Curable composition, method for producing cured product, cured product, and adhesive using the same

Abstract

The present invention provides a curable composition that gives a cured product with low viscosity and excellent adhesion, a method for producing the cured product, the cured product, and an adhesive using the same. A curable composition comprising 50 to 80 parts by mass of a radical polymerizable component (A), 1 to 10 parts by mass of a radical polymerization initiator (B), 20 to 50 parts by mass of a cationic polymerizable component (C), and 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, and the cationic polymerizable component (C) comprises a glycidyl ether of an alcohol having 11 or more carbon atoms. [Selection diagram] None

Description

[Technical field]

[0001] The present invention relates to a curable composition, a method for producing a cured product, the cured product, and an adhesive using the same, and more particularly to a curable composition which gives a cured product having low viscosity and excellent adhesion, a method for producing a cured product, the cured product, and an adhesive using the same. [Background technology]

[0002] Curable compositions are used in the fields of inks, paints, various coating agents, adhesives, optical members, and the like, and energy ray-curable compositions containing a cationically polymerizable component and a radically polymerizable component and cured products thereof have been proposed.

[0003] For example, Patent Document 1 proposes an adhesive composition for polarizing plates with improved initial curing properties and adhesion. Patent Document 2 proposes an active energy ray curable composition that provides a cured product with reduced curling and excellent transparency while maintaining high surface hardness. Patent Document 2 also proposes an adhesive composition that is excellent in curing properties, adhesion properties, and water resistance and can be suitably used in the manufacture of IT-related products. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2014-037477 A [Patent Document 2] JP 2016-102193 A [Patent Document 3] International Publication No. 2014 / 178239 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the curable compositions proposed in Patent Documents 1 to 3 do not necessarily have sufficient viscosity and the cured products do not necessarily have sufficient adhesion to substrates, and further improvements are currently desired.

[0006] Accordingly, an object of the present invention is to provide a curable composition which gives 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. [Means for solving the problem]

[0007] As a result of extensive investigations aimed at solving the above problems, the present inventors have found that a composition having a specific composition can solve the above problems, and have thus completed the present invention.

[0008] That is, the curable composition of the present invention comprises 50 to 80 parts by mass of a radical polymerizable component (A), 1 to 10 parts by mass of a radical polymerization initiator (B), 20 to 50 parts by mass of a cationic polymerizable component (C), and 1 to 10 parts by mass of a cationic polymerization initiator (D), wherein the total amount of the radical polymerizable component (A) and the cationic polymerizable component (C) is 100 parts by mass, the cationic polymerizable component (C) contains a glycidyl ether of an alcohol having 11 or more carbon atoms, the glycidyl ether of an alcohol having 11 or more carbon atoms includes a glycidyl ether of an alcohol having a saturated condensed ring having 11 or more carbon atoms, and the glycidyl ether of an alcohol having a saturated condensed ring having 11 or more carbon atoms is 25 to 45 parts by mass per 100 parts by mass of the total of the radically polymerizable component (A) and the cationic polymerizable component (C); the radically polymerizable component (A) contains an acrylic acid ester of an alcohol having 2 to 60 carbon atoms or a methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1); In the radical polymerizable component (A), the proportion of the acrylic acid ester of an alcohol having 2 to 60 carbon atoms or the methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1) is 50 to 100 mass %, Further, the acrylic acid ester of an alcohol having 2 to 60 carbon atoms or the methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1) is at least one selected from the group consisting of 1,6-hexanediol diacrylate, tetrahydrofurfuryl acrylate, tricyclodecane dimethanol diacrylate, tripropylene glycol diacrylate, 1,6-hexanediol dimethacrylate, and tetrahydrofurfuryl methacrylate.

[0010] 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 it with active energy rays or by heating it.

[0011] Furthermore, the cured product of the present invention is characterized by being made of the curable composition of the present invention.

[0012] Furthermore, the adhesive of the present invention is characterized by comprising the curable composition of the present invention. Effect of the Invention

[0013] According to the present invention, it is possible to provide a curable composition that can give 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. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The curable composition of the present invention will be described in detail below. The curable composition of the present invention contains 50 to 80 parts by mass of a radical polymerizable component (A), 1 to 10 parts by mass of a radical polymerization initiator (B), 20 to 50 parts by mass of a cationic polymerizable component (C), and 1 to 10 parts by mass of a cationic polymerization initiator (D), and the total of the radical polymerizable component (A) and the cationic polymerizable component (C) is 100 parts by mass. In the curable composition of the present invention, the cationic polymerizable component (C) contains a glycidyl ether of an alcohol having 11 or more carbon atoms. By using such a composition, the curable composition can be obtained which has low viscosity and provides a cured product with excellent adhesion.

[0015] The radical polymerizable component (A) is not particularly limited as long as it is a compound that undergoes a polymerizing or crosslinking reaction by a radical polymerization initiator activated by irradiation with active energy rays or heating, and any known compound can be used. Examples of the radical polymerizable component (A) include acrylates of alcohols having 2 to 60 carbon atoms or methacrylates of alcohols having 2 to 60 carbon atoms (A1), acrylic acid esters of phenolic compounds or methacrylic acid esters of phenolic compounds (A2), as well as acrylamides or methacrylamides, vinyl compounds, polyolefins, allyl urethane compounds, unsaturated polyester compounds, and styrene-based compounds.

[0016] Examples of the acrylate or methacrylate (A1) of an alcohol having 2 to 60 carbon atoms include acrylates or methacrylates obtained by reacting aromatic or aliphatic alcohols having at least one hydroxyl group in the molecule and their alkylene oxide adducts with acrylic acid or methacrylic acid. Specific examples of the acrylate or methacrylate include 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isoamyl acrylate, lauryl acrylate, stearyl acrylate, isooctyl acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, benzyl acrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, trimethylolpropane triacrylate, pentaacrylate, tetramethylolpropane tri ... Erythritol tetraacrylate, dipentaerythritol hexaacrylate, ε-caprolactone modified dipentaerythritol hexaacrylate, 2-ethylhexyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, isoamyl methacrylate, lauryl methacrylate, stearyl methacrylate, isooctyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, benzyl methacrylate, 1,3-butanediol dimethacrylate, 1, Examples of the methacrylate include 4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, and ε-caprolactone-modified dipentaerythritol hexamethacrylate.Among these acrylates or methacrylates, polyacrylates of polyhydric alcohols or polymethacrylates of polyhydric alcohols are particularly preferred. Here, the acrylate of an alcohol having 2 to 60 carbon atoms or the methacrylate of an alcohol having 2 to 60 carbon atoms means an acrylate having 2 to 60 carbon atoms in which an acryl group or a methacryl group is added to an alcohol.

