# US 2021/0079232 A1 · Antifouling paint composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0079232 A1 - Document ID: US20210079232A1 - Status: Published application - Kind: A1 - Application number: 17/104,696 - Filed: 2020-11-25 - Published: 2021-03-18 - Earliest claimed: 2018-06-01 - Assignees: Mitsubishi Chemical Corporation - Applicants: Mitsubishi Chemical Corporation - Inventors: Sho KATSUMATA; Kana TANIGUCHI; Junichi NAKAMURA - Web page: https://patentgrep.com/patent/US20210079232A1 ## CPC - C09D 5/1668: {Vinyl-type polymers} - C07C 67/04: by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds - C08F 8/14: Esterification - C08F 220/14: Methyl esters {, e.g. methyl (meth)acrylate} - C08F 220/1802: {C2-(meth)acrylate, e.g. ethyl (meth)acrylate} - C08F 220/1806: {C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate} - C09D 5/1618: {inorganic} - C09D 5/1625: {organic} - C09D 5/1687: {Use of special additives} - C09D 7/63: organic - C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen - C09D 143/04: Homopolymers or copolymers of monomers containing silicon - C09D 193/04: Rosin - C09F 1/04: Chemical modification, e.g. esterification (resin soaps C11D) - C08F 230/085: {the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes} - C08F 2800/20: as weight or mass percentages - C08F 2810/50: wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority - C08K 5/101: of monocarboxylic acids - C08K 5/103: with polyalcohols - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09F: NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract The invention provides an antifouling paint composition comprising at least one compound (A) selected from the group consisting of compounds represented by Formula (1), Formula (2), and Formula (3); and a vinyl-based copolymer (B). ## Claims ### Claim 1 An antifouling paint composition, comprising: at least one compound (A) selected from the group consisting of compounds represented by Formula (1), Formula (2), and Formula (3); and a vinyl-based copolymer (B), wherein in the formulae, Ra, Rb, and Rc each represent a hydrocarbon group having 1 to 40 carbon atoms; X represents —O—, —S—, or —NR14—, where R14 represents a hydrogen atom or an alkyl group; R1 and R2 each represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R3 and R5 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; and R4 and R6 each represents an alkylene group having 1 to 10 carbon atoms. ### Claim 2 (depends on 1) The antifouling paint composition according to claim 1, wherein Ra, Rb, or Rc of the compound (A) is a cyclic hydrocarbon residue derived from rosin. ### Claim 3 (depends on 1) The antifouling paint composition according to claim 1, wherein the vinyl-based copolymer (B) is a (meth)acrylic copolymer including at least one constituent unit selected from the group consisting of a constituent unit (u1) having at least one structure (I) represented by Formula (4), Formula (5), or Formula (6), a constituent unit (u2) containing a triorganosilyloxycarbonyl group, and a constituent unit (u3) having at least one structure (III) represented by Formula (7) or Formula (8), wherein in the formulae, X represents —O—, —S—, or —NR21—, where R21 represents a hydrogen atom or an alkyl group; R15 and R16 each represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R17 and R19 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; and R18 and R20 each represents an alkylene group having 1 to 10 carbon atoms, —COO-M-OCO (7) —COO-M-R13 (8) wherein in the formulae, M represents Zn, Cu, Mg, or Ca; and R13 represents an organic acid residue other than a (meth)acryloyloxy group. ### Claim 4 (depends on 1) The antifouling paint composition according to claim 1, further comprising at least one selected from the group consisting of a compound that reacts with an acid, a basic compound, an acidic compound, and a dehydrating agent. ### Claim 5 (depends on 4) The antifouling paint composition according to claim 4, wherein the compound that reacts with an acid is at least one compound (Y3) selected from the group consisting of compounds represented by Formula (31), Formula (32), and Formula (33), wherein in the formulae, X represents —O—, —S—, or —NR21—, where R21 represents a hydrogen atom or an alkyl group; R7 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms; R8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R9 and R11 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; R10 represents a single bond or an alkylene group having 1 to 9 carbon atoms; and R12 represents an alkylene group having 1 to 9 carbon atoms. ### Claim 6 (depends on 1) The antifouling paint composition according to claim 1, further comprising an antifouling agent. ### Claim 7 (depends on 6) The antifouling paint composition according to claim 6, wherein the antifouling paint composition contains, as the antifouling agent, at least one selected