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WO2018181846A1 - Composition durcissable, procédé de production d'un produit durci, produit durci à base de celle-ci, et adhésif l'utilisant - Google Patents

Composition durcissable, procédé de production d'un produit durci, produit durci à base de celle-ci, et adhésif l'utilisant Download PDF

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Publication number
WO2018181846A1
WO2018181846A1 PCT/JP2018/013513 JP2018013513W WO2018181846A1 WO 2018181846 A1 WO2018181846 A1 WO 2018181846A1 JP 2018013513 W JP2018013513 W JP 2018013513W WO 2018181846 A1 WO2018181846 A1 WO 2018181846A1
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bis
ester
acridine
curable composition
compound
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PCT/JP2018/013513
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English (en)
Japanese (ja)
Inventor
和彦 松土
新之介 関
和幸 板野
一輝 長坂
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株式会社Adeka
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Priority to KR1020247017979A priority Critical patent/KR102756404B1/ko
Priority to KR1020197021935A priority patent/KR20190129830A/ko
Priority to JP2019510210A priority patent/JP7641089B2/ja
Priority to CN201880005553.2A priority patent/CN110114376B/zh
Publication of WO2018181846A1 publication Critical patent/WO2018181846A1/fr

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    • 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
    • C08F22/00—Homopolymers and copolymers 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
    • C08F22/10—Esters
    • C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J135/00—Adhesives based on homopolymers or copolymers 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 another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J135/02—Homopolymers or copolymers of esters
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic 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 C09J159/00 - C09J187/00

Definitions

  • the present invention relates to a curable composition, a method for producing a cured product, a cured product thereof, and an adhesive using the same, and more specifically, a curable composition having a low viscosity and a cured product having excellent adhesion,
  • the present invention relates to a method for producing a cured product, the cured product, and an adhesive using the same.
  • the curable composition is used in the fields of inks, paints, various coating agents, adhesives, optical members, and the like, and includes an energy ray curable composition containing a cationic polymerizable component and a radical polymerizable component, and a cured product thereof. Has been proposed.
  • Patent Document 1 proposes an adhesive composition for polarizing plates with improved initial curability and adhesiveness.
  • Patent Document 2 proposes an active energy ray-curable composition that provides a cured product with reduced curl properties and excellent transparency while maintaining high surface hardness.
  • the patent literature proposes an adhesive composition that is excellent in curability, adhesiveness, and water resistance and can be suitably used for the production of IT-related products.
  • the curable compositions such as those proposed in Patent Documents 1 to 3 are not necessarily sufficient in viscosity and adhesion of the cured product to the substrate, and further improvement is desired at present. .
  • An object of the present invention is to provide a curable composition capable of obtaining a cured product having low viscosity and excellent adhesion, a method for producing the cured product, the cured product, and an adhesive using the same. .
  • the curable composition of the present invention comprises 50 to 80 parts by mass of the radical polymerizable component (A), 1 to 10 parts by mass of the radical polymerization initiator (B), 20 to 50 parts by mass of the cationic polymerizable component (C) and A curable composition containing 1 to 10 parts by mass of a cationic polymerization initiator (D), wherein the total of the radical polymerizable component (A) and the cationic polymerizable component (C) is 100 parts by mass,
  • the cationic polymerizable component (C) contains glycidyl ether of alcohol having 11 or more carbon atoms.
  • the radical polymerizable component (A) is an acrylate ester of an alcohol having 2 to 60 carbon atoms or a methacrylate ester (A1) of an alcohol having 2 to 60 carbon atoms. Or an acrylic ester of a phenol compound or a methacrylic ester (A2) of a phenol compound.
  • the method for producing a cured product of the present invention is characterized in that the curable composition of the present invention is cured by irradiating active energy rays or cured by heating.
  • the cured product of the present invention is characterized by comprising the curable composition of the present invention.
  • the adhesive 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 with a low viscosity and a cured product having excellent adhesion, a method for producing the cured product, the cured product, and an adhesive using the same.
