liquid polymers described the data in U.S. patent No. 3923748, and end with a simple thiols thioethers liquid simple thioethers described in U.S. patent No. 4366307. In addition, particularly preferred polymers are simple polyalphaolefin polymers or polysulfide polymers described below. Srednekislye molecular weight of such polymer having two or more tylnej groups in the molecule, is usually 100-200000, preferably 400-100000.

Below will be described an example of a simple polyalphaolefin polymers preferably used in the present invention.

In the present invention a simple polyalphaolefin polymer preferably includes

(1) simple polyester part presents

-(R1O)n-

(where R1represents alkylenes group having 2-4 carbon atoms, and n is an integer 6-200), and

(2) a structural unit represented by

-(C2H4Och2OS2H4-Sx)- and -(CH2CH(OH)CH2-Sx)-

(where x is an integer of 1-5) in the main chain

and, in addition, has

(3) tirinya group presents

-C2H4Och2OS2H4-SH and/or-CH2CH(OH)CH2-SH

in the limit positions.

In this simple polyalphaolefins the simple polymer polyester part, described above in (1)and a structural unit, opican the e above in (2), can be connected in any order. With regard to proportions, the component -(R1O)n- (1), preferably, is present in the amount 2-95 masses. percent, component (C2H4Och2OS2H4-Sx) (2) is present in the amount of 3-70 wt. percent and component (CH2CH(OH)CH2-Sx) (2) is present in the amount of 1-50 wt. percent. Srednekislye molecular weight of this simple polyalphaolefin polymer is usually 600-200000, preferably 800-50000. The above simple polyalphaolefin polymer can be obtained by the method described in the publication of unexamined patent application of Japan No. 4-363325.

Examples of polysulfide polymers preferably used in the present invention will be described below.

In the present invention polysulfide polymer, preferably, includes

(4) a structural unit represented by

-(C2H4Och2OS2H4-Sx)- (where x is an integer of 1-5) in the main chain and has

(5) tirinya group represented by-C2H4Och2OS2H4-SH in the limit positions. This polysulfide polymer usually has fluidity at room temperature and has srednekamennogo molecular weight 100-200000, preferably 400-50000. Preferred examples of videopix the frame polysulfide polymer described in U.S. patent 2466963.

Next will be described in (b) compound having two or more isocyanate groups in a molecule.

In the present invention, the organic polyisocyanate compound and/or a urethane prepolymer obtained by the interaction of compounds containing active hydrogen with an organic polyisocyanate compound, preferably used as compounds having two or more isocyanate groups in a molecule.

Specific examples of the organic polyisocyanate compounds include tolylenediisocyanate, diphenylmethanediisocyanate, polymethylenepolyphenylisocyanate (crude MDI), xylylenediisocyanate, isophoronediisocyanate, norbornadiene and hexamethylenediisocyanate.

Examples of compounds containing an active hydrogen include having hydroxyl end groups of polyesters, multivalent polyalkylene ethers; having terminal hydroxyl groups of the polyurethane polymers; acrylic polyols in which the hydroxyl group is introduced into the acrylic copolymers; having terminal hydroxyl groups polybutadienes; polyvalent simple thioethers; Polyacetals; aliphatic polyols; Alcantara, ascential and aliphatic thiols, including alkylthiol having two or more tylnej groups; polysulfide polymers having tirinya groups in end positions; diamines including, for example, aromatic, aliphatic and heterocyclic diamines, and mixtures thereof.

As for the cured compositions of the present invention is also possible in advance the reaction of (a) polymer having two or more tylnej groups per molecule, with (b) a compound having two or more isocyanate groups in the molecule, and the use of the product as a one-component curing composition. In this case, it is preferable to use only urethane prepolymer obtained by the interaction of the above diastereomer connection with the organic polyisocyanate compound in the presence of excess isocyanate compounds.

In the present invention the molar ratio (isocyanate groups/tirinya group) of the isocyanate groups in (b) the compound having two or more isocyanate groups in the molecule, to tilenum groups in (a) a polymer having two or more tylnej groups per molecule, preferably adjusted to 0.5 to 4.0. The molar ratio of isocyanate groups to tilenum groups is less than 0.5, is undesirable, since the molecular weight of the cured composition cannot be sufficiently improved. On the other hand, it is undesirable molar ratio of isocyanate groups to tilenum groups in excess of 4.0, is as utverjdenie connection can become hard and brittle. More preferably, when the molar ratio of isocyanate groups to tilenum groups is 0.7 to 3.0.

Next will be described in (C) carbon black.

