KR101768246B1 - Curable composition, hardened material, and method for using curable composition - Google Patents

Abstract

The present invention relates to (A) a silane compound copolymer having a specific repeating unit, (B) an epoxy compound having an isocyanurate skeleton, (C) a curing agent containing an alicyclic acid anhydride having a carboxyl group, and (D) A curing composition containing a silane coupling agent having an anhydride structure, a cured product obtained by curing the composition, and a method of using the composition as an adhesive for optical device fixing material and a sealing material for optical device fixing material. According to the curable composition of the present invention, even when a high-energy light is irradiated or in a high-temperature state, there is no case where the transparency is lowered due to coloring, and it has excellent transparency for a long period of time, Cargo can be obtained. The curable composition of the present invention can be used for forming an optical element fixing material, and can be preferably used as an optical element fixing agent and an optical element fixing agent.

Description

TECHNICAL FIELD [0001] The present invention relates to a curable composition, a cured product, and a curable composition,

The present invention relates to a curable composition which is excellent in transparency and heat resistance and which can obtain a cured product having a high adhesive strength, a cured product obtained by curing the composition, and an adhesive for an optical element fixing agent or an optical element fixing agent And a method of using the same.

BACKGROUND ART [0002] Conventionally, curable compositions have been variously improved depending on their applications and have been widely used as raw materials for optical parts and molded articles, adhesives, coating agents, and the like. For example, a curable composition for forming a cured product having excellent transparency is preferably used as a raw material for an optical component, a curable composition for forming the cured product having a high adhesive force as a coating material thereof, many.

In recent years, the curable composition has also been used as a composition for an optical element fixing agent such as an adhesive for an optical element fixing agent or a sealing agent for an optical element fixing agent when manufacturing an optical element sealing member.

Optical devices include various lasers such as semiconductor lasers (LD), light emitting devices such as light emitting diodes (LED), light receiving devices, composite optical devices, and optical integrated circuits. In recent years, an optical element of blue light or white light having a shorter peak wavelength of light emission has been developed and widely used. Such a light emitting device having a short peak wavelength of light emission has been remarkably advanced in brightness, and the amount of heat generated by the optical device tends to become larger.

However, in recent years, with the increase in brightness of optical devices, a cured product of the optical element fixing composition is exposed to heat of a higher temperature generated from light of higher energy or optical element for a long time and is deteriorated, Or the like.

In order to solve this problem, in Patent Documents 1 to 3, a composition for an optical element fixing material comprising a polysilsesquioxane compound as a main component has been proposed.

However, even in the case of a cured product of a composition for optical element fixing using a polysilsesquioxane compound as a main component described in Patent Documents 1 to 3, it has been difficult to obtain heat resistance and transparency while maintaining a sufficient adhesive strength.

Patent Document 4 discloses an epoxy resin composition using an alicyclic epoxy resin, and Patent Document 5 proposes an epoxy resin composition containing a polythiol compound as a composition used for optical device sealing.

However, even in the case of using these compositions, sufficient light fastness deterioration accompanying temporal change can not be satisfied, or the adhesive strength is lowered in some cases.

Japanese Laid-Open Patent Publication No. 2004-359933 Japanese Patent Application Laid-Open No. 2005-263869 Japanese Laid-Open Patent Publication No. 2006-328231 Japanese Patent Application Laid-Open No. 7-309927 Japanese Laid-Open Patent Publication No. 2009-001752

SUMMARY OF THE INVENTION The present invention has been made in view of the conventional state of the art, and an object of the present invention is to provide a curable composition which is excellent in heat resistance and transparency and which can obtain a cured product having a high adhesive force, a cured product obtained by curing the composition, And a method of using the same as a sealant for a fixing agent or an optical element fixing agent.

As a result of intensive studies to solve the above problems, the present inventors have found that (A) a specific silane compound copolymer, (B) an epoxy compound having an isocyanurate skeleton, (C) an alicyclic acid anhydride having a carboxyl group , And a silane coupling agent (D) having an acid anhydride structure, is a cured product having a high adhesive force even at a high temperature while maintaining excellent transparency and heat resistance over a long period of time The present invention has been accomplished on the basis of these findings.

Thus, according to the first aspect of the present invention, there is provided a curable composition as described in the following [1] to [9].

(I), (ii) and (iii) in the molecule,

[Chemical Formula 1]

: Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) Represents a single bond or a linking group. R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent.]

(Ii), (i) and (iii), (ii) and (iii) or the repeating units (i), (ii) and (iii) A silane compound copolymer having a molecular weight of 1,000 to 30,000,

(B) an epoxy compound having an isocyanurate skeleton,

(C) a curing agent containing an alicyclic acid anhydride having a carboxyl group, and

(D) Silane coupling agent having an acid anhydride structure

≪ / RTI >

[2] The silane compound, a copolymer of the (A), formula: R ¹ -CH (X ^O) existing amount ^{([R 1 -CH (X O} ) -D]) of the group represented by R ² and -D- Is a silane compound copolymer of [R ¹ -CH (X ^O ) -D]: [R ² ] = 60:40 to 5:95 at a molar ratio of the amount [R ² ] .

 [3] The positive electrode active material as described in any of [1] to [4], wherein the content ratio of the components (A), (B), (C) The curable composition according to (1) or (2), wherein [(B) + (C) + (D)] is 90:10 to 50:50.

(1): R ¹ -CH (X ^O ) -D-Si (OR ³ ) _p (X ¹ ) _3-p

: Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) Represents a single bond or a linking group. R ³ represents an alkyl group having 1 to 6 carbon atoms, X ¹ represents a halogen atom, and p represents an integer of 0 to 3.

At least one silane compound (1) represented by the formula

???????? R ² Si (OR ⁴ ) _q (X ² ) _3-q ?????

(Wherein R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent, R ⁴ represents an alkyl group having 1 to 6 carbon atoms, X ² represents a halogen atom, and q represents an integer of 0 to 3 Lt; / RTI &

A silane compound copolymer having a weight average molecular weight of 1,000 to 30,000, obtained by condensing a mixture of silane compounds containing at least one kind of silane compound (2)

(B) an epoxy compound having an isocyanurate skeleton,

(C) a curing agent containing an alicyclic acid anhydride having a carboxyl group, and

(D) Silane coupling agent having an acid anhydride structure

≪ / RTI >

[5] A process for producing a silane coupling agent according to any one of [1] to [4], wherein the silane compound (A ') comprises a silane compound (1) and a silane compound (2) To 5:95. The curable composition according to < 4 >

[6] A method of producing a cement admixture, comprising the steps of: (A) mixing the components (A '), (B), (C) (B) + (C) + (D)] is 90:10 to 50:50. The curable composition according to [4] or [5]

(B) + (C)] :( D (B) + (C)) and (D) by the mass ratio of [ ) = 90:10 to 10:90. [3] The curable composition according to [1] or [4]

[8] The curing agent as described in the above (C), wherein the curing agent (C) is composed of one or more kinds selected from alicyclic acid anhydrides having a carboxyl group and other alicyclic acid anhydrides and whose mass ratio is (alicyclic acid anhydride having a carboxyl group) : (Other alicyclic acid anhydride) = 100: 0 to 10: 90.

[9] The curable composition according to [1] or [4], which is a composition for an optical element fixing material.

According to a second aspect of the present invention, there is provided a cured product of the following [10] and [11].

[10] A cured product obtained by curing the curable composition according to [1] or [4].

[11] A cured product according to [10], which is an optical element fixing material.

According to a third aspect of the present invention, there is provided a method of using the curable composition of the present invention of the following [12] or [13].

[12] A method of using the curable composition according to [1] or [4] as an adhesive for an optical element fixing material.

[13] A method of using the curable composition according to [1] or [4] as a sealing agent for an optical element fixing material.

According to the curable composition of the present invention, even when a high-energy light is irradiated or in a high-temperature state, there is no case where the transparency is lowered due to coloring, and it has excellent transparency for a long period of time, Cargo can be obtained.

The curable composition of the present invention can be used for forming an optical element fixing material, and can be preferably used as an optical element fixing agent and an optical element fixing agent.

Hereinafter, the present invention will be described in detail in terms of 1) curing composition, 2) cured product, and 3) method of using the curing composition.

1) Curable composition

The curable composition of the present invention comprises

(I), (ii) and (iii) in the molecule (A)

(2)

: Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) Represents a single bond or a linking group. R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent.]

(I) and (ii), (i) and (iii), (ii) and (iii) or repeating units (i), (ii) and (iii) A silane compound copolymer having a molecular weight of 1,000 to 30,000, (B) an epoxy compound having an isocyanurate skeleton, (C) a curing agent containing an alicyclic acid anhydride having a carboxyl group, and (D) a silane compound having an acid anhydride structure And a coupling agent.

(A) a silane compound copolymer

(I) and (ii), (i) and (iii) and (ii) of the repeating units represented by the above formulas (i), (ii) and (iii) And a silane compound copolymer having repeating units (i), (ii) and (iii) and having a weight average molecular weight of 1,000 to 30,000 (hereinafter referred to as "silane compound copolymer In some cases).

