TW201247745A - Organopolysiloxane, method for producing the same and curable resin composition containing the same - Google Patents

Abstract

The present invention provides an organopolysiloxane, which can forms a cured material with excellent balanced characteristics on hardness, gas barrier properties, yellowing resistance, light resistance, cold and heat shock resistance, and adhesiveness to substrate. The organopolysiloxane is a group containing one or more unsaturated bonds in one molecule, and containing the constitutional unit contains any combination of (1)F1 and M1, (2)F1 and T, (3)F1, M1, and T, in which the constitutional units F1, M1, and T are represented by the following formulae (1) to (3). (wherein, R1 represents any group selected from of the group consisting of: a substituted or unsubstituted alkyl group with a carbon number of 1 to 10, a substituted or unsubstituted cycloalkyl group with a carbon number of 3 to 10, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group; R2 represents an unsaturated bond-containing group with a carbon number of 2 to 10; X represents a divalent hydrocarbon group with a carbon number of 2 to 10, a, b, c, each independently represents an integer more than or equal to 1. wherein, F1 represents a constitutional unit of cyclic organopolysiloxane.)

Description

201247745 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to an organic polyoxic oxide, a method for producing the same, and a curable resin composition containing the above organopolysiloxane. [Prior Art] It has been known that an epoxy resin composition using an acid anhydride-based curing agent can form a transparent cured product, and is suitable as a sealing material for an optical semiconductor element such as a light-emitting diode or a photodiode. The organic resin skeleton is, for example, a double-type A type epoxy resin, a double-prepared f-type epoxy resin, and a mercapto-3'4-epoxycyclohexanecarboxylic acid (3-, 4-epoxycyclohexyl) ester. The epoxy resin-based epoxy resin composition can be used in the field of optical semiconductor components. However, in recent years, with the advancement of the high performance of the optical semiconductor, the sealing material for the optical semiconductor element is required to have more excellent heat resistance, light resistance, and the like, and the epoxy resin composition generally known in the prior art is The characteristics are not sufficient. In view of the above problems, various proposals have been made in various resin compositions for optical semiconductor applications. For example, a thermosetting resin composition for photo-semiconductor use in which a specific polyoxymethylene composition is subjected to a hydrogenation reaction by a hydrazine is proposed (refer to Patent Document 1). At the same time, a technique for using a specific polyoxyl composition having improved hardness as a photo-semiconductor is also proposed (refer to, for example, Patent Document 323923 5 201247745 " In addition, there is proposed a method in which a specific structural oxyalkylene is contained therein. The composition of optical semiconductors is organically polymerized. For example, there is also a proposal to use a methyl propyl compound as a technique for optical semiconductor use (see, for example, gas grade others) and a proposal for an epoxy resin composition 4, 4). In the technique of ink and ink, etc., the coating material_compound (refer to Patent Documents 5 and 6) and the use of epoxy compounds and materials are also used in this technology. A technique containing a specific resin to control its hardness: no mechanical properties (refer to the special product of 〇 〇 〇 〃 〃 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前 先前Japanese Patent Laid-Open Publication No. 2008-201185 [Patent Document 3] Japanese Patent Laid-Open Publication No. 2008-201009 (Patent Document 4) [Patent Document 6] Japanese Patent Laid-Open Publication No. Hei 9-328634 (Patent Document 7) Japanese Patent No. 4235698 (Summary of the Invention) However, the above-mentioned previously proposed There is still a problem in the technique. The thermosetting resin composition proposed in Patent Document 1 is resistant to 323923 6 201247745. Although the heat yellowing property and the goodness are good, the hardness of the cured product is still low and the damage is liable to occur. It is difficult to make At the same time, the gas barrier properties and the adhesion to the substrate are also low, so that it is not suitable for use in the sealing material for optical semiconductors. The polyfluorene composition proposed in Patent Document 2 is for improving the hardness. When a phenyl group is used, the phenyl group is a cause of the reduction of heat-resistant yellowing and light resistance. Therefore, it is not suitable for use in the use of a sealing material for an optical semiconductor. The composition proposed in Patent Document 3 is in hardness and adhesion. Although it is excellent in terms of properties and gas barrier properties, the isomeric cyanurate which forms the basic skeleton is a cause of reducing heat-resistant yellowing and light resistance, and thus it is not necessarily satisfactory in terms of the use of the sealing material for optical semiconductors. The polyfluorene-oxygen composition proposed in Patent Document 4 is excellent in heat-resistant yellowing and light resistance, and there is no part in the molecular structure that can relieve stress. When performing environmental change tests such as thermal shock test. 'It will cause the hardened material to rupture. That is, in the use of optical semiconductors', the resin will be cracked when the switch is operated at 0N-0FF, which is related to the disconnection problem. At the same time, the degree of gas barrier properties and the adhesion to the substrate is not achieved. The materials proposed in Patent Documents 5 to 7 have good gas barrier properties and good adhesion. Since the epoxy resin composition is changed, it is not satisfactory in terms of heat yellowing resistance and light resistance. As described above, the resin composition previously proposed has hardness, gas barrier property, heat yellowing resistance, In terms of all the characteristics of light resistance, thermal shock resistance, and adhesion to a substrate, it has not been possible to obtain a cured product which satisfactorily satisfies the degree required for optical semiconductor applications and coating materials such as 323923 7 201247745. It is also an object of the present invention to provide a property that satisfies all of the properties of hardness, gas barrier properties, heat yellow resistance, light resistance, thermal shock resistance, and adhesion to a substrate, particularly in optical semiconductor applications. An organic polyoxyalkylene which is required to have a well-balanced cured product, a method for producing the same, and a curable resin composition using the same, and a photo-conductive wafer bonding (die__bonding) material and a coating material which are necessary for the above characteristics , a hardening resin composition for nanoimprinting and an ink. The inventors of the present invention have solved the above-mentioned problems by obtaining a hardening resin composition of an organic polyfluorene having a characteristic structure, and the above object can be attained. That is, the present invention is as follows. [1] The French eucalyptus organic conjugate has one or more unsaturated i 1 in one molecule, and has the constituent units Μ, Ml, Τ in the following general formulas (1) to (3) (i) The constituent units of any combination of F1 and Ml, (ii) F1 and τ, (iii) FI, ΜΙ and τ.丫, FI: (RlSi〇2/a)a 323923 8 201247745 (R12s\o^/2) Μ 1 : ---(2) (R1.Si03/2 ) TC · · · ( 3 ) (The above formula In (1) to (3), r1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 1 ring carbon number, or a substituted or unsubstituted aryl group. And a ninja selected from the group consisting of a substituted or unsubstituted aralkyl group, R represents a carbon number of 2 to 1 oxime containing an unsaturated bond; X represents a carbon number of 2 to 10. a divalent smoky group having 2 to 10 carbon atoms, a, b, and c each independently represent an integer of 1 or more, wherein pi represents a constituent unit of the cyclic organopolyoxane.) [2] as in the above [1] In the above-mentioned general formula (1) to (3), a, b, and c satisfy the following general formula (I). 0. l^a/ (b+c) ^5- (1) [3] The organopolyoxyalkylene as described in the above [1] or [2], the constituent unit represented by the above formula (〇) R2 in F1 is an acryloxy group or a mercapto acryloxy group. [4] The organopolyoxane according to any one of the above [1] to [3] wherein 'the constituent units represented by the following general formulae (4) to (6) are: D1, D2, D3 Any of them. 323923 9 201247745 D 1 : ( Rl2Si02/2) · · X—

