KR20190022638A - CURING COMPOSITION, METHOD FOR PRODUCING CURED PRODUCT, AND CURED PRODUCT - Google Patents

Abstract

A curable composition which is excellent in adhesion of a cured product, a method for producing a cured product, and a cured product thereof.
A curable composition comprising 100 parts by mass of a cationic polymerizable component (A) and 1 to 10 parts by mass of a cationic polymerization initiator (B), wherein the cationic polymerizable component (A) comprises an aromatic epoxy compound (A1) (A3) and a polymer (A4) having a cationic polymerizable substituent and a weight average molecular weight of 1,000 to 30,000 as an essential component, wherein the aromatic epoxy compound (A1) is a cationic polymerizable component A), and contains a polyfunctional aromatic epoxy compound and a monofunctional aromatic epoxy compound.

Description

CURING COMPOSITION, METHOD FOR PRODUCING CURED PRODUCT, AND CURED PRODUCT

 The present invention relates to a curable composition, a method for producing a cured product, and a cured product thereof, and more particularly, to a curable composition having excellent adhesion to a cured product, a method for producing the cured product, and a cured product thereof.

Curable compositions are used in the fields of inks, paints, various coatings, adhesives, optical members and the like. Various improvements have been reported on the improvement of the curable composition.

 For example, in Patent Documents 1 to 4, various photo-curable adhesives have been proposed. Specifically, in Patent Document 1, a polyvinyl alcohol polarizer and various protective films can be adhered easily and firmly with the same photocuring adhesive, and a film having substantially no organic solvent and having excellent thin film applicability at low point A fire type adhesive has been proposed. Patent Document 2 proposes a photo-curable epoxy resin-based adhesive which does not need to be irradiated with light of very high roughness or heated after light irradiation. Patent Document 3 proposes a photo-curable adhesive which is excellent in storage stability, can suppress discoloration of the adhesive itself and the object to be cured at the time of curing, has a high curing speed and provides good adhesiveness. Patent Document 4 proposes a cationic polymerizable composition excellent in curability, adhesive property and water resistance, and excellent in use for an adhesive.

Japanese Patent Application Laid-Open No. 2011-236389 Japanese Laid-Open Patent Publication No. 2012-149262 International Publication No. 2008/111584 International Publication No. 2015/005211

However, even in the case of the adhesives proposed in Patent Documents 1 to 4, the adhesiveness of the cured product is not necessarily satisfactory, and furthermore, the adhesion of the cured product is required to be further investigated.

Accordingly, an object of the present invention is to provide a curable composition which is excellent in adhesion of a cured product, a method for producing a cured product, and a cured product thereof.

DISCLOSURE OF THE INVENTION The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, discovered that a curable composition having a specific composition can solve the above problems, and have completed the present invention.

That is, the curable composition of the present invention is a curable composition containing 100 parts by mass of the cationic polymerizable component (A) and 1 to 10 parts by mass of the cationic polymerization initiator (B)

Wherein the cationic polymerizable component (A) comprises an aromatic epoxy compound (A1), an aliphatic glycidyl compound (A2), an oxetane compound (A3), a polymer having a cationic polymerizable substituent and a weight average molecular weight of 1,000 to 30,000 (A) is an essential component, and the aromatic epoxy compound (A1) is a main component of the cationic polymerizable component (A), and contains a polyfunctional aromatic epoxy compound and a monofunctional aromatic epoxy compound.

In the curable composition of the present invention, it is preferable to further contain an alicyclic epoxy compound (A5) as the cationic polymerizable component (A). Further, in the curable composition of the present invention, the oxetane compound (A3) is preferably a polyfunctional oxetane compound.

The method for producing a cured product of the present invention is characterized in that the curable composition of the present invention is irradiated with an active energy ray or heated.

The cured product of the present invention is a cured product of the curable composition of the present invention.

According to the present invention, it is possible to provide a curable composition having excellent adhesiveness to a cured product, a method for producing a cured product, and a cured product thereof. The curable composition of the present invention is useful for an adhesive, particularly an adhesive for a polarizing plate.

Hereinafter, the curable composition of the present invention will be described in detail. The curable composition of the present invention causes polymerization or crosslinking reaction by a cationic polymerization initiator activated by energy ray irradiation or heating and comprises 100 parts by mass of the cationic polymerizable component (A) and 100 parts by mass of the cationic polymerization initiator (B) 1 To 10 parts by mass. In the curable composition of the present invention, the cationic polymerizable component (A) is at least one compound selected from the group consisting of an aromatic epoxy compound (A1), an aliphatic glycidyl compound (A2), an oxetane compound (A3) (A4) having an average molecular weight of 1,000 to 30,000 as an essential component, and the aromatic epoxy compound (A1) is a main component of the cationic polymerizable component (A). In addition, alicyclic epoxy compound (A5), vinyl ether compound (A6) and the like may be contained. Here, the main component refers to the case where several kinds of cationic polymerizable components are mixed and the total of the same kind of cationic polymerizable components is the largest.