Examples of carbon black used in the present invention include carbon black, obtained by applying the channel system, gas furnace, furnace system, running on liquid fuel, thermal systems and acetylene system.

Specific examples of carbon black include carbon EPC, carbon MPC, carbon CC, SAF carbon, carbon ISAF, HAF carbon, carbon MAF, FEF carbon, carbon HMF, SRF carbon, carbon SPF, GPF carbon, carbon APF, FF carbon, carbon, CF, SCF carbon, carbon ECF, carbon FT, MT carbon and acetylene soot. Among them, particularly preferred are carbon SRF and carbon MT, since the mechanical strength of the cured compounds increases and technological properties are satisfactory. Specific examples of carbon black include carbon black with the trade name: Asahi #15 produced by ASAHI CARBON CO., LTD., and Thermax MT, produced by SHIRAISHI CALCIUM KAISHA, LTD.

If the average particle diameter of carbon black is less than 60 nm, although it has a significant impact on increasing the mechanical strength of the cured compounds, such diameter is undesirable because technological properties can be significantly degraded Average particle diameter, exceeding 600 nm is undesirable because the effect of soot on increasing the mechanical strength of the cured compounds may become insignificant. The preferred average particle diameter of carbon black is 60-600 nm.

The amount of the mixture of carbon black, preferably, is 20-200 masses. parts relative to 100 mass. parts of the sum of (a) polymer having two or more tylnej groups per molecule, and (b) compounds having two or more isocyanate groups per molecule, more preferably 50-150 masses. parts. The amount of the mixture of carbon black is less than 20 mass. parts is undesirable because its influence on increasing the mechanical strength of the cured compounds may become insignificant. More than 200 mass. parts, is undesirable because of the technological properties may deteriorate or it is economically undesirable.

Next will be described (d-1) filler, comprising mainly of silicic acid or silicate.

Filler, the main ingredient of which is silicic acid or silicate is filler, containing 60% or more of silicic acid or silicate, preferably 70% or more of silicic acid or silicate.

Examples of synthetic products that serve as filler, the main ing what adiantum which is silicic acid or silicate, include white carbon, which is a micronized silicic acid obtained by a dry method or a wet method. Filler, the main ingredient of which is silicic acid or a silicate, preferably, is a filler containing silicic acid or silicate.

Examples of minerals that serve as filler, the main ingredient of which is silicic acid or silicate include kaolin, consisting of minerals, such as kaolinite and galloza, diatomite, originating from rocks, consisting of diatom fragments, talc derived from talcose rocks, perlite, originating from perlite rock, bentonite and acid clay, comprising mainly montmorillonite mineral clay, activated clay obtained by treating montmorrilonite clay mineral mineral acid, and, in addition, thick, siclet, wollastonite, sericite, mica, silicon dioxide, sand from silicon dioxide and stone from silicon dioxide. Among them, preferred are perlite, acid clay, white carbon black, as they have a significant impact on the suppression of coating the surface of the base compound film after storage basic compounds to suppress the increase of the thickness of the base compound after storage bazavov the connection and in addition, to suppress the reduction of vitality and time to loss of adhesion after storage base connection. In addition, acid clay and white carbon black are particularly preferred because they have a significant impact on the suppression of reduction of the relative elongation at break of the cured compounds after storage base connection.

The amount of the mixture of filler, the main ingredient of which is silicic acid or silicate is preferably 0.5 to 50 mass. parts relative to 100 mass. parts of the sum of (a) polymer having two or more tylnej groups per molecule, and (b) compounds having two or more isocyanate groups per molecule and, more preferably 1-50 wt. parts. The amount of the mixture of filler, containing mainly silicic acid or silicate, less than 0.5 wt. parts is undesirable because the effect on increasing stability during storage base connection can be minor or effect on stabilizing the ability to cure after storage of the basic compounds may also become insignificant. The amount exceeding 50 mass. parts is undesirable, since the mechanical strength may be reduced, technological properties may be deteriorated or it may be economically n is desirable.

Next will be described (d-2) an organic filler, the main ingredient of which is powdered coal.

The organic filler, the main ingredient of which is powdered coal, is a filler containing 90% or more of powdered coal, preferably 95% or more of powdered coal.

