TW201141952A - Curable composition, hardened material, and method for using curable composition - Google Patents

Abstract

Disclosed is a curable composition that includes (A) a silane compound copolymer having specific repeating units, (B) an epoxy compound having an isocyanurate skeleton, (C) a curing agent that includes an alicyclic acid anhydride having a carboxyl group, and (D) a silane coupling agent having an acid anhydride structure. Also disclosed are a hardened material formed by hardening the composition and a method for using the aforementioned composition as an adhesive for an optical element fixing material and as a sealing material for an optical element fixing material. With the curable composition, a hardened material can be obtained that does not lose transparency with coloring and has excellent transparency over an extended period of time even when irradiated with high-energy light or when in a high temperature state, and that has high adhesive strength even at high temperatures. The curable composition can be used when forming an optical element fixing material, and in particular can be optimally used as an adhesive for an optical element fixing material and as a sealing material for an optical element fixing material.

Description

201141952 IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. The chemical formula of the levy: 5. If there is a chemical formula in this case, please reveal the best indication of the invention. VI. Description of the invention: [Technical field of the invention] The present invention relates to transparency and heat resistance which can be obtained. Further, a curable composition having a cured product having a high contact force, a composition obtained by curing the composition into a petrochemical material, and a method of using the above composition as an adhesive for an optical element or a mouth material or a package for fixing an optical element. [Prior Art] The conventional 'curable composition' has been variously modified according to the use, and is widely used in the industry as a raw material for an optical component or a prototype, a coating agent, and the like. For example, 'the formation of a cured product excellent in transparency; a composition as a raw material of an optical component, or a coating agent thereof, and a curable composition which forms a cured product having a high adhesion, which is good (d) as an adhesive or Coating agent. In addition, the 'curable composition of the present invention' is a composition for an optical element fixing material such as an adhesive for an optical element fixing material or an encapsulating agent for an optical element cage. 201141952 Body 2: semiconductor laser (10) and other laser or light-emitting diodes == light-emitting elements, photosensitive elements, composite optical elements, optical products for two years, illuminating bees, shorter-wavelength blue or white light components It is used in two places. With the illuminance of the illuminating peaks of the illuminating peaks, there is a large tendency for the heat generation of the element to be improved. In recent years, with the increase in the brightness of the optical element, the optical element is fixed _: the cured product of the composition is exposed to higher-energy light or high-temperature heat generated by light, which causes problems such as cracking and peeling. In order to solve this problem, Patent Document 3 proposes a composition for an optical element fixing material containing a polysilsesquioxane compound as a main component. However, even if it is a cured product of the composition for an optical element fixing material which is a component of the poly-half-stone-oxygen-burning compound which is described in the patent document 3, it is difficult to maintain a sufficient adhesive force, and it is heat-resistant and transparent. Sexual situation. Further, as a composition for optical element encapsulation, an epoxy resin composition using an alicyclic epoxy resin is proposed in Patent Reading 4, and an epoxy resin composition containing a polyhydric alcohol compound is proposed in Patent Document 5. . However, even in the case where the composition is used, it is not possible to sufficiently deteriorate the light resistance deterioration with time, or there is a case where the adhesion is lowered. [Patent Document 1] [Patent Document 1] JP-A-2004-359933 (Patent Document 2) JP-A-2005-328869 (Patent Document 3) JP-A-2006-328231A No. 201141952 [Patent Document 4] Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. In the case of the technology, the problem is to provide a cured product which is excellent in heat resistance and transparency, has a high adhesion, and hardens the composition, and uses the composition. A method of using an adhesive for an optical element fixing material or a packaging material for fixing an optical element. [Means for Solving the Problem] As a result of intensive research to solve the above problems, the inventors of the present invention have found that (A) a specific decane compound copolymer and (B) an epoxy group having an isocyanuric acid S-based skeleton are included. The cured product of the compound and (c) a composition comprising a alicyclic anhydride having a carboxyl group, and a cured product containing a composition of (D) a decane coupling agent having an acid anhydride structure, which can maintain excellent transparency and heat resistance for a long period of time. The present invention can be completed by the fact that it is a cured product having a high adhesion even at a high temperature. Therefore, according to the first aspect of the present invention, the following curable composition of [丨] to [9] can be provided. [1] A curable composition comprising: (A) a calcined compound copolymer which is attached to a molecule, having a lower, er formula (1), (H) and (iii) (i) and (1) and G11)' (ii) and (iii) or (i), (ii) and (iii)

S 4 201141952 篁 average molecular weight is 1, 〇〇〇~3〇, 〇〇〇; (B) % oxygen compound having an isocyanurate-based skeleton; (C) hardener comprising an alicyclic ring having a carboxyl group Anhydride and other alicyclic acid needles; and (D) a sand-burning coupling agent having an anhydride structure:

W (9) (Hi) where R represents a halogen atom or a carbon number of 1 to 6, and represents a halogen atom, a cyano group or a group represented by the formula: 0G, wherein G represents a protecting group of a hydroxyl group, D represents a single bond or a linker, and R2 represents a phenyl group of a carbon number or a phenyl group which may have a substituent. [2] The curable composition according to [1], wherein the above-mentioned (a) is a total of 1 in the form of a group represented by the formula: f-CHCXy-D- ([RLCHCXO- The molar ratio of D]) to R2 ([R2]) is [f-CiUXO-D]: [R2] = 60: 40~5: 95 decane compound copolymer. [3] The curable composition according to [1] or [2] wherein the ratio of the components (A), (B), (C), and (D) is (A) and [(β) ) + (c) + (D)] mass ratio to (A) : [(BH(C) + (D)] = 90 : 1〇~5〇: 5〇. 201141952 [4 ] - Hardenability a composition comprising: (A') a decane compound copolymer, which is comprised of the formula (丨): R1-(:Η(Χβ)-ΐ)-υ(〇κ3)ρ(χ1)3_ρ And a mixture of at least one of the decane compound (1) and a mixture of the compound of the formula (2): at least one of the decane compounds represented by R2Si(〇R4)q(x2)3_q, having a weight average molecular weight of 1,000- 30, 〇〇〇; (B) an epoxy compound having an isocyanurate-based skeleton; (C) a hardener comprising an alicyclic anhydride having a carboxyl group and other alicyclic anhydrides; and ' (D: a U-alkane coupling agent having an anhydride structure: wherein R 1 represents a hydrogen atom or an alkyl group of a carbon number, an anthracene, a cyano group or a group represented by the formula: GG. In the formula, G is represented by: The protection of the base D represents a single bond or a linker, and the r3 system represents The alkyl group of the carbon number B is represented by an atomic number of the p-type atom, and the p2 is an alkyl group having a carbon number of 1 to 20 or a stupid group which may have a substituent, and the y is an alkyl group having a carbon number of [5] The hardening composition according to [4], wherein the (a,) decane compound copolymer is a decane compound (1) and a decane compound. (2) with = ear ratio, [Astraestane compound (1)]: [decane compound (2)] = 6〇: 4〇~5: % of the ratio of condensation. [6] as [4] or [5] The curable composition according to the above, wherein the content ratio of the components (A,), (8), (C), and (8) is the amount of (a,) and UBH(c)+(D)] Ratio to (A'): [(B) + (c) +(8)]=9〇':,

S 6 201141952 10~50 : 50 . [7] The curable composition according to [1] or [4], wherein the above-mentioned (b), (C), and (D) have a content ratio of [(b) + (C)] and ( D) mass ratio, to [(B) + (C)]: (D) = 90: 10~10: 90. [8] The curable composition according to [1], wherein the hardened material of the above ([) is selected from one or more selected from the group consisting of an alicyclic acid anhydride having a carboxyl group and another alicyclic acid anhydride. The composition has a mass ratio of (alicyclic anhydride having a carboxyl group): (other alicyclic anhydride) = 100: 〇~10: 90. [9] The curable composition according to [1] or [4], which is a composition for a light element fixing material. According to the second aspect of the present invention, the cured products of the following [10] and [u] can be provided. [10] A cured product obtained by hardening [a hardening composition according to [4] or [4]. [11] The cured product according to [10], which is a light 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 in [12] or [13] below. [12] A method of using the curable composition described in [i] or [4] as an adhesive for an optical element fixing material. [1 3] The curable composition according to [1] or [4] is used as an encapsulant for an optical element fixing material. [Effect of the Invention] According to the curable composition of the present invention, even if it is irradiated with a high-energy light in an If-shaped or a south-temperature state, it is not colored and the transparency is lowered, and the long-lasting-excellent transparency can be obtained. It is a 201141952 hardened material which has a high adhesion force at a high temperature. The curable composition of the present invention, in particular, can be suitably used for forming an optical element fixing material for use as an oxygen-stopping member (four) mounting #1. The adhesive for fixing a part, and the following describes the method of using the D curable composition, 2) the cured product, and 3) the curable composition. 1) Curable composition The curable composition of the present invention comprises: (A: a sulfonated compound copolymer which is in a molecule and has the following formula, (ii) and (iii) The repetitive unit of (^ and ^ soil), (〇 and (iii), (ii) and (iii) or (i), (ii) and (iii), the weight average molecular weight is 1, 〇〇 〇~30,000; (B) an epoxy compound having an isocyanurate-based skeleton; and (C) a hardener comprising an alicyclic acid anhydride having a carboxyl group, and (D) a decane coupling agent having an anhydride structure:

C

/

D

(iii)

-Si—0-O i -Si

D CH——X° R1 0) (ϋ) s 201141952 where R is a hydrogen atom or an alkyl group having a carbon number of 6 and χ is a halogen atom, a cyano group or a group represented by the formula: 〇G. In the formula, g is a sulfhydryl group which represents a hydroxy group, and D represents a single bond or a linker, and R2 represents a phenyl group of a carbon number or a phenyl group which may have a substituent. (A) decane compound copolymer The curable composition of the present invention contains, as component (A), (i) and (i) among the reversing units represented by the above formulas (〇, (ii) and (iii) Ii), (i) and (iii), (ii) and (iii) or (i), (ii) and (iii) the repeating unit, the weight average molecular weight is L 〇〇〇~3〇, 〇〇〇之a decane compound copolymer (hereinafter referred to as "the decane compound copolymer (A)"). The sulphur compound copolymer (A) ' may have (i), (丨丨), (alumina), respectively. One of the repetitive units shown, or two or more. In the formula (i Mi ii), 'R1 is a hydrogen atom or a decyl group of carbon number 6, preferably a hydrogen atom. The carbon number is 1 to 6 represented by R1. The alkyl group may, for example, be an alkyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an isobutyl group, a second butyl group, a n-pentyl group or a n-hexyl group. a dentate atom such as a atom, a gas atom, a bromine atom or a quinone; a cyano group or a group represented by the formula: 0 G. The G system represents a protecting group of a hydroxyl group. 'A conventional protecting group known as a protecting group for a hydroxyl group is exemplified. For example, 'anthraceyl protecting group; tridecyl decyl group, triethyl decyl group, _ butyl dimethyl decyl group, Tributyl diphenyl fluorenyl and the like, such as: lysine & :. protecting group; trimethoxymethyl group 'methoxy group oxy fluorenyl group, 1 - gas group B 201141952 group, tetrahydropyridyl An acetal protecting group such as a fluoren-2-yl group or a tetrahydrofuran-2-yl group; an alkoxycarboxy group protecting group such as a third butoxy carboxy group; a methyl group, an ethyl group, a tert-butyl group, and an octyl group Base, trisylmethyl, nodal, p-methoxy

