ORGANIC POLYMER, PREPARATION THEREOF, AND CURABLE COMPOSITION COMPRISING SAME

Abstract: A curable composition is prepared from an organic polymer having at least two hydrosilyl groups in its molecule, another organic polymer having at least one alkenyl at least one alkenyl group in its molecule, and a hydrosilylation catalyst. This composition is rapidly curable and excellent in depth curability and gives a cured article having excellent mechanical strengths.

Description: The present invention relates to a curable composition comprising an organic polymer having a hydrosilyl group. Hitherto, various curable liquid compositions which are cured to give rubbery materials have been developed. Among them, a curing system having good depth curability has been developed, which system is prepared by cross-linking a polyorganosiloxane having on the average two or more vinyl groups at a molecular end or in a molecular chain of one molecule with a polyorganohydrogensiloxane having two or more hydrogen atoms bonded to silicon atoms in one molecule. Such system is used as a sealing agent or a potting agent by utilizing its good weather resistance, water resistance and thermal resistance. However, such a system has limited applications because it is expensive, the adhesion property is not good and fungus easily grows. Further, said polyorganosiloxane generally has poor compatability with an organic polymer. When a polyorganohydrogensiloxane and an organic polymer having an alkenyl group are intended to be cured, hydrolysis and a dehydrogenation condensation reaction of the polyorganohydrogensiloxane increase due to phase separation, and sufficient mechanical properties are not achieved because of voids. In patent abstracts of Japan, vol. 8, March 23, 1984 in JP-A-58 217505 a method for increasing the molecular weight of ethylene polymers or ethylene/alpha-olefin copolymers with a silane or siloxane compound having at least two Si-hydrogen bonds is described. US-A-4,520 160 describes a hydrosilylation method for preparing siloxane-oxyalkylene block copolymers by reaction between an organo-hydrogen polysiloxane and an olefinically substituted polyoxyalkylene. EP-A-25 54 40 relates to a curable composition consisting of an alkenyloxysilyl containing an organic polymer, an organosilicon compound having at least two hydrosilyl groups and a catalytic amount of a platinum compound. It is an object of the present invention to overcome the problems indicated above. The invention comprises a curable composition which comprises (C) an organic polymer having in the molecule at least two hydrosilyl groups of formula wherein each R is, same or different, a group selected from H, OSi(CH₃)₃ or an organic group having 1 to 10 carbon atoms, R¹ is a group selected from divalent groups of the formulas: -R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are divalent hydrocarbon groups having 1 to 20 carbon atoms) a is 0 or 1 and wherein m≧1 m+n=2∼50, the backbone of the organic polymer being selected from (meth)acrylate ester polymers, hydrocarbon polymers and polyester polymers, (D) an organic polymer having at least one alkenyl group in the molecule selected from (meth)acrylate ester polymers, hydrocarbon polymers and polyester polymers wherein the backbone is the same as in component (C) and (E) a hydrosilylation catalyst. Polymers having various backbones can be used as the organic polymer having at least two hydrosilyl groups in a molecule that is a polyester polymer, a hydrocarbon polymer and a (meth)acrylate ester polymer. The polyester polymer may have the backbone prepared by, for example, polycondensing a polybasic acid and polyhydric alcohol by a direct esterification, a transesterification or the like. Concretely, the following components may be polycondensed, but the present invention is not restricted to them. Diol Ethylene glycol, propylene glycol, butanediol, hexamethylene glycol, hydrogenated bisphenol A, neopentyl glycol, polybutadienediol, diethylene glycol, triethylene glycol and dipropylene glycol Polyol having at least three hydroxyl groups Glycerol, trimethylolmethane, trimethylolpropane and pentaerythritol Dicarboxylic acid Phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, tetrachlorophthalic acid, polybutadiene dicarboxylic acid, oxalic acid, malonic acid, succinic acid, adipic acid, sebacic acid, maleic acid, fumaric acid and cyclopentane dicarboxylic acid Polycarboxylic acid having at least three carboxyl groups Trimellitic acid, butane tricarboxylic acid, pyromellitic acid Further, anhydrides and acyl halides of the above carboxylic acids can be used in addition to these polybasic carboxylic acids. The backbone of the polyester polymer can be prepared also by a ring opening polymerization of a lactone. Specific examples of the lactone are β-propiolactone, pivalolactone, α-methyl-β-propiolactone, δ-valerolactone, methyl-δ-valerolactone, dimethyl-δ-valerolactone, ε-caprolactone, δ-methyl-ε-caprolactone and dimthyl-ε-caprolactone. The polyester polymer may be a linear or branched one. Specific examples of a monomer component constituting the hydrocarbon polymer are olefins having 2 to 12 carbon atoms, acetylene analogues, conjugated dienes, vinyl ethers, aromatic vinyl compounds and the like. Specific examples of the monomer component are ethylene, acetylene, propylene, 1-butene, 2-butene, isobutylene, 2-methyl-1-butene, 3-methyl-1-butene, pentene, pentyne, 4-methyl-1-pentene, hexene, hexyne, vinylcyclohexane, butadiene, isoprene, chloroprene, cyclopentadiene, methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, styrene, α-methylstyrene, dimethylstyrene, monochlorostyrene, dichlorostyrene, β-pinene, indene and cyclopentadiene. Among them, propylene, 1-butene, 2-butene, isobutylene, butadiene and isoprene are preferable. Various hydrocarbon polymers can be prepared from one or at least two of said monomers by a radical polymerization, an ionic polymerization, a coordination ionic polymerization, a living cationic polymerization (so-called Inifer method) which is proposed by Kennedy et al. When dienes and acetylene derivatives are polymerized, double bonds remain in a backbone chain or a side chain after polymerization and subsequently a hydrosilyl group can be introduced by utilizing the double bonds. When the polymer is used in an application requiring a weather resistance, a hydrogenated polymer may be used. Specific examples of the hydrocarbon polymer are polyisobutylene, ethylene/propylene copolymer, 1,2-polybutadiene, 1,4-polybutadiene, hydrogenated polybutadiene, polyisoprene and hydrogenated polyisoprene, but the hydrocarbon polymer is not restricted to these polymers. The hydrocarbon polymer may be a linear or branched one. Specific examples of a monomer component constituting the (meth)acrylate ester polymer are acrylic acid and acrylate ester monomers such as methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec.-butyl acrylate, tert.-butyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, tridecyl acrylate, stearyl acrylate, cyclohexyl acrylate, benzyl acrylate, tetrahydrofurfuryl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, 2-phenoxyethyl acrylate, ethyl carbitol acrylate, allyl acrylate, glycidyl acrylate, dimethylaminoethyl acrylate, acrylic acid, sodium acrylate, trimethylolpropane triacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate and pentaerythritol triacrylate; and methacrylic acid and methacrylate ester monomers such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, tert.-butyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate, tridecyl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, propyl methacrylate, benzyl methacrylate, isopropyl methacrylate, sec.-butyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate, allyl methacrylate, ethylene glycol methacrylate, triethylene glycol methacrylate, tetraethylene glycol methacrylate, 1,3-butylene glycol methacrylate, trimethylolpropane methacrylate, 2-ethoxyethyl methacrylate, 2-methoxyethyl methacrylate, dimethylaminoethylmethylchloride methacrylate, methacrylic acid and sodium methacrylate. In addition to these (meth)acrylic acid and (meth)acrylate ester monomers, vinyl monomers such as acrylamide, acrylonitrile, vinyl acetate, styrene, ethylene, propylene, isobutylene, butadiene, isoprene and chloroprene can be used as the component of the copolymer. Various (meth)acrylate ester polymers can be prepared from one or at least two of said monomer components by a radical polymerization, an ionic polymerization, a group transfer polymerization (GTP method) proposed by Du Pont. The polymer may be a linear or branched one. The hydrosilyl group contained in the polymer may be in the molecular chain or at the molecular end. When a rubbery cured material is prepared by using the hydrosilyl group-containing organic polymer, the hydrosilyl group at the molecular end is preferable since an effective network chain length is elongated. The hydrosilyl group mentioned in the present invention is generally an arbitrary group which has a Si-H linkage and is not limited. The hydrosilyl group is a group of the formula: wherein X is a group having at least one hydrosilyl group of the formula: (m≧1 m+n=2∼50) (wherein R is the same as described above.), R¹ is a group selected from divalent groups of the formulas: -R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are a divalent hydrocarbon group having 1 to 20 carbon atoms.), and a is 0 or 1. (R=CH₃, C₂H₅, C₆H₅ n=2∼20) (m≧1, m+n+p+q=2∼20) Among the above various hydrosilyl groups, the moiety constituting the hydrosilyl group preferably has a molecular weight of lower than 500, since the organic polymer having the hydrosilyl group has a low possibility to decrease the compatibility with various organic polymers. The following is preferable further in view of reactivity of the hydrosilyl group: Since the reactivity of the polymer (reactivity of the hydrosilyl group) is high and the compatibility with other polymer is good, a group which has a hydrogen atom bonded to a silicon atom and is based on the cyclic polysiloxane is preferable. The number of hydrosilyl groups in one molecule is at least 2, preferably 2 to 15, particularly 3 to 12. In case that the hydrosilyl group-containing organic polymer according to the present invention is mixed with the alkenyl group-containing organic polymer in the presence of the hydrosilylation catalyst so as to give a cured material through the hydrosilylation reaction, the curing tends to be slow and insufficient if the number of the hydrosilyl groups is smaller than 2. When the number of the hydrosilyl groups is larger than 15, the polymer has bad stability and the cured material has a large number of the hydrosilyl groups after the curing which cause voids and cracking. A bonding manner of the hydrosilyl group in the hydrosilyl group-containing organic polymer is not limited. The silicon atom may directly bond to the backbone of the organic polymer, or the carbon atom of the carbon-silicon linkage may bond to the backbone of the organic polymer optionally through a urethane, ester, ether or carbonate linkage. The hydrosilyl group-containing organic polymer preferably has a molecular weight of 500 to 50,000, particularly 500 to 20,000 in view of easy handling, an easy synthesis and compatibility with other polymers. A method for preparing the hydrosilyl group-containing organic polymer is not limited and is arbitrary. For example, the following methods are contemplated: (i) a method which comprises reducing an Si-Cl group to an Si-H group in an organic polymer having the Si-Cl group in the molecule by treating the organic polymer with a reducing agent such as LiAlH₄ or NaBH₄, (ii) a method which comprises reacting an organic polymer having a functional group X in the molecule with a compound having hydrosilyl group and a functional group Y which reacts with the functional group X, (iii) a method which comprises retaining a hydrosilyl group in the molecular chain or on the molecular end of an organic polymer after a reaction by selectively hydrosilylating a polyhydrosilane compound having at least two hydrosilyl groups to an organic polymer having an alkenyl group. In the above method (iii) for preparing the hydrosilyl group-containing organic polymer there is provided a method for preparing an organic polymer having a hydrosilyl group which comprises reacting (A) an organic polymer having at least one alkenyl group in a molecule with (B) a polyvalent hydrogensilicon compound in the presence of a hydrosilylation catalyst so that the hydrosilyl groups remain after the reaction. The polymer used as the component (A) is a polyester polymer, a hydrocarbon polymer or a (meth)acrylate ester polymer. The alkenyl group is not limited, and is preferably a group of the formula: wherein R¹ is a group selected from divalent organic groups of the formulas: -R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are a divalent hydrocarbon group having 1 to 20 carbon atoms.), and a is 0 or 1. The method of introducing the alkenyl group in the organic polymer is not limited. For example, (i) the alkenyl group can be introduced at the molecular end or in the molecular backbone by reacting an organic polymer having a functional group such as a hydroxy group, an alkoxide group or a carboxyl group with an organic compound having an alkenyl group and an active group which is reactive to said functional group. Specific examples of the organic compound having the alkenyl group and the active group which is reactive to said functional group are a C₃-C₂₀ unsaturated aliphatic acid, acid halide and acid anhydride such as acrylic acid, methacrylic acid, vinyl acetate, acrylic chloride and acrylic bromide; a C₃-C₂₀ unsaturated aliphatic acid substituted carbonate halide such as allyl chloroformate (CH₂=CHCH₂OCOCl) and allyl bromoformate (CH₂=CHCH₂OCOBr); allyl chloride, allyl bromide, vinyl(chloromethyl)benzene, allyl(chloromethyl)benzene, allyl(bromomethyl)benzene, allyl chloromethyl ether, allyl(chloromethoxy)benzene, 1-butenyl chloromethyl ether, 1-hexenyl(chloromethoxy)benzene, allyloxy(chloromethyl)benzene and the like. (ii) In the case of the acrylate ester polymer and the like usually prepared by a radical polymerization, the alkenyl group can be introduced in the polymer molecule by using a monomer component having an alkenyl group with a relatively low radical polymerization property such as allyl acrylate or allyl methacrylate. The alkenyl group can be introduced at the molecular end by using, for radical polymerization, a chain transfer agent having an alkenyl group having a