[0017] As the acrylate of an alcohol having 2 to 60 carbon atoms or the methacrylate of an alcohol having 2 to 60 carbon atoms (A1), a commercially available product may be used. For example, NK Ester AM-90G, NK Ester AM-130G, NK Ester A-SA, NK Ester S-1800A, NK Ester 701A, NK Ester A-200, NK Ester A-400, NK Ester A-600, NK Ester A-1000, NK Ester A-DCP, NK Ester A-DOD-N, NK Ester A-HD-N, NK Ester APG-100, NK Ester APG-200, NK Ester APG-400, NK Ester APG-700, NK Ester A-PTMG-65, NK Ester A-9300, NK Ester A-9300-1CL, NK Ester A-1000-2CL, NK Ester A-1000-1CL, NK Ester A-1000-1CL, NK Ester A-1000-2 ... A-GLY-20E, NK Ester A-TMM-3L, NK Ester A-TMM-3LM-N, NK Ester A-TMPT, NK Ester AD-TMP, NK Ester ATM-35E, NK Ester A-TMMT, NK Ester A-9550, NK Ester A-DPH, NK Ester M-90G, NK Ester M-230G, NK Ester S, NK Ester SA, NK Ester 1G, NK Ester 2G, NK Ester 3G, NK Ester 4G, NK Ester 9G, NK Ester 14G, NK Ester 23G, NK Ester DCP, NK Ester DOD-N, NK Ester HD-N, NK Ester NOD-N, NK Ester NPG, NK Ester 1206PE, NK Ester 701, NK Ester 9PG, NK Ester TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.);HEA, HPA, 4-HBA, AIB, TBA, NOAA, INAA, Viscoat #197, IDAA, LA, STA, ISTA (Osaka Organic Chemical Industry Co., Ltd.), Light Acrylate IAA, Light Acrylate LA, Light Acrylate SA, Light Acrylate EC-A, Light Acrylate MTG-A, Light Acrylate EHDG-AT, Light Acrylate 130A, Light Acrylate DPM-A, Light Acrylate IB-XA, Light Ester HOA(N), Light Ester HOP-A(N), Light Acrylate HOB-A, HOA-MS(N), Light Acrylate HOA-HH (N), Light Acrylate 3EG-A, Light Acrylate 4EG-A, Light Acrylate 9EG-A, Light Acrylate 14EG-A, Light Acrylate PTMGA-250, Light Acrylate NP-A, Light Acrylate MPD-A, Light Acrylate 1,6HX-A, Light Acrylate 1,9ND-A, Light Acrylate DCP-A, Light Acrylate HPP-A, Light Ester G-201P, Light Acrylate TMP-A, Light Acrylate PE-3A, Light Acrylate PE-4A, Light Acrylate DPE-6A (manufactured by Kyoeisha Chemical Co., Ltd.); KAYARAD NPGDA, KAYARAD PEG400DA, KAYARAD FM-400, KAYARAD R-167, KAYARAD HX-220, KAYARAD HX-620, KAYARAD R-604, KAYARAD R-684, KAYARAD GPO-303, KAYARAD TMPTA, KAYARAD PET-30 (manufactured by Nippon Kayaku Co., Ltd.), etc.;

[0018] Examples of the acrylate esters of phenol compounds or methacrylate esters of phenol compounds (A2) include mono / polyacrylates or methacrylates of phenol compounds having at least one aromatic ring, such as phenol, cresol, butylphenol, resorcinol, hydroquinone, catechol, etc., or alkylene oxide adducts thereof, such as diacrylates or dimethacrylates of compounds obtained by further adding alkylene oxide to these compounds, for example, bisphenol A, bisphenol F, and the like.

[0019] The acrylic acid ester of a phenol compound or the methacrylic acid ester of a phenol compound (A2) may be a commercially available product. For example, NK Ester A-LEN-10, NK Ester AMP-20GY, NK Ester A-B1206PE, NK Ester ABE-300, NK Ester A-BPE-10, NK Ester A-BPE-20, NK Ester A-BPE-30, NK Ester A-BPE-4, NK Ester A-BPEF, NK Ester A-BPE-3, NK Ester PHE-1G, NK Ester BPE-80N, NK Ester BPE-100, NK Ester BPE-200, NK Ester BPE-500, NK Ester BPE-900, NK Ester BPE-1300N (manufactured by Shin-Nakamura Chemical Co., Ltd.); Light Acrylate 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.

[0020] In the radical polymerizable component (A), the proportion of the (A1) component is preferably 50 to 100 mass%, more preferably 60 to 100 mass%, since this improves the curability and adhesion of the cured product. The proportion of the (A2) component is preferably 0 to 50 mass%, more preferably 0 to 30 mass%.

[0021] In the curable composition of the present invention, the amount of the radically polymerizable component (A) is preferably 50 to 80 parts by mass, more preferably 50 to 65 parts by mass, per 100 parts by mass of the total of the radically polymerizable component (A) and the cationic polymerizable component (C), since this improves the curability and the adhesion of the cured product.

[0022] The radical polymerization initiator (B) used in the present invention includes a photoradical polymerization initiator or a thermal radical polymerization initiator.

[0023] Preferred examples of the photopolymerization initiator include acetophenone-based compounds, benzyl-based compounds, benzophenone-based compounds, thioxanthone-based compounds, bisimidazole-based compounds, acridine-based compounds, acylphosphine-based compounds, and oxime ester compounds.

[0024] Examples of the acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, p-dimethylaminoacetophenone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzalacetophenone, 1-hydroacetophenone, 1-methyl-2-propanol ... Examples of such benzenesulfonyl ethers include 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, and 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one.

[0025] The benzyl compounds include benzyl and the like.

[0026] Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 4-benzoyl-4'-methyldiphenyl sulfide.

[0027] Examples of the thioxanthone compounds include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

[0028] As the bisimidazole compound, hexaarylbisimidazole (HABI, a dimer of triaryl-imidazole) can be used. Specifically, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-bis(2-bromophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl- 1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2-bromophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dibromophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-tribromophenyl)- 2,4,5,2',4',5'-hexaphenylbisimidazole, 2,2'-bis(2-chlorophenyl)-4,5,4',5'-tetraphenylbisimidazole, 2,2'-bis(2-bromophenyl)-4,5,4',5'-tetraphenylbisimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,5,4',5'-tetraphenylbisimidazole, 2,2'-bis(2-chlorophenyl)-4,5,4',5'-tetrakis(3-methoxyphenyl) phenyl)bisimidazole, 2,2'-bis(2-chlorophenyl)-4,5,4',5'-tetrakis(3,4,5-trimethoxyphenyl)-bisimidazole, 2,5,2',5'-tetrakis(2-chlorophenyl)-4,4'-bis(3,4-dimethoxyphenyl)bisimidazole, 2,2'-bis(2,6-dichlorophenyl)-4,5,4',5'-tetraphenylbisimidazole, 2,2'-bis(2-nitrophenyl)-4,5,4',5'-tetraphenylbisimidazole, 2,2'-di-o-tolyl-4,5,4',5'-Tetraphenylbisimidazole, 2,2'-bis(2-ethoxyphenyl)-4,5,4',5'-tetraphenylbisimidazole and 2,2'-bis(2,6-difluorophenyl)-4,5,4',5'-tetraphenylbisimidazole, 5'-tetra(p-iodophenyl)biimidazole, 2,2'-bis(o-chlorophenyl-4,4',5,5'-tetra(m-methoxyphenyl)biimidazole ), 2,2'-bis(p-methylthiophenyl)-4,5,4',5'-diphenyl-1,1'-biimidazole, bis(2,4,5-triphenyl)-1,1'-biimidazole, 5,5'-tetra(p-chloronaphthyl)biimidazole, and the like, as well as tautomers having 1,2'-, 1,4'-, and 2,4'-covalent bonds disclosed in JP-B-45-37377, and compounds described in WO00 / 52529.