An ether-based protecting group such as a thiol group, a fluorenyl group, a tris-methyl group or a dimethylene group. Among these, G is preferably a thiol-based protecting group. The X 醯 group protecting group, specifically, is represented by the formula: _c( = 〇)RS. In the formula, R5 represents an alkyl group of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a second butyl group, a t-butyl 'n-pentyl group or the like. Or may have a stupid base. The substituent of the phenyl group which may have a substituent represented by R5 may, for example, be a methyl group, an ethyl 'n-propyl group, an isopropyl group, an n-butyl group, a second butyl isobutyl group, a third butyl group or a n-pentyl group. An alkyl group such as n-hexyl, n-heptyl, n-octyl or isooctyl; a acene atom such as a fluorine atom, a gas atom or a bromine atom; or an alkoxy group such as a methoxy group or an ethoxy group. Among these, it is easy to handle by hand, and a cured product having high adhesion is obtained, and is selected from a group represented by a gas atom and having the formula: 〇G (wherein, G is a protecting group of a fluorenyl group). The base of the aryl group is preferably selected from the group consisting of a gas atom, an ethoxy group and a cyano group, and particularly preferably an ethoxy group. D represents a single bond or a linker. The linking group may be a divalent organic group which may have a substituent. The carbon number of the organic group is preferably from 1 to 2 0, more preferably from 1 to 1 Torr. a divalent organic group which may have a substituent, and, for example, a sub-base group which may have a substituent, a sub-base group which may have a substituent, a sub-fast group which may have a substituent, an arylene group which may have a substituent, Substitutable (sub-alkyl,

A divalent group composed of a combination of S 10 201141952 alkenylene group or alkynylene group and an arylene group which may have a substituent. An alkylene group which may have a substituent alkylene group, and may have a carbon number of an anthranylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group or the like. 〜20, preferably an alkylene group having a carbon number of 1 to 1 Å. The alkenylene group which may have a substituent alkenylene group, and the alkenylene group having a carbon number of 2 to 2 Å, such as an ethyleneylene group, a propylene group, a butenylene group, a pentenylene group, or the like, may have a carbon number of 2 to 2 The alkenylene group of 10 is preferred. The alkynylene group having an alkynylene group having a substituent may, for example, be an alkynylene group having 2 to 20 carbon atoms such as an ethynylene acetylene group, and preferably an alkynylene group having 2 to 1 carbon atoms. The arylene group having a substituent arylene group may, for example, be an arylene group having a carbon number of 6 to 2 Å, such as an o-phenylene group, a m-phenylene group, a p-phenylene group or a 2,6-naphthylene group. It is preferred to use an arylene group having a carbon number of 6 to 10. Examples of the substituent of the above alkylene group, alkenylene group, and alkynylene group include an atomic atom such as a fluorine atom or a chlorine atom; an oxy group such as a methoxy group or a oxy group; and a methylthio group or an ethylthio group. An alkylthio group; an alkoxycarboxy group such as a methoxycarboxy group or an ethoxycarboxy group; and the like. Examples of the substituent of the above arylene group include a halogen atom such as a cyano group, a nitro group, a fluorine atom, a gas atom or a bromine atom; an alkyl group such as a methyl group or an ethyl group; and an alkoxy group such as a methoxy group or an ethoxy group. An alkylthio group such as a thiol group or an ethylthio group. The substituents may be bonded to any of the groups of the alkylene group, the sub-base group, the sub-fast group and the arylene group, and may be the same or different plural bonds. a divalent group which may be 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 of 11 201141952, and may have a substituent which may have a substituent At least one of an alkyl group, an alkenylene group, or an alkynylene group, a group bonded in series with at least one of the above-mentioned arylene groups having a substituent. Specifically, a base represented by the following formula can be mentioned.

(?Η2)2

Tian j忖 Dan shoulder still receives the hardened material of the force, with the carbon number of 1 ~ 1 0 of the sub-form of #坑丞马佳, the slave number 丨 ~ 6 alkylene is better, to methylene or Asian Ethyl is especially preferred. In 弋(·)(iii), r is a phenyl group of a carbon number or a phenyl group which may have a substituent. The alkyl group of carbon number represented by R2 may, for example, be methyl, ethyl, n-propyl, isopropyl, n-butyl, flute _ J 丞, first butyl, isobutyl, tert-butyl , n-pentyl, n-hexyl, phenyl, octyl, isooctyl, n-decyl, n-decyl, n-dodecyl and the like. The substituent of the phenyl group which may have a substituent in the form of R may, for example, be an alkyl group, an ethyl group, a n-propyl group, a isopropyl isopropyl group, a second butyl group, an isobutyl group, a second butyl group, or the like. An alkoxy group such as a n-pentyl group, a ruthenium group, a n-heptyl group, an n-octyl group or an isooctyl group; an alkoxy group of a methoxy group; an ethoxy group of an ethoxy group; a fluorine atom; a gas atom; Prime atoms and so on.

S 12 201141952 Specific examples of the stupid group which may have a substituent represented by R2 may, for example, be a phenyl group, a 2-chlorophenyl group, a 4-methylphenyl group, a 3-ethylphenyl group or a 2,4-difluorenyl group. Stupid base, 2-decyloxyphenyl and the like. The molar amount of the decane compound copolymer (A)' represented by the formula: r1 - CH(X°)-D- ([F-CIKXy-D]) and the amount of R2 ([R2]) Than, [R'-CiKX11)-!)] : [R2] = 60: 40~5: 95 is better, with 50: 50~5: 9 5 better 'to 5 0 : 5 0~1 0 : 9 0 is especially good. Within this range, a cured product excellent in transparency and adhesion and excellent in heat resistance can be obtained. The amount represented by the formula: R-CH(X°)-D - and the amount of R2 can be quantified, for example, by measuring the nmr spectrum of the decane compound copolymer (A). The Shi Xiyuan compound copolymer (A) may be any copolymer of a random copolymer, a block copolymer, a graft copolymer, an interactive copolymer or the like, but is particularly preferably a random copolymer. The weight average molecular weight (Mw) of the zephyr compound copolymer (A) is in the range of 1,000 to 30,000, and is in the range of 丨'500 to 6 Torr. By the above range, it is possible to obtain a cured product excellent in handleability and excellent in heat resistance. The weight average molecular weight (M w ) can be obtained, for example, from a standard polystyrene equivalent value of gel permeation chromatography (GPC) using tetrahydrofuran (T H F ) as a solvent. The molecular weight distribution (Mw/Mn) of the decane compound copolymer (A) is not particularly limited. Usually, it is U~3.〇, and the range of i•b 2〇 is preferable. By this range, a cured product excellent in adhesion and heat resistance can be obtained. The decane compound copolymer (A) may be used singly or in combination of two or more. 13 201141952 Polyepimane oxyalkylene compound copolymer (A) with a ladder structure.

The polytetradecyloxy compound was confirmed by infrared absorption spectrum measurement of the ladder product. The structure may be, for example, by inverse 疋, X-ray diffraction measurement, or NMR (A) component, or may be included in the curable composition of the present invention: (A') Formula (1): At least one of the decane compound (1) represented by "CH(xvD_Si(10)3) ρ(χ1)3ρ, and at least one of the calcined compound (2) represented by R2Si(OR4)q(X2)3.q A cation of a compound of a smelting compound is condensed to obtain a weight average molecular weight of 1, _~30, which is a copolymer of cerium oxide (hereinafter referred to as "decane compound copolymer α,"). . Wherein R1 represents a hydrogen atom or an alkyl group having a carbon number id, and χ() represents a functional atom, a cyano group or a group represented by the formula: GG, wherein G represents a protecting group of a thiol group, D represents a single bond or a linker, y represents an alkyl group having a carbon number, and X1 represents a pixel atom, ? An integer of 3~3; R2 represents an alkyl group having 1 to 20 carbon atoms or a phenyl group which may have a substituent, R4 represents an alkyl group having 16 carbon atoms, X2 represents a halogen atom, and q represents a 〇~3 The integer, decane compound copolymer (A) is preferably a decane compound copolymer (A,). [Dream compound (1)] The decane compound (1) is a compound represented by the formula (1): R1_CH(XC)_D_Si(〇R3)p(X)3-p. By using the stone smelting compound (1), it can be obtained by hard

S 14 201141952 A decane compound copolymer having good transparency and adhesion after the formation. In the formula (1), R1 represents a hydrogen atom or an alkyl group having a carbon number of i to 6, preferably a hydrogen atom. Specific examples thereof include those in which the decane compound copolymer (VIII) is exemplified as R1. The X system in () represents a functional atom such as a fluorine atom, a chlorine atom, a bromine atom or an argon atom, a cyano group or a group represented by the formula: QG, (wherein, the G series table

