# US 11,306,174 B2 · Curable film-forming compositions demonstrating decreased cure time with stable pot life > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,306,174 B2 - Document ID: US11306174B2 - Status: Granted - Kind: B2 - Application number: 16/611,763 - Filed: 2018-03-01 - Published: 2020-03-26 - Granted: 2022-04-19 - Earliest claimed: 2017-05-08 - Assignees: PPG Industries Ohio, Inc. - Applicants: PPG Industries Ohio, Inc. - Inventors: Silvia Bezer; Steven R. Zawacky; Diane Schillinger - Web page: https://patentgrep.com/patent/US11306174B2 ## CPC - C08G 18/161: {containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22} - C08G 18/42: Polycondensates having carboxylic or carbonic ester groups in the main chain - C08G 18/168: {Organic compounds} - C08G 18/222: {metal compounds not provided for in groups C08G18/225 - C08G18/26} - C08G 18/246: {containing also tin-carbon bonds} - C08G 18/70: characterised by the isocyanates or isothiocyanates used - C09D 175/06: from polyesters - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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) ## Abstract The present invention is directed to an aqueous curable film-forming composition comprising: (a) a film-forming component comprising an aliphatic di- or higher functional polyisocyanate; and (b) a catalyst additive comprising: (i) a catalytic organic compound comprising iron and/or tin; and (ii) a beta-diketone. The present invention is further directed to a method of controlling the rate of cure of an aqueous curable film-forming composition. The method comprises adding to the aqueous curable film-forming composition the catalyst additive described above; the aqueous curable film-forming composition comprises a film-forming component comprising an aliphatic di- or higher functional polyisocyanate. The present invention is additionally directed to a coated article comprising a cured coating layer applied on at least one surface of a substrate to form a coated substrate; wherein the cured coating layer is deposited from the aqueous curable film-forming composition described above. ## Claims ### Claim 1 A curable, aqueous film-forming composition comprising: (a) a film-forming component comprising an aliphatic di- or higher functional polyisocyanate; and (b) a catalyst additive comprising: (i) a catalytic organic compound comprising iron; and (ii) a beta-diketone. ### Claim 2 (depends on 1) The curable film-forming composition of claim 1, wherein the polyisocyanate has an average isocyanate functionality greater than two. ### Claim 3 (depends on 1) The curable film-forming composition of claim 1, wherein the film-forming component (a) further comprises a film-forming polymer that is different from the polyisocyanate, comprising functional groups reactive with isocyanate functional groups in the polyisocyanate. ### Claim 4 (depends on 3) The curable film-forming composition of claim 3, wherein the film-forming polymer comprises an acrylic polymeric polyol, a polyether polymeric polyol, and/or a polyester polymeric polyol. ### Claim 5 (depends on 3) The curable film-forming composition of claim 3, wherein the equivalent ratio of isocyanate groups in the polyisocyanate to the reactive functional groups in the film-forming polymer is higher than 2:1. ### Claim 6 (depends on 5) The curable film-forming composition of claim 5, wherein the equivalent ratio of isocyanate groups in the polyisocyanate to the reactive functional groups in the film-forming polymer is at least 5:1. ### Claim 7 (depends on 1) The curable film-forming composition of claim 1, wherein the catalyst additive (b) further comprises (iii) a tertiary amine. ### Claim 8 (depends on 7) The curable film-forming composition of claim 7, wherein the tertiary amine (iii) comprises dimethylcyclohexylamine, diethylcyclohexylamine, dimethylethanolamine, a dimethylethanolamine ether, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane, and/or triethylamine. ### Claim 9 (depends on 7) The curable film-forming composition of claim 7, wherein the molar ratio of catalytic organic compound (i) to tertiary amine (iii) ranges from 0.05 to 0.10. ### Claim 10 (depends on 1) The curable film-forming composition of claim 1, wherein the catalytic organic compound (i) comprises ferric acetylacetonate. ### Claim 11 (depends on 1) The curable film-forming composition of claim 1, wherein the catalytic organic compound (i) is present in the curable film-forming composition in an amount of 0.10 to 0.8 percent by weight, based on the total weight of resin solids in the curable film-forming composition. ### Claim 12 (depends on 1) The curable film-forming composition of claim 1, wherein the beta-diketone (ii) comprises 2,4-pentanedione and/or 3-methyl-2,4-pentanedione. ### Claim 13 (depends on 1) The curable film-forming composition of claim 1, wherein the beta-diketone (ii) is present in the curable film-forming composition in an amount of 4 to 50 percent by weight, based on the total weight of resin solids in the curable film-forming composition. ### Claim 14 (depends on 3) The curable film-forming composition of claim 3, wherein the composition is a two-package composition, and each component of the catalyst additive (b) is independently present with the polyisocyanate in a first package and/or with the film-forming polymer in a second package. ### Claim 15 (depends on 3) A chemical agent resistant coating formed from the curable film-forming composition of claim 3. ### Claim 16 A method of controlling the rate of cure of an aqueous curable film-forming composition, comprising adding to the aqueous curable film-forming composition a catalyst additive comprising: (i) a catalytic organic compound comprising iron; and (ii) a beta-diketone; wherein the aqueous curable film-forming composition comprises a film-forming component comprising an aliphatic di- or higher functional polyisocyanate. ### Claim 17 (depends on 16) The method of claim 16, wherein the film-forming component further comprises a polymer that is different from the polyisocyanate, comprising functional groups reactive with isocyanate functional groups in the polyisocyanate. ### Claim 18 (depends on 16) The method of claim 16, wherein the catalytic organic compound (i) comprises ferric acetylacetonate. ### Claim 19 (depends on 16) The method of claim 16, wherein the catalyst additive further comprises (iii) a tertiary amine. ### Claim 20 (depends on 19) The method of claim 19, wherein tertiary amine (iii) comprises dimethylcyclohexylamine, dimethylethanolamine, and/or dimethylethanolamine ether. ### Claim 21 (depends on 16) The method of claim 16, wherein the beta-diketone (ii) comprises 2,4-pentanedione and/or 3-methyl-2,4-pentanedione. ### Claim 22 (depends on 1) A coated article comprising: (A) a substrate having at least one coatable surface; and (B) a cured coating layer applied on at least one surface of the substrate to form a coated substrate; wherein the cured coating layer is deposited from the aqueous curable film-forming composition of claim 1. ### Claim 23 (depends on 22) The coated article of claim 22, wherein a primer coating layer is applied to the surface of the substrate prior to the application of the aqueous curable film-forming composition. ### Claim 24 (depends on 22) The coated article of claim 22, wherein said coated article comprises an aircraft or military land vehicle. ### Claim 25 (depends on 3) A coated article comprising: (A) a substrate having at least one coatable surface; and (B) a cured coating layer applied on at least one surface of the substrate to form a coated substrate; wherein the cured coating layer is deposited from the aqueous curable film-forming composition of claim 3.