D3: (Rl2Si02/2) (6) j In the above formulae (4) to (6), R1 represents a substituted or unsubstituted filament of 1 to 1 G, a substituted or unsubstituted carbon number of 3 to 1 G. Any one selected from the group consisting of a ring-fired or unsubstituted filament and a substituted or unsubstituted radical; Χ represents a divalent hydrocarbon group having a carbon number of 2 JL 1 Å. Wherein 'Dl, D2 denotes a constituent unit of a cyclic organic polyoxygen oxymethane, and (10) denotes a constituent unit of a chain-like organopolyoxane. [5] The organic polyoxo-oxygenate according to any one of the above (1) to (4), and the constituent unit s represented by the following formula (7), and the formula (?) The content of the constituent unit can satisfy the following general formula (π) with respect to the content of the structural unit F1 shown in the charging formula (1). d/a ^0. 1 . . · ( Π)

s : ( R1HSi02 / 2)d (the above formula (7) + ' R1 Table (4): substituted or unsubstituted carbon number i to 1 〇 alkyl group, substituted or unsubstituted carbon number 3 phantom (tetra) ring present, substituted or Unsubstituted silk and any one selected from the group of Fangxian County. The towel's composition unit S (4)-like organic polycica 323923 201247745 oxane constituent unit.) as above [1] The organic polyoxo oxygen atmosphere according to any one of the above aspects, wherein the constituent unit F1 as shown in the above (1) is contained as a constituent unit containing R2. The organic polyoxoxime according to any one of the above [1] to [5], wherein the composition unit F1 and the lower formula (8) represented by the above formula (1) are contained. The constituent unit F2 is also a constituent sheet containing the above R2. (In the following general formula (8), R21 is contained in the above R2.) P 2 : Y—R21 (R^Sio^z) • (8) (in the above formula (8), R1 Represents: a substituted or unsubstituted alkyl group having up to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 1 ring carbon number, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group. Any one of the selected groups; R21 (4) olefinic oxy or methacryloxy group is selected from a divalent hydrocarbon group having 2 to 10 carbon atoms. wherein F2 represents a constituent of a chain organopolysiloxane. [8] 〇) - an organic material oxy-combustion, wherein, as described in the above-mentioned item [1] to [7], the organic polycoin is further reduced to the following: Cyclic organic poly 323923 represented by the general formula (9)

R21 (the above formula (9) towel 'R1 represents a substituted or unsubstituted carbon number i to 10 alkyl group, substituted or unsubstituted carbon number 3 to 1 fluorene cycloalkyl group, substituted or undrawn wire Any one selected from the group consisting of silk or fragrans; R21 represents a propenoxy or methacryloxy group; χ represents a divalent hydrocarbon group having 2 to 1 carbon atoms; e represents i or more An integer: f represents an integer of 0 or more; e+f represents an integer of 3 to 2 。.) [9] An organopolyoxane, wherein, in the above (1) to [8], relative to 10 parts by mass The organic poly-fibrin shown in any one of the formulas further contains a compound represented by the following formula (1Q) in an amount of from 1 to _ parts by mass. . Ψ R1 R1 R1

nSiO^SiO^^iO)-(SiO)-JX Rl Y R1 γ R21 R1—SiO—(Si R1 R1 <si〇)r-si- •R1 R1 (the above formula U0) towel, R1 is represented by: Substituted or unsubstituted filaments, substituted filaments substituted by number of rings 3 to 1G = unsubstituted aryl groups and substituted or unsubstituted aromatic filaments 1? 201247745 Any one of them; R21 means propylene-oxyl or A a propylene oxy group; χ represents a divalent hydrocarbon group having 2 to 10 carbon atoms; g represents! The above integer; 匕 represents an integer above ;; i represents an integer from 0 to 20. [10] The organopolyoxane as described in any one of the above [1] to [9] wherein the cyclic organopolyoxane represented by the following formula (9) is contained and the following a compound represented by the formula (10), R1 R1 v^iC% - {SiO)jX R1 R21 • · ( y ) (in the above formula (9), 'R represents a carbon number i from a substituted or unsubstituted Any one selected from the group consisting of alkyl, substituted or unsubstituted cycloalkyl having 3 to 1 ring carbon, substituted or unsubstituted aryl, and substituted or unsubstituted aryl group; R21 represents C Glycoloxy or mercaptopropenyloxy; X represents a divalent hydrocarbon group having 2 to 10 carbon atoms; e represents an integer of 1 or more; f represents an integer above 〇; and e+f represents an integer of 3 to 20.) R1 R1 R1 R1

X R1 I R1 V

I , III r21 R1—SiO—iSiO^Si—R1 R1 R1 R1 10) 323923 13 201247745 (In the above formula (ίο), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substitution or Any one selected from the group consisting of an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; R21 represents an acryloxy group or a methacrylium group Oxyl; χ represents a divalent hydrocarbon group having an inverse number of 2 to 10; g represents an integer above 丨; h represents an integer greater than 0; i represents an integer from 〇 to 2〇.) The peak intensity obtained by mass spectrometry is calculated by the following formula (111), and the content of the compound represented by the above formula (1〇) [WB] is relative to the content of the compound represented by the above formula (9) [WA] Ratio: The value of [WB]/[WA] is 〇1 or more and 2〇〇 or less. · [Number 1] [WB] / [WA] = mass and sodium mass in accordance with the general formula (1〇) structure: the intensity of the peak corresponding to the total mass / the mass of the structure conforming to the general formula (4) and the sodium mass 23 The organic polyfluorene oxide according to any one of the above [1] to [10] wherein the above R1 is An alkyl group having 1 to 10 carbon atoms. The organopoly group according to the above [12], wherein the above R1 is a methyl group, or any one of the above [1] to [Π]. [13] 323923. The organic poly>5 oxirane according to any one of the above [1] to [12], wherein the above R2 contains an acryloxy group or a mercaptopropenyloxy group, and The functional group equivalent weight of the propylene methoxy group or the methacryl methoxy group is from 210 to 2,100 g / 摩尔 [14] The organic polysiloxane according to any one of the above [1] to [13], which has an average weight. The molecular weight is 700 to 5000000, and the viscosity at 25 ° C is 50 to 1000000 mPa · s. [15] A method for producing an organopolyoxane according to any one of the above [1] to [14], which has the following steps: The hydrogenated polyoxyalkylene (al) shown in (11) and the hydrogenated polyoxyalkylene (a2), i) having one or more hydrogen atoms directly bonded to a halogen atom, have two or more direct bonds. a vinyl group-containing organopolyoxane (bl) bonded to a vinyl group of a halogen atom or a polyoxyalkylene (b2) having two or more hydroxyl groups directly bonded to a halogen atom, and ii) having 2 molecules in one molecule The addition reaction of the above organic compound (c) having an unsaturated bond is carried out in the presence of the catalyst (d) of Rishi, R1 R1 -(SiC%-(^iC% H R1 --. (11) 323923 15 201247745 (In the above formula (11), R1 represents an alkyl group having a carbon number of from 1 to 10 substituted or unsubstituted, a substituted or unsubstituted cycloalkyl group having from 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group Any one selected from the group consisting of a substituted or unsubstituted aralkyl group; j represents an integer of 1 or more; k represents an integer above 〇; j+k represents 3 to 20 [16] The method for producing an organopolyoxane according to the above [15], wherein the step of the above-mentioned addition reaction comprises: a step of preparing a reaction liquid, and a reaction liquid in the above Adding a step of the hydroxylation reaction catalyst (d), wherein the 'anti-ship contains the hydrogenation of the feed (11) material (tetra), and the above-mentioned argon having the atom directly bonded thereto 24 Wei (a2), mats, solids, etc., which are directly bonded to the vinyl group of the ruthenium atom. 聚聚气院(Μ) and an organic compound having two or more unsaturated bonds in one molecule. The ruthenium of the Shixi atom has two or more organic compounds (c) which are directly bonded to the oxirane (b2) and one molecule and have an unsaturated bond. [17] ^ In the method for producing an organic polyoxanthene of the above-mentioned item 15, wherein the addition of the anti-red step is carried out as follows (4): wherein the reaction liquid contains the above formula (U) Bonding to the above 7 atoms U 1 or more straight molecules having 2 or more poly w (a2) and 1 unsaturated bond Compound (c); 323923 16 201247745 The step of forming an adduct is to form the above-mentioned reaction catalyst (d) to form the above-mentioned general formula (丨丨), and to add the gasification reaction (al), as described above. The hydrogenated polyoxyalkylene (a2) having one or more hydrogenated polyoxygenated atoms in the plant and the anthracene of the organic compound (c) bonded to the hydrogen of the halogen atom and the bond have 2 The above-mentioned non-saturated addition step is carried out in the above reaction liquid, and the ethyl group directly bonded to the ruthenium atom has two or more (bl) or two or more direct bonds to the ruthenium group. Diorganopolyoxyalkylene (b2). The hydroxy group of the atomic hydroxyl group [18] A curable resin composition containing the two parts by mass of the thermal radical generating agent as described in any one of [1] to [14] . And a photo-free radical generating agent having a mass fraction of 0 parts by weight as described in any one of [1] to [14]. Rolling alkane and 0.5 to 20 [20] The hardening property as described in the above [18] or [19], wherein the layered smear is as described above (1) to [1] with respect to the 1 enamel IP tree. Any one of the organopolyoxanes t J.纟 又 又 3 3 ο ο ο 21 如 如 如 如 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 The organic polyoxazine calcined according to any one of the above [n to [14], further containing 0.001 parts by mass or less of the (d) hydrogenation reaction catalyst. [22] The curable resin composition according to any one of the above [1] to [21], wherein the organic material according to any one of the above [1] to [14], with respect to 100 parts by mass Polyoxane, which also contains 炱.1炱50 Ϊ 之 of inorganic oxide. [23] A sealing material for an optical semiconductor, comprising the curable resin composition according to any one of the above [18] to [22]. [24] A die bonding material for an optical semiconductor, comprising the curable resin composition according to any one of the above [18] to [22]. [25] A coating material comprising the curable resin composition according to any one of the above [18] to [22]. [26] A curable resin composition for a nano-imprint, comprising the curable resin composition according to any one of the above [18] to [22]. [27] An ink comprising the curable resin composition and the coloring agent according to any one of the above [18] to [22]. 323923 18 201247745 [28] An optical semiconductor package which is formed by the sealing material for an optical semiconductor according to the above [23]. (Effects of the Invention) According to the present invention, it is possible to obtain all properties of hardness, gas barrier properties, heat yellow resistance, light resistance, thermal shock resistance, and adhesion to a substrate, and to form them for use in an optical semiconductor. The organic polychlorination of the hardened material and the curable resin composition using the same can be satisfactorily balanced. According to the present invention, it is also possible to provide a sealing material for an optical semiconductor having the above characteristics, a wafer bonding material for an optical semiconductor, a coating material, a curable resin composition for nanoimprint printing, a material useful in the field of ink printing, and the like. An optical semiconductor package formed of a sealing material for an optical semiconductor. [Embodiment] Hereinafter, embodiments of the present invention (hereinafter referred to as "this embodiment") will be described in detail. However, the present invention is not limited to the following description, and various modifications can be made without departing from the spirit and scope of the invention. [Organic Polyoxane] The organopolyoxane of the present embodiment has a group of one or more unsaturated bonds in one molecule, and has a constituent unit represented by the following general formulae (1) to (3). (i) F1 and Μ (ii) F1 and Τ, 323923 19 201247745 (iii) Organopolyoxyalkylene of any combination of FI, Ml and Τ in FI, M1, T.

