# US 8,541,493 B2 · Synthesis of zinc acrylate copolymer from acid functional copolymer, zinc pyrithione, and copper compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,493 B2 - Document ID: US8541493B2 - Status: Granted - Kind: B2 - Application number: 12/660,053 - Filed: 2010-02-19 - Published: 2011-08-25 - Granted: 2013-09-24 - Earliest claimed: 2010-02-19 - Assignees: Arch Chemicals, Inc. - Applicants: Paul S. Kappock; Kazunobu Takahashi - Inventors: Paul S. Kappock; Kazunobu Takahashi - Web page: https://patentgrep.com/patent/US8541493B2 ## CPC - C09D 5/1637: {Macromolecular compounds} - C09D 5/1625: {organic} - C09D 7/69: {Particle size larger than 1000 nm} - C09D 133/02: Homopolymers or copolymers of acids; Metal or ammonium salts thereof - C08K 5/0091: {Complexes with metal-heteroatom-bonds} - C08K 5/46: with oxygen or nitrogen in the ring - C08L 33/02: Homopolymers or copolymers of acids; Metal or ammonium salts thereof - 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Disclosed is a composition containing zinc ester functional polymer and particulate copper pyrithione, wherein the particles have an average aspect ratio within a range of from about 8 to about 15, where the zinc ester functional polymer and the copper pyrithione are obtained by reacting an acid functional polymer with zinc pyrithione and a copper salt or a copper carboxylate. Also disclosed is an antifouling coating containing such a composition. ## Claims ### Claim 1 A process for producing a composition containing a zinc ester functional polymer and particles of copper pyrithione where the particles have an average aspect ratio of from about 8 to about 15 comprising the steps of: reacting an acid functional polymer with zinc pyrithione in a solvent to form a solution comprising the zinc ester functional polymer; adding a copper compound to the solution comprising zinc ester functional polymer, wherein the copper compound is selected from copper salts, copper carboxylates, copper hydroxide, elemental copper, and combinations thereof; and mixing the solution comprising the copper compound and the zinc ester function polymer to form the particles of copper pyrithione. ### Claim 2 (depends on 1) The process of claim 1 wherein said acid functional polymer is an acid functional acrylate copolymer. ### Claim 3 (depends on 1) The process of claim 1 wherein said copper salt is selected from the group consisting of copper carbonate, copper nitrate, copper sulfate, copper chloride, copper sulfide and combinations thereof. ### Claim 4 (depends on 1) The process of claim 1 wherein said copper compound is copper hydroxide. ### Claim 5 (depends on 3) The process of claim 3 wherein said copper salt is used in combination with an organic acid selected from the group consisting of acetic acid, chloroacetic acid, propionic acid, octylic acid, versatic acid, ethylhexanoic acid, benzoic acid, naphthenic acid, palmetic acid, stearic acid, oleic acid, fatty acids, rosin acids, and combinations thereof. ### Claim 6 (depends on 4) The process of claim 4 wherein said copper compound is used in combination with an organic acid selected from the group consisting of acetic acid, chloroacetic acid, propionic acid, octylic acid, versatic acid, ethylhexanoic acid, benzoic acid, naphthenic acid, palmetic acid, stearic acid, oleic acid, fatty acids, rosin acids, and combinations thereof. ### Claim 7 (depends on 6) The process of claim 6 wherein said organic acid is acetic acid or naphthenic acid. ### Claim 8 (depends on 1) The process of claim 1 wherein said copper carboxylate is selected from the group consisting of copper acetate, copper naphthenate, copper quinolinolate, copper stearate, copper benzoate, copper ethylhexanoate, copper rosinate, and combinations thereof. ### Claim 9 (depends on 8) The process of claim 8 wherein said copper carboxylate is copper acetate or copper naphthenate. ### Claim 10 A process for producing a composition containing a zinc acrylate polymer and particles of copper pyrithione where the particles have an average aspect ratio of from about 8 to about 15 comprising the steps of: reacting an acid functional acrylic polymer with zinc pyrithione in a solvent to form a solution comprising the zinc acrylate polymer; adding a copper compound to the solution comprising zinc ester functional polymer, wherein the copper compound is selected from copper salts, copper carboxylates, copper hydroxide, elemental copper, and combinations thereof; and mixing the solution comprising the copper compound and the zinc acrylate polymer to form the particles of copper pyrithione. ### Claim 11 A process for producing a composition containing a zinc acrylate polymer and particles of copper pyrithione comprising the steps of: reacting an acid functional acrylic polymer with zinc pyrithione in a mixture of methoxypropanol and acetic acid to form a solution comprising the zinc acrylate polymer; adding a copper compound to the solution comprising zinc ester functional polymer, wherein the copper compound is selected from copper carbonate, copper nitrate, copper sulfate, copper chloride, copper carboxylates, copper hydroxide, elemental copper, and combinations thereof; and mixing the solution comprising the copper compound and the zinc acrylate polymer to form the particles of copper pyrithione, wherein the particles of copper pyrithione have an average aspect ratio of from about 8 to about 15. ### Claim 12 (depends on 10) The process of claim 10, wherein the zinc pyrithione is in the form of a wet cake. ### Claim 13 (depends on 10) The process of claim 10, further comprising the step of blending at least one water soluble resin with the zinc acrylate polymer and the copper pyrithione particles, wherein the at least one water soluble resin is selected from a group consisting of rosin, polyvinyl ether, and chitosan.