The aromatic epoxy compound (A1) refers to an epoxy compound containing an aromatic ring, and the curable composition of the present invention contains both a multifunctional aromatic epoxy compound and a monofunctional aromatic epoxy compound.

As the monofunctional aromatic epoxy compound, a monoglycidyl ether of a phenol compound such as phenol, cresol, butylphenol or an alkylene oxide adduct thereof; Monoglycidyl ether compounds of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone and catechol; Monoglycidyl ether compounds of aromatic compounds having two or more alcoholic hydroxyl groups such as phenyl dimethanol, phenyl diethanol and phenyl dibutanol; Monoglycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids such as phthalic acid, terephthalic acid and trimellitic acid; Glycidyl esters of benzoic acid, monoepoxide of styrene oxide or divinylbenzene, and the like.

Examples of the polyfunctional aromatic epoxy compound include polyglycidyl ether compounds of polyhydric phenols or alkylene oxide adducts thereof having at least one aromatic ring such as bisphenol A and bisphenol F; Epoxy novolac resins; Polyglycidyl ether compounds of aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone and catechol; Polyglycidyl ether compounds of aromatic compounds having two or more alcoholic hydroxyl groups such as phenyl dimethanol, phenyl diethanol and phenyl dibutanol; Polyglycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids such as phthalic acid, terephthalic acid and trimellitic acid; And a diepoxide of divinylbenzene.

The ratio of the monofunctional aromatic epoxy compound to the monofunctional aromatic epoxy compound is preferably 20 to 50 parts by mass, particularly 30 to 40 parts by mass, based on 100 parts by mass of the polyfunctional aromatic epoxy compound, And in view of reactivity.

Examples of the aromatic epoxy compound (A1) include commercially available products such as Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711 Oncot EX-1010, Oncot EX-1011, Oncot EX-1010, Oncot EX-1010, Oncot EX-1010, Oncot EX-1011, Oncot EX- Coat 1012 (manufactured by Nagase ChemteX Corporation); Ogrosol PG-100, Oggol EG-200, Oggol EG-210, Oggol EG-250 (manufactured by Osaka Gas Chemical Co., Ltd.); HP4032, HP4032D, HP4700 (manufactured by DIC Corporation); ESN-475V (manufactured by Shin-Nitetsu Sumitomo Chemical Co., Ltd.); Epikote YX8800 (manufactured by Mitsubishi Kagaku Co., Ltd.); Mahurup G-0105SA, Mahuruf G-0130SP (manufactured by Nihon Oil Co., Ltd.); Epiclon N-665, Epiclon HP-7200 (manufactured by DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (Nippon Kayaku )); Adeka Resin EP-4001, Adeka Resin EP-4100, Adeka Resin EP-4901 (manufactured by ADEKA Corporation), Adeka Glycerol ED- Lt; / RTI > TECHMORE VG-3101L (manufactured by PRINTEC Co., Ltd.) and the like. The aromatic epoxy compound (A1) is preferably polyfunctional because it has excellent curability.

The aromatic epoxy compound (A1) is preferably 20 to 80 parts by mass, particularly 30 to 50 parts by mass, based on 100 parts by mass of the cationic polymerizable component (A), because the viscosity, coatability, reactivity and curability are improved. As described above, the main component is a mixture of several kinds of cationic polymerizable components and refers to the largest amount of cationic polymerizable components of the same kind.

The aliphatic glycidyl compound (A2) refers to an epoxy compound not classified as the above-mentioned aromatic epoxy compound (A1) or an alicyclic epoxy compound (A5) to be described later. Specific examples of the aliphatic glycidyl compound (A2) Polyfunctional epoxy compounds such as glycidyl ether compounds of alcohols and glycidyl esters of alkylcarboxylic acids, polyglycidyl ether compounds of aliphatic polyhydric alcohols or alkylene oxide adducts thereof, polyglycidyl ethers of aliphatic long chain polybasic acids And polyfunctional epoxy compounds such as epoxides and cidyl esters. 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 glycol diglycidyl ether, triglycidyl ether of glycerin, triglycidyl ether of trimethylol propane, tetraglycidyl ether of sorbitol, hexaglycidyl of dipentaerythritol Glycidyl ethers of polyhydric alcohols such as ethylene glycol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, and aliphatic polyhydric alcohols such as propylene glycol, trimethylol propane, and glycerin, Polyglycidyl ether of a polyether polyol obtained by adding an alkylene oxide of at least two carbon atoms, and diglycidyl ester of an aliphatic long chain dibasic acid have. Examples thereof include monoglycidyl ethers of aliphatic higher alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl stearate, octyl stearate, butyl stearate, epoxidized soybean oil and epoxidized polybutadiene.

As the aliphatic glycidyl 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 viscosity, applicability and reactivity are improved.