[0029] Examples of the acridine compounds include acridine, 9-phenylacridine, 9-(p-methylphenyl)acridine, 9-(p-ethylphenyl)acridine, 9-(p-isopropylphenyl)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, and 9-(p-cyanophenylphenyl)acridine. 9-(p-chlorophenyl)acridine, 9-(p-bromophenyl)acridine, 9-(m-methylphenyl)acridine, 9-(m-propylphenyl)acridine, 9-(m-isopropylphenyl)acridine, 9-(m-butylphenyl)acridine, 9-(m-tert-butylphenyl)acridine, 9-(m-methoxyphenyl)acridine, 9-(m-ethoxyphenyl)acridine, 9-(m-acetylphenyl)acridine, 9-(m-dimethylaminophenyl)acridine, 9-(m-diethylaminophenyl)acridine )acridine, 9-(cyanophenyl)acridine, 9-(m-chlorophenyl)acridine, 9-(m-bromophenyl)acridine, 9-methylacridine, 9-ethylacridine, 9-n-propylacridine, 9-iso-propylacridine, 9-cyanoethylacridine, 9-hydroxyethylacridine, 9-chloroethylacridine, 9-bromoacridine, 9-hydroxyacridine, 9-nitroacridine, 9-aminoacridine, 9-methoxyacridine, 9-ethoxyacridine, 9-n-propoxyacridine, 9-i so-propoxyacridine, 9-chloroethoxyacridine, 4,6-bis(dimethylamino)acridine, 10-acetate acridine, 10-methylacetate acridine, 3,6-dimethylacridine, 7,13-dimethylacridine, 7,13-bis(dimethylamino)acridine, 3,6-dimethyl-10-acetate acridine, 3,5-dimethyl-10-methylacetate acridine, 7,13-dimethyl-10-acetate acridine, 7,13-dimethyl-10-methylacetate acridine, 1,7-bis(9-acridinyl)heptane, 1,5-Bis(9-acridinyl)pentane, 1,3-bis(9-acridinyl)propane, 2,7-dibenzoyl-9-phenylacridine, 2,7-bis(α-hydroxybenzyl)-9-phenylacridine, 2,7-bis(α-acetoxybenzyl)-9-phenylacridine, 2,7-dimethyl-9-(4-methylphenyl)acridine, 2,7-dimethyl-9-phenylacridine, 2,7-bis(3,4-dimethyl-benzoyl)-9-(3,4-dimethylphenyl)acridine, 2,7-bis(α-acetoxy-4-tert-butylbenzyl)-9-phenylacridine 2,7-dimethyl-9-(3,4-dichlorophenyl)acridine, 2,7-dimethyl-9-(4-benzoylphenyl)acridine, 2,7-bis(2-chlorobenzoyl)-9-(2-chlorophenyl)acridine, 2-(α-hydroxy-3-bromobenzyl)-6-methyl-9-(3-bromophenyl)acridine, 2,5-bis(4-tert-butylbenzoyl)-9-(4-tert-butylphenyl)acridine, 1,4-bis(2,7-dimethyl-9-acridinyl)benzene , 2,7-bis(α-phenylaminocarbonyloxy-3,4-dimethylbenzyl)-9-(3,4-dimethylphenyl)acridine and 2,7-bis(3,5-dimethyl-4-hydroxy-4'-fluorodiphenylmethyl)-9-(4-fluorophenyl)acridine, 9,10-dihydroacridine, 1-methylacridine, 4-methylacridine, 2,3-dimethylacridine, 1-phenylacridine, 4-phenylacridine, 1-benzylacridine, 4-benzylacridine, 1-chloroacridine, 2,3-dichloroacridine, 1 0-Butyl-2-chloroacridin-9(10H)-one, 10-propyl-2-chloroacridin-9(10H)-one, 10-butyl-2-chloroacridin-9(10H)-one 1,2-bis(9-acridinyl)ethane, 1,3-bis(9-acridinyl)propane, 1,4-bis(9-acridinyl)butane, 1,6-bis(9-acridinyl)hexane, 1,7-bis(9-acridinyl)heptane, 1,8-bis(9-acridinyl)octane, 1,9-bis(9-acridinyl)nonane, 1,10-bis(9-acridinyl)decane, 1,11-bis(9-acridinyl)undecane, 1,12-bis(9-acridinyl)dodecane, 1,14-bis(9-acridinyl)tetradecane, 1,16-bis(9-acridinyl)hexadecane, 1,18-bis(9-acridinyl)octadecane, 1,20-bis(9-acridinyl)eicosane, 1,3-bis(9-acridinyl)-2-thiapropane, 1,5-bis(9-acridinyl)-3-thiapentane 7-methyl-benzo[c]acridine, 7-ethyl-benzo[c]acridine, 7-propyl-benzo[c]acridine, 7-butyl- benzo(c)acridine, 7-pentyl-benzo(c)acridine, 7-hexyl-benzo(c)acridine, 7-heptyl-benzo(c)acridine, 7-octyl-benzo(c)acridine, 7-nonyl-benzo(c)acridine, 7-decyl-benzo(c)acridine, 7-undecyl-benzo(c)acridine, 7-dodecyl-benzo(c)acridine, 7-tridecyl-benzo(c)acridine, 7-tetradecyl-benzo(c)acridine, 7-pentadecyl-benzo(c)acridine, 7-hexadecyl-benzo(c)acridine, 7-heptadecy-benzo(c)acridine 7-octadecyl-benzo[c]acridine, 7-nonadecyl-benzo[c]acridine, 1,1-bis(7-benzo[c]acridinyl)methane, 1,2-bis(7-benzo[c]acridinyl)ethane, 1,3-bis(7-benzo[c]acridinyl)propane, 1,4-bis(7-benzo[c]acridinyl)butane, 1,5-bis(7-benzo[c]acridinyl)pentane, 1,6-bis(7-benzo[c]acridinyl)hexane, 1,7-bis(7-benzo[c]acridinyl) 1,8-bis(7-benzo[c]acridinyl)heptane, 1,8-bis(7-benzo[c]acridinyl)octane, 1,9-bis(7-benzo[c]acridinyl)nonane, 1,10-bis(7-benzo[c]acridinyl)decane, 1,11-bis(7-benzo[c]acridinyl)undecane, 1,12-bis(7-benzo[c]acridinyl)dodecane, 1,13-bis(7-benzo[c]acridinyl)tridecane, 1,14-bis(7-benzo[c]acridinyl)tetradecane, 1,15-bis(7-benzo[c]acridinyl)pentadecane, 1,16-bis(7-benzo[c]acridinyl)hexadecane, 1,17-bis(7-benzo[c]acridinyl)heptadecane, 1,18-bis(7-benzo[c]acridinyl)octadecane, 1,19-bis(7-benzo[c]acridinyl)nonadecane, 1,20-bis(7-benzo[c]acridinyl)eicosane, 7-phenyl-benzo[c]acridin, 7-(2-chlorophenyl)-benzo[c]acridin, 7-(4-methylphenyl)-benzo[c]acridin , 7-(4-nitrophenyl)-benzo[c]acridine, 1,3-bis(7-benzo[c]acridinyl)benzene, 1,4-bis(7-benzo[c]acridinyl)benzene, 7-[1-propen-3-yl(benzo[c]acridinyl)], 7-[1-ethylpentyl-(benzo[c]acridinyl)], 7-[8-heptadecenyl-(benzo[c]acridinyl)], 7,8-diphenyl-1,14-bis(7-benzo[c]acridinyl)tetradecane, 1,2-bis(7-benzo[c]acridinyl)benzene, 1-methyl-1,2-bis(7-benzo(c)acridinyl)ethylene, 7-styryl-benzo(c)acridine, 7-(1-propenyl)-benzo(c)acridine, 7-(1-pentenyl)-benzo(c)acridine, 9-(2-pyridyl)acridine, 9-(3-pyridyl)acridine, 9-(4-pyridyl)acridine, 9-(4-pyrimidinyl)acridine, 9-(2-pyrazinyl)acridine, 9(5-methyl-2-pyrazinyl)acridine acridine, 9-(2-quinolinyl)acridine, 9-(2-pyridyl)-2-methyl-acridine, 9-(2-pyridyl)-2-ethylacridine, 9-(3-pyridyl)-2-methyl-acridine, 9-(3-pyridyl)-2,4-diethyl-acridine, 3,6-diamino-acridine sulfonate, 3,6-bis-(dimethylamino)-acridine sulfonate, 3,6-diamino-10-methyl-acridinium chloride, 9-acridine carboxylic acid, etc.

