Curable resin composition comprising cyanate ester and polyisocyanate

Claim 2

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 homoprepolymer of one or more polyfunctional cyanate esters of (1), and (3) a coprepolyer of (1) and an amine; and (b) at least one compound selected from the group consisting of: (1) a polyisocyanate, (2) a homoprepolymer of one or more polyisocyanates, and (3) a coprepolymer of (1) and an acid anhydride, 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 3

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-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 4

The composition as defined in claim 1 wherein the polyisocyanate is selected from the group consisting of 2,2-bis-(p-isocyanatephenyl)propane; bis(p-isocyanatophenyl)methane; 4,4'-diisocyanatobiphenyl; 4,4'-diisocyanatodiphenyl sulfone; 4,4'-diisocyanatodiphenyl ether; 1,1-di(p-isocyanatophenyl) cyclohexane; methyl-bis(m-isocyanatophenyl)phosphineoxide; 1,5-diisocyanatonaphthalene; m-phenylenediisocyanate; tolylenediisocyanate; 3,3'-dimethyl-4,4'-diisocyanatobiphenyl; 3,3'-dimethoxy-4,4'-diisocyanatobiphenyl; m-xylylenediisocyanate; p-xylylenediisocyanate; bis(4-isocyanatohexyl)methane; hexamethylenediisocyanate; dodecamethylenediisocyanate; 2,11-diisocyanato dodecane; bis(p-phenyleneisocyanate-oxadiazole-1,3,4)p-phenylene; bis(p-phenyleneisocyanate)oxadiazole-1,3,4; bis(m-phenyleneisocyanate)oxadiazole-1,3,4; bis(4-p-phenyleneisocyanate-thiazol-2-yl)m-pheneylen; bis(m-phenyleneisocyanate) 4-phenyltriazole-1,2,4; (2-phenylene)benzimidazole-5,4'-diisocyanate; (2-phenylene)benzoxazole-5,4'-diisocyanate; (2-phenylene)benzothiazole-6,4'-diisocyanate; bis(2-phenyleneisocyanate-benzimidazole-6-yl)2,5-oxadiazole-1,3,4; bis(p-phenyleneisocyanate-2-benzimidazol-6-yl); bis(p-phenyleneisocyanate-2-benzoxazole-6-yl); tris(p-isocyanatophenyl)methane; namely 4,4',4"-triisocyanatotriphenyl methane; 2,4',4"-triisocyanatodiphenyl ether; 4,4',4"-triisocyanatotriphenyl phosphate; namely tri(p-isocyanatophenyl)phosphate; 2,4,6-triisocyanato-1-methylbenzene; 2,4,6-triisocyanato-1,3,5-trimethylbenzene; 1,3,7-triisocyanatonaphthalene; 2,4,4'-triisocyanatodiphenyl; 2,4,4'-triisocyanato-3-methyldiphenylmethane; 2,2',5,5'-tetraisocyanato-4,4'-dimethyldiphenylmethane; polyisocyanato polyphenylene polymethylene; and polyisocyanato polyoxyphenylene.

Claim 5

The composition as defined in claim 1 wherein the acid anhydride is represented by the formula ##STR5## wherein R 4 is organic group having 2 or more carbon atoms and valency of 4 or more and having no active hydrogen, and R 4 has such a structure that the two lactone 1-oxide rings have 4 to 6 members.

Claim 6

The composition as defined in claim 1 wherein the ratio by weight of component (a) to component (b) is in the range of from 99:1 to 1:99.

Claim 7

The composition as defined in claim 4 wherein amount of the acid anhydride employed is less than 0.5 mol per 1 mol of the combined amount of isocyanate group and cyanate group.

