# US 4,393,195 A · Curable cyanate ester/acrylic epoxy ester composition

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- Number: US 4,393,195 A
- Document ID: US4393195A
- Status: Granted
- Kind: A
- Application number: 06/175,510
- Filed: 1980-08-05
- Granted: 1983-07-12
- Earliest claimed: 1979-08-08
- Assignees: Mitsubishi Gas Chemical Company, Inc.
- Inventors: Morio Gaku; Nobuyuki Ikeguchi; Satoshi Ayano
- Web page: https://patentgrep.com/patent/US4393195A

## CPC

- C08G 73/12: Unsaturated polyimide precursors
- C08F 220/325: {containing glycidyl radical, e.g. glycidyl (meth)acrylate}
- C08G 59/4014: {Nitrogen containing compounds}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) polyfunctional cyanate ester, prepolymer of the cyanate ester, or coprepolymer of the cyanate ester and an amine, and (b) acrylic epoxy esters, methacrylic epoxy esters, prepolymers of acrylic epoxy esters, prepolymers methacrylic epoxy esters, coprepolymers of acrylic epoxy esters and methacrylic epoxy esters and mixtures thereof, and a curable resin composition comprising a mixture or a preliminary reaction product of above component (a), above component (b) and (c) a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine are disclosed. Cured resin having excellent impact-resistance, adhesive power, heat-resistance and chemical resistance can be prepared from the compositions.

## Claims

### Claim 1

A curable resin composition consisting essentially of
(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 polyfunction aromatic cyanate ester monomers of (1), and
(3) a coprepolymer of (1) and an amine; and
(b) at least one compound, said compound being selected from the group consisting of acrylic epoxy esters and methacrylic epoxy esters represented by the formula: ##STR7## wherein X.sup.1 is hydrogen or methyl, each of X.sup.2 and X.sup.3 is hydrogen, methyl or ethyl, or when together X.sup.2 and X.sup.3 represent alkylene having 3-5 carbon atoms, R is hydrocarbon or substituted hydrocarbon having 1-16 carbon atoms, homoprepolymers of one or more acrylic epoxy esters, homoprepolymers of one or more methacrylic epoxy esters, coprepolymers of acrylic epoxy esters and methacrylic epoxy esters 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-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 3 (depends on 1)

The composition as defined in claim 1 wherein R group in the compound represented by the above formula I is --CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH(CH.sub.3)--, --(CH.sub.2).sub.4 --CH(CH.sub.2)--, --(CH.sub.2).sub.6 --CH(CH.sub.3)--, --(CH.sub.2).sub.10 --CH(CH.sub.3)--, ##STR8## or --(CHY.sup.1 CHY.sup.2 O).sub.p -- wherein both of Y.sup.1 and Y.sup.2 are hydrogen, or one of Y.sup.1 or Y.sup.2 is hydrogen and the other is methyl, and p is integer of 1-7.

### Claim 4 (depends on 1)

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 5

A curable resin composition consisting essentially of:
(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 polyfunction aromatic cyanate ester monomers of (1), and
(3) a coprepolymer of (1) and an amine;
(b) at least one compound, said compound being selected from the group consisting of acrylic epoxy esters and methacrylic epoxy esters represented by the formula: ##STR9## wherein X.sup.1 is hydrogen or methyl, each of X.sup.2 and X.sup.3 is hydrogen, methyl or ethyl, or when together X.sup.2 and X.sup.3 represent alkylene having 3-5 carbon atoms, R is hydrocarbon or substituted hydrocarbon having 1-16 carbon atoms, homoprepolymers of one or more acrylic epoxy esters, homoprepolymers of one or more methacrylic epoxy esters, coprepolymers of acrylic epoxy esters and methacrylic epoxy esters and mixtures thereof; and
(c) at least one compound selected from the group consisting of:
(1) a polyfunctional maleimide,
(2) a homoprepolymer of one or more polyfunctional maleimides 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 (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 esters 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 R group in the compound represented by the above formula I is --CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH(CH.sub.3)--, --(CH.sub.2).sub.4 --CH(CH.sub.2)--, --(CH.sub.2).sub.6 --CH(CH.sub.3)--, --(CH.sub.2).sub.10 --CH(CH.sub.3)--, ##STR10## or --(CHY.sup.1 CHY.sup.2 O).sub.p -- wherein both of Y.sup.1 and Y.sup.2 are hydrogen, or one of Y.sup.1 or Y.sup.2 is hydrogen and the other is methyl, and p is integer of 1-7.

### Claim 8 (depends on 5)

The composition as defined in claim 5 wherein the ratio by weight of component (a) and component (b) is in the range of from 99:1 to 1:99.