WO2017110951A1 - Composition durcissable, procédé pour la durcir, et produit durci ainsi obtenu - Google Patents

Composition durcissable, procédé pour la durcir, et produit durci ainsi obtenu Download PDF

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Publication number
WO2017110951A1
WO2017110951A1 PCT/JP2016/088250 JP2016088250W WO2017110951A1 WO 2017110951 A1 WO2017110951 A1 WO 2017110951A1 JP 2016088250 W JP2016088250 W JP 2016088250W WO 2017110951 A1 WO2017110951 A1 WO 2017110951A1
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curable composition
compound
epoxy compound
oxetane
cationic
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PCT/JP2016/088250
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English (en)
Japanese (ja)
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一輝 長坂
泰延 大野
和彦 松土
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株式会社Adeka
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    • 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
    • C08G59/20—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 epoxy compounds used

Definitions

  • the present invention relates to a curable composition, a method for curing the same, and a cured product and an adhesive obtained thereby.
  • the curable composition is excellent in adhesion and has a low viscosity, useful for optical films, and the cured product.
  • the present invention relates to a method and a cured product obtained thereby.
  • a curable composition made of epoxy resin has excellent adhesion to various substrates, and a cured product obtained by curing an epoxy resin with a curing agent has heat resistance, chemical resistance, electrical properties, and mechanical properties. Etc. are relatively excellent, and are used in the fields of inks, paints, various coating agents, adhesives, optical members and the like.
  • Patent Document 1 proposes a cationic polymerizable adhesive containing an oxetane compound, an aromatic glycidyl ether, and a cationic polymerization initiator.
  • the photocurable composition containing the photocurable component containing the epoxy compound which has an alicyclic epoxy group, a silane coupling agent, and a photocationic polymerization initiator is proposed as an adhesive agent for polarizing plates.
  • Patent Document 3 proposes a cationic adhesive containing an epoxy compound, an oxetane compound and a photocationic polymerization initiator as a cationic adhesive for polarizing plates.
  • Patent Document 4 proposes a cationically polymerizable composition containing an aromatic epoxy compound and an aliphatic epoxy compound or an alicyclic epoxy compound as a cationically polymerizable organic substance.
  • JP 2010-229392 A JP 2013-210445A Special table 2014-505274 gazette International Publication No. 2015/005211
  • an object of the present invention is to provide a curable composition having excellent adhesiveness and low viscosity, useful for optical films, a curing method thereof, and a cured product obtained thereby.
  • the curable composition of the present invention is a curable composition containing 100 parts by weight of the cationic curable component (A) and 0.1 to 15 parts by weight of the cationic polymerization initiator (B),
  • the cationic curable component (A) is characterized by comprising an alicyclic epoxy compound (A1), an aliphatic epoxy compound (A2), and an oxetane compound (A3) as essential components.
  • the curable composition of the present invention preferably further contains an aromatic epoxy compound (A3) as the cationic curable component (A).
  • the curable composition of the present invention further contains 0.1 to 15 parts by mass of a silane coupling agent having an epoxy group (excluding the cationic curable component (A)) (C). Is preferred.
  • the alicyclic epoxy compound (A1) is preferably 1 to 30% by mass in 100% by mass of the cationic curable component (A).
  • the alicyclic epoxy compound (A1) is 3 ′, 4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 7-oxabicyclo [4.
  • the oxetane compound (A3) is 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl) oxetane, xylylene bisoxetane, It is preferably at least one selected from the group of 3-ethyl-3- (3-ethyl-3-oxetanylmethyloxymethyl) oxetane.
  • the curing method of the curable composition of the present invention is characterized in that the cured product of the present invention is cured by irradiation with active energy rays or heating.
  • the cured product of the present invention is characterized by comprising the curable composition of the present invention.
  • the present invention it is possible to provide a curable composition having excellent adhesiveness and low viscosity, useful for optical films, a curing method thereof, and a cured product obtained thereby.
  • the curable composition of the present invention contains 100 parts by weight of the cationic curable component (A) and 0.1 to 15 parts by weight of the cationic polymerization initiator (B) (hereinafter referred to as “component (A)” and “ (B) component "). Preferably, it further contains 0.1 to 15 parts by mass of a silane coupling agent having an epoxy group (excluding the cationic curable component (A)) (C).
  • the component (A) has the alicyclic epoxy compound (A1), the aliphatic epoxy compound (A2) and the oxetane compound (A3) as essential components, and preferably an aromatic epoxy. Contains compound (A4).
  • components (A) to (C) will be described in detail.