Show the protecting group of the hydroxyl group. ) ° indicates a single bond or a linker. Take X. The specific example of the case where D is represented by the decane compound copolymer (1) is exemplified as X° and D, respectively. R3 represents a C Η alkyl group such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a t-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group or a n-hexyl group. The X series shows a non-fluorine atom, a gas atom, a desert atom, a broken atom, and the like. The Ρ indicates an integer from 0 to 3. When Ρ is 2 or more, 叱 may be the same or different. Further, when (3-p) is 2 or more, X1 may be the same or different from each other. Specific examples of the compound (1) can be exemplified by chloromethyltrimethoxy decane, methylenetriethoxy oxacyclohexane, 2-chloroethyltripropoxy oxacyclohexane, and 2-diethyl sulphate. Oxygen (tetra), 3-vapor propyl trimethoxy ketone, 3- propyl propyl triethoxy decane, 3' propyl propyl tripropoxy decane, 3 ' propyl propyl tributoxide oxylate, 3- (4) bistrimethoxy ketone, 3 _ propyl propyl oxy _, 3- propyl propyl tripropoxy zebra, 3- propyl propyl tributoxide, 3 - fluoropropyl trimethoxy基石夕院, 3-气丙三ethoxy money, methoxypropyl tripropylene 15 201141952 oxydecane, 3-fluoropropyl tributoxy decane, 3_molyl tridecyloxy decane, 2 - gas ethyl trimethoxy decane ' 3-chloropropyl trimethoxy decane, 4- butyl tributoxy oxazepine, 5- gas pentyl trimethoxy sulphur, 2- propyl propyl trioxane Base decane, 3-ox-3-ethyl propyl propyl tridecyloxy sylvestre, 3-ox-3-oxooxycarbonylpropyltrimethoxy decane, o-(2-hydroxyethyl)phenyl tripropoxy Base decane, m-(2-chloroethyl)phenyltripropoxydecane, p-(2-cycloethyl)phenyltripropoxy Alkane, p-(2-fluoroethyl)phenyltripropoxydecane, etc., a trialkyloxydecane compound of the same atom; gas methyl trioxane, bromomethyl bromide, 2- Chloroethyl dimethoxy methoxy decane, 2-bromoethyl diethoxy ethoxy decane, 3- propyl propyl trioxane ' 3- propyl tribromo decane, 3- propyl propyl di oxooxy矽 ' ' 3- propyl propyl diethoxy ethoxy decane, 3- propyl propyl dimethoxy decane, 3- propyl propyl diethoxy decane, 3-bromopropyl di ethoxy decane, 3-bromopropyltribromodecane, 3-bromopropyltrichlorodecane, 3-bromopropyldimethoxy fluorene, 3-fluoropropyl tri-gas, x-fluoropropyl dimethyl Oxyzetan, 3-fluoropropyldimethoxymethoxydecane, 3-fluoropropyl gas diethoxy decane, 3-Epropyl trioxane, 4-cyclobutyl diethoxy decane, X such as 3-chloro-n-butyl gas diethoxy decane, 3- gas-3-ethyl propyl propyl di ethoxy decane, 3- gas-3-methoxycarbonyl propyl tribromo decane. a compound of a halogenated porphyrin compound; cyanomethyltrimethoxydecane, cyanomethyltriethoxydecane, cyanoethyltrimethoxy decane, 2-cyanoethyltrimethoxy Decane, 2-cyanoethyltriethoxydecane, 2-cyanoethyltripropoxydecane, 3-cyanopropyldimethoxydecane, 3-cyanopropyltriethoxydecane, 3_cyanopropyl

S 16 201141952 1,3-trimethoxydecane, 3-cyanopropyl tributoxy decane, 4-cyanobutyltrimethoxy decane, 5-cyanopentyltrimethoxydecane, 2-cyanopropyl Trimethoxy decane, 2-(cyanomethoxy)ethyltrimethoxydecane, 2-(2-cyanoethoxy)ethyltrimethoxynonane, o-(cyanomethyl)phenyl three Propoxy decane, m-(cyanomethyl)phenyl trimethoxy decane, p-(cyanomethyl) phenyl triethoxy decane, p-(2-cyanoethyl) phenyl trimethoxy decane Xt is a cyanotrial alkoxy oxirane compound; cyano decyl triclosan, cyanomethyl bromide dioxate, 2-cyanoethyl dichloromethoxy fluorene Burned, 2-cyanoethyl diethylene ethoxylated, 3-cyanopropyl trioxane, 3-cyanopropyltribromodecane, 3-cyanopropyldichlorodecyloxydecane, 3 -Cyanopropyldichloroethoxy decane, 3-cyanopropyl chlorodimethoxy decane, 3-cyanopropyl chlorodiethoxy decane, 4-cyanobutyl dimethyl dimethoxy decane , 3-cyano-n-butyl gas diethoxy decane, 2_(2-cyanoethyl)phenyl Chlorodecane, 2-(2-cyanoethyl)ethylbromodiethoxydecane, 2-(2-cyanoethyl)ethyldipropoxylate Shixia, o-(2-cyanoethyl) Phenyl trioxane, m-(2-cyanoethyl)phenyl dimethoxy bromide, p-(2-cyanoethyl)phenyl dimethoxy chlorodecane, p-(2-cyanoethyl) a sulfonium halide compound of the phenyl group, which is a cyano group; 3-ethoxypropyl propyl trimethoxy decane, 3 ethoxypropyl propyl triethoxy decane , 3-ethoxypropyl propyl tripropoxy decane, 3 ethoxypropyl propyl tributoxy decane, 3-propoxy propyl tributoxy decane, 3 propyl methoxy propylene Triethoxy decane, 3_benzylidene propyl trimethoxy decane' 3-abidomethyloxypropyl triethoxy decane, 3 - benzoyloxy: bispropoxy Decane, 3-benzyloxypropyl tributoxy decane, I trimethyl 17 201141952 hydrazinyloxyethyl trimethyl decane, 3-triethyl methoxy propyl triethoxy sylvestre, 3 -(2~tetrahydropyranyloxy)propyltripropoxydecane, 3_(2-tetrahydro 0-methoxy)propyltributyl Oxydecane, 3-methoxymethyloxypropyltrimethoxy zeoxime, 3-methoxyethoxymethyloxypropyltriethoxydecane, 3-mono(1-ethoxyethyloxy) Propyltripropoxydecane, 3-(t-butoxycarbonyloxy)propyltrimethoxyoxydecane, 3-tert-butoxypropyltrimethoxydecane, 3-methoxypropyltriethyl The X° of oxydecane, 3-triphenylphosphonium oxypropyltriethoxy sulphide, etc. is the above formula: the decyloxydecane compound represented by 〇G; 3-ethyloxypropane Base three gas stone Xizhu, 3-ethoxypropoxypropyltribromide, 3-ethyloxypropyldichloromethoxy decane, 3_ethoxypropyl propyl diethoxy ethoxy decane , 3-ethoxypropyl propyl dimethoxy decane, 3 ethoxypropyl propyl diethoxy decane, 3-benzyl methoxy propyl trioxane, 3-trimethyl hydrazine Oxypropyl propyl dimethoxy decane, 3-triethyl methoxy propyl dimethoxy methoxy decane, 3-(2-tetrahydro tonyloxy) propyl chlorodiethoxy decane, 3 -(2-tetrahydrofuranyloxy)propyl dioxyethoxy decane, 3-methoxyoxypropyltribromodecane, 3-methyl Ethyloxymercaptooxypropyl trioxane, 3-(1-ethoxyethyl)propyl dimethoxydecane, tert-butoxycarbonyloxypropyldichloromethoxydecane , 3_t-butoxypropyl chloride, diethylene ethoxylate, 3-triphenylmethoxypropyl diethoxy ethoxy decane, 3-ethoxy propyl smectite, etc. X. It is a compound of the above formula: dent G, which is represented by 〇G. These brothel compounds (1) may be used in combination of two or more types. Among these, the compound (1) is more excellent in the available

S 18 201141952 The compound of the m (tetra) atom, the trioctyloxy group, the trialkyloxydecane compound which is a cyano group, or the trialkyloxydecane compound wherein r is a group represented by the above formula: a three-compartment oxy compound having a 3'-gas propyl group, a three-yard oxy group having a 3-ethoxypropyl group: a compound of the compound, and a compound of a compound of 2-cyanoethyl The class, or a trialkoxydecane compound having a 3-cyanopropyl group, is more preferred. [decane compound (2)] The decane compound (2) is a decane compound represented by the formula (1): r2Si (〇R4)q(x2)3 q . In the formula (2), R2 represents an alkyl group having a carbon number or a phenyl group which may have a substituent. Specific examples are exemplified as the decane compound copolymer (A) as R2. The R group represents an alkyl group having 1 to 6 carbon atoms which is the same as the above R3. X2 represents the same dentate atom as the above X1. The Q series is not 0 to 3 - integer. When Q is 2 or more, OR4 may be the same or different from each other. Further, when (3-Q) is 2 or more, X2 may be the same or different from each other. Specific examples of the decane compound (2) include mercaptotrimethoxydecane, decyldiethoxydecane, ethyltrimethoxydecane, ethyltriethoxydecane, and n-propyldimethoxyoxydecane. , n-butyltriethoxydecane, isobutyltrimethoxydecane, n-pentyltriethoxydecane, n-hexyltrimethoxyoxane, isooctyldiethoxydecane,dodecyltriazine Alkyl dioxy oxymethane compounds such as oxydecane, methyl monomethoxyethoxy decane, decyl diethoxy methoxy decane, etc.; 19 201141952 methyl chlorodimethoxy decane, A Dichloromethoxy decane, decyl gas diethoxy decane, ethyl gas dimethoxy decane, ethyl dichloro methoxy oxime, n-propyl chloro decyl oxide, n-propyl Alkyl methoxylated alkoxy decanes such as dimethoxy methoxy sulphate; methyl sulphate, methyl tribromide, ethyl sulphate, ethyl tribromo decane, positive a propyl trioxane, an alkyla-tridecane compound; a stupyl trimethoxy decane, a 4-methoxyphenyl trimethoxy decane, a 2-gas phenyl tri Oxydecane, phenyltriethoxydecane, 2-decyloxyphenyltriethoxydecane, phenyldimethoxyethoxysilane, phenyldiethoxymethoxydecane, etc. may have Substituted phenyltrialkoxydecane compound phenyl gas dimethoxy decane, phenyl dimethoxy methoxy decane, phenyl methoxy ethoxy decane, phenyl gas diethoxy decane, benzene a phenyl-terminated alkoxy decane compound having a substituent such as a phenyl ethoxy decane; phenyl trioxane, phenyl tribromodecane, 4-methylphenyl trioxane, 2-gas A phenyl tripled compound compound which may have a substituent such as phenyl trioxane or 2-ethoxyphenyl trioxane. These decane compounds (2) may be used alone or in combination of two or more. [A mixture of decane compounds] A mixture of decane compounds used in the production of the decane compound copolymer (A,) can be a mixture of a decane compound (丨) and a decane compound (2).