Examples of organic fillers, the main ingredient is powdered coal, include powdered products peat, lignite, brown coal, bituminous coal, and anthracite. In particular, powdered products bituminous coal and anthracite, with a content of coal 80% or more based on dry ash-free matter, are preferred due to the fact that the effect on reducing the relative density of the cured compounds and increasing the mechanical strength is significant and, in addition, the effect to suppress the reduction of vitality and time to loss of adhesion after storage base connection is significant. Specific examples of organic fillers, the main ingredient is powdered coal, include finely ground bituminous filler having a trade name Mineral Black 325BA, produced by SHIRAISHI CALCIUM KAISHA, LTD.

the number of the mixture of organic filler, the main ingredient is powdered coal, is preferably 0.5 to 150 mass. parts relative to 100 mass. parts of the sum of (a) polymer having two or more tylnej groups per molecule, and (b) compounds having two or more isocyanate groups per molecule, more preferably 1-100 mass. parts. The amount of the mixture of the organic filler, the main ingredient of which is powdered coal, less than 0.5 wt. parts is undesirable because the effect on increasing the mechanical strength or a decrease in the relative density may become low or effect on stabilizing the ability to cure after storage of the basic compounds may be negligible. More than 150 mass. parts, is undesirable because of the technological properties may deteriorate or it is economically undesirable.

In the cured compositions of the present invention should be used any one of the filler (d-1), the main ingredient of which is silicic acid or a silicate, and an organic filler (d-2), the main ingredient of which is powdered coal, but they can be used simultaneously.

Next, will be described (e) a plasticizer.

The plasticizer can the t to be mixed with the curing composition of the present invention. As a plasticizer cured compositions of the present invention can be used esters of phthalic acid, esters trimellitic acid, esters of aliphatic dibasic acids and the like. Specific examples of them include butylbenzylphthalate, dibutyl phthalate, deeptrhoat, di-2-ethylhexylphthalate, di-n-octylphthalate, diisodecylphthalate, diisononylphthalate, three 2-ethylhexylacrylate, di-2-ethylhexyladipate, distillation, disneylandia, dibutylphthalate, dibutylsebacate and di-2-ethylhexylcarbonate.

In addition, as the hydrocarbon plasticizer in the present invention can be used connection type diarylamino, connection type triarylmethane having a high boiling point aromatic hydrocarbons, consisting of products of interaction between the dimer or trimer of styrene and of alkyl benzene (trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.), examples of which are indicated in the publication of examined patent application of Japan No. 56-14705, publication of examined patent application of Japan No. 56-15440, publication of examined patent application of Japan No. 57-56511 and the like. You can also use chlorinated paraffin wax and hydrogenated terphenyl (trade name "ThermS-900"manufactured by Nippon Steel Chemical Co., Ltd.). Hydrocarbon plasticizers, for example, Tr is kildalton, are preferred due to the fact that the absorption is small and barrier properties to gas are satisfactory.

The amount of the mixture of the above plasticizer depends on the amount of filler, which is used at the same time. However, it is preferable that the amount of plasticizer was usually in the range 10-100 mass. parts relative to 100 mass. parts of the sum of (a) polymer having two or more tylnej groups per molecule, and (b) compounds having two or more isocyanate groups in a molecule.

Next will be described in (f) curing catalyst.

To quickly and reliably carry out curing after application, to the cured compositions of the present invention may be added as a curing catalyst for interaction tylnej groups with isocyanate groups.

In particular, as a curing catalyst for curing the composition of the present invention can be used tertiary amines, ORGANOMETALLIC compounds, and the like. Examples of tertiary amines include monoamines, diamines, triamine, polyamine, cyclic amines, alkanolamines and simple Firminy. Specific examples include triethylamine, N,N-dimethylcyclohexylamine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetramethylchroman-1,3-diamine, N,N,N',N'-tetrame elexan-1,6-diamine, N,N,N',N",N"-pentamethyldiethylenetriamine, N,N,N',N",N"-pentamethyldiethylenetriamine, tetramethylguanidine,

N,N-depoliticisation,

N,N-deprivationteaches, triethylenediamine,

N,N'-dimethylpiperazine, N-methyl-N'-(2-dimethylamino)ethylpiperazine, N-methylmorpholine, N-ethylmorpholine,

N-(N',N'-dimethylaminoethyl)morpholine, 1,2-dimethylimidazole, dimethylaminoethanol, dimethylaminoethoxide,

N,N,N'-Triethylenetetramine, N-methyl-N'-(2-hydroxyethyl)piperazine, N-(2-hydroxyethyl)morpholine, bis-(2-dimethylaminoethyl) ether and bis-(3-dimethylaminopropylamine) ether of ethylene glycol. Among them, preferred are compounds of the type N,N-depoliticalization. Specific examples include N,N-depoliticisation and N,N-deprivationteaches. Can be used two or more types of these tertiary amines.