Examples of the aliphatic glycidyl compound (A2) include commercially available products such as Denacol EX-121, Denacol EX-171, Denacol EX-192, Denacol EX-211, Denacol EX- Denacol EX-411, Denacol EX-411, Denacol EX-421, Denacol EX-512, Denacol EX-521, Denacol EX-611, Denacol EX- Denacol EX-821, Denacol EX-811, Denacol EX-850, Denacol EX-851, Denacol EX-821, Denacol EX-812, Denacol EX- Denacol EX-930, Denacol EX-930, Denacol EX-930, Denacol EX-930, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, Denacol EX- Lt; / RTI > 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.), adekaglycylol ED-503, adekaglycylol ED-503G, adekaglycollol ED-506, adekaglycollol ED -523T, ADEKA RESIN EP-4088S, ADEKA RESIN EP-4080E (manufactured by ADEKA Corporation), and the like.

The amount of the aliphatic glycidyl compound (A2) is preferably 1 to 70 parts by mass, particularly 10 to 30 parts by mass, based on 100 parts by mass of the cationically curable component (A), since the viscosity, coating properties and reactivity are improved.

The oxetane compound (A3) contains either a polyfunctional oxetane compound in which two or more oxetanyl groups are contained in the same molecule and a monofunctional oxetane compound in which one oxetanyl group is contained in the same molecule. Examples of the oxetane compound (A3) include 3,7-bis (3-oxetanyl) -5-oxa-nonane, 1,4-bis [ 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-oxetanylmethoxy) butane and 1,6-bis (3-ethyl-3-oxetanylmethoxy) Ethyl-3- (hydroxymethyl) oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3- Cetane, and monofunctional oxetane compounds such as 3-ethyl-3- (chloromethyl) oxetane. These can be used singly or in combination of two or more kinds, and a polyfunctional oxetane compound is preferable because the curing property and adhesion of the cured product are enhanced.

As the oxetane compound (A3), a commercially available product can be used. Examples of the oxetane compound OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT- ), Ethanacol OXBP, OXTP (manufactured by Ube Industries, Ltd.), and the like.

The content of the oxetane compound (A3) is preferably from 1 to 70 parts by mass, particularly preferably from 10 to 40 parts by mass, based on 100 parts by mass of the cationically curable component (A), since viscosity, applicability and reactivity are improved.

(A4) (hereinafter also referred to as " polymer (A4) ") having a cationic polymerizable substituent and a weight average molecular weight of 1,000 to 30,000 has a cationically polymerizable substituent in the side chain, But it is preferable to polymerize or copolymerize the compound having an ethylenically unsaturated bond. The cationic polymerizable substituent refers to an epoxy group or an oxetane group.

Examples of the polymer (A4) include polymers obtained by polymerizing monomers represented by the following formula (I), copolymers of a plurality of monomers represented by the following formula (I), monomers represented by the following formula (II) A copolymer obtained by copolymerizing a plurality of monomers represented by the following formula (II), a copolymer of a monomer represented by the following formula (I) and a monomer represented by the following formula (II) .

Wherein X represents 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 aryloxy group having 6 to 10 carbon atoms An alicyclic hydrocarbon group or a hydrogen atom in these groups is substituted with at least one group selected from the group consisting of an epoxy group and an oxetane group.

In the formula, R ¹ is a hydrogen atom, a methyl group or a halogen atom, X 'is an alkyl group of 1 to 7 carbon atoms, carbon alicyclic hydrocarbon of 6 to 10 carbon atoms or an aryl group of 6 to 12 atoms of hydrogen group, Or hydrogen atoms in these groups are substituted with at least one group selected from the group consisting of an epoxy group and an oxetane group.

Examples of the alkyl group having 1 to 7 carbon atoms represented by X in the formula (I) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert- butyl, isobutyl, amyl, iso- Amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl and tert-heptyl. Among them, an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms which is partially substituted with at least one group selected from the group consisting of an epoxy group and an oxetane group is preferable from the viewpoint of curability.

Examples of the alkoxy group having 1 to 7 carbon atoms represented by X in the formula (I) include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, Amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2- , 3-heptyloxy, iso-heptyloxy, tert-heptyloxy and the like. Among them, an alkoxy group having 1 to 4 carbon atoms and partially substituted with at least one group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms or an epoxy group and an oxetane group is preferable from the viewpoint of curability.

Examples of the aryl group having 6 to 12 carbon atoms represented by X in the 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 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 formula (I) include cyclohexyl, methylcyclohexyl, norbornyl, bicyclopentyl, bicyclooctyl, trimethylbicycloheptyl, tricyclooctyl, Tricyclodecanyl, spirooctyl, spirobicyclenpentyl, adamantyl, isobornyl, and the like.

Examples of the monomer represented by the formula (I) in the case where a part of X in the formula (I) is substituted with an epoxy group or an oxetane group include those represented by the following formulas (1) to (3) There are monomers.

In the formula, R ² represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and m is an integer of 1 to 6.

In the formulas, R ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6.

In the formulas, R ⁴ 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 formula (II), examples of the halogen atom represented by R ¹ include fluorine, chlorine, bromine, iodine and the like.