The silane compound copolymer (A) may have one kind of each of the repeating units (i), (ii) and (iii), or two or more kinds thereof.

In the formulas (i) to (iii), R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹ include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, N-hexyl group, and the like.

X ⁰ is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; Cyano; Or a group represented by formula: OG; .

G represents a protecting group of a hydroxyl group. The protecting group for the hydroxyl group is not particularly limited and includes known protecting groups known as protecting groups for hydroxyl groups. For example, an acyl protecting group; Silyl protecting groups such as a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, and a t-butyldiphenylsilyl group; Acetal-based protecting groups such as a methoxymethyl group, a methoxyethoxymethyl group, a 1-ethoxyethyl group, a tetrahydropyran-2-yl group, and a tetrahydrofuran-2-yl group; an alkoxycarbonyl group protecting group such as a t-butoxycarbonyl group; Ether-based protecting groups such as methyl, ethyl, t-butyl, octyl, allyl, triphenylmethyl, benzyl, p-methoxybenzyl, fluorenyl, trityl and benzhydryl groups; And the like. Of those, G is preferably an acyl group-protecting group.

The acyl group-protecting group is specifically a group represented by the formula -C (= O) R ⁵ . In the formula, R ⁵ represents an alkyl group having 1 to 6 carbon atoms such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i- An alkyl group; Or a phenyl group which may have a substituent.

Examples of the substituent of the phenyl group which may have a substituent represented by R ⁵ include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s- An alkyl group such as a pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group or an i-octyl group; Halogen atoms such as a fluorine atom, a chlorine atom and a bromine atom; An alkoxy group such as a methoxy group or an ethoxy group; .

Among them, X ⁰ is preferably a chlorine atom, a group represented by the formula: OG '(wherein G' represents an acyl group protecting group), and a group represented by the formula: OG ', from the viewpoint of obtaining a cured product having high availability and high adhesion. A group selected from nitrogen, nitrogen and the like is preferable, a group selected from a chlorine atom, an acetoxy group and a cyano group is more preferable, and an acetoxy group is particularly preferable.

D represents a single bond or a linking group.

The linking group includes a divalent organic group which may have a substituent. The number of carbon atoms of the organic group is preferably 1 to 20, more preferably 1 to 10.

Examples of the divalent organic group which may have a substituent include an alkylene group which may have a substituent, an alkenylene group which may have a substituent, an alkynylene group which may have a substituent, an arylene group which may have a substituent, (Alkylene group, alkenylene group, or alkynylene group) which may have a substituent and an arylene group which may have a substituent, and the like.

Examples of the alkylene group of the alkylene group which may have a substituent include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group and the like having 1 to 20 carbon atoms, Alkylene group having 1 to 10 carbon atoms.

Examples of the alkenylene group of the alkenylene group which may have a substituent include an alkenylene group having 2 to 20 carbon atoms such as a vinylene group, a propenylene group, a butenylene group and a pentenylene group, preferably an alkenylene group having 2 to 10 carbon atoms .

The alkynylene group of the alkynylene group which may have a substituent includes an alkynylene group having 2 to 20 carbon atoms such as an ethynylene group and a propynylene group, preferably an alkynylene group having 2 to 10 carbon atoms.

The arylene group of the arylene group which may have a substituent includes an arylene group having 6 to 20 carbon atoms such as an o-phenylene group, a m-phenylene group, a p-phenylene group and a 2,6-naphthylene group, And an arylene group having 1 to 10 carbon atoms.

Examples of the substituent of the alkylene group, alkenylene group, and alkynylene group include a halogen atom such as a fluorine atom and a chlorine atom; An alkoxy group such as a methoxy group or an ethoxy group; Alkylthio groups such as methylthio group and ethylthio group; An alkoxycarbonyl group such as a methoxycarbonyl group or an ethoxycarbonyl group; And the like.

Examples of the substituent of the arylene group include a cyano group; A nitro group; Halogen atoms such as a fluorine atom, a chlorine atom and a bromine atom; Alkyl groups such as methyl group and ethyl group; An alkoxy group such as a methoxy group or an ethoxy group; Alkylthio groups such as methylthio group and ethylthio group; And the like.

These substituents may be bonded at arbitrary positions in groups such as an alkylene group, an alkenylene group, an alkynylene group, and an arylene group, or they may be bonded to one another in the same or different manner.

The divalent group consisting of a combination of an alkylene group, an alkenylene group, or an alkynylene group which may have a substituent and an arylene group which may have a substituent includes an alkylene group, an alkenylene group, An alkynylene group), and a group in which at least one kind of an arylene group which may have the above-mentioned substituent is bonded in series. Specifically, a group represented by the following formula can be mentioned.

(3)

Of these, D is preferably an alkylene group of 1 to 10 carbon atoms, more preferably an alkylene group of 1 to 6 carbon atoms, particularly preferably a methylene group or an ethylene group because a cured product having a high adhesive strength can be obtained.

In the formulas (i) to (iii), R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent.

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ² include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s- N-hexyl group, n-octyl group, i-octyl group, n-nonyl group, n-decyl group and n-dodecyl group.

Examples of the substituent of the phenyl group which may have a substituent represented by R ² include methyl, ethyl, n-propyl, i-propyl, n-butyl, An alkyl group such as a pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group or an i-octyl group; An alkoxy group such as a methoxy group or an ethoxy group; Halogen atoms such as a fluorine atom and a chlorine atom, and the like.

Specific examples of the phenyl group which may have a substituent represented by R ² include a phenyl group, 2-chlorophenyl group, 4-methylphenyl group, 3-ethylphenyl group, 2,4-dimethylphenyl group and 2-methoxyphenyl group .

In the silane compound copolymer (A), the formula: R ¹ -CH (X ^O) of the group represented by the amount present ^{-D- ([R 1 -CH (X} O) -D]) and the amount present in the R ² ( the molar ratio of ^{[R 2]), [R} 1 -CH (X O) -D]: [R 2] = 60:40 ~ 5:95 is preferred, and 50: 50 ~ 5: 95 is more preferred, and Particularly preferred is 50:50 to 10:90. Within this range, a cured product excellent in transparency and adhesiveness and excellent in heat resistance can be obtained.

The amount of the group represented by the formula: R ¹ -CH (X ^O ) -D- and the amount of R ² present can be quantified, for example, by measuring the NMR spectrum of the silane compound copolymer (A).

The silane compound copolymer (A) may be any copolymer such as a random copolymer, a block copolymer, a graft copolymer, and an alternating copolymer, and a random copolymer is particularly preferable.

The weight average molecular weight (Mw) of the silane compound copolymer (A) is in the range of 1,000 to 30,000, preferably 1,500 to 6,000. Within this range, a cured product excellent in handleability of the composition and excellent in adhesiveness and heat resistance can be obtained. The weight average molecular weight (Mw) can be determined, for example, as a standard polystyrene conversion value by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

The molecular weight distribution (Mw / Mn) of the silane compound copolymer (A) is not particularly limited, but is usually in the range of 1.0 to 3.0, preferably 1.1 to 2.0. Within the range, a cured product having excellent adhesion and heat resistance can be obtained.

The silane compound copolymer (A) may be used singly or in combination of two or more.

The silane compound copolymer (A) is a polysilsesquioxane compound having a ladder structure.

The fact that the silane compound copolymer has a ladder-like structure can be confirmed, for example, by measuring the infrared absorption spectrum of the reaction product, X-ray diffraction measurement, and NMR measurement.

In the curable composition of the present invention, the component (A)

(A ') ???????? R ¹ -CH (X ^O ) -D-Si (OR ³ ) _p (X ¹ ) _3-p ?????

: Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group for a hydroxyl group) Represents a single bond or a linking group. R ³ represents an alkyl group having 1 to 6 carbon atoms, X ¹ represents a halogen atom, and p represents an integer of 0 to 3.

At least one silane compound (1) represented by the formula

???????? R ² Si (OR ⁴ ) _q (X ² ) _3-q ?????

(Wherein R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent, R ⁴ represents an alkyl group having 1 to 6 carbon atoms, X ² represents a halogen atom, and q represents an integer of 0 to 3 Lt; / RTI >

Silane compound copolymer (A ') having a weight average molecular weight of 1,000 to 30,000, obtained by condensing a mixture of a silane compound containing at least one silane compound (2) represented by the following formula , And the silane compound copolymer (A) is preferably the silane compound copolymer (A ').

[Silane compound (1)]

The silane compound (1) is a compound represented by the formula (1): R ¹ -CH (X ^O ) -D-Si (OR ³ ) _p (X ¹ ) _{3- p} . By using the silane compound (1), it is possible to obtain a silane compound copolymer having good transparency and adhesion even after curing.

In the formula (1), R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom. Specific examples include those exemplified as R ¹ in the silane compound copolymer (A).

In the formula (1), X ⁰ represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a cyano group or a group represented by the formula OG (wherein G represents a protecting group of a hydroxyl group) Represents a single bond or a linking group. Specific examples of what represented by X ⁰ and D are, respectively, those exemplified as X ⁰ and D of the silane compound copolymer (A).