In the cured compositions of the present invention, the ORGANOMETALLIC compounds can be used salts of aliphatic acids of various metals. Examples of these metals salts include cobalt, lead, manganese, zinc, copper, iron, calcium, zirconium, lithium, chromium, magnesium, cerium, barium, aluminum, cadmium, strontium and indium. Examples of the higher aliphatic acids include oktilovom acid, naphthenic acid, neodecanoate acid, butyric acid, Kapranova the acid, Caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid, beenbuy acid, lignocellulose acid, arotinolol acid, montanabuy acid, melissinos acid, obtusiloba acid, lenderyou acid, casinobuy acid, physeteridae acid, myristoleic acid, tamarinbleu acid, petroselinic acid, oleic acid, vaccinology acid, gadolinium acid, carolinabuy acid, erucic acid, selfrenewal acid, linoleic acid, girevoy acid, eleostearic acid, punitive acid, tricosane acid, linolenic acid, Morosanova acid, parinarium acid, arachidonic acid, clupanodons acid, skeletonema acid and herring acid. Specific examples of ORGANOMETALLIC compounds include cobalt naphthenate, lead naphthenate, manganese naphthenate, zinc naphthenate, copper naphthenate, iron naphthenate, calcium naphthenate, zirconium naphthenate, lithium naphthenate, chromium naphthenate, magnesium naphthenate, activit cobalt, activit lead, activit manganese, activit zinc, activit copper, activit iron, activit calcium, activit zirconium, activit lithium, activit chromium, activit magnesium, activit cerium, activit barium, activit aluminum. Among them predpochtitel the YMI are ORGANOTIN compounds, have a reduced effect on the discoloration, and the like, more preferred examples include mercaptide dialkylamino, bis(carboxylate) dialkylamino, bis(in primary forms-monoalkyl ether) dialkylamino and, in primary forms dialkylamino. Additionally, there may be used metal salts of acetylacetone, metal salts of 2,4-pentanedione and the like, which are chelate compounds of the above metals type chelate salts. Specific examples of them include an aluminium salt of acetylacetone, zinc salts of acetylacetone salt of acetylacetone manganese, calcium salt of acetylacetone, India salt of acetylacetone.

In particular, in accordance with the compositions of the present invention, ORGANOMETALLIC compounds are used preferably due to satisfactory stability during storage compared with the stability in the case of the use of amines as catalysts. Among them, metal-organic compounds on the basis of India are especially preferred due to the fact that utverjdenie connection has satisfactory initial hardness. Can be used two or more types of ORGANOMETALLIC compounds.

Hereinafter will be described in (g) other materials needed in the composition.

To further enhance the economic effect is you want to make, improve the technological properties during application of the composition and properties after curing, a cured composition of the present invention can be used fillers and additives such as calcium carbonate and titanium oxide.

In addition, to improve adhesion to a material, such as glass or aluminum, after applying to the cured compositions of the present invention may be added to the adhesion promoter.

In particular, as a promoter of adhesion using silane binding agent, etc. Examples Milanovich binding agents include γ-methacryloxypropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-mercaptopropionylglycine, VINYLTRIMETHOXYSILANE, vinyltris-(β-methoxyethoxy)silane, vinyltriethoxysilane, β-(3,4-oxicological)ethyltrimethoxysilane,

γ-glycidoxypropyltrimethoxysilane and

γ-glycidoxypropyltrimethoxysilane. In addition, the polysulfide polymer having trimethoxybenzylamine end groups, the polymer described in the publication of unexamined patent application of Japan No. 6-271833 and synthesized by the reaction of polysulfide polymer "Thiokol LP3" γ-glycidoxypropyltrimethoxysilane, can also be used as silane binder. Can be used two or more of ipow these Milanovich binders.

In addition, to increase the residual stickiness on the surface after curing, cured compositions of the present invention may be added a compound having oxidizable air unsaturated groups, as described in the publication of unexamined patent application of Japan No. 2000-178334.