from the group consisting of cuprous oxide, pyridine triphenyl borane, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and medetomidine. ### Claim 8 (depends on 2) The antifouling paint composition according to claim 2, wherein the vinyl-based copolymer (B) is a (meth)acrylic copolymer including at least one constituent unit selected from the group consisting of a constituent unit (u1) having at least one structure (I) represented by Formula (4), Formula (5), or Formula (6), a constituent unit (u2) containing a triorganosilyloxycarbonyl group, and a constituent unit (u3) having at least one structure (III) represented by Formula (7) or Formula (8), wherein in the formulae, X represents —O—, —S—, or —NR21—, where R21 represents a hydrogen atom or an alkyl group; R15 and R16 each represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R17 and R19 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; and R18 and R20 each represents an alkylene group having 1 to 10 carbon atoms, —COO-M-OCO (7) —COO-M-R13 (8) wherein in the formulae, M represents Zn, Cu, Mg, or Ca; and R13 represents an organic acid residue other than a (meth)acryloyloxy group. ### Claim 9 (depends on 2) The antifouling paint composition according to claim 2, further comprising at least one selected from the group consisting of a compound that reacts with an acid, a basic compound, an acidic compound, and a dehydrating agent. ### Claim 10 (depends on 9) The antifouling paint composition according to claim 9, wherein the compound that reacts with an acid is at least one compound (Y3) selected from the group consisting of compounds represented by Formula (31), Formula (32), and Formula (33), wherein in the formulae, X represents —O—, —S—, or —NR21—, where R21 represents a hydrogen atom or an alkyl group; R7 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms; R8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R9 and R11 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; R10 represents a single bond or an alkylene group having 1 to 9 carbon atoms; and R12 represents an alkylene group having 1 to 9 carbon atoms. ### Claim 11 (depends on 2) The antifouling paint composition according to claim 2, further comprising an antifouling agent. ### Claim 12 (depends on 11) The antifouling paint composition according to claim 11, wherein the antifouling paint composition contains, as the antifouling agent, at least one selected from the group consisting of cuprous oxide, pyridine triphenyl borane, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and medetomidine. ### Claim 13 (depends on 3) The antifouling paint composition according to claim 3, further comprising at least one selected from the group consisting of a compound that reacts with an acid, a basic compound, an acidic compound, and a dehydrating agent. ### Claim 14 (depends on 13) The antifouling paint composition according to claim 13, wherein the compound that reacts with an acid is at least one compound (Y3) selected from the group consisting of compounds represented by Formula (31), Formula (32), and Formula (33), wherein in the formulae, X represents —O—, —S—, or —NR21—, where R21 represents a hydrogen atom or an alkyl group; R7 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms; R8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; R9 and R11 each represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group; R10 represents a single bond or an alkylene group having 1 to 9 carbon atoms; and R12 represents an alkylene group having 1 to 9 carbon atoms. ### Claim 15 (depends on 3) The antifouling paint composition according to claim 3, further comprising an antifouling agent. ### Claim 16 (depends on 15) The antifouling paint composition according to claim 15, wherein the antifouling paint composition contains, as the antifouling agent, at least one selected from the group consisting of cuprous oxide, pyridine triphenyl borane, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and medetomidine. ### Claim 17 (depends on 4) The antifouling paint composition according to claim 4, further comprising an antifouling agent. ### Claim 18 (depends on 17) The antifouling paint composition according to claim 17, wherein the antifouling paint composition contains, as the antifouling agent, at least one selected from the group consisting of cuprous oxide, pyridine triphenyl borane, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and medetomidine. ### Claim 19 (depends on 5) The antifouling paint composition according to claim 5, further comprising an antifouling agent. ### Claim 20 (depends on 19) The antifouling paint composition according to claim 19, wherein the antifouling paint composition contains, as the antifouling agent, at least one selected from the group consisting of cuprous oxide, pyridine triphenyl borane, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and medetomidine.