20 S 201141952 Oral, it is further possible to include a mixture of other decane compounds in a range which does not hinder the object of the present invention, but a mixture of a decane compound (1) and a decane compound (?) is preferred. The ratio of the compound of Shi Xixuan compound (1) to the compound of decane (2) is preferably [Moxi-smelting compound (1)] ··[decane compound] = 60 : 4〇~5 : 95 50: 50~5: 95 is better, with 50: 50~10: 90 especially good. The method of condensing the mixture of the above-mentioned Shi Xi Xuan compound is not particularly limited, and the decane compound (1), the decane compound (2), and other desired decane compounds are dissolved in a solvent, and a predetermined amount of contact is added. Medium, a method of stirring at a given temperature. The catalyst used may be either an acid catalyst or a base catalyst. The acid catalyst may be an inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid; an organic acid such as toluene acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic acid or trifluoroacetic acid. The catalyst can be exemplified by trimethylamine, triethylamine, lithium diisopropylamide, lithium bis(trimethylsulfonyl)amine, pyridine, hydrazine, 8-diazabicyclo[5. 4 〇] Organic bases such as undec-7-ene, aniline, mercaptopyridine, 1,4-diazabicyclo[2.2.2] octane, imidazole, etc.; tetramethylammonium hydroxide, tetraethyl hydride, etc. Organic salt hydroxide; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium butoxide, potassium butoxide; metal hydrides such as sodium hydride, calcium hydride, etc.; sodium hydroxide, potassium hydroxide, hydrogen A metal hydroxide such as calcium oxide; a metal carbonate such as sodium carbonate, potassium carbonate or magnesium carbonate: a metal hydrogencarbonate such as sodium hydrogencarbonate or potassium hydrogencarbonate. Among these, the catalyst used is preferably acid catalyst. The inorganic acid is better than 201141952. The amount of catalyst used is - the total molar amount of the smoldering compound, usually from 0.1 mol% to lOmoi%, in the range of im 〇 1% 〜 5 m 〇 1%. The solvent to be used can be appropriately selected depending on the type of the decane compound and the like. Examples thereof include aromatic hydrocarbons such as water, benzene, methyl bromide, and xylene; esters of methyl acetate, ethyl acetate, propyl acetate, and methyl propionate; acetone, methyl ethyl ketone, and mercapto isobutyl ketone; A ketone such as cyclohexanone; an alcohol such as decyl alcohol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, second butanol or tert-butanol. The solvent may be used singly or in combination of two or more. Among them, water, an aromatic hydrocarbon, and a mixed solvent thereof are preferred, and a mixed solvent of water and toluene is particularly preferred. When water and toluene are used, the ratio of water to toluene (volume ratio) is 1: 9~9: ! is better, with 7: 3~3: 7 better. The solvent is used in an amount of 1 liter equivalent of the solvent, and the total molar amount of the decane compound is usually 0.1 mol of WOmol, more preferably 〇 5m〇w〇m〇1. The temperature at which the decane compound is condensed (reacted) is usually in the range of from 〇t to the boiling point of the solvent to be used, preferably in the range of 2 Torr to 1 Torr. When the reaction temperature is too low, the progress of the condensation reaction may be insufficient. On the other hand, when the reaction temperature is too high, it is difficult to suppress gelation. The reaction is usually completed in 3 to 20 hours. When an acid catalyst is used, when an alkaline catalyst 1 such as an aqueous solution of sodium argon carbonate is added to the reaction solution, an acid such as hydrochloric acid is added to the reaction solution to neutralize the salt which will be produced at this time. By over or

S 22 201141952 Removal by water washing, etc., the desired decane compound tool can be obtained. (B) Epoxy compound having an isocyanurate group skeleton 2. The curable composition of the invention includes an epoxy compound having a gas urethane frame (hereinafter, it is referred to as "product of the animal" as the component (8). There is a case where it is called &oxy compound (8).) The curable composition of the present invention contains a cured compound which is excellent in heat resistance and transparency even after the heat history of the epoxy compound (8). As the epoxy compound (B), as long as it is in the skeleton (in the following (4), the towel has a different type of urethane nozzle, the U-form is not bonded), and has an epoxy:, 'no special limited. Further, in the isocyanuric acid sulphate skeleton (the tautomers (isoisouric acid §) can be present as described below], the system represents a bonding bond.) 'Only with the skeleton An epoxy compound, which is contained in the epoxy compound (B) used in the present invention. Also 0>

• N

丫 N Ο \Ν, Ν Ο (c)

°\ (C) wherein the epoxy compound (8) is bonded to the isocyanurate tq oxime as shown in the following formula (C-1) to (c_3), and the nitrogen atom of the 1, 3, and 5 positions of U 曰Chlorine Atom - A compound substituted with a group having an epoxy ring (8) is positive: 〉, 23 201141952

E

Ο (c-1)

l -X' » (c-3) X , E means a group having an epoxy ring, R 俜 I _ - an organic group or the like having a K group and a hydrogen atom, and having a radical other than the group of the % ring base. The group having an epoxy group (8)' may, for example, be -L,.

CH2—CH—^CH2 Ο

An alkyl group such as a methyl group or an ethyl group may be substituted. Specific examples of the epoxy compound (8) are: from the viewpoint of obtaining a cured product having a high adhesion, glycidyl isocyanurate, diglycidyl isocyanurate, and tris(2, 3- Epoxy propyl) isocyanurate urethroate, tris (glycidol)

a propyl group, a heterologous vinegar, a tris((2-methyliso-I)-hydrazinyl)-isocyanurate, a mixture of two or more of these compounds, etc. Use a commercially available ring with an isocyanuric acid vinegar skeleton

S 24 201141952 Oxygen compounds (for example, trade names: TEPIC_S, TEPIC-PAS B22, trade name: TEPIC-PAS B26, etc., all manufactured by Daicel Chemical Industries, Ltd.) are used as the epoxy compound (B). The blending amount of the epoxy compound (B) is not particularly limited, and from the viewpoint of obtaining a cured product having a higher adhesive force, the epoxy equivalent is preferably 5 〇 to 3 〇〇 g/eq, and 100 to 200 g. /eq is especially good. Further, the epoxy equivalent is a value measured in accordance with JIs K 7 2 3 6 : 2000. (C) Curing Agent The curable composition of the present invention contains a curing agent having a carboxy alicyclic acid anhydride (hereinafter referred to as "the curing agent (c) j). (c) component. The hardening of the present invention. The composition contains a hardener (c), and a cured product excellent in heat resistance is obtained. The alicyclic acid anhydride having a carboxyl group is an acid anhydride having at least one carboxyl group-substituted lipid raft structure. The alicyclic structure may be a saturated ring. a hydrocarbon (cycloalkane) structure, an unsaturated cyclic hydrocarbon (cycloalkenyl, cycloalkyne) structure, etc. The alicyclic acid anhydride may, for example, be 3-methyl-me-tetrahydrophthalic anhydride or 4-mercapto-1. 2, 3, 6-tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride, hexahydrogen O-phthalic anhydride, methyl nadic anhydride, 5-bicycloheptene-2 2 dicarboxylic anhydride, bicycloheptene-2, 3-biscarboxylic anhydride, mercapto X ^ heptane-2,3-biscarboxylic anhydride , methyl bis bicycloheptene 2,3 bis carboxylic anhydride, etc. Carboxy, optionally substituted alicyclic anhydride alicyclic structure at any position, the position of substitution or the number of substituted carboxyl groups is not particularly limited Among these, hexahydrophthalic anhydride is substituted for carboxymei~hard hydrazine % hexane 25 201141952 -1,2,4-tricarboxylic acid-1,2 anhydride, cyclohexane-i 9 machine i 2,3-tricarboxylic acid_1>2 anhydride is preferred, and cyclohexane-1,2,4-tricarboxylic acid-1 2 is 4*. 1Z Xuan is particularly preferred. The structure may be any of the isomers. The alicyclic acid anhydride having a carboxyl group may be used as a seed, or may be used in combination of two or more. The hardener (C) may further contain other hardeners. The hardener (C) can be mentioned as follows: not only the secrets are good + the alicyclic acid anhydride having a carboxyl group (hereinafter referred to as "other alicyclic acid anhydride" 吼or"), the fatty acid of the polysebacic anhydride, and the aliphatic Amine-based hardening sword, fat sputum, sputum, sputum, sulphuric acid, hardener, grade 2 or 3 amine hardener, aromatic amine hardener, _ « B ^ (1) 虱 makeup, boron difluoride Amine salt, imidazole compound, and the like. Other hardeners may be used singly or in combination of two or more. Other hardeners are preferably other alicyclic acid anhydrides obtained from a cured product having a high adhesion even at a high temperature. Other alicyclic acids may be the same as those of the above-mentioned alicyclic acid oxime which has a slow-acting alicyclic acid. Among them, a 3-methyl-hexahydrophthalic acid needle and a "yl-hexahydrophthalic acid oxime are preferred. -Methyl-hexahydrophthalic acid is particularly preferred. The η hardened material (C) is preferably composed of two or more kinds of alicyclic acid needles having a slow base and other alicyclic acid anhydrides, and the mass ratio thereof is a nucleating nucleic acid needle: Other alicyclic anhydrides = 100: 0~10: 9 〇 good, to 50: 50~1 〇: 9 〇 better. (D) Dream Burning Coupling Agent The curable composition of the present invention, & contains: a coupling agent having a citric acid needle structure (hereinafter, referred to as "residual coupling agent (8)").

S 26 201141952 into a knife. The curable group -τα^ of the present invention can be phase-separated (white turbid), permeable, and contains a decane coupling agent (D). It has excellent uranium and high arsenic coupling agent (D), and it has both an anhydride structure (γ) and a hydrolyzable group (〇Rb) in the 八 丄 „ „ , h , knives There are ★ organic hydrazine compounds, and specific examples thereof include compounds represented by the formula (d). (ORb) (d) (Ra)j (Y·)—Si— where Y represents an anhydride structure, or a phenyl group which may have a substituent, and Rb represents an integer number of carbon atoms of 1 to 3 1 to 6 alkyl, 丨 you represent an integer from 1 to 3, j is an integer from 0 to 2, and the number ' i + j + k = 4. can. The base represented by the following formula, etc., is particularly excellent in terms of (9):

(Y1)

0

In the formula, h is an integer representing 〇~1〇. In the formula (d), the alkyl group having a number of 1 to 6 in the range of 1 to 6 in the case of Ra and Rb is the same as the alkyl group having the carbon number of 丨6 to 6 represented by the above R1. The phenyl group which may have a substituent in Table 1 may be the same as the phenyl group which has been exemplified as the substituent shown above. Among them, the compound represented by the formula (d) is preferably a compound represented by the following formula (d-丨):

The armor 'K, h, 1, j, k means the same meaning as above. Y, preferably an alkyl group having 1 to 6 carbon atoms which may have a substituent, such as a methyl group, an ethyl group, a propyl group or a methoxycarbonyl group, and h is preferably 2 to 8. Specific examples of the decane coupling agent represented by the formula (d-Ι) include 2-trisethoxydecylethyl succinic anhydride and 3-triethoxydecylpropyl succinic anhydride. The decane coupling agent (D) having an acid anhydride structure may be used singly or in combination of two or more. In the curable composition of the present invention, the ratio of the content of the above (c) and (M) is (A) to [(B)KC) + (d)] 2 by mass ratio (A) : [( B) + (C) + (D)] = 90 : 10~50 : 50 is better. Further, let the above components (A), (B), (C), and (D) 'B' with (A') and [(B)+(C)+(D)] be (A': [(B) + (C) + (D)] = 90 : 1〇~50 : 50 is better. Furthermore, the ratio of the above (B), (C) and (D) components is [(b) + (c)] To the mass ratio of (D), to [(b) + (c)]: (d) = 9〇: 1〇~1〇: 9〇 is preferred.

