# US 12,180,387 B2 · Coating composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,387 B2 - Document ID: US12180387B2 - Status: Granted - Kind: B2 - Application number: 17/258,487 - Filed: 2019-07-17 - Published: 2021-09-09 - Granted: 2024-12-31 - Earliest claimed: 2018-07-20 - Assignees: Covestro Deutschland AG - Applicants: Covestro Intellectual Property GmbH & Co. KG - Inventors: Dorota Greszta-Franz; Jianping Shen; Junchao Zheng; Yifeng Xu; Ling Yang; Jinqi Li; Hongchao Li; Hao Liu - Web page: https://patentgrep.com/patent/US12180387B2 ## CPC - C09D 175/02: Polyureas - C09D 175/12: from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/3253: {being in latent form} - C08G 18/3256: {Reaction products of polyamines with aldehydes or ketones} - C08G 18/3821: {Carboxylic acids; Esters thereof with monohydroxyl compounds} - C08G 18/5021: {having nitrogen} - C08G 18/721: {Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80} - C08G 18/73: acyclic - C08G 18/7657: {containing two or more aromatic rings} - C08G 18/7831: {containing biuret groups} - C08G 18/79: characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates - C09D 175/04: Polyurethanes - 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract The present invention relates to a coating composition, a coating method and use of the composition, and a product coated with the coating composition. The coating composition comprises: (a) an isocyanate-reactive component comprising: (a1) at least one polyaspartic ester, and (a2) optionally a polyetheraspartic ester; (b) an isocyanate component comprising: (b1) at least one isocyanate prepolymer having an isocyanate group equivalent of 300 to 1100, and (b2) at least one isocyanate oligomer containing not less than two isocyanate groups, the weight ratio of the isocyanate prepolymer (b1) to the isocyanate oligomer (b2) being from 1:4 to 4:1; (c) a catalyst; and (d) optionally an additive; wherein the coating composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of 1.5:1 to 8:1. The coating composition provided by the present invention has a long pot life, and the resulting coating has the advantages of fast drying and high hardness. ## Claims ### Claim 1 A coating composition comprising: (a) an isocyanate-reactive component comprising: (a1) at least one polyaspartic ester, and (a2) optionally a polyetheraspartic ester; (b) an isocyanate component comprising: (b1) at least one isocyanate prepolymer having an isocyanate group equivalent of 300 to 1100, and (b2) at least one isocyanate oligomer containing not less than two isocyanate groups, a weight ratio of the isocyanate prepolymer (b1) to the isocyanate oligomer (b2) being from 1:4 to 4:1; (c) a catalyst, wherein the catalyst is one or more of the following: a tertiary amine, ferric chloride, zinc chloride, bismuth isooctanoate or bismuth carboxylate; and (d) optionally an additive; wherein the coating composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of 1.5:1 to 8:1. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the polyaspartic ester (a1) comprises a polyaspartic ester according to formula I: wherein X represents an aliphatic residue, R1 and R2 are each independently an organic group that is inert to an isocyanate group at ambient pressure and at 100° C. or less, and n is an integer of not less than 2. ### Claim 3 (depends on 2) The composition according to claim 2, wherein the aliphatic residue of the polyaspartic ester (a1) is one or more of the following: a linear alkyl residue, a branched alkyl residue, or a cycloalkyl residue. ### Claim 4 (depends on 1) The composition according to claim 1, wherein the polyaspartic ester (a1) has a content of more than 50 wt %, based on a total weight of the isocyanate-reactive component (a). ### Claim 5 (depends on 2) The composition according to claim 2, wherein n is 2 and the polyaspartic ester (a1) is prepared by a reaction comprising a polyamine of the following formula and a maleate and/or a fumarate of the following formula: ### Claim 6 (depends on 2) The composition according to claim 2, wherein the polyaspartic ester (a1) comprises one or more of the following polyaspartic esters: (i) a polyaspartic ester having the structure