JP2018172494A - Curable composition, method for producing cured product, cured product thereof, and adhesive using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a curable composition which has low viscosity and gives a cured product having excellent adhesion, a method for producing a cured product, a cured product of the curable composition, and an adhesive using the curable composition.SOLUTION: The curable composition contains a cationically polymerizable monomer (A), a cationic polymerization initiator (B), and a polymer (C) having a cationically polymerizable substituent. The curable composition contains, based on 100 pts.mass of the total of the cationically polymerizable monomer (A) and the polymer (C) having a cationically polymerizable substituent, 0.001-15 pts.mass of the cationic polymerization initiator (B) and 1-20 pts.mass of the polymer (C) having a cationically polymerizable substituent. The polymer (C) having a cationically polymerizable substituent contains a polymer (C1) having a weight-average molecular weight of 1,000-9,000 and a polymer (C2) having a weight-average molecular weight of 10,000-300,000 as essential components.SELECTED DRAWING: None

Description

  The present invention relates to a curable composition, a method for producing a cured product, the cured product, and an adhesive using the curable composition. Specifically, the curable composition has 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 various curable compositions containing a polymer have been proposed.

  For example, Patent Document 1 proposes an optical film adhesive that has good wettability to a polarizer and a protective film, can be applied to a thin film, and does not cause turbidity of coating liquid due to the wetting agent or adhesion inhibition. Has been. Patent Document 2 proposes a cationically polymerizable composition that is excellent in coatability, curability and adhesiveness. Patent Document 3 proposes a curable composition useful as an adhesive for bonding a transparent plastic substrate, a material for forming a thin light guide plate used in a backlight device constituting a liquid crystal display device, and the like.

JP 2012-172026 A JP 2017-008165 A International Publication No. 2015/163216

  However, the curable compositions as proposed in these Patent Documents 1 to 3 are not necessarily sufficient in viscosity and adhesion of the cured product to the substrate, and the current situation is that further improvement is desired. .

  SUMMARY OF THE INVENTION 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. .

  As a result of intensive studies to solve the above problems, the present inventors have found that a composition having a predetermined composition can solve the above problems, and have completed the present invention.

That is, the curable composition of the present invention contains a cationic polymerizable monomer (A), a cationic polymerization initiator (B), and a polymer (C) having a cationic polymerizable substituent, and the cationic polymerizable monomer (A ) And the polymer (C) having the cationic polymerizable substituent is 100 parts by mass, and has 0.001 to 15 parts by mass of the cationic polymerization initiator (B) and the cationic polymerizable substituent. 1 to 20 parts by mass of the polymer (C),
The polymer (C) having the cationic polymerizable substituent is essential for a polymer (C1) having a weight average molecular weight of 1,000 to 9,000 and a polymer (C2) having a weight average molecular weight of 10,000 to 300,000. It is characterized by being a component.

  In the curable composition of the present invention, the cationic polymerizable monomer (A) is preferably composed mainly of an aromatic epoxy compound (A1). Here, the main component means a mixture of several types of cationically polymerizable monomers (A) and having the largest total of the same types of cationically polymerizable monomers.

  Moreover, the manufacturing method of the hardened | cured material of this invention hardens the curable composition of this invention by irradiating an active energy ray, or makes it harden | cure by heating.

  Furthermore, the cured product of the present invention is characterized by comprising the curable composition of the present invention.

  Furthermore, the adhesive of the present invention is characterized by comprising the curable composition of the present invention.

  According to 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.

Hereinafter, the curable composition of the present invention will be described in detail.
The curable composition of the present invention is a curable composition containing a cationic polymerizable monomer (A), a cationic polymerization initiator (B), and a polymer (C) having a cationic polymerizable substituent, and is cationically polymerizable. The total of the monomer (A) and the polymer (C) having a cationic polymerizable substituent is 100 parts by mass, the cationic polymerization initiator (B) is 0.001 to 15 parts by mass, and the polymer having a cationic polymerizable substituent (C) 1-20 mass parts is contained. In the curable composition of the present invention, the polymer (C) having a cationic polymerizable substituent is a polymer (C1) having a weight average molecular weight of 1,000 to 9,000, and a weight average molecular weight of 10,000 to 300,000. The polymer (C2) of 000 is an essential component. By setting it as such a composition, it becomes a curable composition with a low viscosity and the hardened | cured material excellent in adhesiveness.