28 S 201141952 By using each component in such a ratio, it is possible to obtain a hardening composition which has excellent long-term transparency and heat resistance, and which has a high adhesion even at a high temperature. < Hard The curable composition of the present invention may further contain other components without hindering the object of the present invention. Other components include a curing catalyst, an oxidation inhibitor, an ultraviolet absorber, a light stabilizer, and a diluent. The hardening catalyst is added to promote hardening. The hardening catalyst may be decyl imidazole or triphenylphosphine. These hardening catalysts may be used in combination of two or more kinds of individual cattle. 5 Oxidation inhibitor, The anti-oxidation inhibitor is added to prevent oxidative deterioration during heating. Examples of the anti-oxidation inhibitor include a phosphorus-based oxidation inhibitor, a phenol-based oxidation inhibitor, and a sulfur-based oxidation inhibitor. Examples of the phosphorus-based oxidation inhibitor include triphenyl phosphate. Ester, diphenylisophthalic acid citrate, phenyl diisoindole citrate, tris(壬 & phenyl) vinegar, phosphorus: diisodecyl isopentenyl vinegar, phosphoric acid tris (2, 4-12) Tributyl phenyl) vinegar, cyclooctyl phosphate tetrakis(dione), octyl octanoate, tetrakis(2,4-di-tert-butyl), phosphate ring Octyl pentane bis(2,4-di-tert-butyl-4-methylphenyl) ester, bis[2_t-butyl-6-methyl-(octadecyloxycarboxy)ethyl }Phenyl]hydrogenated discate, 9-dihydro-9-oxa-10-phosphaphenanthracene-oxide, 1〇_(35-di-tert-butyl-4-hydroxyl Benzyl)-9,10_dihydro_9_oxa-1〇__phosphaphenanthrene-oxygen 〇 〇 癸 癸 -9 -9 -9 -9 -9 -9 -9 -9 10 10 10 10 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 2,6_di-tert-butyl-p-nonylphenol, dibutylhydroxymethyl stupid, butylated hydroxyanisole, 2,6-di-t-butyl-p-ethyl-p-ethyl, stearyl-tung Monophenols such as 5-di-tert-butyl+pyridyl-propionic acid; 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2' - anthracenyl bis(4-ethyl-6-tert-butylphenol), 44, _ thiobis(3-mercapto-6-tert-butylphenol), 4,4'-butylene bis ( 3_mercapto- 6_t-butylphenol), 3,9-bis[1,1-diindolyl-2-yl-tert-butyl-4-ylhydroxy-5-methylphenol) propylene oxime Bisphenols such as ethyl}2,4,8, 1〇_tetraoxiro[5,5]dodecane; 1,1,3-tris(2-mercapto- 4-hydroxy-5_ Tert-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxymethylene)benzene, tetra [Asia] Methyl-3-(3',5,1-2 dibutyl-4-4, _ phenyl group) propionic acid vinegar] methane, bis[3,3,-bis(4, _ _ _3, _ Third butylbenzene Butyric acid] glycolic acid, 1,3,5-tris(3,5,2-di-tert-butyl-4, hydroxyl- yl)-S-triazine-2,4,6-(111, 311, 511) a polymeric phenol such as a triketone or a tocopherol. The sulfur-based oxidation preventing agent may be, for example, dilauryl-33, thiodiacetic acid vinegar, or dipyridyl _3,3. - thiodipropionic acid, distearyl-3,3, thiodiacrylate, and the like. These oxidation inhibitors may be used singly or in combination of two or more. However, since the curable composition of the present invention contains (8) component (8) to form a squeegee P, and particularly has an oxidation preventing agent, oxidation deterioration at the time of addition is less likely to occur. For the mass spectrometry "A" or (A) 1 〇〇 mass part, it is usually 〇.. 1 〇 mass part. Ultraviolet absorber, for the purpose of enhancing the obtained hardened material.

S 30 201141952 and added. Examples of the ultraviolet absorber include, for example, stearic acid, stearic acid, p-tert-butylphenyl ester, salicylic acid, p-octyl ester, and the like; 2, 4-hydroxydibenzophenone, 2-hydroxy-4 -Methoxybenzophenone, 2-hydroxy-4-isooctyloxyindolone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2,-dihydroxy-4-yl Oxydibenzophenone, 2,2'-dihydroxy-44,-dimethoxybenzhydryl-'2-hydroxy-4-indolyl-5-sulfonic acid benzophenone, 2-(2, -hydroxy-5,methylphenyl)benzotriazole, 2-(2'-hydroxy-5,-t-butylphenyl)benzotrisene, 2-(2'-trans-yl-3', 5'-di-t-butylphenyl)benzotriazole, 2-(2,-hydroxy-3,_t-butyl-5,-methylphenyl b-5-gas streptotriazole, 2- (2'-hydroxy-3, ,5, _di-t-butylphenyl)_5_gas benzotriazole, 2-(2'-hydroxy-3, 2-{(2'-hydroxy-3', 3,-di-t-amylphenyl) phenyl-β-s, 4', , 5',, 6',-tetrahydro-o-indolediamine fluorenyl)-5'-methylphenyl hydrazine Benzotriazole, bis(2, 2, 6, 6-tetradecyl-4-piperidyl) sebacate, bis (1, 2, 2, 6 , 6, _ 曱 曱 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ A hindered amine such as bis-methylethyl)- 4-p-phenylphenyl fluorenyl butyl malonate or the like. The ultraviolet absorbing agents may be used singly or in combination of two or more. Use Jin, oath + h &w text with s, for the decane compound copolymer (A) or (A,) 100 mass parts 'usually not 〇〇 1〇 quality part. Optical tanning agent, is the promotion of the gallery Adding 0 31 201141952 Light stabilizers can be exemplified by poly[imu-tetramethylbutyl]amino-U'5-tris-H4-diyl }{( 2,2 6 6_tetradecyl _4 dedecyl) imido}hexamethylene {{2 2rr ,,6' 6-tetramethyl-4-piperidinyl)imido}] Hindered amines. These light stabilizers can be used in the form of sg扼.», or in combination of two or more. The amount of the light scorpioning agent used is 1 part by mass for the decane compound copolymer (A) or (A,) 100 parts by mass, usually 0.01 to 10 parts by mass. The diluent is added to adjust the viscosity of the curable composition. The diluent may, for example, be a glycerol diglycidol mystery, a butanediol diglycidyl bond, a diglycidyl dilute & an octapeptide oil basic amine, an octyl glycol glycidyl ether, a cyclohexane diethanol condensate Glycerol ether, alkylene diglycidyl ether, polyglycol glycidyl ether, polypropylene glycol diglycidyl (tetra), trimethoprimin triglycidide shout, glycerol r loser #, 丄-glycidyl ether, 4- Vinyl cyclohexene epoxide, dicyclohexanyl dioxide, methylated dicyclohexyl bromide, and the like. These diluents may be used singly or in combination of two or more. The curable composition of the present invention is obtained by, for example, mixing the above components (A,), (8), (C), and (8), and other components as desired, in a predetermined ratio, and mixing and defoaming by a conventional method. According to the curable composition of the present invention obtained as described above, it is possible to obtain a high transparency even when irradiated with high-energy light or a high-temperature state without coloring or lowering transparency, and has a high degree of adhesion. Hardened material. Therefore, the 'curable composition of the present invention' can be suitably used as a raw material, an adhesive, and a plating material for an optical component, and can be used to solve the problem of high luminance of the optical component. evil

The problem of the S32 201141952, the curable composition of the present invention can be suitably used as a composition for an optical element fixing material. 2) Hardened material According to the second aspect of the present invention, the cured product of the curable composition of the present invention is cured. The method of hardening the curable composition of the present invention is heat hardening. The heating temperature at the time of hardening is usually 1 Torr to 2 Torr, and the heating time is usually 1 Torr to 20 hours, preferably 30 minutes to 1 Torr. The cured product of the present invention has a cured product which is excellent in transparency and has a high adhesion even when it is irradiated with high-energy light or in a high-temperature state without coloring or lowering transparency. Therefore, the cured product of the present invention can be suitably used for an optical component or a molded article, an adhesive layer, a plating layer or the like. In particular, the curable composition of the present invention can be suitably used as a composition for an optical element fixing material in order to solve the problem of deterioration of the optical element fixing material in accordance with the increase in the brightness of the optical element. The cured product of the present invention has a high adhesion, and can be confirmed, for example, by the following force measurement. That is, the mirror-coated curable composition of the Shixi wafer is placed on the object to be pressed by the coated surface, and heat-treated to be cured. Place =' in a preheated to a predetermined temperature (for example, hunger, iG (rc), the tester's measurement ab ^ ^ 疋 ° placed for 30 seconds ' from the height of the body 50 (four), stand up, the opposite side Apply the horizontal square, ^ J &gt; 卞乃凌 (cutting direction) stress, measure the adhesion between the test piece and the object. The adhesion of the hardened material is better than (10)/2_□. 201141952 The above-mentioned cured product is excellent in transparency and can be confirmed by measuring the light transmittance. The light transmittance of the cured product is preferably 8% or more in light of 4 〇〇 nm, and particularly preferably 84% or more. The light having a wavelength of 45 Å is preferably 87% or more. The cured product is excellent in heat resistance, and can be confirmed by placing the cured product at a high temperature and then changing the force or transparency to be small. The transparency is 1 5 〇. I After 500 hours of standing, the transmittance at a wavelength of 4 〇〇 nm is preferably 7% or more of the initial transmittance, more preferably 80% or more. 3) The method of using the curable composition is the third aspect of the present invention, The curable composition of the present invention is used as an adhesive for optical element fixing materials or an optical component fixing material. A method of using an encapsulant. The optical element may be a light-emitting element such as an LED or an LD, a light-receiving element, a composite optical element, or an optical unit circuit. <Binder for optical element fixing material> The curable composition of the present invention can be suitably used as an adhesive for an optical element fixing material. The curable composition of the present invention is used as a method for fixing an optical element, and the composition is applied to one or both of the following materials (such as an optical element and a substrate thereof), and the composition is applied. After that, it is heat-hardened, so that the object of the object $4+ κ is firmly adhered to each other. The main substrate materials of the optical element are: glass of soda glass and heat-resistant hard glass crucible; ceramics of iron, copper, aluminum, gold, silver, platinum, cord, chin, and the like Kim Min Hau A. belongs to the gold, stainless steel (SUS3〇2, S[JS3〇4, SUS304L, SUS309, etc.) and other metals are difficult, and the public is on the formic acid glycol oxime,