relatively low radical polymerization property such as allyl mercaptan. The alkenyl group can be introduced in a polymer molecule by using, as a monomer component, a monomer having a hydroxy group or a carboxyl group such as 2-hydroxylethyl methacrylate or acrylic acid to carry out a polymerization, and then reacting the polymer with an organic compound having an alkenyl group and a functional group which is reactive to said functional group. Specific examples of the organic compound having the alkenyl group and the functional group which is reactive to said functional group are compounds described in method (i). (iii) When a diene or acetylene monomer component is used for the preparation of the hydrocarbon polymer, a double bond which remains after polymerization can be used as the alkenyl group. The alkenyl group of the organic polymer (A) may be present at the molecular end or in the molecular chain. When a rubbery cured material is prepared by using the hydrosilyl group-containing organic polymer, the alkenyl group at the molecular end is preferable since the hydrosilyl group can be introduced on the molecular end and an effective network chain length of the cured material is elongated. The number of the alkenyl groups in one molecule is at least one, preferably 2 to 6. Specific examples of the polyvalent hydrogensilicon compound (B) (m+n=3∼6 m≧2), (n=3∼20) (R=CH₃, C₆H₅, C₂H₅), (1≧2, p+1+m+n=3∼20 R=CH₃, C₂H₅, C₆H₅), The number of hydrosilyl group in one molecule of the polyvalent hydrogensilicon compound (B) is preferably 3 to 16, particularly 4 to 13. Since the hydrosilyl group-containing organic polymer prepared from the component (A) and the component (B) does not deteriorate compatibility, the polyvalent hydrogensilicon compound (B) preferably has a molecular weight of lower than 500. Since a hydrosilylating reaction of the component (A) and component (B) has high reactivity, the following compounds are preferable: Since the compatibility with the alkenyl-group containing organic polymer is generally good, the reactivity with the alkenyl group in the organic polymer is high and unreacted components can be easily removed under a reduced pressure after hydrosilylating reaction, the following compounds are particularly preferable: The hydrosilyl group-containing organic polymer can be prepared by the hydrosilylation reaction of the alkenyl group-containing organic polymer (A) and the polyvalent hydrogensilicon compound (B). Specific examples of a catalyst used for the reaction are platinum as such; solid platinum supported on a carrier such as alumina, silica or carbon black; chloroplatinic acid; a complex of chloroplatinic acid with an alcohol, an aldehyde or a ketone; a platinum-olefin complex (for example, Pt(CH₂=CH₂)₂(PPh₃)₂Pt(CH₂=CH₂)₂Cl₂); a platinum-vinylsiloxane complex (for example, Pt n (ViMe₂SioSiMe₂Vi) m , Pt[(MeVisio)₄] m ); a platinum-phosphine complex (for example, Pt(PPh₃)₄, Pt(PBu₃)₄); a platinum-phosphite complex (for example, Pt[P(OPh)₃]₄, Pt[P(OBu)₃]₄) (wherein Me is a methyl group, Bu is a butyl group, Vi is a vinyl group, Ph is a phenyl group, and n and m are an integer.); dicarbonyldichloroplatinum; a platinum-hydrocarbon complex described in U.S. Patent Nos. 3,159,601 and 3,159,662 to Ashby; and a platinum alcoholate catalyst described in U.S. Patent No. 3,220,972 to Lamoreaux. In addition, a platinum chloride-olefin complex described in U.S. Patent No. 3,516,946 to Modic is also useful in the present invention. Specific examples of the catalyst other than the platinum compounds are RhCl(PPh₃)₃, RhCl₃, Rh/Al₂O₃, RuCl₃, IrCl₃, FeCl₃, AlCl₃, PdCl₂·2H₂O, NiCl₂ and TiCl₄ (Ph is a phenyl group.). Only one catalyst or a combination of at least two catalysts may be used. In view of catalytic activity, chloroplatinic acid, the platinum-olefin complex, the platinum-vinylsiloxane complex and the like are preferable. An amount of the catalyst is not limited, but 10⁻¹ to 10⁻⁸ mol, based on the alkenyl group of the component (A), may be used. The range between 10⁻³ and 10⁻⁶ mol is preferable. The use of a solvent is not necessarily required in the hydrosilylating reaction. An inert organic solvent may be used when the starting materials have a high viscosity and it is difficult to carry out an operation such as a stirring. Specific examples of the inert organic solvent are aromatic hydrocarbon solvents such as benzene, toluene and xylene; aliphatic hydrocarbon solvents such as hexane and octane; ether solvents such as ethyl ether and butyl ether; ketone solvents such as methyl ethyl ketone; halogenated hydrocarbon solvents such as trichloroethylene. A manner for adding the component (A), the component (B) and the hydrosilylation catalyst is not limited and includes charging three components simultaneously, adding the component (A) and the hydrosilylation catalyst to the component (B), adding the component (B) to the component (A) and the hydrosilylation catalyst, adding the component (A) to the component (B) and the catalyst, and adding each component simultaneously. In order to carry out the reaction so that the hydrosilyl group remains after the reaction, preferably the polyvalent hydrogensilicon compound is always present in excess to the component (A). Therefore, it is preferable to add a mixture of the alkenyl group-containing organic polymer (A) and the hydrosilylation catalyst to the polyvalent hydrogensilicon compound (B). The reaction temperature may be from 0 to 200°C, preferably from 50 to 150°C. When the reaction temperature is lower than 0°C, a catalyst activity is insufficient and therefore a reaction rate is low. When it is higher than 200°C, the catalyst is often deactivated. In the hydrosilylating reaction, under any reaction conditions, at least two hydrosilyl groups of a part of polyvalent hydrogensilicon compound react with the alkenyl groups of the component (A) and a phenomenon such as the viscosity increase caused by the molecular weight increase is sometimes observed. Since the hydrosilyl group-containing organic polymer prepared by the above method usually contains the hydrosilylating catalyst after the reaction, its stability is generally poor. When the organic polymer is kept standing for a long time or exposed to the moisture, an Si-H group converts to an Si-OH group and a phenomenon such as the viscosity increase or the gelation is observed. Therefore, the catalyst is preferably removed from the polymer after the hydrosilylating reaction. Specific examples for a method for removing the catalyst are a method which comprises mixing a reaction solution after the polymerization with silica, silica gel, an ion exchange resin or the like or treating the reaction solution with a column comprising the same, and a method which comprises washing a reaction mixture with a neutral or weakly acidic aqueous solution. The hydrosilyl group-containing organic polymer prepared in this manner generally has better compatibility with an organic polymer, particularly of the same kind, in comparison with known hydrosilyl group-containing polysiloxanes. When the hydrosilyl group-containing organic polymer is mixed with the alkenyl group-containing organic polymer in the presence of said various hydrosilylation catalysts and then cured, a homogeneous cured material can be obtained without a phenomenon