of formula II, (ii) a polyaspartic ester having the structure of formula III, or (iii) a polyaspartic ester having the structure of formula IV, wherein R1 and R2 are each independently one or more of the following: methyl, ethyl or butyl. ### Claim 7 (depends on 1) The composition according to claim 1, wherein the polyetheraspartic ester (a2) comprises a polyetheraspartic ester according to formula V: wherein Z represents an aliphatic residue, R1 and R2 are each independently an organic group that is inert to an isocyanate group at ambient pressure and at 100° C. or less, R3 represents a C1-C6 alkyl residue, n is an integer of not less than 2, and m is an integer of 1 to 5. ### Claim 8 (depends on 7) The composition according to claim 7, wherein the aliphatic residue of the polyetheraspartic ester (a2) is one or more of the following: a linear alkyl residue, a branched alkyl residue, or a cycloalkyl residue. ### Claim 9 (depends on 1) The composition according to claim 1, wherein the polyetheraspartic ester (a2) is prepared by a reaction comprising a polyether polyamine of the following formula and a maleate and/or a fumarate of the following formula: wherein p is an integer of not less than 2, R1 and R2 are each independently an organic group that is inert to an isocyanate group at ambient pressure and at 100° C. or less, R4 and R5 are each independently one or more of the following: hydrogen or a C1-C4 alkyl residue, R6 and R7 are each independently one or more of the following: hydrogen or an organic group inert to an isocyanate group. ### Claim 10 (depends on 9) The composition according to claim 9, wherein the components for preparing the polyetheraspartic ester (a2) further comprise a polyether polyamine according to the following formula: wherein Y′ is one or more of the following: a linear alkyl residue, a branched alkyl residue, or a cycloalkyl residue, q is an integer of 1 to 35, R8 is a C1-C6 alkyl residue. ### Claim 11 (depends on 1) The composition according to claim 1, wherein the polyetheraspartic ester (a2) comprises a polyetheraspartic ester according to formula VI: wherein r is an integer of 2 to 4, q is an integer of 1 to 35, Y′ is an alkyl residue, R1 and R2 are each independently an organic group that is inert to an isocyanate group at ambient pressure and at 100° C. or less, R8 is a C1-C6 alkyl residue. ### Claim 12 (depends on 1) The composition according to claim 1, wherein the isocyanate prepolymer (b1) comprises one or more of the following groups: a carbamate group or an allophanate group. ### Claim 13 (depends on 1) The composition according to claim 1, wherein the isocyanate prepolymer (b1) has an isocyanate group content of 1 to 40 wt %, based on a total weight of the isocyanate prepolymer. ### Claim 14 (depends on 1) The composition according to claim 1, wherein the isocyanate oligomer (b2) comprises one or more of the following groups: an allophanate group, a biuret group, an uretdione group, an isocyanurate group, or an iminooxadiazinedione group. ### Claim 15 (depends on 1) The composition according to claim 1, wherein the isocyanate oligomer (b2) is one or more of the following: derivatives of an aliphatic triisocyanate or an alicyclic triisocyanate having one or more of allophanate, biuret, uretdione, isocyanurate, or iminooxadiazinedione groups. ### Claim 16 (depends on 1) The composition according to claim 1, wherein the isocyanate oligomer (b2) has an isocyanate group content of 10 to 50 wt %, based on a total weight of the isocyanate oligomer. ### Claim 17 (depends on 1) A method of protecting a substrate surface or a coating thereof, comprising applying the coating composition of claim 1 to a substrate surface or the coating thereof, followed by curing and/or drying. ### Claim 18 (depends on 1) A coating method comprising applying the coating composition of claim 1 to a substrate surface, followed by curing and/or drying. ### Claim 19 (depends on 1) A coated product comprising a substrate and a coating formed by applying the coating composition of claim 1 to the substrate and then curing and/or drying. ### Claim 20 (depends on 19) The coated product according to claim 19, wherein the coated product is a floor.