  • the curable composition of the present invention comprises 50 to 80 parts by mass of the radical polymerizable component (A), 1 to 10 parts by mass of the radical polymerization initiator (B), 20 to 50 parts by mass of the cationic polymerizable component (C), and cationic polymerization. 1 to 10 parts by mass of the initiator (D) is contained, and the total of the radical polymerizable component (A) and the cationic polymerizable component (C) is 100 parts by mass.
  • the cationically polymerizable component (C) contains glycidyl ether of alcohol having 11 or more carbon atoms. By setting it as such a composition, it becomes a curable composition with a low viscosity and the hardened
  • the radical polymerizable component (A) is not particularly limited as long as it is a compound that is polymerized or cross-linked by a radical polymerization initiator activated by irradiation with active energy rays or heating, and a known component can be used.
  • a radical polymerization initiator activated by irradiation with active energy rays or heating
  • a known component can be used.
  • an acrylate of an alcohol having 2 to 60 carbon atoms a methacrylate (A1) of an alcohol having 2 to 60 carbon atoms, an acrylic ester of a phenol compound or a methacrylic ester of a phenol compound (A2), acrylamide or methacryl
  • examples include amides, vinyl compounds, polyolefins, allyl urethane compounds, unsaturated polyester compounds, and styrene compounds.
  • Examples of the acrylate of an alcohol having 2 to 60 carbon atoms or the methacrylate (A1) of an alcohol having 2 to 60 carbon atoms include aromatic or aliphatic alcohols having at least one hydroxyl group in the molecule, and alkylenes thereof. Examples thereof include acrylates or methacrylates obtained by reacting an oxide adduct with acrylic acid or methacrylic acid.
  • polyhydric alcohol polyacrylates or polyhydric alcohol polymethacrylates are particularly preferred.
  • the acrylate of an alcohol having 2 to 60 carbon atoms or the methacrylate of an alcohol having 2 to 60 carbon atoms has 2 to 60 carbon atoms as an acrylate obtained by adding an acrylic group or a methacryl group to the alcohol. Means that.
  • acrylic ester of phenolic compound or methacrylic ester of phenolic compound (A2) phenol, cresol, butylphenol, resorcinol, hydroquinone, catechol, etc.
  • a phenolic compound having at least one aromatic ring, or its alkylene oxide addition Mono / polyacrylate or methacrylate of the product, for example, bisphenol A, bisphenol F, or a diacrylate or dimethacrylate of a compound obtained by further adding an alkylene oxide thereto.
  • acrylic acid ester of the phenol compound or the methacrylic acid ester (A2) of the phenol compound commercially available products can be used, for example, NK ester A-LEN-10, NK ester AMP-20GY, NK ester A-B1206PE.
  • Rate PO-A light acrylate P2H-A, light acrylate P-200A (manufactured by Kyoeisha Chemical Co., Ltd.); KAYARAD R-128H, KAYARAD R-551, KAYARAD R-712 (manufactured by Nippon Kayaku Co., Ltd.) Etc.
  • the proportion of the component (A1) is preferably 50 to 100% by mass, and preferably 60 to 100% by mass. Further preferred.
  • the proportion of the component (A2) is preferably 0 to 50% by mass, and more preferably 0 to 30% by mass.
  • radical polymerization initiator (B) used in the present invention examples include a photo radical polymerization initiator or a thermal radical polymerization initiator.
  • Preferred examples of the photopolymerization initiator include acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, bisimidazole compounds, acridine compounds, acylphosphine compounds, and oxime ester compounds. .
  • acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, and 2-hydroxymethyl.
  • -2-methylpropiophenone 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azide Benzalacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholino Phenyl) -butanone-1, Nzoin, benzoin methyl ether, benzoin ethyl ether, benzo
  • benzylic compound examples include benzyl.
  • benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like. It is done.
  • thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, and the like.