  • the component (A) used in the cured product of the present invention is a compound that is polymerized or cross-linked by a cationic polymerization initiator activated by energy ray irradiation or heating, and an alicyclic epoxy compound (A1),
  • the aliphatic epoxy compound (A2) and the oxetane compound (A3) are essential components, and preferably contains an aromatic epoxy compound (A4).
  • alicyclic epoxy compound (A1) can be obtained by epoxidizing a polyglycidyl etherified product of a polyhydric alcohol having at least one alicyclic ring or a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent.
  • examples include cyclohexene oxide and cyclopentene oxide-containing compounds.
  • hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate or 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexane Carboxylate is preferable from the viewpoint of improving adhesion.
  • alicyclic epoxy compound (A1) commercially available products can be used.
  • Celoxide 2021P Celoxide 2081, Celoxide 2000, Celoxide 3000, Cyclomer M100 (manufactured by Daicel); CYRACURE UVR-6128 (Dow) ⁇ Chemical Co.).
  • the viscosity of the alicyclic epoxy compound (A1) is 1 to 60% by mass, particularly 5 to 50% by mass with respect to 100% by mass of the component (A). It is preferable because coatability and reactivity are improved.
  • the aliphatic epoxy compound (A2) refers to an epoxy compound that is not classified into the alicyclic epoxy compound (A1) or the aromatic epoxy compound (A4) described later.
  • Specific examples of the aliphatic epoxy compound include aliphatic alcohols.
  • Monofunctional epoxy compounds such as glycidyl etherified products, glycidyl esters of alkylcarboxylic acids, polyglycidyl etherified products of aliphatic polyhydric alcohols or alkylene oxide adducts thereof, and polyfunctional epoxies such as polyglycidyl esters of aliphatic long-chain polybasic acids Compounds.
  • Representative compounds include allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexane.
  • Glycidyl ether of alcohol and aliphatic such as propylene glycol, trimethylolpropane, glycerin
  • Polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to polyhydric alcohols include diglycidyl esters of aliphatic long-chain dibasic acids. Further examples include monoglycidyl ethers of higher aliphatic alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxy stearate, butyl epoxy stearate, epoxidized soybean oil, epoxidized polybutadiene, and the like.
  • a glycidyl etherified product of an aliphatic alcohol or a polyglycidyl etherified product of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof is preferable because viscosity, coating property, and reactivity are improved, and further ethylene glycol diglycidyl.
  • Ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether or 1,6-hexanediol diglycidyl ether is preferred.
  • aliphatic epoxy compound (A2) commercially available products can be used.
  • the aliphatic epoxy compound (A2) is 5 to 40% by mass, particularly 20 to 30% by mass with respect to 100% by mass of the component (A). This is preferable because the property and reactivity are improved.
  • Examples of the oxetane compound (A3) include 3,7-bis (3-oxetanyl) -5-oxa-nonane, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, 1,2-bis.
  • oxetane compound (A3) commercially available products having a cationic polymerizable monomer as a main component can be used.
  • 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether manufactured by Maruzen Petrochemical Co., Ltd.
  • Aron Oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212 manufactured by Toagosei Co., Ltd.
  • etanacol OXBP manufactured by Ube Industries
  • the oxetane compound (A3) is 10 to 40% by mass, particularly 20 to 30% by mass with respect to 100% by mass of the component (A). This is preferable because the reactivity is improved.
  • the aromatic epoxy compound (A4) refers to an epoxy compound having a plurality of epoxy groups and containing an aromatic ring.
  • the polyfunctional aromatic epoxy compound include at least one aromatic compound such as phenol, cresol, and butylphenol.
  • Glycidyl ethers of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, catechol; alcoholic hydroxyl groups such as benzenedimethanol, benzenediethanol, and benzenedibutanol
  • polyglycidyl ethers of phenols polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups
  • polyglycidyl ethers of polyphenols polyglycidyl esters of benzoic acids
  • polybasic acid polys It is preferable to contain at least one selected from the group of glycidyl esters from the viewpoint of reducing the viscosity of the curable composition.
  • aromatic epoxy compound a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol E type epoxy compound, or a phenol novolac type epoxy compound is preferable because of excellent curability.
  • aromatic epoxy compound (A4) commercially available products can be used.
  • the aromatic epoxy compound (A4) is 20 to 60% by mass, particularly 30 to 50% by mass, with respect to 100% by mass of the component (A), to improve the curability. It is preferable from the viewpoint.
  • a vinyl ether compound (A5) may be further added as the cationic curable component (A).
  • the vinyl ether compound (A5) include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, Examples include 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether, and the like.