Examples of compounds having oxidizable air unsaturated group include drying oils, diene compounds, and various modified substances of drying oils. Specifically, can be used fats and fatty oils (drying oils and fish fats), which are mixed triglycerides of unsaturated aliphatic acids and have an iodine number of 130 or more. Examples of unsaturated aliphatic acids include obtusiloba acid, lenderyou acid, casinobuy acid, physeteridae acid, myristoleic acid, tamarinbleu acid, petroselinic acid, oleic acid, vaccinology acid, gadolinium acid, carolinabuy acid, erucic acid, selfrenewal acid, linoleic acid, girevoy acid, eleostearic acid, punitive acid, tricosane acid, linolenic acid, Morosanova acid, parinarium acid, arachidonic acid, clupanodons acid, skeletonema acid and herring acid. Specific examples raises the selected oils include linseed oil, perillae oil, Tung oil, Japanese Tung oil, Aitimova oil, hemp oil, oil nuts, torreyi, oil inukaya, walnut oil, oil of Japanese walnut, poppy seed oil, sunflower oil, soybean oil and safflower oil. Examples of fish oil include fat sardines, herring fat and oil Menhaden. In addition, the composition include samaritane oils, obtained by alkali isomerization fish oils, digidratirovannogo castor oil, obtained by the dehydration of castor oil, and the like. Particularly preferred examples include Tung oil and Aitimova oil, which contains abundant unsaturated aliphatic acid having conjugated double bonds, for example eleostearic acid.

In the present invention it is desirable that the number of added drying oil was 0.1 to 50 mass. parts relative to 100 mass. parts of the amount of the polymer having the number of active hydrogen atoms of two or more per molecule, and compounds having two or more isocyanate groups on the molecule. If the amount added is 0.1 mass. parts or less, the effect on increasing tackiness may be small and, if the amount added is 50 mass. parts or more, economic efficiency and smell can be udovletvoridelnye.

In addition, in the present invention particularly preferably contains an active hydrogen compound and the organic polyisocyanate compound was subjected to synthesis in the presence of excess isocyanate compounds, while at the same time there is a compound containing oxidizable air unsaturated group as the compound having two or more isocyanate groups per molecule, and a compound containing oxidizable air unsaturated group can be represented consistently.

In accordance with the present invention, the cured composition consisting of a polymer having two or more tylnej groups in the molecule, compounds having two or more isocynate groups in the molecule, and carbon soot, mixed with a filler, the main ingredient of which is silicic acid or a silicate and/or organic filler, the main ingredient of which is powdered coal, and, if necessary, as a plasticizer use of hydrocarbon plasticizer and as a curing catalyst used ORGANOMETALLIC compound, so you can get cured composition suitable for use as high-strength a sealing composition having excellent mechanical strength and excellent is similar barrier properties to gas.

Cured composition of the present invention will be described in more detail with reference to the following examples.

EXAMPLE of SYNTHESIS 1

After adding 800 g defunctioning of polypropylenglycol (HE 55,3 mg KOH/g)obtained by adding propylene oxide to propylene glycol, 87,7 g of epichlorohydrin and 1.0 g of the pentahydrate of tin chloride(IV) in the reaction vessel, the stirring of the mixture was carried out at 80-90°C for 3 hours. In addition, added 887,7 g polysulfide polymer (trade name "Thiokol LP55", produced by Toray Fine Chemicals Co., Ltd.) and the mixture was stirred, after which was added 76 g of sodium hydrosulfide (purity 70%), followed by stirring at 80°C for 2 hours. Then added to 7.1 g of 50% aqueous citric acid solution and stirring was carried out for 15 minutes, followed by dehydration. In addition, removing the salt, so I got clear light yellow polymer having a mercaptan content of 2.0 mass. percent and a viscosity of 80 poises (25°).

EXAMPLES 1-4

The underlying connection was obtained by mixing the polymer of synthetic example 1 with plasticizers, fillers and additives in amounts shown in table 1. Thus obtained the underlying connection was placed in a bath at a constant temperature of 50°and evaluate the change in surface conditions. The results privadas is in table 3. In addition, mixed 350 masses. parts of the specified base connection and 51 of the masses. part urethane prepolymer (the isocyanate content of 5.3 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. The length of time during which the resulting mixture held the spatula is in the gel state, is called viability. The time that elapses before utverjdenie connection becomes unable to adhere to the plate made of polyethylene terephthalate, known as a time of loss of stickiness. Similarly, viability and loses stickiness was measured relative to the base connection after storage at 23°within 2 weeks and 4 weeks. The results of measurement of hardness (hardness JIS A) hardened compounds are also shown in table 3.

COMPARATIVE EXAMPLE 1

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 2. Thus obtained the underlying connection was placed on a steam bath with a constant temperature of 50°and evaluate the change in surface conditions. The results are given in table 3. In addition, the mix of 350 masses. parts of this base compound and 51 of the masses. part urethane prepolymer (the isocyanate content of 5.3 wt. % the NTA), obtained by adding xylylenediisocyanate to polypropylenglycol. Viability, time to loss of adhesion and hardness of the cured compounds were measured the same way in the examples, the results of this change are shown in table 3. In comparative example 1 after storage base connection at 23°viability was significantly reduced from 40 minutes to 20 minutes, and so had seen a great change in the ability to cure due to storage. In addition, after storage of basic compounds at 50°With the surface of the ground connections were covered with a film, and so had seen a great change in the state of the underlying connection due to storage.