  • hexaarylbisimidazole (HABI, dimer of triaryl-imidazole) can be used.
  • HABI hexaarylbisimidazole
  • acridine compounds include acridine, 9-phenylacridine, 9- (p-methylphenyl) acridine, 9- (p-ethylphenyl) acridine, 9- (p-iso-propylphenyl) acridine, 9- (p -N-butylphenyl) acridine, 9- (p-tert-butylphenyl) acridine, 9- (p-methoxyphenyl) acridine, 9- (p-ethoxyphenyl) acridine, 9- (p-acetylphenyl) acridine 9- (p-dimethylaminophenyl) acridine, 9- (p-cyanophenylphenyl) acridine, 9- (p-chlorophenyl) acridine, 9- (p-bromophenyl) acridine, 9--
  • acylphosphine compounds examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Lucirin TPO; manufactured by BASF), isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, and pivaloyl-phenylphosphinic acid methyl.
  • Lucirin TPO 2,4,6-trimethylbenzoyldiphenylphosphine oxide
  • isobutyryl-methylphosphinic acid methyl ester isobutyryl-phenylphosphinic acid methyl ester
  • pivaloyl-phenylphosphinic acid methyl examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Lucirin TPO; manufactured by BASF), isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, and pivaloyl-phen
  • oxime ester compound examples include ethanone-1- [9-ethyl-6- (2-methylbenzoyl-9H-carbazol-3-yl] -1- (O-acetyloxime), 1- [9-ethyl].
  • thermal radical polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (methylisobutyrate), 2,2′-azobis-2,4-dimethylvaleronitrile, Azo initiators such as 1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di (4-t-butylcyclohexyl) )
  • Peroxide initiators such as peroxydicarbonate, and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.
  • the radical polymerization initiator (B) is a total of 100 of the radical polymerizable component (A) and the cationic polymerizable component (C).
  • the amount is preferably 1 to 10 parts by mass, more preferably 2 to 5 parts by mass with respect to parts by mass.
  • the cationic polymerizable component (C) is a compound that is polymerized or crosslinked by a cationic polymerization initiator activated by irradiation with active energy rays or heating, and is an essential component of an alcohol having 11 or more carbon atoms.
  • a polymer obtained from a monomer represented by formula (II), a polymer obtained from a monomer represented by formula (II) below, and two or more monomers selected from monomers represented by formula (I) below A polymer obtained from the body, a polymer obtained from two or more monomers selected from monomers represented by the following formula (II), or a single monomer represented by the following formula (I)
  • a polymer (C6) having a weight average molecular weight of 1,000 to 30,000 selected from the group of polymers obtained from monomers represented by the following formula (II) hereinafter also referred to as polymer (C6)
  • X is an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, or a carbon atom
  • An alicyclic hydrocarbon group of 6 to 10 or a hydrogen atom in these groups substituted with one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group is there.
  • R 1 represents a hydrogen atom, a methyl group or a halogen atom
  • X ′ represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a group having 6 to 10 carbon atoms
  • An alicyclic hydrocarbon group or a hydrogen atom in these groups is substituted with one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group.
  • Examples of the glycidyl ether of alcohol having 11 or more carbon atoms include triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, One or more alkylene oxides such as glycidyl ethers of polyhydric alcohols such as diglycidyl ether of polypropylene glycol and dicyclopentadiene dimethanol diglycidyl ether, and aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane and glycerin And polyglycidyl ether of polyether polyol obtained by adding.
  • the glycidyl ether of an alcohol having 11 or more carbon atoms means that the residue part has 11 or more carbon atoms in the glycidyl ether obtained by adding a glycidyl group to the alcohol.
  • the glycidyl ether of alcohol having 11 or more carbon atoms those having a saturated condensed ring are preferable because the curability and adhesion of the cured product are improved.
  • glycidyl ether of alcohol having 11 or more carbon atoms commercially available products can be used.