R ³ represents an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, Lt; 6 >

X ¹ represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

p represents an integer of 0 to 3;

When p is 2 or more, the OR ^{3 s may be the} same or different. When (3-p) is 2 or more, X ^{1s may be the} same or different.

Specific examples of the silane compound (1) include chloromethyltrimethoxysilane, bromomethyltriethoxysilane, 2-chloroethyltripropoxysilane, 2-bromoethyltributoxysilane, 3-chloropropyltri 3-chloropropyltriethoxysilane, 3-chloropropyltriethoxysilane, 3-chloropropyltriethoxysilane, 3-bromopropyltrimethoxysilane, 3-chloropropyltriethoxysilane, , 3-bromopropyltripropoxysilane, 3-bromopropyltributoxysilane, 3-fluoropropyltrimethoxysilane, 3-fluoropropyltriethoxysilane, 3-fluoropropyltripropoxysilane Chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 4-chlorobutyltripropoxysilane, 5-chlorobutyltrimethoxysilane, 3-chloropropyltrimethoxysilane, Pentyltrifluoroxysilane, 2-chloropropyltrimethoxysilane, 3- (3-chloro-3-methoxycarbonylpropyltrimethoxysilane, o- (2-chloroethyl) phenyltripropoxysilane, m- (2-chloroethyl) phenyl Trialkoxysilane compounds wherein X ⁰ is a halogen atom, such as trimethoxysilane, p- (2-chloroethyl) phenyltriethoxysilane and p- (2-fluoroethyl) phenyltrimethoxysilane;

Chloromethyltrichlorosilane, 3-chloropropyltrichlorosilane, 3-chloropropyltrichlorosilane, 3-chloropropyltrichlorosilane, 3-chloropropyltrichlorosilane, 3-chloropropyltrichlorosilane, 3-chloropropyldichloroethoxysilane, 3-chloropropyldichloroethoxysilane, 3-chloropropyldichloroethoxysilane, 3-chloropropyldichloroethoxysilane, 3-chloropropyldichloroethoxysilane, 3- Propyl trichlorosilane, 3-fluoropropyl trichlorosilane, 3-fluoropropyl trichlorosilane, 3-fluoropropyl trichlorosilane, 3-fluoropropyl trichlorosilane, 3-chloropropyl dimethoxysilane, Chloro-n-butyl chlorodiethoxysilane, 3-chloro-3-acetic acid, 3-chlorobutylchlorodiethoxysilane, 3-chloropropyltriethoxysilane, 3- Halogeno silane compounds in which X ⁰ is a halogen atom, such as t-butyldichloroethoxy silane and 3-chloro-3-methoxycarbonylpropyltribromosilane;

Cyanomethyltrimethoxysilane, cyanomethyltriethoxysilane, 1-cyanoethyltrimethoxysilane, 2-cyanoethyltrimethoxysilane, 2-cyanoethyltriethoxysilane, 2-cyano Cyanopropyltriethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3- 2-cyanopentyltrimethoxysilane, 2-cyanopropyltrimethoxysilane, 2- (cyanomethoxy) ethyltrimethoxysilane, 2- (2-cyanoethoxy) ethyl tri (Cyanomethyl) phenyltriethoxysilane, p- (2-cyano) phenyltriethoxysilane, m- (cyanomethyl) phenyltrimethoxysilane, p- Ethyl) phenyltrimethoxysilane; trialkoxysilane compounds wherein X ⁰ is a cyano group;

Cyanomethyl trichlorosilane, cyanomethyl bromodimethoxysilane, 2-cyanoethyl dichloromethoxysilane, 2-cyanoethyl dichloroethoxysilane, 3-cyanopropyl trichlorosilane, 3-cyanopropyl 3-cyanopropyldichloroethoxysilane, 3-cyanopropylpropylchlorodimethoxysilane, 3-cyanopropylchlorodiethoxysilane, 4-cyanobutylchloro 2- (2-cyanoethoxy) ethyl bromodiethoxy silane, 2 (2-cyanoethoxy) ethyl trichlorosilane, 2-cyanoethoxy silane, - (2-cyanoethoxy) ethyldichloropropoxy silane, o- (2-cyanoethyl) phenyl trichlorosilane, m- (2- cyanoethyl) phenylmethoxy dibromosilane, p- Halogeno silane compounds in which X ⁰ is a cyano group, such as p- (2-cyanoethyl) phenyldimethoxychlorosilane and p- (2-cyanoethyl) ;

3-acetoxypropyltrimethoxysilane, 3-acetoxypropyltriethoxysilane, 3-acetoxypropyltriethoxysilane, 3-acetoxypropyltriethoxysilane, 3-acetoxypropyltriethoxysilane, 3- , 3-propionyloxypropyltriethoxysilane, 3-benzoyloxypropyltrimethoxysilane, 3-benzoyloxypropyltriethoxysilane, 3-benzoyloxypropyltripropoxysilane, 3-benzoyloxypropyltributoxy (2-tetrahydropyranyloxy) propyltripropoxysilane, 3- (2-tetrahydropyranyloxy) silane, 2-trimethylsilyloxyethyltrimethoxysilane, 3-triethylsilyloxypropyltriethoxysilane, 3- 3-methoxymethyloxypropyltrimethoxysilane, 3-methoxyethoxymethyloxypropyltriethoxysilane, 3- (1-ethoxyethyloxy) propyltripropoxysilane , 3- (t-butoxycarbonyloxy) propyltrimethoxy Is, 3-t- butoxy-trimethoxysilane, 3-benzyloxy, such as the profile triethoxysilane, 3-triphenyl methoxy-ethoxy propyl triethoxysilane, X ⁰ is the formula: trialkoxy group represented by OG Silane compounds;

Acetoxypropyltrichlorosilane, 3-acetoxypropyltrichlorosilane, 3-acetoxypropyltrichlorosilane, 3-acetoxypropyltrichlorosilane, 3-acetoxypropyltrichlorosilane, 3-acetoxypropyltrichlorosilane, 3- 3-trimethylsilyloxypropylchlorodimethoxysilane, 3-triethylsilyloxypropyldichloromethoxysilane, 3- (2-tetrahydropyranyloxy) -2-methylpropyltrimethoxysilane, 3- ) Propyl chlorodiethoxysilane, 3- (2-tetrahydrofuranyloxy) propyldichloroethoxysilane, 3-methoxymethyloxypropyltribromosilane, 3-methoxyethoxymethyloxypropyltrichlorosilane, 3- Butoxycarbonyloxypropyldichlorosilane, 3-t-butoxypropylchlorodiethoxysilane, 3-tributylmethoxypropyldichloroethane, 3-t-butoxycarbonyloxypropyldichloromethoxysilane, 3- Gt; , 3-benzyloxypropyltribromosilane, halogeno silane compounds wherein X ⁰ is a group represented by the formula: OG; And the like.

These silane compounds (1) may be used singly or in combination of two or more.

Among them, as the silane compound (1), trialkoxysilane compounds wherein X ⁰ is a halogen atom, trialkoxysilane compounds wherein X ⁰ is a cyano group, or compounds represented by X ⁰ Is preferably a trialkoxysilane compound having a 3-chloropropyl group, a trialkoxysilane compound having a 3-acetoxypropyl group, a trialkoxysilane compound having a 2-cyanoethyl group Alkoxysilane compounds, or trialkoxysilane compounds having a 3-cyanopropyl group are more preferable.

[Silane compound (2)]

The silane compound (2) is a compound represented by the formula (2): R ² Si (OR ⁴ ) _q (X ² ) _{3- q} .

In the formula (2), R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent. Specific examples include those exemplified as R ² in the silane compound copolymer (A).

R ⁴ represents an alkyl group having 1 to 6 carbon atoms which is the same as R ³ above.

X ² represents the same halogen atom as X ¹ .

q represents any integer of 0 to 3;

When q is 2 or more, the OR ^{4 s may be the} same or different. When (3-q) is 2 or more, X ^{2 may be the} same or different.

Specific examples of the silane compound (2) include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-butyltriethoxysilane butyltrimethoxysilane, n-pentyltriethoxysilane, n-hexyltrimethoxysilane, i-octyltriethoxysilane, dodecyltrimethoxysilane, methyldimethoxyethoxysilane, methyldiethoxy Alkyltrialkoxysilane compounds such as methoxysilane;

Alkyl halides such as methyl chlorodymethoxysilane, methyl dichloromethoxysilane, methyl chlorodiethoxysilane, ethyl chlorodymethoxysilane, ethyl dichloromethoxysilane, n-propyl chlorodymethoxysilane, n-propyldichloromethoxysilane, Geno alkoxy silane compounds;

Alkyltrihalogenosilane compounds such as methyltrichlorosilane, methyltribromosilane, ethyltrichlorosilane, ethyltribromosilane and n-propyltrichlorosilane;

Phenyltrimethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, phenyldimethoxyethoxysilane, Phenyltrialkoxysilane compounds which may have a substituent such as methoxymethoxysilane;

Phenylhalogenoalkoxysilane compounds which may have a substituent such as phenylchlorodimethoxysilane, phenyldichloromethoxysilane, phenylchloromethoxyethoxysilane, phenylchlorodiethoxysilane, and phenyldichloroethoxysilane;

A phenyltrihalogenosilane compound which may have a substituent such as phenyltrichlorosilane, phenyltribromosilane, 4-methoxyphenyltrichlorosilane, 2-chlorophenyltrichlorosilane or 2-ethoxyphenyltrichlorosilane; .