FY—R2 (R1Si02/2 a X Μ Τ (F^SiOA) (R1Si03/2 ) w (2 (3) In the above formula (1) to (3), R1 represents a substituted or unsubstituted carbon. Any one selected from the group consisting of an alkyl group having 1 to 10 alkyl groups, a substituted or unsubstituted carbon number 3 to a cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; R2 represents The carbon number 2 1 contains a group of an unsaturated bond; X represents a divalent nicotine group having a carbon number of 2 to 10; and γ represents a divalent hydrocarbon group having a carbon number of 2 to 1 d, d, b, and e each independently represent an integer of 丨 or more. _, F1 represents a constituent unit of a cyclic organopolyoxane. In the form of a human form of organic poly-coin, (4) New Zealand, 3 has the following general formulas (4) to (6) It is preferable to form an organic polyoxane of D2 and D3. < .D1 D 1 ·· ( Rl2Si〇2/2) · · · ( 4 ) X—· D 2 · ( R1SI〇2, 2) · ·, 323923 20 201247745 D 3 (Rl2Si〇2/2) (6) In the above formulae (4) to (6), Ri represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted. a cycloalkyl group having 3 to 1 Å carbon, a substituted or unrecited green, and a substituted or unsubstituted base. Any one selected from the group; X represents a divalent hydrocarbon group having a carbon number of 2 to 1 Å, wherein D1 and D2 represent a constituent unit of a cyclic organopolysiloxane, and D3 represents a composition of a chain organopolysiloxane. The organopolysiloxane of the present embodiment is preferably a content of a constituent unit s represented by the following formula (?) and a constituent unit s represented by the formula (7), with respect to the above formula. (1) The content of the constituent unit F1 shown is an organic polyoxane of the following formula (II): d/a ~0, 1 * .............. (II) When the constituent unit s represented by the following formula (7) is contained in a large amount, there is a concern that SiH reacts with an unsaturated bond to colloidalize during storage of the solvent or during storage, and the product is stable in productivity. From the viewpoint of preserving stability, it is preferred to satisfy the above formula (II). (R1HSi02/2) b. In the above formula (7), R1 represents: substituted or unsubstituted Any one selected from the group consisting of a C 1 to 10 alkyl group, a substituted or unsubstituted C 3 to 1 fluorene cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; Composition The position S represents a constitutive unit of a cyclic or chain-like organopolyoxyalkylene 323923 201247745. Further, the organic polyoxymethane of the present embodiment is a constituent unit containing the above r2 from the viewpoint of the hardness of the cured product. It is preferable that the organic polywei is contained only in the constituent unit F1 represented by the above formula (1). This is because the crosslinking density of the cured product can be improved when only the constituent unit F1 is formed. Further, the "constituting unit containing R2" includes a constituent unit of R21 in the subordinate concept of R2, and also includes the following general formulae (8) to 〇〇). In other words, the above-mentioned "constituent unit F1" represented by the above formula (1), which is a constituent unit containing the above-mentioned R2, means "although the constituent unit of the formula (1) is not contained, but The formulae (8) to (1〇) containing the constituent units of the following RZ1 are not contained. In addition, the organic polyoxylizing in the state of the present invention contains the above-mentioned general formula (1) from the viewpoint of the workability of the curable resin composition containing the organic polyoxyalkylene at a low viscosity. It is preferable that the constituent unit F1 and the organic polyacetal of the constituent F2 represented by the following formula (8) are formed. This is because, when one part of SiH is replaced by a difunctional SiH, it is possible to suppress the formation of a crosslinked structure of the oxane, thereby reducing the viscosity. Y—R21 p 2 : ( R12Si〇i, 2) • (8) In the above formula (8), R represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted. Any of the cycloalkyl groups having a carbon number of 3 to 10, 323923 22 201247745 generation or untaken green, and the face of the money; 1^ means propyloxy or methyl (tetra) decyloxy. A divalent hydrocarbon group having 2 to 10 carbon atoms. Its φ, soil ' γ octopus is a fresh position. 〇 'F2 钱 状 状 有机 有机 有机 F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F F Further, the Q.丨 to (10)f amount j has a structure of the following formula (9), and the degree of crosslinking of the cured product can be increased, thereby improving hardness and gas barrier properties. The content of the cyclic organopolyoxane represented by the following formula (9) is preferably from 5 to 80 parts by mass, preferably from 90 to 80 parts by mass. W^OIXIR2

J 1 ο 1 RIsi— R • (9) In the above formula (9), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon number of 3 to ίο Any one selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; R21 represents a propylene fluorenyloxy group or a fluorenyl propylene oxy group β χ represents a stone anastomosis 2 a divalent hydrocarbon group to 1 Torr. e represents an integer of 1 or more. f represents an integer of 3 to 20 in an integer of 〇. In addition, the organic polyoxanthene of the present embodiment is a compound represented by the following formula (10), and the organopolyoxane component thereof is 100 parts 323923 201247745 parts, preferably 0.01 to 1000 parts by mass. When the compound of the formula (10) is contained therein, flexibility can be imparted to the cured product, so that the cold thermal shock resistance can be improved. The content of the compound represented by the following formula (10) is preferably from 0.03 to 900 parts by mass, more preferably from 0.05 to 750 parts by mass.