such as foaming since these polymers have good compatibility. The curing conditions are not limited. In general, the curing can be carried out at 0 to 200°C, preferably 50 to 150°C for 10 seconds to 4 hours. At a high temperature of 80 to 150°C, the curing is sometimes completed for a short time of 10 seconds to 30 minutes. For example, even if the cured material prepared according to said method has a thickness of at least 1 cm, the homogeneously cured material having good depth curability can be obtained. Properties of the cured material depend on the backbone and the molecular weight of the organic polymers. A rubbery material to a resinous material can be prepared. When the cured material is prepared, various solvents, plasticizers, fillers, pot-life extending agents, pigments, age resistors, ultraviolet light absorbers and adhesives can be used in addition to three main components of the hydrosilylation catalyst, the hydrosilyl group-containing organic polymer and the alkenyl group-containing organic polymer. Various hydrosilyl group-containing polyester, hydrocarbon and (meth)acrylate ester polymers which are described before can be used as the organic polymer (C) having at least two hydrosilyl groups. Preferable molecular weight and backbone of said polymer, preferable structure of the hydrosilyl group, preferable number of the hydrosilyl groups per one molecule and preferable linkage site to backbone of the hydrosilyl group are the same as described before. Various alkenyl group-containing organic polymers, namely polyesters, hydrocarbon and (meth)acrylate ester polymers which are the component (A) described before can be used as the organic polymer (D) having at least one alkenyl group. A method for introducing the alkenyl group into the organic polymer (D) may be a conventionally proposed method and is roughly classified in a method for introducing the alkenyl group after the polymerization and a method for introducing the alkenyl group during the polymerization. The method for introducing the alkenyl group after the polymerization includes, for example, a method comprising reacting an organic polymer having a functional group such as a hydroxy group, an alkoxide group or a carboxyl group at the molecular end, in the backbone or in the side chain, with an organic compound having an alkenyl group and an active group which is reactive to said functional group so as to introduce the alkenyl group at the molecular end, in the backbone or in the side chain. Specific examples of the organic compound having the alkenyl group and the active group which is reactive to said functional group are a C₃-C₂₀ unsaturated aliphatic acid, acid halide and acid anhydride such as acrylic acid, methacrylic acid, vinyl acetate, acrylic chloride and acrylic bromide; a C₃-C₂₀ unsaturated aliphatic acid substituted carbonate halide such as allyl chloroformate (CH₂=CHCH₂OCOCl) and allyl bromoformate (CH₂=CHCH₂OCOBr); allyl chloride, allyl bromide, vinyl(chloromethyl)benzene, allyl(chloromethyl)benzene, allyl(bromomethyl)benzene, allyl chloromethyl ether, allyl(chloromethoxy)benzene, 1-butenyl chloromethyl ether, 1-hexenyl(chloromethoxy)benzene and allyloxy(chloromethyl)benzene. The method for introducing the alkenyl group during the polymerization includes, for example, a method comprising introducing the alkenyl group in the backbone or at the molecular end of the polymer by using a vinyl monomer which has an alkenyl group having a low radical reactivity in the molecule such as allyl methacrylate and allyl acrylate, or a radical chain transfer agent which has an alkenyl group having a low radical reactivity such as allyl mercaptan when the organic polymer (D) is prepared by a radical polymerization. A molecular weight of the component (D) is preferably from 500 to 50,000, more preferably from 500 to 20,000 in view of the properties of the cured material and the compatibility with the component (C). The number of the alkenyl groups present in one molecule is preferably from 1 to 10, particularly from 2 to 5. When a rubbery cured material is prepared from components (C), (D) and (E), the alkenyl group of the component (D) is preferably present on the molecular end since the effective network chain length of the cured material is elongated. The molar ratio of the hydrosilyl group to the alkenyl group in the components (C) and (D) is preferably from 0.2 to 5.0, more preferably from 0.4 to 2.5. When the molar ratio is smaller than 0.2, the curing is insufficient and only a sticky cured material having low strength is obtained. When the molar ratio is larger than 5.0, the cracking and voids occur and a homogeneous cured material having high strength cannot be obtained since many active hydrosilyl groups remain in the cured material after the curing. The hydrosilylation catalyst (E) according to the present invention is not limited and is arbitrary. Concretely, the same catalyst as used in the preparation of the hydrosilyl group-containing organic polymer can be used. One of these catalysts may be used or a combination of at least two of these catalysts may be used. Chloroplatinic acid, platinum-olefin complex and platinum-vinylsiloxane complex are preferable in view of the catalyst activity. A catalyst amount is not limited, but it is preferably from 10⁻¹ to 10⁻⁸ mol based on 1 mol of the alkenyl group of the component (D). 10⁻³ to 10⁻⁶ mol is more preferable. The homogeneous cured material having good depth curability without a phenomenon such as the foaming can be obtained by mixing the components (C), (D) and (E) and effecting the curing. Curing conditions are not limited, but the curing is generally carried out at 0 to 200°C, preferably 30 to 150°C for 10 seconds to 4 hours. In particular, at a high temperature of 80 to 150°C, the curing is sometimes completed for a short time of 10 seconds to 1 hour. Properties of the cured material depend on the backbone and the molecular weight of the polymers (C) and (D), and a rubbery material to a resinous material can be prepared. When the cured material is prepared, various solvents, adhesion improving agents, property controlling agents, preservation stability improving agents, plasticizers, fillers, age resistors, ultraviolet light absorbers, metal inactivating agents, antiozonants, light stabilizers, amine-based radical chain inhibiting agents, phosphorus-based peroxide decomposers, lubricants, pigments, foaming agents and the like can suitably be added according to the desired application in addition to the three essential components (C), (D) and (E). When the composition according to the present invention is used, a homogeneous organic cured material having good mechanical properties, high curing speed and good depth curability is obtained. [Examples] The present invention is explained in the Examples, but it is not limited to the Examples. Preparative Example 1 In a round-bottom flask equipped with a stirring rod, a thermometer, a dropping funnel, a nitrogen introducing tube and a condenser, 300 g (0.1 mol) of hydroxy group-terminated polycaprolactone (a number average molecular weight: 3,000, a hydroxy group equivalent: 1,500), 24.0 g of pyridine, and 300 ml of THF were charged. 