  The cationically polymerizable monomer (A) used in the present invention is a compound that is polymerized or undergoes a crosslinking reaction by a cationic polymerization initiator activated by energy ray irradiation or heating. In the curable composition of the present invention, the cationic polymerizable monomer (A) includes an aromatic epoxy compound (A1), an aliphatic epoxy compound (A2), an alicyclic epoxy compound (A3), and an oxetane compound (A4). , Vinyl ether compound (A5) and the like can be used.

  The aromatic epoxy compound (A1) refers to an epoxy compound containing an aromatic ring. Specific examples of the aromatic epoxy compound (A1) include monofunctional aromatic epoxy compounds, phenol compounds such as phenol, cresol, and butylphenol, or monoglycidyl ethers of alkylene oxide adducts thereof; resorcinol, hydroquinone, catechol, and the like. Monoglycidyl etherified products of aromatic compounds having the above phenolic hydroxyl groups; Monoglycidyl etherified products of aromatic compounds having two or more alcoholic hydroxyl groups such as phenyldimethanol, phenyldiethanol, phenyldibutanol; phthalic acid, terephthalic acid Monoglycidyl ester of polybasic aromatic compound having two or more carboxylic acids such as trimellitic acid; glycidyl ester of benzoic acid, monoepoxy of styrene oxide or divinylbenzene Shi monster, and the like.

  Polyfunctional aromatic epoxy compounds include polyglycidyl etherified products of polyhydric phenols having at least one aromatic ring such as bisphenol A and bisphenol F or alkylene oxide adducts thereof; epoxy novolac resins; resorcinol, hydroquinone, catechol, etc. A polyglycidyl etherified product of an aromatic compound having two or more phenolic hydroxyl groups; a polyglycidyl etherified product of an aromatic compound having two or more alcoholic hydroxyl groups such as phenyldimethanol, phenyldiethanol or phenyldibutanol; phthalic acid And polyglycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids such as terephthalic acid and trimellitic acid; and diepoxidized products of divinylbenzene. As the aromatic epoxy compound (A1), a polyfunctional one is preferable because of its excellent curability.

  As the aromatic epoxy compound (A1), 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, 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 Manufactured by 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 (East YX8800 (manufactured by Mitsubishi Chemical Corporation); Marproof G-0105SA, Marproof G-0130SP (manufactured by NOF Corporation); Epicron N-665, Epicron HP-7200 (manufactured by Kasei Co., Ltd.) Manufactured by DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (Nipponization) Adeka Resin EP-4000, Adeka Resin EP-4005, Adeka Resin EP-4100, Adeka Resin EP-4901 (manufactured by ADEKA); TECHMORE VG-3101L (manufactured by Printec Co., Ltd.), etc. Is mentioned.

  The aromatic epoxy compound (A1) is 30 to 80 parts by weight, particularly 40 to 70 parts by weight, based on 100 parts by weight of the cationic polymerizable monomer (A). The aromatic epoxy compound (A1) is preferably the main component of the cationic polymerizable monomer (A).

  The aliphatic epoxy compound (A2) refers to an epoxy compound that is not classified into the above-described aromatic epoxy compound (A1) or the alicyclic epoxy compound (A3) described later. Specific examples of the aliphatic epoxy compound (A2) 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 allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, C12-13 mixed alkyl glycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl Polyglycol diglycidyl ether, 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, etc. Glycidyl ether of alcohol and aliphatic such as propylene glycol, trimethylolpropane, glycerin Polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides to polyhydric alcohols include diglycidyl esters of aliphatic long-chain dibasic acids. Furthermore, monoglycidyl ethers of higher aliphatic alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxy stearate, butyl epoxy stearate, epoxidized soybean oil, epoxidized polybutadiene and the like.

  As the aliphatic epoxy compound (A2), a glycidyl etherified product of an aliphatic alcohol or a polyglycidyl etherified product of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof is preferable because the viscosity, coatability and reactivity are improved.

  As the aliphatic epoxy compound (A2), 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-841, Denacol E -861, Denacol EX-911, Denacol EX-941, Denacol EX-920, Denacol EX-931 (manufactured by Nagase ChemteX Corporation); Epolite M-1230, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 400E, Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP, Epolite 1600, Epolite 80MF, Epolite 100MF (manufactured by Kyoeisha Chemical Co., Ltd.), Adeka Glycilol ED-503, Adeka Glycilol ED-503G, Adeka Glycilol ED-506 , Adekaglycilol ED-523T (manufactured by ADEKA Corporation) and the like.

