US 7,557,148 B2 · Cyclic carboxylic acid compound and use thereof

Abstract

A novel cyclic carboxylic acid formed by the addition reaction of an unsaturated carboxylic acid with a conjugated diene compound and a metal salt thereof are disclosed. A compounding agent (A) for an antifouling paint comprising one or more substances selected from the novel cyclic carboxylic acid, a derivative of the cyclic carboxylic acid (except a metal salt), a metal salt of the cyclic carboxylic acid and a metal salt of a derivative of the cyclic carboxylic acid, and an antifouling paint composition comprising the compounding agent (A) and a copolymer (B) for a self-polishing type antifouling paint are also disclosed. The antifouling paint composition can form an antifouling coating film which is a small burden to the environment, is uniformly eroded at a given rate, is capable of maintaining excellent antifouling performance for a long period of time and is applicable to ships or the like used in the highly fouling sea area.

Claims50

Dependent claims

A novel cycloalkenylcarboxylic acid represented by the following formula [V] or a salt thereof:

wherein R1 is a 3-methyl-2-butenyl group or a 2-methyl-1-propenyl group,
when R1 is a 3-methyl-2-butenyl group, R2 is a methyl group and R3 and R4 are each a hydrogen atom,
when R1 is a 2-methyl-1-propenyl group, R2 is a hydrogen atom and R3 and R4 are each a methyl group,
R5 and R6 are each a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
m and n are each a number of 0 or 1 (with the proviso that it does not occur that m and n are 0 at the same time),
R7 and R8 are each a hydrogen atom or a hydrocarbon group,
when m is 0, R7 is a hydrogen atom,
when m is 1, R7 is a hydrogen atom or a hydrocarbon group,
when n is 0, R8 is a hydrogen atom,
when n is 1, R8 is a hydrogen atom or a hydrocarbon group, with the proviso that R7 and R8 are not both hydrocarbon groups,
when R1 is a 2-methyl-1-propenyl group, R2 is a hydrogen atom, R3 and R4 are each a methyl group and m=1, n=0, R5 is an alkyl group of 1 to 10 carbon atoms, R6, R7 and R8 are each a hydrogen atom, and
when R1 is a 2-methyl-1-propenyl group, R2 is a hydrogen atom, R3 and R4 are each a methyl group and m=0, n=1, R6 is an alkyl group of 1 to 10 carbon atoms, R5, R7 and R8 are each a hydrogen atom.

9 more elements

An antifouling paint composition comprising:

(A) a compounding agent for an antifouling paint comprising one or more substances selected from the group consisting of a cyclic carboxylic acid formed by the addition reaction of an unsaturated carboxylic acid with a conjugated diene compound, a derivative of the cyclic carboxylic acid (except a metal salt), the metal salt of the cyclic carboxylic acid, and the metal salt of a derivative of the cyclic carboxylic acid, wherein the cyclic carboxylic acid is a novel cycloalkenylcarboxylic acid represented by the following formula [V] or a novel bicycloalkenylcarboxylic acid represented by the following formula [VI] or a salt thereof:
wherein R1 is a hydrogen atom, a 3-methyl-2-butenyl group or a 2-methyl-1-propenyl group,
when R1 is a hydrogen atom, R2 is a 4-methyl-3-pentenyl group and R3 and R4 are each a hydrogen atom,
when R1 is a 3-methyl-2-butenyl group, R2 is a methyl group and R3 and R4 are each a hydrogen atom,
when R1 is a 2-methyl-1-propenyl group, R2 is a hydrogen atom and R3 and R4 are each a methyl group,
R5 and R6 are each a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
m and n are each a number of 0 or 1 (with the proviso that it does not occur that m and n are 0 at the same time),
R7 and R8 are each a hydrogen atom or a hydrocarbon group,
when m is 0, R7 is a hydrogen atom,
when m is 1, R7 is a hydrogen atom or a hydrocarbon group,
when n is 0, R8 is a hydrogen atom, and
when n is 1, R8 is a hydrogen atom or a hydrocarbon group, with the proviso that R7 and R8 are not both hydrocarbon groups;
wherein any one of R11 and R16 is an isopropyl group,
[A] in the case where R11 is an isopropyl group,
R12 and R13 are each a hydrogen atom,
R14 is a methyl group,
R15 and R16 are each a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
m and n are each a number of 0 or 1 (with the proviso that it does not occur that m and n are 0 at the same time),
R17 and R18 are each a hydrogen atom or a hydrocarbon group,
k and l are each 0,
R19 and R20 are each a hydrogen atom,
R21 and R22 are each a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
when m is 0, R17 is a hydrogen atom,
when m is 1, R17 is a hydrogen atom or a hydrocarbon group,
when n is 0, R18 is a hydrogen atom, and
when n is 1, R18 is a hydrogen atom or a hydrocarbon group, with the proviso that R17 and R18 are not both hydrocarbon groups, and
[B] in the case where R16 is an isopropyl group,
R11 and R12 are each a hydrogen atom,
R13 is a methyl group,
R14 is a hydrogen atom,
R15 is a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
m and n are each 0,
R17 and R18 are each a hydrogen atom,
k and l are each a number of 0 or 1 (with the proviso that it does not occur that k and l are 0 at the same time),
R19 and R20 are each a hydrogen atom or a hydrocarbon group,
R21 and R22 are each a hydrogen atom or an alkyl group of 1 to 10 carbon atoms,
when k is 0, R19 is a hydrogen atom,
when k is 1, R19 is a hydrogen atom or a hydrocarbon group,
when l is 0, R20 is a hydrogen atom, and
when l is 1, R20 is a hydrogen atom or a hydrocarbon group, with the proviso that R19 and R20 are not both hydrocarbon groups, and
(B) a copolymer for a self-polishing antifouling paint.

38 more elements

Dependencies are inferred from the claim text.

Cyclic carboxylic acid compound and use thereof

Life of this patent

Cyclic carboxylic acid compound and use thereof

Life of this patent

Abstract

Claims50