S 34 201141952 Polybutylene terephthalate, polyethylene naphthalate, ethylene-ethyl acetate copolymer, polystyrene 'polycarbonate, polymethylpentene, polysulfone, polyether ether A synthetic resin such as a ketone, a polyether sulfone, a polyphenylene sulfide, a polyetherimide, a polyamidamine, a polyamide, an acrylic resin, a norbornene resin, a cycloolefin resin, or a glass epoxy resin. The heating temperature at the time of heat curing is usually 100 to 20 (TC. The heating time is usually from 1 minute to 2 hours, preferably from 30 minutes to 10 hours, depending on the curable composition, etc.) (for optical element fixing materials) Encapsulant) The curable composition of the present invention can be suitably used as an encapsulant for an optical element package. The curable composition of the present invention is used as a method of encapsulating an optical element fixing material, and for example, The composition is molded into a desired shape, and a method of producing a light-emitting element package by heat-hardening the molded body of the optical element is obtained. The hardenability of the present invention is Α, jj / /Note, 'and The method of forming the mouth shape into a desired shape is not particularly limited, and a conventional molding method such as a & Ρ 锊 锊 molding method or an injection molding method can be employed. The tear is added during heat hardening; $:, g The preparation/dishness, although depending on the hardening composition used, is usually 100~200°C. Add time to the hall or 1n, ... 矸 逋 为 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 The light το package is used due to the use According to the curable group of the invention, even in the case where the light element 'using a white or blue light-emitting wavelength of a short wavelength of ·49 〇nm' is not colored by heat or light, it is transparent and heat-resistant. [Examples] Next, the present invention will be described in more detail by way of examples and comparative examples, but the present invention is not limited by the following examples. (Measurement of weight average molecular weight) The decane compound copolymer obtained in the production example The weight average molecular weight (Mw) is measured in terms of standard polystyrene and is measured by the following apparatus and conditions. Device name: HLC-8220GPC T0S0 company

Column: TSKgelGMHXL, TSKgelGMHXL and TSKgel 2000HXL are connected in sequence. Solvent: tetrahydrofuran injection amount: 80# 1 measurement temperature: 40 ° C flow rate: 1 m 1 /min. Sense stolen. Inhomogeneous refractometer (measurement of IR spectrum) IR spectrum of the decane compound copolymer obtained in the production example Determined by the following apparatus. FT-IR-infrared spectrometer (Spectrum lOO, manufactured by Perkin Elmer) (manufacturing example 1) In a 300 ml water-dropping flask, phenyl trimethoxy zeshi (manufactured by Tokyo Chemical Industry Co., Ltd.) 16.7 g (84 mmol) was used as decane. Compound (2), 3-ethyloxypropyltrimethoxy decane (manufactured by Oct. 21 Co., Ltd.) 8_〇 layer (36111111〇1) as Shi Xi

S 36 201141952 . Alkane compound (D, as a solvent, put it into 6 〇ml, steamed water 30 ηη1, and then add the acid (manufactured by Kanto Chemical Co., Ltd.) 〇15g (i5mm〇1) as a catalyst. After further stirring for 16 hours at room temperature, after the reaction was completed, 1 〇〇 ml of ethyl acetate was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution. After standing for a while, the organic layer was separated. Then, the organic layer was distilled water. After washing twice, it was dried over anhydrous magnesium sulfate. After filtering magnesium sulfate, the filtrate was concentrated to 5 〇ml with a vacuum concentrator, and this was added dropwise to a large amount of n-hexane to reprecipitate the precipitate by decantation. The sulphate compound copolymer (A1) 14. 7g is obtained by dissolving the obtained sulphate in a methyl ketone. The decane compound copolymer (A1) is obtained by vacuum drying to obtain a decane compound copolymer (A1). The weight average molecular weight (Mw) was 2,700, and the molecular weight distribution was (Mw/Μη) of 1.53. Further, the IR spectrum (Fourier transform infrared spectroscopy (FT-1R)) of the broth compound copolymer (Α1) was expressed as follows. • Si-Ph: 699CHT1 741 cm -, Si-0: 1132 cm.1, -CO: 1738 cm.1 (Production Example 2) In Production Example 1, the amount of phenyltrimethoxy decane used was U 3g (72 〇 1) ' 3- In the same manner as in Production Example 1, the oxime compound copolymer (A2) was obtained in an amount of 15.9 g. The weight average molecular weight of the stilbene compound copolymer (A2) was 5%. (mw) is 2,600, and the molecular weight distribution (Mw/Mn) is 1.50. Further, the IR spectrum of the decane compound copolymer (A2) (Fourier to 37 201141952 by infrared spectroscopy (FT-IR)) data is expressed as follows .

Si-Ph: 699 cm 丨' 741 cm 丨, Si-〇: (1) (4)-1, -CO: 1738 cm-1 (Production Example 3) In Production Example 1, the amount of phenyltrimethoxydecane used was 19. 9 g。 The decane compound copolymer (A3) 14.9 g was obtained in the same manner as in Production Example 1, except that the decane compound copolymer (A3) was obtained. The decane compound copolymer (A3) had a weight average molecular weight (Mw) of 2,500 and a molecular weight distribution (Mw/Mn) of 1.59. Further, the IR spectrum (Fourier transform infrared spectroscopy (F T -1R)) data of the decane compound copolymer (A3) is shown below.

Si-Ph: 70Ocm-1' 742CHT1, Si-〇: 1132cm-1, -CO: 1738cm-1 (Production Example 4) In Production Example 1, the amount of phenyltrimethoxydecane used was 167g (84ππηο1). 'Substituting 3_Ethyloxypropyltrimethoxyacetate 8 〇g (3 6mmo 1), using phenyltrimethoxy decane (manufactured by Tokyo Chemical Industry Co., Ltd.) 11_9g (60mmol) and 3-glycerol The acid propyl trimethoxy oxime (manufactured by Tokyo Chemical Industry Co., Ltd.) (hereinafter referred to as "GlyTMS" in Table 1 - 1 and Table 1 - 2 below), 14.2 (60 mmol), and the production example 1克。 The decane compound copolymer (A4) 16.3g. The decane compound copolymer (A4) had a weight average molecular weight (Mw) of 2,800 and a molecular weight distribution (Mw/Mn) of 1.56. Further, the IR spectrum (Fourier transform infrared spectroscopy (FT-IR)) data of the decane compound copolymer (A4) is shown below.

38 S 201141952

Si-Ph : 700cm-1 ' 742cm.1 ' Si_〇: 1132cnfl, epoxy group: 1254cm -1 (Production Example 5) In a 300ml water drop bottle, put in a stupid base of tridecyloxy decane (Tokyo Chemical Industry Co., Ltd.) 19. g (96 mmol) as a decane compound (2), 3-chloropropyldimethoxy zebra (manufactured by Tosho, Kasei Kogyo Co., Ltd.) 4.77 g (24 minol) as a calcined compound (1) as a solvent After adding 30 ml of toluene, 6 〇 111, and distilled water, the mixture was stirred, and 15 g (1.5 mmol) of acid (manufactured by Kanto Chemical Co., Ltd.) was added as a catalyst, and further stirred at room temperature for 16 hours. After the end of the reaction, ethyl acetate 1 〇〇m 1 was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution. After standing for a while, the organic layer was taken. Then, the organic layer was washed twice with steaming water, and then dried with anhydrous sulfuric acid. After passing through the sulfuric acid town, the filtrate was dropped into a large amount of normal calcined water to be reprecipitated, and the hexane was removed to remove the precipitate. 6克。 The decane compound copolymer (A5) 13. 6g. The decane compound copolymer (A5) was obtained. The weight average molecular weight (Mw) of the calcined compound copolymer (A 5 ) is 3,000 Å and the molecular weight distribution is (Mw/Mn) of 1.59. Further, the IR spectrum data of the decane compound copolymer (A5) is shown below.

Si-Ph '·700cm&quot;1 » 741cm'1 » Si-0 : 1132cm'1 5 -Cl '· 648cm'1 (Production Example 6) In Production Example 5, the amount of phenyltrimethoxydecane used was 16 7 g (84 mmol), the amount of 3-cyclopropyltrimethoxy decane used was 7.15 g 39 201141952 (36 mmol). In the same manner as in Production Example 5, 13.4 g of a decane compound copolymer (A6) was obtained. The decane compound copolymer (A6) has a weight average molecular weight (Mw) of 3,300 and a molecular weight distribution (Mw/Mn) of 1.59. Further, the IR spectrum data of the decane compound copolymer (A6) is expressed as follows.

Si-Ph: 70 0cm'1 &gt; 742cm'1 &gt; Si-〇: 1133cm'1 &gt; -Cl : 648cm'1 (Production Example 7) The use amount of phenyltrimethoxydecane in Production Example 5 In the same manner as in Production Example 5, 13.0 g of a decane compound copolymer (A7) was obtained, except that the amount of the solvent was 1. </ RTI> ( </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> The decane compound copolymer (A7) had a weight average molecular weight (Mw) of 3,400 and a molecular weight distribution (Mw/Mn) of 1.61. Further, the IR spectrum data of the decane compound copolymer (A7) is shown below.

Si-Ph: 699 cm1, 741 cnf1 'Si-〇: 1132011-1, -Cl: 648 cm-1 (Production Example 8) The amount of phenyltrimethoxy decane used in the production example 5' was n9 g (60 〇 1) The decane compound copolymer (A8) was obtained in the same manner as in Production Example 5 except that the amount of the 3-methoxypropyltrimethoxydecane used was n.9 g (60 mmol). The weight-average molecular weight (Mw) of the Shiqi-sinter compound copolymer (A8) was 3,600, and the molecular weight distribution (Mw/Mn) was 1.63.

