WO2011013663A1 - Composition adhésive durcissable par rayonnement d'énergie actinique destinée à un film ou feuillet plastique - Google Patents

Composition adhésive durcissable par rayonnement d'énergie actinique destinée à un film ou feuillet plastique Download PDF

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Publication number
WO2011013663A1
WO2011013663A1 PCT/JP2010/062619 JP2010062619W WO2011013663A1 WO 2011013663 A1 WO2011013663 A1 WO 2011013663A1 JP 2010062619 W JP2010062619 W JP 2010062619W WO 2011013663 A1 WO2011013663 A1 WO 2011013663A1
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WO
WIPO (PCT)
Prior art keywords
component
meth
acrylate
curable
plastic film
Prior art date
Application number
PCT/JP2010/062619
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English (en)
Japanese (ja)
Inventor
一樹 大房
Original Assignee
東亞合成株式会社
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 東亞合成株式会社 filed Critical 東亞合成株式会社
Priority to KR1020127005367A priority Critical patent/KR101713003B1/ko
Priority to JP2011524791A priority patent/JP5633514B2/ja
Priority to CN201080033913.3A priority patent/CN102471642B/zh
Publication of WO2011013663A1 publication Critical patent/WO2011013663A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • C08J5/128—Adhesives without diluent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2400/00—Characterised by the use of unspecified polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Definitions

  • Patent Document 1 a composition containing a radical polymerizable compound containing a polar group such as a hydroxyl group or a carboxyl group and a radical polymerizable compound not containing a polar group (Patent Document 1) is known. ing. However, the composition has a large shrinkage during curing, and depending on the type of adherend, it has been difficult to obtain sufficient peel strength due to the generation of stress at the interface. In order to solve this problem, a composition containing urethane (meth) acrylate having a large molecular weight has been studied (for example, Patent Document 2). However, since the viscosity increases, the composition has a problem that thin film coating cannot be performed depending on the coating apparatus.
  • composition disclosed in Patent Document 5 contains a (meth) acrylate compound having an isocyanuric ring skeleton as an essential component, but according to the study of the present inventors, the composition having two or more (meth) acryloyl groups.
  • a large amount of (meth) acrylate is contained in the composition, the shrinkage at the time of curing is not so small that stress generation at the interface cannot be suppressed. For this reason, it is difficult to obtain sufficient peel strength depending on the substrate. It turned out to be.
  • the aliphatic epoxy compound examples include diglycidyl ethers of alkylene glycols such as ethylene glycol, propylene glycol, 1,4-butanediol and 1,6-hexanediol; polyalkylene glycols such as diglycidyl ethers of polyethylene glycol and polypropylene glycol Diglycidyl ether of dipentyl glycol, dibromoneopentyl glycol and its alkylene oxide adducts; dimethylidyl ether of trimethylolethane, trimethylolpropane, glycerin and its alkylene oxide adducts, and pentaerythritol and Polyglycidides of polyhydric alcohols such as di-, tri- or tetraglycidyl ethers of the alkylene oxide adducts Ether; hydrogenated bisphenol A and di- or polyglycidyl ethers of alkylene oxide adducts; t
  • the component (B) is a compound having one ethylenically unsaturated group in the molecule, and examples thereof include a compound having a (meth) acryloyl group, a vinyl compound, and an allyl compound.
  • diazonium salts examples include benzenediazonium hexafluoroantimonate, Examples thereof include benzenediazonium hexafluorophosphate.
  • component (C) As a component, an above described compound may be used independently, or 2 or more types may be used.
  • the proportion of component (C) is 0.1 to 20% by weight, preferably 1 to 10% by weight, more preferably 2 to 7% by weight, based on the total amount of curable components.
  • the proportion of the component (C) is 0.1% by weight or more, the active energy ray curability of the composition can be made sufficient and the adhesiveness can be made excellent, while it is made 20% by weight or less.
  • the internal curability of the adhesive layer can be improved and the adhesiveness can be improved.
  • the component (E) is a compound having two or more ethylenically unsaturated groups in the molecule, and examples thereof include a compound having a (meth) acryloyl group, a vinyl compound, and an allyl compound.
  • aliphatic epoxy resin examples include diglycidyl ethers of alkylene glycols such as ethylene glycol, propylene glycol, 1,4-butanediol and 1,6-hexanediol; diglycidyl ethers of polyethylene glycol and polypropylene glycol, etc.
  • a polarizer has a function of selectively transmitting linearly polarized light in one direction from natural light.
  • polarizers include iodine polarizers in which iodine is adsorbed and oriented on a polyvinyl alcohol film, dichroic dyes in which dichroic dye is adsorbed and oriented on a polyvinyl alcohol film, and (lyotropic) liquid crystal Examples thereof include a coating type polarizer coated with a dye in a state, oriented and fixed.
  • These iodine-based polarizers, dye-based polarizers, and coating-type polarizers have the function of selectively transmitting one direction of linearly polarized light from natural light and absorbing the other direction of linearly polarized light. It is called a type polarizer.
  • the manufacturing method of a polarizing plate or a polarizing plate with a retardation film will be described using the composition of the present invention.
  • Examples of the production method include a method including the following steps [1] to [3].
  • [1] A process of applying the composition of the present invention to an adherend (base material) selected from a polarizer, a polarizing plate, a protective film, a protective film, a retardation film, and a retardation film to be an adherend.
  • adherend (base material) coated with the composition another adherend selected from a polarizer, a polarizing plate, a protective film, a protective film, a retardation film, and a retardation film is attached.
  • ACMO acryloylmorpholine, manufactured by Kojin Co., Ltd.
  • PEA phenoxyethyl acrylate, Kyoeisha Chemical Co., Ltd. light acrylate
  • PO-A M-145 2- (1,2-cyclohex-1-enedicarboximide) ethyl acrylate, Aronix M-145 manufactured by Toagosei Co., Ltd.
  • HPA 2-hydroxypropyl acrylate, Kyoeisha Chemical Co., Ltd. light ester HOP-A ⁇ HBA: 2-hydroxybutyl acrylate, Kyoeisha Chemical Co., Ltd.

