Resin composition, cured product, sealing material, adhesive, insulating material, coating material, prepreg, multilayered body, and fiber-reinforced composite material
Provided is a resin composition comprises a cyanate ester compound (A), an amine adduct compound (B) and a borate ester (C).
1 . A resin composition comprising a cyanate ester compound (A), an amine adduct compound (B), and a borate ester (C), the resin composition having a mass ratio between the amine adduct compound (B) and the borate ester (C) ((B)/(C)) of 0.5 or more and 10.0 or less,
wherein the borate ester (C) includes the following compound
wherein each R independently represents a hydrocarbon group having 1 to 20 carbon atoms, which optionally has a substituent, and one or two or more oxygen atoms may be included in the hydrocarbon group,
wherein the substituent is a hydroxy group, an amino group or a carboxy group.
2 . The resin composition according to claim 1 , wherein the cyanate ester compound (A) comprises at least one selected from the group consisting of a compound represented by the following formula (I) and a compound represented by the following formula (II):
wherein each of Ar 1 independently represents an aromatic ring, each of Ra independently represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms and an alkoxy group having 1 to 4 carbon atoms, the alkyl group or the aryl group in Ra optionally has a substituent, a represents the number of cyanate groups bonded to Ar 1 , being each independently an integer of 1 to 3, b represents the number of Ra bonded to Ar 1 , being each independently a number obtained by subtracting (a+2) from the number of substitutable substituents of Ar 1 , c is an integer of 1 to 50, each of X independently represents any one of a single bond, a divalent organic group having 1 to 50 carbon atoms, a sulfonyl group (—SO 2 —), a divalent sulfur atom (—S—), and a divalent oxygen atom (—O—):
wherein Ar 2 represents an aromatic ring, each of Rb independently represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms, the alkyl group or aryl group in Rb optionally has a substituent, d represents the number of cyanate groups bonded to Ar 2 , being an integer of 2 to 3, and e represents the number of Rb bonded to Ar 2 , being a number obtained by subtracting (d+2) from the number of substitutable substituents of Ar 2 .
3 . The resin composition according to claim 2 , wherein each of X independently represents a divalent linking group selected from the group consisting of the following formulas (III) to (XIV):
wherein each of Ar 3 independently represents an aromatic ring, each of Rc, Rd, Rg and Rh independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, the alkyl group or the aryl group in Rc, Rd, Rg and Rh optionally has a substituent, each of Re and Rf independently represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms and an alkoxy group having 1 to 4 carbon atoms, the alkyl group or the aryl group in Re and Rf optionally has a substituent, and f represents an integer of 0 to 5;
wherein each of Ar 4 independently represents an aromatic ring, each of Ri and Rj independently represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms, the alkyl group or aryl group in Ri and Rj optionally has a substituent, and g represents an integer of 0 to 5;
wherein h represents an integer of 4 to 7, and each of Rk independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
4 . The resin composition according to claim 1 , wherein the cyanate ester compound (A) comprises at least one or more selected from the group consisting of a compound represented by the following formula (XV) and a compound represented by the following formula (XVI):
wherein each of Ar 5 independently represents an aromatic ring, each of RI independently represents a methylene group, a methyleneoxy group, a methylene oxymethylene group, an oxymethylene group, or a group in which these two or more are bonded to each other, each of Rm and Rn independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, the alkyl group or the aryl group in Rm and Rn optionally has a substituent, i represents the number of cyanate groups bonded to Ar 5 , being an integer of 1 to 3, j represents the number of Rm bonded to Ar 5 , being a number obtained by subtracting (i+2) from the number of substitutable substituents of Ar 5 , k represents the number of Rn bonded to Ar 5 , being a number obtained by subtracting 2 from the number of substitutable substituents of Ar 5 , 1 represents an integer of 1 or more, m represents an integer of 1 or more, and the arrangement of the repeating units is optional;
wherein each of Ar 6 independently represents an aromatic ring, each of Ro independently represents a methylene group, a methyleneoxy group, a methylene oxymethylene group, an oxymethylene group, or a group in which these are bonded to each other, each of Rp and Rq independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, the alkyl group or the aryl group in Rp and Rq optionally has a substituent, n represents the number of cyanate groups bonded to Ar 6 , being an integer of 2 to 3, o represents the number of Rp bonded to Ar 6 , being a number obtained by subtracting (n+2) from the number of substitutable substituents of Ar 6 , p represents the number of Rq bonded to Ar 6 , being a number obtained by subtracting 2 from the number of substitutable substituents of Ar 6 , and q represents an integer of 1 or more.
5 . The resin composition according to claim 1 , wherein the content of the amine adduct compound (B) is 0.01 to 30 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
6 . The resin composition according to claim 1 , wherein the content of the borate ester (C) is 0.01 to 15 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
7 . The resin composition according to claim 1 , further comprising a phenolic compound (D).
8 . The resin composition according to claim 7 , wherein the content of the phenolic compound (D) is 1 to 20 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
9 . The resin composition according to claim 1 , further comprising a toughening agent (E).
10 . The resin composition according to claim 9 , wherein the toughening agent (E) comprises a thermoplastic resin.
11 . The resin composition according to claim 9 , wherein the toughening agent (E) comprises a resin in powder form.
12 . The resin composition according to claim 9 , wherein the content of the toughening agent (E) is 1 to 40 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
13 . The resin composition according to claim 1 , wherein the content of the amine adduct compound (B) is 0.01 to 30 parts by mass relative to 100 parts by mass of the cyanate ester compound (A), wherein the content of the borate ester (C) is 0.01 to 15 parts by mass relative to 100 parts by mass of the cyanate ester compound (A), wherein the resin composition further comprises a phenolic compound (D), wherein the content of the phenolic compound (D) is 1 to 20 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
14 . The resin composition according to claim 13 , further comprising a toughening agent (E), wherein the content of the toughening agent (E) is 1 to 40 parts by mass relative to 100 parts by mass of the cyanate ester compound (A).
15 . A cured product of the resin composition according to claim 1 .
16 . A sealing material comprising the resin composition according to claim 1 .
17 . An adhesive comprising the resin composition according to claim 1 .
18 . An insulating material comprising the resin composition according to claim 1 .
19 . A coating material comprising the resin composition according to claim 1 .
20 . A prepreg formed from a base material and the resin composition according to claim 1 .
21 . A multilayered body formed from the prepreg according to claim 20 .
22 . A fiber-reinforced composite material comprising a reinforcement fiber and a cured product of the resin composition according to claim 1 .
23 . The rein composition according to claim 1 , wherein the mass ration between the amine adduct compound (B) and the borate ester (C) ((B)/(C)) is 0.5 or more and 5.0 or less.
24 . The resin composition according to claim 7 wherein the phenolic compound (D) is nonyl phenol and/or dinonyl phenol.