Table 1
Source materialComposition (mass parts)
The polymer of synthetic example 1100
The plasticizer is dioctylphthalate56
The filler is calcium carbonate90
The filler is carbon black100-x
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
The filler is perlitex
(trade name Perlite B-409: Mitsui Mining &Smelting Co., Ltd.)
powdered coal
(trade name Mineral Black 325BA: SHIRAISHI CALCIUM KAISHA, LTD.)
The curing catalyst - dilaurate di-n-butyanova2
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Table 2
Source materialComposition (mass parts)
The polymer of synthetic example 1100
The plasticizer is dioctylphthalate56
The filler is calcium carbonate90
The filler is carbon black100
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
The curing catalyst - dilaurate di-n-butyanova2
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Comparative example 1
Table 3
Example 1Example 2Example 3Example 4
The amount of filler
Calcium carbonate9090909090
Carbon black10090759075
Perlite0102500
Powdered coal0001025
Utverjdaemogo (min)
The initial stage
Viable4050505545
Time loss stickiness6075756580
23°, 2 weeks
Viable2545455540
Time loss stickiness4555656585
23°, 4 weeks
Viable2045504535
Time loss stickiness4055656065
Hardness (JIS A)
23°, 1 day4345474343
23°7 days4447464542
The storage stability of the base connection
50°, 1 weekΟΟΟΟΟ
50°, 2 weeksΟΟΟ ΟΟ
50°, 3 weeksΔΟΟΟΟ
50°, 4 weeksxΔΔΟΟ
Ο: no change, Δ: viscosity increased, x: the surface was covered with foil

EXAMPLES 5 and 6

The underlying connection was obtained by mixing the polymer of synthetic example 1 with plasticizers, fillers and additives in amounts shown in table 4. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (the isocyanate content of 5.4 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. The length of time during which the resulting mixture is held spatula, was in a state of gel, called vitality. The time that elapses before utverjdenie connection becomes unable to adhere to the plate made of polyethylene terephthalate, known as a time of loss of stickiness. In addition, were tested for tensile strength under tension in the room (23° (C)based on JIS A-5758 using a sheet of float glass as the bonding material. About ASEC, seasoned in conditions of 23°C for 7 days, were tested for tensile tensile and measured the tensile strength at break (N/cm2) and elongation at break (%). In addition, obtained molded in the form of a sheet utverjdenie connection with a thickness of 1 mm using the formed mixture and measured the permeability of a gas-argon through tests on the coefficient of permeability is carried out based on JIS K-7126. In addition, similarly, has been molded in the form of a sheet utverjdenie connection with a thickness of 1 mm and a permeability to water vapor was measured by testing the permeability of water vapor, based on JIS K-7129. The test results are shown in table 6. The permeability of a gas-argon in example 5 was 1,81×10-15and permeability of the gas-argon in example 6 was 2.57 m×10-15.

COMPARATIVE EXAMPLE 2

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 5. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (the isocyanate content of 5.4 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. The results of measurement of viability, loss time whether the bones, tensile strength at break, and elongation at break, permeability gas of argon and permeability of water vapor, and the measurements were carried out in a manner similar to the method in examples shown in table 6. In comparative example 2, the coefficient of permeability gas argon was high: 3,26×10-15and, therefore, the barrier properties to gas were bad. The permeability coefficient of water vapor was 26, and therefore, the barrier properties for water vapor were bad.

Table 4
Source materialComposition (mass parts)
The polymer of synthetic example 1100
The plasticizer is an aromatic hydrocarbon76
(trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.)
hydrogenated terphenyl
(trade name "ThermS-900"manufactured by Nippon Steel Chemical Co., Ltd.)
The filler is calcium carbonate210
The filler is carbon black100
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
Filler - Elit 10
(trade name Perlite B-409: Mitsui Mining &Smelting Co., Ltd.)
powdered coal
The curing catalyst - dilaurate di-n-butyanova2
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Table 5
Source materialThe composition of

(mass parts)
The polymer of synthetic example 1100
The plasticizer is dioctylphthalate56
The filler is calcium carbonate100
The filler is carbon black90
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
The filler is perlite10
(trade name Perlite B-409: Mitsui Mining &Smelting Co., Ltd.)
The curing catalyst - dilaurate di-n-butyanova2
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LT.)