These silane compounds (2) may be used singly or in combination of two or more.

[Mixture of silane compounds]

The mixture of the silane compound used in producing the silane compound copolymer (A ') may be a mixture of the silane compound (1) and the silane compound (2), and may be a mixture of the silane compound A mixture containing the silane compound (1) and the silane compound (2) is preferable.

The ratio of [silane compound (1)]: [silane compound (2)] = 60: 40 to 5:95 in terms of the molar ratio of the silane compound (1) to the silane compound (2) : 50 to 5:95, and particularly preferably 50:50 to 10:90.

The method of condensing the silane compound mixture is not particularly limited, but a silane compound (1), a silane compound (2) and other silane compounds as required are dissolved in a solvent, and a predetermined amount of a catalyst is added , And stirring at a predetermined temperature.

The catalyst to be used may be either an acid catalyst or a base catalyst.

Examples of the acid catalyst include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid; Organic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic acid, and trifluoroacetic acid; And the like.

Examples of the base catalyst include trimethylamine, triethylamine, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, pyridine, 1,8-diazabicyclo [5.4.0] -7- undecene, aniline, , 1,4-diazabicyclo [2.2.2] octane, imidazole and the like; Organic salt hydroxides such as tetramethylammonium hydroxide and tetraethylammonium hydroxide; Metal alcoholates such as sodium methoxide, sodium ethoxide, sodium t-butoxide and potassium t-butoxide; Metal hydrides such as sodium hydride and calcium hydride; Metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; Metal carbonates such as sodium carbonate, potassium carbonate, and magnesium carbonate; Metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; And the like.

Among these, as the catalyst to be used, an acid catalyst is preferable, and an inorganic acid is more preferable.

The amount of the catalyst to be used is usually in the range of 0.1 mol% to 10 mol%, preferably 1 mol% to 5 mol%, based on the total molar amount of the silane compound.

The solvent to be used may be appropriately selected depending on the kind of the silane compound and the like. For example, water; Aromatic hydrocarbons such as benzene, toluene and xylene; Esters such as methyl acetate, ethyl acetate, propyl acetate and methyl propionate; Ketones such as acetone, methyl ethyl ketone, methyl i-butyl ketone, and cyclohexanone; Alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, i-butyl alcohol, s-butyl alcohol and t-butyl alcohol; And the like. These solvents may be used alone or in combination of two or more.

Among them, water, aromatic hydrocarbons and mixed solvents thereof are preferable, and mixed solvents of water and toluene are particularly preferable. When water and toluene are used, the ratio of water to toluene (volume ratio) is preferably 1: 9 to 9: 1, more preferably 7: 3 to 3: 7.

The amount of the solvent to be used is such that the total molar amount of the silane compound per liter of the solvent is usually 0.1 to 10 mol, preferably 0.5 to 10 mol.

The temperature at which the silane compound is condensed (reacted) is usually from 0 占 폚 to the boiling point of the solvent used, preferably from 20 占 폚 to 100 占 폚. If the reaction temperature is too low, the progress of the condensation reaction may become insufficient. On the other hand, if the reaction temperature is excessively high, it becomes difficult to suppress gelation. The reaction is usually completed in 30 minutes to 20 hours.

After the completion of the reaction, when an acid catalyst is used, an alkaline aqueous solution such as an aqueous solution of sodium hydrogencarbonate is added to the reaction solution. When a base catalyst is used, neutralization is performed by adding an acid such as hydrochloric acid to the reaction solution, Is removed by filtration or washing with water or the like to obtain a desired silane compound copolymer.

(B) an epoxy compound having an isocyanurate skeleton

The curable composition of the present invention contains an epoxy compound having an isocyanurate skeleton (hereinafter sometimes referred to as "epoxy compound (B)") as the component (B).

Since the curable composition of the present invention contains the epoxy compound (B), a cured product excellent in heat resistance and transparency can be obtained even after the thermal history.

The epoxy compound (B) is not particularly limited as far as it is a compound having an isocyanurate skeleton (the following (c), in the formula, - represents a bonding hand) and an epoxy ring in the molecule. In the isocyanurate skeleton (c), there may be a tautomer as shown below (cyanurate skeleton (c '), in the formula, - indicates a binding partner), but an epoxy compound having this skeleton Is also contained in the epoxy compound (B) used in the present invention.

[Chemical Formula 4]

Among them, the epoxy compound (B) is preferably at least one of hydrogen atoms bonded to nitrogen atoms at positions 1, 3 and 5 of the isocyanurate ring, as shown in the following formulas (c-1) to (E) having an epoxy ring are preferable.

[Chemical Formula 5]

(Wherein E represents a group having an epoxy ring and R represents any group other than a group having an epoxy ring such as a hydrogen atom or an organic group)

As the group (E) having the epoxy ring, for example,

[Chemical Formula 6]

(Wherein a, b, and c each represent an integer of 1 to 20, and the methylene group may be substituted with an alkyl group such as a methyl group or an ethyl group).

As specific examples of the epoxy compound (B), glycidyl isocyanurate, diglycidyl isocyanurate, tris (2,3-epoxypropyl) iso And a mixture containing two or more of these compounds, and the like can be given as examples of the above-mentioned monomers. These monomers may be used alone or in combination of two or more.

Examples of the epoxy compound (B) include commercially available epoxy compounds having an isocyanurate skeleton (for example, TEPIC-S, TEPIC-PAS B22, TEPIC-PAS B26, Ltd.) may be used as it is.

The compounding amount of the epoxy compound (B) is not particularly limited, but is preferably 50 to 300 g / eq, more preferably 100 to 200 g / eq, in view of obtaining a cured product having a higher adhesive strength. The epoxy equivalent is a value measured in accordance with JIS K 7236: 2001.

(C) Curing agent

The curable composition of the present invention contains, as the component (C), a curing agent containing an alicyclic acid anhydride having a carboxyl group (hereinafter sometimes referred to as "curing agent (C)"). Since the curable composition of the present invention contains the curing agent (C), a cured product having excellent heat resistance can be obtained.

The alicyclic acid anhydride having a carboxyl group is an acid anhydride having an alicyclic structure substituted with at least one carboxyl group. Examples of the alicyclic structure include a saturated cyclic hydrocarbon (cycloalkane) structure, an unsaturated cyclic hydrocarbon (cycloalkene, cycloalkane) structure, and the like.

Examples of the alicyclic acid anhydride include 3-methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl-1,2,3,6-tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, Hexahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, methylnadic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, norbornane- Methyl-5-norbornene-2,3-dicarboxylic acid anhydride, methyl-norbornane-2,3-dicarboxylic anhydride, and the like.

The carboxyl group may be substituted at any position of the alicyclic structure of the alicyclic acid anhydride, and the substitution position and the number of the substituted carboxyl groups are not particularly limited.

Of these, cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride in which a carboxyl group is substituted for hexahydrophthalic anhydride, cyclohexane-1,2,3-tricarboxylic acid-1,2-anhydride And cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride are particularly preferable. This compound may have any stereoisomer, but may be any isomer.

The alicyclic acid anhydride having a carboxyl group may be used singly or in combination of two or more kinds.

The curing agent (C) may further contain another curing agent.

Examples of other curing agents include aliphatic acid anhydrides such as alicyclic acid anhydrides having no carboxyl group (hereinafter referred to as "other alicyclic acid anhydrides") and polyazelaic anhydride, aliphatic amine curing agents, alicyclic amine curing agents, Secondary or tertiary amine curing agents, aromatic amine curing agents, dicyandiamide, boron trifluoride amine complexes, imidazole compounds, and the like.

The other curing agents may be used alone or in combination of two or more.

As other curing agents, other alicyclic acid anhydrides are preferable in that a cured product having a high adhesive strength even at a high temperature can be obtained. Examples of other alicyclic acid anhydrides include the same alicyclic acid anhydrides as the alicyclic acid anhydrides having a carboxyl group. Among them, 3-methyl-hexahydrophthalic anhydride and 4-methyl-hexahydrophthalic anhydride are preferable, and 4-methyl-hexahydrophthalic anhydride is particularly preferable.

The curing agent (C) is preferably composed of one or more kinds selected from alicyclic acid anhydrides having a carboxyl group and other alicyclic acid anhydrides, and the mass ratio thereof is (alicyclic acid anhydride having a carboxyl group): Is preferably 100: 0 to 10:90, and more preferably 50:50 to 10:90.

(D) Silane coupling agent

The curable composition of the present invention contains a silane coupling agent having an acid anhydride structure (hereinafter occasionally referred to as "silane coupling agent (D)") as the component (D). Since the curable composition of the present invention contains the silane coupling agent (D), the cured product having excellent transparency and high adhesive strength can be obtained without phase separation (cloudiness).

The silane coupling agent (D) is an organosilicon compound having both a group (Y) having an acid anhydride structure and a hydrolyzable group (OR ^b ) in one molecule. Specifically, it is a compound represented by the following formula (d).

