# US 11,028,285 B2 · Urethane (meth)acrylate and active energy ray-curable resin composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,028,285 B2 - Document ID: US11028285B2 - Status: Granted - Kind: B2 - Application number: 14/786,766 - Filed: 2014-01-23 - Published: 2016-03-10 - Granted: 2021-06-08 - Earliest claimed: 2013-04-26 - Assignees: Daicell-Allnex Ltd. - Applicants: Daicel-Allnex Ltd. - Inventors: Fumio Tanabiki - Web page: https://patentgrep.com/patent/US11028285B2 ## CPC - C09D 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds - C08F 299/065: {from polyurethanes with side or terminal unsaturations} - C08G 18/3206: {aliphatic} - C08G 18/3212: {containing cycloaliphatic groups} - C08G 18/3218: {containing cyclic groups having at least one oxygen atom in the ring} - C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen} - C08G 18/673: {containing two or more acrylate or alkylacrylate ester groups} - C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate} - C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates} - C08G 18/8016: {Masked aliphatic or cycloaliphatic polyisocyanates} - C08G 18/8175: {with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen} - C09D 175/16: 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) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract Provided is a compound capable of forming a coating layer that has excellent scratch resistance and still has stain resistance (in particular, stain resistance against hair dyes) and workability (impact resistance) both at satisfactory levels. The urethane (meth)acrylate has a cyclic structure in a molecule. The urethane (meth)acrylate has a total weight of carbon, oxygen, nitrogen, and sulfur atoms constituting the ring or rings of the cyclic structure of 10 percent by weight or more based on the total amount (100 percent by weight) of the urethane (meth)acrylate. The urethane (meth)acrylate also has an average number of functional groups of 3.5 to 4.5. ## Claims ### Claim 1 A urethane (meth)acrylate comprising a cyclic structure in a molecule, wherein the urethane (meth)acrylate is obtained by reacting a polyol (X), a polyisocyanate (Y), and a hydroxy-containing (meth)acrylate (Z), wherein the polyol (X) comprises an isosorbide, the urethane (meth)acrylate is prepared by reacting the polyol (X) and the polyisocyanate (Y) to form an isocyanate-containing urethane isocyanate prepolymer, and reacting the urethane isocyanate prepolymer with the hydroxy-containing (meth)acrylate (Z), the urethane (meth)acrylate has a total weight of carbon, oxygen, nitrogen, and sulfur atoms constituting a ring or rings of the cyclic structure of 10 to 27.2 percent by weight based on the total weight (100 percent by weight) of the urethane (meth)acrylate, the urethane (meth)acrylate comprises two or more different hydroxy-containing (meth)acrylates, the urethane (meth)acrylate has an average number of functional groups of 3.5 to 4.5, and the urethane (meth)acrylate comprising at least one feature selected from the group consisting of (A) and (B): (A) the cyclic structure includes at least one heterocyclic ring, and (B) the hydroxy-containing (meth)acrylate (Z) includes hydroxy-containing (meth)acrylates containing a cyclic structure in the molecule. ### Claim 2 A urethane (meth)acrylate comprising a cyclic structure in a molecule, wherein the urethane (meth)acrylate is obtained by reacting a polyol (X), a polyisocyanate (Y), and a hydroxy-containing (meth)acrylate (Z), the urethane (meth)acrylate is prepared by reacting the polyol (X) and the polyisocyanate (Y) to form an isocyanate-containing urethane isocyanate prepolymer, and reacting the urethane isocyanate prepolymer with the hydroxy-containing (meth)acrylate (Z), the urethane (meth)acrylate has a total weight of carbon, oxygen, nitrogen, and sulfur atoms constituting a ring or rings of the cyclic structure of 10 to 27.2 percent by weight based on the total weight (100 percent by weight) of the urethane (meth)acrylate, the urethane (meth)acrylate comprises two or more different hydroxy-containing (meth)acrylates, the urethane (meth)acrylate has an average number of functional groups of 3.5 to 4.5, the hydroxy-containing (meth)acrylate (Z) comprises 2-hydroxyethyl acrylate and pentaerythritol triacrylate, and the cyclic structure includes at least one polycyclic aliphatic hydrocarbon ring. ### Claim 3 (depends on 1) An active-energy-ray-curable resin composition comprising the urethane (meth)acrylate according to claim 1. ### Claim 4 (depends on 2) An active-energy-ray-curable resin composition comprising the urethane (meth)acrylate according to claim 2. ### Claim 5 (depends on 3) The active-energy-ray-curable resin composition according to claim 3, as a stain-resistant coating agent. ### Claim 6 (depends on 4) The active-energy-ray-curable resin composition according to claim 4, as a stain-resistant coating agent. ### Claim 7 (depends on 3) A cured resin layer formed by curing the active-energy-ray-curable resin composition according to claim 3. ### Claim 8 (depends on 4) A cured resin layer formed by curing the active-energy-ray-curable resin composition according to claim 4. ### Claim 9 (depends on 7) A coated article comprising: a substrate; and the cured resin layer according to claim 7 disposed on or over a surface of the substrate. ### Claim 10 (depends on 8) A coated article comprising: a substrate; and the cured resin layer according to claim 8 disposed on or over a surface of the substrate. ### Claim 11 (depends on 9) The coated article according to claim 9, wherein the cured resin layer is prepared by applying the active-energy-ray-curable resin composition to the substrate and curing the applied resin composition. ### Claim 12 (depends on 10) The coated article according to claim 10, wherein the cured resin layer is prepared by applying the active-energy-ray-curable resin composition to the substrate and curing the applied resin composition. ### Claim 13 (depends on 9) A method for producing the coated article according to claim 9, the method comprising: applying the active-energy-ray-curable resin composition to the substrate; and curing the applied resin composition to form the cured resin layer. ### Claim 14 (depends on 10) A method for producing the coated article according to claim 10, the method comprising: applying the active-energy-ray-curable resin composition to the substrate; and curing the applied resin composition to form the cured resin layer. ### Claim 15 (depends on 2) The urethane (meth)acrylate according to claim 2, wherein the polyisocyanate (Y) comprises an isophorone diisocyanate. ### Claim 16 (depends on 2) The urethane (meth)acrylate according to claim 2, wherein the polyol (X) comprises a tricyclodecanedimethanol. ### Claim 17 (depends on 16) The urethane (meth)acrylate according to claim 16, wherein the polyisocyanate (Y) comprises an isophorone diisocyanate.