Claim 8

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 homoprepolymer of one or more polyfunctional cyanate esters of (1), and (3) a coprepolyer of (1) and an amine; (b) at least one compound selected from the group consisting of: (1) a polyisocyanate, (2) a homoprepolymer of one or more polyisocyanates, and (3) a coprepolymer of (1) and an acid anhydride, (c) at least one compound selected from the group consisting of: (1) a polyfunctional maleimide, (2) a homoprepolyer of one or more polyfunctional maleimides, 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 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 9

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 homoprepolymer of one or more polyfunctional cyanate esters of (1), and (3) a coprepolyer of (1) and an amine; (b) at least one compound selected from the group consisting of: (1) a polyisocyanate, (2) a homoprepolymer of one or more polyisocyanates, and (3) a coprepolymer of (1) and an acid anhydride, (c) at least one compound selected from the group consisting of: (1) a polyfunctional maleimide, (2) a homoprepolyer of one or more polyfunctional maleimides, 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 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 10

The composition as defined in claim 7 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)ehter; 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 11

The composition as defined in claim 7 wherein the polyisocyanate is selected from the group consisting of 2,2-bis(p-isocyanatophenyl)propane; bis(p-isocyanatophenyl)methane; 4,4'-diisocyanatobiphenyl; 4,4'-diisocyanatodiphenyl sulfone; 4,4'-diisocyanatodiphenyl ether; 1,1-di(p-isocyanatophenyl) cyclohexane; methyl-bis(m-isocyanatophenyl)phosphineoxide; 1,5-diisocyanatonaphthalene; m-phenylenediisocyanate; tolylenediisocyanate; 3,3'-dimethyl-4,4'-diisocyanatobiphenyl; 3,3'-dimethoxy-4,4'-diisocyanatobiphenyl; m-xylylenediisocyanate; p-xylylenediisocyanate; bis(4-isocyanatophexyl)methane; hexamethylenediisocyanate; dodecamethylenediisocyanate; 2,11-diisocyanato dodecane; bis(p-phenyleneisocyanate-oxadiazole-1,3,4)p-phenylene; bis(p-phenyleneisocyanate)oxadiazole-1,3,4; bis(m-phenyleneisocyanate) oxadiazole-1,3,4; bis(4-p-phenyleneisocyanate-thiazole-2-yl)m-phenylene; bis(m-phenyleneisocyanate) 4-phenyltriazole-1,2,4; (2-phenylene)benzimidazole-5,4'-diisocyanate; (2-phenylene)benzoxazole-5,4'-diisocyanate; (2-phenylene)benzothiazole-6,4'-diisocyanate; bis(2-phenyleneisocyanate-benzimidazol-6-yl)2,5-oxadiazole-1,3,4; bis(p-phenyleneisocyanate-2-benzimidazole-6-yl); bis(p-pehnyleneisocyanate-2-benzoxazol-6-yl); tris(p-isocyanatophenyl)methane; namely 4,4',4"-triisocyanatotriphenyl methane; 2,4',4"-triisocyanatodiphenyl ether; 4,4',4"-triisocyanatotriphenyl phosphate; namely tri(p-isocyanatophenyl)phosphate; 2,4,6-triisocyanato-1-methylbenzene; 2,4,6-triisocyanato-1,3,5-trimethylbenzene; 1,3,7-triisocyanatonaphthalene; 2,4,4'-triisocyanatodiphenyl; 2,4,4'-triisocyanato-3-methyldiphenylmethane; 2,2',5,5'-tetraisocyanato-4,4'-dimethyldiphenylmethane; polyisocyanato polyphenylene polymethylene; polyisocyanato polyoxyphenylene.

Claim 12

The composition as defined in claim 7 wherein the acid anhydride is represented by the formula ##STR6## wherein R 4 is organic group having 2 or more carbon atoms and valency of 4 or more and having no active hydrogen and R 4 has such a structure that the two lactone 1-oxide rings have 4 to 6 members.

Claim 13

The composition as defined in claim 10 wherein amount of the acid anhydride employed is less than 0.5 mol per 1 mol of the combined amount of isocyanate group and cyanate group.