TW201020279A - Siloxane, hardening resin composition, hardened substance thereof, and optical semiconductor component - Google Patents

Abstract

The present invention relates to a novel reactive functional groupcontaining a siloxane (A), a hardening resin composition including the siloxane (A) and a hardening agent (B), and an optical semiconductor component (such as LED) hermetically sealed by a hardened substance thereof, wherein the hermetically sealed optical semiconductor component demonstrates excellent resistance to light and low elasticity at low temperature. The siloxane (A) is a block-type siloxane oligomer having a chain of silicone segment and a hydrolysis and condensation segment of trialkoxysilane (C1-C10) containing a group selected from the group consisting of epoxy-containing reactive functional group, methyl, and ethyl, wherein at least a portion of the hydrolysis and condensation segment contains at least an epoxy-containing reactive functional group. The siloxane is obtained by the first step reaction and the ensuing second step reaction described hereunder. 1st step reaction: Reacting the siloxane compound in the condition that the alkoxy equivalent is within 1.5 to 200, relative to one equivant of silanol group of silanol ending polysilicone oil; 2nd step reaction: In the presence of water, subject the said alkoxysilane and the alkoxy group of the product obtained from 1st step reaction, to undergo hydrolysis and condensation reaction.

Description

201020279 VI. Description of the Invention · [Fa:: Field of Sweeping] The manufacturing method 2 is a composition of a novel oxy-oxygen compound containing a reactive functional group, a photonic property, and a low-k composition. More specifically, the fiscal transparency and the fat composition are excellent; and the low-elasticity 11 is excellent in the use of a curable tree for optical semiconductors. [Prior Art] An optical semiconductor element sealed by the cured product. (4) Materials which can be used for optical semiconductor elements such as economical flat paper LEDs, and epoxy resins are used for the purpose of heat resistance and transparency. In particular, the two-year-old A-type ring, which is excellent in balance between oxygen tree (4) and riding ring = ^, has recently been developed, and the disk t τ 曰· and the illuminating intensity ED are short-wavelength (10) rnn to 480 nm. As a result, it is pointed out that due to the influence of light, the color is lowered and the characteristics of the LED are finally lowered. The mechanical properties of the fat f are carried out for the purpose of coloring the sealing material by collecting the light of the tree. However, compared to the epoxy resin, the polysulfate tree is sealed. Therefore, the problem of poor ancientity is such that only the dense deformation of the gel state can be selected. ® indicates that the surface is sticky or has a durability of the Si (II), especially in the upper oxygen compound. 'In the organic solvent, the organic test 1 million heating, the weight average molecular weight is _ to W machine money to burn. From the point of view of Nike, there are 321483 4 201020279 burning higher than the previous epoxy resin. And 'relative to the bifunctional burning Oxygen stone compound compound improves the tackiness and hardness by increasing the amount of introduction of the trifunctional burnt oxygen stone compound. However, in order to improve the surface hair and the deformation, the hardness of the hardened material is increased. In particular, the modulus of elasticity in the low temperature range (1) is less than that. As a result, in the thermal cycle test, the low modulus (lower than -30 ° C) low in elastic modulus is inferior. The sealant cured product is at a low temperature. The low modulus is one of the important characteristics in the optical semiconductor encapsulant, and this improvement has become an important issue. [Prior Art Document] [Patent Document] [Patent Document 1] Japanese Re-Patent Patent W02005/100445 [Problem to be Solved by the Invention] An object of the present invention is to provide a siloxane compound, a curable resin composition using the compound, and an optical semiconductor element using the curable resin composition as a Φ sealing material. In the present invention, the present inventors have solved the above problems as a novel compound having a reactive functional group which is an LED sealing material and has a light-resistant property and a low modulus of elasticity at a low temperature. While focusing on the research, I found out that it consists of a polyether having a sterol end group represented by the following formula (2); an oxime oxygen oil (Shi Xi compound) and a reactive functional group containing an epoxy group. A compound having a chain polyfluorene chain segment and a hydrolyzed condensed segment of a 3 5 321483 201020279 alkoxydecane obtained by reacting a trialkoxylate compound (Australian compound) can be used to solve the above-mentioned lesson: 3 Reactive functional group of the sulphur-oxygenated sputum. That is, the curable resin group containing the oxyalkylene group has a silky line satisfying the above (four) rest; The invention is completed by the result. 1 double mouth and, as the above is known, the ^ ^ ^ - A * ^ ^ - invention of the oxane compound is from the chain 敝 and the money An oligomer (polymer) formed by cutting a condensation segment (preferably a sesquiterpene 1%, a 1.110 bond segment), and the hydrolysis condensation segment contains at least one epoxy group. That is, the present invention relates to the following: ❹ ^: an 11-oxygen-containing compound containing a *reactive functional group having a chain-like polycene segment and having an epoxy group-containing group a reactive functional group, a group of three groups (C1__基基钱), and at least a part of the group contains at least one hydroxyl group reaction Chain of a functional functional group = [2] The phenanthroline chain segment containing a reactive functional group as described in the above (1), /, a hydrolyzed condensed segment. [3] The oxygen-containing compound containing a reactive functional group as described in the above (1) or (2), which is obtained by the following two-stage reaction, wherein the first-stage reaction is carried out by the alcohol (9) of the formula (2) The oil (b) and the pyrolysis gas shown in the general formula (1), the compound (a) 'at the end of the phase material, the money (6) is said to be the base 1 when the 1 'burning oxygen compound is burned to the amount of oxygen #15 to 2 (10) equivalents of 321483 6 201020279 range of reaction and condensation, followed by the second stage of the reaction is water & in the resulting reaction solution, the remaining alkoxy hydrolysis / condensation; / I3 \ HO-| - Si —0 十-H (2) \ R3 / m (In the formula, there are a plurality of R3s which may be mutually the same or different, representing the carbon number to the direct bond of the king 10, branch or ring, and carbon The number of aryl groups of 6 to 14 is 2 to 10 alkenyl groups; m represents an average value of 2 to 2000) ❹ XSi(〇R2)3 (1) (wherein X represents a reactive functional group having an epoxy group;匕 represents an alkyl group having 1 to 10 carbon atoms). [4] The oxo-oxygen-containing compound containing a reactive functional group as described in the above [3], wherein m is from 2 to 200. * [5] The reactive functional group-containing oxoxane compound as described in the above [丨], wherein the first-stage reaction system is represented by the formula (2); (b), both with the alkoxydecane compound (a) represented by the formula (1) and the oxygenated my compound (c) of the formula (3), in the opposite phase of the aspartic acid 『 = alcohol base i equivalent, the oxygenated Wei compound (4) and the alkoxy group of (c) are always reacted and condensed in the range of 1.5 to 200 equivalents, and then the second stage reaction is carried out by adding water to the obtained In the reaction solution, the remaining methoxy group is hydrolyzed and condensed;

321483 7 201020279 (In the formula, there are a plurality of enthalpy or mutual $, which means a linear, branched or cyclic alkyl group with a carbon number of ^ι〇, an aryl group or a carbon number of 6 carbon 4 2 to 10 alkenyl; m represents an average of 2 to 2 (10)) XSi(〇R2)3 (1) (wherein 'X represents a reactive functional group having an epoxy group; & represents a carbon number i to 10 alkyl group R4Si(〇R2)3 (3) (wherein 'I represents a methyl group or a phenyl group; and R2 may be the same as or different from the & of the formula (1), and each independently, representing a carbon number! to a hospital base of 10). [6] The reactive functional group-containing shixiwei compound as described in any one of the above [3] to [5] wherein the formula (2) is independently and represents a methyl group or a phenyl group; (1) Each of them is independently a methyl group or an ethyl group; and R2 of the formula (3) may be the same as or different from R2 of the formula (1), and independently, represents a methyl group or an ethyl group. m. The oxycyanyl compound containing a reactive functional group as described in any one of the above [3] to [6] wherein x of the formula (1) is an epoxycyclohexylethyl group. [8] The calcined functional group-containing calcined compound according to any one of the above [3] to [6] wherein the weight average molecular weight (Mw) of the end (4) oxygen oil (8) of the formula (2) is 300 to 18 inches. The disproportionation σ containing a reactive functional group as described in any one of the above [8], wherein the weight average molecular weight (Mw) is from the group to the oxime. = the substituent on the polyoxo oxygen in the chain-like polyoxo-oxygen group in the gas-oxygenation of the reactive functional group as described in (1) or [2], which is a mercapto group or a base group Or both. 321483 8 201020279 [11] The reactive functional group-containing compound described in the above [1] or [1 〇]; wherein the sesquioxane moiety has reactivity with an epoxy group; The functional group contains an epoxycyclohexyl group. [12] A method for producing a reactive functional group-containing oxoxane compound, characterized in that the first-stage reaction system is a sterol-terminated polyoxo-oxygen oil (b) of the formula (2) The alkoxydecane compound represented by the formula (1) is in an amount of from 1.5 to 200 equivalents based on 1 equivalent of the decyl alcohol group of the polyoxyxanthene (b). Internally, β is condensed in the presence of a catalyst, and the second stage reaction is followed by adding water to the obtained reaction liquid to 'hydrolyze/condense the remaining alkoxy group.

2000) * In the formula, there are a plurality of enthalpy or different, each independently, which represents a linear, branched or cyclic alkyl group having a carbon number of 1 to 10, and a carbon number of 6 to 14 Base or carbon number 2 to alkenyl; m represents an average of 2 to XSi (〇R2) to 1 烧 of the alkyl group). (wherein, ί represents a reactive functional group having an epoxy group; and R2 represents a carbon number i [13,] a method for producing an oxygen-containing compound containing a reactive functional group as described in the above [12], wherein ' m is 2 to 200. [14] A method for producing a residue containing a reactive utero-energy group, which is a two-stage reactor of the following C 3 'step & reaction system, which gives the end of the formula (2) 321483 9 201020279 Polyoxymethylene oil (8)' and the oxygenated gas-casting compound (4) represented by the general formula (1) = and the silky compound (6) represented by the following formula (8), in terms of (four) base equivalent to the end of the gas (4) oxygen oil (8) The total equivalent of the aerobic compound (a) and (C) is in the range of L5 to 2 (10) equivalents, and the second stage reaction is carried out in the presence of a catalyst to carry out the enthalpy condensation reaction. In the obtained reaction product, the remaining alkoxy groups are hydrolyzed and condensed;

(2) (In the formula, there are plural numbers which may be mutually identical or mutually different, and are independent, representing a linear, branched or circular base of carbon number 1 to 1G, and a carbon number of 6 to 14 a base or a carbon number of 2 to 1 (); m represents a flat 200) XSi(〇R2)3 (1) R2 represents a hindrance number 1 (wherein X represents a reactive functional group having an epoxy group to 10 alkyl group) )

hSi (〇R2)3 (3) (wherein R4 represents a methyl group, a phenyl group; may be the same as or different from the formula (1), and each independently, representing an alkyl group having a carbon number of 丨 to 1〇) . [15] As described above, the method for producing a reactive oxygen atom-containing compound having a reactive ruthenium group according to [14], wherein the 'manufacturing step is a first-stage reaction and a second-stage reaction in a one-pot bait order . .

[Manufacturing method of the money-burning compound containing the anti-secret functional group as described in [n] to [15] above] wherein the "Oxygenated Wei compound" represented by the formula (1) is 321483 10 201020279 θ-(3, 4-ring Oxycyclohexyl)ethyltrimethoxydecane, or cold-(3,4-oxocyclohexyl)ethyltriethoxylate. [17] The method for producing a reactive functional group-containing oxoxane-compound according to the above [12] to [16], wherein the sterol terminal polyfluorene oxide of the formula (2), (13) R3 may be the same or different from each other, and is independently a thiol group or a phenyl group. [18] The method for producing a reactive functional group-containing oxoxane compound according to the above [13] to [15] wherein the alkoxydecane compound represented by the formula (3) is selected from the group consisting of methyl dioxane At least one of a group consisting of decane, phenyltrimethoxydecane, methyltriethoxydecyldecane, and phenyltriethoxydecane. [19] A curable resin composition comprising a siloxane compound (Α) containing a reactive functional group and a curing agent (Β) contained in any one of the above [^ to 丨]. [20] The curable resin composition according to the above [19], which further comprises a curing accelerator (C). [21] A cured product for a photo-semiconductor, which is obtained by thermally curing a curable resin composition of the above-mentioned [19] or [2]. [22] The optical semiconductor element is sealed with the cured product for an optical semiconductor described in the above [2〇]. [Effects of the Invention] The cured product of the curative resin composition of the Shixi gas compound has no stickiness or deformation, and is excellent in transparency, light resistance, and low modulus at low temperatures. . Therefore, the curable resin composition of the present invention is extremely suitable as an optical semiconductor sealing material. [Embodiment] 11 321483 201020279 [Best Mode for Carrying Out the Invention] A known cyclooxygenated compound containing a reactive functional group (hereinafter also referred to as "the invention of the invention" is in the middle molecule and is in the right-handed position. Anti-accumulator: The hydrolyzed condensed segment of the oxetene (preferably having a half-oxyalkylene group having an epoxy group). The h-dimensional network is doubled, and the invention of the oxygen compound compound's t-system becomes a three-dimensional network-like segment (referred to as a distribution of sesquioxanes in three-dimensional with 1 oxygen ^; Oxygen (10) is preferred as the core, and the chain-like polycene ==,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, The diarrhea compound is as described above, 31' has a three-burning oxygen-oxygen Xi Xiu ^ hydrolysis condensation segment (preferably sesquiter (10) segment) and the chain polyoxyl chain 1 again, from which the system is repeated Further, it may be referred to as a block type siloxane compound. The oxime compound of the present invention is, for example, a sputum sputum compound (a- Ι) represented by the following formula (10) (hereinafter also referred to as (four) The hetero (a-1)) is preferably an alkoxydecane compound (a) represented by the following formula (1) (hereinafter also referred to as alkoxydecane (a))' and a compound represented by the formula (2) The helium oxide oil (b) can be produced as a raw material. If necessary, the alkoxysilane compound (a-fluorene) (preferably as (a)) and the alkoxysilane compound represented by the above formula (3) can be used. c) and used as As raw material, XSi(Ri)n(0R2)3-„(10) (wherein 'X represents a reactive functional group having an epoxy group; Ri represents a substitution or 12 321483 201020279 unsubstituted carbon number 1 to 10 a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, or a substituted or unsubstituted carbon number 2 fluorene base; R2 represents a carbon number i to Π); η represents 〇 to 2 m soil When there are a plurality of plural, the plurality of ties may be mutually different or different from each other), XSi(0R 〇 3 (1) (wherein X and 匕 are synonymous with the above formula (1 〇)). In the oxygen generating compound of the present invention The chain (four) oxygen bond segment is formed by polyphosphorus oxygen oil (6), and the hydrolyzed condensation segment of the three alkoxylates is preferably a sesquiterpene-sintered segment, and a three-dimensional network The oxygen-burning bond segment is more preferable. It is preferably (4) by the calcined oxygen-sintering compound (5). (If necessary, the oxygen-burning stone compound (c) is used together (hereinafter also referred to as a calcined stone (c) When it is made of azepine oxide \1) ' is preferably formed by (a) and alkoxy decane (c)}. The cleavage bond is preferably the above-mentioned oxy-stone compound (4) Between (6), via Wei The bond between the hydrolysis of the base and the condensation of the ruthenium is formed by the hydrolysis condensation, so that the structural unit of x (the structure of the complex and the Α _ _ is a complex combination). The oxy-oxygen compound is referred to as sesquiterpene oxygenation, so the hydrolyzed condensation segment can be referred to as a sesquiterpene oxygenation chain segment. [, and 'each material will be described in detail. (a) Or alkoxydecane compound (a-1) or two as shown in (1). For example, it may be an organic group having an epoxy group, and there is no particular limitation on glycidyloxy carbon such as A glycidyloxyethyl group, r-glycidoxy oxygen X-ray, and glycidyloxybutyl group. Numbers 1 to 4 are based on glycidol. Soil '々~(3,4-epoxycyclohexyl)ethyl, 7-(3,4- 13 321483 201020279 Lytic hexyl)propyl, ^( 3,1 epoxycycloheptyl)ethyl, valence (3 epoxide cyclohexyl) propyl, stone-(3,4-epoxycyclohexyl)butane (3'4-hydroxyl) Cyclohexyl)pentyl or the like having a carbon number of from 5 to 5 substituted with a cycloalkyl group having an epoxy ring (epoxyether). The alkyl group having a carbon number of 1 to 3 substituted by a glycidoxy group or an alkyl group having a carbon number of 3 to 3 substituted by a cycloalkyl group having a number of oxime of 5 to 8 of the oxime, for example, 10,000-shrinkage Glyceryloxyethyl, glycidoxypropyl, cold (3'4%oxycyclohexyl)ethyl is preferred, and cold mono(3,4-epoxycyclohexyl)ethyl is particularly preferred. - The oxime in the formula (10) or (1), each independently, represents an alkyl group having a carbon number of 丨 to 1 Å, and may be any of a linear chain, a branched chain or a cyclic chain. Examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group and the like. From the viewpoint of reaction conditions such as compatibility and reactivity, the Rz is preferably a methyl group or an ethyl group, and particularly preferably a fluorenyl group. Further, in the case of the formula (1), the description of each group in the description of the following formula (2) can be directly cited. Preferred examples of the alkoxydecane represented by the formula (10) or (1) (aD or (3) include, for example, a dot-glycidoxyethyltrimethoxy decane, a stone-glycidyloxy group. Ethyl triethoxy decane, r _ glycidoxypropyl trimethoxy oxycarbazide, glycidoxypropyl triethoxy sulphur, cold one (3, 4-epoxycyclohexyl) Trimethoxy decane, 々-(if epoxycyclohexyl)ethyltriethoxy decane, particularly preferably p-(3,4-epoxycyclohexyl)ethyltrimethoxydecane. The alkoxyoxane compound (3) may be used alone or in combination with two or more kinds of decane (c) as shown in the following formula (3). The end of the structure represented by the following formula (2) has a chain-like polyoxyalkylene oil.

