# US 8,540,925 B2 · Photocurable composition, micropattern-formed product and its production process > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,540,925 B2 - Document ID: US8540925B2 - Status: Granted - Kind: B2 - Application number: 11/876,182 - Filed: 2007-10-22 - Published: 2008-05-08 - Granted: 2013-09-24 - Earliest claimed: 2005-04-21 - Assignees: Asahi Glass Company, Limited - Applicants: Yasuhide Kawaguchi; Akihiko Asakawa - Inventors: Yasuhide Kawaguchi; Akihiko Asakawa - Web page: https://patentgrep.com/patent/US8540925B2 ## CPC - B29C 37/0053: {Moulding articles characterised by the shape of the surface, e.g. ribs, high polish (mould construction therefor B29C33/42; surface shaping of articles B29C59/00; by incorporating filler in or near the surface B29C70/64)} - B29C 43/003: {characterised by the choice of material} - B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic - B82Y 40/00: Manufacture or treatment of nanostructures - C08F 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate} - C08F 220/24: containing perhaloalkyl radicals - C08F 222/1065: {of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates} - G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping} - G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)} - G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) - B29C 35/0888: {using transparant moulds} - B29C 43/021: {characterised by the shape of the surface} - B29C 2035/0833: {using actinic light} - B29C 2043/3634: {having specific surface shape, e.g. grooves, projections, corrugations} - B29C 2059/023: {Microembossing} - B29K 2105/0002: {monomers or prepolymers} - B29L 2011/0016: {Lenses} - Y10T 428/24479: including variation in thickness - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) - B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS - B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A photocurable composition capable of producing a micropattern-formed product efficiently, which is excellent in physical properties such as heat resistance, chemical resistance, releasability and optical characteristics (transmittance and low refractive index), and a process for producing a micropattern-formed product, capable of highly precisely transferring a micropattern of a mold to its surface are provided. A photocurable composition which comprises from 50 to 98 mass % of a monomer containing no fluorine atom and having a viscosity at 25° C. of from 0.1 to 100 mPa·s, from 0.1 to 45 mass % of a fluoromonomer, from more than 0.1 to 20 mass % of a fluorinated surfactant and/or a fluoropolymer and from 1 to 10 mass % of a photopolymerization initiator, and contains substantially no solvent. A process for producing a micropattern-formed product comprising a cured product having a micropattern of a mold transferred on its surface, or such a micropattern-formed product integrated with a substrate, which uses the photocurable composition, a substrate and a mold having a micropattern. ## Claims ### Claim 1 A process for producing a micropattern-formed product, which comprises bringing a photocurable composition which comprises from 50 to 98 mass % of a monomer containing no fluorine atom and having a viscosity at 25° C. of from 0.1 to 100 mPa·s, from 0.1 to 45 mass % of a fluoromonomer, from more than 0.1 to 20 mass % of a fluorinated surfactant and/or a fluoropolymer and from 1 to 10 mass % of a photopolymerization initiator, and contains substantially no solvent, into contact with the micropatterned surface of a mold having a micropattern formed on the surface, photo-curing the photocurable composition in a state where it is in contact with the surface of the mold, and separating a cured product of the photocurable composition from the mold. ### Claim 2 (depends on 1) The process for producing a micropattern-formed product according to claim 1, wherein the micropattern of the mold is a micropattern having convex portions and concavo portions, and the average interval of the convex portions is from 1 nm to 500 μm. ### Claim 3 (depends on 1) The process of claim 1, wherein the photocurable composition comprises an adamantyl group-containing acrylate monomer unit and a polyoxyalkylene acrylate monomer unit. ### Claim 4 (depends on 1) The method of claim 1, wherein the photocurable composition comprises a fluoroacrylate monomer unit. ### Claim 5 (depends on 1) The method of claim 1, wherein the photocurable composition comprises a fluoropolymer surfactant. ### Claim 6 (depends on 5) The method of claim 5, wherein the fluoropolymer surfactant consists of C atoms, F atoms, H atoms, and O atoms. ### Claim 7 A process for producing a micropattern-formed product, which comprises carrying out the following steps A, B, C and as the case requires, step D, in this order with a photocurable composition comprising from 50 to 98 mass % of a monomer containing no fluorine atom and having a viscosity at 25° C. of from 0.1 to 100 mPa·s, from 0.1 to 45 mass % of a fluoromonomer, from more than 0.1 to 20 mass % of a fluorinated surfactant and/or a fluoropolymer and from 1 to 10 mass % of a photopolymerization initiator, and contains substantially no solvent, a substrate and a mold having a micropattern on its surface to