  • the alicyclic epoxy compound (A1), the aliphatic epoxy compound (A2), the oxetane compound (A3), the aromatic epoxy compound (A4), and the vinyl ether compound ( The proportion of A5) used is 1 to 30% by mass of the alicyclic epoxy compound (A1), 5 to 40% by mass of the aliphatic epoxy compound (A2), 100% by mass of the component (A), and the oxetane compound (A3). 10 to 40% by mass, 20 to 60% by mass of the aromatic epoxy compound (A4), and 1 to 15 parts by mass of the vinyl ether compound (A5) improve the viscosity, coating property, reactivity and curability. Therefore, it is preferable.
  • the component (B) used in the curable composition of the present invention may be any compound as long as it can release a substance that initiates cationic polymerization by energy ray irradiation or heating, but preferably , A double salt that is an onium salt that releases a Lewis acid upon irradiation with energy rays, or a derivative thereof.
  • a double salt that is an onium salt that releases a Lewis acid upon irradiation with energy rays or a derivative thereof.
  • Representative examples of such compounds include the following general formula: [A] r + [B] r- And cation and anion salts represented by the formula:
  • the cation [A] r + is preferably onium, and the structure thereof is, for example, the following general formula [(R 2 ) a Q] r + Can be expressed as
  • R 2 is an organic group having 1 to 60 carbon atoms and any number of atoms other than carbon atoms.
  • a is an integer of 1 to 5.
  • the a R 2 s are independent and may be the same or different.
  • the anion [B] r- is preferably a halide complex, and the structure thereof is, for example, the following general formula: [LY b ] r- Can be expressed as
  • L is a metal or metalloid which is a central atom of a halide complex
  • B P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc , V, Cr, Mn, Co, and the like.
  • Y is a halogen atom.
  • b is an integer of 3 to 7.
  • anion [LY b ] r- of the general formula include tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, tetrafluoroborate (BF 4 ) ⁇ , hexa Examples thereof include fluorophosphate (PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarsenate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ and the like.
  • the anion [B] r- is represented by the following general formula: [LY b-1 (OH)] r-
  • the thing of the structure represented by can also be used preferably. L, Y, and b are the same as described above.
  • Other anions that can be used include perchlorate ion (ClO 4 ) ⁇ , trifluoromethylsulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , and toluenesulfonate anion.
  • Trinitrobenzenesulfonate anion camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctane sulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
  • onium salts it is particularly preferable to use the following aromatic onium salts (i) to (iii).
  • aromatic onium salts (i) to (iii) In the curable composition of the present invention, one of these may be used alone, or two or more may be used in combination.
  • aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate, etc.
  • Diaryls such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, tricumyliodonium tetrakis (pentafluorophenyl) borate Iodonium salt
  • sulfonium salts such as sulfonium cations represented by the following group I or group II and hexafluoroantimony ions, hexafluorophosphate ions, tetrakis (pentafluorophenyl) borate ions, etc.
  • aromatic iodonium salts aromatic sulfonium salts, and iron-arene complexes are preferably used from the viewpoints of practical use and improvement of photosensitivity.
  • the use ratio of the component (B) relative to the component (A) is not particularly limited, and may be used at a generally normal use ratio within a range not impairing the object of the present invention.
  • the component (B) can be 0.1 to 15 parts by mass, preferably 1 to 10 parts by mass. If the amount is too small, curing tends to be insufficient, and if the amount is too large, various physical properties such as the water absorption rate and the strength of the cured product may be adversely affected.
  • ⁇ Silane coupling agent having epoxy group (C)> (C) component used for this invention is a silane coupling agent which has an epoxy group, However, What corresponds to (A) component is not contained.
  • an epoxy functional alkoxysilane can be used, for example, ⁇ -glycidyloxypropyltrimethoxysilane, ⁇ -glycidyloxypropyltriethoxysilane, ⁇ -glycidyloxypropylmethyldimethoxysilane, ⁇ -glycidyl. Examples thereof include oxypropylmethyldiethoxysilane and ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane.
  • component (C) commercially available products may be used.
  • D2632, G0261, G0210, T2675 manufactured by Tokyo Chemical Industry Co., Ltd.
  • KBM-303, KBM-402, KBM-403, KBE-402, KBE-403 Shin-Etsu Silicone Co., Ltd.
  • component (C) used is not particularly limited.
  • component (C) is 0.1 to 15 parts by weight, preferably 1 to 10 parts by weight, relative to 100 parts by weight of component (A). it can.
  • a sensitizer and / or a sensitization aid can be used in the curable composition of the present invention as necessary.
  • the sensitizer is a compound that exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength indicated by the cationic polymerization initiator (B) and promotes the polymerization initiation reaction by the cationic polymerization initiator (B).