  • Denacol EX-171, Denacol EX-192, Denacol EX-830, Denacol EX-832, Denacol EX- 841, Denacol EX-861, Denacol EX-931 manufactured by Nagase ChemteX Corp.
  • Epolite M-1230, Epolite 400E, Epolite 400P Kyoeisha Chemical Co., Ltd.
  • Adeka Glycilol ED-506, Adeka Resin EP-4088S manufactured by ADEKA Corporation
  • the aromatic epoxy compound (C1) refers to an epoxy compound containing an aromatic ring.
  • Specific examples of the aromatic epoxy compound (C1) include monohydric / polyglycidyl etherified products of polyhydric phenols having at least one aromatic ring such as phenol, cresol, butylphenol, or alkylene oxide adducts thereof, such as bisphenol A.
  • a mono / polyglycidyl etherified compound of an aromatic compound having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, or catechol
  • Glycidyl etherified products of aromatic compounds having two or more alcoholic hydroxyl groups such as pheny
  • aromatic epoxy compound (C1) commercially available products can be used.
  • Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711, Denacol EX- 721, on coat EX-1020, on coat EX-1030, on coat EX-1040, on coat EX-1050, on coat EX-1051, on coat EX-1010, on coat EX-1011, on coat 1012 (Nagase Chem Tex Co., Ltd.); Ogsol PG-100, Ogsol EG-200, Ogsol EG-210, Ogsol EG-250 (Osaka Gas Chemical Co., Ltd.); HP4032, HP4032D, HP4700 (DIC Corporation) ); ESN-475V ( YX8800 (manufactured by Mitsubishi Chemical Corporation); Marproof G-0105SA, Marproof G-0130SP (manufactured by NOF Corporation); Epicron N-665, Epicron HP-7200 (
  • the aliphatic epoxy compound (C2) refers to an epoxy compound that is not classified as an aromatic epoxy compound (C1) or an alicyclic epoxy compound (C3) described later.
  • Specific examples of the aliphatic epoxy compound (C2) include monofunctional epoxy compounds such as glycidyl ethers of aliphatic alcohols and glycidyl esters of alkyl carboxylic acids, and polyglycidyl ethers of aliphatic polyhydric alcohols or alkylene oxide adducts thereof. And polyfunctional epoxy compounds such as polyglycidyl esters of aliphatic long-chain polybasic acids.
  • Representative compounds include glycidyl ethers of polyhydric alcohols such as allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, and aliphatic long-chain dibases.
  • the diglycidyl ester of an acid is mentioned.
  • monoglycidides of higher aliphatic alcohols further ethers, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxy stearate, butyl epoxy stearate, epoxidized polybutadiene and the like can be mentioned.
  • the aliphatic epoxy compound (C2) a glycidyl etherified product of an aliphatic alcohol other than a glycidyl ether of an alcohol having 11 or more carbon atoms, a polyglycidyl etherified product of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof, Viscosity, coatability and reactivity are improved, which is preferable.
  • aliphatic epoxy compound (C2) commercially available products can be used.
  • the alicyclic epoxy compound (C3) refers to a compound in which an oxirane ring is directly bonded to a saturated ring without a bonding group.
  • Specific examples of the alicyclic epoxy compound (C3) are 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.
  • Examples of the alicyclic epoxy compound (C3) include hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, or 3,4-epoxy-1-methylcyclohexyl-3,4. -Epoxy-1-methylhexanecarboxylate is preferred from the viewpoint of improving adhesion.
  • C3 alicyclic epoxy compound
  • examples thereof include Celoxide 2021P, Celoxide 2081, Celoxide 2000, Celoxa such as Id 3000 (manufactured by Daicel Corporation), and the like.
  • Examples of the oxetane compound (C4) include 3,7-bis (3-oxetanyl) -5-oxa-nonane, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, 1,2-bis.
  • oxetane compound (C4) commercially available products can be used.
  • Examples of the vinyl ether compound (C5) 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.
  • vinyl ether compound (C5) examples thereof include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.).