32 Grams of allyl chloroformate was slowly dropwise added from the dropping funnel at a room temperature. Then, the mixture was heated to 50°C and stirred for 3 hours. After a resulted salt was removed by filtration, 150 ml of toluene was added and the mixture was washed with 200 ml of aqueous hydrochloric acid and neutralized and condensed to obtain allyl-terminated polycaprolactone. The resulted oligomer had a number average molecular weight of 3,200 according to a VPO measurement. A 300 MHz NMR of an olefin portion confirmed the introduction of the allyl group. The quantification of the olefin by an iodometric titration confirmed that the number of allyl-type unsaturated groups introduced in one molecule was 2.0 on the average. Preparative Example 2 To 300 g of hydrogenated polyisoprene having a hydroxy group at both ends (Epol (trade name) manufactured by Idemitsu Sekiyu Kagaku Kabushiki Kaisha), 50 ml of toluene was added and the dehydration was curried out with azeotropy. A solution of t-BuOK (48 g) in THF (200 ml) was injected. After the reaction was carried out at 50°C for 1 hour, 47 ml of allyl chloride was dropwise added over about 30 minutes. After the addition was completed, the reaction was carried out at 50°C for 1 hour. After the reaction was completed, 30 g of aluminum silicate was added to the reaction solution so as to absorb a resulted salt and then the mixture was stirred at a room temperature for 30 minutes. Through filtration and purification, about 250 g of allyl-terminated hydrogenated polyisoprene was obtained as a viscous liquid. A 300 MHz ¹H-NMR analysis confirmed that the allyl group was introduced at 92 % of the ends. The molar number of the olefin determined according to the iodine value was 0.1072 mol/100 g. A viscosity according to an E-type viscometer was 302 poises (23°C). Typical properties of Epol (from a technical brochure) Hydroxy group content (meq/g) 0.90 Viscosity (poise/30°C) 700 Average molecular weight (measured by VPO) 2,500 Preparative Example 3 An agitating blade, a three-way cock and a vacuum line were attached to a one liter pressure-resistant glass autoclave, and the polymerization vessel was dried by heating it at 100°C for one hour while evacuating through the vacuum line. After cooling it to a room temperature, a nitrogen gas was introduced to reach an atmospheric pressure by means of the three-way cock. Then, 400 ml of 1,1-dichloroethane (main solvent) dried by a calcium hydride treatment was introduced in the autoclave from one inlet of the three-way cock by means of an injector while flowing the nitrogen gas. 200 ml of nitroethane (additional solvent) dried by a calcium chloride treatment was introduced and then a solution of TCC (20 mmol, tricumyl chloride: in 1,1-dichloroethane (100 ml) was added. Subsequently, a pressure-resistant glass-made liquefied gas sampling tube equipped with a needle valve which contained 70 g of isobutylene dehydrated by passing through a column filled with barium oxide was connected with the three-way cock, and then the vessel was immersed in a dry ice-acetone bath at a temperature of -70°C and the content of the polymerization vessel was cooled for 1 hour while stirring. After cooling, the internal space of the vessel is evacuated through the vacuum line, and then the needle valve was opened to introduce isobutylene in the polymerization vessel from the pressure-resistant glass-made liquefied gas sampling tube. Then, the internal space was returned to an atmospheric pressure by flowing the nitrogen gas from one outlet of the three-way cock, the cooling was kept for 1 hour with stirring and the content in the vessel was cooled to -60°C. Then, 32 g (100 mmol) of TiCl₄ was added through the three-way cock by means of an injector to initiate the polymerization, and, after 60 minutes, 100 mmol of allyltrimethylsilane previously cooled to below 0°C was added. Then, the temperature was gradually raised to a room temperature while stirring and the reaction was completed by adding methanol. Then, the reaction mixture was transferred to an egg-plant type flask, and unreacted isobutylene, 1,1-dichloroethane, nitroethane, allyltrimethylsilane and methanol were distilled off. After a remaining polymer was dissolved in 500 ml of n-hexane, the washing of the solution with water was repeated until this solution become neutral. Then, an n-hexane solution was concentrated to 200 ml and the concentrated solution was poured in 2 liters of acetone to precipitate the polymer. The obtained polymer was dissolved again in 500 ml of n-hexane, and the solution was dried with anhydrous magnesium sulfate and filtered. n-Hexane was distilled off under vacuum to obtain an allyl group-terminated isobutylene polymer. An yield was calculated from an amount of the obtained polymer. and / were determined by a GPC method. The terminal structure was determined by measuring and comparing the strength of resonance signal of proton assigned to each structure by means of ¹H-NMR (300 MHz). Yield: 90 % (65 g) = 3,800, / = 1.20 The number of allyl groups per one molecule = 3.0 Preparative Example 4 A one liter four-necked flask equipped with a stirring rod, a dropping funnel, a thermometer, a three-way cock and a condenser was used. In the flask, 20 ml of toluene was charged under a nitrogen atmosphere. A monomer solution in toluene consisting of 25.6 g of n-butyl acrylate, 2.52 g of allyl methacrylate, 0.81 g of n-dodecyl mercaptan, 1.0 g of azobisisobutyronitrile and 100 ml of toluene was dropwise added over about one hour from the dropping funnel while refluxing toluene. After the addition was completed, the reaction was continued for 2 hours. After the toluene solution was treated with aluminum silicate, it was filtered with suction by using a filtering aid (diatomaceous earth) to give a substantially transparent solution. The solution was evaporated and further dried under a reduced pressure at 80°C for 3 hours to give about 26 g of a pale yellow viscous liquid oligomer. A molar number of the allyl group in the polymer was 0.154 mol/100 g according to the iodometric titration. A molecular weight was 3,900 according to a VPO. The molecular weight and the molar number of the allyl group according to the iodometric titration revealed that about 6 allyl groups on the average were introduced in one molecule of the polymer. Example 1 A 300 ml four-necked flask equipped with a stirring rod, a dropping funnel, a thermometer, a three-way cock and a condenser was used. In the flask, 34.55 g (0.1435 mol) of a cyclic polysiloxane: (LS 8600 manufactured by Shin-Etsu Chemical Co., Ltd.) was charged under a nitrogen atmosphere. A toluene solution consisting of 100 g of polycaprolactone prepared in Preparative Example 1 which has 2.0 allyl groups on the average in one molecule (molar number of the olefin: 0.0575 mol), 100 ml of toluene and 60 µl of a solution of chloroplatinic acid catalyst (a solution in which H₂PtCl₆·6H₂O (1 g) is dissolved in ethanol (1 ml) and 1,2-dimethoxyethane (9 ml)) was charged in the dropping funnel. The flask was heated to 70°C and the toluene solution was dropwise added over 2 hours. After the addition was completed and the stirring was continued at 80°C for 5 hours, the remaining allyl group in the reaction solution was determined by IR spectra analysis. The disappearance of carbon-carbon double bond peak at 1645 cm⁻¹ was confirmed. Then, for removal of the catalyst remaining