(wherein R3 and m are the same as those described above) In the formula (2), a plurality of R3s may be mutually the same or different from each other, and represent an aryl group having a carbon number of 1 to a carbon group of 6 to 14 carbon atoms. Or an alkyl group having a carbon number of 2 to 1 〇 and a carbon number of 1 to 10, for example, a straight-bonded, branched or precipitated condensed base having a carbon number of 1 to 1 Å, and examples thereof include a mercapto group and an ethyl group. , n-propyl octapropyl, n-butyl, isobutyl, t-butyl, tert-butyl, n-isopentyl, pentyl, n-hexyl, cyclopentyl, cyclohexyl, octyl, © Iethylhexyl, fluorenyl, fluorenyl and the like. When considering light resistance, soil, ethyl or cyclohexyl is preferred. Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group, an anthracene group, a p-phenylene group, and a diphenyl group. Carbon number 2 based vinyl, alkenyl, and the like. Examples of the alkenyl group to 10 include, for example, a vinyl group, a methallyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, and the like, and a heat resistance. It is preferably a phenyl group, a ring p « 7 τ I, a hexyl group or a n-propyl group, particularly preferably a fluorenyl group or a phenyl group. Specifically, 321483 15 201020279 is a case where two R3 of the formula (2) are a mercapto group or a phenyl group, or one of which is a methyl group and the other is a stupid group. The combination of these is generally the case where the overlapping units are all the same combination, however, as long as the effect of the present invention is achieved, different combinations can be mixed in the repeated cases. For example, even if the individual reversing units are different, the foreign matter can be mixed regularly or randomly. The compound of the formula (2) has an average value of 2 to 2 Å, preferably 2 to 2 Torr, more preferably 3 to 1 Torr, and particularly preferably 3 to 5 Å. When the μ value is too low, the hardened material is too hard to deteriorate the low modulus of elasticity. When the enthalpy is too high, the hardened material tends to deteriorate in mechanical properties. The weight average molecular weight (Mw) of the polyoxygenated oil (b) is generally in the range of 3 Torr to 50,000, preferably in the range of 3 Torr to 3 Torr, and is determined from 3 Å to 18,000 (GPC measurement). The range of values) is better. Among these, if the elastic modulus at low temperature is considered, the molecular weight is preferably 3 〇〇, and further consideration is given to the compatibility of the composition physicochemical, preferably 3 〇〇 to 5 ,, especially 500 to 3000 are particularly good. When the weight average molecular weight is less than 3 Å, the characteristics of the chain poly-stone chain forging portion cannot be exhibited. The molecular weight of the polyoxime oil (b) of the present invention is a weight average molecular weight (Mw) of the converted polyethylene according to the following conditions using GPC (Gel Permeation Chromatography). Various conditions of GPC: Shimadzu Corporation column: guard column (guardcolumn) SH0DEXGPCLF-GLF-804 (3) Flow rate: 1. 〇ml/min. 321483 16 201020279 Column temperature: 40 °C Solvent: THF ( Tetrahydrofuran) Detector: RI (Differential Refractive Detector) The viscosity of the polyoxygenated oil (b) is preferably in the range of 10 to 200 cSt. Better than 30 to 90 cSt. When the viscosity is too low, the viscosity of the target ascorbic oxide compound of the present invention is also low, and it is not suitable for the case of the optical semiconductor encapsulant. On the contrary, when the viscosity is too high, the viscosity of the block type antimony-oxygen compound (A) is high. It rises and has a tendency to hinder operability. Specific examples of the polyfluorene end-terminated dimercaptopolyoxyl oil when R3 of the polyoxyxane oil (b) is a mercapto group include the following product names. For example: Dongli Dao Kang Ning Poly Oxide (shares) products are PRX413, BY16-873; Shin-Etsu Chemical Industry Co., Ltd. products are X-21-5841, KF-9701; Momentive (M0MENTIVE) (shares) have XC96-723, TSR160, YR3370, YF3800, XF3905, YF3057, YF3807, YF3802, YF3897, XF3905; ❹ Gelest products are DMS-S12, DMS-S14, DMS-S15, DMS-S21, DMS-S27, DMS-S31, DMS-S32, DMS-S33, DMS-S35, DMS-S42, DMS-S45, DMS-S51, etc. Preferable specific examples of the polyoxonium-terminated methyl phenyl polyfluorene oxide in which R 3 of the polyoxygenated oil (b) is a methyl group and a phenyl group include the following product names. For example: the products of Momentive (shares) are YF3804;

The products of Gelest are PDS-0332, PDS-1615 and so on. The polyoxydeoxy-terminated diphenylpolyoxyl oil having a polyoxyxane oil (b) wherein R 3 is a phenyl group can be exemplified by PDS-9931 of Gelest as a specific example of the preferred product name 17 321483 201020279. In the above specific examples, from the viewpoints of molecular weight and dynamic viscosity, it is preferably PRX413, BY16-873, X-2, 584, KF-97 (H, XC96-723, YF3800, YF3804, DMS-S12, DMS-S14). , DMS-S15, DMS-S21, PDS-1615. Among these, 'because of the characteristics of the softness of the polyoxygen chain forging, from the viewpoint of molecular weight', X-21-584, XC96-723, YF3800, YF3804 DMS-S14 and PDS-1615 are particularly preferred. These polyoxyxane oils (b) may be used singly or in combination of two or more. Next, the alkoxy decane compound (c) will be described in detail. The compound (c) has a structure of the following formula (3): R4Si(〇R2)3 (3) R4 in the formula (3) represents a fluorenyl group or a phenyl group. R2 and a formula of the formula (3) 1〇) or (丨) may be the same or different, each independently, representing an alkyl group having a carbon number of 丨 to 1〇, which may be linear, branched or cyclic. The preferred group and the preferred group are the same as those exemplified in the description of the above formula (10) or (1). Preferred examples of the compound (c) of the oxime compound are exemplified by methyltrimethoxy group. Decane, The above is preferably trimethylmethoxydecane, phenyldiethoxysilane or phenyldiethoxydecane. In the above, it is preferably calcined with methyltrimethoxydecane or phenyldiazepine. In order to adjust the molecular I of the block type siloxane compound (A), the compatibility at the time of forming a composition, and the heat resistance, the viscous property, the low moisture permeability, the low gas permeability of the cured product, etc., the alkoxy decane compound ( c) may be used in combination with a pyrochlore compound (a-Ι), preferably (a). Relative to the sum of alkoxysilane compounds ((&amp;-υ, to (&) and ((〇之321483 18 201020279 The sum is better), the alkoxydecane compound (c) is used in an amount of from 〇 to 70 mol%, preferably from 0 to 55 mol%, more preferably from 〇 to mol%. When the compound (c) and the hospital oxygen-suppressing compound (a) are used, the sum of the alkoxydecane compound (c) is preferably in the range of 5 to 70 mol% to 5 to 50 mol. The ear % is more preferably 10 to 40 mol %. The following is a description of the method for producing the 5 o'clock oxygen-burning compound of the present invention. The alkoxysilane compound of the present invention may be the alkoxyoxane compound v (a-1) (hereinafter also referred to as alkoxydecane (a-1)) as an alkoxydecane (a) (hereinafter also referred to as alkoxydecane (a)). And the above-mentioned polyoxyxane oil (b) is used as a raw material, and the above alkoxylated oxane compound (c) can be used as a raw material as needed. The manufacturing system of the oxirane compound of the present invention can be produced. The above-described two-stage segment of the present invention may be any of the methods described above. The most suitable method is as described above for the 'stage-by-step reaction of the two-stage reaction'. The first-stage reaction system is to make the sterol-terminated polyoxyl oil (b) and the oxalate (a 1) (a) Preferably, and according to the desired pyrochlore (c), the oxygenated equivalent of the above-mentioned chopped chopping compound is 1. 1 equivalent to the decyl alcohol group of the polyoxyxamic oil (b) at the end of the broken alcohol. The reaction and condensation are carried out in the range of 5 to 200 equivalents, and the second stage reaction thereafter is carried out by adding water to the obtained reaction liquid to hydrolyze and condense the remaining alkoxy group (one-pot method). In the case where the first-stage reaction "in the absence of water", it is preferably carried out in the presence of an acid catalyst or a catalyst (preferably a base catalyst). The alkoxynonane (a-fluorene) of the above first-stage reaction is preferably (a) [due to the use of alkoxydecane (C) as required by 321483 19 201020279] and the polyoxyxane (b) The ratio of the alkoxydecane compound to the polyoxyxane oil (b) is generally 1 equivalent to the decyl alcohol group of the polyoxyxanic oil (b), and the alkoxydecane (a-fluorene) is preferably (a). The alkoxy equivalent of alkoxy decane (c) is used in combination with the alkoxy decane (c), alkoxy oxane (a-1), preferably (a), with alkoxy decane (c) The total alkoxy group equivalent weight) is from 1.5 to 200 equivalents, preferably from 2 to 200 equivalents, more preferably from 2 to 150 equivalents, still more preferably from 2 to 100 equivalents. Further, the ratio is 1 equivalent to the sterol group of the polyoxyxane oil (b), and the alkoxy decane compound may have an alkoxy equivalent of 3 to 100 equivalents, preferably 4 to 100 equivalents, and 5 to 100. The equivalent is better. When the amount of the alkoxysilane compound is greatly exceeded the above upper limit range, the resultant may lose the preferred physical properties of the alkoxysilane compound of the present invention. _ Patent Document UW02005/100445, discloses that, without using a sterol terminal polyoxosulfuric acid (b), a chopping compound having an epoxy group and a decane compound having no epoxy group are simultaneously carried out in the presence of water. Hydrolysis condensation. In general, in the synthesis of a sesquiterpene having a functional group, as in Patent Document 1, a alkoxysilane compound having a functional group is simultaneously subjected to hydrolysis condensation with an alkoxysilane compound having no functional group in the presence of water. . However, according to the present invention, in addition to the alkoxydecane (a-fluorene), it is preferred that (a) is used [in response to the desired alkoxyoxane (c)], and when the polyoxygenated oil (b) is used as a raw material, These materials are reacted together in the presence of a catalyst and water. Because of the alkoxydecane (a-fluorene), (a) is preferred [in response to the desired alkoxyoxane (c)] hydrolysis between the alkoxy groups. The condensation reaction proceeds preferentially, and sometimes the formed sesquiterpene oxide 20 321483 201020279 calcined compound and the unreacted polysulfuric acid (b) remain incompatible with each other and tend to produce uneven white turbidity compounds. Such a white turbid organic polymer; g oxy-oxygen is not suitable for optical use. Further, even if the transparency is not affected, the synthesized compound tends to have a reduced molecular weight, and the heat resistance is lowered and the "stickiness" is caused, and it is difficult to obtain a preferred oxoxane compound of the present invention. Including the above-described optimum method, the method for producing the reactive functional group-containing oxanthene oxide compound of the present invention is preferably a production step shown by the following (i) and (ii). Manufacturing step (i): the alkoxysilane is subjected to alkoxysilane modification by a dealcoholization condensation of a decyl alcohol-terminated polyoxyl oil with the above alkane gas to form an alkoxysilane modified body (d). Step (chain-like polyoxygen segment formation step), 'manufacturing step (ii): performing a hydrolysis between alkoxysilane modified substance (d) and an alkoxy group in the above alkoxydecane compound in the presence of water Condensation, © a step of forming a hydrolyzed condensed segment of the pyrotechnic sinter (preferably, the oxysulfonation chain is preferred). The manufacturing steps (i) and (ii), regardless of the order, can be carried out only through the respective steps. Alternatively, depending on the situation, the sterol oxy-oil (b) may be reacted with the above-mentioned oxy-moulding compound by a method of sequentially dropping water droplets, etc., so that the reaction of the above-mentioned manufacturing steps (i) and (ii) is one. The steps are carried out. In the summer, in (!), when the above alkoxy decane is used instead of the alkoxy oxime, and the halophilic 7-oxygen aldehyde is substituted with two or more alkoxy groups, only the inflammatory 21 321483 201020279 (i) may be produced. The oxoxane compound of the present invention is obtained. The preferred production method includes the above-described optimum method, and specifically, the following three production methods are exemplified: &lt;Production method (A)&gt; First, the production step (i): a polyoxyloxy oil having a sterol group at the terminal (b) with a dealcoholization condensation reaction with alkoxy oxane (a) [which can be used in combination with alkoxy oxirane (c), as desired, by converting the end of the polyoxyxane oil to an alkoxy oxane Body (d). Next, the production step (ii) is preferably carried out in the coexistence of alkoxysilane (a) [which can be used in combination with alkoxysilane (c)] to produce the polyoxyxene oil obtained in the step (i). And the alkoxy group of the alkoxy oxane modified product (d) or the alkoxy oxane modified product (d) and the alkoxylated compound of the alkoxysulfan compound in the presence of the alkoxydecane compound, In the presence of water, by carrying out a hydrolysis condensation reaction, a chain polyphosphonium chain segment is formed [usually represented by -(0Si(R3)2)ra- (R3 represents synonymous with formula (2)) and an alkane The present invention for the hydrolyzed condensation segment of oxoxane (preferably a sesquioxane chain segment) is a method for the synthesis of a compound. <Manufacturing Method (B)&gt; First, the following steps are carried out: alkoxyoxane (a) [may be used in combination with phosgene (c) in the presence of water] to carry out a hydrolysis condensation reaction between the alkoxy groups in the presence of water Further, a hydrolysis condensate of alkoxyoxane having an alkoxy group in the molecule (preferably sesquioxane (e) is preferred). Secondly, the preferred method of preparation is to separate the alkoxydecane hydrolyzed condensate (preferably sesquioxane (e)) as described above, and further preferably, in the absence of water 22 321483 201020279 (4) The oxygen oil (6) and the oxidized oxygen stone of the upper lysate. (4) The hydrolysis condensate (preferably sesquiterpene gas (4) is preferred) to carry out the dealcoholization condensation reaction to obtain the oxoxane compound of the present invention. <Manufacturing Method (C)&gt; First, the manufacturing step (1) is carried out: in the presence of the above-mentioned oxygen-burning stone court in the absence of water, the poly-stone-oxygen oil (8) having an anthracene group at the end and the alkoxy group are preferably present. The decane (a) [may be used in combination with the alkoxy decane (c)] to carry out a dealcoholization condensation reaction to form the above alkoxy oxane modified body ((1), followed by a production step (11): in water In the presence of 'by the residual pyrithione (a) [when the oxygenated Wei (6) is used in combination, the remaining courtyards (a) and (c)] and the above alkoxy decane are modified. The plastid (the hydrolytic condensation reaction between the alkoxy groups of (1), the one of the oxoxane compounds of the present invention is obtained. In the present invention, from the viewpoint of shortening the production steps, it is preferred that the separation is not carried out. The first-stage reaction is carried out directly in the first-stage reaction, and the reaction is carried out in a one-pot manner in sequence. ❿ Hereinafter, a specific production method (C) (the above-described preferred production method) will be further described. The manufacturing step (i) is used as the second-stage reaction, and the manufacturing step (ii) is used as The two-stage reaction, first in the first-stage reaction (manufacturing step (1)), the deco-alcoholization of the polyoxyxane oil (b) with the alkoxy oxane (a) [in response to the desired alkoxy decane (C)] The gas atom of the sterol group at the end of the polyoxygenated oil (1)) is converted to a calcined oxygen stone to obtain a burned oxygen stone modified body (d). In the first stage reaction, 'preferably The reaction is carried out without adding water, so that there is no hydrolysis condensation between the alkoxy groups, and 1 equivalent of the sterol group is used. When the reaction is carried out in a hospital of 321483 23 201020279 oxy 3 equivalents or more, the alkoxy oxane modified body is considered to be The structure exists as shown in the following formula (4), and it is considered that after the formation of such a modified body (d), it is preferred to carry out hydrolytic condensation between alkoxy groups. Therefore, relative to the polyoxygenated oil (b) The sterol group is 1 equivalent, and the reaction is preferably one of the reaction using 3 to 200 equivalents of the alkoxy group. r2o r6 Si-Ο OR2