Examples of the monomer represented by the formula (II) in the case where a part of X 'in the formula (II) is substituted with an epoxy group or an oxetane group include those represented by the following formulas (4) to (6) .

Wherein R ¹ is the same as in the formula (II), R ⁵ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and t is an integer of 1 to 6.

Wherein R ¹ is the same as in the formula (II), R ⁶ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and q is an integer of 1 to 6.

Wherein R ¹ is the same as in the formula (II), R ⁷ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and y is an integer of 1 to 6.

In the polymer (A4), the proportion of the monomer constituting the polymer is such that X is an alkyl group having 1 to 7 carbon atoms substituted with at least one group selected from the group consisting of an epoxy group and an oxetane group, (I) or (II) in the case of an aryl group having 1 to 12 carbon atoms or an alicyclic hydrocarbon group having 6 to 10 carbon atoms in an amount of 10 to 100 parts by mass based on 100 parts by mass of the total amount of the monomers constituting the polymer It is preferable to use it so as to be in a mass%, because adhesion is improved.

As the monomer constituting the polymer (A4), it is preferable to use an ethylenic unsaturated compound having a hydroxyl group or a carboxyl group in combination with the monomer represented by the formula (I) or (II) because adhesion is improved.

The amount of the polymer (A4) is preferably 1 to 20 parts by mass, particularly 3 to 10 parts by mass, based on 100 parts by mass of the cationically curable component (A), because the viscosity, coating property and reactivity are improved.

The alicyclic epoxy compound (A5) indicates that an oxirane ring is bonded directly to the prepolymer without passing through a bonding group. Specific examples of the alicyclic epoxy compound include polyglycidyl ethers of polyhydric alcohols having at least one alicyclic ring Cargo, cyclohexene oxide or cyclopentene oxide-containing compound obtained by epoxidizing cyclohexene or a cyclopentane ring-containing compound with an oxidizing agent. For example, 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, Epoxycyclohexylethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4- (3,4-epoxycyclohexylethyl) adipate, 3, 4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, (3,4-epoxycyclohexane), propane-2,2-diyl-bis (3,4-epoxycyclohexane), 2,2-bis Epoxycyclohexyl) propane, dicyclopentadiene diepoxide, ethylenebis (3,4-epoxycyclohexanecarboxylate), epoxyhexahydrophthalate dioctyl, epoxyhexahydrophthalic acid di-2-ethylhexyl , 1- Epoxy-3, 4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, alpha -pinene oxide, limonene dioxido and the like. Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate or 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy- The rate is preferable from the viewpoint of improving the adhesion.

As the alicyclic epoxy compound (A5), a commercially available product can be used. Examples of the alicyclic epoxy compound (A5) include Celloxide 2021P, Celloxide 2081, Celloxide 2000, and Celloxide 3000 (manufactured by Daicel Chemical Industries, Ltd.).

The alicyclic epoxy compound (A5) is preferably used in an amount of 0 to 30 parts by mass, particularly 0 to 20 parts by mass, based on 100 parts by mass of the cationically curable component (A), since viscosity, coating properties and reactivity are improved.

Examples of the vinyl ether compound (A6) include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 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, 1,6-cyclohexanedimethanol divinyl ether, and the like.

The cationic polymerization initiator (B) for the curable composition of the present invention may be any compound capable of releasing a substance that initiates cationic polymerization by energy ray irradiation or heating. Preferably, the cationic polymerization initiator (B) An onium salt which releases an acid, or a derivative thereof. Representative examples of such compounds include compounds represented by the following general formula,

[A] ^{r +} [B] ^r-

For example, salts of anions and cations represented by the following formulas.

Here, the cation [A] ^{r +} is preferably onium, and its structure is, for example,

[(R ⁸ ) _a Q] ^{r +}

As shown in FIG.

Here, R ⁸ is an organic group having 1 to 60 carbon atoms and may contain several atoms other than carbon atoms. and a is an integer of 1 to 5. a > R < ⁸ > are each independently of one another and may be the same or different. It is preferable that at least one of them is 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, When the valence of Q in the cation [A] ^{r +} is q, it is necessary that the relation r = aq is satisfied (note that N = N is treated as 0).

The negative ion [B] ^r- is preferably a halide complex, and its structure may be, for example,

[LY _b ] ^r-

As shown in FIG.

In addition, L is a metal or a metalloid, which is a central atom of a halide complex, and B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, , Mn, Co, and the like. Y is a halogen atom. b is an integer of 3 to 7; Further, when the valence of L in the anion [B] ^r- is p, it is necessary that the relation r = bp is established.

Specific examples of the anion [LY _b ] ^r- of the general formula include tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, tetrafluoroborate (BF ₄ ) ^- , hexafluorophosphate (PF ₆ ) ^- , hexafluoroantimonate (SbF ₆ ) ^- , hexafluoroarsenate (AsFF ₆ ) ^- and hexachloroantimonate (SbCl ₆ ) ^- have.

