WO2020209264A1 - Composition de résine durcissable par rayon actinique, objet durci, stratifié, et article - Google Patents

Composition de résine durcissable par rayon actinique, objet durci, stratifié, et article Download PDF

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Publication number
WO2020209264A1
WO2020209264A1 PCT/JP2020/015722 JP2020015722W WO2020209264A1 WO 2020209264 A1 WO2020209264 A1 WO 2020209264A1 JP 2020015722 W JP2020015722 W JP 2020015722W WO 2020209264 A1 WO2020209264 A1 WO 2020209264A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
active energy
curable resin
resin composition
Prior art date
Application number
PCT/JP2020/015722
Other languages
English (en)
Japanese (ja)
Inventor
直人 井上
伊藤 正広
Original Assignee
Dic株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to KR1020217029985A priority Critical patent/KR102564260B1/ko
Priority to JP2021513649A priority patent/JP7131695B2/ja
Priority to CN202080027289.XA priority patent/CN113661064B/zh
Publication of WO2020209264A1 publication Critical patent/WO2020209264A1/fr

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Classifications

    • 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
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • C08F290/067Polyurethanes; Polyureas
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • B32B27/30Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • 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
    • 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
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • 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
    • C08F222/104Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(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
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18Manufacture of films or sheets
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/046Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D4/00Coating 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
    • C09D4/06Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Definitions

  • the active energy ray-curable resin composition of the present invention uses the urethane (meth) acrylate resin (A), the (meth) acrylate compound (B), and the (meth) acrylate compound (C) as essential components. Any other active energy ray-curable resin component may be used in combination as long as the effect of the present invention is not impaired.
  • Examples of commercially available products of the other photopolymerization initiator include “Omnirad-1173”, “Omnirad-184", “Omnirad-127”, “Omnirad-2959”, “Omnirad-369”, and “Omnirad-379".
  • the organic beads include, for example, polymethyl methacrylate beads, polycarbonate beads, polystyrene beads, polyacrylic styrene beads, silicone beads, glass beads, acrylic beads, benzoguanamine resin beads, melamine resin beads, and polyolefin resin beads.
  • examples thereof include polyester resin beads, polyamide resin beads, polyimide resin beads, polyfluoroethylene resin beads, and polyethylene resin beads. Each of these may be used alone, or two or more types may be used in combination.
  • the average particle size of these organic beads is preferably in the range of 1 to 10 ⁇ m.
  • Quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe and the like can be mentioned.
  • the group I-III-VI semiconductor compound for example, CuInS 2, CuInSe 2, CuInTe 2, CuGaS 2, CuGaSe 2, CuGaSe 2, AgInS 2, AgInSe 2, AgInTe 2, AgGaSe 2, AgGaTe 2 etc.
  • Examples of the Group IV element or a compound containing the same include C, Si, Ge, SiC, SiGe and the like.
  • the quantum dots may be composed of a single semiconductor compound, or may have a core-shell structure composed of a plurality of semiconductor compounds. Further, the surface thereof may be modified with an organic compound.
  • the sheet bonding method is a resin layer in which a base sheet of a protective layer forming sheet prepared in advance and a molded product are bonded to each other and then heat-cured by heating to form a B-stage.
  • H6XDI indicates hydrogenated xylylene diisocyanate.
  • the obtained active energy ray-curable resin composition (1) was applied on an acrylic film having a thickness of 40 ⁇ m with a bar coater, and dried at 90 ° C. for 1 minute.
  • ultraviolet rays were irradiated at 50 mJ / cm 2 with an 80 W high-pressure mercury lamp to obtain a laminate (L1) having a cured coating film having a film thickness of 5 ⁇ m on an acrylic film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une composition de résine durcissable par rayon actinique qui comprend une résine uréthane (méth)acrylate (A), un composé (méth)acrylate (B) possédant au moins un mais au plus deux groupes (méth)acryloyle dans chaque molécule, et un composé (méth)acrylate (C) possédant au moins trois groupes (méth)acryloyle dans chaque molécule. Plus précisément, l'invention fournit une composition de résine durcissable par rayon actinique qui est caractéristique en ce que la masse moléculaire moyenne en poids de ladite résine uréthane (méth)acrylate (A) est comprise dans une plage de 1500 à 30000, et la teneur en composé (méth)acrylate (B) est comprise dans une plage de 10 à 50% en masse pour la masse totale de résine uréthane (méth)acrylate (A), composé (méth)acrylate (B) et composé (méth)acrylate (C). Cette composition de résine durcissable par rayon actinique permet de former un objet durci excellent en termes de dureté, résistance à l'abrasion et adhésion à un substrat.
PCT/JP2020/015722 2019-04-10 2020-04-07 Composition de résine durcissable par rayon actinique, objet durci, stratifié, et article WO2020209264A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020217029985A KR102564260B1 (ko) 2019-04-10 2020-04-07 활성 에너지선 경화성 수지 조성물, 경화물, 적층체 및 물품
JP2021513649A JP7131695B2 (ja) 2019-04-10 2020-04-07 活性エネルギー線硬化性樹脂組成物、硬化物、積層体及び物品
CN202080027289.XA CN113661064B (zh) 2019-04-10 2020-04-07 活性能量射线固化性树脂组合物、固化物、层叠体及物品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019074864 2019-04-10
JP2019-074864 2019-04-10

Publications (1)

Publication Number Publication Date
WO2020209264A1 true WO2020209264A1 (fr) 2020-10-15

Family

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Family Applications (1)

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PCT/JP2020/015722 WO2020209264A1 (fr) 2019-04-10 2020-04-07 Composition de résine durcissable par rayon actinique, objet durci, stratifié, et article

Country Status (4)

Country Link
JP (1) JP7131695B2 (fr)
KR (1) KR102564260B1 (fr)
CN (1) CN113661064B (fr)
WO (1) WO2020209264A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114656767A (zh) * 2020-12-22 2022-06-24 Dic株式会社 活性能量射线固化性树脂组合物、固化物及物品
WO2023042922A1 (fr) * 2021-09-17 2023-03-23 三菱ケミカル株式会社 Procédé de production de film multicouche, procédé de fabrication de panneau de mélamine décoratif, film multicouche, film protecteur pour panneau de mélamine décoratif et panneau de mélamine décoratif

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JP2011020381A (ja) * 2009-07-16 2011-02-03 Fujikura Kasei Co Ltd 耐紫外線プラスチック成形体
WO2014033932A1 (fr) * 2012-08-31 2014-03-06 株式会社ダイセル Feuille optique
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114656767A (zh) * 2020-12-22 2022-06-24 Dic株式会社 活性能量射线固化性树脂组合物、固化物及物品
WO2023042922A1 (fr) * 2021-09-17 2023-03-23 三菱ケミカル株式会社 Procédé de production de film multicouche, procédé de fabrication de panneau de mélamine décoratif, film multicouche, film protecteur pour panneau de mélamine décoratif et panneau de mélamine décoratif

Also Published As

Publication number Publication date
KR20210127750A (ko) 2021-10-22
JPWO2020209264A1 (ja) 2021-10-07
CN113661064B (zh) 2023-12-26
JP7131695B2 (ja) 2022-09-06
CN113661064A (zh) 2021-11-16
TW202100600A (zh) 2021-01-01
KR102564260B1 (ko) 2023-08-07

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