[0030] As the acylphosphine compound, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Lucirin TPO; manufactured by BASF), isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, pivaloyl-phenylphosphinic acid methyl ester, 2-ethylhexanoyl-phenylphosphinic acid methyl ester, pivaloyl-phenylphosphinic acid isopropyl ester, p-toluyl-phenylphosphinic acid methyl ester, o-toluyl-phenylphosphinic acid methyl ester, 2,4-dimethylbenzoyl-phenylphosphinic acid methyl ester, p-tert-butylbenzoyl-phenylphosphinic acid isopropyl ester, acryloyl-phenylphosphinic acid methyl ester, isobutyryl-diphenylphosphine oxide, 2-ethylhexanoyl-diphenylphosphine oxide, o-toluyl-diphenylphosphine oxide, p-tert-butylbenzoyl-diphenylphosphine oxide, 3-pyridylcarbonyl-diphenylphosphine oxide, acryloyl-diphenylphosphine oxide, benzoyl-diphenylphosphine oxide, pivaloyl-phenylphosphine oxide, pivaloyl-phenylphosphine acid vinyl ester, adipoyl-bis-diphenylphosphine oxide, pivaloyl-diphenylphosphine oxide, p-toluyl-diphenylphosphine oxide, 4-(tertiary butyl)-benzoyl-diphenylphosphine oxide, 2-methylbenzoyl-diphenylphosphine oxide, 2-methyl-2-ethylhexanoyl-diphenylphosphine oxide, 1-methyl-cyclohexanoyl-diphenylphosphine oxide, pivaloyl-phenylphosphine acid methyl ester and pivaloyl-phenylphosphine acid isopropyl ester, 4-octylphenylphosphine oxide, terephthaloyl-bis-diphenylphosphine oxide, 1-methyl-cyclohexylcarbonyldiphenylphosphine oxide, versatoyl-diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-diisobutoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Irgacure 819; BASF), bis(2,4,6-trimethylbenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-4-ethoxyphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methyl Bis(2-methyl-1-naphthoyl)-2-naphthylphosphine oxide, bis(2-methyl-1-naphthoyl)-4-propylphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methoxy-1-naphthoyl)-4-ethoxyphenylphosphine oxide, bis(2-chloro-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-dioctyloxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-diisopropoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-dihexyloxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2-propoxy-4-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-di Isopentyloxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-biphenylylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2-naphthylphosphine oxide, bis(2,6-dichlorobenzoyl)-1-naphthylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide (CGI403), 6-trimethylbenzoyl-ethyl-phenyl-phosphinate (SPEEDCURE TPO-L; manufactured by Lambson), etc.

[0031] Examples of the oxime ester compound include ethanone-1-[9-ethyl-6-(2-methylbenzoyl-9H-carbazol-3-yl]-1-(O-acetyl oxime), 1-[9-ethyl-6-benzoyl-9H-carbazol-3-yl]-octan-1-one oxime-O-acetate, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-ethan-1-one oxime-O-benzoate, 1-[9-n-butyl-6-(2-ethylbenzoyl)-9H-carbazol-3-yl]-ethan-1-one oxime-O-benzoate, ethanone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofuranylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyl oxime), oxime), ethanone-1-[9-ethyl-6-(2-methyl-4-tetrahydropyranylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-(2-methyl-5-tetrahydrofuranylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzoyl}-9H-carbazol-3-yl]-1-(O-acetyloxime), ethanone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofuranylmethoxybenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), and the like.

[0032] Examples of the thermal radical polymerization initiator include azo initiators such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(methylisobutyrate), 2,2'-azobis-2,4-dimethylvaleronitrile, and 1,1'-azobis(1-acetoxy-1-phenylethane); peroxide initiators such as benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butyl peroxypivalate, and di(4-t-butylcyclohexyl)peroxydicarbonate; and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.

[0033] In the curable composition of the present invention, the radical polymerization initiator (B) is preferably 1 to 10 parts by mass, more preferably 2 to 5 parts by mass, per 100 parts by mass of the total of the radically polymerizable component (A) and the cationic polymerizable component (C), since this improves the curability and the adhesion of the cured product.

[0034] The cationic polymerizable component (C) is a compound that undergoes a polymerization or crosslinking reaction by a cationic polymerization initiator activated by irradiation with active energy rays or heating. In addition to the essential component, glycidyl ether of an alcohol having 11 or more carbon atoms, aromatic epoxy compounds (C1), aliphatic epoxy compounds (C2), alicyclic epoxy compounds (C3), oxetane compounds (C4), vinyl ether compounds (C5), polymers obtained from a monomer represented by the following formula (I), polymers obtained from a monomer represented by the following formula (II), polymers obtained from two or more monomers selected from the monomer represented by the following formula (I), polymers obtained from two or more monomers selected from the monomer represented by the following formula (II), or polymers obtained from a monomer represented by the following formula (I) and a monomer represented by the following formula (II), having a weight average molecular weight of 1,000 to 30,000 (hereinafter also referred to as polymer (C6)) may be used.

[0035] TIFF0007641089000001.tif22156 (In the formula, 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 an alicyclic hydrocarbon group having 6 to 10 carbon atoms, or a group in which a hydrogen atom in any of these groups has been 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.)

[0036] TIFF0007641089000002.tif37156 (in the formula, R 1 represents a hydrogen atom, a methyl group, or a halogen atom, and X' represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, 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.

[0037] Examples of the glycidyl ether of alcohol having 11 or more carbon atoms include glycidyl ether of polyhydric alcohol such as triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, dicyclopentadiene dimethanol diglycidyl ether, and polyglycidyl ether of polyether polyol obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohol such as propylene glycol, trimethylolpropane, and glycerin. Here, the glycidyl ether of alcohol having 11 or more carbon atoms means that the number of carbon atoms in the residue portion is 11 or more in the glycidyl ether obtained by adding a glycidyl group to an alcohol. As the glycidyl ether of alcohol having 11 or more carbon atoms, one having a saturated condensed ring is preferable because it improves the curability and adhesion of the cured product.

[0038] As the glycidyl ether of an alcohol having 11 or more carbon atoms, commercially available products can be used, such as Denacol EX-171, Denacol EX-192, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, and Denacol EX-931 (manufactured by Nagase ChemteX Corporation); Epolight M-1230, Epolight 400E, and Epolight 400P (manufactured by Kyoeisha Chemical Co., Ltd.), Adeka Glycirol ED-506, and Adeka Resin EP-4088S (manufactured by ADEKA Corporation).

