# US 11,111,410 B2 · Dual cure soft touch coatings > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,111,410 B2 - Document ID: US11111410B2 - Status: Granted - Kind: B2 - Application number: 16/081,086 - Filed: 2017-02-21 - Published: 2019-03-28 - Granted: 2021-09-07 - Earliest claimed: 2016-03-02 - Assignees: Arkema France - Applicants: Arkema France - Inventors: Lisa Marie Spagnola; Jeffrey Klang; Manjuli Gupta - Web page: https://patentgrep.com/patent/US11111410B2 ## CPC - C09D 175/16: having terminal carbon-to-carbon unsaturated bonds - C08G 18/42: Polycondensates having carboxylic or carbonic ester groups in the main chain - C08G 18/6254: {Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups} - C08G 18/67: Unsaturated compounds having active hydrogen - C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen} - C08G 18/6795: {Unsaturated polyethers} - C08G 18/81: Unsaturated isocyanates or isothiocyanates - C08G 18/8175: {with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen} - C08L 75/16: having terminal carbon-to-carbon unsaturated 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Coatings having a favorable combination of “soft touch” characteristics and durability are obtained by dual curing compositions containing free radical-curable ethylenically unsaturated compound(s), polyol(s) and polyisocyanate(s). ## Claims ### Claim 1 A coating composition comprised of at least one free radical-curable ethylenically unsaturated compound, at least one polyol and at least one polyisocyanate, wherein the at least one free radical-curable ethylenically unsaturated compound includes at least one isocyanurate tri(meth)acrylate or derivative thereof or at least one isocyanate functionality-containing urethane (meth)acrylate and the weight ratio of (polyol+polyisocyanate): free radical-curable ethylenically unsaturated compound is from 1:1 to 10:1. ### Claim 2 (depends on 1) The coating composition of claim 1, wherein the at least one free radical-curable ethylenically unsaturated compound includes the at least one isocyanurate tri(meth)acrylate or derivative thereof. ### Claim 3 (depends on 1) The coating composition of claim 1, wherein the at least one free radical-curable ethylenically unsaturated compound includes at least one urethane diacrylate. ### Claim 4 (depends on 1) The coating composition of claim 1, wherein the at least one free radical-curable ethylenically unsaturated compound includes the at least one isocyanurate tri(meth)acrylate or derivative thereof and further includes at least one urethane diacrylate. ### Claim 5 (depends on 1) The coating composition of claim 1, wherein the at least one free radical-curable ethylenically unsaturated compound includes the at least one isocyanate functionality-containing urethane acrylate. ### Claim 6 (depends on 1) The coating composition claim 1, wherein the at least one free radical-curable ethylenically unsaturated compound includes the at least one isocyanate-reactive functionality-containing urethane (meth)acrylate. ### Claim 7 (depends on 1) The coating composition of claim 1, further comprising at least one photoinitiator. ### Claim 8 (depends on 1) The coating composition of claim 1, further comprising at least one free radical initiator that decomposes when heated or in the presence of an accelerator. ### Claim 9 (depends on 1) The coating composition of claim 1, further comprising at least one matting agent. ### Claim 10 (depends on 1) The coating composition of claim 1, further comprising at least one non-reactive solvent. ### Claim 11 (depends on 1) The coating composition of claim 1, wherein the coating composition is free of non-reactive solvent. ### Claim 12 (depends on 1) The coating composition of claim 1, wherein the coating composition is water-borne. ### Claim 13 (depends on 1) The coating composition of claim 1, wherein the at least one polyol includes one or more polyols selected from the group consisting of polyester polyols, polyether polyols, polycarbonate polyols, polycarbonate polyester polyols, polyacrylic polyols, polyurethane polyols, polycaprolactone polyols, polyolefin polyols and combinations thereof. ### Claim 14 (depends on 1) The coating composition of claim 1, wherein the at least one polyisocyanate includes one or more polyisocyanates selected from the group consisting of aromatic polyisocyanates, aliphatic polyisocyanates and cycloaliphatic polyisocyanates. ### Claim 15 (depends on 1) The coating composition of claim 1, wherein the coating composition is comprised of at least one polyol, at least one polyisocyanate, at least one non-reactive solvent, at least one urethane diacrylate, at least one isocyanurate tri(meth)acrylate, at least one matting agent and at least one photoinitiator. ### Claim 16 (depends on 1) The coating composition of claim 1, wherein the coating composition is comprised of at least one polyol, at least one polyisocyanate, at least one non-reactive solvent, at least one isocyanate functionality-containing urethane acrylate, at least one matting agent and at least one photoinitiator. ### Claim 17 (depends on 1) The coating composition of claim 1, wherein the coating composition is packaged in the form of two separate parts as follows: a-1) a Part A-1 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyisocyanate; and b-1) a Part B-1 comprised of at least one polyol; or a-2) a Part A-2 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyol; and b-2) a Part B-2 comprised of at least one polyisocyanate. ### Claim 18 (depends on 1) A method of forming a coating on a surface of a substrate, comprising the steps of applying at least one layer of the coating composition of claim 1, to the surface of the substrate, exposing the coating composition to an amount of radiation and/or of heat effective to initiate cure of the at least one free radical-curable ethylenically unsaturated compound and reacting the at least one polyol and the at least one polyisocyanate. ### Claim 19 (depends on 18) The method of claim 18, wherein the coating composition is prepared by mixing a first part comprised of the at least one free radical-curable ethylenically unsaturated compound and the at least one polyol with a second part comprised of the at least one polyisocyanate or by mixing a first part comprised of the at least one polyol and a second part comprised of the at least one polyisocyanate and the at least one free radical-curable ethylenically unsaturated compound. ### Claim 20 (depends on 18) The method of claim 18, wherein the coating composition is heated after being applied to the surface of the substrate. ### Claim 21 (depends on 18) The method of claim 18, wherein the coating composition is heated after exposing the coating composition to the amount of radiation effective to initiate cure of the at least one free-radical curable ethylenically unsaturated compound. ### Claim 22 (depends on 18) The method of claim 18, wherein the coating composition is exposed to the amount of radiation effective to initiate cure of the at least one free-radical curable ethylenically unsaturated compound, after heating the coating composition. ### Claim 23 (depends on 1) A precursor composition useful for forming a coating composition as defined in claim 1, when said precursor composition is combined with at least one polyol, wherein the precursor composition is comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyisocyanate, said precursor composition being free of any polyol. ### Claim 24 (depends on 1) A precursor composition useful for forming a coating composition as defined in claim 1, when said precursor composition is combined with at least one polyisocyanate, wherein the precursor composition is comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyol, said precursor composition being free of any polyisocyanate. ### Claim 25 (depends on 1) A two part system useful for forming a coating composition as defined according to claim 1, comprising as separately packaged components, either: a-1) a Part A-1 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyisocyanate; and b-1) a Part B-1 comprised of at least one polyol; or a-2) a Part A-2 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyol; and b-2) a Part B-2 comprised of at least one polyisocyanate. ### Claim 26 (depends on 25) A method of making a coating, comprising combining Part A-1 and Part B-1 of claim 25 or combining Part A-2 and Part B-2 of claim 25 to form a coating composition, applying the coating composition to a surface of a substrate and curing the applied coating composition. ### Claim 27 (depends on 1) A coating comprised of at least one layer of a coating composition in accordance with claim 1, wherein the coating composition is cured. ### Claim 28 (depends on 1) An article of manufacture comprised of a substrate, wherein a surface of the substrate is at least partially coated with a coating composition in accordance with claim 1. ### Claim 29 (depends on 28) The article of manufacture of claim 28, wherein the surface of the substrate is comprised of at least one material selected from the group consisting of thermosets, thermoplastics, metals, wood, leather, glass, paper, cardboard and combinations thereof. ### Claim 30 A coating composition comprised of at least one free radical-curable ethylenically unsaturated compound, at least one polyol, at least one polyisocyanate, and at least one matting agent, wherein the at least one free radical-curable ethylenically unsaturated compound includes at least one isocyanurate tri(meth)acrylate or derivative thereof or at least one isocyanate functionality-containing urethane (meth)acrylate and the weight ratio of (polyol+polyisocyanate): free radical-curable ethylenically unsaturated compound is from 1:1 to 10:1, and wherein the coating composition is packaged in the form of two separate parts as follows: a-1) a Part A-1 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyisocyanate; and b-1) a Part B-1 comprised of at least one polyol; or a-2) a Part A-2 comprised of at least one free radical-curable ethylenically unsaturated compound and at least one polyol; and b-2) a Part B-2 comprised of at least one polyisocyanate.