in the reaction system, 10 g of silica gel (Wakogel C-200 manufactured by Wako Junyaku Kabushiki Kaisha) was added at room temperature and the mixture was stirred for 2 hours and filtered with a flash column. For removing toluene and unreacted excessive cyclic polysiloxane, the filtrate was evaporated and the degassing under vacuum was carried out at 80°C for 3 hours to give a colorless transparent viscous liquid. The hydrosilyl group in polycaprolactone was confirmed as the strong peak of 2150 cm⁻¹ according to the IR spectra. By comparing the peak intensity of combined Si-C H ₃ and SiC H ₂- with that of the Si- H in 300 MHz NMR spectra, it was revealed that 1.05 hydrosilyl groups on the average per one molecule of said cyclic polysiloxane had been consumed. Namely, the polymer is a polycaprolactone having an increased molecular weight because of cyclic hydrogenpolysiloxane and having the following molecular end: Example 2 A 300 ml four-necked flask equipped with a stirring rod, a dropping funnel, a thermometer, a three-way cock and a condenser was used. In the flask, 31.5 g (0.131 mol) of a cyclic polysiloxane: (LS 8600 manufactured by Shin-Etsu Chemical Co., Ltd.) was charged under a nitrogen atmosphere. A toluene solution consisting of 50 g of hydrogenated polyisoprene prepared in Preparative Example 2 in which 92 % of molecular ends have allyl group (molar number of the olefin: 0.0536 mol), 50 ml of toluene and 60 µl of a solution of chloroplatinic acid catalyst (a solution in which H₂PtCl₆·6H₂O (1 g) is dissolved in ethanol (1 ml) and 1,2-dimethoxyethane (9 ml)) was charged in the dropping funnel. The flask was heated to 70°C and the toluene solution was dropwise added over 2 hours. After the addition was completed and the stirring was continued at 80°C for 5 hours, the remaining allyl group in the reaction solution was determined by IR spectra analysis. The disappearance of carbon-carbon double bond peak at 1645 cm⁻¹ was confirmed. Then, for removal of the catalyst remaining in the reaction system, 5 g of silica gel (Wakogel C-200 manufactured by Wako Junyaku Kabushiki Kaisha) was added at a room temperature and the mixture was stirred for 2 hours and filtered with a flash column. For removing toluene and unreacted excessive cyclic polysiloxane, the filtrate was evaporated and the degassing under vacuum was carried out at 80°C for 3 hours to give a colorless transparent viscous liquid. A viscosity was 514 poises (23°C) according to an E-type viscometer. The hydrosilyl group in hydrogenated polyisoprene was confirmed as the strong peak of 2150 cm⁻¹ according to the IR spectra. By comparing the peak intensity of combined Si-C H ₃ and SiC H ₂- with that of the Si- H in 300 MHz NMR spectra, it was revealed that 1.2 hydrosilyl groups on the average per one molecule of said cyclic polysiloxane had been consumed. Namely, the polymer is hydrogenated polyisoprene having an increased molecular weight because of cyclic hydrogenpolysiloxane and having the following molecular end: Example 3 A 300 ml four-necked flask equipped with a stirring rod, a dropping funnel, a thermometer, a three-way cock and a condenser was used. In the flask, 20.0 g (0.083 mol) of a cyclic polysiloxane: (LS 8600 manufactured by Shin-Etsu Chemical Co., Ltd.) was charged under a nitrogen atmosphere. A toluene solution consisting of 38 g of polyisobutylene prepared in Preparative Example 3 which has three allyl end groups per one molecule (molar number of the olefin: 0.003 mol), 100 ml of toluene and 50 µl of a solution of chloroplatinic acid catalyst (the same as in Example 2) was charged in the dropping funnel. The flask was heated to 70°C and the toluene solution was dropwise added over 3 hours. After the addition was completed and the stirring was continued at 80°C for 1 hour, the remaining allyl group in the reaction solution was determined by means of IR spectra analysis. The disappearance of carbon-carbon double bond peak at 1638 cm⁻¹ was confirmed. Then, the content in the flask was transferred to a 300 ml ground-glass egg-plant flask and the degassing under vacuum was carried out at 80°C for 3 hours so that toluene and excess cyclic polysiloxane was removed to give colorless transparent viscous liquid. An yield was calculated from an amount of the obtained polymer. and / were determined by means of a GPC method. The terminal structure was determined by measuring and comparing the strength of resonance signal of proton assigned to each structure by means of ¹H-NMR (300 MHz). Yield: 96 % (43 g) = 3,900, / =1.25 The number of Si groups per one molecule = 2.9 Namely, the polymer is SiH-terminated polyisobutylene having the following structure: (n = about 20). Example 4 A 200 ml four-necked flask equipped with a stirring rod, a dropping funnel, a thermometer, a three-way cock and a condenser was used. In the flask, 9.26 g (38.5 mmol) of a cyclic polysiloxane: (LS 8600 manufactured by Shin-Etsu Chemical Co., Ltd.) and 20 ml of toluene were charged under a nitrogen atmosphere. A toluene solution in which 10 g of allyl group-containing acrylate ester polymer prepared in Preparative Example 4 and 16 µl of a solution of chloroplatinic acid catalyst (a solution in which H₂PtCl₆·6H₂O (1 g) is dissolved in ethanol (1 ml) and 1,2-dimethoxyethane (9 ml)) were dissolved in 30 ml of toluene was charged in the dropping funnel. The flask was heated to 70°C and the toluene solution was dropwise added over 1 minute. After the addition was completed, the reaction was continued at 80°C for 2 hours. At this time, the remaining allyl group in the reaction solution was determined by means of IR spectra analysis. The disappearance of carbon-carbon double bond peak at 1645 cm⁻¹ was confirmed. Then, for removal of the catalyst remaining in the reaction system, 2 g of silica gel (Wakogel C-200 manufactured by Wako Junyaku Kabushiki Kaisha) was added and the reaction mixture was stirred at room temperature for 30 minutes and filtered with a flash column. For removing toluene and unreacted excessive cyclic polysiloxane, the filtrate was evaporated and the degassing under vacuum was carried out at 80°C for 3 hours to give a colorless transparent viscous liquid. The hydrosilyl group in the acrylate ester polymer was confirmed as the strong peak of 2150 cm⁻¹ according to the IR spectra. By comparing the peak intensity of combined Si-C H ₃ and SiC H ₂ with that of the Si- H in 300 MHz NMR spectra, it was revealed that 1.10 hydrosilyl groups on the average per one molecule of said cyclic polysiloxane had been consumed. Namely, the polymer is a hydrosilyl group-containing acrylate ester polymer which has an increased molecular weight because of cyclic hydrogenpolysiloxane and has the following structure: ( represents a polymer backbone.). Example 5 1.00 Grams of allyl ether-terminated polycaprolactone prepared in Preparative Example 1, 0.40 g of hydrosilyl group-containing polycaprolactone prepared in Example 1 and an amount indicated in Table 1 of chloroplatinic acid catalyst solution used in Example 1 were intimately mixed. A part of the mixture was transferred on a gelation testing device (manufactured by Nisshin Kagaku Kabushiki Kaisha) and a snap-up time (the time which is required for forming a rubbery elastomer) was measured at a given temperature. Results are shown in Table 