The anion [B] ^r- can be represented by the following general formula,

[LY _{b - 1} (OH)] ^{r -}

Can also be preferably used. L, Y, and b are the same as described above. Examples of other anions that can be used include perchlorate ion (ClO ₄ ) ^- , trifluoromethyl sulfite ion (CF ₃ SO ₃ ) ^- , fluorosulfonate ion (FSO ₃ ) ^- , toluenesulfonate anion, trinitrobenzenesulfonate anion , Camphorsulfonate, nonafluorobutanesulfonate, hexadecaprooctanesulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate, and the like.

In the curable composition of the present invention, among these onium salts, it is particularly effective to use the following (a) to (c) aromatic onium salts. Of these, one type may be used alone, or two or more types may be used in combination.

(A) aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, and 4-methylphenyldiazonium hexafluorophosphate;

(B) diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, tolyl cumyl iodonium tetrakis Diaryl iodonium salts such as pentafluorophenylborate

(C) Sulfonium cations represented by the following Group I or Group II: sulfonium cations such as hexafluoroantimony ion, hexafluorophosphate ion and tetrakis (pentafluorophenyl)

<Group I>

<Group II>

In addition, as other preferable examples, (侶⁵ -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η) - (1-methylethyl) benzene] (Acetylacetonato) aluminum, tris (ethylacetonatoacetato) aluminum, tris (salicylaldehydato) aluminum, etc., and triphenylsilanol And mixtures thereof; Thiophenium salts, thioronium salts, benzylammonium salts, pyridinium salts, hydrazinium salts and the like; Polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, 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; Glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, and bisphenol F-diglycidyl ether, glycidyl esters of carboxylic acid, etc. A polyepoxy addendum modified product prepared by reacting various epoxy resins by the conventional method; An amidated modified product prepared by reacting the above organic polyamines with carboxylic acids such as phthalic acid, isophthalic acid and dimeric acid by a conventional method; Aldehydes such as polyamines and formaldehyde, and phenols having at least one aldehyde-reactive site in nuclei such as phenol, cresol, xylenol, tert-butylphenol, resorcin and the like by a conventional method Mannichite Modified Water; Examples of the polyvalent carboxylic acid include polyvalent carboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, Aliphatic dicarboxylic acids such as adipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimer acid and dimeric acid; , Aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid and naphthalene dicarboxylic acid, alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid, tricarboxylic acids such as trimellitic acid, trimesic acid and trimer of castor oil fatty acid, Tetracarboxylic acids such as acetic acid and the like); Dicyandiamide, imidazoles, carboxylic acid esters, sulfonic acid esters, amine imides and the like.

Of these, aromatic iodoaluminum salts, aromatic sulfonium salts and iron-arene complexes are preferably used from the viewpoints of practical use and improvement of photosensitivity, and an aromatic sulfonium salt having the following structure is mixed with 100% by mass of the cationic polymerization initiator (B) By mass, more preferably at least 0.1% by mass or more.

In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom, a halogen atom, 10 represents an alkyl group, an alkoxy group or 2 to 10 carbon atoms, ester of 1 to 10 carbon atoms of, R ^21, R ^22, R ²³ and R ²⁴ are, each independently, a hydrogen atom, a halogen atom or 1 to carbon atoms, And R ²⁵ represents any one substituent selected from a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms or the following formulas (A) to (C), and An ^{q -} Represents an anion, and p represents a coefficient that makes the charge neutral.

Wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ ,

Each of R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ independently represents a hydrogen atom, a halogen atom, a carbon atom represents an alkoxy group or 2 to 10 carbon atoms in the ester alkyl groups of 1 to 10 atoms, carbon atoms, 1 to 10, R ^30, R ^31, R ^32, R ³³ and R ³⁴ are, each independently, represents a hydrogen atom, a halogen atom or an alkyl group of carbon atoms ^{1~10, R 11, R 12,} R 13, R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R The hydrogen atom of the group represented by R ²² , R ²³ , R ²⁴ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ is a halogen atom, a nitro group, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁵ , R ¹⁵ , R ¹⁵ and R ¹⁵ may be the same or different and are each independently a hydrogen atom, an alkyl group, an alkoxy group, R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ is selected from the group consisting of -O-, -CO-, -COO-, OCO-, -S-, -SO ₂ -, -SCO- or -COS-.

In the compound represented by formula ^{(1), R 11, R} 12, R 13, R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23 , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ Examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

^{R 11, R 12, R 13} , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 25, R 26, R 27 ^{, R 28, R 29, R} 30, R 31, R 32, R 33, R 34, R 35, R 36, R 37, the alkyl group of 1 to 10 carbon atoms represented by R ³⁸ and R ^39, methyl, And examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, Nonyl, decyl, isodecyl, and the like.

^{R 11, R 12, R 13} , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 26, R 27, R 28 Examples of the alkoxy group having 1 to 10 carbon atoms represented by R ²⁹ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ and R ³⁹ include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, Cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, tetrahydropyranyloxy, tetrahydropyranyloxy, tetrahydropyranyloxy, tetrahydrothiopyranyloxy, tetrahydrothiopyranyloxy, tetrahydrothiopyranyloxy, Methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxyethoxyethoxyethyloxy, 3-methoxybutyloxy, 2-methylthioethyloxy, trifluoromethyloxy, and the like.