  • the content of glycidyl ether of alcohol having 11 or more carbon atoms improves the adhesion and low moisture permeability of the cured product, so that the radically polymerizable component (A) and the cationically polymerizable component are improved.
  • the amount is preferably 25 to 45 parts by weight, more preferably 28 to 43 parts by weight, based on 100 parts by weight in total with the component (C).
  • aromatic epoxy compound (C1) aliphatic epoxy compound (C2), alicyclic epoxy compound (C3), oxetane compound (C4)
  • the vinyl ether compound (C5) and the polymer (C6) are used in a proportion of 1 to 10 parts by weight of the aromatic epoxy compound (C1) with respect to 100 parts by mass in total of the radical polymerizable component (A) and the cationic polymerizable component (C).
  • the amount by weight and the polymer (C6) of 0 to 15 parts by weight are preferred because the viscosity, coatability, reactivity and curability are improved.
  • the component (C) is 20 to 50 parts by mass with respect to a total of 100 parts by mass of the components (A) and (C).
  • a compound having an epoxy group and an ethylenically unsaturated group can also be used.
  • these compounds include epoxy acrylate or epoxy methacrylate.
  • aromatic epoxy resins, alicyclic epoxy resins, aliphatic epoxy resins and the like, acrylic acid or methacrylic acid Is an acrylate obtained by reacting Among these epoxy acrylates or epoxy methacrylates, particularly preferred are acrylates or methacrylates of glycidyl ethers of alcohols.
  • the cationic polymerization initiator (D) may be any compound that can release a substance that initiates cationic polymerization by irradiation with active energy rays or heating. Is preferably a double salt which is an onium salt that releases a Lewis acid by irradiation with active 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.
  • at least one is preferably an organic group as described above having an aromatic ring.
  • 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- in the above general formula examples include halogen ion, perchlorate ion (ClO 4 ) ⁇ , tetrafluoroborate ion (BF 4 ) ⁇ , hexafluorophosphate ion (PF 6 ).
  • Inorganic ions such as hexafluoroantimonate (SbF 6 ) - , hexafluoroarsenate (AsF 6 ) - , hexachloroantimonate (SbCl 6 ) - ; trifluoromethanesulfonate ion, methanesulfonate ion, butanesulfonate ion , fluorosulfonic acid ion (FSO 3) -, a benzenesulfonate anion, toluenesulfonate ion, trinitrobenzene sulfonate ion, camphor sulfonate ion, nonafluorobutanesulfonate ion, such as hexa decafluoro octanoic acid ion scan Phosphonic acid ion; boric acid ion such as tetraaryl borate ion,
  • 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.
  • the onium salts it is particularly effective to use the following aromatic onium salts (a) to (c).
  • aromatic onium salts (a) to (c) one of them can be used alone, or two or more of them can be mixed and used.
  • Aryl diazonium 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, and 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 viewpoint of practical use and improvement of photosensitivity, and an aromatic sulfonium salt having the following structure is converted into a cationic polymerization initiator (D ) It is more preferable to contain at least 0.1% by mass with respect to 100% by mass.
  • the proportion of the cationic polymerization initiator (D) used is 1 to 10 parts by weight, preferably 100 parts by weight in total of the radical component (A) and the cationic polymerization component (C). 2 to 5 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.
  • a sensitizer and / or a sensitization aid can be further used 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 (D) and promotes the polymerization initiation reaction by the cationic polymerization initiator (D).
  • 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 (IIIa).
  • anthracene compound represented by the formula (IIIa) include the following compounds.
  • R 6 and R 7 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • naphthalene compound represented by the above formula (IIIb) 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
  • Examples thereof include 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 cationic polymerizable component (C) 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. From the viewpoint of improving curability, the sensitizer and the sensitization agent are each preferably 0.1 to 3 parts by mass or more with respect to 100 parts by mass of the polymerizable component (C).
  • a silane coupling agent can be used as necessary.