[0039] Aromatic epoxy compound (C1) refers to an epoxy compound containing an aromatic ring. Specific examples of aromatic epoxy compound (C1) include mono / polyglycidyl ethers of polyhydric phenols having at least one aromatic ring, such as phenol, cresol, butylphenol, or their alkylene oxide adducts, such as glycidyl ethers of bisphenol A, bisphenol F, or compounds obtained by further adding alkylene oxide to these, and epoxy novolac resins; mono / polyglycidyl ethers of aromatic compounds having two or more phenolic hydroxyl groups, such as resorcinol, hydroquinone, and catechol; glycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, such as phenyl dimethanol, phenyl diethanol, and phenyl dibutanol; glycidyl esters of polybasic aromatic compounds having two or more carboxylic acids, such as phthalic acid, terephthalic acid, and trimellitic acid, glycidyl esters of benzoic acid, epoxidized products of styrene oxide or divinylbenzene, and the like.

[0040] As the aromatic epoxy compound (C1), commercially available products can be used, for example, Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711, Denacol EX-721, Oncoat EX-1020, Oncoat EX-1030, Oncoat EX-1040, Oncoat EX-1050, Oncoat EX-1051, Oncoat EX-1010, Oncoat EX-1011, Oncoat 1012 (manufactured by Nagase ChemteX Corporation); Oxol PG-100, Oxol EG-200, Oxol EG-210, Oxol EG-250 (manufactured by Osaka Gas Chemicals Co., Ltd.); HP4032, HP4032D, HP 4700 (DIC Corporation); ESN-475V (Tohto Kasei Corporation); YX8800 (Mitsubishi Chemical Corporation); Marproof G-0105SA, Marproof G-0130SP (NOF Corporation); Epicron N-665, Epicron HP-7200 (DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103 S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); ADEKA RESIN EP-4000, ADEKA RESIN EP-4005, ADEKA RESIN EP-4100, ADEKA RESIN EP-4901 (manufactured by ADEKA Corporation); TECHMORE VG-3101L (manufactured by Printec Co., Ltd.). As the aromatic epoxy compound (C1), a polyfunctional one is preferable because of its excellent curability.

[0041] Aliphatic epoxy compounds (C2) refer to epoxy compounds that are not classified as aromatic epoxy compounds (C1) or alicyclic epoxy compounds (C3) described below. Specific examples of aliphatic epoxy compounds (C2) include monofunctional epoxy compounds such as glycidyl ethers of aliphatic alcohols and glycidyl esters of alkyl carboxylic acids, polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts, and 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, and neopentyl glycol diglycidyl ether, and diglycidyl esters of aliphatic long-chain dibasic acids. In addition, monoglycidyl ethers of aliphatic higher alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, epoxy octyl stearate, epoxy butyl stearate, and epoxidized polybutadiene. As the aliphatic epoxy compound (C2), a glycidyl ether product of an aliphatic alcohol other than the above-mentioned glycidyl ethers of alcohols having 11 or more carbon atoms, or a polyglycidyl ether product of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof is preferred because it improves viscosity, coatability and reactivity.

[0042] As the aliphatic epoxy compound (C2), commercially available products can be used. For example, Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-211, Denacol EX-212, Denacol EX-313, Denacol EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX-512, Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-622, Denacol EX-810, Denacol EX-811, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-833, Denacol EX-834, Denacol EX-835, Denacol EX-836, Denacol EX-837, Denacol EX-838, Denacol EX-839, Denacol EX-840, Denacol EX-841, Denacol EX-842, Denacol EX-843, Denacol EX-844, Denacol EX-845, Denacol EX-846, Denacol EX-847, Denacol EX-848, Denacol EX-849, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-849, Denacol EX-849, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-842, Denacol Examples of the resins include Epolight M-1230, Epolight 40E, Epolight 100E, Epolight 200E, Epolight 400E, Epolight 70P, Epolight 200P, Epolight 400P, Epolight 1500NP, Epolight 1600, Epolight 80MF, and Epolight 100MF (manufactured by Kyoeisha Chemical Co., Ltd.), Adeka Glysilol ED-503, Adeka Glysilol ED-503G, Adeka Glysilol ED-506, Adeka Glysilol ED-523T, and Adeka Resin EP-4088S (manufactured by ADEKA Corporation).

[0043] 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) include polyglycidyl ethers of polyhydric alcohols having at least one alicyclic ring, and cyclohexene oxide- or cyclopentene oxide-containing compounds obtained by epoxidizing cyclohexene- or cyclopentene ring-containing compounds with an oxidizing agent. For example, hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexane carboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexane carboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexane carboxylate, bis(3,4-epoxycyclohexyl) (dimethyl methyl) adipate, 3,4-epoxy-6-methylcyclohexane carboxylate, methylene bis(3,4-epoxycyclohexane), propane-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexane carboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, α-pinene oxide, limonene dioxide, and the like.

[0044] As the alicyclic epoxy compound (C3), 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.

[0045] As the alicyclic epoxy compound (C3), commercially available products can be used, and examples thereof include Celloxide 2021P, Celloxide 2081, Celloxide 2000, and Celloxide 3000 (manufactured by Daicel Corporation).

[0046] 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[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl Examples of such compounds include bifunctional aliphatic oxetane compounds such as 1,4-bis(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, and 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, and monofunctional oxetane compounds such as 3-ethyl-3-[(phenoxy)methyl]oxetane, 3-ethyl-3-(hexyloxymethyl)oxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(hydroxymethyl)oxetane, and 3-ethyl-3-(chloromethyl)oxetane. These compounds can be used alone or in combination of two or more, and polyfunctional oxetane compounds are preferred because they have high curability and adhesion to the cured product.

[0047] As the oxetane compound (C4), commercially available products can be used, such as ARON OXETANE OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, and OXT-212 (manufactured by Toagosei Co., Ltd.), Ethanacole OXBP, and OXTP (manufactured by Ube Industries, Ltd.).

[0048] 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, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, and 1,6-cyclohexanedimethanol divinyl ether.

[0049] As the vinyl ether compound (C5), commercially available products can also be used, and examples thereof include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, and 4-hydroxybutyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.).

[0050] In the cationic polymerizable component (C), the content of the glycidyl ether of an alcohol having 11 or more carbon atoms is preferably 25 to 45 parts by mass, and more preferably 28 to 43 parts by mass, per 100 parts by mass of the total of the radically polymerizable component (A) and the cationic polymerizable component (C), because this improves the adhesion and low moisture permeability of the cured product. In addition to the essential component, glycidyl ether of alcohol having 11 or more carbon atoms, the aromatic epoxy compound (C1), aliphatic epoxy compound (C2), alicyclic epoxy compound (C3), oxetane compound (C4), vinyl ether compound (C5), and polymer (C6) are preferably used in an amount of 1-20 parts by mass of aromatic epoxy compound (C1), 20-40 parts by mass of aliphatic epoxy compound (C2), 0-20 parts by mass of alicyclic epoxy compound (C3), 10-30 parts by mass of oxetane compound (C4), 0-20 parts by mass of vinyl ether compound (C5), and 0-15 parts by mass of polymer (C6) per 100 parts by mass of the total of radical polymerizable component (A) and cationic polymerizable component (C), because this improves viscosity, coatability, reactivity, and curability. Note that the amount of component (C) is 20-50 parts by mass per 100 parts by mass of the total of components (A) and (C).