^{R 11, R 12, R 13} , R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22, R 23, R 24, R 26, R 27, R 28 , R ²⁹ , R ³⁵ , R ³⁶ , R ³⁷ , R ^38, and R ³⁹ include an ester group having 2 to 10 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarb Such as methoxy, ethoxy, ethoxy, ethoxy, ethoxy, ethoxy, propoxy, isopropoxy, butoxy, .

The ratio of the cationic polymerization initiator (B) to the cationic polymerizable component (A) is 1 to 10 parts by mass, preferably 2 to 10 parts by mass, relative to 100 parts by mass of the cationic polymerizable component (A) To 8 parts by mass. If it is too small, curing tends to be insufficient, and if it is too much, there are cases where adverse effects are exerted on various physical properties such as the water absorption rate of the cured product and the cured product strength.

In the curable composition of the present invention, a sensitizer and / or a sensitizer may be used if necessary. The sensitizer is a compound which exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength exhibited by the cationic polymerization initiator (B) and promotes the polymerization initiation reaction by the cationic polymerization initiator (B). In addition, the sensitization assistant is a compound that further promotes the action of the sensitizer.

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

As the anthracene compound, for example, there is one represented by the following formula (7).

In the formula (7), R ⁵⁰ and R ⁵¹ 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, R ⁵² is a hydrogen atom, Lt; / RTI &gt;

Specific examples of the anthracene compound represented by the formula (7) include the following compounds.

For example, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-diisopropoxyanthracene, 9,10-dibutoxyanthracene, 9,10 Bis (2-methoxyethoxy) anthracene, 9,10-bis (2-ethoxyethoxy) anthracene, 9,10-bis (3-butoxypropoxy) anthracene, 2-methyl- or 2-ethyl-9,10-dimethoxyanthracene, 2- methyl- or 2- ethyl Diethoxy anthracene, 2-methyl- or 2-ethyl-9,10-dipropoxyanthracene, 2-methyl- or 2-ethyl-9,10-diisopropoxyanthracene, Or 2-ethyl-9,10-dibutoxyanthracene, 2-methyl- or 2-ethyl-9,10-dipentyloxyanthracene, 2- have.

Examples of the naphthalene-based compound include those represented by the following formula (8).

Here, in formula (8), R ⁵³ and R ⁵⁴ each independently represent an alkyl group having 1 to 6 carbon atoms.

Specific examples of the naphthalene-based compound represented by the formula (8) include the following compounds.

Naphthol, 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyloxy- 1,4-dimethoxynaphthalene, 1,4-dimethoxynaphthalene, 1-ethoxy-4-methoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-dipropoxynaphthalene and 1,4-dibutoxynaphthalene.

The ratio of the sensitizer and the sensitizer to the cationic polymerizable component (A) is not particularly limited and may be generally used within a range that does not impair the object of the present invention. For example, cationic polymerization From the viewpoint of improving the curability, it is preferable that each of the sensitizer and the sensitizer is added in an amount of 0.1 to 3 parts by weight based on 100 parts by weight of the component (A).

In the curable composition of the present invention, a silane coupling agent may be used if necessary. As the silane coupling agent, there may be mentioned, for example, dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyl Alkenyl functional alkoxysilanes such as vinyl trichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, and allyltrimethoxysilane, alkoxy functional alkoxysilanes such as trimethoxysilane, and 3-methacryloxypropyl tri Methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, Epoxyfunctional alkoxysilanes such as glycidoxypropyltrimethoxysilane,? -Glycidoxypropylmethyldiethoxysilane and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N-β (aminoethyl ) -γ-aminopropyl Amino functional alkoxy silanes such as trimethoxy silane, dimethoxy silane, γ-aminopropyl triethoxy silane and N-phenyl-γ-aminopropyl trimethoxy silane, mercapto functional alkoxysilanes such as γ-mercaptopropyl trimethoxy silane , Titanium alkoxides such as titanium tetraisopropoxide and titanium tetra-n-butoxide, titanium chelates such as titanium dioctyloxybis (octylene glycolate) and titanium diisopropoxybis (ethylacetoacetate), zirconium tetra Zirconium chelates such as acetylacetonate and zirconium tributoxymonoacetylacetonate; zirconium acylates such as zirconium tributoxymonostearate; and isocyanate silanes such as methyltriisocyanate silane.

The amount of the silane coupling agent to be used is not particularly limited, but is usually in the range of 0.01 to 20 parts by mass based on 100 parts by mass of the total amount of the solid matter in the curable composition.

The properties of the cured product may be improved by using a thermoplastic organic polymer, if necessary, in the curable composition of the present invention. 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- ) Acrylic acid copolymers, (meth) acrylic acid-methyl methacrylate copolymers, glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymers, polyvinylbutyral, cellulose esters, polyacrylamides, saturated poly Esters and the like.

