JP2024516479A - 光硬化性組成物 - Google Patents

光硬化性組成物 Download PDF

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Publication number
JP2024516479A
JP2024516479A JP2023546542A JP2023546542A JP2024516479A JP 2024516479 A JP2024516479 A JP 2024516479A JP 2023546542 A JP2023546542 A JP 2023546542A JP 2023546542 A JP2023546542 A JP 2023546542A JP 2024516479 A JP2024516479 A JP 2024516479A
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Prior art keywords
photocurable composition
monomer
photocurable
substrate
layer
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Pending
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JP2023546542A
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English (en)
Japanese (ja)
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JP2024516479A5 (https=
JPWO2022231753A5 (https=
Inventor
フェン ワン,
ウェイジュン リウ,
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Canon Inc
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Canon Inc
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Publication of JP2024516479A publication Critical patent/JP2024516479A/ja
Publication of JP2024516479A5 publication Critical patent/JP2024516479A5/ja
Publication of JPWO2022231753A5 publication Critical patent/JPWO2022231753A5/ja
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81Unsaturated isocyanates or isothiocyanates
    • C08G18/8108Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71Monoisocyanates or monoisothiocyanates
    • C08G18/711Monoisocyanates or monoisothiocyanates containing oxygen in addition to isocyanate oxygen
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02Monomers containing only one unsaturated aliphatic radical
    • C08F212/04Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • C08F212/26Nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10Esters
    • C08F222/1006Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67Unsaturated compounds having active hydrogen
    • C08G18/671Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C08G18/673Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71Monoisocyanates or monoisothiocyanates
    • C08G18/712Monoisocyanates or monoisothiocyanates containing halogens
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71Monoisocyanates or monoisothiocyanates
    • C08G18/714Monoisocyanates or monoisothiocyanates containing nitrogen in addition to isocyanate or isothiocyanate nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81Unsaturated isocyanates or isothiocyanates
    • C08G18/8108Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5397Phosphine oxides
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0002Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20Exposure; Apparatus therefor
    • G03F7/2002Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2012Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)
  • Laminated Bodies (AREA)
JP2023546542A 2021-04-29 2022-03-30 光硬化性組成物 Pending JP2024516479A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US17/244,508 US11753497B2 (en) 2021-04-29 2021-04-29 Photocurable composition
US17/244,508 2021-04-29
PCT/US2022/022536 WO2022231753A1 (en) 2021-04-29 2022-03-30 Photocurable composition

Publications (3)

Publication Number Publication Date
JP2024516479A true JP2024516479A (ja) 2024-04-16
JP2024516479A5 JP2024516479A5 (https=) 2025-04-04
JPWO2022231753A5 JPWO2022231753A5 (https=) 2025-04-04

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Application Number Title Priority Date Filing Date
JP2023546542A Pending JP2024516479A (ja) 2021-04-29 2022-03-30 光硬化性組成物

Country Status (5)

Country Link
US (1) US11753497B2 (https=)
JP (1) JP2024516479A (https=)
KR (1) KR102899614B1 (https=)
TW (1) TWI833173B (https=)
WO (1) WO2022231753A1 (https=)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008138160A (ja) * 2006-11-08 2008-06-19 Sumitomo Osaka Cement Co Ltd ハードコート膜形成用塗料とハードコート膜及びハードコート膜付きプラスチック基材並びにポリビニル樹脂組成物の製造方法
JP2016002683A (ja) * 2014-06-16 2016-01-12 コニカミノルタ株式会社 3d造形物の製造方法、3d造形用光硬化性組成物および3d造形用インクセット
JP2019108535A (ja) * 2017-12-15 2019-07-04 ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC 熱成形可能なハードコート用途のためのuv−硬化アクリル樹脂組成物
JP2019183031A (ja) * 2018-04-12 2019-10-24 積水化学工業株式会社 接着剤樹脂組成物
JP2020532631A (ja) * 2017-09-22 2020-11-12 エルジー・ケム・リミテッド 偏光板保護層用の無溶剤型光硬化性樹脂組成物、これの硬化物を含む偏光板及び画像表示装置
JP2021050332A (ja) * 2019-09-23 2021-04-01 キヤノン株式会社 ナノファブリケーション用の硬化性組成物