[0051] In addition to the radical polymerizable component (A) and the cationic polymerizable component (C), a compound having an epoxy group and an ethylenically unsaturated group can also be used. For example, these compounds can include epoxy acrylates or epoxy methacrylates, specifically, acrylates obtained by reacting a conventionally known aromatic epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin, etc. with acrylic acid or methacrylic acid. Among these epoxy acrylates or epoxy methacrylates, particularly preferred are acrylates or methacrylates of glycidyl ethers of alcohols.

[0052] The cationic polymerization initiator (D) in the curable composition of the present invention may be any compound capable of releasing a substance that initiates cationic polymerization upon irradiation with active energy rays or heating, but is preferably a double salt, which is an onium salt that releases a Lewis acid upon irradiation with active energy rays, or a derivative thereof. Representative examples of such compounds include those represented by the following general formula: [A] r+ [B] r- Examples of the salt include salts of cations and anions represented by the following formula:

[0053] Here, cation [A] r+ is preferably an onium, the structure of which is, for example, the following general formula: [(R 2 ) a Q] r+ It can be expressed as:

[0054] Furthermore, here, R 2 is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms. a is an integer of 1 to 5. a R 2 are each independent and may be the same or different. At least one of them is preferably an organic group having an aromatic ring as described above. Q is an atom or atomic group selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, and N=N. Also, the cation [A] r+ When the valence of Q in the formula is q, the relationship r=aq must hold (however, N=N is treated as having a valence of 0).

[0055] In addition, the anion [B] r- is preferably a halide complex, the structure of which is, for example, represented by the following general formula: [LY b ] r- It can be expressed as:

[0056] Furthermore, here, L is a metal or semimetal (metalloid) that is the central atom of the halide complex, such as B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co, etc. Y is a halogen atom. b is an integer of 3 to 7. In addition, the anion [B] r- When the valence of L in is p, the relationship r=bp must hold.

[0057] The anion of the above general formula [LY b ] r- Specific examples include halogen ions and perchlorate ions (ClO4). - , tetrafluoroborate ion (BF4) - , hexafluorophosphate ion (PF6) - , Hexafluoroantimonate (SbF6) - , Hexafluoroarsenate (AsF6) - , Hexachloroantimonate (SbCl6) - Inorganic ions such as trifluoromethanesulfonate ion, methanesulfonate ion, butanesulfonate ion, and fluorosulfonate ion (FSO3) - , sulfonate ions such as benzenesulfonate anion, toluenesulfonate ion, trinitrobenzenesulfonate ion, camphorsulfonate ion, nonafluorobutanesulfonate ion, and hexadecafluorooctane sulfonate ion; borate ions such as tetraarylborate ion and tetrakis(pentafluorophenyl)borate ion; carboxylate ions such as methanecarboxylate ion, ethanecarboxylate ion, propanecarboxylate ion, butanecarboxylate ion, octanecarboxylate ion, trifluoromethanecarboxylate ion, benzenecarboxylate ion, and p-toluenecarboxylate ion; trifluoromethylsulfite ion (CF3SO3) - , methyl sulfate ion (CH3OSO3) - , bis(trifluoromethanesulfonyl)imide ion, tris(trifluoromethanesulfonyl)methide ion, (CF3CF2)3PF3 - , ((CF3)2C6H3)4B -, (C6F5)4Ga - , ((CF3)2C6H3)4Ga - In addition, examples include those selected from the following group.

[0058] TIFF0007641089000003.tif156155

[0059] In addition, the anion [B] r- is represented by the following general formula: [LY b-1 (OH)] r- The structure represented by the following formula can also be preferably used. L, Y, and b are the same as above. Other anions that can be used include perchlorate ion (ClO4) - , trifluoromethylsulfite ion (CF3SO3) - , fluorosulfonate ion (FSO3) - , toluenesulfonate anion, trinitrobenzenesulfonate anion, camphorsulfonate, nonafluorobutanesulfonate, hexadecafluorooctane sulfonate, tetraarylborate, tetrakis(pentafluorophenyl)borate, and the like.

[0060] In the curable composition of the present invention, among such onium salts, the following aromatic onium salts (A) to (C) are particularly effective for use. Among these, one type may be used alone, or two or more types may be used in combination.

[0061] (a) Aryl diazonium salts such as phenyl diazonium hexafluorophosphate, 4-methoxyphenyl diazonium hexafluoroantimonate, and 4-methylphenyl diazonium hexafluorophosphate.

[0062] (b) Diaryl iodonium salts such as diphenyl iodonium hexafluoroantimonate, di(4-methylphenyl) iodonium hexafluorophosphate, di(4-tert-butylphenyl) iodonium hexafluorophosphate, and triaryl iodonium tetrakis(pentafluorophenyl)borate.

[0063] (c) Sulfonium cations represented by the following Group I or Group II and sulfonium salts such as hexafluoroantimony ion, hexafluorophosphate ion, and tetrakis(pentafluorophenyl)borate ion.

[0064] <Group I> TIFF0007641089000004.tif198163

[0065] <Group II> JPEG0007641089000005.jpg123149

[0066] In addition, other preferable ones are (η 5-2,4-cyclopentadien-1-yl)[(1,2,3,4,5,6-η)-(1-methylethyl)benzene]-iron-hexafluorophosphate and other iron-arene complexes, mixtures of aluminum complexes such as tris(acetylacetonato)aluminum, tris(ethylacetonatoacetato)aluminum, and tris(salicylaldehyde)aluminum with silanols such as triphenylsilanol; salts such as thiophenium salts, thioranium salts, benzylammonium salts, pyridinium salts, and hydrazinium salts; diethylenetriamine, triethylene Polyalkyl polyamines such as lenthriamine and tetraethylenepentamine; alicyclic polyamines such as 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane and isophoronediamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone; the above polyamines and glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A diglycidyl ether and bisphenol F diglycidyl ether or glycidyl ethers of carboxylic acids polyepoxy addition modified products produced by reacting the above organic polyamines with various epoxy resins such as olefins and olefin esters in a conventional manner; amidation modified products produced by reacting the above organic polyamines with carboxylic acids such as phthalic acid, isophthalic acid, dimer acid in a conventional manner; Mannich modified products produced by reacting the above polyamines with aldehydes such as formaldehyde and phenols having at least one aldehyde reactive site in the nucleus such as phenol, cresol, xylenol, tertiary butylphenol, resorcin in a conventional manner. Polycarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer acid, dimer acid, and other aliphatic dicarboxylic acids; aromatic dicarboxylic acids such as phthalic acid, terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid;Examples of the acid anhydrides include tricarboxylic acids such as trimellitic acid, trimesic acid, and trimers of castor oil fatty acid; tetracarboxylic acids such as pyromellitic acid; dicyandiamide, imidazoles, carboxylates, sulfonates, and amine imides.

[0067] Among these, from the viewpoints of practical use and improving photosensitivity, it is preferable to use aromatic iodonium salts, aromatic sulfonium salts, and iron-arene complexes, and it is more preferable to contain at least 0.1 mass% or more of an aromatic sulfonium salt having the following structure, relative to 100 mass% of the cationic polymerization initiator (D).