Table 6
Comparative example 2Example 5Example 6
The plasticizerThe dioctylphthalateAromatic hydrocarbonsHydrogenated terphenyl
Utverjdaemogo (min)
The initial stage
Viable553030
Time loss stickiness705550
The elasticity of N-type (23°C, 7 days)
Tensile strength at break (N/cm2)124122119
Elongation at break (%)799274
The permeability of a gas-argon (mol·m/m2·s·PA)3,26×10-151,81×10-152.57 m×10-15
Factor

the water vapor permeability (23°C, 90% relative to agnosti)(g· mm/m2·day)
261719

EXAMPLES 7-9

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 7. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (the isocyanate content of 5.4 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. The length of time during which the resulting mixture is held spatula, was in a state of gel, called vitality. The time that elapses before utverjdenie connection becomes unable to adhere to the plate made of polyethylene terephthalate, known as a time of loss of stickiness. In addition, were tested for tensile strength under tension in the room (23° (C)based on JIS A-5758 using a sheet of float glass as the bonding material. The pattern, designed in the conditions of 23°C for 7 days, were tested for tensile tensile and measured the limit of the tensile strength (N/cm2) and elongation at break (%). In the same way measured viability, the loss of stickiness, tensile strength at break and elongation p and the gap relative to the base connection stored at 40°within 2 weeks or 4 weeks. The results of this are shown in table 9. Decreased viability after storage at 40°it was possible to suppress the addition of perlite. In addition, a decrease in the relative elongation at break of the cured compounds with elasticity N-type can be suppressed by adding white soot and acid clay.

Comparative example 3

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 8. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (the isocyanate content of 5.4 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. The results of measurement of viability, time, loss of adhesion, tensile strength at break, and elongation at break, measured in a manner similar to the method specified in the examples shown in table 9. In comparative example 3 after storage base connection at 40°viability decreased significantly from 35 minutes up to 15 minutes, and, thus, had seen a great change in utverjdaemogo due to storage. In addition, the elongation at break of the cured compounds with elasticity N-type reduced the camping from 83% to 38%.

Table 7
Source materialThe composition of

(mass parts)
The polymer of synthetic example 1100
The plasticizer aromatic hydrocarbons76
(trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.)
The filler is calcium carbonate210
The filler is carbon black100
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
The perlite filler10
(trade name Perlite B-409: Mitsui Mining &Smelting Co., Ltd.)
white black
(trade name SILPHONITE M-1: MIZUSAWA INDUSTRIAL CHEMICALS, LTD.)
the acid-treated clay
(trade name MIZUKA ACE #300: MIZUSAWA INDUSTRIAL CHEMICALS, LTD.)
The catalyst curing dilaurate di-n-butyanova2
Additive γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Table 8
Source materialThe composition of

(mass parts)
The polymer of synthetic example 1100
The plasticizer aromatic hydrocarbons76
(trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.)
The filler is calcium carbonate210
The filler is carbon black110
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
The catalyst curing dilaurate di-n-butyanova2
Additive γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Table 9
Comparative

example 3
Example 7Example 8Example 9
FillerPerliteWhite blackAcid clay
The initial stage
Utverjdaemogo (min)
Viable35455555
Time loss stickiness45556560
The elasticity of N-type (23°7 days)
Tensile strength at break (N/cm2)1281148799
Elongation at break (%)8393104101
Storage base connection 40°, 2 weeks
Utverjdaemogo (min)
Viable15407065
Time loss stickiness40509080
The elasticity of N-type (23°7 days)
Tensile strength n and rupture (N/cm 2)126156114109
Elongation at break (%)534987105
Storage base connection 40°, 4 weeks
Utverjdaemogo (min)
Viable15406060
Time loss stickiness30606565
The elasticity of N-type (23°7 days)
Tensile strength at break (N/cm2)115124105112
Elongation at break (%)383307289

EXAMPLE 10

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 10. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (from what the actual content of the isocyanate 5.4 masses. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. Using the resulting mixture was obtained utverjdenie connection in the form of a rectangular parallelepiped having a length of 8 cm, a width of 3 cm and a height of 1 cm, and measured the hardness (JIS A) of the cured compound. The results of this are shown in table 12.