40 S 201141952 Further, the IR spectrum data of the decane compound copolymer (A8) is expressed as follows.

Si-Ph: 700 cm'1 &gt; 741 cm-1 &gt; Si-O: 1133 cm'1 &gt; -Cl: 648 cm'1 (Production Example 9) In Production Example 5, 3-cyclopropyltrimethoxydecane 4 was replaced. 77 g of a decane compound copolymer (A9) was obtained in the same manner as in Production Example 5 except that the product was obtained by the method. The weight average molecular weight (Mw) of the zephyr compound copolymer (A9) was 2,900' molecular weight distribution (Mw/Mn) of 1.58. Further, the IR spectrum data of the decane compound copolymer (A9) is shown below.

Si-Ph: 70 0cm ^ 741cm'1» Si-O: 1131cm'1 &gt; -CN : 2252cm'1 (Production Example 10) In Production Example 9, the amount of phenyltrimethoxydecane used was 16. In the same manner as in Production Example 9, except that 7 g (84 mmol) and 2-cyanoethyltrimethoxy decane were used in an amount of 6.31 g (3 6 mmo 1 ), 13 g of a compound (A10) was obtained in the same manner as in Production Example 9. The decane compound copolymer (A10) had a weight average molecular weight (Mw) of 3,200 and a molecular weight distribution (Mw/Mn) of 1.64. Further, the IR spectrum data of the decane compound copolymer (A10) is shown below.

Si-Ph: 699 cm -1,742 (:111_1, Si-〇: 1131 cm ' -CN: 2253 cm.1 (Production Example 11) 41 201141952 In Production Example 9, the use of phenyltrimethoxy decane was used. 14.3 g (7 2 mmol ) and 2-cyanoethyltrimethoxy oxime were used in the same manner as in Production Example 9 except that the amount of 2-cyanoethyltrimethoxy oxime was &amp; (48 mmo 1 ). g. The amount (Mw) is the weight average molecular weight of the copolymer of the smelting compound (All) 3, 300, and the molecular weight distribution (Mw/Mn) is 1.62. Further, the ir spectrum data of the decane compound copolymer (All) The table is as follows.

Si-Ph: 6 99cm·1» 742cm'1» Si-〇: 1131cm'1« -CN: 2253cm-1 (Production Example 12) In Production Example 9, the amount of phenyltrimethoxydecane used was U9g. (2.3 mmol) of the decane compound copolymer (A12) was obtained in the same manner as in Production Example 9 except that the amount of (2,0,5,0,0,0,0,0,0,0,0,0,0,0,0,0,2,2,3,3,3,3,3,3,3,3,3,3,3,2 The weight average molecular weight (Mw) of the Shiqi-sinter compound copolymer (A12) was 3,500', and the molecular weight distribution (Mw/Mn) was 1.61. Further, the Ir spectrum data of the decane compound copolymer (A12) is shown below.

Si-Ph: 70 0cm'1 &gt;742cm&quot;1&gt; Si-〇: ll33cm-', _cn: 2252cm'1 (Example 1) The decane compound copolymer (A1) obtained in Production Example 1 was 1 〇g, 1. 5 g of an epoxy compound having an isocyanurate skeleton (manufactured by Nissan Chemical Industries, Ltd., TEPIC-PAS B26, epoxy equivalent: 137 g/eq) (in the following paragraph: i Table-1, Table 1) It is described as "B1".) As an epoxy compound (β), 375. 375g 42 s 201141952 ' 4-methylcyclohexane-1,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) Table-1 and Table 1 are described as "C1".) and Cyclohexa-1,2,4-tricarboxylic acid-1,2-anhydride (manufactured by Mitsubishi Gas Chemical Co., Ltd.) (Table 1 below) -1, the first table 2 is described as "C2".) As the curing agent (c), and 0.375 g of 3-diethoxy schyl propyl sulphate (according to AZMAX) (below 1) and 1st table 2 are described as "D1".) As a decane coupling agent (D), the entire volume is sufficiently mixed and defoamed to obtain a curable composition (Examples 2 to 7). Table 1, Table 1, using a decane compound copolymer, an epoxy compound In the same manner as in Example 1, the curable compositions (2) to (7) were obtained in the same manner as in Example 1. Further, in the following Tables 1 and 1, Table 2, "B2" was used. An epoxy compound having an isocyanurate skeleton (TEPIC-PAS B22, epoxy equivalent i79 g/eq, manufactured by Nissan Chemical Industries, Ltd.) is shown. (Comparative Examples 1 and 2) The use of decane according to the following Table 1 - 丨 ' The compound copolymer 'epoxy compound, hardener, and decane coupling agent were obtained in the same manner as in Example , to obtain curable compositions (8) and (9). (Comparative Example 3) Example 1' Substituted epoxy As the compound (B), 3,4-epoxycyclohexylmethyl 3,4 epoxycyclohexylcarboxylate (manufactured by Sikma Aldrich Co., Ltd.) was used (see Table 1 below, Table 1 below) In the same manner as in Example 1, a curable composition (1〇) was obtained in the same manner as in Example 1. (Comparative Example 4) 43 201141952 In Example 1, the decane compound obtained in the production example was replaced. Copolymer (A1) 'The curable composition (丨丨) was obtained in the same manner as in Example 1 except that the decane compound copolymer (A4) obtained in Production Example 4 was used. (Comparative Example 5) In the example 1 'substituted decane coupling agent (D1), 3-glycerol propyl dimethoxy zeshi (manufactured by Tosei Kasei Co., Ltd.) was used (in Table 1 below, In the first table 2, § has been carried out as "DF1".) A curable composition (12) was obtained in the same manner as in Example 1 except for 375 g. (Comparative Example 6) 0.375 g of tetradecyl oleate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the oxime coupling agent (D1) of Example 1 (described in Table 1 below, Table 1 below) In the same manner as in Example 1, except for "DF2".), a curable composition (13) was obtained. (Example 8) 10 g of the decane compound copolymer (A5) obtained in Production Example 5, and 1.5 g of an epoxy compound having an isocyanurate skeleton (manufactured by Nissan Chemical Industries, Ltd., TEPIC-PAS B26 'epoxy equivalent) !37g/eci) as a decane coupling agent (B), 0. 38 g of 4-methylcyclohexane-1,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 0·75 g of cyclohexane_1, 2, 4-tricarboxylic acid_1,2-anhydride (manufactured by Mitsubishi Gas Chemical Co., Ltd.) as a curing agent (C), and 38.38 g of 3-triethoxydecyl propyl sulphate anhydride (manufactured by AZMAX Co., Ltd.) as a decane couple In the mixture (D), the whole container is thoroughly mixed and 'defoamed' to obtain a curable composition (14). (Examples 9 to 15 and Comparative Examples 7 to 16) In the same manner as in the following Table 2-2', using a decane compound copolymer and epoxidation 44 201141952 Example 8, a compound, a curing agent, and an oxime The coupling agent is used to carry out the curable composition (15) ~ (31). 45 201141952 Table 1-1 decane compound copolymer epoxy compound (mass part) Hardener (mass fi part) 矽 耦合 coupling agent (mass part) A: [(B)+ (C)+(D)] (mass ratio Hardenability composition ratio (mole) Composition type decane compound decane compound decane compound decane compound GlyTMS (mass part) B1 B2 BF1 C1 C2 D1 DF1 DF2 (la) (lb) (lc) (2) Example 1 A1 30 - - 70 - 10 1.5 - - 0.375 0.75 0.375 - - 77:23 Example 2 2 A1 30 - - 70 - 10 - 1.5 - 0.375 0.75 0.375 - - 77:23 Example 3 3 A1 30 - - 70 - 10 1.5 - - - 0. 75 0.75 - - 77:23 Example 4 4 Λ 2 40 - - 60 - 10 1.5 - - - 0.75 0.75 - - 77:23 Example 5 5 A3 20 - - 80 - ]〇1.5 - - - 0.75 0.75 - - 77:23 Example 6 6 Λ1 30 - - 70 - 10 1.0 - - 0.25 0.5 0.25 - - 83:17 Example 7 7 A1 30 - - 70 - 10 2.0 - - 0.5 1.0 0.5 - - 71: 29 Comparative Example 1 8 A1 30 - - 70 - 10 1.5 - - 0.75 0.75 - - - - Comparative Example 2 9 A1 30 - - 70 - 10 1.5 - - 0.75 - 0.75 - - - Comparative Example 3 10 A1 30 - - 70 - 10 - - 1.5 0.375 0.75 0.375 - - - Comparative Example 4 11 A4 - - - 50 50 ]〇1.5 - - 0.375 0.75 0.375 - - - Comparative Example 5 12 A1 30 - - 70 - 10 1.5 - - 0.375 0. 75 - 0.375 - - Comparative Example 6 13 A1 30 - - 70 - 10 1.5 - - 0.375 0.75 - - 0.375 - decane compound (la) : 3-ethylmercaptopropyltrimethoxydecane decane compound (lb) : 3-cyclopropyltrimethoxydecane decane compound (lc) : 2-mercapto Isomethoxytrimethoxydecane compound (2): Phenyltrimethoxydecane, Table 1-2, decane compound copolymer, ring gas compound (ft part), hard ^ (quality 1 匕 i i矽 耦合 耦合 coupling agent (mass t part) A: [(B) + (C) + (D)] (mass ratio) Hardenability composition ratio (Mole 50 composition type decane compound decane compound decane compound decane compound GlyTMS ( Quality Department) B1 B2 BF1 C1 C2 D1 DF1 DF2 (la) (lb) (lc) (2) Example 8 14 A5 - 20 - 80 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 9 15 A6 - 30 - 70 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 10 16 Λ7 - 40 - 60 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 11 17 Λ8 - 50 - 50 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 12 18 A9 - - 20 80 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 13 19 A10 - - 30 70 - 10 1.5 - 0.38 0.75 0.38 - - 77:23 Example 14 20 Λ11 - - 40 60 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Example 15 21 Λ12 - - 50 50 - 10 1.5 - - 0.38 0.75 0.38 - - 77:23 Comparative Example 7 22 A6 - 30 - 70 - 10 1.5 - - 0.75 0.75 - - - - Comparative Example 8 23 A6 - 30 - 70 - 10 1.5 - - 0.75 - 0.75 - - - Comparative Example 9 24 A6 - 30 - 70 - 10 - - 1.5 0.375 0.75 0.375 - - - Comparative Example 10 25 A6 - 30 - 70 - 10 1.5 - - 0.375 0.75 - 0.38 - - Comparative Example 11 26 A6 - 30 - 70 - 10 1.5 - - 0.375 0.75 - - 0.38 - Comparative Example 12 27 A10 - - 30 70 - 10 1.5 - - 0.75 0.75 - - - - Comparative Example 13 28 A10 - - 30 70 - 10 1.5 - - 0.75 - 0.75 - - - Comparative Example 14 29 A10 - - 30 70 - 10 - - 1.5 0.375 0.75 0.375 - - - Comparative Example 15 30 A10 - - 30 70 - 10 1.5 - - 0.375 0.75 - 0.38 - - Comparative Example 16 31 A10 - - 30 70 - 10 1.5 - - 0.375 0.75 - - 0.38 - decane compound (la) : 3-ethoxypropyl propyl trimethoxide Alkane decane compound (lb): 3-cyclopropyltrimethoxydecane decane compound (lc): 2-cyanopyranosyl decane decane compound (2): Stupyl trimethoxy decane About Example 1~ 1 5 and the curable composition obtained in Comparative Examples 1 to 16