  The viscosity, coating property, and reactivity of the aliphatic epoxy compound (A2) are 1 to 95 parts by mass, particularly 30 to 95 parts by mass with respect to 100 parts by mass of the cationic polymerizable monomer (A). Therefore, it is preferable.

  The alicyclic epoxy compound (A3) refers to a compound in which an oxirane ring is directly bonded to a saturated ring without a spacer. Specific examples of the alicyclic epoxy compound (A3) 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. For example, hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexane Ruboxylate, methylenebis (3,4-epoxycyclohexane), propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis (3,4-epoxycyclohexyl) propane, dicyclopentadiene diepoxide , Ethylenebis (3,4-epoxycyclohexanecarboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy Examples include 2-epoxyethylcyclohexane, α-pinene oxide, limonene dioxide and the like.

  Examples of the alicyclic epoxy compound (A3) include hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, or 3,4-epoxy-1-methylcyclohexyl-3,4. -Epoxy-1-methylhexanecarboxylate is preferable from the viewpoint of improving adhesion.

  A commercially available product can be used as the alicyclic epoxy compound (A3), and examples thereof include Celoxide 2021P, Celoxide 2081, Celoxide 2000, and Celoxide 3000 (manufactured by Daicel Corporation).

  The alicyclic epoxy compound (A3) is 0 to 20 parts by mass, particularly 0 to 10 parts by mass, with respect to 100 parts by mass of the cationic polymerizable monomer (A), and the viscosity, coatability and reactivity are improved. This is preferable.

  Examples of the oxetane compound (A4) 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-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, , 6-bis (3-ethyl-3-oxetanylmethoxy) hexane and other bifunctional aliphatic oxetas Compound, 3-ethyl-3-[(phenoxy) methyl] oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3 And monofunctional oxetane compounds such as-(hydroxymethyl) oxetane and 3-ethyl-3- (chloromethyl) oxetane. These can be used singly or in combination of two or more, and a polyfunctional oxetane compound is preferable because the curability and adhesion of the cured product are increased.

  A commercially available product can be used as the oxetane compound (A4). For example, Aron oxetane OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212 (Toagosei Co., Ltd.) Co., Ltd.), Etanacol OXBP, OXTP (manufactured by Ube Industries, Ltd.) and the like.

  It is preferable that the oxetane compound (A4) is 1 to 50 parts by weight, particularly 10 to 30 parts by weight with respect to 100 parts by weight of the cationic polymerizable monomer (A), because the viscosity, coatability and reactivity are improved. .

  Examples of the vinyl ether compound (A5) include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, Examples include 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether, and the like.

The cationic polymerization initiator (B) according to the curable composition of the present invention may be any compound as long as it can release a substance that initiates cationic polymerization by energy ray irradiation or heating. Preferably, it is a double salt that is an onium salt that releases a Lewis acid upon irradiation with energy rays, or a derivative thereof. Representative examples of such compounds include the following general formula:
[A] ^{r +} [B] ^r-
And cation and anion salts represented by the formula:

Here, the cation [A] ^{r +} is preferably onium, and the structure thereof is, for example, the following general formula:
[(R ¹ ) _a Q] ^{r +}
Can be expressed as

Further, R ¹ is an organic group having ¹ to 60 carbon atoms and optionally containing any number of atoms other than carbon atoms. a is an integer of 1 to 5. The a R ^{1 s} are independent and may be the same or different. Further, at least one is preferably an organic group as described above having an aromatic ring. 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. Further, when the valence of Q in the cation [A] ^{r +} is q, it is necessary that the relationship r = a−q is established (however, N = N is treated as a valence of 0).

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

Here, L is a metal or metalloid which is a central atom of a halide complex, and 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 3-7. Further, when the valence of L in the anion [B] ^r− is p, it is necessary that the relationship r = b−p holds.

