Cyclic compound of carboxylic acid and its use

FIELD: chemistry.

SUBSTANCE: new cyclic carboxylic acid is obtained in reaction which includes performing connection [J] of, at least one terpen-based diene connection (conjugate diene connection), chosen from group consisting of alloocymen, ocymen, mircen, α-terpinen and α-phellandren, and [K], at least one unsaturated carboxylic acid, chosen from α,β-unsaturated carboxylic acids and monoethers of α, β-unsaturated dicarboxylic acids. Connecting agent (A) for antifouling paint is also revealed. It containes one or more substances chosen from new cyclic carboxylic acid, derivative from cyclic carboxylic acid (excluding metal salt), metal salts of cyclic carboxylic acid and metal salts of the derivative of cyclic carboxylic acid, as well as composition of antifouling paint, which contains connecting agent (A) and copolymer (B) for antifouling paint of self-cleaning type, which is a polymerising copolymer based on basic metal salt of unsaturated carboxylic acid or polymerising unsaturated copolymer based on silyl ether of unsaturated carboxylic acid. From composition of antifouling paint covering film can be formed, which has only slight influence on environment, it is evenly subjected to erosion with definite rate, is able to retain excellent properties against fouling for a long period of time and can be applied to the surfaces of ships and other objects, which are used in marine territories with high risk of fouling.

EFFECT: obtaining film of antifouling paint, which has only slight influence on environment, is evenly subjected to erosion with definite rate, is able to retain excellent properties against fouling for a long period of time.

26 cl, 12 dwg, 4 tbl

 

The text descriptions are given in facsimile form.

1. New cycloalkylcarbonyl acid represented by the formula [V]

where R1is a hydrogen atom, a group of 3-methyl-2-butenyl or group 2-methyl-1-propenyl,

m and n each is 0 or 1 (provided that m and n are not simultaneously equal to 0),

when R1is a hydrogen atom, R2-group 4-methyl-3-pentenyl, and R3and R4each is a hydrogen atom,

R5is an alkyl group with 1-10 carbon atoms, R6, R7and R8each is a hydrogen atom, when m=1, n=0,

when R1is a hydrogen atom, R2- group 4-methyl-3-pentenyl and R3and R4each is a hydrogen atom,

R6is an alkyl group with 1-10 carbon atoms, R5, R7and R8each is a hydrogen atom, when m=0, n=1,

when R1- group 3-methyl-2-butenyl, R2is a methyl group, and R3, R4and R6each is a hydrogen atom,

R5is an alkyl group with 1-10 carbon atoms, R7and R8each is a hydrogen atom, when m=1, n=0,

when R1- group 3-methyl-2-butenyl, R2is a methyl group, and R3, R4and R5each is a hydrogen atom,

R6is an alkyl group with 1-10 carbon atoms, R7and R8each is a hydrogen atom, when m=0, n=1,

when R1- group 2-methyl-1-propenyl, R2is a hydrogen atom and R3and R4each is a methyl group,

R5is an alkyl group with 1-10 carbon atoms, R6, R7and R8each is a hydrogen atom, when m=1, n=0,

when R1- group 2-methyl-1-propenyl, R is a hydrogen atom and R3and R4each is a methyl group,

R6is an alkyl group with 1-10 carbon atoms, R5, R7and R8each is a hydrogen atom, when m=0, n=1,

when R1- group 2-methyl-1-propenyl, R2is a hydrogen atom and R3and R4each is a methyl group,

R5, R6and R7each is a hydrogen atom,

R8is a methyl group, with m=1, n=1,

when R1group 2-methyl-1-propenyl, R2is a hydrogen atom and R3and R4each is a methyl group,

R5, R6and R8each is a hydrogen atom,

R7is a methyl group, with m=1, n=1.

2. Cycloalkylcarbonyl acid according to claim 1, and cycloalkylcarbonyl acid according to the formula [V] is represented by the formula [Va], [Vb], [Vc], [Vd], [Ve], [Vf], [Vg] or [Vh]

where Me is a methyl group.

3. The method of obtaining cycloalkylcarbonyl acid according to any one of claims 1 and 2, VK is uchumi carrying out the reactions of addition [J], at least one based on terpene diene compounds (conjugated diene compound)selected from the group consisting of alloocimene, ocimene, myrcene, α-terpinene and α-phellandrene, and [K]at least one unsaturated carboxylic acid selected from α,βunsaturated carboxylic acids and monoamino α, βunsaturated dicarboxylic acids.

4. Connecting agent for antifouling paints containing one or more substances represented by the formula

where Me is a methyl group,

selected from cyclic carboxylic acid obtained by the reaction of accession unsaturated carboxylic acid with a conjugate diene compound, a derivative of the cyclic carboxylic acid (excluding metal salt), a metal salt of a cyclic carboxylic acid and a metal salt derivative of the cyclic carboxylic acid.

