# US 4,396,745 A · Curable resin composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,396,745 A - Document ID: US4396745A - Status: Granted - Kind: A - Application number: 06/260,983 - Filed: 1981-05-06 - Granted: 1983-08-02 - Earliest claimed: 1980-05-08 - Assignees: Mitsubishi Gas Chemical Company, Inc. - Inventors: Nobuyuki Ikeguchi - Web page: https://patentgrep.com/patent/US4396745A ## CPC - C08K 5/315: Compounds containing carbon-to-nitrogen triple bonds - C08L 21/00: Compositions of unspecified rubbers - C08L 79/00: Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00 - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of the cyanate esters, coprepolymers of the cyanate esters and an amine and mixtures thereof, (b) at least one rubber, which is liquid at room temperature or elastic, selected from the group consisting of styrene butadiene rubber, isoprene rubber, polychloroprene rubber, butyl rubber, acrylic rubber, natural rubbers, a preliminary reaction product of an epoxy compound and isoprene rubber, a preliminary reaction product of a natural rubber and an epoxy compound, rubbers obtained by introducing acryloyl or methacryloyl group into isoprene, and acid anhydride moiety-containing rubbers obtained by adding double bond of an unsaturated acid anhydride to isoprene and mixtures thereof and optionally (c) at least one compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides or coprepolymers of the maleimides and an amine is disclosed. ## Claims ### Claim 1 A curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of: (1) a polyfunctional aromatic cyanate ester monomer having the formula: R--O--C.tbd.N).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a prepolymer of (1), and (3) a coprepolymer of (1) and an amine; and (b) at least one rubber, which is liquid at room temperature or elastic, selected from the group consisting of styrene butadiene rubber, isoprene rubber, polychloroprene rubber, butyl rubber, acrylic rubber, natural rubbers, preliminary reaction products of an epoxy compound and isoprene rubber, preliminary reaction products of a natural rubber and an epoxy compound, rubbers obtained by introducing an acryloyl or a methacryloyl group into isoprene, and acid anhydride moiety-containing rubber obtained by adding a double bond of an unsaturated acid anhydride to isoprene and mixtures thereof; said composition including a mixture of components (a) and (b), a preliminary reaction product of components (a) and (b), or the combination of said mixture and said preliminary reaction product. ### Claim 2 (depends on 1) The composition as defined in claim 1 wherein the cyanate ester is selected from the group consisting of 1,3- , 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatophenyl)methane; 2,2-bis(4-cyanatophenyl)propane; 2,2-bis(3,5-dichloro-4-cyanophenyl)propane; 2,2-bis(3,5-dibromo-4-dicyanatophenyl)propane; bis(4-cyanatophenyl) ether; bis(4-cyanatophenyl)thioether; bis(4-cyanatophenyl)sulfone; tris(4-cyanatophenyl)phosphite; tris(4-cyanatophenyl)phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak produced by reacting a novolak with cyanogen halide; cyanated bisphenol polycarbonate oligomer produced by reacting a bisphenol polycarbonate oligomer with cyanogen halide; and mixtures thereof. ### Claim 3 (depends on 1) The composition as defined in claim 1 wherein component (b) is acrylic rubber. ### Claim 4 (depends on 1) The composition as defined in claim 1 wherein component (b) is used in an amount of 1-95% by weight on the basis of total weight of components (a) and (b). ### Claim 5 A curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of: (1) a polyfunctional aromatic cyanate ester monomer having the formula: R--O--C.tbd.N).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a prepolymer of (1), and (3) a coprepolymer of (1) and an amine; (b) at least one rubber, which is liquid at room temperature or elastic, selected from the group consisting of styrene butadiene rubber, isoprene rubber, polychloroprene rubber, butyl rubber, acrylic rubber, natural rubbers, preliminary reaction products of an epoxy compound and isoprene rubber, preliminary reaction products of a natural rubber and an epoxy compound, rubbers obtained by introducing an acryloyl or a methacryloyl group into isoprene, and acid anhydride moiety-containing rubber obtained by adding a double bond of an unsaturated acid anhydride to isoprene and mixtures thereof, (c) at least one compound selected from the group consisting of: (1) a polyfunctional maleimide, (2) a prepolymer of (1), and (3) a coprepolymer of (1) and an amine, said composition including a mixture of components (a), (b) and (c), a preliminary reaction product of components (a), (b) and (c), the combination of said mixture and said preliminary reaction product, the combination of (a) and the preliminary reaction product of (b) and (c), the combination of (b) and the preliminary reaction product of (a) and (c), or the combination of (c) and the preliminary reaction product of (a) and (b). ### Claim 6 (depends on 5) The composition as defined in claim 5 wherein the cyanate ester is selected from the group consisting of 1,3-, 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatophenyl)methane; 2,2-bis(4-cyanatophenyl)propane; 2,2-bis(3,5-dichloro-4-cyanatophenyl)propane; 2,2-bis(3,5-dibromo-4-dicyanatophenyl)propane; bis(4-cyanatophenyl) ether; bis(4-cyanatophenyl)thioether; bis(4-cyanatophenyl) sulfone; tris(4-cyanatophenyl)phosphite; tris(4-cyanatophenyl) phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak produced by reacting a novolak with cyanogen halide; cyanated bisphenol polycarbonate oligomer produced by reacting a bisphenol polycarbonate oligomer with cyanogen halide; and mixtures thereof. ### Claim 7 (depends on 5) The composition as defined in claim 5 wherein component (b) is acrylic rubber. ### Claim 8 (depends on 5) The composition as defined in claim 5 wherein the polyfunctional maleimide is selected from the group consisting of 1,3- or 1,4-dimaleimide benzene, 1,3- or 1,4-bis(maleimide methylene)benzene, 1,3- or 1,4-dimaleimide cyclohexane, 1,3- or 1,4-bis(maleimide methylene)cyclohexane, 4,4'-dimaleimide biphenyl, bis(4-maleimidephenyl)methane, bis(4-maleimidephenyl) ether, bis(4-maleimidephenyl)sulfone, bis(4-maleimide-3-methylphenyl)methane, bis(4-maleimide-3-chlorophenyl)methane, bis(4-maleimide-3,5-dimethylphenyl)methane, 2,2-bis(4-maleimide-3-methylphenyl)propane, 2,2-bis(4-maleimide-3,5-dibromophenyl)propane, bis(4-maleimidephenyl)phenylmethane, 3,4-dimaleimidephenyl-4'-maleimidephenylmethane, 1,1-bis(4-maleimidephenyl)-1-phenylmethane, and maleimide derived from melamine and, addition product of formalin and an aniline in which benzene rings of two or more aniline bond through methylene group. ### Claim 9 (depends on 5) The composition as defined in claim 5 wherein component (b) is used in an amount of 1-95% by weight on the basis of total weight of components (a), (b) and (c).