  • the sensitization aid is a compound that further promotes the action of the sensitizer.
  • Sensitizers and sensitizers include anthracene compounds and naphthalene compounds.
  • anthracene compound examples include those represented by the following formula (1).
  • R 1 and R 2 each independently represents an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Represents an alkyl group.
  • anthracene compound represented by the above formula (1) include the following compounds.
  • naphthalene compound examples include those represented by the following formula (2).
  • R 4 and R 5 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • naphthalene compound represented by the above formula (2) include the following compounds.
  • 4-methoxy-1-naphthol 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyloxy-1-naphthol, 1,4-dimethoxynaphthalene, 1- Ethoxy-4-methoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-dipropoxynaphthalene, 1,4-dibutoxynaphthalene and the like.
  • the use ratio of the sensitizer and the sensitization aid to the component (A) is not particularly limited, and may be used at a generally normal use ratio within a range not impairing the object of the present invention.
  • the curable composition of the present invention can also improve the properties of the cured product by using a thermoplastic organic polymer as necessary.
  • the thermoplastic organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, and (meth) acrylic acid-methyl.
  • examples thereof include a methacrylate copolymer, a glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymer, polyvinyl butyral, cellulose ester, polyacrylamide, and saturated polyester.
  • a solvent that can dissolve or disperse the components (A), (B), and (C) that are usually used without any particular limitation can be used.
  • methyl ethyl ketone, methyl Ketones such as amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol Ether solvents such as monomethyl ether and dipropylene glycol dimethyl ether; esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate
  • curable composition of the present invention other monomers, other energy ray-sensitive polymerization initiators, inorganic fillers, organic fillers, pigments, dyes and the like are colored as necessary unless the effects of the present invention are impaired.
  • resin additives such as a flow regulator and an adhesion promoter can be added.
  • the curable composition of the present invention can be applied on a supporting substrate by a known means such as a roll coater, a curtain coater, various types of printing, and immersion. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
  • the material for the support substrate is not particularly limited and those usually used can be used.
  • inorganic materials such as glass; diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose Polyester; Polyurethane; Epoxy resin; Polycarbonate; Polyethylene terephthalate, Polyethylene naphthalate, Polybutylene terephthalate, Poly-1,4-cyclohexanedimethylene terephthalate, Polyethylene-1,2-diphenoxyethane -4,4'-dicarboxylate, polyester such as polybutylene terephthalate; polystyrene; polyethylene, polypropylene, polymethylpentene, etc.
  • Polyolefins Vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; Acrylic resins such as polymethyl methacrylate and polyacrylate; Polycarbonate; Polysulfone; Polyethersulfone; Polyetherketone; Polyetherimide; Polyoxy Polymer materials such as ethylene, norbornene resin, and cycloolefin polymer (COP) can be used.
  • the support substrate may be subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, and laser treatment.
  • curable composition of the present invention and the cured product include optical materials such as optical films, adhesives, glasses, and imaging lenses, paints, coating agents, lining agents, inks, resists, and liquids. Resist, printing plate, insulating varnish, insulating sheet, laminated board, printed circuit board, semiconductor device, LED package, liquid crystal inlet, organic EL, optical element, electrical insulation, electronic component, separation membrane, etc.
  • Sealant molding material, putty, glass fiber impregnating agent, sealant, passivation film for semiconductors and solar cells, interlayer insulating film, protective film, prism lens sheet used for backlight of liquid crystal display device
  • Lens parts of lens sheets such as Fresnel lens sheets and lenticular lens sheets used for screens of projection televisions, etc.
  • Backlights using a sheet can include an optical lens such as a micro lens, an optical element, an optical connector, an optical waveguide, a for optical fabricating casting agent.
  • a metal, wood, rubber, plastic, glass, ceramic product or the like is used as a substrate, and the curable composition of the present invention is applied to the substrate by the above-described means. And curing by light irradiation or heating.
  • a transparent support provided with various layers such as an undercoat layer, an antireflection layer, a hard coat layer, a gas barrier layer, a lubricating layer, and an adhesive layer as necessary may be mentioned. .
  • an inorganic material is used for the substrate, and a film coated by the above method, or vacuum deposition method, ion plating method, plasma CVD method, ion assist method, reactive sputtering method, chemical vapor phase It is also possible to use a laminate of films prepared by various vapor deposition methods such as a growth method.
  • the film thickness is, for example, 5 to 300 nm, although it varies depending on the type of inorganic material used.
  • the vapor deposition film may be formed only on one side of the substrate, or may be formed on both sides of the substrate.