(7)

R ^a represents an alkyl group having 1 to 6 carbon atoms or a phenyl group which may have a substituent, R ^b represents an alkyl group having 1 to 6 carbon atoms, i represents an integer of 1 to 3, and Y represents an acid anhydride structure, , J represents an integer of 0 to 2, k represents an integer of 1 to 3, and i + j + k = 4.

Y is a group represented by the following formula

[Chemical Formula 8]

(Wherein h represents an integer of 0 to 10), and the group represented by (Y1) is particularly preferable.

Formula (d) wherein the alkyl group of 1 to 6 carbon atoms represented by R ^a, R ^b is, there may be mentioned the same groups as alkyl groups having 1 to 6 carbon atoms represented by the R ¹ as a first example, the substituent represented by the above R ^a May be the same groups as those exemplified above as the phenyl group which may have a substituent represented by R ² .

Among them, the compound represented by the formula (d) is preferably a compound represented by the following formula (d-1)

[Chemical Formula 9]

(Wherein R ^b , h, i, j and k have the same meanings as defined above)

Are preferred. In the formula, h is preferably 2 to 8.

Specific examples of the silane coupling agent represented by the formula (d-1) include 2-trimethoxysilylethylsuccinic anhydride, 3-triethoxysilylpropylsuccinic anhydride and the like.

The silane coupling agent (D) may be used singly or in combination of two or more.

The content of the components (A), (B), (C) and (D) in the curable composition of the present invention is preferably in the range of the mass ratio of (A) to (B) + (C) + , And (A): [(B) + (C) + (D)] = 90:10 to 50:50. The content ratio of the components (A '), (B), (C) and (D) is preferably in the range of from (A') to (B ' ): [(B) + (C) + (D)] = 90:10 to 50:50.

The content ratio of the components (B), (C) and (D) is preferably in the range of [(B) + (C)] :( D) = 90:10 to 10:90.

By using each component at such a ratio, it is possible to obtain a curable composition which is excellent in transparency and heat resistance over a long period of time, and can obtain a cured product having a high adhesive force even at a high temperature.

The curable composition of the present invention may further contain other components as long as the object of the present invention is not impaired.

Other components include a curing catalyst, an antioxidant, an ultraviolet absorber, a light stabilizer, and a diluent.

The curing catalyst is added to promote curing. Examples of the curing catalyst include 2-methylimidazole, triphenylphosphine and the like. These curing catalysts may be used alone or in combination of two or more.

The antioxidant is added to prevent oxidation deterioration during heating. Examples of the antioxidant include phosphorus antioxidants, phenol antioxidants, and sulfur-based antioxidants.

Examples of the phosphorus antioxidant include triphenyl phosphite, diphenyl isodecyl phosphite, phenyl diisodecyl phosphite, tris (nonylphenyl) phosphite, diisodecyl pentaerythritol phosphite, tris (2,4- t-butylphenyl) phosphite, cyclic neopentane tetraylbis (octadecyl) phosphite, cyclic neopentane tetraylbis (2,4-di-t-butylphenyl) phosphite, cyclic neopentane tetra Bis (2,4-di-t-butyl-4-methylphenyl) phosphite, bis [2-t-butyl- Phosphites such as phosphite; Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (3,5- Oxa-10-phosphaphenanthrene-10-oxide, 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10- ; .

Examples of the phenol-based antioxidant include 2,6-di-t-butyl-p-cresol, dibutylhydroxytoluene, butylated hydroxyanisole, 2,6- Mono-phenols such as aryl-? - (3,5-di-t-butyl-4-hydroxyphenyl) propionate; (4-methyl-6-t-butylphenol), 2,2'-methylenebis (4-ethyl- Butylphenol), 4,4'-butylidenebis (3-methyl-6-t-butylphenol), 3,9-bis [1,1- 3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] 2,4,8,10-tetraoxaspiro [5,5] undecane; Methyl-4-hydroxy-5-t-butylphenyl) butane, 1,3,5-trimethyl-2,4,6-tris (3,5- (3 ', 5'-di-t-butyl-4'-hydroxyphenyl) propionate] methane, bis [3,3' Tris (3 ', 5'-di-t-butyl-4'-hydroxyphenyl) butyric acid] glycol ester, 1,3,5- Benzyl) -S-triazine-2,4,6- (1H, 3H, 5H) trione, and tocophenol; .

Examples of the sulfur-based antioxidant include dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate .

These antioxidants may be used alone or in combination of two or more. However, since the curable composition of the present invention contains the component (B) and the component (D), the oxidation deterioration during heating hardly occurs even when no antioxidant is specifically present. When an antioxidant is used, the amount thereof is usually 0.01 to 10 parts by mass based on 100 parts by mass of the silane compound copolymer (A) or (A ').

The ultraviolet absorber is added for the purpose of improving the light resistance of the resulting cured product.

Examples of the ultraviolet absorber include salicylic acids such as phenyl salicylate, p-t-butylphenyl salicylate, and p-octylphenyl salicylate; Dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2 Dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and 2-hydroxy-4-methoxy- Phenones; Benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (2'- Butylphenyl) benzotriazole, 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5- chlorobenzotriazole, 2- Dihydroxy-3 ', 5'-di-t-butylphenyl) -5-chlorobenzotriazole, 2- (2'- Benzotriazole such as 2 - {(2'-hydroxy-3 ', 3 ", 4", 5 ", 6" -tetrahydrophthalimidemethyl) -5'-methylphenyl} benzotriazole Solvation; Bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis Hindered amines such as 2,2,6,6-pentamethyl-4-piperidyl) [{3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl} methyl] butyl malonate; And the like.

These ultraviolet absorbers may be used singly or in combination of two or more.

The amount of the ultraviolet absorber to be used is usually 0.01 to 10 parts by mass based on 100 parts by mass of the silane compound copolymer (A) or (A ').

The light stabilizer is added for the purpose of improving the light resistance of the resulting cured product.

Examples of the light stabilizer include poly {[6- (1,1,3,3-tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl} , 6,6-tetramethyl-4-piperidine) imino} hexamethylene {(2,2,6,6-tetramethyl-4-piperidine) imino} .

These light stabilizers may be used alone or in combination of two or more.

The amount of the light stabilizer to be used is usually 0.01 to 10 parts by mass based on 100 parts by mass of the silane compound copolymer (A) or (A ').

A diluent is added to adjust the viscosity of the curable composition.

As the diluting agent, for example, glycerin diglycidyl ether, butanediol diglycidyl ether, diglycidyl aniline, neopentyl glycol glycidyl ether, cyclohexanedimethanol diglycidyl ether, alkylenediglycidyl Polyvinylpyrrolidone, diallyl ether, polyglycol diglycidyl ether, polypropylene glycol diglycidyl ether, trimethylol propane triglycidyl ether, glycerine triglycidyl ether, 4-vinylcyclohexene monoxide, vinylcyclohexene dioxide, Hexene dioxide, and the like.

These diluents may be used singly or in combination of two or more.

The curable composition of the present invention can be obtained by, for example, mixing the above components (A) or (A '), (B), (C) By mixing and de-mixing.

According to the curable composition of the present invention obtained in the above-described manner, transparency does not decrease due to coloration even in the case of irradiation with high energy light or in a high temperature state, and excellent transparency is ensured over a long period of time, Can be obtained.

Therefore, the curable composition of the present invention is preferably used as a raw material for an optical component or a molded article, an adhesive agent, a coating agent, and the like. Particularly, the curable composition of the present invention can be preferably used as a composition for an optical element fixing material because the problem of deterioration of the optical element fixing material accompanying the increase in brightness of an optical element can be solved.

2) Cured goods

A second aspect of the present invention is a cured product obtained by curing the curable composition of the present invention.

As a method of curing the curable composition of the present invention, a heat curing may be mentioned. The heating temperature for curing is usually from 100 to 200 DEG C, and the heating time is usually from 10 minutes to 20 hours, preferably from 30 minutes to 10 hours.

The cured product of the present invention is excellent in transparency over a long period of time and has a high adhesive force since it does not suffer from deterioration of transparency when it is colored or colored even when it is irradiated with high energy light or at high temperature.

Therefore, the cured product of the present invention is preferably used as an optical component, a molded article, an adhesive layer, a coating layer and the like. In particular, the cured product of the present invention can be preferably used as an optical element fixing material because the problem of deterioration of the optical element fixing material accompanying the increase in brightness of the optical element can be solved.

The high hardness of the cured product of the present invention can be confirmed, for example, by measuring the adhesive strength in the following manner. That is, the curable composition is applied to the mirror surface of the silicon chip, the coated surface is put on the adherend, pressed and cured by heat treatment. This was allowed to stand for 30 seconds on a measurement stage of a bond tester heated in advance at a predetermined temperature (for example, 23 占 폚, 100 占 폚) to remove the adhesive agent from the position of 50 占 퐉 height from the adherend in the horizontal direction ) To measure the adhesive force between the test piece and the adherend.

The adhesive strength of the cured product is preferably 110 N / 2 mm □ or more at 23 ° C.