Specific examples of the anion [LY _b ] ^{r— in} the above general formula include halogen ion, perchlorate ion (ClO ₄ ) ⁻ , tetrafluoroborate ion (BF ₄ ) ⁻ , hexafluorophosphate ion (PF ₆ ). ^-, hexafluoroantimonate _(SbF 6) ^-, hexafluoroarsenate _(AsF 6) ^-, hexachloroantimonate (SbCl ₆₎ ^- such as an inorganic ion; trifluoromethanesulfonate ion, methanesulfonate ion, butane sulfonic acid ions , 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 boric acid ion, tetrakis (pentafluorophenyl) boric acid ion; methanecarboxylic acid ion, ethanecarboxylic acid ion, propanecarboxylic acid ion, butanecarboxylic acid ion, octanecarboxylic acid ion, trifluoromethanecarboxylic acid Carboxylate ions such as acid ion, benzenecarboxylate ion, p-toluenecarboxylate ion; trifluoromethyl sulfite ion (CF ₃ SO ₃ ) ⁻ , methyl sulfate ion (CH ₃ OSO ₃ ) ⁻ , bis (trifluoromethanesulfonyl) Imido ion, tris (trifluoromethanesulfonyl) methide ion, (CF ₃ CF ₂ ) ₃ PF ₃ ⁻ , ((CF ₃ ) ₂ C ₆ H ₃ ) ₄ B ⁻ , (C ₆ F ₅ ) ₄ Ga ⁻ , ((CF ₃ ) ₂ C ₆ In addition to H ₃ ) ₄ Ga ^— , those selected from the following group can be mentioned.

Further, 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 ) ⁻ , trifluoromethyl sulfite 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.

  In the present invention, among these onium salts, it is particularly effective to use the following aromatic onium salts (a) to (c). Among these, one of them can be used alone, or two or more of them can be mixed and used.

  (I) Aryl diazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate

  (B) Diaryls such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, and tricumyliodonium tetrakis (pentafluorophenyl) borate Iodonium salt

  (C) sulfonium salts such as sulfonium cations and hexafluoroantimony ions, hexafluorophosphate ions, tetrakis (pentafluorophenyl) borate ions represented by the following group I or group II

<Group I>

<Group II>

Other preferable examples include (η ⁵ -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η)-(1-methylethyl) benzene] -iron. -Iron-arene complexes such as hexafluorophosphate, aluminum complexes such as tris (acetylacetonato) aluminum, tris (ethylacetonatoacetato) aluminum, tris (salicylaldehyde) aluminum and silanols such as triphenylsilanol A mixture of thiophenium, thioranium, benzylammonium, pyridinium, hydrazinium, and the like; polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, tetraethylenepentamine; 1,2-diaminocyclohexane, 1,4-diamino -3,6-di Cycloaliphatic polyamines such as tilcyclohexane and isophoronediamine; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone; the above polyamines, phenylglycidyl ether, butylglycidyl ether, bisphenol A-diglycidyl Polyepoxy addition-modified products produced by reacting various epoxy resins such as ethers, glycidyl ethers such as bisphenol F-diglycidyl ether or glycidyl esters of carboxylic acids; the above organic polyamines and phthalates An amidation-modified product produced by reacting a carboxylic acid such as acid, isophthalic acid or dimer acid by a conventional method; Mannich-modified products produced by reacting phenols having at least one aldehyde-reactive site with nuclei such as diol, cresol, xylenol, tert-butylphenol, and resorcin; 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-methyl Aliphatic dicarboxylic acids such as pentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer acid, dimer acid; phthalic acid, terephthalic acid, isophthalic acid Aromatic dicarboxylic acids such as acid and naphthalenedicarboxylic acid; cyclohexanedicarboxylic acid Alicyclic dicarboxylic acids such as: trimellitic acid, trimesic acid, trimeric acid such as trimer of castor oil fatty acid; tetracarboxylic acids such as pyromellitic acid] acid anhydrides; dicyandiamide, imidazoles, carboxylic acid ester, sulfone Examples include acid esters and amine imides.

  Among these, it is preferable to use an aromatic iodonium salt, an aromatic sulfonium salt, or an iron-arene complex 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 (B ) It is more preferable to contain at least 0.1% by mass with respect to 100% by mass.

  In the curable composition of the present invention, the proportion of the cationic polymerization initiator (B) used is 100 parts by mass in total of the cationic polymerizable monomer (A) and the polymer (C) having a cationic polymerizable substituent. The cationic polymerization initiator (B) is 0.001 to 15 parts by mass, preferably 0.1 to 10 parts by mass. If the amount is too small, curing tends to be insufficient, and if the amount is too large, various physical properties such as the water absorption rate and the strength of the cured product may be adversely affected.

  The polymer (C) having a cationic polymerizable substituent (hereinafter also referred to as “polymer (C)”) is not particularly limited in the backbone of the main chain as long as it has a cationic polymerizable substituent in the side chain. Those obtained by homopolymerizing or copolymerizing a compound having an ethylenically unsaturated bond are preferred. The cationically polymerizable substituent represents an epoxy group or an oxetane group. Examples of the polymer (C) include a polymer (C1) having a weight average molecular weight of 1,000 to 9,000 (hereinafter also referred to as “polymer (C1)”) and a polymer having a weight average molecular weight of 10,000 to 300,000 ( C2) (hereinafter also referred to as “polymer (C2)”) is an essential component.