SiO-(SiO)i-Si-R1 R1 R1 • (10) In the formula (10), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon number of 3 to Any one selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group. R21 represents an acryloxy group or a methacryloxy group. X represents a divalent hydrocarbon group having 2 to 10 carbon atoms. g represents an integer of 1 or more; h represents an integer of 0 or more. i represents an integer from 0 to 20. Further, the organopolysiloxane of the present embodiment contains the cyclic organopolyoxane represented by the above formula (9) and the above-mentioned viewpoint from the viewpoint of balance between hardness, gas barrier properties and cold shock resistance. a compound represented by the formula (10), and the peak intensity obtained by the matrix-assisted free time-of-flight mass spectrometry is calculated by the following formula (III), and the compound represented by the above formula (10) [WB] with respect to the content of the compound represented by the above formula (9) [WA]: the value of [WB] / [WA], which is 0.1 or more and 20. 0 or less 323923 24 201247745 is preferably '0.3 or more 18 The following is better, 〇 5 or more and 15 or less [number 2] is better. _ / between - the intensity of the peak corresponding to the sum of the mass of the (8) structure and the mass of the nano-mass / the strength of the bee corresponding to the total mass of the mass of the general formula (4) and the nano-mass 23 ··· 1 CIII) · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · Or unsubstituted woven fabrics = ^, for example, methyl, ethyl, propyl, butyl, isobutyl, = dibutyl, pentyl, neopentyl, hexyl, cyclopentyl, a cyclohexyl group or the like, a calcining group having from 1 to 10; a cycloalkyl group having a carbon number of 3 to 1 () in the ring, a cyclobutyl group, a cyclopentyl group, a ring = a group, a cyclooctyl group, a cyclodecyl group or the like; An aryl group such as a phenyl group, a phenyl group, a dimethyl group, a cumyl group or a trimethylphenyl group; an aryl group such as a phenyl group, a phenanthrene group or a phenyl group; or a bond on a carbon atom of such a group; A propyl group, a cyanoethyl group, a chloropropyl group, a 3, 3, 3_trimethyl propyl group, etc., which are partially or wholly substituted by a radical, a cyano group and a (iv) atom. In the case of R1, from the viewpoint of light resistance, an alkyl group having a carbon number of 丨 to 1 Å is preferred.匕 匕 simultaneous 'R1' is from the viewpoint of the heat-resistant yellowing and the material properties of the composition of the organic polysulfide and the curable tree scorpion of the present embodiment, and the thiol group is more as described above, and R2 represents the carbon number. 2 to 1G group containing an unsaturated bond 323923 25 201247745 Examples thereof include a vinyl group, an allyl group, an isopropenyl group, a 3-butenyl group, a mercaptopropyl group, a 4-pentyl group, and a 5-hexyl group. An unsaturated chain hydrocarbon group such as a dilute group, a 6-heptyl group, a 7-menthyl group, an 8-decenyl group or a 9-nonenyl group; an unsaturated cyclic hydrocarbon group such as a cyclohexenyl group or a nortenyl group; An unsaturated hydrocarbon group containing an ether bond such as an ether group or an allyl ether group; a cyclic unsaturated hydrocarbon group such as a cyclohexenyl group; and an unsaturated fatty acid ester group such as an acryloxy group or a mercapto propyleneoxy group. In the 'reactivity of forming a curable resin composition to be described later', that is, the thermal curing or photohardening is easy to carry out and the reaction proceeds rapidly, and the propylene oxy group represented by the following formula (12) Or a methacryloxy group represented by the following formula (13) (these are collectively referred to as (fluorenyl) propylene oxy group). -o-c-c=ch2 0 · · -(12) -〇-c-c=ch2 O CH3 r Λ Ο \ ό · · · (1 3 ) As described above, 'X' represents a divalent hydrocarbon group having 2 to 10 carbon atoms. Examples thereof include: -(CH2)2-, -(CH2)3-, -(CH2)4-, -(CH2)5_, -(CH2)6---(CH2)8---(CH2 ) i〇---CH(CH3)CH2- > -C(CH3)2-, etc., especially from -(CH2)2-, -(CH2)3-, -(CH2)4- It is preferred from the viewpoint of reactivity, that is, thermosetting or photohardening is easy to carry out and rapid reaction. As described above, Y represents a divalent hydrocarbon group having 2 to 10 carbon atoms. Examples thereof include: -(ch2)2-, -(ch2)3-, -(ch2)4~, -(CH2)5-, -(CH2)6-, -(ch2)8---( CH2)i〇---CH(CH3)CH2~, c(CH3)r 323923 26 201247745, etc., especially by 2) 3_, - (CL raw materials are easy to take, ie their thermal hardening or photohardening is easy and fast It is preferable from the viewpoint of the reaction. As described above, the united towel of the present embodiment has the structures (i) F1 and m, (ii) F1 and τ, (iii) Fl, mi and τ. The constituent unit of any combination of the organic narrow medium ah... decane in the present embodiment is preferably the abe-deficient formula (1) in the above formulas (1) to (3). Ol^a/ (b+c The value of a/ and '(n ^ ^ fr ^ ^ rs JU C) of the above formula (1) is determined by using the organic matter described later and the hardness of the cured product of the resin composition. The above is better, and the hawthorn is made of heat-resistant yellowing and light-resistance. It is preferably 5 or less. The steam-soil is long and long. » Again, from this point of view, the range of h * a ° is preferably 0.12 or more. 4 or less 'better range is 0 · 15 or more 3 ^ . 0 from below, organic polymerization of this embodiment Thereof. Specific examples of the alkoxy radon bait as silicon can be cited as the speed of 27 201 247 745 323 923

323923 28 201247745

(16) 323923 29 201247745

323923 30 201247745

•(19) 323923 31 201247745

•••(21) 323923 32 201247745

323923 33 201247745

323923 34 201247745 R1 λ R1 R1 R1 R1 R1 R1 〆>,

(H2) ^R1 R1 (Hza1-9 PH2 -Si-R1 R1 R1 R1 R1 R1 R1 R1 :1 R1 〇R1 R1 \/ / \/,yTys\ R1 ,R1 "R1 (2

R2 I Y

323923 35 (26) 201247745

323923 36 201247745

323923 37 201247745

• (3) In the above general formulae (13) to (31), m represents an integer of 〇 to 2〇〇〇; η represents an integer of 0 to 20; and r represents an integer of 〇 to 2〇. In the case of light-resistance, it is preferred that R is a methyl group from the viewpoint of light resistance; and from the viewpoint of reactivity, those in which the above-mentioned is a propyloxy group or a methyl propyloxy group are Good; from the raw material::: point, the above Y is the side of the _4 ★ Chen Ben embodiment of the organic poly-exotherm, the above formula (1) contains (four) decyloxy (four) a glycerol It is preferable that it is 210 g/mol or more from the viewpoint of heat-resistant yellowing and light resistance of the cured product of the curable resin composition of the organic condensate resin composition of Organic 38 201247745, which will be described later; From the viewpoint of hardness, it is preferably 2000 g/mol or less. From this viewpoint, the functional group equivalent of the acryloxy group or the mercaptopropenyloxy group is preferably 250 g/mol or more and 1500 g/mol or less, and 3 Å. 〇g/mol or more l〇〇〇g/mol or less is more preferable. Further, the functional group equivalent of the propylene methoxy group or the fluorenyl propylene methoxy group may be according to the examples described later. The method for measuring the weight average molecular weight of the organopolysiloxane of the present embodiment is based on the thermal shock resistance of the cured product of the curable resin composition of the organopolysiloxane described later. 7 〇〇 or more is preferable; from the viewpoint of hardness, '5,000,000 or less is preferable, 1 〇〇〇 or more and 3 〇〇〇〇〇〇 or less is more preferable, and 1500 or more of loooooQ is more preferable. Further, this embodiment is Organic polyoxyalkylene, from the viewpoint of the viscosity of the organic polyoxyalkylene at f ° C from the viewpoint of the dispersion stability of the phosphor and the coloring agent, preferably 5 〇 mPa · s or more; In terms of 1500 mPa.

The following is better.

, after the [organic poly 11 oxygen 9 manufacturing method] s or more 10000OmPa · s

'Hydrogenated polyoxane (a2) of the hydrogen atom of the original thousand is a direct bond U2), 39 201247745 i) having two or more direct bonds to the following formula (11) a vinyl group-containing vinyl polyorganosiloxane (b1) of a halogen atom or a polyoxyalkylene (b2) having two or more hydroxyl groups directly bonded to a halogen atom, and ii) having two or more molecules The addition reaction of the unsaturated compound (c) of the unsaturated bond is carried out in the presence of a catalyst of the argon argonation reaction (d).

R1 in the above formula (11) represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group and a substitution. Or any one selected from the group consisting of unsubstituted aralkyl groups; j represents an integer of 1 or more; k represents an integer of 0 or more; and j+k represents an integer of 3 to 20. An example of the hydrogenated polyoxyalkylene (al) having at least one SiH group in one molecule represented by the above formula (11) is as shown in the following formula (32), (33) or (34). Compound. 201247745

3 3

CH-sio-H 3 4 3 The above-mentioned ιι化聚钱烧(al) may be two or more kinds of crude persons or one single type. σ is an example of "1 or more of the polysulfide U2 which is directly bonded to a hydrogen atom of a halogen atom", and may be as follows: (35), (36), (3) or (38) The compound shown.