(4)

In the formula (4), R2, R3 and m are the same as those described above, and R6 may be the same or different and each independently represents the above X and/or 1?4. In the first-stage reaction, when the alkoxy group is reacted in an amount of less than 1.0 equivalent based on 1 equivalent of the sterol group, the alkoxy group is not present at the end of the first-stage reaction, and the first step cannot be reached. a two-stage reaction, and, if the alkoxy group is reacted between 1.0 and 1.5 equivalents, the alkoxyoxane (a) [in response to the desired alkoxyoxane (c)] The base reacts with the sterol group of the polyoxygenated oil (b), and at the end of the first-stage reaction, gelation occurs due to excessive formation of the polymer. Therefore, it is necessary to react with an alkoxy group of 1.5 or more with respect to 1 equivalent of the sterol group. From the viewpoint of controlling the reaction, it is preferably 2.0 equivalent or more. The hydrolyzed condensed segment of the alkoxysilane is preferably 3 equivalents or more, and 4 equivalents or more, based on 1 equivalent of the decyl alcohol group, from the viewpoint of forming a preferred sesquiterpene gas chain segment. Good, more than 5 equivalents. Meanwhile, the sesquiterpene gas chain segment in the present invention may be any structure of a so-called ladder type 24 321483 201020279 type, a cage type partial ring opener or a random type, and is generally considered to be such a mixed type. After completion of the first-stage reaction, water is directly added to the reaction liquid to carry out a second-stage reaction (manufacturing step (丨丨)) of hydrolysis condensation between alkoxy groups. The amount of addition of 1 equivalent of water to the oxygen-burning base of the pyrochlore compound used as the above-mentioned raw material is about 0.5 to 1 equivalent. The amount of water required for the hydrolytic condensation of the residual alkoxy group after the end of the first-stage reaction is preferably from about 1 to about 10 times (more preferably from about 1 to 5 times). It is considered that the reaction shown in the following stage (丨) to (πΐ) is caused in the second-stage reaction. (I): a hydrolysis condensation reaction between alkoxy groups of alkoxyoxane (a) remaining in the system (and alkane-oxydecane (c) when used in combination). (Π): an alkoxysilane modified product obtained by the first-stage reaction (the azide hydrolyzed condensation reaction with the alkoxysilane (a) (and the alkoxy group of the alkoxysilane when used in combination). ): the alkoxyoxane (a) formed by the reaction of the alkoxysilane modified product (d) obtained in the first stage reaction with the above (I) (and the alkoxyline (c) when used as a silver a) a condensation reaction between alkoxy groups of the hydrolysis condensate. In the second-stage reaction described above, the reaction is recombined, and the hydrolysis and condensation segment is carried out with k (the sesquiterpene oxygenation segment is preferred) And the formation of the chain-type polyoxynoxy group derived from the polyoxyxane oil (b). The block type siloxane compound of the present invention produced by the first stage reaction and the second stage reaction The cured product obtained by using the resin composition of the compound 25 321483 201020279 is excellent in transparency and low modulus of elasticity. The production of the block type siloxane compound having a reactive functional group of the present invention is Can be carried out without catalyst, but the reaction is slow when there is no catalyst, shortened by From the viewpoint of time, it is preferable to carry out in the presence of a catalyst. The catalyst which can be used can be used as long as it is an acidic or basic compound. Examples of the acidic catalyst include hydrochloric acid. An inorganic acid such as sulfuric acid or nitric acid; and an organic acid such as citric acid, acetic acid or oxalic acid. Examples of the alkaline catalyst include sodium hydroxide, potassium hydroxide, lithium argon oxide, and alkali metal hydroxide of cerium hydroxide; Such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, alkali metal carbonate of potassium hydrogencarbonate, inorganic bases such as ammonia; triethylamine, diethylenetriamine, n-butylamine, diammonium ethanol, triethanolamine, hydrazine oxidation An organic base such as tetramethylammonium. Among these, in particular, from the viewpoint of easiness of removing the catalyst from the product, an inorganic base is preferred, and sodium hydroxide or potassium hydroxide is more preferred. The amount of the alkoxy oxane (a), which may be used in combination with the alkoxy decane (c), is generally 0.001 to 7.5 wt%, and is 0.01 to 5% by weight. Preferably, the addition amount may be about 0.01 to 1% by weight. It is preferably added in a state of being dissolved in a solvent or the like, and it is preferably added in a state in which the catalyst is dissolved in an alcohol such as decyl alcohol, ethanol, propanol or butanol. When the aqueous solution is added, as described above, the condensation of the calcined stone (a) (the calcined stone (c) if necessary) is unilaterally carried out, and the sesquiterpene generated thereby The oligomer and the polyoxygenated oil (b) are immiscible and may be cloudy. 26 321483 201020279 The production of the reactive functional group-containing oxoxane compound of the present invention can be carried out without a solvent or in a solvent. A solvent is added in the middle of the production step. The solvent is a solvent capable of dissolving the alkoxysilane compound (a), the polyfluorene gas (b) (and alkoxysilane (C) may be used in combination), and the alkoxysilane modified product (d). It is better. Examples of such a solvent include, for example, an aprotic polar solvent such as dimethyl decylamine, dimercaptoacetamide or tetrahydrofuran; such as mercaptoethyl ketone, methyl isobutyl amide, and cyclopentane Ketones such as ketones; esters such as ethyl acetate, butyl acetate, lactic acid ethyl acetate, and isopropyl butyrate; such as methanol, ethanol, propanol, butanol, etc.; such as Jiyuan, cyclohexane, toluene Hydrocarbons such as diphenylbenzene. In the present invention, it is preferred to carry out the reaction in an alcohol, and it is more preferable to use methanol and/or ethanol from the viewpoint of reaction control. The amount of the solvent to be used is not particularly limited as long as the reaction proceeds smoothly, and the alkoxyoxane compound (a) (can be used in combination with the oxydecane (c)) and the polyoxygenated oil (b) The total weight of 100 parts, generally 'used to 〇 to 〇 by weight. The reaction temperature varies depending on the amount of the catalyst, but it is usually from 20 to 160 ° C and from 40 to 14 Torr. (: 隹, especially 50 to 15 〇❹ c. Further, the reaction time is generally from i to 40 hours in each manufacturing step, preferably from 5 to 30 hours. After the reaction is completed, it is neutralized as needed. And/or washing with water to remove the catalyst. When washing with water, it is preferred to add a solvent which can be separated from water depending on the type of solvent to be used. Examples of preferred solvents include, for example, mercaptoethyl _, methyl iso Ketones such as butanone and cyclopentanone; esters such as ethyl acetate, butyl acetate, lactic acid ethyl acetate, and isopropyl butyrate; such as hexane, cyclohexanol, toluene, xylene, etc. Catalyst removal can be carried out only by washing. However, since 321483 27 201020279 is reacted under acidic conditions, test conditions or any of the conditions, it is washed with water after neutralization, or after adsorbing the catalyst with an adsorbent. It is preferred to remove the adsorbent by filtration. When the adsorbent is used, the adsorbent is added to the reaction solution and stirred, heated, etc., after the catalyst is adsorbed, the adsorbent is filtered, and the residue is washed with water, thereby removing the catalyst. , adsorbent. Acidic or inspective compounds. Examples of the compound which exhibits acidity include inorganic acidic compounds such as hydrochloric acid, sulfuric acid, nitric acid, scalylic acid, and dihydrogen hydride; or organic acids such as formic acid, acetic acid, and oxalic acid. Examples of the compound include, for example, alkali metal hydroxides such as sodium cesium hydroxide, potassium hydroxide, lithium hydroxide, and cesium hydroxide; for example, sodium chloride, potassium carbonate, sodium cesium carbonate, potassium hydrogencarbonate, etc. An inorganic base such as an alkali phosphate such as disodium hydrogen phosphate, trisodium phosphate, polyphosphoric acid or sodium tripolyphosphate; or ammonia, triethylamine, diethylenetriamine, n-butylamine or diamyl An organic base such as aminoethanol, triethanolamine or tetramethylammonium hydroxide. Among these, in particular, from the viewpoint of easy removal from the intended product, an inorganic base or an inorganic acid compound is preferred, and more preferably. It is easier to adjust the @pH to a sodium phosphate or a phosphate such as the above-mentioned alkaline phosphate in the vicinity of neutral. The adsorbent can be exemplified by a synthetic adsorbent such as activated clay, activated carbon, zeolite, inorganic or organic. Ion exchange Specific examples of the resin include the following products. Examples of the activated clay include, for example, Dongxin Chemical Co., Ltd.: activated clay (8 persons 35, 3 persons 1, 1 ', feet -15 or £), or Nikon Knight (0-36, G-153 or G-168); Mizusawa Chemical Industry Co., Ltd. Goods: Galleon 28 321483 201020279

Earth, or Mizuka AceRTM (superscript RTM stands for registered trademark. The same applies below).

Examples of the activated carbon include, for example, Ajinomoto Fine Chemicals Co., Ltd., CL-H, Y-10S, or Y-10SF; Futamura Chemicals Co., Ltd., S, Y, FC, DP, SA1000, K, A, KA, Μ, CW130BR, CW130AR or GM130A. Examples of the zeolite include the products of Union Showa (Molecular Sieve 3A, 4A, 5A or 13X). © Examples of synthetic adsorbents, such as: Concord Chemicals (stocks):

KyowardRTM 100, 200, 300, 400, 500, 600, 700, 1000, 2000; and Rohm and Haas stocks: AmberlystRTM 15JWET, 15DRY, 16WET, 31WET, A2:1, AmberliteRTM IRA40, 0JC1, IRA403BLC1, IRA404JC1 And Dow Chemical (stock) products: DOWEX RTM 66, HCR-S, HCRW2 or MAC-3. After the completion of the reaction or after the neutralization, it can be purified by other conventional U separation and purification means which are washed with water and filtered. Examples of the purification means include column chromatography, concentration under reduced pressure, distillation, and extraction. These purification means may be carried out singly or in combination of plural kinds. When a solvent mixed with water is used as a reaction solvent, it is preferred to carry out the reaction in the reaction system after the neutralization and distillation or concentration under reduced pressure to remove the reaction solvent mixed with water from the reaction system. The solvent for water separation is obtained by dissolving the desired reaction product and then washing it with water. After washing with water, the solvent used above is removed by concentration under reduced pressure or the like, whereby the reactive functional group-containing oxalate compound of the present invention can be obtained. 321483 29 201020279 The appearance of the oxime compound of the present invention is generally a colorless, transparent liquid having a fluidity at 25 ° C. The oxime compound of the present invention obtained in the above reaction is a block type siloxane compound having a reactive functional group as described above, which is characterized in that it is composed of a bond-like polyoxygen chain segment, preferably a system - (S i (R3)2〇)m- [R3 and m represent a bond-like polyoxo-oxygen segment represented by the above formula (2), and (1^8丨〇3/2) as a structural unit: 〇 [[1^ is synonymous with the above formula (4); nx represents a sesquiterpene oxide segment represented by an average of 2 to 2 Å], and at least a part of the sesquiterpene oxygenated segment has at least A reactive functional group of an epoxy group. The number of reactive functional groups having an epoxy group represented by X of the above-mentioned calcined oxygen compound (a) in the sesquiterpene oxygenation chain segment, relative to the sesquiterpene oxygenation segment One helium atom, the average ratio of 0.3 to i is better, and the ratio of 〇45 to 1 is better, and the ratio of 0.6 to 1 is particularly good. Further, it is derived from an alkoxysilane (the group represented by L in the oxime, and the ratio of 〇 to 0.7 is preferably on the average of 矽 to 〇55 with respect to one 矽 atom in the sesquioxane chain segment. Preferably, it is particularly preferably in a ratio of 0 to 0.4. The preferred molecular weight of the inventoxane compound, the average molecular weight of the helium measured by Gpc is from about 5 to about 20,000, and preferably about 20,000. It is better to lingo to loooo, and even f right. When the weight average molecular weight is too low, the heat resistance is lowered, and when the temperature is too high, the viscosity will rise due to the increase in viscosity. The weight average molecular weight is Gpc (condensation). Gel permeation chromatography) Weight average molecular weight (Mw) of polystyrene according to the following conditions. Various conditions of GPC 321483 30 201020279 Manufacturer: Shimadzu Pipe Column: Protection tube 杈 SHODEX GPC LF-G LF- 804 (3 pieces) Flow rate·· 1. Column temperature: 40. 〇 Solvent: THF (tetrahydrofuran) Detector: RI (differential refraction detector)

The epoxy equivalent of the oxalate compound of the present invention (determined by the method described in JIS K-7236) is preferably from 300 to 1600 g/eq, more preferably from 400 to 1 〇〇〇g/eq, and further preferably 450 to 900 g/eq is especially good. When the amount of the epoxy is too small, the hardened material is too hard and the low modulus of elasticity is inferior. When it is too large, the mechanical properties of the cured product are deteriorated. The viscosity of the oxirane compound of the present invention (E-type viscometer, measured at 25 ° C) is generally about 50 to 2 〇〇〇〇 mPa · s, preferably from about 15 〇 to about 100 MPa·s, to 2 〇〇 to 1〇〇〇〇mpa · s is better, and it is best to be around 200 to 5_mPa·s. Also, sometimes it is better to use 500 to l〇_mPa.s, and it is especially good to delete _.5 from _ to 5. The atom of the oxygen-conducting 3 chain segment (preferably, the cleavage oxygen (10) segment) and the three oxygen atom-bonded atoms belonging to the present invention are relative to all the stone atoms, and the ratio may be 5 to 95% or so, for the sealing of the light body components, 5 to 5 to 8 to 30 mol% is better, and the bucket % is divided into chains which are particularly good for the oxygen. "Storage (4) ^ Oxygen pure wealth of wealth (four) sub ^ 321483 31 201020279 sesquiterpene oxide chain with 3 oxygen atoms bonded to the part of Shi Xi atom, the ratio is lower than 5 Moco, chain When it is used as a composition of the following curable wax composition, the cured product of the blush composition tends to be too soft, and it is sticky or damaged. On the other hand, when it is higher than 5G mol%, the result of the cleavage of the oxidizing resin == is strongly exhibited. When used as a curable resin group as follows: the cured product of the fat composition is too hard to make the low-rate characteristic inferior, and thus heat The results of the cycle test tend to deteriorate. ❹本,明之石夕氧烧化合物的系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系系Reactive oxygen containing an epoxy group: the ratio of the two-chain polyoxyl segment in the present invention. The object, which is suitable for the sealing of the optical semiconductor, is also characterized by a large characteristic of the above-mentioned (four) all of the Shixia original cans of the compound; the two-in-one segment (preferably the doubling (tetra) oxy-oxygen segment) Shishi atom:=, 50% of the time 'belongs to the key polycene', the proportion of the scoop is 50 to 95 mol%. It belongs to the key flat #畜=一_为7〇-莫二: In the two bond segments of the raw material ===, the stone atomic ratio is the same as that of the compound, and the element can be equal to the == New Zealand (1)-species containing the reverse: the second is as follows. The base of the oxylate compound has the following: Chain-like poly 321483 32 201020279 hydrazine segment, hydrolyzed condensed segment of tris(C-C10) alkoxy decane with a group of reactive functional groups of epoxy groups, methyl groups and phenyl groups And the at least a portion of the hydrolyzed condensed segment is a segment containing a reactive functional group having at least one epoxy group. ' (ii) as described in (i) above a siloxane compound containing a reactive functional group, wherein the chain polyoxy oxymethylene segment is a segment represented by the following formula (2A), and one (Si(R3)2〇)m-(2A) 〇 After Identical or mutually different, representing a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms or a dilute group having 2 to 1 carbon number; m represents an average value of (2) A compound having a reactive functional group as described in the above (丨丨), wherein R3 is a carbon number of 1 to 10, m is an average of 2 to The reactive functional group-containing oxoxane compound according to any one of the above (i) to (iii), wherein R3 is a fluorenyl group. (v) as described above (i) to (iv) The reactive functional group-containing smouldering compound according to any one of the preceding claims, wherein the 'reactive functional group having an epoxy group is substituted with a cycloalkyl group having a carbon number of 5 to 8 An alkyl group having 1 to 3 carbon atoms.