The excellent transparency of the cured product can be confirmed by measuring the light transmittance. The light transmittance of the cured product is preferably 80% or more, more preferably 84% or more, and preferably 87% or more for light having a wavelength of 450 nm, for light having a wavelength of 400 nm.

The excellent heat resistance of the cured product over a long period of time can be confirmed from the fact that the change of the transparency is small even after the cured product is left at a high temperature for a long time. The transparency is preferably at least 70%, more preferably at least 80%, of the initial transmittance at a wavelength of 400 nm after being left at 150 DEG C for 500 hours.

3) Method of using the curable composition

A third aspect of the present invention is a method of using the curable composition of the present invention as an adhesive for an optical element fixing agent or an optical element fixing agent.

Examples of the optical element include light emitting elements such as LEDs and LDs, light receiving elements, composite optical elements, and optical integrated circuits.

<Adhesive for optical element fixing material>

The curable composition of the present invention can be preferably used as an adhesive for an optical element fixing material.

As a method of using the curable composition of the present invention as an adhesive for optical element fixing materials, there is a method in which the composition is applied to one or both of adhesive surfaces of a material (an optical element and its substrate or the like) to be adhered, And a method in which the materials to be bonded are firmly adhered to each other by heating and curing.

As a main substrate material for bonding an optical element, glass such as soda lime glass and heat resistant hard glass; Ceramics; Metals such as iron, copper, aluminum, gold, silver, platinum, chromium, titanium and alloys of these metals, stainless steel (SUS302, SUS304, SUS304L, SUS309 and the like) But are not limited to, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ethylene-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetheretherketone, polyether sulfone, polyphenylene sulfide, , Synthetic resins such as polyimide, polyamide, acrylic resin, norbornene resin, cycloolefin resin and glass epoxy resin; And the like.

The heating temperature at the time of heat curing varies depending on the curable composition to be used and the like, but is usually from 100 to 200 ° C. The heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.

<Sealant for Optical Element Fixture>

The curable composition of the present invention can be preferably used as an encapsulant of an optical device encapsulation material.

As a method of using the curable composition of the present invention as an encapsulant for optical device fixtures, for example, a method of molding the composition into a desired shape, obtaining a molded article containing the optical device, And the like.

The method for molding the curable composition of the present invention into a desired shape is not particularly limited, and a known transfer molding method such as a common transfer molding method or a casting method can be employed.

The heating temperature at the time of heat curing varies depending on the curable composition to be used and the like, but is usually from 100 to 200 ° C. The heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.

Since the obtained optical element encapsulant uses the curable composition of the present invention, even if the optical element has a peak wavelength of 400 to 490 nm in short wavelength, such as a white or blue LED, It is excellent in transparency and heat resistance that is not deteriorated.

Example

Next, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to the following examples.

(Weight average molecular weight measurement)

The weight average molecular weight (Mw) of the silane compound copolymer obtained in Production Example was measured in terms of standard polystyrene and measured under the following conditions and conditions.

Device name: HLC-8220 GPC, manufactured by Tosa Corporation

Columns: TSKgel GMHXL, TSKgel GMHXL, and TSKgel 2000HXL connected in series

Solvent: tetrahydrofuran

Injection amount: 80 μl

Measuring temperature: 40 ° C

Flow rate: 1 ml / min

Detector: differential refractometer

(Measurement of IR spectrum)

The IR spectrum of the silane compound copolymer obtained in Production Example was measured using the following apparatus.

Fourier transform infrared spectrophotometer (Spectrum 100, manufactured by Perkin Elmer)

(Production Example 1)

16.7 g (84 mmol) of phenyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) as the silane compound (2) and 3-acetoxypropyltrimethoxysilane as the silane compound (1) were added to a 300 ml egg- 8.0 g (36 mmol) of toluene as a solvent, 60 ml of toluene and 30 ml of distilled water were charged and 0.15 g (1.5 mmol) of phosphoric acid (manufactured by Kanto Chemical Co., Ltd.) Stirring was continued at room temperature for a further 16 hours.

After completion of the reaction, 100 ml of ethyl acetate was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. After a short pause, the organic layer was separated. Subsequently, the organic layer was washed twice with distilled water and then dried over anhydrous magnesium sulfate. The magnesium sulfate was separated by filtration, and the filtrate was concentrated to 50 ml with a separator. The filtrate was dripped into a large amount of n-hexane and precipitated, and the precipitate was separated by decantation. The resulting precipitate was dissolved in methyl ethyl ketone and recovered. The solvent was distilled off under reduced pressure using this distributor, followed by vacuum drying to obtain 14.7 g of the silane compound copolymer (A1).

The silane compound copolymer (A1) had a weight average molecular weight (Mw) of 2,700 and a molecular weight distribution (Mw / Mn) of 1.53.

The IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A1) is shown below.

Si-Ph: 699 cm ^-1 , 741 cm ^-1 , Si-O: 1132 cm ^-1 , -CO: 1738 cm ^-1

(Production Example 2)

The procedure of Preparation Example 1 was repeated except that the amount of phenyltrimethoxysilane used was changed to 14.3 g (72 mmol) and the amount of 3-acetoxypropyltrimethoxysilane was changed to 10.7 g (48 mmol) , 15.9 g of the silane compound copolymer (A2) was obtained.

The silane compound copolymer (A2) had a weight average molecular weight (Mw) of 2,600 and a molecular weight distribution (Mw / Mn) of 1.50.

The IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A2) is shown below.

Si-Ph: 699 cm ^-1 , 741 cm ^-1 , Si-O: 1132 cm ^-1 , -CO: 1738 cm ^-1

(Production Example 3)

The procedure of Preparation Example 1 was repeated except that the amount of phenyltrimethoxysilane used was changed to 19.0 g (96 mmol) and the amount of 3-acetoxypropyltrimethoxysilane to be used was changed to 5.3 g (24 mmol) , 14.9 g of the silane compound copolymer (A3) was obtained.

The silane compound copolymer (A3) had a weight average molecular weight (Mw) of 2,500 and a molecular weight distribution (Mw / Mn) of 1.59.

The IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A3) is shown below.

Si-Ph: 700 cm ^-1 , 742 cm ^-1 , Si-O: 1132 cm ^-1 , -CO: 1738 cm ^-1

(Production Example 4)

In the same manner as in Production Example 1, instead of using 16.7 g (84 mmol) of phenyltrimethoxysilane and 8.0 g (36 mmol) of 3-acetoxypropyltrimethoxysilane, phenyltrimethoxysilane 14.2 g (60 mmol) of 11.9 g (60 mmol) of 3-glycidoxypropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter referred to as "GlyTMS" ), 16.3 g of the silane compound copolymer (A4) was obtained in the same manner as in Production Example 1.

 The silane compound copolymer (A4) had a weight average molecular weight (Mw) of 2,800 and a molecular weight distribution (Mw / Mn) of 1.56.

 The IR spectrum (Fourier transform infrared spectrophotometer (FT-IR)) data of the silane compound copolymer (A4) is shown below.

Si-Ph: 700 cm ^-1 , 742 cm ^-1 , Si-O: 1132 cm ^-1 , epoxy group: 1254 cm ^-1

(Production Example 5)

19.0 g (96 mmol) of phenyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) as a silane compound (2) and 3-chloropropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) (Manufactured by Kanto Chemical Co., Ltd.) (4.77 g, 24 mmol), 60 ml of toluene as a solvent and 30 ml of distilled water were charged, and 0.15 g (1.5 mmol) of phosphoric acid Followed by stirring for 16 hours.

After completion of the reaction, 100 ml of ethyl acetate was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. After a short pause, the organic layer was separated. Subsequently, the organic layer was washed twice with distilled water and then dried over anhydrous magnesium sulfate. The magnesium sulfate was separated by filtration, the filtrate was dripped into a large amount of n-hexane to reprecipitate, and hexane was removed to remove the precipitate. The obtained precipitate was dissolved in methyl ethyl ketone and recovered. The solvent was distilled off under reduced pressure using this distributor, and vacuum drying was conducted to obtain 13.6 g of the silane compound copolymer (A5).

The silane compound copolymer (A5) had a weight average molecular weight (Mw) of 3,000 and a molecular weight distribution (Mw / Mn) of 1.59.

The IR spectrum data of the silane compound copolymer (A5) are shown below.

Si-Ph: 700 cm ^-1 , 741 cm ^-1 , Si-O: 1132 cm ^-1 , -Cl: 648 cm ^-1

(Production Example 6)

The procedure of Preparation Example 5 was repeated except that the amount of phenyltrimethoxysilane used was changed to 16.7 g (84 mmol) and the amount of 3-chloropropyltrimethoxysilane to be used was changed to 7.15 g (36 mmol) In the same manner, 13.4 g of the silane compound copolymer (A6) was obtained.

The silane compound copolymer (A6) had a weight average molecular weight (Mw) of 3,300 and a molecular weight distribution (Mw / Mn) of 1.59.

IR spectrum data of the silane compound copolymer (A6) are shown below.