[0068] In the curable composition of the present invention, the proportion of the cationic polymerization initiator (D) used is 1 to 10 parts by mass, preferably 2 to 5 parts by mass, per 100 parts by mass of the total of the radical component (A) and the cationic polymerization component (C). If the proportion is too small, curing tends to be insufficient, whereas if the proportion is too large, it may adversely affect various physical properties such as the water absorption rate and strength of the cured product.

[0069] The curable composition of the present invention may further contain a sensitizer and / or a sensitizing aid, if necessary. The sensitizer is a compound that exhibits a maximum absorption at a wavelength longer than the maximum absorption wavelength exhibited by the cationic polymerization initiator (D) and promotes the polymerization initiation reaction by the cationic polymerization initiator (D). The sensitizing aid is a compound that further promotes the action of the sensitizer.

[0070] Examples of the sensitizer and the sensitization assistant include anthracene-based compounds and naphthalene-based compounds.

[0071] An example of the anthracene compound is represented by the following formula (IIIa).

[0072] TIFF0007641089000006.tif34168 Wherein, in formula (IIIa), R 3 and R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms; R5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0073] Specific examples of the anthracene compound represented by formula (IIIa) include the following compounds.

[0074] For example, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-diisopropoxyanthracene, 9,10-dibutoxyanthracene, 9,10-dipentyloxyanthracene, 9,10-dihexyloxyanthracene, 9,10-bis(2-methoxyethoxy)anthracene, 9,10-bis(2-ethoxyethoxy)anthracene, 9,10-bis(2-butoxyethoxy)anthracene, 9,10-bis(3-butoxypropoxy)anthracene, 2 2-methyl- or 2-ethyl-9,10-dimethoxyanthracene, 2-methyl- or 2-ethyl-9,10-diethoxyanthracene, 2-methyl- or 2-ethyl-9,10-dipropoxyanthracene, 2-methyl- or 2-ethyl-9,10-diisopropoxyanthracene, 2-methyl- or 2-ethyl-9,10-dibutoxyanthracene, 2-methyl- or 2-ethyl-9,10-dipentyloxyanthracene, 2-methyl- or 2-ethyl-9,10-dihexyloxyanthracene, and the like.

[0075] An example of the naphthalene-based compound is represented by the following formula (IIIb).

[0076] TIFF0007641089000007.tif34168 Wherein, in formula (IIIb), R 6 and R 7 each independently represents an alkyl group having 1 to 6 carbon atoms.

[0077] Specific examples of the naphthalene-based compound represented by the above formula (IIIb) include the following compounds.

[0078] Examples include 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, and 1,4-dibutoxynaphthalene.

[0079] The proportions of the sensitizer and sensitization aid relative to the cationic polymerizable component (C) are not particularly limited, and they may be used in generally normal proportions within the range that does not impair the object of the present invention. From the viewpoint of improving curability, for example, it is preferable that the sensitizer and sensitization aid are each 0.1 to 3 parts by mass or more relative to 100 parts by mass of the cationic polymerizable component (C).

[0080] In the curable composition of the present invention, a silane coupling agent can be used as necessary. Examples of the silane coupling agent include alkyl functional alkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and the like, alkenyl functional alkoxysilanes such as vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, and allyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and β-(3,4-epoxycyclohexyl)ethyl. Examples of the alkoxysilanes that can be used include epoxy-functional alkoxysilanes such as N-β(aminoethyl)-γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, and N-phenyl-γ-aminopropyltrimethoxysilane; mercapto-functional alkoxysilanes such as γ-mercaptopropyltrimethoxysilane; titanium alkoxides such as titanium tetraisopropoxide and titanium tetra normal butoxide; titanium chelates such as titanium dioctyloxybis(octylene glycolate) and titanium diisopropoxybis(ethyl acetoacetate); zirconium chelates such as zirconium tetraacetylacetonate and zirconium tributoxy monoacetylacetonate; zirconium acylates such as zirconium tributoxy monostearate; and isocyanate silanes such as methyltriisocyanate silane.

[0081] 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.

[0082] The properties of the cured product can be improved by using a thermoplastic organic polymer in the curable composition of the present invention as necessary. Examples of 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, (meth)acrylic acid-methyl methacrylate copolymer, glycidyl (meth)acrylate-polymethyl (meth)acrylate copolymer, polyvinyl butyral, cellulose ester, polyacrylamide, and saturated polyester.

[0083] For the curable composition of the present invention, there can be used, without any particular limitation, a commonly used solvent capable of dissolving or dispersing each of the above components (A), (B), (C) and (D), and examples thereof include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol monomethyl ether, and dipropylene glycol dimethyl. Ether solvents such as ether; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; 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, ethylene glycol monoethyl acetate, and proline. Ether ester solvents such as pyrene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, and ethoxyethyl propionate; BTX solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and cyclohexane; terpene hydrocarbon oils such as turpentine oil, D-limonene, and pinene; parabens such as mineral spirits, Swazol #310 (Cosmo Matsuyama Oil Co., Ltd.), and Solvesso #100 (Exxon Chemical Co., Ltd.). Examples of suitable solvents include fin-based solvents; halogenated aliphatic hydrocarbon-based solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; halogenated aromatic hydrocarbon-based solvents such as chlorobenzene; propylene carbonate, carbitol-based solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, and water. These solvents can be used alone or in combination of two or more.

[0084] The curable composition of the present invention has an improved curability, adhesiveness, and liquid storage stability, and therefore the water content is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less. Too much water is undesirable because it may cause clouding or precipitation of components.

[0085] The curable composition of the present invention may further contain, as necessary, an ultraviolet absorber or a compound that is inactive at room temperature but is activated by heating to a predetermined temperature, irradiation with light, an acid, or the like to eliminate a protecting group and thereby exhibit ultraviolet absorbing ability.

[0086] Furthermore, as long as the effects of the present invention are not impaired, various resin additives, such as polyols, inorganic fillers, organic fillers, colorants such as pigments and dyes, defoamers, thickeners, surfactants, leveling agents, flame retardants, thixotropic agents, diluents, plasticizers, stabilizers, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, flow adjusters, and adhesion promoters, may be added as necessary.

[0087] The curable composition of the present invention is applied onto a supporting substrate by a known means such as a roll coater, a curtain coater, various printing methods, immersion, etc. In addition, after being applied onto a supporting substrate such as a film, it can also be transferred onto another supporting substrate, and there is no limitation on the application method.

[0088] The material of the supporting substrate is not particularly limited, and any commonly used material can be used, for example, inorganic materials such as glass; cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamide; polyimide; polyurethane; epoxy resin; polycarbonate; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene, and polymethylpentene; vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic resins such as polymethyl methacrylate and polyacrylate; polycarbonate; polysulfone; polyethersulfone; polyetherketone; polyetherimide; and polymer materials such as polyoxyethylene, norbornene resin, and cycloolefin polymer (COP).

[0089] The supporting substrate may be subjected to a surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment or the like.

[0090] In the method of curing the curable composition of the present invention by irradiation with active energy rays, examples of the active energy rays include ultraviolet rays, electron beams, X-rays, radioactive rays, and high frequency waves, and ultraviolet rays are economically most preferable. Examples of the source of ultraviolet rays include ultraviolet lasers, mercury lamps, xenon lasers, and metal halide lamps.