Vl) as recited in any one of the above (i) to (iv), which has a ruthenium-containing, functional group-based oxy-burning compound having a reactive functional group selected from the group consisting of an epoxy group-containing reactive functional group a tri(C1-C10) alkoxydecane having a methyl group and a group of a phenyl group having a carbon number of 1 to 5 substituted by a cycloalkyl group having 5 to 8 carbon atoms of an epoxy group a tris(C1-C10) alkoxydecane. U) a reactive functional group-containing oxime, an oxygen compound, a glycerol, and a 'having an epoxy group-containing carbon number 5 to 8 as described in (vi) above. Cycloalkyl substituted 33 321483 201020279 Tri(C1_C10) alkoxydecane lanthanide of a C 1 to 3 alkyl group - (3,4~epoxyduccinyl)ethyltrimethoxylate. (vi ii) The oxo-oxygenated compound containing a reactive functional group as described in any one of the above (i) to (vi i), which has a reactive functional group selected from an epoxy group-containing group, a methyl group, and a tri(n-cl0) alkoxydecane having a phenyl group as a group having a reactive functional group containing an epoxy group, a tris(cl_cl〇) alkoxy group, and having a group selected from a fluorenyl group and a stupid group Both of the three (cl_cl〇) alkoxydecane groups in the group. (IX) The reactive functional group-containing oxoxane compound according to the above (vii i), wherein the tri(C1-C10) alkoxy group having a group selected from the group consisting of a methyl group and a phenyl group A decyl phenyl trimethoxy decane or a methyl trimethoxy sulphate. The reactive functional group-containing oxazepine compound according to any one of the above (i) to (ix), wherein the weight average molecular weight measured by GPC is from 5 Å to 20,000. (6) The reactive oxygen-containing compound of the above-mentioned (1) to (1) is obtained by the following two-stage reaction, and the i-stage ❹ reaction system is represented by the general formula (2) The dream alcohol terminal polyoxyxane oil (b) and the pyrochlore compound (a) represented by the general formula (1) are compared with the sterol terminal polysulfide oil (the equivalent of the stone base alcohol group) The oxygen-containing compound q has an oxygen equivalent of i 5 to _ equivalent and reacts and condenses 'the second stage of the reaction is followed by adding water to the obtained reaction liquid to 'hydrolyze and condense the remaining alkoxy group; 321483 34 ( 2) 201020279

(In the formula, there are a plurality of scorpions which may be mutually identical or mutually different, and the linear, branched, and filaments of the watch, and the thin base of the number of wires; 2, represent the square of the average of 2 to _) or Stone anti-XSi(〇R2)3 (1) ❹ ❹ =: a reactive functional group having an epoxy group; a reactive hydroxyl-containing terminal described in the number 1. 1 The permeation layer _ has a weight average molecular weight of _ to _. The oxygen-burning character described in the character of the reactive functional group is 1 equivalent, and the formula is -2 to the equivalent equivalent of the base alcohol group of the endstone polyoxosulfuric acid (b). (4) The equivalent of the alkoxy group of the compound (a) of the formula (a), wherein the oxy-fired compound containing the reactive group I group as described in any one of the above (X1) to (Xlii) is represented by the formula (2) _ alcohol end polyglycol

Mb) is a xylenol terminal dimethyl polyphosphite or a linalool-terminated methyl phenyl polysiloxane. The reactive functional group-containing oxoxane compound according to any one of the above (xi) to (xiv), wherein the alkoxy decane compound represented by the formula (1) (the phantom glycosyloxyethyl three)曱oxydecane, _glycidoxyethyl diethoxy decane, glycidoxypropyl trimethoxy decane, 35 321483 201020279 glyceryl lactyl propyl triethoxy sulphate H (3,4- Epoxycyclohexyl dimethyloxycarbazide or stone-(3,4-epoxycyclohexyl)ethyl oxane. ^

Om) The reactive oxy-energy t-oxygen compound as described in any one of the above items (1) to (x) wherein 'the first-stage reaction system is a gas-based oil (b) represented by the formula (2) 'With the formula (1) shown in the formula (1) = and the general formula (3), the oxy-wet compound (6), in relation to the base of the base alcohol (8), the amount of the base # i, the green Wei compound (4) to ^ (C) The total equivalent of the alkoxy group is 15 to 2 (10) equivalents. The reaction is condensed and then y. The second stage is reversed. (IV) is added to the obtained reaction solution to hydrolyze and condense the remaining alkoxy groups:

(2) (wherein a plurality of R3s may be mutually identical or mutually different, and represent a carbon number ι to ι〇 branched or cyclic alkyl group, a carbon number 6 to 14 aryl group or a carbon alkenyl group; m Indicates an average value of 2 to 2 〇〇), (1) an energy group; R2 represents a carbon number of 1 XSi(〇R2)3 (wherein, X represents a reactive group having an epoxy group to 10 alkyl groups), R ^Si (0^2)3 (3) In the middle of the day, it means a methyl group or a phenyl group; and R2 may be independently or different from the formula (1), and each represents a carbon number of 1 fluorene. For example, a hard oxygen-fired 321483 36 201020279 compound containing a reactive functional group as described in the above (XV1), which has a sterol terminal represented by the formula (2)

Or (xiv) the polyoxygenated oil described. The half-w-system (XII == (:, V11)-containing reactive functional group =: loading:: combining: formula (1), - (4) (4) as in (4) to (xviii) above - In the case of the oxy-oxygen compound (6), the oxygenated oxonium compound (6) represented by the formula (3) is methyl dimethoxy decane or phenyl trimethoxy decane. Next, the curable resin composition of the present invention will be described. The money-burning compound of the present invention can be used as a component of a curable resin composition. The following description of the composition of the sclerosing sulphur compound of the present invention is referred to as "the present invention" Oxygen-burning compound (1)". At this time, the compound of the Xixi oxygen-burning compound (produced as 2 (1) to (xix) towel--------------------------------------- The hard-acting composition of the present invention contains the ascorbic oxide compound (1) of the present invention as a resin component of the present invention, and further contains a hardener (8). Further, a step can contain a oxoxane compound as needed ( A) Other epoxy resins, or / and hardening accelerators other than u. Other epoxy resins are not Loss of the cerium oxygen-sintering compound (4) of the present invention (for example, the property of the cured product when the ruthenium is in the hard-dumped structure) is specifically transparency, heat resistance, light resistance, low modulus of elasticity at low temperatures, and In the range of dipping property, thermal cycle resistance, hard production, etc., it can be used in combination. In other cases, these other epoxy resins i improve the cured property of the curable resin composition. The invention is based on the electrothermal burning 321483 37 201020279 The total amount of %(%) of the oxygen resin component is from 3〇 to 10〇, and the weight is from 20 to 10. According to the use, it is 6〇 to 1〇^Π Π 〇〇 'Can be 8 〇 to (10) wt% better 0 reset %, or 7 〇 to 1 〇 0 wt%, while 1 ' combines the oxirane compound of the present invention (Α) with other rings = 曰 (4) epoxy resin The incision compound of the present invention is preferably from 90% by weight to 30% by weight to 9% by weight. _ The curable resin composition of the present invention, the stone of the present invention (4) Or the ratio of the oxime oxygen-burning compound (Α) of the present invention to the oxygen-reducing resin of the king of the oxy-tree The composition is preferably from about 30 to 90% by weight, more preferably from 4 to 9% by weight, even more preferably from about 90% by weight to about 90% by weight, and more preferably from about 9% to about 5% by weight. More preferably, it is about 5 to 80% by weight. Specific examples of other epoxy resins include, for example, shrinkage of a plurality of compounds, and the amount of glycidyl ether compounds of the squama Functional epoxy resin, aromatic epoxy resin nucleus hydration, alicyclic epoxy resin, heterocyclic epoxy resin, _ oleine epoxy resin, glycidylamine epoxy resin ^Reducing and reducing the resin of the county, the water-hydrogenated 24 oxygen tree ^ The polyphenol compound used in the above polyfunctional epoxy resin can be, for example, bisphenol A, bisphenol F, bisphenol s, 4, 4,- Bisphenol, tetramethyldihydrazyl double A, tetramethyl double F, dimethyl dip F,: A, s, dimethyl bisphenol s, tetramethyl-4, 4, _ bis τ暴〜4,4,-联321483 38 201020279 纷,1-(4-经笨基)|[4_(1,Bus-(4_Phenyl)ethyl)phenyl]propane, 2,2 'Methylene-bis(4_methyl-6- Third butyl phenol), 4, 4, - butylene (3 methyl tert-butyl phenol), tris (hydroxyphenyl) decane, m-benzene - expectant benzene, a neighbor, stupid, There are a variety of diisopropylidene skeletons: hydroxy groups having an anthracene skeleton such as a hydroxy group, and a SHb compound such as a phenolated polybutene. Therefore, as the epoxy resin of the polyglycidyl ether compound of the above-mentioned compound, specifically, the glycidyl ether compound of the above-mentioned compound can be mentioned. The various types of resin to be used in the above-mentioned epoxy resin can be exemplified by various materials which are various raw materials, and various raw materials such as phenol, indophenol, ethylphenol, and butyl. Phenolic resin as a raw material for various phenols of phenols, octylphenols, bisphenol A, bisphenol F, bisphenol s and naphthols; phenolic phenolic resin containing a benzene dimethyl skeleton; containing dicyclopentane A phenolic phenolic resin having an olefin skeleton; a phenol phenol resin containing a biphenyl skeleton; and various phenol resins such as a phenol phenol resin containing an anthracene skeleton. Therefore, specific examples of the polyfunctional epoxy resin of the glycidyl ether compound of various phenol Q aldehyde resins include glycidyl ether compounds of the phenol resins. The nuclear hydride of the aromatic epoxy resin may, for example, be a nuclear hydride of a glycidyl etherate of a varnish resin which is a raw material of a phenol resin as a raw material, and specifically, various kinds thereof (for example, bisphenol A) , glycidyl ether compounds of phenolic compounds such as bisphenol F, bisphenol S, 4, 4'-biphenol, or phenol, cresol, ethyl phenol, butyl phenol, octyl phenol, bisphenol A A nucleated hydrogenated product of a glycidyl ether compound of a phenolic resin as a raw material, such as bisphenol F, bisphenol S, and naphthol. 39 321483 201020279 • The date of the milky month can be exemplified by: 2 p, —androkiylcyclohexyl)propane, 3 4 new A class, and (4 g of glyceryl oxyhydroxide, 4 glycosyl hexane carboxylic acid 3 , 4-epoxy group jf hexyl methacetate, ethylene cyclohexadiene dioxide: 5'5 snail-(3, b-epoxycyclohexylcyclohexyl) hexamethylene diester, etc. Epoxy waxes, and fats which are specifically designed with an aliphatic skeleton, such as 1,4-butanediol, hexanyl hexamethacrylate, an aliphatic epoxy resin such as a glycidyl ether of a polyhydric alcohol, for example, a polycondensation of a polyhydric alcohol such as an alcohol, a polyethylene glycol, a polyhydric alcohol, a tetraol or a benzene dimethanol derivative, etc. The heterocyclic epoxy resin may be, for example, an isocyanuric ring (is〇cy face price nng) : a heterocyclic epoxy resin having a heterocyclic ring such as a _ ring or the like. The glycidyl ester epoxy resin may, for example, be a hexahydrophthalic acid-glycidyl phthalate or tetrahydrophthalic acid. Diglycidyl § An epoxy resin composed of a glycidyl ester of hexagram, etc. The glycidylamine-based epoxy resin may, for example, be an aniline anilide, a private one, or a diamine. A glycidylated epoxy resin such as an amine diphenylmethyl derivative or a diamine methyl streprene derivative. The halogenated phenolic glycidylated epoxy resin can be exemplified by: brominated double A , brominated bisphenol!^, brominated bisphenol s, desertified phenolic phenol, desertified phenolic phenolic acid, chlorinated double S, chlorinated double a, etc. The epoxy resins are not particularly limited in use, and from the viewpoint of transparency, 'the coloring property is preferably small. Generally, the bisphenol A, the double F, the double s, and the 4 are used. 4' - joint age, tetradecyl-4, 4, - joint age, 1 - (4_ 321483 40 201020279 by stupid base)-2-[4-(1,1-bis-(4-hydroxy stupyl) Phenyl]propane, tris(p-phenyl)methane, m-benzoquinone, 2,6-di-t-butyl-p-benzoquinone, having a hetero-propylene skeleton, or 1,1 a polyfunctional epoxy resin having a glycidyl compound of a phenol having an anthracene skeleton; a phenol having a phenol, a cresol, a bisphenol A, a bisphenol S, and a naphthol a phenolic resin as a raw material, containing a dicyclopentadiene skeleton a phenolic phenolic resin, a phenolic phenolic resin containing a biphenyl skeleton, a glycidyl ether compound of various phenolic resins such as a phenolic phenolic resin containing a burial skeleton; bisphenol A, double age F, double squaring, 4'4'-linked a glycidyl ether compound of a phenol compound such as a phenol, or a phenol, a phenolic ethyl group, a butyl group, a octyl group, a bis, a pair, a jr, a bis, and a naphthene. For the frequency of the secret tree (four) glycidylation of the nuclear hydride; 3,, 4, ~ epoxy ring _ 3,4_ epoxy

An alicyclic epoxy resin having a cyclohexane frame such as a cyclohexylmethyl ester; a glycine-containing melamine of H alcohol, polyethylene glycol, or polypropylene glycol; glyceryl isocyanurate or hexahydrophthalic acid It is preferable to reduce the alicyclic epoxy resin which burns the skeleton, such as heat-resistant transparency, light-resistant transparency, and the like. :; Oxygen II has the necessity of cyclohexene, etc., and can be used in combination with two or two kinds of =::, with heat resistant content =: hardener (8) used and hardening accelerator (. = compound, amide compound, _ The compound may be exemplified by, for example, H, phenyl, acenaphthyl, acenaphthyl diphenyl stone, isophora diamine, dicyandiamide sclerosing agent (8), amine group, liver, human a / . Milk, carboxylic acid limited diethylenetetramine 32J483 41 201020279 (dicyandiamide), tetraethylamamine, dimethylbenzamide, ketimine compound, dimer from linolenic acid and ethylenediamine Polyamine resin synthesized; phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, mercapto tetrahydrophthalic anhydride, hydrogenated nadic anhydride, hydrogenation曱 纳 纳 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克 克Stearic acid, tetrahydrophthalic acid, hexahydrophthalic acid, mercapto hexahydrophthalic acid, trimellitic acid, cyclohexane Acid, 1, 2, 3, 4-butane tetracarboxylic acid; bisphenols, phenols (phenols, alkyl-substituted phenols, naphthoquinones, alkyl-substituted naphthols, dihydroxybenzenes, dihydroxynaphthalenes, etc.) a polycondensate of various aldehydes, a polymer of phenols and various diene compounds, a polycondensate of phenols and aromatic dimethylol groups, or a condensate of bis-decyloxy fluorenylbiphenyl with naphthol or phenols And phenols and such modified substances, imidazole, boron trifluoride-amine complex, hydrazine derivative, etc. Among these, moderately usable time when mixed with epoxy resin to form a resin composition (or operation time; Pot Life), and transparency of the cured product, in particular, an acid anhydride compound or a carboxylic acid compound is preferred, and hexahydrophthalic anhydride or methylhexahydroortylene is further used. Diphthalic anhydride, 1,3,4-cyclohexanetricarboxylic acid-3,4-anhydride, deuterated nadic anhydride, hydrogenated methylnadic anhydride are preferred. Relative to the oxirane compound in the composition. The amount of the hardening agent (B) is from about 0.2 to 1.5 equivalents, and the amount of the hardener (B) is from about 0.2 to about 1.5 equivalents. Preferably, it is preferably from about 0.3 to 1.2 equivalents, and particularly, the amount of the hardener used in the case of using a tertiary amine such as benzyldidecylamine as the hardener (B), relative to the composition The ring 42 321483 201020279 is preferably used in an amount of from 0.3 to 20% by weight, particularly preferably from 0.5 to 10% by weight. Examples of the hardening accelerator (C) include 2-mercaptoimidazole and 2-benzene. Imidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-mercaptoimidazole, 1-phenylmercapto-2-phenylimidazole, 1-phenylhydrazino-2 Mercaptoimidazole, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-phenylmethane, 1-cyanoethyl-2-undecylimidazole, 2, 4-diamino-6(2'-mercaptopropi (1,)) ethyl-s-tripa D well, 2,4-diamino-6 (2,-alkyl group 〇 sitting (1 ,)) Ethyl-s-trisyl, 2, 4-diamino-6(2'-ethyl, 4-mercaptoimidazole (1,)) Ethyl-s-three D well, 2, 4 -diamino-6(2,-methylmercapto(1,))ethyl-s-triterpene-isocyanuric acid adduct, 2-mercaptoimidazole isocyanuric acid 2:3 adduct 2-phenylimiphatic isocyanuric acid , 2-phenyl-3, 5-dimethylmethyl salic, 2-phenyl-4-hydroxydecyl-5-methylimidazole, 1-cyanoethyl-2-phenyl-3, 5 - a cyanoethoxymethyl taste ° sitting in various kinds of sodium saliva; and, such imidazoles and phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid a salt of a polycarboxylic acid such as naphthalene dicarboxylic acid, maleic acid or oxalic acid; a guanamine such as dicyandiamide; and 1,8-diaza-bicyclo(5·4.0) eleven-7 Aza compound; and salts of such tetraphenylborate, phenol aldehyde, etc.; salts with the above polycarboxylic acid or phosphonic acid; tetrabutylammonium bromide, cetyl bromide Ammonium salts such as trimethyl ammonium, cetyltrimethylammonium hydroxide, trioctyl decyl ammonium bromide; triphenylphosphine, tris(phenyl)phosphine, tetraphenyl, stinky scale, four a phosphine or a scaly compound such as phenyl fluorene tetraphenyl succinic acid vinegar or methyl tributyl sulphate phosphatide; a phenol such as 2, 4, 6-tris(amino fluorenyl) phenol; an amine adduct . For example: U-CAT 18X (commodity name·· 43 321483 201020279)