1. The composition cured rapidly at a high temperature. Amount of catalyst (µl) Temperature 80°C 100°C 120°C 0.30 1′24″ 0′29″ 0′18″ 1.49 1′08″ 0′20″ 0′15″ 2.97 0′53″ 0′18″ 0′14″ Example 6 7.20 Grams of allyl ether-terminated polycaprolactone prepared in Preparative Example 1, 2.88 g of hydrosilyl group-containing polycaprolactone prepared in Example 1 (The molar ratio of the hydrosilyl group to the allyl group was 1 according to NMR spectra.) and 2.1 µl of chloroplatinic acid catalyst solution used in Example 1 were intimately mixed with stirring. The mixture was defoamed by a centrifugal separation and cast in a mold made of polyethylene. The defoaming was again carried out at a room temperature under a reduced pressure, and the mixture was cured at 100°C for 30 minutes to obtain a homogeneous rubbery cured material having a thickness of about 3 mm. A No. 3 dumbbell according to JIS K 6301 was punched off from the sheet of cured material, and a tensile test was curried out at a tensile speed of 200 mm/min. E B was 400 % and T B was 4.2 kg/cm². The cured material exhibiting a rubbery elasticity was obtained for a short time of 30 minutes. Comparative Example 1 A cured material was prepared in the same manner as in Example 6 except that 0.965 g of a polymethylhydrodimethylsiloxane copolymer (average molecular weight: about 2,000 to 2,100, PS 123 manufactured by Chisso Kabushiki Kaisha) of the formula: (n=65∼70%) (the molar number of olefin of the polymer determined from a iodine value was the same as that of the hydrosilyl group of said polysiloxane.) was used in stead of hydrosilyl group-containing polycaprolactone prepared in Example 1. Said hydrogenpolysiloxane had poor compatibility with said allyl ether-terminated polycaprolactone, and the mixture was opaque. Many foams remained after the defoaming under a reduced pressure. Only a cured material containing many foams was obtained and a tensile test cannot be curried out. Example 7 10.0 Grams of allyl ether-terminated polycaprolactone prepared in Preparative Example 1, 4.0 g of hydrosilyl group-containing polycaprolactone prepared in Example 1 (the molar ratio of the hydrosilyl group to the allyl group was 1.) and 3 µl of a chloroplatinic acid catalyst solution used in Example 1 were intimately mixed with stirring. The mixture was defoamed by a centrifugal separation and cast in a mold having a size of 6 cm (length) x 0.8 cm (width) x 1.8 cm (depth). The defoaming was again carried out at a room temperature under a reduced pressure, and the mixture was cured at 100°C for 30 minutes to obtain a rubbery cured material having a thickness of 13 mm. A hardness (Shore A hardness) was measured according to a hardness measuring method defined in a spring-method hardness test (A type) in JIS K 6301, paragraph 5-2. The cured material had a hardness of 20 on the obverse and a hardness of 18 on the reverse. This result reveals that the sample having good depth curability was obtained. Example 8 1.00 Grams of allyl ether-terminated hydrogenated polyisoprene prepared in Preparative Example 2, an amount indicated in Table 2 of hydrosilyl group-containing hydrogenated polyisoprene prepared in Example 2 and 0.5 µl of a chloroplatinic acid catalyst solution used in Example 2 were intimately mixed. A part of the mixture was transferred on a gelation testing device (manufactured by Nisshin Kagaku Kabushiki Kaisha) and a snap-up time (the time which is required for forming a rubbery elastomer) was measured at a given temperature. Results are shown in Table 2. Amount of polymer of Example 2 (g) Molar ratio of hydrosilyl group to allyl group Measuring temperature 80°C 100°C 120°C 0.087 0.25 14′00″ 4′46″ 1′36″ 0.17 0.50 6′26″ 1′37″ 0′34″ 0.33 1.0 3′45″ 0′53″ 0′23″ 0.50 1.5 2′49″ 0′49″ 0′23″ 0.66 2.0 3′16″ 0′51″ 0′20″ 0.99 3.0 2′36″ 1′00″ 0′28″ 1.65 5.0 5′04″ 1′47″ 0′41″ The composition cured rapidly at a high temperature. Example 9 45.0 grams of allyl ether-terminated hydrogenated polyisoprene prepared in Preparative Example 2, 15.0 g of hydrosilyl group-containing polyisoprene prepared in Example 2 (the molar ratio of the hydrosilyl group to allyl group was 1 according to NMR spectra.) and 25 µl of chloroplatinic acid catalyst solution used in Example 2 were intimately mixed with stirring. The mixture was defoamed by a centrifugal separation and cast in a mold made of polyethylene. The defoaming was again carried out at a room temperature under a reduced pressure, and the mixture was cured at 100°C for a given time to obtain a homogeneous rubbery cured material having a thickness of about 3 mm. A No. 3 dumbbell test piece according to JIS K 6301 was punched off from the sheet of the cured material, and a tensile test was curried out at a tensile speed of 200 mm/min. Results are shown in Table 3. The rubbery cured material exhibiting stable tensile properties was obtained in a short time of from 30 minutes to 1 hour. Curing time (min) M₁₀ kg/cm² M₃₀ kg/cm² M₅₀ kg/cm² T B kg/cm² E B % 10 0.8 1.7 2.6 3.4 80 15 0.6 1.5 2.1 2.9 83 30 1.2 2.7 3.9 5.2 66 45 1.4 3.0 4.5 5.5 60 60 1.2 2.9 4.3 6.0 80 90 1.0 2.8 4.0 5.2 70 120 1.2 3.0 4.1 5.5 75 Comparative Example 2 A cured material was prepared in the same manner as in Example 9 except that 3.64 g of a polymethylhydrodimethylsiloxane copolymer (average molecular weight: about 2,000 to 2,010, PS 123 manufactured by Chisso Kabushiki Kaisha) of the formula: (n=65∼70%) (the molar number of the olefin of the polymer of Preparative Example 2 determined from a iodine value was the same as that of the hydrosilyl group of said polysiloxane.) was used in stead of hydrosilyl group-containing polyisoprene prepared in Example 2. Said hydrogensiloxane had poor compatibility with said allyl ether-terminated hydrogenated polyisoprene, and the mixture was opaque. Much foaming occurred after the defoaming under a reduced pressure. Only a cured material having bad mechanical properties and containing many foams was obtained. A tensile test cannot be carried out. Example 10 9.10 Grams of allyl ether-terminated hydrogenated polyisoprene prepared in Preparative Example 3, 3.03 g of hydrosilyl group-containing hydrogenated polyisoprene prepared in Example 2 (the molar ratio of the hydrosilyl group to the allyl group was 1.) and 5 µl of a chloroplatinic acid catalyst solution used in Example 2 were intimately mixed with stirring. The mixture was defoamed by a centrifugal separation and cast in a mold having a size of 6 cm (length) x 0.8 cm (width) x 1.8 cm (depth). The defoaming was again carried out at a room temperature under a reduced pressure, and the mixture was cured at 100°C for 30 minutes to obtain a rubbery cured material having a thickness of 13 mm. The hardness (Shore A hardness) was measured according to a hardness measuring method defined in a spring-method hardness test (A type) in JIS K 6301, paragraph 5-2. The cured material had a hardness of 36 on the obverse and a hardness of 38 on the reverse. The sample having good depth curability was obtained. Example 11 3 Grams of allyl-terminated polyisobutylene prepared in Preparative Example 3, 1 g of SiH-terminated polyisobutylene prepared in Example 3 and 0.5 µl of a chloroplatinic acid catalyst solution used in Example 3 were intimately mixed with stirring. A part of the mixture was transferred on a gelation testing