  • the silane coupling agent include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltrimethoxysilane.
  • Alkyl-functional alkoxysilanes vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, and other alkenyl-functional alkoxysilanes, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxy Silane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, ⁇ Epoxy-functional alkoxysilanes such as glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ Aminofunctional alkoxysilanes such as amino
  • the amount of the silane coupling agent used is not particularly limited, but is usually in the range of 0.01 to 20 parts by mass with respect to 100 parts by mass of the total amount of solids in the curable composition.
  • the properties of the cured product can be improved by using a thermoplastic organic polymer as necessary.
  • the thermoplastic organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate ethyl acrylate copolymer, methyl methacrylate glycidyl methacrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, Examples include (meth) acrylic acid-methyl methacrylate copolymer, glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymer, polyvinyl butyral, cellulose ester, polyacrylamide, and saturated polyester.
  • the curable composition of the present invention is not particularly limited, and a solvent that can dissolve or disperse the components (A), (B), (C), and (D) that are usually used can be used.
  • Ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxy Ether solvents such as ethane, propylene glycol monomethyl ether, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lac
  • cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether
  • alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol and amyl alcohol
  • ethylene glycol monomethyl acetate Ether ester solvents such as ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate
  • benzene, toluene, BTX solvents such as xylene
  • aliphatic hydrocarbon solvents such as hexane, heptane, octane, cyclohexane
  • turpentine oil D-limonene, pinet Terpene hydrocarbon oils such as mineral spirits, paraffinic solvent
  • the water content is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less because the curability, adhesiveness, and liquid storage stability are improved. Too much moisture is not preferred because it may cause cloudiness or components may precipitate.
  • the UV-absorbing agent is inactivated at room temperature, and the protective group is released by heating to a predetermined temperature, light irradiation, acid, etc. and activated.
  • a compound exhibiting ultraviolet absorbing ability can also be used.
  • coloring agents such as polyols, inorganic fillers, organic fillers, pigments, dyes, antifoaming agents, thickeners, surfactants, leveling agents, difficulty
  • resin additives such as flame retardants, thixotropic agents, diluents, plasticizers, stabilizers, polymerization inhibitors, UV absorbers, antioxidants, antistatic agents, flow regulators, adhesion promoters, etc. may be added. it can.
  • the curable composition of the present invention is applied onto a support 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; Polycarbonates; Polysulfones; Polyether sulfones; Polyether ketones; Polyether imides; Examples thereof include polymer materials such as norbornene resin and cycloolefin polymer (COP).
  • COP cycloolefin polymer
  • 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, laser treatment and the like.
  • surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment and the like.
  • examples of the active energy rays include ultraviolet rays, electron beams, X-rays, radiation, high frequencies, and the like, and ultraviolet rays are most economically preferable.
  • examples of the ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp.
  • the conditions for the method of curing the curable composition of the present invention by heating are 70 to 250 ° C. and 1 to 100 minutes. After performing pre-baking (PAB), pressurization and post-baking (PEB) may be performed, or baking may be performed at several different temperatures.
  • the heating conditions vary depending on the type and mixing ratio of each component, but are, for example, 70 to 180 ° C., 5 to 15 minutes for an oven, and 1 to 5 minutes for a hot plate.
  • 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.
  • curable composition of the present invention or a cured product thereof include adhesives, glasses, optical materials represented by imaging lenses, paints, coating agents, lining agents, inks, resists, liquid resists, printing Plates, color TVs, PC monitors, personal digital assistants, digital cameras, organic EL, touch panels and other display elements, insulating varnishes, insulating sheets, laminates, printed boards, semiconductor devices, LED packages, liquid crystal inlets, organic Sealants for EL, optical elements, electrical insulation, electronic parts, separation membranes, molding materials, putty, glass fiber impregnating agents, sealants, passivation films for semiconductors and solar cells, interlayers Insulating film, protective film, prism lens sheet used for backlight of liquid crystal display device, Fresnel label used for screen of projection TV, etc. Lens parts of lens sheets such as lens sheets, lenticular lens sheets, or backlights using such sheets, optical lenses such as micro lenses, optical elements, optical connectors, optical waveguides, castings for optical modeling, etc. Can be mentioned
  • a transparent support As a display device, a transparent support, an undercoat layer, an antireflection layer, a polarizing element layer, a retardation layer, a birefringence layer, a light scattering layer, a hard coating layer, a lubricating layer, a protective layer, etc., as necessary
  • cured material of this invention can be used for each layer.