Si-Ph: 700 cm ^-1 , 742 cm ^-1 , Si-O: 1133 cm ^-1 , -Cl: 648 cm ^-1

(Production Example 7)

The procedure of Preparation Example 5 was repeated except that the amount of phenyltrimethoxysilane used was changed to 14.3 g (72 mmol) and the amount of 3-chloropropyltrimethoxysilane was changed to 9.54 g (48 mmol) In the same manner, 13.0 g of the silane compound copolymer (A7) was obtained.

The silane compound copolymer (A7) had a weight average molecular weight (Mw) of 3,400 and a molecular weight distribution (Mw / Mn) of 1.61.

The IR spectrum data of the silane compound copolymer (A7) are shown below.

Si-Ph: 699 cm ^-1 , 741 cm ^-1 , Si-O: 1132 cm ^-1 , -Cl: 648 cm ^-1

(Preparation Example 8)

The procedure of Preparation Example 5 was repeated except that the amount of phenyltrimethoxysilane used was changed to 11.9 g (60 mmol) and the amount of 3-chloropropyltrimethoxysilane to be used was changed to 11.9 g (60 mmol) In the same manner, 12.9 g of the silane compound copolymer (A8) was obtained.

The silane compound copolymer (A8) had a weight average molecular weight (Mw) of 3,600 and a molecular weight distribution (Mw / Mn) of 1.63.

The IR spectrum data of the silane compound copolymer (A8) are shown below.

Si-Ph: 700 cm ^-1 , 741 cm ^-1 , Si-O: 1133 cm ^-1 , -Cl: 648 cm ^-1

(Preparation Example 9)

In the same manner as in Production Example 5 except that 4.21 g (24 mmol) of 2-cyanoethyltrimethoxysilane (Azumax) was used instead of 4.77 g of 3-chloropropyltrimethoxysilane in Production Example 5 To obtain 13.5 g of the silane compound copolymer (A9).

The silane compound copolymer (A9) had a weight average molecular weight (Mw) of 2,900 and a molecular weight distribution (Mw / Mn) of 1.58.

IR spectrum data of the silane compound copolymer (A9) are shown below.

Si-Ph: 700 cm ^-1 , 741 cm ^-1 , Si-O: 1131 cm ^-1 , -CN: 2252 cm ^-1

(Preparation Example 10)

In Production Example 9, except that the amount of phenyltrimethoxysilane used was changed to 16.7 g (84 mmol) and the amount of 2-cyanoethyltrimethoxysilane to be used was changed to 6.31 g (36 mmol) , 13.3 g of the silane compound copolymer (A10) was obtained.

The silane compound copolymer (A10) had a weight average molecular weight (Mw) of 3,200 and a molecular weight distribution (Mw / Mn) of 1.64.

IR spectrum data of the silane compound copolymer (A10) are shown below.

Si-Ph: 699 cm ^-1 , 742 cm ^-1 , Si-O: 1131 cm ^-1 , -CN: 2253 cm ^-1

(Preparation Example 11)

In Production Example 9, except that the amount of phenyltrimethoxysilane used was changed to 14.3 g (72 mmol) and the amount of 2-cyanoethyltrimethoxysilane to be used was changed to 8.41 g (48 mmol) , 12.8 g of the silane compound copolymer (A11) was obtained.

The silane compound copolymer (A11) had a weight average molecular weight (Mw) of 3,300 and a molecular weight distribution (Mw / Mn) of 1.62.

The IR spectrum data of the silane compound copolymer (A11) are shown below.

Si-Ph: 699 cm ^-1 , 742 cm ^-1 , Si-O: 1131 cm ^-1 , -CN: 2253 cm ^-1

(Production Example 12)

In Production Example 9, except that the amount of phenyltrimethoxysilane used was changed to 11.9 g (60 mmol) and the amount of 2-cyanoethyltrimethoxysilane was changed to 10.5 g (60 mmol) , 12.3 g of the silane compound copolymer (A12) was obtained.

The silane compound copolymer (A12) had a weight average molecular weight (Mw) of 3,500 and a molecular weight distribution (Mw / Mn) of 1.61.

The IR spectrum data of the silane compound copolymer (A12) are shown below.

Si-Ph: 700 cm ^-1 , 742 cm ^-1 , Si-O: 1133 cm ^-1 , -CN: 2252 cm ^-1

(Example 1)

(TEPIC-PAS B26, epoxy equivalent weight: 137 g / eq) having an isocyanurate skeleton (manufactured by Nissan Chemical Industries, Ltd.) as an epoxy compound (B) 1.5 g of the curing agent (C), 4-methylcyclohexane-1,2-dicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) And 0.375 g of cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride (produced by Mitsubishi Gas Chemical Company, Inc. (alicyclic acid anhydride having a carboxyl group) 0.75 g of a silane coupling agent (hereinafter referred to as &quot; C2 &quot; in the first table and the second table) and 3-triethoxysilylpropylsuccinic anhydride (manufactured by Asmax) , &Quot; D1 &quot; in the second table) was added, and the entire capacity was sufficiently mixed and removed to obtain a curable composition (1) was obtained.

(Examples 2 to 7)

(2) to (7) were obtained in the same manner as in Example 1 except that a silane compound copolymer, an epoxy compound, a curing agent and a silane coupling agent were used in accordance with the following Table 1.

In the following Tables 1 and 2, "B2" represents an epoxy compound having an isocyanurate skeleton (TEPIC-PAS B22 manufactured by Nissan Chemical Industries, Ltd., epoxy equivalent: 179 g / eq).

(Comparative Examples 1 and 2)

(8) and (9) were obtained in the same manner as in Example 1, using the silane compound copolymer, the epoxy compound, the curing agent and the silane coupling agent according to the following Table 1.

(Comparative Example 3)

Epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl (manufactured by Sigma Aldrich) (in Table 2, Table 2 below, &quot;Quot; BF1 &quot;) was used in place of the curable composition (10).

(Comparative Example 4)

A curable composition (11) was obtained in the same manner as in Example 1, except that the silane compound copolymer (A4) obtained in Preparation Example 4 was used instead of the silane compound copolymer (A1) obtained in Preparation Example 1, ).

(Comparative Example 5)

(Hereinafter referred to as &quot; DF1 &quot; in Table 2 below) 0.375 (trade name, manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) Was used in place of the silane coupling agent g, a curable composition (12) was obtained in the same manner as in Example 1.

(Comparative Example 6)

Except that 0.375 g of tetramethyl orthosilicate (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter referred to as "DF2" in Table 1) was used as the silane coupling agent (D1) of Example 1. In the same manner, the curable composition (13) was obtained.

(Example 8)

1.5 g of an epoxy compound having an isocyanurate skeleton (TEPIC-PAS B26, manufactured by Nissan Chemical Industries, Ltd., epoxy equivalent: 137 g / eq) as an epoxy compound (B) was added to 10 g of the silane compound copolymer , 0.38 g of 4-methylcyclohexane-1,2-dicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) as a curing agent (C), and 0.38 g of cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride (Manufactured by Mitsubishi Gas Chemical Company, Ltd.) and 0.38 g of 3-triethoxysilylpropylsuccinic anhydride (manufactured by Ajax) as a silane coupling agent (D) were added, (14).

(Examples 9 to 15 and Comparative Examples 7 to 16)

The curable compositions (15) to (31) were obtained in the same manner as in Example 8, using the silane compound copolymer, the epoxy compound, the curing agent and the silane coupling agent according to the following Table 2.

The cured products of the curable compositions 1 to 31 obtained in Examples 1 to 15 and Comparative Examples 1 to 16 were measured for adhesive force, initial transmittance, and transmittance after heating as follows.

The measurement results are shown in Tables 3 and 4 below.

(Adhesion test)

Each of the curable compositions 1 to 31 was coated on the mirror surface of a square silicon chip of 2 mm so as to have a thickness of about 2 占 퐉 and the coated surface was placed on an adherend (silver plated copper plate) and pressed. Thereafter, it was heat-treated at 180 캜 for 2 hours and cured to obtain an adherend with a test piece. This adherend adhered to the test piece was allowed to stand for 30 seconds on a measuring stage of a bond tester (Series 4000, manufactured by Daisy Ltd.) previously heated to a predetermined temperature (23 ° C, 100 ° C) (N / 2 mm?) Between the test piece and the adherend at 23 占 폚 and 100 占 폚 was measured by applying a stress in the horizontal direction (shear direction) to the adhesive surface at a speed of 200 占 퐉 / s.

(Adhesive heat resistance)

In the adhesive strength test, the case where the adhesive force at 100 占 폚 was 50% or more of the adhesive force at 23 占 폚 was evaluated as?, And the case where the adhesive force was less than 50% was evaluated as?.

(Measurement of initial transmittance)

Each of the curable compositions 1 to 31 was poured into a mold so as to have a length of 25 mm, a width of 20 mm and a thickness of 1 mm and cured by heating at 140 占 폚 for 6 hours to prepare test pieces. The initial transmittance (%) at a wavelength of 400 nm and 450 nm was measured with a spectrophotometer (MPC-3100, manufactured by Shimadzu Corporation).