device and a snap-up time was measured in the same manner as in Example 5. The snap-up time was 50 seconds at 100°C. After the mixture was cast in a mold having a thickness of 3 mm, it was heated in an oven at 100°C for 5 minutes to obtain a homogeneous rubbery cured material. A No. 3 dumbbell test piece according to JIS K 6301 was punched off from the sheet of the cured material, and a tensile test was curried out at a pulling speed of 200 mm/min. M₅₀ was 3.8 kg/cm², T B was 5.1 kg/cm² and E B was 70 %. The rubbery cured material having a tack-free surface and exhibiting stable tensile properties was obtained for a short time of a few minutes. Example 12 The same composition used in Examples 11 was cast in a polyethylene sample tube having a diameter of about 1.5 cm and a length of about 10 cm. The composition was defoamed by a centrifugal separation and then cured at 100°C for 10 minutes. After the curing, the polyethylene sample tube was cut at a bottom portion and cut surfaces were observed. The homogeneous curing was effected. Example 13 30 Grams of ally] group-containing acrylate ester polymer prepared in preparative Example 4, 10 g of hydrosilyl group-containing acrylate ester polymer prepared in Example 4 and 50 µl of a chloroplatinic acid catalyst solution used in Example 4 were intimately mixed with stirring. The mixture was defoamed by a centrifugal separation and cast in a mold made of polyethylene. The defoaming was again carried out at a room temperature under a reduced pressure, and then the mixture was cured at 100°C for 30 minutes to obtain a homogeneous transparent rubbery elastic material. Example 14 The same composition used in Example 13 was cast in a mold having a thickness of about 18 mm. In the same manner, the composition was defoamed at room temperature under a reduced pressure and then cured at 100°C for 30 minutes. A homogeneous rubbery elastic material having a thickness of about 13 mm was obtained. The hardness of the obverse was 32 (Shore A hardness) and the hardness of the reverse was 31 (Shore A hardness). An internal part also cured homogeneously. Comparative Example 3 A cured material was prepared in the same manner as in Example 13 except that 10.8 g of a polymethylhydrodimethylsiloxane copolymer (average molecular weight: about 2,000 to 2,100, PS 123 manufactured by Chisso Kabushiki Kaisha) of the formula: (n=65∼70%) was used in stead of hydrosilyl group-containing acrylate ester polymer prepared in Example 4. Said hydrogenpolysiloxane had poor compatibility with said allyl group-containing acrylate ester polymer, and the mixture was opaque. Many foams remained after the defoaming under a reduced pressure. Only a cured material containing many foams was obtained, and a tensile test cannot be carried out.

Claims: A curable composition which comprises (C) an organic polymer having in the molecule at least two hydrosilyl groups of formula wherein each R is, same or different, a group selected from H, OSi(CH₃)₃ or an organic group having 1 to 10 carbon atoms, R¹ is a group selected from divalent groups of the formulas: -R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are divalent hydrocarbon groups having 1 to 20 carbon atoms) a is 0 or 1 and wherein m≧1 m+n=2∼50, the backbone of the organic polymer being selected from (meth)acrylate ester polymers, hydrocarbon polymers and polyester polymers, (D) an organic polymer having at least one alkenyl group in the molecule selected from (meth)acrylate ester polymers, hydrocarbon polymers and polyester polymers wherein the backbone is the same as in component (C) and (E) a hydrosilylation catalyst. The composition according to claim 1, wherein the component (C) has a molecular weight of from 500 to 50,000, the component (D) has a molecular weight of from 500 to 50,000, and a molar ratio of the hydrosilyl group of the component (C) to the alkenyl group of the component (D) is from 0.2 to 5.0. The composition according to claim 1, wherein the component (C) is a hydrosilyl group-containing organic polymer which has a molecular weight of from 500 to 50,000 and has, in the molecular chain or at the molecular end, at least one hydrosilyl group of the formula: wherein X is a group selected from the group consisting of: (wherein p and q is 0 or a positive integer provided that 2 ≦ p + q ≦ 4.), R¹ is a group selected from divalent groups of the formulas: R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are divalent hydrocarbon groups having 1 to 20 carbon atoms.), and a is 0 or 1. The composition according to claim 1, wherein the hydrosilyl group-containing organic polymer (C) is a polyester polymer. The composition according to claim 4, wherein the hydrosilyl group-containing organic polymer (C) is a polymer which mainly comprises an aliphatic polyester. The composition according to claim 1, wherein the hydrosilyl group-containing organic polymer (C) is a hydrocarbon polymer. The composition according to claim 6, wherein the component (C) is selected from polyisobutylene, hydrogenated polyisoprene, hydrogenated polybutadiene and copolymers thereof. The composition according to claim 1, wherein the hydrosilyl group-containing organic polymer (C) is a (meth)acrylate ester polymer. The composition according to claim 8, wherein the component (C) is a polymer which is prepared by polymerising at least one monomer selected from ethyl acrylate, butyl acrylate, allyl acrylate, methyl methacrylate, butyl methacrylate and allyl methacrylate, or prepared by polymerizing at least one monomer selected from the above acrylates and methacrylates and at least one copolymerizable monomer selected from styrene, vinyl acetate and acrylonitrile. The composition according to claim 1, wherein the hydrosilyl group of the organic polymer (C) is present at a molecular end. The composition according to claim 1, the organic polymer (D) has a molecular weight of from 500 to 50,000 and has at least one alkenyl group of the formula: wherein R¹ is a group selected from divalent groups of the formulas: -R²-, -R³-O-R⁴-, (wherein R², R³ and R⁴ are divalent hydrocarbon groups having 1 to 20 carbon atoms.), R⁵ is hydrogen or a methyl group, and a is 0 or 1. The composition according to claim 1, wherein the components (C) and (D) both are a polyester polymer. The composition according to claim 1, wherein the components (C) and (D) both are a hydrocarbon polymer. The composition according to claim 13, wherein the components (C) and (D) both are selected from the group consisting of polyisobutylene, hydrogenated polyisoprene, hydrogenated polybutadiene, 1,4-polybutadiene, 1,2-polybutadiene and copolymers thereof. The composition according to claim 1, wherein the components (C) and (D) both are a (meth)acrylate ester polymer.

Inventors: CHIBA MAKOTO - - SHIOYA-CHO, IWAHARA TAKAHISA - - KITAOCHIA, TAKAHARA TOMOKO - - AKIBADAI, YONEZAWA KAZUYA - - TSUTSUJIGA, CHIBA, MAKOTO 6-31-17, SHIOYA-CHO, IWAHARA, TAKAHISA 1-324-403, KITAOCHIAI 1-CHOME, TAKAHARA, TOMOKO 1-6-11, AKIBADAI, YONEZAWA, KAZUYA 5-12-11, TSUTSUJIGAOKA
Applicants: KANEGAFUCHI CHEMICAL IND, KANEGAFUCHI CHEMICAL INDUSTRY CO., LTD.
Application year: 1990
Main classification: C08L101
IPC codes: C08G64, C08G65, C08G77, C08L67, C08L101, C08F30, C08F20, C08L23, C08G63, C08L71, C08K5, C08L43, C08F8, C07F7, C08F10, C08L83, C08L33