5. Connecting agent for antifouling paint according to claim 4, in which the cyclic carboxylic acid, a derivative of the cyclic carboxylic acid (excluding metal salt), salt metal circular Carbo is a strong acid and a metal salt derivative of the cyclic carboxylic acid are cycloalkylcarbonyl acid according to any one of claims 1 to 2.

6. The composition of antifouling paints containing

(A) connecting agent for antifouling paint according to claim 4 and

(B) a copolymer for antifouling paints self-cleaning type that represents a polymerizable copolymer based on the primary metal salt of unsaturated carboxylic acid or a polymerizable unsaturated copolymer based on silyl ester of unsaturated carboxylic acid.

7. The composition according to claim 6, further containing (C) non-fouling agent.

8. The composition of claim 6, in which the agent (S) has (C1) copper or compound of copper.

9. The composition according to claim 6, in which the antifouling agent (C) contains (C2) organic agent against adhesion (excluding copper or compound of copper (C1)).

10. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type represents a polymerizable copolymer, based on the primary metal salt of unsaturated carboxylic acid.

11. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite unit derived from the polymerizable compound of the base metal unsaturated carboxylic acid represented by the formula [1]

where R1unsaturated containing the th link organic group

CH2- (CH3)-, CH2CH, noos-CH=CH - or noos-CH=C(CH3)-, -COOH

may form a metal salt or ester, and

M is a metal atom.

12. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite block received from the primary metal salt of (meth)acrylic acid.

13. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite unit derived from the basic salts of zinc or copper (meth)acrylic acid.

14. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type represents a polymerizable copolymer, based on the connection metal unsaturated carboxylic acid having the composition unit derived from the polymerizable compound of the metal unsaturated carboxylic acid containing no hydroxyl group associated with the metal atom.

15. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite unit derived from the polymerizable compound of the metal unsaturated carboxylic acid represented by the formula [II]

img src="https://img.russianpatents.com/868/8689315-s.jpg" height="5" width="76" >

where R1- containing unsaturated bond, an organic group

CH2=C(CH3)-, CH2=CH-, noos-CH-CH - or noos-CH=C(CH3)-, -COOH may form a metal salt or ester, M is a metal atom, L is a residue of an organic acid,- OCOR2(R2is an alkyl group, cycloalkyl group, an aromatic hydrocarbon group which may have a substituent, or kalkilya group), n is the number of valence of the metal M(-1)".

16. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having a compositional unit derived from the polymerizable compound of the metal unsaturated carboxylic acid containing no hydroxyl group associated with the metal atom.

17. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite unit derived from the salt of zinc or copper (meth)acrylic acid containing no hydroxyl group associated with the atom zinc or copper atom.

18. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type represents a polymerizable copolymer, based on the metal salt of unsaturated carboxylic acid obtained by the copolymerization of (a) monomer is Oli zinc or copper salt (meth)acrylic acid and (b) other monomer, copolymerizes with the monomer (a) and containing a composition unit derived from monomer (a) zinc salts or salts of copper (meth)acrylic acid in the amount of 50-98 wt.% (composite blocks (a) + composite blocks (b)=100 wt%).

19. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type represents a polymerizable copolymer, based on celilova the ester of unsaturated carboxylic acid.

20. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type is a copolymer having in a molecule composite unit derived from the unsaturated monomer salelologa of carboxylate, which is represented by the formula [IIIA]

where R1- containing unsaturated bond, an organic group SN2=C(CH3)-, CH2=CH-, noos-CH=CH - or noos-CH=C(CH3)-, -COOH may form a metal salt or ester, L1L2and L3may be the same or different, and each independently a hydrogen atom, alkyl group, cycloalkyl group, aromatic hydrocarbon group, aranceles group or alkylsilane group, and these groups may have a substituent.

21. The composition according to claim 6, in which the copolymer (B) for antifouling paints self-cleaning type represents the FDS is the first copolymer, obtained by copolymerization silyl(meth)acrylate and an unsaturated monomer, copolymerizes with silyl(meth)acrylate.

22. Covering the antifouling film formed from the composition of the antifouling paint according to any one of p-21.

23. Ship or submarine design, covered with a covering film formed from the composition of the antifouling paint according to any one of p-21.

24. Fishing accessory or a fishing net, covered with a covering film formed from the composition of the antifouling paint according to any one of p-21.

25. Method of preventing fouling of a ship or submarine design, including the production of the surface ship or submarine design by applying a covering film formed from the composition of the antifouling paint according to any one of p-21.

26. The method of protection against fouling fishing accessories or fishing nets, including the production of coatings applied on the surface of fishing accessories or fishing net covering film formed from the composition of the antifouling paint according to any one of p-21.



 

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