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

Patent metadata

Field	Value
Publication number	US-9683150-B2
Application number	US-201514636428-A
Country	US
Kind code	B2
Filing date	Mar 3, 2015
Priority date	Mar 7, 2014
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

A curable composition obtained by blending a polymerizable compound (A) having predetermined types of polymerizable functional groups, a reactive compound (B) having predetermined types of reactive functional groups, a compound (C) which is an imidazolyl group-containing compound having a predetermined structure, and a compound (D) which is an oxime compound or an oxime ester compound having a predetermined structure.

First claim

What is claimed is:

1. 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 (B 1) 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 in the formula (C1), R c1 , R c2 , and R c3 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; R c4 and R c5 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), R d1 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent or an aryl group which may have a substituent; R d2 represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aryl group which may have a substituent; R d3 represents a hydrogen atom or a group represented by —CO—R d5 ; R d5 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.

2. The curable composition according to claim 1 ,
wherein the reactive compound (B) contains the compound (B 1) having one or more functional groups selected from a hydroxyl group and a carboxyl group, and
the compound (B1) having one or more functional groups selected from a hydroxyl group and a carboxyl group further contains a (meth)acryloyl group.

3. The curable composition according to claim 2 , wherein the epoxy compound (A) is an aliphatic epoxy compound.

4. The curable composition according to claim 1 , wherein the epoxy compound (A) is an aliphatic epoxy compound.

5. An adhesive which is formed from the curable composition according to claim 1 .

6. A method of producing a fiber-reinforced composite material, comprising curing the curable composition according to claim 1 , which is impregnated into reinforced fibers, by heating.

7. A fiber-reinforced composite material comprising:
a matrix formed of a cured material of the curable composition according to claim 1 ; and reinforced fibers.

8. 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), R c1 , R c2 , and R c3 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; R c4 and R c5 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), R d1 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; R d2 represents a phenyl group which may have a substituent; R d5 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), R b1 represents a hydrogen atom or a methyl group; R b2 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), R b1 represents a hydrogen atom or a methyl group; R b3 and R b4 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.

9. The curable composition according to claim 8 , wherein the epoxy compound (A) is an aliphatic epoxy compound.

10. An adhesive which is formed of the curable composition according to claim 8 .

11. A method of producing a fiber-reinforced composite material, comprising curing the curable composition according to claim 8 , which is impregnated into reinforced fibers, by heating.

12. A fiber-reinforced composite material comprising a matrix formed of a cured material of the curable composition according to claim 8 ; and reinforced fibers.

13. 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-epoxy

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Tadokoro Yoshinori
• Chisaka Hiroki
• Noda Kunihiro
• Shiota Dai

Classifications

• C08G59/42

  Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof · CPC title

• C08K7/02

  Fibres or whiskers · CPC title

• C08G59/5073

  having two nitrogen atoms in the ring · CPC title

• C08G59/62

  Alcohols or phenols · CPC title

• C09J163/04

  Epoxynovolacs · CPC title