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EP1275668B1 (en) * 2000-03-30 2011-05-11 Mitsubishi Chemical Corporation Photocurable composition, cured object, and process for producing the same
US7745505B2 (en) * 2004-12-29 2010-06-29 Henkel Ag & Co. Kgaa Photoinitiators and UV-crosslinkable acrylic polymers for pressure sensitive adhesives
US7759407B2 (en) 2005-07-22 2010-07-20 Molecular Imprints, Inc. Composition for adhering materials together
US8106134B2 (en) 2008-08-28 2012-01-31 Bridgestone Sports Co., Ltd. Golf ball and method of improving golf ball performance
US20100109195A1 (en) 2008-11-05 2010-05-06 Molecular Imprints, Inc. Release agent partition control in imprint lithography
US20120016050A1 (en) 2008-12-26 2012-01-19 Leon Joseph A Monoisocyanate-Acrylate Monomers and Products Ulitilizing the Same
KR20110007687A (ko) * 2009-07-17 2011-01-25 공주대학교 산학협력단 무용제 자외선 경화형 아크릴 점착제 조성물 및 그 제조방법
EP2484706A1 (de) 2011-02-03 2012-08-08 Sika Technology AG Haftvermittlerzusammensetzung
IN2014DN00290A (https=) 2011-06-17 2015-06-05 Materia Inc
WO2013019821A1 (en) 2011-08-01 2013-02-07 Sun Chemical Corporation High-stretch energy curable inks & method of use in heat transfer label applications
CN103946998B (zh) * 2011-11-18 2017-03-29 Lg化学株式会社 用于封装有机电子器件的光可固化压敏粘合剂膜,有机电子器件及其封装方法
JP2016183304A (ja) * 2015-03-26 2016-10-20 デクセリアルズ株式会社 アクリル系粘着テープの製造方法及びアクリル系粘着テープ
KR102047291B1 (ko) * 2016-09-23 2019-11-21 주식회사 엘지화학 접착제 조성물
CN108003802B (zh) * 2017-12-07 2021-03-30 烟台德邦科技股份有限公司 一种基于逐步聚合机理热致自愈合紫外光固化胶黏剂
US20200339828A1 (en) 2019-04-26 2020-10-29 Canon Kabushiki Kaisha Photocurable composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008138160A (ja) * 2006-11-08 2008-06-19 Sumitomo Osaka Cement Co Ltd ハードコート膜形成用塗料とハードコート膜及びハードコート膜付きプラスチック基材並びにポリビニル樹脂組成物の製造方法
JP2016002683A (ja) * 2014-06-16 2016-01-12 コニカミノルタ株式会社 3d造形物の製造方法、3d造形用光硬化性組成物および3d造形用インクセット
JP2020532631A (ja) * 2017-09-22 2020-11-12 エルジー・ケム・リミテッド 偏光板保護層用の無溶剤型光硬化性樹脂組成物、これの硬化物を含む偏光板及び画像表示装置
JP2019108535A (ja) * 2017-12-15 2019-07-04 ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC 熱成形可能なハードコート用途のためのuv−硬化アクリル樹脂組成物
JP2019183031A (ja) * 2018-04-12 2019-10-24 積水化学工業株式会社 接着剤樹脂組成物
JP2021050332A (ja) * 2019-09-23 2021-04-01 キヤノン株式会社 ナノファブリケーション用の硬化性組成物

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Publication number Publication date
KR20230173705A (ko) 2023-12-27
TWI833173B (zh) 2024-02-21
US20220363807A1 (en) 2022-11-17
TW202309658A (zh) 2023-03-01
US11753497B2 (en) 2023-09-12
KR102899614B1 (ko) 2025-12-15
WO2022231753A1 (en) 2022-11-03

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