San-Apro (share) manufacturing) and so on. The hardening accelerators can be microencapsulated. Which of these hardening accelerators is used can be suitably selected, for example, according to characteristics required for a transparent resin composition which can obtain transparency, curing speed, and working conditions. 0至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至The range of 5 parts by weight is preferably more preferably from 0.05 to 1 part by weight. In the curable resin composition of the present invention, an inorganic filler, a colorant, a polysulfide resin, a leveling agent, a lubricant, a compounding agent, and the like may be appropriately added depending on the purpose, without departing from the scope of transparency and transparency. Leveling agents, lubricants, light stabilizers, antioxidants, and phosphors. The inorganic filler is not particularly limited, and examples thereof include crystalline or amorphous cerium oxide, talc, cerium nitride, boron nitride, aluminum oxide, cerium oxide, and titanium oxide mixed solution. The coloring agent is not particularly limited, and examples thereof include phthalocyanine, azo, disazo, quinacridone, anthracene, flavanone, purple ketone, hydrazine, dioxin, q condensed azo, hydrazine. Azodimethine is a variety of organic pigments, titanium oxide, sulphuric acid boat, chrome yellow, zinc yellow, sputum, iron sulphide, Ming purple, Prussian blue, ultramarine blue, carbon black, chrome green, chromium oxide, cobalt green, etc. Inorganic pigments. The polyoxynoxy resin may, for example, be dimethyl polyfluorene oxide, phenyl fluorenyl polyfluorene oxide, epoxy modified polyfluorene oxide, polyether modified polyfluorene oxide, amine modified polyoxyl oxide, vinyl modified Poly-oxygen, decyl-modified polyoxyl, and the like. The leveling agent may, for example, be an acrylate having a molecular weight of 4000 to 12000 44 321483 201020279 composed of acrylates such as ethyl acrylate, butyl acrylate or 2-ethylhexyl acrylate; epoxidized soybean fatty acid; epoxidation; Rosin alcohol; hydrogenated castor oil; titanium-based compounding agent. Examples of the lubricant include hydrocarbon-based lubricants such as paraffin wax, microcrystalline wax, and polyethylene wax; and higher fatty acid-based lubricants such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid; a high-grade fatty amide-based lubricant such as stearylamine, palm amide, ceramide, sulfhydryl bis-lipidamine or ethyl bis-stearamide; hardened castor oil, butyl stearate, a high-grade oxime fatty acid ester lubricant such as ethylene glycol monostearate or pentaerythritol (mono, di-, tri- or tetra) stearate; cetyl alcohol, stearyl alcohol, polyethylene glycol, polyglycerin, etc. Alcohol-based lubricant; lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, ricinoleic acid, Huanyuan acid, etc., #5, mine, 钡, 辞, lead, etc. Metal soaps of metal salts; natural waxes such as carnauba wax, rehearsal wax, - beeswax, and montan wax (also known as montan wax). The coupling agent may, for example, be 3-glycidoxypropyltrimethoxydecane, 3-glycidoxypropylmercaptodioxane, 3-glycidyloxyqylpropyltrimethoxy decane, 2 -(3,4-epoxycyclohexyl)ethyltrimethoxydecane, N-(2-aminoethyl)3-aminopropylmethyldimethoxydecane, N-(2-aminoethyl 3-aminopropylmethyltrimethoxyoxime, k-aminopropyltriethoxydecane, 3-mercaptopropyltrimethoxydecane, vinyltrimethoxy decane, N-(2- (Vinylbenzamine)ethyl)3-aminopropyltrimethoxy decane hydrochloride, 3-methylpropenyloxypropyltrimethoxy decane, 3-chloropropylmethyldi a decane-based coupling agent such as a decyloxane or a 3-chloropropylmethyltrimethoxy decane; (N-ethylaminoethylamino) isopropyl titanate or a triisostearate titanate Propyl ester, bis(dioctylpyranosyl)oxyacetic acid 45 321483 201020279 Titanium, tetraisopropylbis(dioctylphosphite)carboxylate, neosodium oxylate (PN-(no-amine) Titanium-based coupling agent such as ethyl ethyl)aminophenyl) titanate; Hammer, bismuth methacrylate, zirconium propionate, neoalkoxy zirconate, neoalkoxytrimethylene phthalate, neoalkoxytris(taudecyl)benzenesulfonate zirconate, Neoalkoxytris(ethylenediamineethyl)phthalate, neoalkoxytris(m-aminophenyl)zirconate, ammonium carbonate, acetoacetate, mercapto acrylate chain, aluminum propionate A zirconium or aluminum based coupling agent. The light stabilizer is a hindered amine-based light stabilizer (11 illusion is suitable. Hals is not particularly limited, but may be exemplified by: dibutylamine. Sanken. N, N_ q double (2, 2, 6, 6 - tetrakisyl-4-pin. succinyl)-1,6-hexanediamine and N-(2' 2,6' 6-tetradecyl-4-piperidyl)butylamine polycondensate, succinic acid II Methyl-1-(2-hydroxyethyl)- 4-hydroxy-2, 2, 6, 6-tetramethylpiperidine polycondensate, poly[{6-(1'1,3,3-tetradecyl) Butyl)amino-H5-tris- 2,4-diyl H(2,2,6,6-tetramethyl-4-piperidinyl)imido}hexamethylene {{2,2' 6,6-tetramethyl-4-piperidinyl)imidopyrene], bis(1,2,2,6,6-pentamethyl-4-piperidinyl)[[3, 5_double (1) , 丨-dimethylethyl)_4_hydroxyphenyl]methyl]butylmalonic acid vinegar, bis(2,2,6,6-tetramethyl_4_Brigade bite) © 夭 酉曰, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2' 2,6,6-tetramethyl-4-piperidyl Pyridyl) sebacate, 2_(3, 5_(^^^^-pentamethyl-indenyl-piperidinyl) or two or more types. Di-tert-butyl-4-hydroxybenzyl) _2_n-butylmalonic acid double ° For the HALS, only one type of sulfur-based or phosphorus-based antioxidant may be used. For example, the 2,6-di-tert-butyl-antioxidant may be exemplified by a specific example of a phenol-based or sulfur-based phenol-based antioxidant. For example, 321483 46 201020279 p-nonylphenol, butylated hydroxyanisole, 2,6-di-t-butyl-p-ethylphenol, stearyl-cold-(3, 5-di-tert-butyl-4- Hydroxyphenyl)propionate, isooctyl-3-(3,5-di-t-butyl-4-phenylphenyl)propanoic acid, 2,4-bis-(n-octylthio) -6-(4-carbazhen-3,5-di-t-butylanilino)-1,3,5-three-pill, 2,4-bis[(octylthio)methyl]o-cresol, etc. Monophenols; 2,2'-methylenebis(4-mercapto-6-tert-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol ), 4, 4'-thiobis(3-methyl-6-tert-butylphenol), 4,4-butylenebis(3-methyl-6-tert-butylhydrazine), triethylene glycol - bis-[3-(3-t-butyl-5-methyl-4-phenylphenyl)propanoate], 1,6-hexanediol-bis[3-(3, 5-di Third butyl-4-hydroxyphenyl)propionate], hydrazine, Ν'-hexamethylene bis (3, 5-di-t-butyl-4-hydroxy hydrogenated cinnamyl) Indoleamine, 2, 2'-thio-di-extended ethyl bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-third 4-hydroxybenzyl-phosphonate-diethyl ester, 3,9-bis[1,1-dimethyl-2-{stone-(3-tert-butyl-4-hydroxy-5-one Tolyl)propenyloxy}ethyl]2, 4, 8, 10-tetraoxaspiro[5,5]undecane, bis(3,5-di-t-butyl-4-hydroxybenzoate a double-seeking class of ethyl sulfonate, calcium, etc.; 1,1,3-tris(2-methyl-4-hydroxy-5th-butylphenyl)butane, 1,3,5-dimethyl- 2, 4, 6-bis(3, 5-di-t-butyl-4-o-benzyl) benzene, tetra-[methylene-3-(3',5'-di-t-butyl- 4,-Hydroxyphenyl)propionate]methane, bis[3,3,-bis-(4,-hydroxy-3,-tert-butylphenyl)butyrate]diol, tris-(3, 5-di-tert-butyl-4-carbylmethyl)-isocyanurate, 1,3,5-tris(3,5'-di-t-butyl-4,-hydroxyphenylhydrazino )-S-tripa-2, 4, 6-(1Η, 3Η, 5Η) triketones, tea phenols and other polymer types. 321483 47 201020279 Specific examples of sulfur-based antioxidants are: 3,3'-thiodipropionic acid dilaurin vinegar, 3,3'-thiodipropionate dimyristyl ester, 3,3'-thiodi Distearyl benzoate and the like. Specific examples of squama antioxidants are: trisuccinyl phosphite, dipyridyl isodecyl phosphite, phenyl diisononyl phosphite, tris(nonylphenyl) amide vinegar, two Isodecyl pentaerythritol phosphite, tris(2,4-di-t-butylphenyl)phosphite, cyclopentanetetraylbis(octadecyl)phosphite, cyclopentane tetrakisyl double (2,4-di-t-butylphenyl)phosphite, cyclopentanetetrakis(2,4-di-t-butyl-4-decylphenyl)phosphite, double [2_ a phosphite such as dibutyl-6-methyl-4-{2-(octadecyloxycarbonyl)ethylphosphonium phenyl]hydrogen phosphite; 9,1 〇_dihydro_9_oxygen Hetero-1 〇 phosphinophen-10-oxide, 1 〇-(3, 5-di-tert-butyl-4-hydroxylmethyl)_9, 1〇_monohydro-9-oxa-ίο-phosphine An oxaphosphonium phenanthrene oxide such as phenanthrene oxide, fluorene phenanthrene oxide, or the like. These antioxidants may be used alone or in combination of two or more. Special wealth is good (4), antioxidants are better. The amount of the antioxidant to be used is usually from 0 to J by weight, based on the weight of the resin component (10) by weight of the curable resin composition of the present invention, preferably from 〇1 to 〇. 5 parts by weight. When the curable resin composition of the present invention is used in an optical semiconductor encapsulant, a phosphor can be added as needed. The fluorescent system emits white light by the vehicle, for example, by the blue light emitted by the element of the == color (4). After the fluorescent _ is scattered on the hardened (four) ribs, the light is sealed. Further, 321483 48 201020279 A conventionally known phosphor can be used, and examples thereof include a rare earth elemental aluminate, a thiogallate, and a protoporate. Specifically, for example, a phosphor such as a YAG phosphor, a TAG phosphor, an orthosilicate phosphor, a thiogallate phosphor, a sulfide phosphor, or the like can be cited, for example. ΑΑ1〇3 : Ce ^ YsAhO, : Ce ^ Y4Ah〇9 : Ce ^ Y2〇2S : Eu &gt; Sr5(P〇4)3ci : ❿