Abstract

La présente invention concerne une composition adhésive durcissable par rayonnement d'énergie actinique destinée à des films plastiques ou équivalents et ayant une faible viscosité et une excellente durcissabilité, une excellente adhésion sur divers films plastiques ou équivalents, en particulier, des films plastiques hydrophobes ou équivalents, et une performance suffisante même dans des applications où une extrême durabilité est nécessaire. La composition adhésive durcissable par rayonnement d'énergie actinique, destinée à être utilisée dans des films ou feuillets plastiques, est une composition comprenant des composants durcissables et un initiateur de la polymérisation, les composants durcissables comprenant le composant (A), qui est un composé ayant deux ou plusieurs groupes époxy (10 à 80 % en poids des composants durcissables), et le composant (B), qui est un composé ayant un groupe insaturé éthylénique (20 à 90 % en poids), et ne contient pratiquement pas de composé polymérisable par voie cationique contenant un groupe (meth)acryloyle, et l'initiateur de la polymérisation comprend le composant (C), qui est un initiateur de la polymérisation cationique (0,1 à 20 % en poids), et le composant (D), qui est un initiateur de la polymérisation radicalaire (0,1 à 20 % en poids). L'invention concerne également un procédé de production de la composition adhésive.
PCT/JP2010/062619 2009-07-28 2010-07-27 Composition adhésive durcissable par rayonnement d'énergie actinique destinée à un film ou feuillet plastique WO2011013663A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020127005367A KR101713003B1 (ko) 2009-07-28 2010-07-27 플라스틱제 필름 또는 시트용 활성 에너지선 경화형 접착제 조성물
JP2011524791A JP5633514B2 (ja) 2009-07-28 2010-07-27 プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
CN201080033913.3A CN102471642B (zh) 2009-07-28 2010-07-27 塑料制膜或片用活性能量射线固化型胶粘剂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009175453 2009-07-28
JP2009-175453 2009-07-28

Publications (1)

Publication Number Publication Date
WO2011013663A1 true WO2011013663A1 (fr) 2011-02-03

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PCT/JP2010/062619 WO2011013663A1 (fr) 2009-07-28 2010-07-27 Composition adhésive durcissable par rayonnement d'énergie actinique destinée à un film ou feuillet plastique

Country Status (5)

Country Link
JP (2) JP5633514B2 (fr)
KR (1) KR101713003B1 (fr)
CN (1) CN102471642B (fr)
TW (1) TWI493005B (fr)
WO (1) WO2011013663A1 (fr)