[0091] The conditions for the method of curing the curable composition of the present invention by heating are 70 to 250°C for 1 to 100 minutes. After pre-baking (PAB; pre-applied bake), pressure may be applied and post-baked (PEB; post exposure bake), or baking may be performed at several different temperatures. The heating conditions vary depending on the types and blending ratios of each component, but are, for example, 70 to 180°C, 5 to 15 minutes in an oven, or 1 to 5 minutes on a hot plate. Thereafter, in order to cure the coating film, a cured film can be obtained by heat-treating at 180 to 250°C, preferably 200 to 250°C, for 30 to 90 minutes in an oven, or 5 to 30 minutes on a hot plate.

[0092] Specific applications of the curable composition of the present invention or a cured product thereof include adhesives, glasses, optical materials such as imaging lenses, paints, coating agents, lining agents, inks, resists, liquid resists, printing plates, color televisions, PC monitors, personal digital assistants, digital cameras, display elements such as organic electroluminescence (EL) and touch panels, insulating varnishes, insulating sheets, laminates, printed circuit boards, sealants for semiconductor devices, LED packages, liquid crystal injection ports, organic electroluminescence (EL) and optical elements, electrical insulation, electronic components, and separation membranes, molding materials, putties, glass fiber impregnating agents, sealants, passivation films for semiconductors and solar cells, interlayer insulating films, protective films, prism lens sheets used in the backlights of liquid crystal display devices, Fresnel lens sheets used in the screens of projection televisions, and the like, lens portions of lens sheets such as lenticular lens sheets, or backlights using such sheets, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, and casting agents for optical shaping.

[0093] Examples of the display device include a transparent support on which various layers such as an undercoat layer, an antireflection layer, a polarizing element layer, a retardation layer, a birefringence layer, a light scattering layer, a hard coat layer, a lubricating layer, and a protective layer are provided as necessary, and a film made of the cured product of the present invention can be used for each layer. EXAMPLES

[0094] The present invention will be described in more detail below with reference to examples and comparative examples. In the examples and comparative examples, "parts" refers to "parts by mass."

[0095] [Examples 1 to 11, Comparative Examples 1 to 4] The components were thoroughly mixed according to the formulations shown in Tables 1 to 3 below to obtain curable compositions of Examples 1 to 11 and Comparative Examples 1 to 4. The obtained curable compositions were evaluated for viscosity and adhesion according to the following procedures.

[0096] (viscosity) The viscosity of each of the obtained curable compositions was measured with an E-type viscometer at 25° C. The results are shown in [Tables 1] to [Table 3].

[0097] (Adhesion) Each of the obtained curable compositions was applied to a sheet of acrylic film (Technoloy 125S001, manufactured by Sumitomo Chemical Co., Ltd.) that had been subjected to a corona discharge treatment, and then the film was laminated with another sheet of COP (cycloolefin polymer, Zeon Corporation: Zeonorfilm 14-060) film that had been subjected to a corona discharge treatment using a laminator. The film was then exposed to 1000 mJ / cm using an electrodeless ultraviolet lamp. 2 The test pieces were bonded by irradiating light equivalent to 10 ...

[0098] <Initial adhesion> ○: Shows an adhesive strength of more than 0.5 N / 2 cm. ×: Adhesive strength of 0.5 N / 2 cm or less. <Adhesion after curing> ○: Shows an adhesive strength of more than 1.5 N / 2 cm. ×: Adhesive strength of 1.5 N / 2 cm or less.

[0099] (moisture permeability) Each of the obtained curable compositions was applied to a sheet of acrylic film (Technoloy 75S001, manufactured by Sumitomo Chemical Co., Ltd.) that had been subjected to a corona discharge treatment, and then the film was exposed to 500 mJ / cm 2 of ultraviolet light using an electrodeless ultraviolet lamp. 2 A test piece was obtained by irradiating the film with light equivalent to 50 g / m2. The test piece was then left to stand for 6 hours or more in an environment of 23°C (humidity 50%). The moisture permeability of the obtained test piece was measured using a water vapor transmission rate measuring device 7002 (manufactured by ILLINOIS INSTRUMENTS, INC.). The test environment was 40°C / 90% RH. Evaluation was performed according to the following criteria. The moisture permeability of the acrylic film alone was 50 g / m2. 2 It was / day. ◎:≦40g / m 2 Indicates / day. ○:<50g / m 2 Indicates / day. ×:≧50g / m 2 Indicates / day.

[0100] As the radically 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: Viscoat #150 (tetrahydrofurfuryl acrylate; manufactured by Osaka Organic 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 (multifunctional 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.)

[0101] As the radical polymerization initiator (B), the following compound (B-1) was used. Compound B1-1: Irgacure 184 (BASF)

[0102] As the cationically polymerizable component (C), the following compounds (C1-1), (C2-1) to (C2-4), (C3-1) and (C6-1) were used. Compound C1-1: EP-4100 (bisphenol A 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: Epicron HP-7200 (dicyclopentadiene type glycidyl ether; manufactured by DIC Corporation) Compound C3-1: Celloxide 2021P (alicyclic epoxy compound; manufactured by Daicel Corporation) Compound C6-1: A copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 8000)

[0103] As the cationic polymerization initiator (D), the following compound D-1 was used. Compound D-1: A 50% solution of a mixture of two compounds represented by the following structures in propylene carbonate.

[0104] TIFF0007641089000008.tif37168

[0105] TIFF0007641089000009.tif40168

[0106] [Table 1]

[0107] [Table 2]

[0108] [Table 3]

[0109] It is apparent from [Tables 1] to [Table 3] that the curable composition of the present invention is excellent in curability and adhesion of the cured product.

Claims

1. A curable composition comprising 50 to 80 parts by mass of a radical polymerizable component (A), 1 to 10 parts by mass of a radical polymerization initiator (B), 20 to 50 parts by mass of a cationic polymerizable component (C), and 1 to 10 parts by mass of a cationic polymerization initiator (D), wherein the total amount of the radical polymerizable component (A) and the cationic polymerizable component (C) is 100 parts by mass, the cationic polymerizable component (C) contains a glycidyl ether of an alcohol having 11 or more carbon atoms, the glycidyl ether of an alcohol having 11 or more carbon atoms includes a glycidyl ether of an alcohol having a saturated fused ring having 11 or more carbon atoms, and the glycidyl ether of an alcohol having a saturated fused ring having 11 or more carbon atoms is 25 to 45 parts by mass per 100 parts by mass of the total of the radically polymerizable component (A) and the cationic polymerizable component (C); the radical polymerizable component (A) contains an acrylic acid ester of an alcohol having 2 to 60 carbon atoms or a methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1); In the radical polymerizable component (A), the proportion of the acrylic acid ester of an alcohol having 2 to 60 carbon atoms or the methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1) is 50 to 100 mass %, The curable composition is further characterized in that the acrylic acid ester of an alcohol having 2 to 60 carbon atoms or the methacrylic acid ester of an alcohol having 2 to 60 carbon atoms (A1) is at least one selected from the group consisting of 1,6-hexanediol diacrylate, tetrahydrofurfuryl acrylate, tricyclodecane dimethanol diacrylate, tripropylene glycol diacrylate, 1,6-hexanediol dimethacrylate, and tetrahydrofurfuryl methacrylate.

2. A method for producing a cured product, comprising curing the curable composition according to claim 1 by irradiating it with active energy rays.

3. A method for producing a cured product, comprising curing the curable composition according to claim 1 by heating.

4. A cured product of the curable composition according to claim 1.

5. An adhesive comprising the curable composition according to claim 1.

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