Eu, (SrEU) 〇 · Al2 〇 3 and the like. The particle size of Yanhai Camp can be used in the field, and the average particle size is 1 to 250 _, preferably 2 to 5 () _. When the phosphors are used, the amount thereof is from 1 to 80 parts by weight, preferably from 5 to 60 parts by weight, based on 1 part by weight of the resin component. &quot;^ The preferred curable resin composition of the present invention is as follows. (I) A curable resin composition containing the reactive functional group-containing oxirane compound (hereinafter referred to as the oxime compound of the present invention (A) Or the oxoxane compound (A)) and an epoxy compound other than the oxirane compound (A) (hereinafter also referred to as G~B: P〇), the total amount of which is relative to the composition The total weight is from 3 to 9 inches from the following unless otherwise limited, and the remainder is the hardener (B). (II) The curable resin composition according to the above (丨), wherein the range of the hardening fastness (B) is 〇·2 with respect to 1 equivalent of the epoxy group of the austenite compound (A) Up to 1.5 equivalents. (11) The curable resin composition according to the above (I) or (II), wherein the total amount of the oxirane compound (A) and the arbitrarily contained 0-ΕΡ0 relative to the entire composition is (C) The curable resin composition according to any one of the above (I) to (III), wherein the oxime compound (A) and optionally 〇EP〇321483 are contained. The total amount of the siloxane compound (A) is from 50 to 1% by weight. (V) The curable resin composition as described in any one of the above (1) to (IV), in the pot, relative to The total amount of the oxoxane compound (A) and the hydrazine-Ep〇' which may be optionally contained, the ratio of the oxoxane compound (A) is from 3 〇 to 9 〇 %. (VI) as in the above (1) to (7) A hardening resin composition according to the above, wherein the pottery contains a hardening accelerator in a ratio of n to 15 parts by weight based on 10 parts by weight of the azide compound (A). (VII) as described above ( I) to (a hardening resin composition described in any one of VD), wherein the curing agent (B) is an acid anhydride compound or a citric acid compound. The resin composition is obtained by uniformly mixing the above-mentioned raw materials by any method. ^ The above-mentioned curable resin composition of the present invention contains a reactive oxygen-containing compound (A) and a hardener (B) And any other compounding component which can be adjusted in the curable resin composition in accordance with the hardening-promoting (C) agent required. Other optional ingredients may be, for example, inorganic fillers and colorants. , polyoxyl resin, leveling agent, lubricant, consumable, light stabilizer, antioxidant, phosphor, etc. These other compounding ingredients 'relative to the alkoxylate compound (A) and hardener (B) The total amount of 100 parts by weight may be suitably added in the range of 0 to 500 parts by weight, preferably from 0 to 100 parts by weight. When these other ingredients are formulated, the Henschel mixer is used in the solid state. After mixing with a mixer such as a conical mixer (Nautamixer), the kneader, the extruder, and the heating roller are kneaded at 80 to 12 (TC) and cooled, and the house is pulverized to obtain a powder. On the one hand, when the blender is in a liquid state, 50 321483 201020279 is uniformly dispersed by using a planetary mixer or the like, and the curable resin composition of the present invention having 3 other fine &amp; components may be obtained. With the composition of the present invention thus obtained, when the optical semiconductor of the present invention is sealed by the optical semiconductor of the LED, the photoreceptor, the transceiver, etc., it can be converted into (10) (10) compression molding. ^A^^(injecti〇nm〇ld.ng) ^ 成形Forming by conventional molding methods such as disPensing method and printing method. In the heating method for curing the resin composition for sealing a photo-semiconductor, it is not particularly limited, and a hot-air circulation type heating, infrared heating, or (four) scaling method can be employed. The hardening conditions are generally about = to 3 minutes to 15 hours after the fiber is heated, but the conditions can be appropriately changed. The preferred condition is (10) to the job, preferably for example. First, push 100~14〇°c down to Α, onn〇r. ^ L under 仃 hardening, then final hardening at 13〇 to 200 C The method. Hereinafter, the present invention will be described in more detail by way of Synthesis Examples and Examples. Meanwhile, the present invention is not limited to the above-described synthesis examples and examples. Further, each physical property value in the examples was measured by the following method. (1) Molecular weight: Various conditions of polystyrene-equivalent weight GPC determined by the following conditions by the GPC method. J. 卞罝 薇 薇 : :: Shimadzu Corporation column: protection column SHQDEX GPC LF ~G Lf__ Flow rate: 1· Oml/min· 321483 51 201020279 Column temperature: 40°C Solvent: THF (tetrahydrofuran) Detector: RI (differential refractive detector) (2) Epoxy equivalent: according to JIS The method described in K-7236 was measured. (3) Viscosity: measured at 25 ° C using an E-type viscometer (TV-20) manufactured by Toki Sangyo Co., Ltd. [Examples] Hereinafter, the present invention will be described in more detail by way of Synthesis Examples and Examples. Meanwhile, the "parts" and "%" in the synthesis examples and the examples are "parts by weight" and "% by weight", respectively. Further, although the alkoxy equivalent and the decyl alcohol equivalent are not described, the units are all g/eq. Example 1 (Example of reacting 1 equivalent of decyloxy group with respect to a ground alcohol group to a ratio of 5.3 equivalents) Stage 1 reaction: /3-(3,4-epoxycyclohexyl)ethyl three 1 part (alkoxy equivalent: 82. lg / eq), weight average molecular weight 10 6 0 (GPC measured value) of sterol terminal dimercapto polyoxyl oil 2 3 7.4 parts (sterol) Equivalent 530 g/eq), 0.5% potassium hydroxide (Κ0Η) methanol solution 21. 3 parts (Κ0Η parts of 0.11 parts) were charged into the reaction vessel, and the liquid temperature was raised to 75 °C. After the temperature was raised, the reaction was carried out at 75 ° C for 8 hours under reflux. The sterol equivalent of 53 Og/eq is the weight average molecular weight of 1060 as measured by GPC as the molecular weight of the polyoxo oxy-oil, and since it has two linoleic groups per molecule, half of the value is calculated. In the following examples, the decyl alcohol equivalent of the decyl alcohol-terminated polyoxyl oil (b) was also determined in the same manner. 52 321483 201020279 The second reaction was carried out by adding decyl alcohol 305 to the reaction liquid obtained above, and then injecting 5 〇% of the steaming water and boiling liquid 86. 4 parts in 60 minutes, and reacting at 75 C for 8 hours under a machine. After the completion of the reaction, the reaction liquid was neutralized with a plant acid-sodium sulphate aqueous solution, and methanol was recovered under steaming. After adding methyl isobutyl hydrazine (M serving) to the remaining reaction solution, it is then added to ❹ ❹. Two = A water wash. Next, the organic phase was separated, and then, under reduced pressure, a solvent of 100 was used to obtain 344 parts of a compound (h) having a reactive functional group. The obtained compound had an epoxy equivalent of Μ ^ red 14. The average molecular weight was 3,700, and the viscosity was 600 mPa·s. The appearance was colorless and transparent. The proportion of the stone atomic atoms belonging to the sesquiterpene gas-burning chain segment (relative to all the stone cherries) was calculated to be 19.6 mol% from the (four) sub-combination of the three oxygen atoms calculated by the feed material ratio. Similarly, the proportion of the bond-like polyoxo bond segment was 80.4 mol%. Dependent Example 2 (Example of a reaction in which the relative oxo group 找t is oxidized to 3 ().8 equivalents) The first stage reaction: cold-(3,4-epoxycyclohexyl) Ethyldimethoxydecane 197.1 parts (alkoxy equivalent 82 丨), weight average molecular weight of one A (GPC measured value) of sterol terminal dimercaptopolyoxyl oil 237.4 parts = amount 3060), 0. 5% Κ 0 Η methanol solution 20.0 parts (Κ0 Η parts: j alcohol was charged into the reaction vessel, and the liquid temperature was raised to 75 ° C. After heating, known), the reaction was carried out at 75 ° C for 8 hours. In the reflux phase 2 reaction: after adding 260 parts of methanol, the person was dripped in 32,148,53, and 201020279, 50°. 8 parts of methanol solution was taken at reflux for π hours. And ^ 廉 4士 jk &gt; 〇 〇 ^, after neutralization with 5% aqueous sodium dihydrogen phosphate solution, alcohol. Add M service (10) parts, repeat 3 times twice 'The organic phase is removed under reduced pressure, 100 ° C, and the solvent is obtained by the reactive official Saji Mountain Xuan Lu / Heyi. The block type siloxane compound (A-2) is 36 parts by weight. In 4160, the viscous &amp;% sufficiency is 468 &amp; /, the weight average molecular weight is pendulum, the viscosity is 48 lmp 卞垔 is a halved money smear, and the bond poly (tetra) diatomic ratio is 19.6 Moer%. In the same manner as in Example 3, the # atom_ is 8 G.4 mol%. (Example of the reaction with respect to the oxime-based oxime equivalent) The soil is made into a ratio of 80. 1 equivalent. The first-stage reaction: 厶~. a oxy-stone smoldering 98.6 parts (burning oxygen equivalent hexyl) ethyl trimethyl (GPW fixed value) of the end of the sulphate end = = weight average molecular weight 15 _ 790 〇), 05% K 〇 H methanol soil poly-stone oxygen 'by 118.7 parts (Shixi alcohol 酤 λ = liquid 10. 〇 part (KOH part i Λ field into the reaction vessel 'to make the liquid temperature rise = 〇 · 05 parts) to react at 75 8 for 8 hours. The second-stage reaction under reflux: after adding 142 parts of methanol, 4〇% of the steaming and water sterol solution was 43. 2 parts, and it was made to reflux: the fin was dripped for 8 hours. After the reaction, 'μ, acid dihydrogen sodium The water-soluble C reaction was carried out at 8 ° C to recover the sterol. Adding 9 parts of curry: and then 'washing with water. Then the organic phase was removed under the reduction, just c. Repeat 3: owed to the reactive functional group Inlaid "Wei (four), from this, U, 69. 321483 201020279 The obtained compound has an epoxy equivalent of 4130, a viscosity of 710 mPa · : ^ eq, and the weight average molecular weight is nucleus transparent and colorless and transparent. The ratio of the segment of the segment is 19 6 and the sample is 'chain-like poly-chain segment a 4 the ear is the same as the embodiment 4 atomic ratio is 80_4 mol%. In the case of the decyl alcohol equivalent, the base should be 8.6 equivalents of the ruthenium-based n(3,4'epoxycyclohexyl)ethyltrimethyl sulphide 49.3 parts (burning oxygen equivalent 82i parts (alkane) Oxygen equivalent 66 1), Tongue 曰 | 丞矽 丞矽 卯 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 κ κ κ κ 乂 乂 乂 乂 乂 乂 乂 乂 乂 118 118 118 118 118 118 118 118 118 118 118 118 118 118 Κ0ΗMethanol dissolved (four).. (The number of coffee is: the reaction container is raised to between 75 μL and 75 °; and the temperature is raised, and the reaction is carried out at 75 ° C for 8 hours under reflux. The second stage reaction: adding 123 parts of sterol After that, 43 parts of ❹50% steamed crane water methanol solution was added dropwise in 60 minutes, and it was reacted under reflux for 8 J under reflux. After the reaction was finished, 'after neutralization with 5% aqueous solution of dihydrogen phosphate, after t: The methanol was distilled off, and 191 parts of ΜΙβκ was added, and the water was washed three times. Then, the organic phase was removed under reduced pressure of 1 Torr to obtain a block type oxalate compound having a reactive functional group. (A-4) i 6 8 parts. The epoxy equivalent of the compound was 874 g/eq, the weight average molecular weight was 2630, and the viscosity was 4600 mPa · s. 5摩尔的。 321483 55 The ratio of the atomic atoms belonging to the chain polyoxynoxy group is 77. 5 mol%. 321483 55 2010份。 Example 5 (assuming that the equivalent of alkoxy groups relative to the oxime oxime) is 8.6 equivalents of the anti-different phase 1 reaction oxoxane 49. 3 parts (alkoxy equivalent 82. 丨 ^ oxy % hexyl) ethyl trimethyl ester (alkoxy equivalent: 45.4), weight 岣 岣 甲基 甲基 27 27 27 27. 2 矽 末端 末端 end methyl phenyl phthalate 118 17 〇〇 (GPC measured value) Then, 10.0 parts of the oxime solution (the K 〇 H fraction is known as sterol equivalent 850) and 0.5%, and the liquid temperature was raised to 75 °C. l, ^ 〇 〇 5 know) loaded into the reaction vessel for hours. Reaction at 75 ° C under reflux 8 Phase 2 reaction: additional methanol 50% distilled water methanol solution 43. 2 parts: after 'drip in 8 minutes. After the reaction is over, take 5 . Nasal acid flows down in the muscles and reacts with methanol to recover methanol. After adding MIBK: neutralized aqueous solution, it was washed with water. Next, the organic phase is subjected to a reduced pressure, 1 〇 I, and repeated 3 times == functional group money type money ~ _ parts. The epoxy equivalent of 5850^ is coffee (10), the weight average molecular weight is 461〇mPa.s, and the appearance is colorless and transparent. _ ^ The ratio of the stone atom of the semi-stone compound is 20.0%. In the same way, the W sub-group belonging to the chain (four) oxygen chain segment is the movable Mole %. Example 1 (Comparative to the ratio of the base 1# to the amount of the base 4# to the amount of the substrate), which is the result of gelation in the first stage reaction, and cold (3'4-% oxy group) Cyclohexyl)ethyltrimethoxydecane 37 〇 part 321483 56 201020279 (burning oxygen equivalent 82.1), 畲 芈 芈 secret, ^

Alcohol terminal dimethyl polyphosphonium 17 ^ knife I 1 〇 6 〇 (GPC measured value) 矽 methanol, liquid solution 7 〇. 9 parts (sterol equivalent 530), 0.5% KOH = ϊ 7 parts of coffee for. .06 parts) was charged into the reaction vessel, and after the dish was raised by two to 75 〇rw, the reactant was reacted at 75 ° C for 4 hours under L. Reference Example 1 was a gelling agent ( A-6). ❹ if the phase of the alcohol group 1 when the neooxyl is 5 to 5 equivalents and in the case of the reaction of water in the case) (burning oxygen / amount Ϊ ^ epoxy fluorenyl) ethyl trimethoxy sulphur (10)· 6 parts of mouth--, weight average molecular weight l〇60 (GPC measured value) of sterol-terminated dimercapto-polyoxyl oil 118.7 parts (incineration of 53 〇), methanol i3i parts, 0.5% Κ0Η曱The alcohol solution 10·0 parts (10) parts (10) parts were shaken into the reaction vessel to raise the liquid temperature to 75 Torr. After the temperature was raised, 43.2 parts of a 50 M aqueous methanol solution was added dropwise thereto over 6 minutes, and it was allowed to react under reflux for 8 hours under π. After completion of the reaction, the mixture was neutralized with a 5% aqueous sodium dihydrogen phosphate solution, and then methanol was distilled off at 80 °C. 191 parts of MIBK were added and washed three times. Next, the organic phase was subjected to a solvent under reduced pressure at 1 Torr to obtain 176 parts of a oxoxane compound (A-7) having a reactive functional group. The obtained compound had an epoxy equivalent of 459 g/eq and a weight average molecular weight of 33 Å, and the appearance was white turbidity and could not be used as a composition for an optical semiconductor sealing material. Reference Example 2 (Example in which 1 equivalent of alkoxy group relative to a sterol group is 3 〇. 7 equivalents and reacted in the presence of water) 321483 57 201020279 The same operation as the synthesis method of Patent Document 1, /5- (3, 4-Ethoxycyclohexyl)ethyltrimethoxy decane 45.4 parts (alkoxy equivalent weight 82.1), weight average molecular weight 6120 CGPC measured value) sterol terminal dimercapto polyoxyl sulfonate 54. 6 Parts (sterol equivalent 3060), triethylamine 10.0 parts, MIBK 500 parts were placed in a reaction vessel, stirred at room temperature, and 100 parts of distilled water was added dropwise over 30 minutes, and the temperature was raised to 80 ° C to react. 6 hours. After completion of the reaction, the mixture was neutralized with a 20% aqueous solution of dihydrogen chloride, and washed with water three times. Then, the organic phase was removed under reduced pressure at 10 ° C to obtain 85 parts of a white turbid liquid (A-8), which was not used as a composition for an optical semiconductor sealing material. © Reference Example 3 (Example of making 1 equivalent of alkoxy group relative to sterol group to 31.0 equivalents and reacting in the presence of water) /3-(3,4-Ethoxycyclohexyl)ethyl 7 parts of tridecyloxydecane (alkoxy equivalent: 82.1), weight average molecular weight 6120 (GPC measured value) of sterol terminal dimethyl polyfluorene oxide 94.0 parts (sterol equivalent 3060), methanol 104 parts 0. 5% KOH methanol solution 8. 0 parts (KOH part is 0.04 parts) was placed in the reaction container to raise the liquid temperature to 75 °C. After the temperature was raised, 34.6 parts of a 50% distilled water sterol solution was added dropwise thereto over 60 minutes, and the mixture was reacted at 75 ° C for 8 hours under reflux. After completion of the reaction, the mixture was neutralized with a 5% aqueous sodium dihydrogen phosphate solution, and then decyl alcohol was distilled at 80 °C. 152 parts of MIBK were added and washed three times. Then, the organic phase was removed under reduced pressure at 10 ° C to obtain 151 parts of a white turbid liquid (A-9), which was not used as a composition for an optical semiconductor sealing material. Reference Example 4 58 321483 201020279 (Example in which 1 equivalent of alkoxy group relative to a sterol group is made to a ratio of 80. 0 equivalent and reacted in the presence of water) 5-(3,4-epoxycyclohexyl) 7份(矽醇当量7900), methanol, ethyl methoxy methoxy decane 98. 6 parts (alkoxy equivalents 82.1), weight average molecular weight 15800 CGPC 'determination value) sterol terminal dimethyl polyfluorene oxide 118. 7 parts (sterol equivalent 7900), methanol 142 parts, 0.5% sterol solution 10.0 parts (parts of 0.05 parts) were charged into the reaction vessel to raise the temperature to 75 °C. After the temperature was raised, 43.2 parts of a 50% distilled water methanol solution was added dropwise thereto at 60 minutes, and the mixture was reacted at 75 ° C for 8 hours under reflux. After completion of the reaction, the mixture was neutralized with a 5% aqueous solution of sodium diphosphate phosphate, and then methanol was distilled off at 80 °C. 191 parts of MIBK were added and washed three times. Then, the organic phase was removed under reduced pressure at 100 ° C to obtain 189 parts of a white turbid liquid (A-10). Comparative Example 2 A polyoxyphthalic acid ester having an alkoxy group represented by the following formula (5) was used instead of the decyl alcohol-terminated polyoxyxene oil of the formula (2) used in Examples 1 to 5 to carry out the synthesis. H3C-0-4—Si—0—j—CH3 (5) ^ ch3 /m 10,000-(3,4-epoxycyclohexyl)ethyltrimethoxy decane 37.0 parts (alkoxy equivalent 82 5% KOH溶液溶液 5. 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 The fraction (0.0 parts by weight of KOH) was placed in a reaction vessel to raise the temperature of the liquid to 75 °C. After the temperature was raised, 16.2 parts of a 50% aqueous methanol solution was added dropwise thereto at 60 minutes, 59 321483, 201020279, and allowed to react at 75 ° C for 8 hours under reflux. After completion of the reaction, the mixture was neutralized with a 5% aqueous sodium dihydrogen phosphate solution, and then methanol was distilled off at 80 °C. 88 parts of MIBK were added and washed three times with repeated washing. Then, the organic phase was removed under reduced pressure at 100 ° C to obtain a white turbid liquid (A-11) of 80.6 parts, which was not used as a composition for an optical semiconductor sealing material. The properties of the resins A-1 to A-Π obtained in Examples 1 to 5, Comparative Examples 1 and 2, and Reference Examples 1 to 4 are summarized in Table 1. Table 1 Compound Addition Equivalent Value (Alkoxy/Calcitol Group) Example 1 A-1 5.3 Example 2 A-2 30.8 Example 3 A-3 80.1 Example 4 A-4 8.6 Example 5 A-5 8.6 Comparative Example 1 A-6 1.4 Reference Example 1 A-7 5.5 Reference Example 2 A-8 30.7 Reference Example 3 A-9 31.0 Reference Example 4 A-10 80.0 Comparative Example 2 A-11 — Epoxy Equivalent Molecular Weight Property 457 3700 Colorless transparent liquid 468 4160 Colorless transparent liquid 447 4130 Colorless transparent liquid 874 2630 Colorless transparent liquid 832 5830 Colorless transparent liquid - gelled - white turbid liquid - white turbid liquid - white turbid liquid - white turbid liquid - white turbid liquid by the above As a result, it was confirmed that Comparative Example 1 in which the alkoxy/sterol group of the compound represented by the formula (1) and the alkoxy group/sterol group of the compound represented by the formula (2) were fed was made into a solvent-insoluble gel. Cannot be used as an epoxy resin. Further, Reference Example 1, Reference Example 2, Reference Example 3, and Reference Example 4 (A-7, A) in which a compound represented by the formula (1) and a compound represented by the formula (2) are added with a base catalyst and water at a time. -8, A-9, A-10) become a turbid liquid, can be confirmed and 60 321483 201020279 is not suitable for optical use. Further, A-ll (Comparative Example 2) in which the compound represented by the formula (2) is substituted with the compound of the formula (2) having the oxygenated gas of the compound (2) at the end is also a white turbid liquid. , 矣] is not suitable for optical use. On the other hand, the general formula (1, 3, Α-1, Α-2, Α~3) of the general formula (υ, the general formula (2) = the two-stage reaction of the second step 2) The compounds shown in (2) and (3) can be obtained as colorless and transparent resins by using the two-stage reaction of Examples 4 and 5 (A_4, A-5). Comparative Example 3 ❹ ❹ When the sulphur is calcined in the early structure, the dimethyl dioxane which uses the following formula (6) is used as a raw material 'and the content concentration of the dimethyl methoxy siloxane unit structure contained in the compound ( Mohr was synthesized at the same concentration (mol%) as in the above Examples 1 to 3. ch3 (6) H3C-0-Si-O-CH-s CH, and the synthesis system was the same as the method described in Patent Document i. Operation, '=epoxycyclohexyl)ethyltrimethoxy zebra burned 33.9 parts (burning oxygen equivalent =•1), dimethyldimethoxy-we (throwing oxygen equivalent), ^^face 5〇 0 parts were put into the reaction vessel and stirred at room temperature. The mixture was added dropwise for 30 minutes, and the temperature was raised to 8 (the reaction was allowed to proceed for 6 hours after rc. Reaction, . . , after the bundle, covered with 20% aqueous sodium dihydrogen phosphate solution 3 times of washing. Then will The machine phase is under reduced pressure, (10) the money-burning compound having a reactive functional group ("2):= 321483 61 201020279 has a % oxygen equivalent of 459 g/eq, a weight average molecular weight of 940, and is colorless and transparent in appearance. Example 6 ( An example of reacting with an equivalent of an alkoxy group in an equivalent ratio of alkoxyl group to 3.8 equivalents) ^1st stage reaction: ruthenium-(3,4-epoxycyclohexyl)ethyltrimethoxy 8份(矽醇为置356), burned 147. 8 parts (burning gas equivalent 82. 丨), weight average molecular weight 1060 &lt; ^ PC measured value) 0· 5% Κ0Η MeOH solution 2 〇. 〇 (K 〇H part is 〇. 1 part) into the reaction bar, the liquid temperature is raised to 75. After heating, under reflux at 75 ° C The reaction was carried out for 8 hours. In the second-stage reaction, 255 parts of methanol was added, and then 50/min was added dropwise in (9) minutes. 64 parts of the methanol solution of the cold-distilled water was allowed to react under reflux for 75 hours in 75. After the reaction was completed. After neutralizing with 5% aqueous solution of sodium dihydrogen phosphate, it was recovered at 8 〇. (: The oxime was recovered by steaming the crane. 352 parts of ΜΙβΚ was added, and the washing was repeated three times. Then the organic phase was reduced. Pressing, 1 〇〇. The solvent is removed under the crucible, whereby the block type oxalate compound (a-13) having a reactive functional group is 333 parts by weight. The obtained compound has an epoxy equivalent of 578 g/eq, and the weight average The molecular denier is 5250, the viscosity is 257mPa.s, and the appearance is colorless and transparent. The ratio of the material in the octave (four) oxygen lag is (149) 149 mol%. The sample is the proportion of the stone atom of the chain polystone.冋Comparative Example 4, 咔%. When considering the structure of dimethyl oxalate as a unit, the dimethyl dimethyl oxime of formula (6) is used as a raw material and the compound contains 2 4 321483 62 201020279 The content of the methyloxane unit structure (% by mole) became the same concentration as that of the above Example 6 (the synthesis was carried out by Mo Yan.

