# US 11,898,053 B2 · Active energy ray-curable resin composition, anti-fogging and anti-fouling laminate, method for producing same, article, and anti-fogging method > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,898,053 B2 - Document ID: US11898053B2 - Status: Granted - Kind: B2 - Application number: 16/961,766 - Filed: 2019-10-17 - Published: 2021-11-25 - Granted: 2024-02-13 - Earliest claimed: 2018-10-24 - Assignees: Dexerials Corporation - Applicants: Dexerials Corporation - Inventors: Ryo Suzuki; Shinobu Hara; Mikihisa Mizuno - Web page: https://patentgrep.com/patent/US11898053B2 ## CPC - C03C 17/002: {for flat glass, e.g. float glass} - C09D 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds - C03C 17/28: with organic material (C03C17/34, C03C17/44 take precedence) - C03C 17/3405: {with at least two coatings of organic materials (C03C17/36, C03C17/42 take precedence)} - C08F 283/008: {on to unsaturated polymers} - C08F 290/067: {Polyurethanes; Polyureas} - C09D 5/002: {Priming paints (C09D5/08 takes precedence)} - G02B 1/18: Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence) - C03C 2217/75: Hydrophilic and oleophilic coatings - C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS - 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 - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS ## Abstract An anti-fogging and anti-fouling laminate including: a substrate; and an anti-fogging and anti-fouling layer on the substrate, the anti-fogging and anti-fouling layer having a flat surface, wherein a hexadecane contact angle of the anti-fogging and anti-fouling layer is 10° or less, the anti-fogging and anti-fouling layer is a cured product of an active energy ray-curable resin composition, and the active energy ray-curable resin composition includes a hydrophilic monomer. ## Claims ### Claim 1 An anti-fogging and anti-fouling laminate comprising: a substrate; and an anti-fogging and anti-fouling layer on the substrate, the anti-fogging and anti-fouling layer having a flat surface, wherein a hexadecane contact angle of the anti-fogging and anti-fouling layer is 10° or less, the anti-fogging and anti-fouling layer is a cured product of an active energy ray-curable resin composition, and the active energy ray-curable resin composition includes: (a) a bi- or more functional urethane (meth)acrylate, (b) a hydrophilic monomer including a hydrophilic group and a (meth)acryloyl group, and (c) a bi- or more functional (meth)acrylate having an acryl equivalent of less than 400, selected from the group consisting of pentaerythritol triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated glycerin triacrylate, pentaerythritol alkoxy tetraacrylate, and tricylodecane dimethanol diacrylate, wherein the active energy ray-curable resin composition is free of a hydrophobic monomer which does not include the hydrophilic group and has the water-repellent molecular structure, and wherein an amount of the hydrophilic monomer is more than 0% by mass but 10% by mass or less relative to non-volatile matter of the active energy ray-curable resin composition. ### Claim 2 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, further comprising: a primer layer between the substrate and the anti-fogging and anti-fouling layer. ### Claim 3 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, wherein a surface free energy of the anti-fogging and anti-fouling layer is 30 mJ/m2 or more but 65 mJ/m2 or less. ### Claim 4 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, wherein a water contact angle of the anti-fogging and anti-fouling layer is 30° or more but 90° or less. ### Claim 5 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, wherein Martens hardness of the anti-fogging and anti-fouling layer is 200 N/mm2 or more. ### Claim 6 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, wherein a coefficient of kinetic friction of the anti-fogging and anti-fouling layer is 0.90 or less. ### Claim 7 (depends on 1) The anti-fogging and anti-fouling laminate according to claim 1, wherein the substrate is a mirror, and b* value of reflection hue in the anti-fogging and anti-fouling layer is 5 or less. ### Claim 8 (depends on 1) An article comprising: the anti-fogging and anti-fouling laminate according to claim 1 on a surface of the article. ### Claim 9 (depends on 1) A method for producing the anti-fogging and anti-fouling laminate according to claim 1, the method comprising: irradiating an uncured layer formed of the active energy ray-curable resin composition with ultraviolet rays under an atmosphere having an oxygen concentration of less than 1.0% by volume to form the anti-fogging and anti-fouling layer. ### Claim 10 (depends on 1) An anti-fogging method comprising: warming the anti-fogging and anti-fouling laminate according to claim 1 to a temperature equal to or higher than normal temperature to improve an anti-fogging property of the anti-fogging and anti-fouling layer. ### Claim 11 (depends on 1) An anti-fogging method comprising: cleaning the anti-fogging and anti-fouling layer of the anti-fogging and anti-fouling laminate according to claim 1 to maintain an anti-fogging property of the anti-fogging and anti-fouling layer. ### Claim 12 An active energy ray-curable resin composition comprising: (a) a bi- or more functional urethane (meth)acrylate, (b) a hydrophilic monomer including a hydrophilic group and a (meth)acryloyl group, and (c) a bi- or more functional (meth)acrylate having an acryl equivalent of less than 400, selected from the group consisting of pentaerythritol triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated glycerin triacrylate, pentaerythritol alkoxy tetraacrylate, and tricylodecane dimethanol diacrylate, wherein the active energy ray-curable resin composition is free of a hydrophobic monomer which does not include the hydrophilic group and has the water-repellent molecular structure, and an amount of the hydrophilic monomer is more than 0% by mass but 10% by mass or less relative to non-volatile matter of the active energy ray-curable resin composition. ### Claim 13 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein an anti-fogging and anti-fouling layer having a flat surface, which is obtained by curing the active energy ray-curable resin composition with active energy rays, has a hexadecane contact angle of 10° or less. ### Claim 14 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein an anti-fogging and anti-fouling layer having a flat surface, which is obtained by curing the active energy ray-curable resin composition with active energy rays, has a surface free energy of 30 mJ/m2 or more but 65 mJ/m2 or less. ### Claim 15 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein an anti-fogging and anti-fouling layer having a flat surface, which is obtained by curing the active energy ray-curable resin composition with active energy rays, has a water contact angle of 30° or more but 90° or less. ### Claim 16 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein an anti-fogging and anti-fouling layer having a flat surface, which is obtained by curing the active energy ray-curable resin composition with active energy rays, has Martens hardness of 200 N/mm2 or more. ### Claim 17 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein an anti-fogging and anti-fouling layer having a flat surface, which is obtained by curing the active energy ray-curable resin composition with active energy rays, has a coefficient of kinetic friction of 0.90 or less. ### Claim 18 (depends on 12) The active energy ray-curable resin composition according to claim 12, wherein b* value of reflection hue in an anti-fogging and anti-fouling layer having a flat surface is 5 or less, the anti-fogging and anti-fouling layer being obtained by curing the active energy ray-curable resin composition on a mirror that is a substrate with active energy rays.