The curable composition of the present invention is not particularly limited and a solvent capable of dissolving or dispersing the components (A) and (B) commonly used may be used. Examples of the solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone and 2-heptanone; Ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol monomethyl ether and dipropylene glycol dimethyl ether; Esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; Cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol-based solvents such as methanol, ethanol, iso-or n-propanol, iso- or n-butanol, and amyl alcohol; Propylene glycol monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate, etc. Ether-based solvent; BTX type solvents such as benzene, toluene and xylene; Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpene hydrocarbon such as terpine oil, D-limonene, and pinene; Paraffin solvents such as Mineral Spirit, Swazol # 310 (manufactured by Cosmo Matsuyama Oil Co., Ltd.) and Sorbusso # 100 (manufactured by Exxon Chemical); Halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichlorethylene, methylene chloride, and 1,2-dichloroethane; Halogenated aromatic hydrocarbon solvents such as chlorobenzene; Propylene carbonate, carbitol-based solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide , And water. These solvents may be used singly or as a mixed solvent of two or more kinds.

The curable composition of the present invention preferably has a water content of 5 parts by mass or less, more preferably 3 parts by mass or less, since the curable composition of the present invention has improved curability, adhesiveness, and liquid storage stability. If the water content is excessively high, it may be cloudy or the component may precipitate, which is undesirable.

In the curable composition of the present invention, the ultraviolet absorber may be added to the curable composition, or the protective group may be desorbed by heating, light irradiation, acid or the like at a predetermined temperature, A compound expressed can also be used.

As long as it does not impair the effect of the present invention, it is possible to add a coloring agent such as a radical polymerizing monomer, a radical polymerization initiator, a polyol, an inorganic filler, an organic filler, a pigment and a dye, a defoaming agent, Various kinds of resin additives such as a surfactant, a leveling agent, a flame retardant, a thixotropic agent, a diluent, a plasticizer, a stabilizer, a polymerization inhibitor, an ultraviolet absorber, an antioxidant, an antistatic agent, a flow control agent, 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 printing, immersion and the like. Further, the film may be once transferred onto a supporting substrate such as a film and then transferred onto another supporting substrate. There is no limitation on the application method thereof.

The material of the support base is not particularly limited and can be usually used, and examples thereof include inorganic materials such as glass; Cellulose esters such as diacetylcellulose, triacetylcellulose (TAC), propionylcellulose, butyrylcellulose, acetylpropionylcellulose, and nitrocellulose; Polyamide; Polyimide; Polyurethane; Epoxy resin; Polycarbonate; Polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, polybutyl Polyesters such as rheneterephthalate; 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; Polyether ketones; Polyetherimide; There are polymer materials such as polyoxyethylene, norbornene resin and cycloolefin polymer (COP). Then, the supporting substrate may be subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment and the like.

In the method of curing the curable composition of the present invention by irradiation with energy rays, examples of the energy ray include ultraviolet rays, electron rays, X rays, radiation, high frequency waves and the like, and ultraviolet rays are most economically preferable. Examples of ultraviolet light sources include ultraviolet lasers, mercury lamps, xenon lasers, and metal halide lamps.

The conditions for the method of curing the curable composition of the present invention by heating are 1 to 100 minutes at 70 to 250 캜. After pre-applied bake (PAB), it may be pressurized, post-bake (PEB), or baked at several different temperatures. The heating conditions vary depending on the kind of the components and the mixing ratio. For example, the heating conditions are from 70 to 180 DEG C for 5 to 15 minutes in an oven and from 1 to 5 minutes on a hot plate. Thereafter, a cured film can be obtained by heating at 180 to 250 캜, preferably 200 to 250 캜, for 30 to 90 minutes in an oven, and for 5 to 30 minutes in a hot plate, for curing a coating film (coating film).

Specific examples of the use of the curable composition or the cured product of the present invention include adhesives, adhesives for polarizing plates, optical materials represented by lenses for spectacles and imaging, paints, coating agents, lining agents, inks, resists, liquid resists, , Display devices such as color TVs, PC monitors, portable information terminals, digital cameras, organic EL, touch panels, insulating varnishes, insulating sheets, laminated plates, printed boards, semiconductor devices, LED packages, liquid crystal injection holes, · Passivation for optical devices, electrical insulation, electronic components, separators, sealants, molding materials, putty, glass fiber impregnants, sealers, semiconductors and solar cells. A prism lens sheet used for a backlight of a liquid crystal display device, a Fresnel lens sheet used for a screen of a projection TV or the like, a lens portion of a lens sheet such as a lenticular lens sheet, Or an optical lens such as a microlens such as a backlight using such a sheet, an optical element, an optical connector, an optical waveguide, and an optical molding mold.

As the display device of the present invention, it is preferable that each layer such as a lower 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 film made of the cured product of the present invention can be used for each layer.

[Example]

Hereinafter, the present invention will be described in more detail by way of examples and the like, but the present invention is not limited to these examples.