  As the polymer (C), those obtained by monopolymerizing monomers represented by the following general formula (I), those obtained by copolymerizing a plurality of monomers represented by the following general formula (I), and the following general formula Monomerized monomer represented by (II), copolymerized plural monomers represented by the following general formula (II), monomer represented by the following general formula (I) And those obtained by copolymerizing monomers represented by the following general formula (II).

ここで、一般式（Ｉ）中、Ｘは、炭素原子数１〜７のアルキル基、炭素原子数１〜７のアルコキシ基、炭素原子数６〜１２のアリール基、炭素原子数６〜１２のアリールオキシ基もしくは炭素原子数６〜１０の脂環式炭化水素基、またはこれらの基中の水素原子が、エポキシ基、オキセタン基、水酸基およびカルボキシル基からなる群より選択される１種以上の基で置換されたものである。

Here, in general formula (I), 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, or an alkyl group having 6 to 12 carbon atoms. An aryloxy group or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, or one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group as the hydrogen atom in these groups Is replaced with.

ここで、一般式（ＩＩ）中、Ｒ^２は、水素原子、メチル基またはハロゲン原子を表し、Ｘ’は、炭素原子数１〜７のアルキル基、炭素原子数６〜１２のアリール基もしくは炭素原子数６〜１０の脂環式炭化水素基、またはこれらの基中の水素原子が、エポキシ基、オキセタン基、水酸基およびカルボキシル基からなる群より選択される１種以上の基で置換されたものである。

Here, in the general formula (II), R ² 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 carbon. An alicyclic hydrocarbon group having 6 to 10 atoms, or a hydrogen atom in these groups substituted with one or more groups selected from the group consisting of epoxy groups, oxetane groups, hydroxyl groups and carboxyl groups It is.

  Examples of the alkyl group having 1 to 7 carbon atoms represented by X in the general formula (I) include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, Examples include iso-amyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl and the like. Among these, an alkyl group having 1 to 4 carbon atoms, or 1 to 1 carbon atoms partially 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 4 alkyl groups are preferable from the viewpoint of curability.

  Examples of the alkoxy group having 1 to 7 carbon atoms represented by X in the general formula (I) include methoxy, ethoxy, propyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, Amyloxy, iso-amyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, and tert-heptyloxy. Among these, an alkyl group having 1 to 4 carbon atoms, or 1 to 1 carbon atoms partially 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 4 alkoxy groups are preferred from the viewpoint of curability.

  Examples of the aryl group having 6 to 12 carbon atoms represented by X in the general formula (I) include phenyl, methylphenyl, naphthyl and the like.

  Examples of the aryloxy group having 6 to 12 carbon atoms represented by X in the general formula (I) include phenyloxy, methylphenyloxy, naphthyloxy and the like.

  Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms represented by X in the general formula (I) include cyclohexyl, methylcyclohexyl, norbornyl, bicyclopentyl, bicyclooctyl, trimethylbicycloheptyl, and tricyclooctyl. , Tricyclodecanyl, spirooctyl, spirobicyclopentyl, adamantyl, isobornyl and the like.

  In the general formula (I), when a part of X is substituted with an epoxy group or an oxetane group, examples of the monomer represented by the general formula (I) include the following formulas (1) to (3): The monomer represented by this is mentioned.

ここで、式（１）中、Ｒ^３は、水素原子または炭素原子数１〜６のアルキル基を表し、ｍは、１〜６の整数である。

Here, in Formula (1), R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and m is an integer of 1 to 6.

ここで、式（２）中、Ｒ^４は、水素原子または炭素原子数１〜６のアルキル基を表し、ｎは、１〜６の整数である。

Here, in formula (2), R ⁴ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6.

式（３）中、Ｒ^５は、水素原子または炭素原子数１〜６のアルキル基を表し、ｓは、１〜６の整数である。

In formula (3), R ⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and s is an integer of 1 to 6.

In the general formula (II), examples of the halogen atom represented by R ² include fluorine, chlorine, bromine and iodine. In addition, the alkyl group having 1 to 7 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the alicyclic hydrocarbon group having 6 to 10 carbon atoms as X ′ is the same as in the above formula (I). Can be mentioned.