EXAMPLE 11

The underlying connection was obtained by mixing the polymer of synthetic example 1 with the plasticizer, fillers and additives in amounts shown in table 11. Then mixed 500 masses. parts of this base compound and 50 mass. parts of the urethane prepolymer (the isocyanate content of 5.4 wt. percent)obtained by adding xylylenediisocyanate to polypropylenglycol. Hardness (JIS A) of the cured compounds measured in a manner analogous to the method indicated in example 10 shown in table 12. In example 11 a hardness of 10 or more was found at 23°C for 2 hours, thus can be achieved excellent hardness.

td align="center"> (trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.)
Table 10
Source materialThe composition of

(mass parts)
The polymer of synthetic example 1100
The plasticizer is an aromatic hydrocarbon76
The filler is calcium carbonate210
The filler is carbon black100
(trade name Thermax MT N-990: SHIRAISHI CALCIUM KAISHA, LTD.)
Filler - treated acid clay10
(trade name MIZUKA ACE #300: MIZUSAWA INDUSTRIAL CHEMICALS, LTD.)
The curing catalyst - dilaurate di-n-butyanova2
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

Table 11
Source materialThe composition of

(mass parts)
The polymer of synthetic example 1100
The plasticizer is an aromatic hydrocarbon77,85
(trade name Nisseki Hisol SAS-LH", produced by Nippon Petrochemicals Co., Ltd.)
The filler is calcium carbonate210
The filler is carbon black100
(trade name Thermax MT N-90: SHIRAISHI CALCIUM KAISHA, LTD.)
Filler - treated acid clay10
(trade name MIZUKA ACE #300: MIZUSAWA INDUSTRIAL CHEMICALS, LTD.)
The curing catalyst is Tris(acetylacetone)indium0,15
(trade name Nacem Indium: Called Nihon Sangyo Co., Ltd.)
Additive - γ-glycidoxypropyltrimethoxysilane2
(trade name SH6040: Dow Corning Toray Silicone Co., LTD.)

41
Table 12
Example 10Example 11
The curing catalystTin

Dilaurate dibutylamine
India

Tris(acetylacetone)-Indies
The hardness of the cured compounds (JIS A)
23°2 hoursx17
3 hours425
4 hours830
5 hours1331
6 hours1532
1 day3237
7 days40

Industrial applicability

Cured composition of the present invention has satisfactory storage stability of the base connection and, in addition, satisfactory ability to cure even after storage of the base connection. Utverjdenie connection after curing, has high mechanical strength and, in addition, has a satisfactory tensile strength at break, toughness and barrier properties to gas. So utverjdenie compounds widely used as sealing material for the production of insulating glass, the frames for the Windows of vehicles and the like. In addition, the cured composition of the present invention is also suitable for use as a hermetic composites for constructions, adhesives, coatings and the like.

1. Curing composition for coatings, adhesives, sealing structures, insulating glass and frames of vehicles containing polymer having two or more tylnej groups on the molecule, the compound having two or more isocyanate groups per molecule, carbon black and calcium carbonate, additionally contains a filler, the main ingredient of which is silicic acid or silicate, or additionally contains organic order is tel, the main ingredient is powdered coal.

2. Cured composition according to claim 1, further comprises a filler, the main component of which is silicic acid or a silicate, and an organic filler, the main component of which is powdered coal.

3. Cured composition according to claim 1, in which the filler, the main component of which is silicic acid or silicate is a perlite, white carbon and acid clay.

4. Cured composition according to claim 1, in which the molar ratio (isocyanate groups/tirinya group) of the isocyanate groups in the compound having two or more isocyanate groups in the molecule, to tilenum groups in the polymer having two or more tylnej groups on the molecule is 0.5 to 4.0.

5. Cured composition according to claim 1, which contains 20-200 parts by weight of carbon black relative to 100 parts by weight of the amount of the polymer having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups in a molecule.

6. Cured composition according to claim 1, which contains 0.5 to 50 parts by weight of filler, the main component of which is silicic acid or silicate, relative to 100 parts by weight of the amount of the polymer having two or more tylnej groups per molecule and compounds having the th two or more isocyanate groups in a molecule.

7. Cured composition according to claim 1, which contains 0.5 to 150 parts by weight of an organic filler, the main component of which is powdered coal, relative to 100 parts by weight of the amount of the polymer having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups in a molecule.

8. Cured composition according to claim 1, which contains 10-100 parts by weight of a hydrocarbon plasticizer relative to 100 parts by weight of the amount of the polymer having two or more tylnej groups in the molecule, and compounds having two or more isocyanate groups in a molecule.

9. Cured composition according to claim 1, further comprises ORGANOMETALLIC compound.



 

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