I H 3C—Si—CH3 ch3 0 ch3 Η* —Si—Ο—Si—Ο—Si—Η

I I I 3 5 ch3 ch3 ch3 ch3 ch3

H—Si—0—Si—H 3 6)

I I ch3 ch3 323923 41 201247745

H H3I—HH3 c—si —c H3IH3 c o c1-1-1-Η——s′——ο——s——ο——s——H I I I c oic Η H - Η H clsi丨 c 7 3

_3 c LH3 H—silc I 3C H 8 , having one or more hydrogenated polyoxyalkylenes directly bonded to a hydrogen atom of a halogen atom, combining the above (al) with the above (a2) in an arbitrary ratio, that is, The hardness and gas barrier properties of the cured product and the viscosity of the curable resin composition containing the organic polyoxyalkylene of the present embodiment can be adjusted. When the ratio of the above (al) is increased, the hardness and gas barrier properties of the cured product can be increased, and when the ratio of the above (a2) is increased, the curable resin composition containing the organopolysiloxane of the present embodiment can be reduced. The viscosity makes the operation easy. The organic polyfluorene oxide (bl) having two or more ethylene groups directly bonded to the above-mentioned fluorene atom may be exemplified below. For example: CH2=CHSi(Me)2〇-Si(Me)2CH=CH2, CH2=CHSi(Me)2〇-Si(Me)2〇-Si(Me)2CH=CH2, 323923 42 201247745 CH2=CHSi( Me)2〇-(Si(Me)2〇)2-Si(Me)2CH=CH2, CH2=CHSi(Me)2〇-(Si(Me)2〇)3-Si(Me)2CH=CH2 CH2=CHSi(Me)2〇-(Si(Me)2〇)6-Si(Me)2CH=CH2, CH2=CHSi(Me)2〇-(Si(Me)2〇)8-Si(Me) 2CH=CH2, CH2=CHSi(Me)2〇-(Si(Me)2〇)"-Si(Me)2CH=CH2, CH2=CHSi(Me)2〇-(Si(Me)2〇)i2 -Si(Me)2CH=CH2 > CKHSi (Me)2〇-(Si(Me)2〇)2〇-Si (Me)2CH=CH2, CH2=CHCH2Si (Me)2〇-Si (Me)2CH2CH =CH2 and CH2=CHCH2Si(Me)2〇-Si(Me)2〇-Si(Me)2CH2CH=CH2. In the above formula, Me represents a fluorenyl group. The organopolyoxane (bl) having two or more vinyl groups directly bonded to a ruthenium atom may be used alone or in combination of two or more kinds. The polyoxanene (b2) having two or more hydroxyl groups directly bonded to the above-mentioned ruthenium atom can be exemplified as follows. For example: H〇*~Si(Me)2〇-Si(Me)2-〇H, H〇-Si(Me)2〇-Si(Me)2〇-Si(Me)2-OH, -Si (Me)2〇-(Si(Me)2〇)2_Si(Me)2-0H, H〇-Si(Me)2〇-(Si(Me)2〇)3-Si(Me)2-〇H , H〇-Si(Me)2〇-(Si(Me)2〇)6-Si(Me)2-〇H, H〇-Si(Me)2〇-(Si(Me)2〇)8_Si ( Me) 2-〇H, H〇-Si(Me)2〇-(Si(Me)2〇)"-Si(Me)2-〇H, H〇-Si(Me)2〇-(Si( Me) 2〇) i2-Si(Me)2-〇H, H〇-Si(Me)2〇-(Si(Me)2〇)2〇-Si(Me)2-〇H. 323923 43 201247745 In the above formula, Me represents a fluorenyl group. There may be two or more combinations of the above-mentioned (four) sub-groups, and may be a combination of two or more kinds, or may be an organic compound having two or more unsaturated bonds in the above one molecule. ) ' is as shown in the following formula (39). Ch2=ch—r3-r2 (39 2 to 1〇 contains an unsaturated bond. In the above formula (39), R 2 represents a carbon number group, and R represents a divalent nicotine group having 1 to 8 carbon atoms. In the following, the carbon number of the hydrogen group R3 can be surely carried out in a particularly favorable manner by 1 to 4. In another aspect, when R3 is 4 or less, the point of the Buddha can be suppressed, so that the above-mentioned reaction solution can be left ( c) The organic compound (c) ' having two or more unsaturated bonds in the above-mentioned one knife may be a combination of two or more kinds, or may be a single species. The organic polyoxane of the present embodiment. In the production step, the amount of the organic compound (c) having two or more unsaturated bonds in the i molecule (mole amount) is determined by reacting to the last point without leaving the SiH group, with respect to: a molar amount of a SiH group derived from the hydrogenated polyoxyalkylene (al) represented by the above formula (u) and a source of more than one or more hydrogen atoms directly bonded to the above-mentioned helium atom The sum of the molar amount of the SiH group of the hydrogenated polyoxyalkylene (a2) and the vinyl group having two or more directly bonded to the above-mentioned stone atom Vinyl organopolyoxyalkylene (bl) ethylene 323923 44 201247745 base molar amount or having more than 2 groups of fluorene (b2) based on the ruthenium atom directly bonded to the ruthenium atom The difference between the quantities, ie, the molar amount of the SiH group of ((al) SiH base + (a2)), the molar amount of vinyl of ((匕1) or (b2) The molar amount of the hydroxyl group is preferably added in excess.

Specifically, it is [the molar amount of the organic compound (c) having two or more unsaturated bonds in one molecule] / [(the molar amount of the SiH group derived from (al), (a2))_( The molar amount of the ethyl group derived from (bl) or the molar amount derived from the base of (b2) is preferably 1.2 to 3.0. The above-mentioned hydrazine hydrogenation catalyst is not particularly limited, and any of the known species can be used. For example, platinum black, chlorinated acid, chloroplatinic acid, a product of reaction of chloroplatinic acid with a monohydric alcohol, a complex of chloroplatinic acid and an olefin, a platinum bis(acetonitrile) acetate, etc. (4); 'Monetary catalysts, etc., are catalysts based on platinum group metal catalysts. (d)' may be a combination of two or more', or the hydrogenation catalyst may be used alone. The hydrazine hydrogenation catalyst (the amount of & shown in the formula (11) is not particularly limited, and is directly bonded to the polyoxyalkylene (al) and the re-containing content as needed.