obtain a micropattern-formed product having a micropattern on its surface or such a micropattern-formed product integrated with the substrate: step A: a step of sandwiching and pressing the photocurable composition between the surface of the substrate and the patterned surface of the mold; step B: a step of curing the photocurable composition by light irradiation to obtain a micropattern-formed product comprising a cured product having the micropattern of the mold transferred on its surface; step C: a step of separating at least one of the mold and the substrate from the cured product to obtain a micropattern-formed product, a micropattern-formed product integrated with the substrate or a micropattern-formed product integrated with the mold; and step D: a step of separating the micropattern-formed product from the mold in a case where the micropattern-formed product integrated with the mold is obtained in the step C. ### Claim 8 (depends on 7) The process of claim 7, wherein the photocurable composition comprises an adamantyl group-containing acrylate monomer unit and a polyoxyalkylene acrylate monomer unit. ### Claim 9 (depends on 7) The method of claim 7, wherein the photocurable composition comprises a fluoroacrylate monomer unit. ### Claim 10 (depends on 7) The method of claim 7, wherein the photocurable composition comprises a fluoropolymer surfactant. ### Claim 11 (depends on 7) The method of claim 7, wherein the fluoropolymer surfactant consists of C atoms, F atoms, H atoms, and O atoms. ### Claim 12 A process for producing a micropattern-formed product, which comprises bringing a photocurable composition which comprises from 50 to 98 mass % of a monomer containing no fluorine atom and having a viscosity at 25° C. of from 0.1 to 100 mPa·s, from 0.1 to 45 mass % of a fluoromonomer, from more than 0.1 to 20 mass % of a fluorinated surfactant and/or a fluoropolymer and from 1 to 10 mass % of a photopolymerization initiator, and contains substantially no solvent, into contact with the micropatterned surface of a mold having a micropattern formed on the surface, separating the mold to produce a molded product of the photocurable composition having the micropattern of the mold transferred on its surface, and photo-curing the molded product of the photocurable composition. ### Claim 13 (depends on 12) The process of claim 12, wherein the photocurable composition comprises an adamantyl group-containing acrylate monomer unit and a polyoxyalkylene acrylate monomer unit. ### Claim 14 (depends on 12) The method of claim 12, wherein the photocurable composition comprises a fluoroacrylate monomer unit. ### Claim 15 (depends on 12) The method of claim 12, wherein the photocurable composition comprises a fluoropolymer surfactant. ### Claim 16 (depends on 12) The method of claim 12, wherein the fluoropolymer surfactant consists of C atoms, F atoms, H atoms, and O atoms. ### Claim 17 A process for producing a micropattern-formed product, which comprises carrying out the following steps E, F, G and as the case requires, step H, in this order with a photocurable composition comprising from 50 to 98 mass % of a monomer containing no fluorine atom and having a viscosity at 25° C. of from 0.1 to 100 mPa·s, from 0.1 to 45 mass % of a fluoromonomer, from more than 0.1 to 20 mass % of a fluorinated surfactant and/or a fluoropolymer and from 1 to 10 mass % of a photopolymerization initiator, and contains substantially no solvent, a substrate and a mold having a micropattern on its surface to obtain a micropattern-formed product having a micropattern on its surface or such a micropattern-formed product integrated with the substrate: step E: a step of pressing the photocurable composition between the surface of the substrate and the patterned surface of the mold; step F: a step of separating the mold from the photocurable composition to obtain a molded product of the photocurable composition having the micropattern of the mold transferred on its surface, integrated with the substrate; step G: a step of curing the molded product of the photocurable composition by light irradiation to obtain a micropattern-formed product comprising a cured product having the micropattern of the mold transferred on its surface, integrated with the substrate; and step H: a step of separating the micropattern-formed product from the substrate. ### Claim 18 (depends on 17) The process for producing a micropattern-formed product according to claim 17, wherein the micropattern of the mold is a micropattern having convex portions and concavo portions, and the average interval of the convex portions is from 1 nm to 500 μm. ### Claim 19 (depends on 17) The process of claim 17, wherein the photocurable composition comprises an adamantyl group-containing acrylate monomer unit and a polyoxyalkylene acrylate monomer unit. ### Claim 20 (depends on 17) The method of claim 17, wherein the photocurable composition comprises a fluoroacrylate monomer unit. ### Claim 21 (depends on 17) The method of claim 17, wherein the photocurable composition comprises a fluoropolymer surfactant. ### Claim 22 (depends on 17) The method of claim 17, wherein the fluoropolymer surfactant consists of C atoms, F atoms, H atoms, and O atoms.