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JP2012062471A (ja) * 2010-09-20 2012-03-29 Lg Chem Ltd 偏光板用接着剤及びこれを含む偏光板
WO2012133163A1 (fr) * 2011-03-29 2012-10-04 住友化学株式会社 Plaque de polarisation et élément optique stratifié
WO2012173054A1 (fr) * 2011-06-11 2012-12-20 東亞合成株式会社 Composition adhésive durcissable par un rayonnement d'énergie active pour film ou feuille de plastique
WO2012173055A1 (fr) * 2011-06-11 2012-12-20 東亞合成株式会社 Composition adhésive durcissable par un rayonnement d'énergie active pour film ou feuille de plastique
JP2013035968A (ja) * 2011-08-09 2013-02-21 Toyo Ink Sc Holdings Co Ltd 偏光板形成用光硬化性接着剤および偏光板
JP2013092546A (ja) * 2011-10-24 2013-05-16 Sumitomo Chemical Co Ltd 偏光板及びそれを用いた積層光学部材
JP2013142863A (ja) * 2012-01-12 2013-07-22 Sumitomo Chemical Co Ltd 光硬化性接着剤、それを用いた偏光板および積層光学部材
JP2013181096A (ja) * 2012-03-01 2013-09-12 Toagosei Co Ltd フィルム又はシート用活性エネルギー線硬化型接着剤組成物
JP2013185133A (ja) * 2012-03-09 2013-09-19 Cheil Industries Inc 偏光板用接着剤
WO2013146556A1 (fr) * 2012-03-30 2013-10-03 住友化学株式会社 Plaque polarisante
JP2013218168A (ja) * 2012-04-10 2013-10-24 Sekisui Chem Co Ltd 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子
JP2013227489A (ja) * 2012-03-29 2013-11-07 Toyo Ink Sc Holdings Co Ltd 光重合性オキシラン系樹脂組成物、光重合性接着剤、及び光学フィルム積層体
JP2013543524A (ja) * 2010-09-20 2013-12-05 エルジー・ケム・リミテッド 偏光板用接着剤及びこれを含む偏光板
JP2013254072A (ja) * 2012-06-06 2013-12-19 Nitto Denko Corp 偏光板、光学フィルムおよび画像表示装置
JP2014500984A (ja) * 2011-10-14 2014-01-16 エルジー・ケム・リミテッド 偏光板用接着剤及びこれを含む偏光板
JP2014037477A (ja) * 2012-08-15 2014-02-27 Cheil Industries Inc 偏光板用接着剤
WO2014058042A1 (fr) * 2012-10-11 2014-04-17 東亞合成株式会社 Composition d'adhésif photodurcissable, polariseur et processus de production de celui-ci, élément optique et dispositif d'affichage à cristaux liquides
CN103764782A (zh) * 2011-08-29 2014-04-30 日东电工株式会社 光学用粘合粘接剂组合物、光学用粘合粘接剂层、光学构件、偏光板、和图像显示装置
WO2014178239A1 (fr) * 2013-05-02 2014-11-06 Dic株式会社 Composition adhésive et lame polarisante
WO2015194654A1 (fr) * 2014-06-20 2015-12-23 東亞合成株式会社 Composition adhésive durcissable par un faisceau d'énergie d'activation pour film ou feuille plastique
US9523792B2 (en) 2011-10-14 2016-12-20 Lg Chem, Ltd. Polarizer having protection films in two sides and optical device comprising the same
WO2017104165A1 (fr) * 2015-12-18 2017-06-22 古河電気工業株式会社 Composition adhésive, procédé de liaison de parties adhérées l'utilisant et procédé de fabrication de stratifié

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JP2012062471A (ja) * 2010-09-20 2012-03-29 Lg Chem Ltd 偏光板用接着剤及びこれを含む偏光板
US9250358B2 (en) 2010-09-20 2016-02-02 Lg Chem, Ltd. Adhesive for polarizing plate, and polarizing plate comprising the same
JP2013543524A (ja) * 2010-09-20 2013-12-05 エルジー・ケム・リミテッド 偏光板用接着剤及びこれを含む偏光板
WO2012133163A1 (fr) * 2011-03-29 2012-10-04 住友化学株式会社 Plaque de polarisation et élément optique stratifié
JP2012208246A (ja) * 2011-03-29 2012-10-25 Sumitomo Chemical Co Ltd 偏光板および積層光学部材
KR101989420B1 (ko) * 2011-06-11 2019-06-14 도아고세이가부시키가이샤 플라스틱제 필름 또는 시트용 활성 에너지선 경화형 접착제 조성물
WO2012173055A1 (fr) * 2011-06-11 2012-12-20 東亞合成株式会社 Composition adhésive durcissable par un rayonnement d'énergie active pour film ou feuille de plastique
JPWO2012173055A1 (ja) * 2011-06-11 2015-02-23 東亞合成株式会社 プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
KR20140031244A (ko) * 2011-06-11 2014-03-12 도아고세이가부시키가이샤 플라스틱제 필름 또는 시트용 활성 에너지선 경화형 접착제 조성물
CN103597049A (zh) * 2011-06-11 2014-02-19 东亚合成株式会社 塑料制膜或片用活性能量射线固化型粘合剂组合物
WO2012173054A1 (fr) * 2011-06-11 2012-12-20 東亞合成株式会社 Composition adhésive durcissable par un rayonnement d'énergie active pour film ou feuille de plastique
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JP5633514B2 (ja) 2014-12-03
TW201109405A (en) 2011-03-16
KR20120039053A (ko) 2012-04-24
CN102471642A (zh) 2012-05-23
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CN102471642B (zh) 2014-09-17
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