Ca2), a hydrogenated polyoxane having a hydrogen atom of 2 atoms and a vinyl group-containing organic polyfluorene &amp; the above-mentioned ethyl group bonded directly to the ruthenium atom to the hydroxy group of the Shixi atom _bl), or having more than two direct bonds to more than one unsaturated bond, _ = (b2) and ii) having 2 3 mers in 1 molecule; compound r 323923 < C )' obtained by addition reaction 45 201247745 The weight of the organic polysulfide of the product is preferably from 〇〇1 to (10). The amount of the above-mentioned catalyst for the hydrogenation of the catalyst (4) is preferably from the viewpoint of sufficiently obtaining the effect of the direct addition, on the sense of mGlppnm; and from the viewpoint of cost, it is preferably from 100 ppm or less. At the same time, the "derivative reaction catalyst (4) may be removed by an adsorption material such as activated alumina or activated carbon after the addition reaction. From the viewpoint of heat-resistant yellowing and light resistance, the amount of the catalyst (4) to be described later is argonized (four) Wei (8) represented by the above formula (ι) with respect to _ mass parts, and Hydrogenation of a hydrogen group containing a samarium atom directly bonded to a hydrogen atom of a shixi atom (4) oxy-sinter (a2), phantom) and having more than 2 direct-bonding atoms of a vinyl group-containing organic poly-stone-oxygen (bl), or an organic compound (C) having two or more organic bonds (C) having a direct bond to the atomic group (tetra) and a ruthenium) The organic polyoxyalkylene is preferably 0.001 parts by mass or less. The amount of the hydrazine hydrogenation catalyst (d) in the curable resin composition can be measured by analyzing a curable resin composition described later. The above-mentioned addition reaction in the production step of the organopolyoxane of the present embodiment is generally from room temperature to 1 Torr. (: The reaction is carried out. When the above R2 is a (fluorenyl) acryloxy group, the (meth) propylene fluorenyl group has a possibility of colloidal reaction at a high temperature, and the reaction temperature is 4 〇 ° C to 7 〇 °c is preferred. The above addition reaction can also be carried out in a solvent as required. § In the case of hexane solvent, for example, aromatic phthalocyanine 323923 46 201247745, such as toluene and diphenylbenzene, can be used. An aliphatic solvent such as an alkane or an octane; a ketone solvent such as methyl ethyl ketone or methyl isobutyl ketone; an ester solvent such as ethyl acetate or isobutyl acetate; diisopropyl ether and 1,4-dioxin; An ether solvent such as an alkane, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether or propylene glycol monomethyl ether acetate; or an alcohol solvent such as isopropyl alcohol; or a mixed solvent thereof. The environment in the addition reaction may be any one of air and inert gas, and in the point of less coloring of the obtained organic hydrogenated polyoxyalkylene, in an inert gas such as nitrogen, argon or helium. Preferably, when the above R2 is a (meth) propylene decyloxy group, the poly(oxy) decyloxy group is prevented from being aggregated. For the purpose of the reaction, a small amount of oxygen may be introduced. When the above R2 is a (meth) propylene oxime group, in order to prevent the polymerization reaction of the (meth) propylene oxime group, the morphine is added to the reaction towel in advance. It is preferred to use a compounding agent such as a compound, an amine compound or a compound such as a compound. The type and amount of the polymerization inhibitor are not hindered by the addition of the material to prevent the progress of the hydrogenation reaction. The (meth)propoxy group, that is, the polymerization reaction of acryloxy or methacryloxy group, is not particularly limited. ' After the addition reaction, the reaction mixture is also The addition reaction catalyst can be removed by a general method such as water washing or activated carbon treatment, and the organic compound (c) having two or more unsaturated bonds in the remaining one molecule and the solvent can be heated and/or reduced. By press-removing, (1) F1 and ( (ii) F1 and Τ, 323923 47 201247745 (iii) FI of the constituent units F1, Μ1, and τ represented by the above formulas (1) to (3), An organic polyoxane of any combination of M1 and Τ In the embodiment of the present invention, the following anti-seam is prepared, and the anti-seam is added to the anti-seam, and the above-mentioned addition reaction can be carried out in advance (4). The sub-synthesis reaction catalyzes the above-mentioned hydrogenation material. (al) and according to the reaction liquid oxygen crater (10)' and the organic polyfluorination core containing the above ethylene group: an organic compound having two or more unsaturated bonds in two molecules and two or more directly bonded to the above stone The organic compound having two or more unsaturated bonds in the sulfonium, eight, and one molecules of the holly atom is further produced by the organic polyoxy siloxane of the present embodiment: the above-described addition reaction in the step C can be carried out sequentially In the first stage and the second stage, the first stage is to preliminarily prepare the hydrogenated polyoxane (al) containing the hydrogenated polyoxane (a2) and two or more molecules in one molecule. The reaction solution of the unsaturated compound (c) of the unsaturated bond is further added to the reaction solution by adding a catalyst for denitrification (d) to form the above-mentioned hydrogenation polymerization; e-oxygenation (a) &gt; Polyoxane (a2) and organic having 2 or more unsaturated bonds in one molecule a step of adding an adduct of the compound (c); a second pb ^ system, adding the vinyl group-containing organic polyoxo oxo to the reaction liquid, or having two or more directly bonded to the above ruthenium atom The step of the hydroxy group of the dream oxygenation (b2). [Curing Resin Composition] (Thermal Radical Generating Agent) The thermosetting resin composition of the present embodiment is 323923 48 201247745. The so-called organic polyoxane and the thermal radical generating agent are as described. A thermosetting resin composition. The above-mentioned thermal radical generating agent is not particularly limited as long as it can radically polymerize a (mercapto) acryloxy group by heat. For example, an organic peroxide such as benzoquinone peroxide, laurel, oxidized third butane, isopropyl hydroperoxide; azobisiso; azo compound such as nitrile. Specific examples thereof include 2,2-azobis(4-methoxy-2,4_-dimethylvaleronitrile) (V-70, manufactured by Nippon Wako Pure Chemical Industries, Ltd.), 2, 2 - _ Oxygen bis(2,4-dioxyl valeronitrile) (v-65, manufactured by Nippon Wako Pure Chemical Industries, Ltd.), 2' 2 -azobisisobutyronitrile (v-6 〇, Nippon Wako Pure Chemical Co., Ltd.) (manufacturing) and 2'2&gt;-azobis(2-mercaptobutyronitrile) (^59, manufactured by Nippon Wako Pure Chemical Co., Ltd.), etc.; octanoic acid peroxide (pER〇YL 〇, Japan Oil Company) Manufactured, oxidized laurel (PEROYL L, manufactured by Nippon Oil & Fats Co., Ltd.), oxidized stearin (pER0YL s, manufactured by Nippon Oil & Fats Co., Ltd.), peroxy succinic acid (PEROYL SA, manufactured by Nippon Oil & Fats Co., Ltd.)醯 (NYPER BW, manufactured by Nippon Oil & Fats Co., Ltd.), isobutyl hydrazine peroxide (PEROYL IB, manufactured by Nippon Oil & Fats Co., Ltd.), oxidized _2, 4 _ 2 gas, and sputum (NYPERCS, manufactured by Nippon Oil & Fats Co., Ltd.) and peroxide _ 3,5,5-trimethylhexanide (PEROYL 355, manufactured by Nippon Oil & Fats Co., Ltd.), etc.; di-n-propyl peroxydicarboxylate (pER〇YL Npp_5〇M, manufactured by Nippon Oil & Fats Co., Ltd.), diisopropyl peroxydicarboxylate (pER〇YL ϊρρ_5〇, manufactured by Nippon Oil & Fats Co., Ltd.), peroxidized di-bis(4_t-butylcyclohexyl)ester (PEROYL) TCP's manufactured by Nippon Oil & Fats Co., Ltd., dicarboxylic acid dicarboxylic acid II 323923 49 201247745 Ethoxyethyl ester (PEROYLEEP, manufactured by Nippon Oil & Fats Co., Ltd.), di-2-ethoxyhexyl peroxydicarboxylate (PEROYL 0PP, Nippon Oil & Fats Co., Ltd. Manufactured, di-2-oxobutyl peroxydicarboxylate (PEROYLMBP, manufactured by Nippon Oil & Fats Co., Ltd.) and bis(3-indolyl-3-indolyl butyl) peroxydicarboxylate (PEROYL S0P, Peroxydicarboxylates, etc. manufactured by Nippon Oil & Fats Co., Ltd.; hydrogen peroxide third butane (PERBUTYL H-69, manufactured by Nippon Oil & Fats Co., Ltd.) and peroxy-1,1,3,3-tetradecylbutane (? 跗 ^^11, manufactured by Nippon Oil & Fats Co., Ltd.) Hydroperoxides, etc.; Dibutane peroxide (PERBUTYL D, manufactured by Nippon Oil & Fats Co., Ltd.), 2, 5-dimethyl-2, 5- Bis(t-butyl peroxy) hexane (PERHEXA25B, manufactured by Nippon Oil & Fats Co., Ltd.) Class; α,α'-bis(new ruthenium peroxide) diisopropylbenzene (DYPERND, manufactured by Nippon Oil & Fats Co., Ltd.), isopropenyl peroxypimelate (PERCUMYL ND, manufactured by Sakamoto Oil Co., Ltd.), peroxidation Neodecanoic acid-1,1,3,3-tetramethylbutyl ester (PEROCTA ND, manufactured by Nippon Oil & Fats Co., Ltd.), peroxy neodecanoate-1-cyclohexyl-1-methylethyl ester (PERCYCLO ND, Nippon Oil & Fats Co., Ltd. Manufactured), perhexyl neodecanoate (PERHEXYL ND, manufactured by Nippon Oil & Fats Co., Ltd.), perbutyl neodecanoate (PERBUTYL ND, manufactured by Nippon Oil Co., Ltd.), trimethylacetate peroxide Ester (PERHEXYL PV, manufactured by Nippon Oil & Fats Co., Ltd.), tributyl succinate (PERBUTYL PV, manufactured by Sakamoto Oil Co., Ltd.), peroxy-2-ethylhexanoic acid-1, 1, 3, 3-tetramethyl butyl ketone (Technology (^^0, manufactured by Nippon Oil & Fats Co., Ltd.), 2,5-dimercapto-2,5-bis(2-ethylhexylperoxy)hexane (PERHEXA 250) , manufactured by Nippon Oil & Fats Co., Ltd.), pervaporated 2-ethylhexanoic acid-1-cyclohexyl-1-methylacetic acid (PERCYCL0 0 'made by Nippon Oil & Fats Co., Ltd.), Peroxy-2-B Third hexyl hexanoate 323923 50 201247745 (PERHEXYL 0, manufactured by Nippon Oil & Fats Co., Ltd.), tert-butyl peroxy-2-ethylhexanoate (PERBUTYL0, manufactured by Nippon Oil Co., Ltd.), third butyl peroxybutyrate Ester (PERBUTYL IB, manufactured by Nippon Oil & Fats Co., Ltd.), hexyl isopropyl monocarboxylate (PERHEXYL I, manufactured by Nippon Oil & Fats Co., Ltd.) and tert-butyl peroxymaleate (PERBUTYL MA, Japanese fat) Made by the company), triamyl peroxy-2-ethylhexanoate (Trigonox 121, manufactured by Akzo Co., Ltd.), third amyl peroxy-3,5,5-tridecylhexanoate (Kayaester) AN, an organic peroxide such as a peroxyester, etc., which is manufactured by Akzo Co., Ltd., etc., is not particularly limited thereto. The thermal radical generating agent may be used singly or in combination of two or more. The content of the thermal radical generating agent is more than 100 parts by mass of the hydrogenated polyoxoxane (al) represented by the above formula (11) and, if necessary, more than one hydrogen atom directly bonded to the halogen atom of the halogen atom. The hydrogenated polyoxyalkylene oxide (a2) and i) have two or more vinyl group-containing organopolyoxanes (bl) directly bonded to the above-mentioned fluorene atom, or have two or more direct bonds to The organic polyfluorene of the present embodiment of the above-mentioned addition reaction of the organic compound (c) having two or more unsaturated bonds in one molecule of the above-mentioned group The oxane is preferably 5 to 10 parts by mass. When the content of the thermal radical generator is 0.5 part by mass or more, the curable resin composition and the cured product having excellent heat-resistant yellow denaturation can be obtained. From this viewpoint, the content of the thermal radical generating agent is preferably 1 part by mass or more and 8 parts by mass or less, more preferably 2 parts by mass or more and 5% by mass or less. 323923 51 201247745 (Photo-radical generating agent) / The curable resin composition of the human body, one of the embodiments, and the resin composition of the above-mentioned organic polysiloxane and photo-radical generating agent. The ruthenium-deuterated olefin photo-radical generating agent' is not particularly limited as long as it is a species which can be photo-activated. Specific examples thereof are as follows: Japanese Patent Publication No. 59_1281, Japanese Patent Publication No. 61-9621, and Japanese Patent Publication No. 6G-6G1G4 have been carried out; In the Japanese Patent Publication No. Sho 43-23684, Japanese Patent Publication No. Sho 44_6413, Japanese Patent Publication No. 44-6413, and Japanese Special Public Show, Japanese Patent Publication No. Sho. The diazonium compound described in the specification of U.S. Patent No. 3, 567, 453, and the specification of U.S. Patent No. 2,848,328, the specification of U.S. Patent No. 2,852,379, and the