  In the general formula (II), when a part of X ′ is substituted with an epoxy group or an oxetane group, the monomer represented by the general formula (II) includes the following formulas (4) to (6): The thing represented by is mentioned.

ここで、式（４）中、Ｒ^２は、一般式（ＩＩ）と同じであり、Ｒ^６は、水素原子または炭素原子数１〜６のアルキル基を表し、ｔは、１〜６の整数である。

Here, in the formula (4), R ² is the same as in the general formula (II), R ⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and t is an integer of 1 to 6 It is.

ここで、式（５）中、Ｒ^２は、一般式（ＩＩ）と同じであり、Ｒ^７は、水素原子または炭素原子数１〜６のアルキル基を表し、ｑは、１〜６の整数である。

Here, in the formula (5), R ² is the same as in the general formula (II), R ⁷ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and q is an integer of 1 to 6 It is.

ここで、式（６）中、Ｒ^２は、一般式（ＩＩ）と同じであり、Ｒ^８は、水素原子または炭素原子数１〜６のアルキル基を表し、ｙは、１〜６の整数である。

Here, in formula (6), R ² is the same as in general formula (II), R ⁸ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and y is an integer of 1 to 6 It is.

  In the polymer (C), the proportion of the monomer constituting the polymer (C) is such that X 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. Represented by the above (I) or (II) in the case of 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. It is preferable to use the monomer in an amount of 10 to 100% by mass with respect to the total of 100% by mass of the monomers constituting the polymer (C) because the adhesiveness is improved.

  In a total of 100 parts by mass of the cationically polymerizable monomer (A) and the polymer (C) having a cationically polymerizable substituent, the polymer (C) is 1 to 20 parts by mass in total, particularly 3 to 15 parts by mass. However, it is preferable because viscosity, coating property, and reactivity are improved. In the polymer (C), the ratio of the polymer (C1) to the polymer (C2) is polymer (C1): polymer (C2) = 3: 1 to 1: 3, which is compatible with both high adhesion and low viscosity. Therefore, it is preferable.

  If necessary, the curable composition of the present invention may further contain a sensitizer and / or a sensitization aid. The sensitizer is a compound that exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength indicated by the cationic polymerization initiator (B) and promotes the polymerization initiation reaction by the cationic polymerization initiator (B). The sensitization aid is a compound that further promotes the action of the sensitizer.

  Examples of the sensitizer and the sensitization aid include anthracene compounds and naphthalene compounds.

  Examples of the anthracene compound include those represented by the following formula (IIIa).

ここで、式（ＩＩＩａ）中、Ｒ^９およびＲ^１０は、各々独立に水素原子、炭素原子数１〜６のアルキル基または炭素原子数２〜１２のアルコキシアルキル基を表し、Ｒ^１１は水素原子または炭素原子数１〜６のアルキル基を表す。

Here, in formula (IIIa), R ⁹ and R ¹⁰ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms, and R ¹¹ is a hydrogen atom. Alternatively, it represents an alkyl group having 1 to 6 carbon atoms.

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

  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-methyl- or 2-ethyl-9,10-dimethoxyanthracene, 2-methyl- or 2-ethyl-9,10-diethoxyanthracene, 2-methyl- or 2- Ethyl-9,10-dipropoxyanthrace 2-methyl- or 2-ethyl-9,10-diisopropoxyanthracene, 2-methyl- or 2-ethyl-9,10-dibutoxyanthracene, 2-methyl- or 2-ethyl-9,10-dipentyl Examples include oxyanthracene, 2-methyl- or 2-ethyl-9,10-dihexyloxyanthracene.

  As a naphthalene-type compound, what is represented by the following Formula (IIIb) is mentioned, for example.

ここで、式（ＩＩＩｂ）中、Ｒ^１２およびＲ^１３は各々独立に炭素原子数１〜６のアルキル基を表す。

Here, in formula (IIIb), R ¹² and R ¹³ each independently represents an alkyl group having 1 to 6 carbon atoms.

  Specific examples of the naphthalene compound represented by the above formula (IIIb) include the following compounds.

  For example, 4-methoxy-1-naphthol, 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyloxy-1-naphthol, 1,4-dimethoxynaphthalene, Examples 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 monomer (A) is not particularly limited, and may be used at a generally normal use ratio within a range not impairing the object of the present invention. It is preferable from a viewpoint of sclerosis | hardenability improvement that it is 0.1-3 mass parts or more of each of a sensitizer and a sensitization adjuvant with respect to 100 mass parts of polymeric monomers (A).