[Examples 1 to 16, Comparative Examples 1 to 7]

The components shown in Tables 1 to 3 were thoroughly mixed to obtain curable compositions of Examples 1 to 16 and Comparative Examples 1 to 7, respectively. The units of Examples and Comparative Examples are parts by mass.

As the cationic polymerizable component (A), the following compounds A1-1 to A1-5, A2-1 to A2-2, A3-1, A4-1 and A5-1 were used.

Compound A1-1: Bisphenol-type diglycidyl ether

Compound A1-2: adekaglycidol ED-509S (monofunctional aromatic epoxy compound manufactured by ADEKA Corporation)

Compound A1-3: Adekaglycylol ED-501 (monofunctional aromatic epoxy compound manufactured by ADEKA Corporation)

Compound A1-4: Orthoallylphenylglycidyl ether

Compound A1-5: Orthophenylphenol glycidyl ether

Compound A2-1: neopentyl glycol diglycidyl ether

Compound A2-2: 1,4-butanediol diglycidyl ether

Compound A3-1: Aronoxetane OXT-221 (manufactured by Toa Gosei Co., Ltd.)

Compound A4-1: 75 parts by mass of methyl methacrylate and 25 parts by mass of glycidyl methacrylate (weight average molecular weight: 7,000)

Compound A5-1: Celloxide 2021P (alicyclic epoxy compound manufactured by Daicel Co., Ltd.)

Compound A5-2: Limonene dioxide

As the cationic polymerization initiator (B), the following compound (B-1) was used.

Compound B-1: A 50% solution of propylene carbonate in a mixture of the compound represented by the following formula (9) and the compound represented by the following formula (10)

(Adhesion)

The curable compositions of Examples 1 to 16 and Comparative Examples 1 to 7 obtained above were each coated on one PMMA film (Sumitomo Chemical Co., Ltd.: Technoloy 125S001), and then subjected to another corona discharge treatment to obtain a COP (Manufactured by Nippon Zeon Co., Ltd., serial no. Zeonoafilm 14-060) film and a laminator, and light of 1000 mJ / cm ² was irradiated onto the COP film Followed by bonding to obtain a test piece. The resulting test piece was subjected to a 90-degree peel test. The curable composition having an adhesion of 1.0 N / cm or more can be used as an adhesive for a polarizing plate. Preferably, the adhesion is 2.0 N / cm or more, and more preferably 3.0 N / cm or more. The obtained results are shown in Tables 1 to 3.

(Hardenability)

The curability of the test pieces was checked together. ++ immediately after the irradiation, tack free of the applied surface was evaluated as ++, tack free after 5 minutes, and tack remaining after 15 minutes. The curable composition having a curability of ++ or + can be used as an adhesive for a polarizing plate, and the curable composition having a curability of ++ is particularly preferably used as an adhesive for a polarizing plate, and the curable composition having a curability is an adhesive for a polarizing plate Can not be used. The obtained results are shown in Tables 1 to 3.

(Coating property)

Each of the curable compositions of Examples 1 to 16 and Comparative Examples 1 to 7 was applied to one PMMA film (Sumitomo Chemical Co., Ltd.: Technoloy 125S001), and then COP treated with another corona discharge treatment Polymer, manufactured by Nippon Zeon Co., Ltd., serial number: Zeonoafilm 14-060) Using a film and a laminator, light of 1000 mJ / cm ² was irradiated over a COP film using an electrodeless ultraviolet lamp, To obtain a test piece. Observation of the appearance of the obtained sample revealed that there were no ruggedness or bubbles, and those with ruggedness or bubbles were rated as x. The curable composition having the coating property? Can be used as an adhesive for a polarizing plate, and the curable composition having an applicability of x can not be used as an adhesive for a polarizing plate.

[Table 1]

[Table 2]

[Table 3]

From Table 1 to Table 3, it was found that the curable composition of the present invention is excellent in adhesion of a cured product.

Claims (7)

A curable composition comprising 100 parts by mass of the cationic polymerizable component (A) and 1 to 10 parts by mass of the cationic polymerization initiator (B)
Wherein the cationic polymerizable component (A) is a polymer (A4) having a weight average molecular weight of 1,000 to 30,000 and having an aromatic epoxy compound (A1), an aliphatic glycidyl compound (A2), an oxetane compound (A3) Wherein the aromatic epoxy compound (A1) is a main component of the cationic polymerizable component (A) and contains a polyfunctional aromatic epoxy compound and a monofunctional aromatic epoxy compound. The method according to claim 1,
Further comprising an alicyclic epoxy compound (A5) as the cationic polymerizable component (A). The method according to claim 1,
Wherein the oxetane compound (A3) is a polyfunctional oxetane compound. 3. The method of claim 2,
Wherein the oxetane compound (A3) is a polyfunctional oxetane compound. A method of curing a curable composition, wherein the curable composition according to any one of claims 1 to 4 is irradiated with an active energy ray. A method of curing a curable composition, wherein the curable composition according to any one of claims 1 to 4 is heated. A cured product of the curable composition according to any one of claims 1 to 4.