# US 10,479,908 B2 · Method of manufacturing hard coat film > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,479,908 B2 - Document ID: US10479908B2 - Status: Granted - Kind: B2 - Application number: 15/782,248 - Filed: 2017-10-12 - Published: 2018-02-15 - Granted: 2019-11-19 - Earliest claimed: 2014-03-31 - Assignees: FUJIFILM Corporation - Applicants: FUJIFILM Corporation - Inventors: Akio Tamura; Katsuyuki Takada; Takayasu Yamazaki; Keisuke Oku; Keigo Ueki - Web page: https://patentgrep.com/patent/US10479908B2 ## CPC - C08F 222/1065: {of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates} - B05D 3/007: {After-treatment} - C08F 222/106: {Esters of polycondensation macromers} - C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} - C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen - B05D 7/02: to macromolecular substances, e.g. rubber (treatment or coating of shaped articles made of macromolecular substances C08J7/00) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - 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 An aspect of the present invention relates to method of manufacturing a hard coat film, wherein the hard coat film comprises a plastic substrate and a hard coat layer, the method comprises forming the hard coat layer by subjecting a photopolymerizable hard coating composition to photopolymerization processing, and the photopolymerizable hard coating composition comprises a radical polymerizable compound having two or more radical polymerizable groups selected from the group consisting of acryloyloxy groups, acryloyl groups, methacryloyloxy groups, and methacryloyl groups per molecule, a cationic polymerizable compound, a radical photopolymerization initiator, and a cationic photopolymerization initiator. ## Claims ### Claim 1 A composition, which is a photopolymerizable hard coating composition comprising: a radical polymerizable compound having two or more radical polymerizable groups selected from the group consisting of acryloyloxy groups, acryloyl groups, methacryloyloxy groups, and methacryloyl groups per molecule; a cationic polymerizable compound; a radical photopolymerization initiator; and a cationic photopolymerization initiator, wherein the cationic polymerizable compound comprises a cyclic structure-containing compound, wherein the cyclic structure-containing compound contains a nitrogen-containing hetero ring-containing compound, and wherein the nitrogen-containing hetero ring-containing compound contains one or more nitrogen-containing hetero ring selected from the group consisting of isocyanurate rings and glycoluril rings per molecule. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the radical polymerizable compound is a urethane bond-containing compound containing one or more urethane bonds per molecule. ### Claim 3 (depends on 2) The composition according to claim 2, wherein the urethane bond-containing compound contains two or more urethane bonds per molecule. ### Claim 4 (depends on 1) The composition according to claim 1, wherein the nitrogen-containing hetero ring-containing compound contains an isocyanurate ring-containing compound. ### Claim 5 (depends on 1) The composition according to claim 1, wherein the cationic polymerizable compound contains a cationic polymerizable compound having a cationic polymerizable group equivalence of less than 150 obtained by dividing the molecular weight by the number of cationic polymerizable groups contained per molecule. ### Claim 6 (depends on 5) The composition according to claim 5, wherein the cationic polymerizable compound with a cationic polymerizable group equivalence of less than 150 is an epoxy ring-containing compound in which the epoxy equivalence obtained by dividing the molecular weight by the number of epoxy rings contained per molecule is less than 150. ### Claim 7 (depends on 1) The composition according to claim 1, wherein the cationic polymerizable compound contains one or more functional groups having an ethylenic unsaturated double bond per molecule. ### Claim 8 (depends on 1) The composition according to claim 1, wherein the molecular weight of the cationic polymerizable compound is 500 or less. ### Claim 9 (depends on 1) The composition according to claim 1, wherein the molecular weight of the cationic polymerizable compound is 300 or less. ### Claim 10 (depends on 1) The composition according to claim 1, which contains 0.05 to 50 weight parts of the cationic polymerizable compound per 100 weight parts of the combined contents of the cationic polymerizable compounds and the radical polymerizable compounds. ### Claim 11 (depends on 1) A hard coat film, which comprises: a plastic substrate; and a hard coat layer formed by subjecting the composition according to claim 1 to photopolymerization processing. ### Claim 12 (depends on 11) The hard coat film according to claim 11, wherein the plastic substrate contains at least one film selected from the group consisting of acrylic resin films and polycarbonate resin films. ### Claim 13 (depends on 11) The hard coat film according to claim 11, wherein the plastic substrate is a laminate film of two or more layers of resin film. ### Claim 14 (depends on 11) An article, which comprises a hard coat film according to claim 11. ### Claim 15 (depends on 14) The article according to claim 14, which comprises the hard coat film as a protective surface film.