Curable composition, adhesive, method of producing fiber-reinforced composite material, and fiber-reinforced composite material

A curable composition comprising:

• a polymerizable compound (A) which is one or more compounds selected from the group consisting of an epoxy compound (A1) and a vinyl ether compound (A2);
• a reactive compound (B) which is one or more compounds selected from the group consisting of a compound (B1) having one or more functional groups selected from a hydroxyl group and a carboxyl group and a polyvalent carboxylic anhydride (B2);
• a compound (C) represented by the following formula (C1);
• and
• a compound (D) represented by the following formula (D1),
• wherein the compound (B 1) having one or more functional groups selected from a hydroxyl group and a carboxyl group is a compound selected from the group consisting of a compound represented by the following formula (B1-1), a compound represented by the following formula (B1-2) and a compound represented by the following formula (B1-3);
• wherein the polyvalent carboxylic anhydride (B2) is a compound selected from the group consisting of tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, hexahydrotrimellitic anhydride, phthalic anhydride, trimellitic anhydride, and a styrene-maleic anhydride copolymer;
• wherein in the formula (C1), Rc1, Rc2, and Rc3 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonate group, a phosphino group, a phosphinyl group, a phosphonate group, or an organic group;
• Rc4 and Rc5 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfino group, a sulfo group, a sulfonate group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonate group, or an organic group;
• and Ar represents an aromatic group which may have a substituent;
• wherein in the formula (D1), Rd1 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or a phenyl group which may have a substituent;
• Rd2 represents a phenyl group which may have a substituent;
• Rd5 represents an alkyl group having 1 to 6 carbon atoms or an aryl group which may have a substituent;
• and p represents 0 or 1,
• wherein in the formula (B1-1), Rb1 represents a hydrogen atom or a methyl group;
• Rb2 represents a (d+e+f) valent aromatic group;
• d represents an integer of 1 to 3;
• e and f each represent an integer of 0 to 3;
• and (e+f) represents an integer of 1 or higher, and
• wherein in the formulae (B1-2) and (B1-3), Rb1 represents a hydrogen atom or a methyl group;
• Rb3 and Rb4 represent an alkylene group having 1 to 20 carbon atoms;
• L represents —O—, —CO—O—, or —O—CO—;
• in the formula (B1-2), g represents an integer of 1 to 5;
• and in the formula (B1-3), g represents an integer of 1 to 5.

A curable composition comprising:

• a polymerizable compound (A) which is one or more compounds selected from the group consisting of an epoxy compound (A1) and a vinyl ether compound (A2);
• a reactive compound (B) which is one or more compounds selected from the group consisting of a compound (B1) having one or more functional groups selected from a hydroxyl group and a carboxyl group and a polyvalent carboxylic anhydride (B2);
• a compound (C) represented by the following formula (C1);
• and
• a compound (D) represented by the following formula (D1),
• wherein the epoxy compound (A1) is a compound selected from the group consisting of 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-meth-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexyl-3′,4′-epoxy-6′-methylcyclohexanecarboxylate, ε-caprolactone-modified 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate, trimethylcaprolactone-modified 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate, β-methyl-δ-valerolactone-modified 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), di(3,4-epoxycyclohexylmethyl)ether of ethylene glycol, ethylenebis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxycyclohexahydro phthalate, di-2-ethylhexyl epoxycyclohexahydro phthalate, a compound represented by the following formula (A-1);
• 2-methylglycidyl(meth)acrylate, 3,4-epoxybutyl(meth)acrylate, 6,7-epoxyheptyl(meth)acrylate, 2-glycidyloxyethyl(meth)acrylate, 3-glycidyloxy-n-propyl(meth)acrylate, 4-glycidyloxy-n-butyl(meth)acrylate, 5-glycidyloxy-n-hexyl(meth)acrylate, 6-glycidyloxy-n-hexyl(meth)acrylate, a bisphenol A epoxy resin, a bisphenol F epoxy resin, a bisphenol S epoxy resin, a bisphenol AD epoxy resin, a naphthalene epoxy resin, a biphenyl epoxy resin, a phenol novolac epoxy resin, a brominated phenol novolac epoxy resin, an ortho-cresol novolac epoxy resin, a bisphenol A novolac epoxy resin, a bisphenol AD novolac epoxy resin, an epoxide of a dicyclopentadiene phenol resin, an epoxide of a naphthalene phenol resin, dimer acid glycidyl ester, tetraglycidylamino diphenyl methane, triglycidyl-p-aminophenol, tetraglycidyl metaxylylene diamine, tetraglycidyl bisaminomethyl cyclohexane, triglycidyl isocyanurate, phloroglucinol triglycidyl ether, trihydroxy biphenyl triglycidyl ether, trihydroxy phenyl methane triglycidyl ether, glycerin triglycidyl ether, 2-[4-(2,3-epoxypropoxy)phenyl]-2-[4-[1,1-bis[4-(2,3-epoxypropoxy)phenyl]ethyl]phenyl]propane, 1,3-bis[4-[1-[4-(2,3-epoxypropoxy)phenyl]-1-[4-[1-[4-(2,3-epoxypropoxy)phenyl]-1-methylethyl]phenyl]ethyl]phenoxy]-2-propanol, tetrahydroxy phenyl ethane tetraglycidyl ether, tetraglycidyl benzophenone, bisresorcinol tetraglycidyl ether, tetraglycidoxy biphenyl, a 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, and
• a polymer having an unsaturated aliphatic hydrocarbon group in a side chain thereof and an epoxy group formed by oxidation of an unsaturated bond contained in the side chain,
• wherein in the formula (A-1), Z represents a single bond, a divalent group selected from the group consisting of —O—, —O—CO—, —S—, —SO—, —SO2—, —CH2—, —C(CH3)2—, CBr2—, —C(CBr3)2—,—C(CF3)2—, and —Ra19—O—CO—;
• Ra19 represents an alkylene group having 1 to 8 carbon atoms;
• and Ra1 to Ra18 each independently represent a group selected from the group consisting of a hydrogen atom, a halogen atom, and an organic group,
• wherein in the formula (C1), Rc1, Rc2, and Rc3 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonate group, a phosphino group, a phosphinyl group, a phosphonate group, or an organic group;
• Rc4 and Rc5 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfino group, a sulfo group, a sulfonate group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonate group, or an organic group;
• and Ar represents an aromatic group which may have a substituent, and
• wherein in the formula (D1), Rd1 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or a phenyl group which may have a substituent;
• Rd2 represents a phenyl group which may have a substituent;
• Rd3 represents a hydrogen atom or a group represented by —CO—Rd5;
• Rd5 represents an alkyl group having 1 to 6 carbon atoms or an aryl group which may have a substituent;
• and p represents 0 or 1.