  A silane coupling agent can be used for the curable composition of this invention as needed. Examples of 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, γ Epoxy functional alkoxysilanes such as glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N-β (aminoethyl) -γ Aminofunctional alkoxysilanes such as aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, mercaptofunctional alkoxysilanes such as γ-mercaptopropyltrimethoxysilane, titanium Titanium alkoxides such as tetraisopropoxide and titanium tetranormal butoxide, titanium chelates such as titanium dioctyloxybis (octylene glycolate), titanium diisopropoxybis (ethyl acetoacetate), zirconi Arm tetraacetyl acetonate, zirconium chelates such as zirconium tributoxy monoacetylacetonate, zirconium acylates such as zirconium tributoxy monostearate, an isocyanate silane such as methyl triisocyanate silane.

  Although the usage-amount of a silane coupling agent is not specifically limited, Usually, it is the range of 0.01-20 mass parts with respect to 100 mass parts of whole quantity of the solid substance in a curable composition.

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

  In the curable composition of the present invention, a solvent that can dissolve or disperse the components (A), (B), and (C) that are usually used without any particular limitation can be used. For example, methyl ethyl ketone, methyl Ketones such as amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol Ether solvents such as monomethyl ether and dipropylene glycol dimethyl ether; 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 tylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol mono Ether ester solvents such as ethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate; benzene, toluene, xylene, etc. BTX solvents; aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; tellurium such as turpentine oil, D-limonene and pinene Hydrocarbon oils; paraffinic solvents such as mineral spirits, Swazol # 310 (Cosmo Matsuyama Petroleum), Solvesso # 100 (Exxon Chemical); carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2-dichloroethane, etc. Halogenated aliphatic hydrocarbon solvents such as: halogenated aromatic hydrocarbon solvents such as chlorobenzene; propylene carbonate, carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide , N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water and the like, and these solvents can be used as one or a mixture of two or more.

  In the curable composition of the present invention, 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.

  In the curable composition of the present invention, if necessary, 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. In addition, a compound exhibiting ultraviolet absorbing ability can also be used.

  In addition, as long as the effect of the present invention is not impaired, a radical polymerizable monomer, a radical polymerization initiator, a polyol, an inorganic filler, an organic filler, a pigment, a colorant such as a dye, a dye, an antifoaming agent, a thickener, Surfactants, leveling agents, flame retardants, thixotropic agents, diluents, plasticizers, stabilizers, polymerization inhibitors, UV absorbers, antioxidants, antistatic agents, flow regulators, adhesion promoters, etc. Various resin additives and the like can be added.

  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 types of printing, and immersion. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base | substrate, There is no restriction | limiting in the application method.

  The material for the support substrate is not particularly limited and those usually used can be used. For example, 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. Reolefins; Vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; Acrylic resins such as polymethyl methacrylate and polyacrylate; Polycarbonate; Polysulfone; Polyethersulfone; Polyetherketone; Polyetherimide; Polyoxyethylene , Polymer materials such as norbornene resin and cycloolefin polymer (COP).

  The support substrate may be subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, and laser treatment.

  In the method of curing the curable composition of the present invention by irradiation with energy rays, examples of energy rays include ultraviolet rays, electron beams, X-rays, radiation, high frequencies, and the like, and ultraviolet rays are most preferable economically. Examples of the ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp.

  The conditions in the method of curing the curable composition of the present invention by heating are 70 to 250 ° C. and 1 to 100 minutes. After 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 blending 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. Then, in order to cure the coating film, a cured film can be obtained by heat treatment at 180 to 250 ° C., preferably 200 to 250 ° C., for 30 to 90 minutes for an oven and 5 to 30 minutes for a hot plate.

  Specific applications of the 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, Fresnellen used for screen of projection TV, etc. A lens, a lens part of a lens sheet such as a lenticular lens sheet, or a backlight using such a sheet, an optical lens such as a microlens, an optical element, an optical connector, an optical waveguide, an optical molding casting agent, etc. Can be mentioned.

  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 The film which consists of hardened | cured material of this invention can be used for each layer.

  Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples. In Examples and Comparative Examples, “part” means “part by mass”.

[Examples 1 to 9, Comparative Examples 1 to 4]
Each component was fully mixed by the mixing | blending shown to the following [Table 1]-[Table 2], and the curable composition of Examples 1-9 and Comparative Examples 1-4 was obtained. About each obtained curable composition, the evaluation regarding a viscosity and adhesiveness was performed according to the following procedure.