(Initial transparency)

In the initial transmittance measurement, 80% or more of transmittance at 400 nm was evaluated as &quot; &quot;, 70% or more and less than 80% were evaluated as &quot; DELTA &quot;

(Measurement of transmittance after heating)

Each test piece having the initial transmittance measured was placed in an oven at 150 ° C for 500 hours, and the transmittance (%) of the wavelength 400 nm and 450 nm was measured again. This was taken as the transmittance after heating.

[Heat resistance (transparency after heating)]

In the measurement of the transmittance after heating, the transmittance of 400 nm was evaluated as &quot;? &Quot; when the transmittance was 80% or more of the initial transmittance,? When the transmittance was 70% or more and less than 80%

From the Tables 3 and 4, the cured products of the curable compositions (1 to 7, 14 to 21) of Examples 1 to 15 had a high adhesive strength of 134 N / 2 mm □ or more at 23 ° C, ° C.), an adhesive strength of 58% or more of the adhesive strength at 23 ° C. was maintained, and the adhesive heat resistance was excellent. In addition, the initial transmittance at 400 nm and 450 nm and the transmittance after heating were all high, and the initial transparency and heat resistance (transparency after heating) were excellent.

On the other hand, the cured products of the curable compositions (8, 12, 13, 22, 25 to 27, 30, 31) of Comparative Examples 1, 5 to 7, 10 to 12, The cured products of the curable compositions (9, 23, 28) of Comparative Examples 2, 8 and 13 were lower in adhesive strength and adhesive heat resistance and the cured products of Comparative Examples 3, 4, 9 and 14 The cured product was remarkably poor in heat resistance (transparency after heating).

Claims (13)

(I), (ii) and (iii) in the molecule (A)
[Chemical Formula 1]

Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms and X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group of a hydroxyl group) Is an acyl group protecting group, a silyl group protecting group, an acetal group protecting group, an alkoxycarbonyl group protecting group, or an ether protecting group), and D represents a single bond or a linking group. The linking group is an alkylene group having 1 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An alkenylene group having 2 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An alkynylene group having 2 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An arylene group having 6 to 20 carbon atoms which may be substituted with a cyano group, a nitro group, a halogen atom, an alkyl group, an alkoxy group or an alkylthio group; Or a group formed by combining the arylene group and the alkylene group, alkenylene group, or alkynylene group. R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent.]
(I) and (ii), (i) and (iii), (ii) and (iii) or repeating units (i), (ii) and (iii) A silane compound copolymer having a molecular weight of 1,000 to 30,000,
(B) an epoxy compound having an isocyanurate skeleton represented by the following formula (c-1), (c-2) or (c-3), or a mixture comprising two or more of these compounds ,
(2)

[Wherein E represents any group shown below, and R represents an organic group other than a hydrogen atom or a group having an epoxy ring.
(3)

(Wherein a, b, and c each represent an integer of 1 to 20, and the methylene group may be substituted with an alkyl group.)]
(C) an alicyclic acid anhydride having a carboxyl group and an alicyclic acid anhydride having no carboxyl group, and having a mass ratio of (alicyclic acid anhydride having a carboxyl group): Alicyclic acid anhydride) = 100: 0 to 10: 90, and
(D) a silane coupling agent having an acid anhydride structure represented by the following formula (d)
[Chemical Formula 4]

(Wherein, Y represents a group having an acid anhydride structure, R ^a represents a phenyl group which may have an alkyl group or a substituent having a carbon number of 1 ~ 6, R ^b represents an alkyl group having 1 ~ 6, i is 1 to 3 J represents an integer of 0 to 2, k represents an integer of 1 to 3, and i + j + k = 4).
As a curing composition,
Wherein the content ratio of the components (A), (B), (C) and (D) is in the range of mass ratio of (A) to (B) + (C) + (B) + (C) + (D)] = 90: 10 to 50: 50 and the content ratio of the components (B) (B) + (C): (D) = 90: 10 to 10: 90 in terms of mass ratio. The method according to claim 1,
The silane compound in the copolymer (A), formula: R existing amount of the group represented by ^{1 -CH (X O) -D- (} [R 1 -CH (X O) -D]) and the amount present in R ² ([R ^2]) in a molar ^{ratio, [R 1 -CH (X O} ) -D] of: [R ^2] = 60:40 ~ silane compound copolymer composition of the curable 5:95. (A ') ???????? R ¹ -CH (X ^O ) -D-Si (OR ³ ) _p (X ¹ ) _3-p ?????
Wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms and X ⁰ represents a halogen atom, a cyano group or a group represented by the formula: OG (wherein G represents a protecting group of a hydroxyl group) Is an acyl group protecting group, a silyl group protecting group, an acetal group protecting group, an alkoxycarbonyl group protecting group, or an ether protecting group), and D represents a single bond or a linking group. The linking group is an alkylene group having 1 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An alkenylene group having 2 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An alkynylene group having 2 to 20 carbon atoms which may be substituted with a halogen atom, an alkoxy group, an alkylthio group, or an alkoxycarbonyl group; An arylene group having 6 to 20 carbon atoms which may be substituted with a cyano group, a nitro group, a halogen atom, an alkyl group, an alkoxy group or an alkylthio group; Or a group formed by combining the arylene group and the alkylene group, alkenylene group, or alkynylene group). R ³ represents an alkyl group having 1 to 6 carbon atoms, X ¹ represents a halogen atom, and p represents an integer of 0 to 3.
At least one silane compound (1) represented by the formula
???????? R ² Si (OR ⁴ ) _q (X ² ) _3-q ?????
(Wherein R ² represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent, R ⁴ represents an alkyl group having 1 to 6 carbon atoms, X ² represents a halogen atom, and q represents an integer of 0 to 3 Lt; / RTI &
A silane compound copolymer having a weight average molecular weight of 1,000 to 30,000, which is obtained by condensing a mixture of a silane compound containing at least one kind of silane compound (2)
(B) an epoxy compound having an isocyanurate skeleton represented by the following formula (c-1), (c-2) or (c-3), or a mixture comprising two or more of these compounds ,
[Chemical Formula 5]

[Wherein E represents any group shown below, and R represents an organic group other than a hydrogen atom or a group having an epoxy ring.
[Chemical Formula 6]

(Wherein a, b, and c each represent an integer of 1 to 20, and the methylene group may be substituted with an alkyl group.)]
(C) an alicyclic acid anhydride having a carboxyl group and an alicyclic acid anhydride having no carboxyl group, and having a mass ratio of (alicyclic acid anhydride having a carboxyl group): Alicyclic acid anhydride) = 100: 0 to 10: 90, and
(D) a silane coupling agent having an acid anhydride structure represented by the following formula (d)
(7)

(Wherein, Y represents a group having an acid anhydride structure, R ^a represents a phenyl group which may have an alkyl group or a substituent having a carbon number of 1 ~ 6, R ^b represents an alkyl group having 1 ~ 6, i is 1 to 3 J represents an integer of 0 to 2, k represents an integer of 1 to 3, and i + j + k = 4).
As a curing composition,
The content ratio of the components (A '), (B), (C) and (D) is preferably in the range of (A'): (B) + (C) + (D)] is 90:10 to 50:50, and the content ratio of the components (B), (C) (B) + (C): (D) = 90: 10 to 10: 90 in terms of mass ratio of (D) to (D). The method of claim 3,
The silane compound (1) and the silane compound (2) are mixed in the molar ratio of the silane compound (1) to the silane compound (2) in the ratio of 60:40 to 5:95 Based on the total weight of the curable composition. The method according to claim 1 or 3,
(B) is at least one selected from the group consisting of glycidyl isocyanurate, diglycidyl isocyanurate, tris (2,3-epoxypropyl) isocyanurate, tris (glycidoxypropyl) isocyanurate, tris (? -methyl glycidyl) isocyanurate, or a mixture containing two or more of these compounds. The method according to claim 1 or 3,
In the above (C), the alicyclic acid anhydride of the alicyclic acid anhydride having a carboxyl group is preferably 3-methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl- Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, 3-methylhexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, methylnadic anhydride, 5-norbornene-2,3-dicar Norbornane-2,3-dicarboxylic acid anhydride, methyl-5-norbornene-2,3-dicarboxylic acid anhydride, or methyl-norbornane- Lt; / RTI &gt; acid anhydride. The method according to claim 1 or 3,
In the above (C), the alicyclic acid anhydride of an alicyclic acid anhydride having no carboxyl group is preferably 3-methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl-1,2,3,6 -Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride, hexahydrophthalic anhydride, methylnadic anhydride, 5-norbornene-2,3-dicar Norbornane-2,3-dicarboxylic acid anhydride, methyl-5-norbornene-2,3-dicarboxylic acid anhydride, or methyl-norbornane-2,3-dicarboxylic acid anhydride, Wherein the curing agent is a carboxylic acid anhydride. The method according to claim 1 or 3,
A curable composition which is a composition for optical element fixing. A cured product obtained by curing the curable composition according to any one of claims 1 to 3. 10. The method of claim 9,
Cured article which is optical element fixing material. A method of using the curable composition according to any one of claims 1 to 3 as an adhesive for an optical element fixing material. A method of using the curable composition according to any one of claims 1 to 3 as an encapsulant for an optical element fixing material. delete