  • the inorganic material examples include silicon (Si), aluminum (Al), magnesium (Mg), calcium (Ca), potassium (K), tin (Sn), indium (In), sodium (Na), and boron (B ), Titanium (Ti), lead (Pb), zirconium (Zr), yttrium (Y), antimony (Sb) and other oxides, indium-tin composite oxide (abbreviated as ITO), antimony-tin composite oxide A composite oxide such as a product (abbreviated as ATO) can be used.
  • examples of energy rays include ultraviolet rays, electron beams, X-rays, radiation, high frequencies and the like, and ultraviolet rays are most preferable economically.
  • examples of the ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp.
  • the conditions for curing the curable composition of the present invention by heating are 70 to 250 ° C. and 1 to 100 minutes.
  • pre-baking PAB
  • PEB pressurization and post-baking
  • baking may be performed at several different temperatures.
  • the heating conditions vary depending on the type and mixing ratio of each component. For example, it is 70 to 180 ° C., 5 to 15 minutes for an oven, and 1 to 5 minutes for a hot plate. Thereafter, in order to cure the coating film, a cured film can be obtained by heat treatment at 180 to 250 ° C., preferably 200 to 250 ° C., for 30 to 90 minutes for an oven and 5 to 30 minutes for a hot plate.
  • Examples 1 to 7, Comparative Examples 1 to 4 The components shown in Tables 1 and 2 were thoroughly mixed to obtain compositions of Examples 1 to 7 and Comparative Examples 1 to 4, respectively.
  • As the component (A), the following compounds (A1-1), (A2-1) to (A2-3), (A3-1), (A3-2) and (A4-1) are used, and
  • Compound A1-1 Celoxide 2021P (alicyclic epoxy: manufactured by Daicel)
  • Compound A2-1 1,4-butanediol diglycidyl ether
  • Compound A2-2 Adekaglycilol ED-523T (aliphatic epoxy: manufactured by ADEKA)
  • Compound A2-2 Neopentyl glycol diglycidyl ether compound A3-1: Aron oxetane OXT-221 (Oxetane: manufactured by Toagosei Co., Ltd.)
  • Compound A3-2 Aron oxetane OXT-101 (oxetane: manufactured by Toagosei Co., Ltd.)
  • Compound A4-1 Adeka Resin EP-4100 (Bisphenol A type polyfunctional epoxy: manufactured by ADEKA)
  • Compound C-1 KBM-403 (silane coupling agent: manufactured by Shin-Etsu Silicone)
  • Compound C-2 KBE-403 (Silane coupling agent: Shin-Etsu Silicone)
  • Adhesion 1 Each of the obtained curable compositions of Examples 1 to 5 and Comparative Examples 1 to 3 was applied to a single glass substrate (5 cm ⁇ 10 cm) with a bar coater # 3, and then COP ( A test piece was obtained by laminating with a cycloolefin polymer) film and using a metal halide lamp to irradiate energy of 1000 mJ / cm 2 at an illuminance of 250 mW / cm 2 and adhere. The obtained test piece was subjected to a 90 degree peel test. The results are shown in Tables 1 and 2.
  • composition 2 Each of the obtained compositions of Examples 6 and 7 and Comparative Example 4 was applied to a single TAC film, and then bonded to a COP (cycloolefin polymer) film subjected to corona discharge treatment using a laminator.
  • a test piece was obtained by applying an energy of 1000 mJ / cm 2 using an electrodeless ultraviolet light lamp and bonding. The obtained test piece was subjected to a 90 degree peel test. The results are shown in Tables 1 and 2.
  • the curable composition of the present invention has excellent adhesion and low viscosity.

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Abstract

La présente invention concerne une composition durcissable qui est utile dans un film optique, présente d'excellentes propriétés adhésives, et présente une faible viscosité, ainsi qu'un procédé de durcissement de ladite composition, et un produit durci obtenu au moyen dudit procédé. La composition durcissable comprend 100 parties en masse d'un composant durcissable cationique (A), et de 0,1 à 15 parties en masse d'un initiateur de polymérisation cationique (B), où le composant durcissable cationique (A) inclut, comme composants essentiels, un composé époxy alicyclique (A1), un composé époxy aliphatique (A2), et un composé oxétane (A3). Le composant durcissable cationique (A) contient en outre, de préférence, un composé époxy aromatique (A4).
PCT/JP2016/088250 2015-12-25 2016-12-21 Composition durcissable, procédé pour la durcir, et produit durci ainsi obtenu WO2017110951A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019021934A1 (fr) * 2017-07-28 2019-01-31 株式会社ダイセル Mélange de monomère, et composition durcissable contenant celui-ci
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