U.S. Patent No. 2' The organic azide compound described in each of the specification sheets of 940'853; Japanese Patent Publication No. Sho 36-22062, Japanese Patent Publication No. Sho 37-131〇9, Japanese Patent Publication No. Sho 38-18015, and Japanese Special Public Show 45%二 化合物 化合物 化合物 二 二 二 二 二 二 二 二 二 二 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 Page (1977 The arsenic compound described in Japanese Laid-Open Patent Publication No. Hei 59-142205, Japanese Laid-Open Patent Publication No. Hei No. Hei. Metallic heavy olefins described in European Patent No. 1, 851, 323, 923, 52, 2012, 477, 245, European Patent No. 126, No. 712, and "J. Imag Sci., Vol. 30, p. 174 (1986)" (Side oxy) oxime (such as 丨丨 “ 有机 有机 有机 有机 ; ; ; ; 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 61 In the "Coordination Chemistry Review, Vol. 84, No. 85 (277) (1988)" and "Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. a transition metal complex of a transition metal such as ruthenium; a 2,4,5-triarylimidazole dimer described in JP-A-3-209477; carbon tetrachloride and a special opening in Japan 59_1〇 Organic i-based compounds described in 'No. 7344'. These species can be used alone or in groups. Two or more kinds of use: The content of the photoradical generator is directly bonded to one or more of the hydrogenated polywei (al) represented by the above formula (11) with respect to 1 part by mass. The hydrogenation of the hydrogen atom of the upper atom "oxygen" (U2), and i) the organic group (M) having two or more ethylene groups directly bonded to the ethylene group of the above-mentioned stone atom, or having 2 fine An organic compound having two or more f-saturation bonds in the i molecule described above, which is directly bonded to the group of the above-mentioned shixi atom, (the present invention) The organic poly 11 New Zealand is preferably Q. 5 to 2q parts by mass. When the content of the photoradical generator is 0.5 parts by mass or more, it is possible to obtain a curable tree residue and a cured product which are excellent in light resistance when they are excellent in the amount of (4). From this point of view, it is preferable that the content of the base-generating agent is from 0.1 part by mass to 15 parts by mass or less. Quality 323923 53 201247745 More than 10 parts by mass or less. (Other components) The curable resin composition of the present embodiment may be added with (meth) propyl sulphate for the purpose of promoting the curability (enhancement of sensitivity) to energy such as heat and ultraviolet rays. A radical polymerizable compound such as a vinegar monomer or an oligomer or a vinyl (meth)acrylate. Further, additives such as an anti-aging agent, a mold release agent, a diluent, an antioxidant, a heat stabilizer, a flame retardant, a plasticizer, and a surfactant may be added within the range of quantity and quality without departing from the scope of the present invention. . In addition, the hardening resin composition of the second embodiment may further contain an inorganic material such as stone or an organic material such as a synthetic resin. Organic poly, step 2 = Γ) Above:; = Γ atomic gasification of the grain (10), and. Organic polyoxygen (bl): the vinyl-containing vinyl substrate of the sub-ethylene compound should be re-formulated with the antimony (c) by the addition reaction to form a metal molecule, which has a surface, a resin, etc. The formation of the organic material and the recombination of the fine compound group or the organic material miscibility 3 1 j are not particularly limited. 54 201247745 The above can form an oxy group and an ethoxy group with an inorganic material. The reactive group of the bond may be, for example, a reactive group which forms a chemical bond with an organic material, and may be exemplified by ethylene, &amp;oxyamino group, methacrylic group, propyl acetophenate, thiol group, Isocyanate groups and the like. The substituent which is excellent in miscibility with the organic material may, for example, be an isomeric cyanate group. Specific examples thereof include vinyltrimethoxysilane (KBM-1GG3' manufactured by Shin-Etsu Chemical Co., Ltd.), ethylene-triethoxylate (KBE-1003, manufactured by Shin-Etsu Chemical Co., Ltd.), and 2 (3, 4-epoxycyclohexyl)ethyldimethoxydecane (KBM-303, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldimethoxydecane (KBM_4〇2, manufactured by Sakamoto Shin-Etsu Chemical Co., Ltd. , 3-glycidoxypropyltrimethoxy decane (KBM_4〇3, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldiethoxy decane (KBE-402, manufactured by Shin-Etsu Chemical Co., Ltd.) , 3_glycidoxypropyl triethoxy decane (KBE-403, manufactured by Shin-Etsu Chemical Co., Ltd.), p-styrene trioxoxane (KBM-1403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-mercaptopropene oxime Oxypropyl decyl dioxin (KBM-502, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropyltrioxane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-A Acryloxypropyl fluorenyldiethoxy decane (KBE-502, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-曱Acryl propyloxypropyl triethoxy decane (KBE-503, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-propenyl methoxypropyl trioxoxane (KBM-5103, manufactured by Shin-Etsu Chemical Co., Ltd.), N-2-( Aminoethyl)-3-aminopropylmethyldioxanane (KBM-602, manufactured by Shin-Etsu Chemical Co., Ltd.), N-2-(amineethyl)-3- 323923 55 201247745 Aminopropyltrimethoxy decane ( ΚΒΜ-603, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-aminopropyltrioxane (ΚΒΜ-903, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-aminopropyltriethoxysilane (ΚΒΕ-903, Japan Shin-Etsu Chemical Co., Ltd. Manufactured, 3_triethoxylated _3_Ν_(1,3-didecyl-butylene) propylamine (ΚΒΕ-9103, manufactured by Shin-Etsu Chemical Co., Ltd.), Ν-phenyl-3-aminopropyltrioxane Hydrane (ΚΒΜ-573, manufactured by Shin-Etsu Chemical Co., Ltd.), Ν-(vinylphenylhydrazino)-2-amineethyl-3-aminopropyltrioxoxane hydrochloride (KBM-575, Shin-Etsu Chemical Co., Ltd. Manufactured by the company, 3-ureidopropyl triethoxy decane (KBE-585, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-arylthiopropyl decyl dioxin (KBM-802, Japan Letter) Manufactured by Yue Chemical Co., Ltd., 3-Hydroxythiopropyltrioxane (KBM-803, manufactured by Shin-Etsu Chemical Co., Ltd.), bis(triethoxyphosphoryl) tetrasulfide (KBE-846, manufactured by Shin-Etsu Chemical Co., Ltd.) , 3-isocyanate propyl triethoxy decane (KBE-9007, manufactured by Shin-Etsu Chemical Co., Ltd.), tris-(3-trioxalylhydryl propyl) isocyanurate (X-12-965, Shin-Etsu, Japan) It is manufactured by a chemical company, etc., but is not limited thereto. Further, these decane coupling agents may be used singly or in combination of two or more. The content of the decane coupling agent in the curable resin composition of the present embodiment is preferably 0.5 to 10 parts by mass based on 100 parts by mass of the organopolysiloxane. When the content of the stagnation coupling agent is 0.5 parts by mass or more, the adhesion is excellent, and when it is 10 parts by mass or less, the heat resistance yellowing resistance is good. From this point of view, the content of the decane coupling agent is preferably 0.7 parts by mass or more and 8 parts by mass of 323923 56 .201247745 parts or less, more preferably 1 part by mass or more and 5 parts by mass or less. The hardening property of the present invention is based on the fact that in the step of the addition reaction of the organic poly(four) calcination, the (4)7 hydrogenation catalyst may be contained with respect to 1 g of the mass of the catalyst. 0. 001 parts by mass or less. The Lithium Hydrogenation Catalyst (4), as described above, can be removed by an active oxidation-deficient carbon or the like after the addition reaction of the organic polysulfide. The content of the (4) shixi hydrogenation catalyst is preferably from 5% by mass or less, more preferably 5% by mass or less, more preferably from 0.005 parts by mass or less, from the viewpoint of resistance to yellowing and light resistance. The curable resin composition of the present embodiment is used in the organic t-stone hospital towel of the present embodiment to improve heat yellowing, light resistance, hardness, conductivity I&quot; heat conductivity, and thixotropic (th1X0 opy). For the purpose of low thermal expansion and the like, a filler represented by an inorganic oxide may be contained as needed. Examples of the filler include cerium oxide (fumed silica, gelaphthalmic oxide (c〇11〇idal (6)), and precipitated oxidized stone), and tantalum nitride. Inorganic oxides or inorganic nitrides such as boron nitride, aluminum oxide, cerium oxide, titanium oxide and barium titanate, glass, ceramics, silver powder, gold powder and copper powder. The filler can be used with or without surface treatment, and when subjected to surface treatment, the fluidity of the curable resin composition can be increased, and the filling ratio can be increased, which is industrially preferable. Examples of the surface-treated particulate inorganic filler may be as follows: oxime oxidation, trimethyl hydrazide, octopine, or eucalyptus oil treatment. 323923 57 201247745 The content of the inorganic oxide in the curable resin composition of the present embodiment is preferably from &quot; to the mass part based on 100 parts by mass of the organic polyoxalate. [Cured material] The curable resin composition of the present embodiment is liquid or solid before curing, and can be formed into a cured product by a predetermined treatment. For example, when the above-mentioned thermal radical generator is contained in the curable resin composition, the cured product can be obtained by heat treatment. The temperature is generally from 100 to 250 ° C. The hardening method and molding method of the curable resin composition are not particularly limited. When the curable resin composition is in a liquid state, it can be shaped by, for example, molding, low pressure transfer molding, potting, dipping, press molding, and injection molding. When the curable resin composition is in a solid form, it can be molded by heating and hardening under pressure using, for example, an extruder or a low-pressure transfer molding machine. The cured product of the curable resin composition of the present embodiment is also suitable for use as a sealing material for an optical semiconductor device. Further, the curable resin composition of the present embodiment can also be used as a wafer bonding paste, and the cured product can be used as a wafer bonding material. Further, the cured product of the curable resin composition of the present embodiment is also suitably used in the use of a light semiconductor device such as a coating material or a lens material around the coated wafer. In this case, the optical semiconductor may be, for example, a led lamp, a wafer type LED, a semiconductor laser, an optical coupler, and an optical diode. 323923 58 201247745 The photo-semiconductor material (4) of the curable resin composition of the present embodiment has the above-mentioned photo-forming material as a structure: an outer shell material, a sand wafer provided in the outer shell material, and &gt; The cured product of the curable resin composition is not particularly limited as a material for sealing the above-mentioned outer casing material in the above two:: ', for example, an aromatic polyamine such as *benzamide; 66 nylon, etc. In the case of polypyridylamine, it is particularly useful to exhibit a high-adhesive plastic. In addition to the glass fiber, the outer casing of the outer casing can further improve the strength of the joint. The content of the above glass fiber is preferably from 5 to 40% by mass, more preferably from 1 to 3 % by mass, particularly preferably from 15 to 5% by mass. When the content of the glass fiber is within this numerical range, the adhesion can be more markedly exhibited. As described above, in the case where the curable resin composition of the present embodiment is cured in a liquid state or in a solid state by a predetermined photoradical generator, the cured product can be produced by wire irradiation. In the case where the photo-radical generator is formulated, the curable resin composition is also suitable for use as a coating material for a resin film, a substrate or the like which is required to be rapidly cured without heating. For example, it can be used as a coating material for forming an antireflection film which is used in a flat panel display (FPD) or the like. In particular, when used as the coating material for forming an antireflection film, it is preferable to form a cured film having a refractive index of 1.4 or less, and the curable resin composition preferably contains porous fine particles which form voids. 323923 59 201247745