The synthesis system is operated in the same manner as in the method described in Patent Document 1, 2. 6 parts (alkoxy equivalent ❹ 82.1), dimethyl 2 7 parts of methoxydecane (alkoxy equivalent of 60.1), 10.0 parts of triethylamine, and 500 parts of MIBK were poured into a reaction vessel, and stirred at room temperature, and 1 part of distilled water was added dropwise thereto for 30 minutes. The temperature was raised to 8 ° C and the reaction was allowed to proceed for 6 hours. After completion of the reaction, the mixture was neutralized with a 20% aqueous solution of sodium hydrogencarbonate, and washed with water three times. The organic phase is then depressurized and enthalpy (10). The solvent was removed under c to obtain 6 parts of a oxoxane compound (A-14) having a reactive functional group. The obtained compound had an epoxy equivalent of 561 g/eq and a weight average molecular weight of 830 Å. The appearance was colorless and transparent. Example 7 (Example of relative to the base of the alcoholic group 1) Although the amount of the alkoxy group is 4.8 equivalents and the reaction of the first stage reaction: oxydecane 59. 1 part will be a point - (3, 4- Epoxycyclohexyl)ethyltrimethyl (GPC measurement), alcohol equivalent 850), 0.5% κ〇η charged into the reaction vessel, 1 part (alkoxy equivalent 82. υ, weight average molecular weight 1 = sterol end Methyl phenyl polyfluorene oxide W 5% Κ〇Η 辟 , ........... 〇 ( 石 石 石 石 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( 13 M parts of phenyloxyl oil (methanol solution 10. 〇 parts (the KOH fraction is 〇 methanol solution 10. 〇份 (the KOH fraction is 〇中', the liquid temperature is raised to 75 ° °. After heating up, 483 63 201020279 Reaction at 75 ° C for 8 hours. Stage 2 reaction: After adding 135 parts of decyl alcohol, 25.9 parts of 50% distilled water methanol solution was added dropwise over 60 minutes, and it was reacted under reflux at 75 ° C. After the completion of the reaction, the mixture was neutralized with a 5% aqueous sodium dihydrogen phosphate solution, and then decyl alcohol was distilled off at 80 ° C. Thereafter, 170 parts of MIBK was added for washing, and water washing was repeated three times. Under decompression The solvent was removed at 100 ° C, thereby obtaining 162 parts of a block type oxoxane compound (A-15) having a reactive functional group. The obtained compound had an epoxy equivalent of 707 g/eq, a weight average molecular weight of 2680, and a viscosity. The appearance was 727 mPa · s, and the appearance was colorless 透明 transparent. The proportion of ruthenium atoms belonging to the sesquioxane chain segment was 13.6 mol%. Similarly, the proportion of ruthenium atoms belonging to the chain polyoxynene segment was 86.4 mol%. Examples 8 to 13 and Comparative Examples 5 to 7 Commercially available alicyclic rings for use in the above-described synthesized oxoxane compounds (any of A-1 to 3, 12 to 15) or conventional optical semiconductors. Oxygen resin (ERL-4221), hardener (B-1 to B-3) or hardener (B-3) and ^ hardening accelerator C-1, as shown in Table 2, 3, 4 or 5 The mixture was mixed to obtain the compositions of Examples 8 to 13 and Comparative Examples 5 to 7. The examples and comparative examples described in Table 2 are as follows. Example 8: Using Compound A-1 and Hardener B Composition of -1 Example 9: Composition using Compound A-2 and Hardener B-1 Example 10: Composition using Compound A-3 and Hardener B-1 Comparative Example 5: Composition using Compound A-12 and Hardener B-1 64 321483 201020279 Comparative Example 6: Composition using ERL-4221 and hardened 彳Β-l Example and Comparative Example described in Table 3 The following are the following. Example 11: Composition using Compound A-13, Hardener B-3, and hardening promoting residual C-1 Comparative Example 7: Using Compound A-14, Hardener B-3, and Hardening Accelerator C- The composition and the comparative examples described in Table 4 of the composition are as follows. Example 12: Use of Compound A-15, Hardener B-3, and Curing accelerator 组成 Composition of C-1 The examples and comparative examples described in Table 5 are as follows. Example 13: Composition using Compound A-13, Hardener B-3, and Hardening Accelerator C-1 Comparative Example 6: Composition using ERL-4221 and Hardener B-1 For Examples 8 to 13, The curable resin composition obtained in Example 5 was subjected to the following transmittance test, mechanical property test (dynamic viscoelasticity test), and LED illumination test, and the results are shown in Tables 2, 3, 4, and 5. (UV Durability Transmittance Test) The curable resin compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to vacuum defoaming for 20 minutes, and then gently poured into an aluminum foil cup having a bottom surface diameter of 5 cm and a height of 2 cm. Casting in. The cast product was placed in an oven under predetermined hardening conditions to be hardened to obtain a test piece for penetration of 2 mm in thickness. Using these test pieces, the transmittance (measuring wavelength: 375 nm, 400 nm, 465 nm) before and after ultraviolet irradiation was measured by a spectrophotometer, and the rate of change was calculated. The ultraviolet irradiation conditions are as follows. 65 321483 201020279 UV irradiation machine: EYE SUPER UV TESTER SUV-Wll Temperature: 60°c Irradiation energy: 65mW/cm2 Irradiation time: 100 hours (heat versus long-term penetration test) Examples 8 to 13 and Comparative Example 5 The sclerosing tree obtained by the method of 7 was subjected to vacuum defoaming for 20 minutes, and then gently poured into an aluminum foil cup having a bottom surface height of 2 cm and cast. The cast product was placed in an oven under predetermined hardening conditions to be hardened to obtain a test piece for penetration of a thickness of 2 mm. Using these test pieces, the transmittance (measurement wavelength: 375 nm, 400 i! in, 465 nm) at a time of 96 hours in a rc oven was measured by a spectrophotometer, and the rate of change was calculated. (Mechanical property test) The hardened resin compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to vacuum defoaming for 20 minutes, and then gently poured into a test piece having a width of 7 mm, a length of 5 cm, and a thickness of about 800 #m, and then casting in a model, and then The test piece was covered with a polyimide film. The test piece was cured under the curing conditions described in Tables 2 and 3 to obtain a test piece for dynamic viscoelasticity. Using these test pieces, a dynamic viscoelasticity test was carried out under the following conditions. Measurement conditions Dynamic viscoelasticity tester: TA-instrument, DMA-2980 Measurement temperature range: -30 ° C to 280 ° C Heating rate: 2 t: / min Test piece size: use cut into 5 mm x 50 mm (thickness about gooAm). 66 321483 201020279 Analysis conditions:

Tg: The Tan-5 peak point measured by ΜΑ is Tg. -30 ° C modulus: the modulus of elasticity at -30 ° C was measured. (LED illumination test) The curable resin compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to vacuum defoaming for 20 minutes, and then a precise discharge device was used in a syringe to mount a light-emitting element having an emission wavelength of 375 nm. Cast in a surface-mount LED. Thereafter, it is hardened under predetermined hardening conditions to obtain an LED for illumination test. In the illumination test, an illumination test was performed at 60 lnA equivalent to three times the predetermined current in order to perform the test under accelerated conditions. The detailed conditions are as follows. The measurement item was measured by using an integrating sphere for the illuminance around 1 hour and before and after the illumination, and the illuminance retention rate was calculated. After another two hours, after illumination, the surface state of the light-emitting element was observed. [Detailed conditions of illumination] Illumination wavelength: 375 nm ❹ Drive mode: constant current mode, 60 mA (specified current of light-emitting element is a) Driving environment: 25 ° C, 65% 321483 67 201020279 Table 2 Example 8 Example 9 Example 10 Comparative Example 5 Comparative Example 6 (Formulation) Compound A-1 100 ....... _ _ _ Compound A-2 Compound A-3 - 100 100 . . . Compound A-12 — — — 100 — ERL-4221 — — — — 100 Hardener B-1 30. 5 30. 0 31. 1 30. 3 — Hardener B-2 — — — — 71.8 (Mechanical property test) Tg 113 113 116 92 254 -30° C modulus 1449 1515 1615 1801 4567 Surface viscosity is no benefit (UV durability penetration test) 375nra 95% 95% 95% 94% 72% penetration maintenance rate 400nm 98% 98% 98% 96% 76% wear Permeation maintenance rate 465nm 100% 100% 100% 99% 90% Penetration maintenance rate* Hardener B-1: Hardener is prepared by preparing 1,3, 4-cyclohexanetricarboxylic acid-3, 4-anhydride (Mitsubishi) "MH-700G" ("Nippon Chemical and Chemical Co., Ltd."), which is a mixture of 30 parts of methyl hexahydrophthalic anhydride and hexahydrophthalic anhydride, manufactured by Gas Chemical Co., Ltd. 70 parts of the mixture was used as curing agent B-1. * Hardener B-2: Hardener is prepared by preliminarily preparing 1,3, 4-cyclohexanetricarboxylic acid-3, 4-anhydride ("H-TMA" manufactured by Mitsubishi Gas Chemical Co., Ltd.) "MH-700G" (manufactured by Shin Nippon Chemical & Chemical Co., Ltd.) of a mixture of hexahydrophthalic anhydride and hexahydrophthalic anhydride was used as a hardener B-2. *ERL-4221: An alicyclic epoxy resin manufactured by The Dow Chemical Company. * Hardening conditions: 120 ° C 2 hr + 140 ° C 2 hr (Examples 8, 9, 10, Comparative Examples 5, 6) * The unit of Tg is [°C], and the unit of modulus of elasticity at -30 °C is [MPa] . 68 321483 201020279 From the above results, it is understood that the curable resin compositions of Examples 8 to 10 using the oxoxane compound (A) of the present invention synthesized in a two-stage reaction are used as compared with the dimethyl siloxane unit. Content Concentration of Structure (Mohr/〇) Comparative Example 5 of the same compound has a high Tg and excellent heat recovery, and has a low elastic modulus at a low temperature, and is excellent in heat resistance and low modulus. Further, in Comparative Example 6 of the conventional alicyclic epoxy resin, it was confirmed that the light resistance and the low modulus of elasticity were superior.

69 321483 201020279 Table 3

(Formulation) Compound A-13 Compound A-14 Hardener B-3 Hardening accelerator C-1 (mechanical property test)

Tg -30°C Elasticity Surface Viscosity (UV Durability Penetration Test) 375nm Penetration Maintenance Rate 400nm Penetration Maintenance Rate 465nra Penetration Maintenance Rate (Heat Durability Penetration Test) 375nm Penetration Maintenance Rate 400nm Penetration Maintenance Rate 465 nm Penetration maintenance rate (weight change after hardening) 13) Weight retention rate Example 11 Comparative Example 7 100 -- 100 28. 9 29. 9 0.1 0· 1 97.4% 84.0% 99. 1% 89. 4% 100 % 96. 1°/〇95% 91°/〇70 321483 1 Hardener B-3: a mixture of mercaptohexahydrophthalic anhydride and hexahydrophthalic anhydride (New Japan Physical and Chemical Co., Ltd.) "MH-700G"). * Hardening accelerator C-1: A reaction accelerator for an epoxy resin and an acid anhydride is "U-CAT 18X" (trade name) sold by San-apro Co., Ltd. * Hardening conditions: unified to 120 ° C 2 hr + 140 ° C 2 hr 201020279 * Tg unit is [ ° C], -3 〇 ° C modulus of the unit is [Mpa]. *2) There is a foaming mark' and an appropriate sample cannot be obtained as a cured material for dynamic viscoelasticity. *3) Since the foaming trace of Comparative Example 7 in *2) was confirmed, when the ϋν durability penetration test sample was produced, the amount of reduction in the resin was measured to confirm the weight retention ratio. Further, the weight maintenance ratio was calculated by (weight of the cast product after hardening/weight of the cast product before hardening) χ100. In the curable resin composition of Comparative Example 7, a foaming mark was generated and it was not possible to form a normal cured product for dynamic viscoelasticity measurement. On the other hand, it was found that the curable resin composition of Example 11 can be made non-tacky. The cured product is a cured product having a low modulus of elasticity. Further, in the hardenable resin composition of Comparative Example 7, the amount of reduction of the resin before and after curing of the sample for UV durability penetration test was measured to be 9% by weight, and the curable resin of the example was used. The amount of reduction in the composition is limited to about 5%, and the amount of the curable resin composition of the present invention is reduced before and after hardening, and the casting of the LED package has less depression after hardening, so that the hardening of the present invention can be confirmed. In this regard, the resin composition was also applied to the composition for LED sealing. In addition, compared with Comparative Example 7, it was also found that the UV durability and heat resistance of the transmittance of Example 11 were also excellent. 71 321483 201020279 Table 4 Example 12 100 21. 4 0. 1 45〇C 1539 Helmet 88. 1% 93. 9°/〇99. 2°/〇 (Material) Compound A-15 Hardener B-3 Hardening promotion Agent C-1 (mechanical property test)

Tg -30°C Elasticity Surface Viscosity (UV Durability Penetration Test) 375nm Penetration Maintenance Rate 400nm Penetration Maintenance Rate 465nm Penetration Maintenance Rate* Hardener B-3: Use of fluorenyl hexamethylene phthalate , a mixture of hexahydro-dosing phthalic anhydride ("MH-700G" manufactured by Nippon Chemical and Chemical Co., Ltd.). * Hardening accelerator C-1: A reaction accelerator for an epoxy resin and an acid anhydride is "U-CAT 18X" (trade name) sold by San-apro Co., Ltd. * Hardening conditions: 120 ° C lhr + 150 ° C 3 hr * Tg unit is [ ° C], -30 ° C modulus of the unit is [MPa]. The curable resin composition of Example 12 of the present invention, which is synthesized using the two-stage reaction, is a cured product having a low modulus at a low temperature. 72 321483 201020279 Table 5 实施 Example 13 Comparative Example 6 Unsealed (mixed) Compound A-13 100 ERL-4221 A hardener B-2 - Hardener B-3 29. 1 Hardening accelerator Ci 0. 1 (UV Durability penetration test) 375nm 92. 5°/〇 penetration retention rate 400nm 96. 5% penetration maintenance rate 465nm penetration maintenance rate (LED illumination test) illuminance maintenance rate component surface state 100 71. 8 72% 76% 99. 7% 90% 91% colorless 21% brown color deterioration 'no sealant without resin injection 83% colorless simultaneous