  • ⁇ Initial adhesion> A An adhesive force of more than 0.5 N / 2 cm is shown.
  • X Adhesive strength of 0.5 N / 2 cm or less is shown.
  • X Adhesive strength of 1.5 N / 2 cm or less is shown.
  • the moisture permeability of the acrylic film alone was 50 g / m 2 / day.
  • the radical polymerizable component (A) the following compounds (A1-1) to (A1-5) and (A2-1) were used.
  • Compound A1-1 1,6-hexanediol diacrylate
  • Compound A1-2 Biscote # 150 (tetrahydrofurfuryl acrylate; manufactured by Osaka Organic Chemical Co., Ltd.)
  • Compound A1-3 NK ester A-DCP (tricyclodecane dimethanol diacrylate; manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • Compound A1-4 NK ester APG-200 (tripropylene glycol diacrylate; manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • Compound A1-5 A-9300S (polyfunctional acrylate; manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • Compound A2-1 NK ester BPE-500 (ethoxylated bisphenol A dimethacrylate; manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • Compound C1-1 EP-4100 (bisphenol A type diglycidyl ether: manufactured by ADEKA Corporation)
  • Compound C2-1 Adeka Resin EP-4088L (diglycidyl ether of alcohol having 11 or more carbon atoms; manufactured by ADEKA Corporation)
  • Compound C2-2 1,4-butanediol diglycidyl ether compound
  • C2-3 Neopentyl glycol diglycidyl ether compound
  • C2-4 Epiklone HP-7200 (dicyclopentadiene type glycidyl ether; manufactured by DIC Corporation)
  • Compound C3-1 Celoxide 2021P (alicyclic epoxy compound; manufactured by Daicel Corporation)
  • Compound C6-1 copolymer of 70 parts by weight of methyl methacrylate and 30 parts by weight of glycidyl methacrylate (weight

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne : une composition durcissable qui présente une faible viscosité et permet l'obtention d'un produit durci qui présente une excellente adhésivité ; un procédé de production d'un produit durci ; un produit durci à base de la composition durcissable ; et un adhésif qui utilise la composition durcissable. L'invention concerne donc une composition durcissable qui contient 50 à 80 parties en masse d'un composant polymérisable par voie radicalaire (A), 1 à 10 parties en masse d'un initiateur de polymérisation radicalaire (B), 20 à 50 parties en masse d'un composant polymérisable par voie cationique (C) et 1 à 10 parties en masse d'un initiateur de polymérisation cationique (D), le total du composant polymérisable par voie radicalaire (A) et du composant polymérisable par voie cationique (C) étant égal à 100 parties en masse. Le composant polymérisable par voie cationique (C) contient un éther glycidylique d'un alcool qui possède au moins 11 atomes de carbone.
PCT/JP2018/013513 2017-03-31 2018-03-29 Composition durcissable, procédé de production d'un produit durci, produit durci à base de celle-ci, et adhésif l'utilisant WO2018181846A1 (fr)

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JP7631987B2 (ja) 2021-03-30 2025-02-19 三菱ケミカル株式会社 活性エネルギー線硬化性接着剤組成物、偏光板用接着剤組成物、偏光板用接着剤、偏光板

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CN111258180B (zh) * 2018-11-30 2024-03-08 常州正洁智造科技有限公司 六芳基双咪唑类混合光引发剂及应用
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