(viscosity)
About each obtained curable composition, the viscosity was measured using the Toki Sangyo Co., Ltd. product E-type viscosity meter TVE-25L. The obtained results are also shown in [Table 1] to [Table 2].

(Adhesion)
Each obtained curable composition was applied to one acrylic film (Sumitomo Chemical Co., Ltd .: Technoloy 125S001) subjected to corona discharge treatment, and then subjected to another corona discharge treatment COP ( Cycloolefin polymer, manufactured by Nippon Zeon Co., Ltd .: Product No. ZEONOR Film 14-060) A film and a laminator were used for bonding, and an electrodeless ultraviolet lamp was used to irradiate light equivalent to 1000 mJ / cm ² through the COP film. And bonded to obtain a test piece. About the obtained test piece, the 90 degree | times peel test was done. Evaluation was performed according to the following criteria. The obtained results are also shown in [Table 1] to [Table 2].
(Double-circle): It is more than 2.5N / 2.5cm and shows the adhesive force which destroys a base material.
A: Adhesive force exceeding 2.5 N / 2.5 cm is shown, but the substrate is not destroyed.
(Triangle | delta): The adhesive force of 1.5-2.5N / 2.5cm is shown.
X: Adhesive strength of less than 1.5 N / 2.5 cm.

The following compounds A1-1 to A1-5, A2-1 to A2-2, A3-1 and A4-1 were used as the cationic polymerizable monomer (A).
Compound A1-1: EP-4100 (bisphenol A type diglycidyl ether: manufactured by ADEKA Corporation)
Compound A1-2: Adeka Resin EP-4901 (Bisphenol F type polyfunctional epoxy: manufactured by ADEKA Corporation)
Compound A1-3: R710 (bisphenol E type glycidyl ether: manufactured by Printec Co., Ltd.)
Compound A1-4: 2-phenoxyisopropyl glycidyl ether compound A1-5: Adekaglycilol ED-509S (monofunctional aromatic epoxy: manufactured by ADEKA Corporation)
Compound A2-1: 1,4-butanediol diglycidyl ether compound A2-2: Neopentyl glycol diglycidyl ether compound A3-1: Celoxide 2021P (alicyclic epoxy compound: manufactured by Daicel Corporation)
Compound A4-1: Aron oxetane OXT-221 (manufactured by Toagosei Co., Ltd.)

The following compound B-1 was used as the cationic polymerization initiator (B).
Compound B-1: 50% propylene carbonate solution of a mixture of two compounds represented by the following structure

As the polymer (C), the following compounds C1-1 to C1-2 and C2-1 to C2-5 were used.
Compound C1-1: copolymer of 70 parts by weight of methyl methacrylate and 30 parts by weight of glycidyl methacrylate (weight average molecular weight 7,000)
Compound C1-2: copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 4,000)
Compound C2-1: copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 10,000)
Compound C2-2: Copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 28,000)
Compound C2-3: Copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 38,000)
Compound C2-4: Copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 64,000)
Compound C2-5: copolymer of 70 parts by mass of methyl methacrylate and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 110,000)

From [Table 1] to [Table 2], it is clear that the curable composition of the present invention has a low viscosity and is excellent in the adhesion of the cured product.

Claims (6)

A polymer having a cationic polymerizable monomer (A), a cationic polymerization initiator (B), and a polymer (C) having a cationic polymerizable substituent, and having the cationic polymerizable monomer (A) and the cationic polymerizable substituent (C) is 100 parts by mass in total, and 0.001 to 15 parts by mass of the cationic polymerization initiator (B), and 1 to 20 parts by mass of the polymer (C) having the cationic polymerizable substituent. ,
The polymer (C) having the cationic polymerizable substituent is essential for a polymer (C1) having a weight average molecular weight of 1,000 to 9,000 and a polymer (C2) having a weight average molecular weight of 10,000 to 300,000. A curable composition characterized by comprising a component.   The curable composition according to claim 1, wherein the cationic polymerizable monomer (A) comprises an aromatic epoxy compound (A1) as a main component.   A method for producing a cured product, wherein the curable composition according to claim 1 or 2 is cured by irradiation with active energy rays.   A method for producing a cured product, wherein the curable composition according to claim 1 or 2 is cured by heating.   A cured product comprising the curable composition according to claim 1. An adhesive comprising the curable composition according to claim 1 or 2.