* Hardener B-2: Hardener is prepared by pre-comprising 1,3, 4-cyclohexyl tridecanoic acid-3; 4-anhydride ("H-TMA" manufactured by Mitsubishi Gas Chemical Co., Ltd.) : "7_" (manufactured by Shin Nippon Chemical & Chemical Co., Ltd.) of a mixture of hydrogen phthalic anhydride and hexahydrophthalic anhydride, 5 parts of the mixed physicochemical agent B-2.更B 3 . "ΜΗ_7(10)G" which is a compound of methyl hexahydrophthalate or hexahydrophthalic anhydride (Nippon Chemical and Chemical Co., Ltd.) promotes 剤C 1 · epoxy resin and "U-CAT 18X" (trade name) sold by the company of fine aPr(R) Co., Ltd. for the reaction promoter of the acid anhydride. 73 321483 201020279 *ERL-4221: Epoxy resin modified by Dow Chemical Co., Ltd. * Hardening conditions: 1103⁄4 6 hr (Example 13) * Hardening conditions: 12 〇 ° c ihr + lSiTC 3 hr (Comparative Example 6) * The unit of Tg is [°C], and the unit of elastic modulus of -3 〇 °c is [MPa] From the above results, it has been found that the curable resin composition of Example 13 using the siloxane compound (A) synthesized in the two-stage reaction is used in an LED sealing material, and the alicyclic ring is used in comparison with the conventional one. Epoxy resin

In the curable resin composition of Comparative Example 6, the illuminance maintenance ratio was remarkably excellent. It is confirmed that the curable resin composition of the present invention is suitable. [Simple description of the drawing] No coffin. [Main component symbol description] helmet

321483 74

Claims (1)

201020279 VII. Patent application scope: • 1_ A reactive functional group-containing oxane compound having a chain polyoxynized segment and having a reactive functional group selected from an epoxy group, a fluorenyl group and a phenyl group Hydrolysis of a tris(C-Cio) alkoxydecane group based on a group, a block type oxane oxide oligomer of a condensed segment, and at least a portion of the hydrolyzed condensed segment containing at least one epoxy group The segment of the reactive functional group. 2. The oxoalkylated oxime containing a reactive functional group as claimed in claim 1 wherein the hydrolyzed condensed segment is sesquiterpene oxide 3. The reactive functional group-containing oxaxoxane compound of claim 1 or 2, which is obtained by the following two-stage reaction, the j-stage reaction is carried out by the formula (2) The decyl alcohol terminal polyoxyxane oil (b) is alkoxy decane compound (a) represented by the formula (1), and the sterol group is 1 equivalent with respect to the sterol terminal polyoxyxanic oil (b). The alkoxy equivalent of the compound is reacted and condensed in the range of 1.5 to 200 equivalents, and the second stage reaction thereafter is carried out by adding water to the obtained reaction liquid to hydrolyze and condense the remaining alkoxy group; (wherein a plurality of R3s may be mutually identical or mutually different, and represent a linear, branched or cyclic alkyl group having a carbon number of j to 10, an aryl group having 6 to 14 carbon atoms or a carbon number of 2 to 10 Alkenyl; m means an average of 2 to 2 〇〇〇) 75 321483 (1) 201020279 XSi(0R2)3 (wherein X represents a reactive functional group having no epoxy group; Ra represents a carbon number of 1 to 10 alkyl). 4. The reactive functional group-containing oxoxane compound of claim 3, wherein m is from 2 to 200. 5. The oxo-alkylated s-containing reactive functional group according to the ninth aspect of the patent, wherein the first-stage reaction is a sterol-terminated polyoxyxene oil (b) represented by the general formula (2). And the alkoxy decane compound (a) represented by the formula (1) and the alkoxy decane compound (c) represented by the formula (3), in the case of the octa alcoholic oil (8) relative to the sterol terminal i equivalent, the oxysphate compound (4) and the total equivalent of the alkoxy group of (c) are reacted and condensed in the range of 丨. 5 to 2 〇〇 equivalent, and the second stage reaction thereafter is carried out by adding water to the obtained In the reaction liquid, the remaining alkoxy group is hydrolyzed and condensed; (wherein a plurality of R3s may be mutually identical or mutually different, and represent a linear, branched or cyclic alkyl group having a carbon number of i to 10, an aryl group having a carbon number of 6 to 14 or a carbon number of 2 to 10 Alkenyl; m represents an average of 2 to 2 〇〇) XSi(OR2)3 (1) (wherein X represents a reactive functional group having an epoxy group; 匕 represents an alkyl group having 1 to 10 carbon atoms) (3) R4Si(0R2)3 has the same R2 or (wherein R4 represents a methyl group or a phenyl group; only 2 can be distinguished from the general formula (1) 321483 76 201020279', which means that the carbon number is 1 to 1 〇. base). The compound according to any one of claims 3 to 5, wherein the compound of the formula (2) is independently represented by a methyl group or a phenyl group; and each of the formula (1) Independently, it means methyl or ethyl. The only two of the formula (3) may be the same as or different from R2 of the formula (1), and each of them represents a methyl group or an ethyl group. _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The calcined compound's towel has a weight average molecular weight (MW) of 300 to 18 Å at the end of the formula (2). (2) The reactive functional group-containing compound according to any one of the first aspect of the invention, wherein the weight average molecular weight (Mw) is 2, 议.馨1〇·如 φ 立 立 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利 专利Either or both of the base or phenyl. ·=Please refer to the range of i or 10 of the patent range of the reactive functional group-containing calcined compound 'the towel' 1/2 half-dollar segment has an epoxy group 12~-functional functional group containing epoxycyclohexyl By. The functional group-based Wei pure compound_making method, the special one, the following two-stage reaction; the first-stage reaction system is the general formula (2) π sterol terminal polyfluorene oxide oil (b), Alkoxyalkylation of formula (1) 321483 77 201020279 &amp; (a) 'in the end of the polyoxo-oxygen oil (匕) relative to the linalool; g-alcohol 1 as i 'alkoxydecane compound ( a) the alkoxy equivalent of a.5 to 2 〇〇, reacts and condenses in the presence of a catalyst, and then the second stage of the reaction is carried out by adding water to the obtained reaction solution to make the remaining Alkoxy hydrolysis/condensation: (In the formula, there are a plurality of Rs which may be mutually the same or different from each other, and are independent of each other, and the linear, branched or cyclic alkyl group having a carbon number of 1 to 1 、, and the carbon number of 6 to 14 are Or an alkenyl group having 2 to 10 carbon atoms; m represents an average value of 2 to 2000) XSi(〇R2)3 (1) (wherein X represents a reactive functional group having no epoxy group; R2 represents a carbon number 1 to 10 alkyl groups). 13. The method for producing a reactive functional group-containing oxoxane compound according to claim 12, wherein m is from 2 to 200. A method for producing a reactive functional group-containing oxoxane compound, which comprises the following two-stage reaction, wherein the first-stage reaction is carried out by the general formula (2) The oil (b), and the alkoxy decane compound (a) represented by the formula (1) and the alkoxy decane compound (c) represented by the formula (3), in the end of the oxy-alcoholic acid (b) a sterol group of 1 equivalent, the alkoxy decane compound (a) and the total alkoxy group of (c) are in the range of 1.5 to 200 equivalents. The condensation reaction is carried out in the presence of a catalyst, and thereafter No. 2 78 321483 201020279 m The fat-long reaction system adds water to the obtained oxyhydrolysis/condensation; In the reaction product, in the remaining alkane (2) ^, a plurality of ones may be mutually identical or different from each other, and each of them is independent, and the linear number, branch or ring shape of the mosquitoes is not 1 to 1 〇. Burning base, carbon The aryl group of 6 to 14 or the alkenyl group of carbon number 2 to 1 () represents an average value of 2 to 200) (1) an functional group; r2 represents carbon XSi(〇R2)3 (wherein, X represents An alkyl group having an inverse number of 1 to 10 of an epoxy group) \ R4Si(0R2)3 (3) ' (wherein R4 represents a methyl group or a phenyl group; and R2 may be the same as or different from R2 of the formula (1), Each is independent, representing an alkyl group having a carbon number of i to 10). ❿15. The method for producing a reactive functional group-containing oxane compound according to any one of claims 12 to 14, wherein the manufacturing step is performed in a one-pot manner. 12. Stage responders. 16. The method for producing a reactive sulfonium-containing oxane compound according to any one of the items (8) of the fifth aspect of the invention, wherein the alkoxy decane compound of the formula (1): It is y?-(3,4~epoxycyclohexyl)ethyltrimethoxynonane or stone-(3,4-epoxycyclohexyl)ethyltriethoxy oxime. The method for producing a functional group-containing oxane compound according to any one of claims 12 to 71, wherein the sterol represented by the formula (2) The R3 of the terminal polyoxygenated oil (b) may be mutually identical or mutually different, and are each independently a methyl group or a phenyl group. The method for producing a reactive functional group-containing oxoxane compound according to any one of claims 13 to 15, wherein the alkoxy decane compound represented by the formula (3) is selected from a methyl group. At least one of trimethoxydecane, phenyltrimethoxydecane, decyltriethoxydecane, and phenyltriethoxydecane. A curable resin composition comprising the reactive functional group-containing oxosiloxane compound (A) and the curing agent (B) according to any one of claims 1 to 11. — 20. The curable resin composition of claim 19, wherein the hardening accelerator (C) is further contained. 21. A cured product for a photo-semiconductor, which is obtained by thermally curing a curable resin composition of claim 19 or 'r item 20. 22. An optical semiconductor component which is sealed by a hardened material for a light semi-conductor of claim 20. 80 321483 201020279 IV. Designated representative map: There is no schema in this case (1) The representative representative map of this case is: (). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: (2) 321483 201020279 Invention of manure instructions (This manual is in the style and order, please do not change it arbitrarily.] ※Please note the number of the application. ※Application number: ※Application曰: (2006.01) I. Name of the invention: (Chinese/English) ^ % ί2〇〇6*〇1&gt; Hydroxane compound, hardenable resin composition, hardened material and optical semiconductor element SILOXANE, HARDENING RESIN COMPOSITION, HARDENED SUBSTANCE THEREOF , AND OPTICAL SEMICONDUCTOR COMPONENT II. Abstract of Chinese Abstract: Suction side f2006 0n ❹ % (2〇〇6.0l\ The present invention relates to a novel reactive compound-containing Shihe oxygen compound (A), containing this dream oxygen burning a curable resin composition of the compound (A) and the curing agent (β), and an optical semiconductor element (for example, led) sealed with the cured product, and the light-resistant property of the sealed optical semiconductor element and low elasticity at a low temperature The above-mentioned oxoxane compound (A) has a chain polyfluorene chain segment and three having a group selected from the group consisting of a reactive functional group containing an epoxy group, a fluorenyl group, and a phenyl group. C1-C10) a hydrolyzed condensed segment of alkoxydecane, a hydrazine-type oxo-oxygenated oligomer, and at least a portion of the hydrolyzed condensed bond segment contains a bond having at least one reactive group of an epoxy group segment The dream oxygen-burning compound can be obtained by the following first-stage reaction and the subsequent second-stage reaction, the first-stage reaction: the pure base of the recorded compound relative to the crane equivalent of the _ terminal (tetra) oxy-oil (b) The reaction is carried out within the range of the equivalent value; 'I Phase 2 reaction: the base of the sputum reaction in the presence of water in the presence of water. The first step 321483 revision 1 201020279 Comparative Example 6 : Compositions using ERL-4221 and a curing agent Examples and comparative examples described in Table 3 are as follows. Example 11: Composition using Compound Α-13, Hardener Β~3, and Hardening Accelerator C-1 Comparative Example 7: Composition using Compound Α-14, Hardener, and Hardening Accelerator C-1 The examples described in Table 4 are as follows. Example 12: Using Compound Α-15, Hardener Β-3, and Hardening Compositions for promoting the sword ci The examples and comparative examples described in Table 5 are as follows. Example 13: Comparison of the composition of the compound Α-13, the hardener Β·~3, and the hardening accelerator 4 C-1 Example 6: Using ERL-4221 and the composition of hardener Β-1 The curable tree compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to the following penetration test, mechanical property test (dynamic viscoelastic test), and LED illumination test, and the results were shown in Tables 2, 3, 4, and 5. (UV Durability Penetration Test) The curable wax compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to vacuum defoaming for 20 minutes, and then gently poured. Cast into an aluminum foil cup with a bottom diameter of 5 cm and a height of 2 cm. The cast product was placed in an oven under predetermined hardening conditions to be hardened to obtain a test piece for penetration of 2 mm in thickness. Using these test pieces, the transmittance (measuring wavelength: 375 nm, 400 nm, 465 nm) before and after ultraviolet irradiation was measured by a spectrophotometer, and the rate of change was calculated. The ultraviolet irradiation conditions are as follows. 65 321483 Revised 201020279 Ultraviolet Irradiation Machine: EYE SUPER UV TESTER SUV-Wll Temperature: 60°C Irradiation Energy: 65mW/cm2 Irradiation Time: 100 Hours (Heat Durability Penetration Test), Examples 8 to 13, Comparison The curable resin composition obtained in Examples 5 to 7 was subjected to vacuum defoaming for 20 minutes, and then gently poured into an aluminum foil cup having a bottom diameter of 2 cm in height and cast. The cast product was placed in an oven under predetermined hardening conditions to be hardened to obtain a test piece having a thickness of 2 for penetration. Using these test pieces, the transmittance (measurement wavelength: 375 nm, 4 〇〇 (10), 465 nm) was measured by a spectrophotometer in a 15 ounce oven for 96 hours, and the rate of change was calculated. (Mechanical property test) The curable resin compositions obtained in Examples 8 to 13 and Comparative Examples 5 to 7 were subjected to vacuum defoaming for 20 minutes, and then gently poured into a width of 7 mm, a length of 5 cm, and a thickness of about 800 //m. The test piece was made of pounds in the model and then covered with a polyimide film from above. The cast product was cured according to the hardening conditions described in Tables 2 and 3, and was taken to a test piece for dynamic viscoelasticity. Using these test pieces, a dynamic viscoelasticity test was carried out under the following conditions. Measurement conditions Dynamic viscoelasticity tester: TA-instrument, DMA-2980 Measurement temperature range: -30 ° C to 280 ° C Heating rate: 2 ° C / min Test piece size: use cut into 5 mm x 50 丽 (thickness of about 800 /im). 66 321483 201020279 Invention of manure instructions (This manual is in the style and order, please do not change it arbitrarily.] ※Please note the number of the application. ※Application number: ※Application曰: (2006.01) I. Name of the invention: (Chinese/English) ^ % ί2〇〇6*〇1&gt; Hydroxane compound, hardenable resin composition, hardened material and optical semiconductor element SILOXANE, HARDENING RESIN COMPOSITION, HARDENED SUBSTANCE THEREOF , AND OPTICAL SEMICONDUCTOR COMPONENT II. Abstract of Chinese Abstract: Suction side f2006 0n ❹ % (2〇〇6.0l\ The present invention relates to a novel reactive compound-containing Shihe oxygen compound (A), containing this dream oxygen burning a curable resin composition of the compound (A) and the curing agent (β), and an optical semiconductor element (for example, led) sealed with the cured product, and the light-resistant property of the sealed optical semiconductor element and low elasticity at a low temperature The above-mentioned oxoxane compound (A) has a chain polyfluorene chain segment and three having a group selected from the group consisting of a reactive functional group containing an epoxy group, a fluorenyl group, and a phenyl group. C1-C10) a hydrolyzed condensed segment of alkoxydecane, a hydrazine-type oxo-oxygenated oligomer, and at least a portion of the hydrolyzed condensed bond segment contains a bond having at least one reactive group of an epoxy group segment The dream oxygen-burning compound can be obtained by the following first-stage reaction and the subsequent second-stage reaction, the first-stage reaction: the pure base of the recorded compound relative to the crane equivalent of the _ terminal (tetra) oxy-oil (b) The reaction is carried out within the range of the equivalent value; 'I Phase 2 reaction: in the presence of water, the base of the reaction of the sputum reaction, the base of the stalk of the stalk, should be read. The first order 321483 revision 1 201020279 III. Abstract: The present invention relates to a novel reactive functional group containing a siloxane (A), a hardening resin composition including the siloxane (A) and a hardening agent (B), and an optical semiconductor component (such as LED) hermetically sealed by a hardened substance thereof, the hermetically sealed optical semiconductor component demonstrates excellent resistance to light and low elasticity at low temperature. The siloxane (A) is a block-type siloxane oligomer having a chain of silicone segment and a hydrolysis and condensation segment of trialkoxysilane (Cl-CIO) containing a gro Up selected from the group consisting of epoxy-containing reactive functional group, methyl, and ethyl, at least a portion of the hydrolysis and condensation segment contains at least an epoxy-containing reactive functional group. The siloxane is obtained by the first step reaction And the ensuing second step reaction described hereunder. 1st step reaction: Reacting the siloxane compound in the condition that the alkoxy equivalent is within 1.5 to 200, relative to one equivant of silanol group of silanol ending polysilicone oil; 2nd step reaction: In the presence Of water, subject the said alkoxysilane and the alkoxy group of the product obtained from 1st step reaction, to undergo hydrolysis and condensation reaction. 2 321483