S 201141952 Hardened material of 1 to 31', as described below, the transmittance after heating. The measurement results are shown in the following (continuous force test), and the adhesion, initial penetration, and Table 2 and Table 2-2 were measured. For the mirror surface of the 2mm square gang H,, the Shi Xi BB piece, apply the hardening composition &quot; to make each coated thickness of about 2 &quot; m ' put the coated surface on the object (silver-plated copper plate) Crimp. After that, the cockroach was sterilized for 2 hours to harden it to obtain the object with the test piece. The object to which the test piece is attached is placed on a measuring stand preheated to a predetermined temperature (example #饥,1〇.. 接着 接着 测试 Series (Series 4000 'DAGE)) for 3 sec. The position of the height of the body 50" is measured by the speed 2〇〇&quot;m/s, and the stress of the flattening method (cutting direction) is measured at 23t and 10 (the test piece and the object of the TC) The force is N/2mm. (Continue to heat resistance) "In the case of the adhesion test, the adhesion force at the loot is evaluated as "〇" when it is 50% or more of the contact force of 23t, and when it is less than 5〇% "X". (Measurement of initial penetration rate) The curable compositions 1 to 31 were poured into a mold to grow 25 mm, width 2 〇, and thickness lmm 'heated at 40 ° C for 6 hours to harden.乍 验 验 验 验 验 验 验 验 验 验 验 验 验 验 验 验 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 初期 4 4 4 4 4 4 Rate measurement 'The penetration rate of 4〇〇nm is 8〇% or more and is estimated to be 47 201141952 〇”. The above 80% is “△”, less than 70%. χ 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定 测定). This is taken as the penetration rate after heating. [Heat resistance (transparency after heating)]

S is the transmittance after heating, and the transmittance at 4 〇〇 nm is estimated to be “〇” for 80% or more of the initial transmittance, and less than 8 ()% for 7〇 or more is “△”, less than 70 % is "X". Table 2-1 Curable composition (f follows force Ί/2πιπ〇) Initial edge ratio (%) Initial transparency, heat transmission, heat resistance (transparency after heating) 23°C, 100°C, heat resistance 400nm 86 2 450nm QQ A - 400nm ) 450nm Example 1 1 152.6 95.5 CT Example 2 2 134.4 82.6 〇88.6 0〇. 4 89.5 Ο 〇~ 83.0 — 〇〇t\ 87.2 〇! Example 3 3 156.1 107.3 〇85.9 87.7 〇〇c. 9 〇〇1 87.1 〇Example 4 4 141.3 86.0 〇[89^ 90.6 〇Γ7 i 〇〇ώ. 1 ~82ΤΓ 87. 〇〇Example 5 5 162.2 101.1 〇84 o 87.3 〇Example 6 _Example t 6 7 138.0 177.5 80.1 114.2 〇ο 87.5 86 3 o7.1 89.3 Q7 o ό 〇 82.3 in-1 86.9 87.6 〇〇Comparative Example 1 Comparative Example 2 8 9 158.6 90.2 93.7 40.8 〇X 60.1 87.9 0 i. o 71.3 89.4 ~8ΪΓ ~9〇1~ ~76ΓΓ ϋ X 〇~ο~~ &quot;~ο~~ X 82.2 58.3 87.1 70.3 〇〇Comparative Example 3 10 169.1 92.4 〇83.T 81.9 -- - 52.7 87.5 〇 Comparative Example 4 11 170.7 112.9 〇88ΤΓ B7.8 ~6Q?T~ 65. 4 X ΙΣΙ Λ Comparative Example 5 Comparison 丨fi 12 1Q 142.3 140 5 89.4 Q7 ^ 〇r\ 6 9. Γ 1 0 O I . 0 65. 7 Γ 73.6 X 64.4 72.9 L〇~ 48 201141952 Table 2-2

The cured product of the cured materials (1 to 7, 14 to 21) of the second table-1 and the second table-2's 1 to 15 is that 23〇c has a high adhesion force of 134N/2 mm□ or more. The temperature (loot) also remains at 23. The adhesion force of 58% or more of the adhesion force is excellent in heat resistance. In addition, the initial transmittance at a wavelength of 4 〇〇 nm and 45 〇 nm and the transmittance after heating are high, and the initial transparency and heat resistance are high. The properties (transparency after heating) are excellent. On the other hand, the cured physical compositions of Comparative Examples 1, 5 to 7, 10 to 12' 15, 16 (8, 12, 13, 22, 25 to 27, 30, 31) The cured product was inferior in heat resistance. The cured products of the curable compositions (9, 23, and 28) of Comparative Examples 2, 8, and 13 were inferior in both the contact force and the heat resistance, and Comparative Examples 3 and 4. The hardened composition of the hardening composition (9, 14, 24, 29) of 9,14, heat resistance 49 201141952 (transparency after heating) is significantly inferior. [Simple description of the figure] None. [Main component symbol description 】 No.

50 S

Claims (1)

201141952 VII. Scope of application: 1 · A kind of hardening composition, comprising: (A) a copolymer of oxalate, in the numerator and (ii), having the following formulas (i), (ii) and (1) Among the repetitive units of the heart, (1) and (Η), (11) and 0^) or (1), (11) and 〇1〇111 ..., &lt;reverse early 'weight average molecules篁 is 1,000 to 30, 000; (8) epoxy compound having an isocyanate-based ester skeleton; (C) hardener 'containing an anhydride having a carboxyl group; and anhydride and other alicyclic acid (D) decane coupling agent With anhydride structure. R\ . pH-χ° (iii) wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and X represents a dentate atom, a cyano group or a group represented by the formula: 〇G, wherein the G system represents The protecting group of the hydroxyl group 'D means a single bond or a linking group, and R2 means a phenyl group of a carbon number or a phenyl group which may have a substituent. 2. The sclerosing combination as described in claim 1 And the decane compound copolymer of the above (A) is represented by the formula: V-CHCD-D- 51 201141952 &lt;the amount of ([R2]) molar ratio 5 · 9.5 of the stone compound compound copolymer The amount of existence ([RLCIKXy-D]) and R2 is, [R'-CHU.)-D]: [R2] = 60: 40~. The content ratio of the hardenable composition is as follows: (A) [(B) + (C) + (D)] = 90: 3. As in the scope of claim 1 or 2, the above (A), The mass ratio of (B), (C), and (D) components to [(3) + (〇+ 〇)], with (^): 10 〜 5 0 : 5 0. 4. A hardenable composition comprising: (A') a crushed alkyl compound copolymer, which is comprised of formula (i): r1_ch (X°)-D-Si(OR3)p(Xi)3_p And a mixture of at least one of the decane compound (1) and a mixture of the decane compounds of at least one of the decane compound (2) represented by R2Si(〇R4)q(X2)h, wherein the weight average molecular weight is 1, 〇〇〇~30, 〇〇〇; (B) an epoxy compound having an isocyanurate-based skeleton; (c) a modifier comprising an alicyclic sorghum having a slow base and the like An alicyclic acid anhydride; and a ceremonial coupling agent having an acid anhydride structure: wherein R represents a hydrogen atom or an alkyl group of carbon number 6, hydrazine. The system represents a dentate atom, a cyano group or a group of the formula: QG (d), wherein the G system represents the protection of the radical group "'D represents a single bond or a linker, and the r3 system represents a burnt group of carbon number 6'" The system represents an atomic atom, and the P system is an integer of Η; R2 represents an alkyl group having a carbon number of 20 or a phenyl group which may have a substituent, and R4 represents a carbon number of the alkyl group. Indicates an integer from 0 to 3. 5. The sclerosing composition according to claim 4, wherein the compound of the above-mentioned (A) is a compound of the compound of the compound (1) and the compound of the compound (2) Ratio, [decane compound (1)]: [decane compound (2)] = 60: 40~5: 95 ratio of condensation. 6. The curable composition according to claim 4, wherein the ratio of the components (A,), (B), (c), and (D) is (A,) and [ (B) + (C) + (D)] mass ratio to (A, ): [(B) + (C) + (D)] = 90 : 1〇~50 : 50 . 7. The curable composition according to claim 1 or 4, wherein the content ratio of the above components (c), (D) and (D) is [(B) + (c)] and (D) Mass ratio 'with [(B) + (C)] : (D) = 90 : HM0 : 90. The curable composition according to claim 1 or 4, wherein the hardened material of the above (C) is selected from the group consisting of one or more selected from the group consisting of an alicyclic acid anhydride having a carboxyl group and another known cyclic acid anhydride. , the mass ratio is (having a few groups of alicyclic anhydride): (other alicyclic anhydride) = 1 〇〇: 〇 ~ 1 〇: 9 〇. The curable composition according to claim 1 or 4, which is a composition for an optical element fixing material. 1 0. A cured product obtained by hardening a hardenable composition as described in claim i or 4 of the patent application. 11. A cured material as claimed in claim 1G, which is an optical component fixing material. 12. A method of using the hardening composition according to claim 4 or 4 as an adhesive for an optical element fixing material. 13. A method of using the hard 53 201141952 chemical composition described in claim 1 or 4 as an encapsulant for an optical element fixing material. 54 S 201141952 IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. The chemical formula of the levy: 5. If there is a chemical formula in this case, please reveal the best indication of the invention. VI. Description of the invention: [Technical field of the invention] The present invention relates to transparency and heat resistance which can be obtained. Further, a curable composition having a cured product having a high contact force, a composition obtained by curing the composition into a petrochemical material, and a method of using the above composition as an adhesive for an optical element or a mouth material or a package for fixing an optical element. [Prior Art] The conventional 'curable composition' has been variously modified according to the use, and is widely used in the industry as a raw material for an optical component or a prototype, a coating agent, and the like. For example, 'the formation of a cured product excellent in transparency; a composition as a raw material of an optical component, or a coating agent thereof, and a curable composition which forms a cured product having a high adhesion, which is good (d) as an adhesive or Coating agent. In addition, the 'curable composition of the present invention' is a composition for an optical element fixing material such as an adhesive for an optical element fixing material or an encapsulating agent for an optical element cage.