The porous fine particles may be oxidized cerium particles having an average particle diameter (four), and the cerium oxide particles having 5 to (10) M == are preferable from the viewpoint of the penetration of the cured film. Specific examples are, for example, the hydrophilicity of the vending product or the hydrophobization treatment of the surface material~(10)...trade name, manufactured by Japan Aerosil Co., Ltd.) and the pearl chain of the gasification shixi particle in a straight chain (4) sol "SN_XPS" (trade name: Japan Nissan Chemical Co., Ltd.). The porous fine particles are preferably used in a range of from 1 Torr to 1 part by mass based on the total amount of the porous fine particles of the curable resin composition of 1 (10) parts by mass, and the uniformity of the curable resin composition is uniform. Dispersion is better. When the curable resin composition of the present embodiment is used as a coating material, the method for forming the cured film may be, for example, a transparent substrate (such as polymethyl methacrylate, polycarbonate, polystyrene, and tris). The surface of the acetaminophen resin substrate or the glass-specific inorganic material is coated with a coating material containing the curable resin composition of the present embodiment, and the coating film is further photocured to form an antireflection film and A method in which the thickness of the protective film or the like is from 1 〇 nm to 硬化Am. When coating on a substrate, it is necessary to form a thin film with high fineness. At this time, it can be used: micro gravure coating method, roll coating method, shower coating method, spin coating method, rigid mold coating method, and extension flow. Coating method and spraying method. The curable resin composition ' may be diluted with a solvent or the like for adjusting the viscosity as needed, or may be in the form of a sol containing porous fine particles or the like. When it is used for dilution with a solvent or the like, and when it is used in a sol form containing porous fine particles or the like, the solvent component is volatilized in advance, and it can be heated at 5 Torr to 323,923, 60, 2012, 477, and 150 ° C for about several minutes before curing. Further, a coloring agent is added to the curable resin composition of the present embodiment, that is, it can be a curable ink. As the coloring agent described above, various organic pigments and inorganic pigments can be used. For example: white pigments such as titanium oxide, zinc white, lead white, zinc antimony and antimony oxide; black pigments such as nigrosine, iron black and carbon black; chrome yellow and yellow iron oxide 'Hansa yellow (100, 50) , 30, etc., yellow pigments such as titanium yellow, petroleum ether yellow and permanent yellow; orange pigments such as Chrome Vermilion, permanent orange, Vulcan Fast Orange; iron oxide, permanent brown and Brown pigment such as brown; red iron oxide, cadmium red, enamel sand, permanent red, rose red, S plain, sulphur red, PV carmine, Monolight red and quinacone red Red pigments such as pigments; purple violet, manganese violet, permanent violet, methyl violet, indosin, bright purple, and purple violet pigments; ultramarine, Prussian blue, blue, blue hall, Blue pigments without metal phthalocyanine blue, copper sapphire blue, indanthrene blue, indigo, etc.; chrome green, chrome oxide, emerald green, naphthol green, golden green, acid green lake, peacock green lake, 酞Green pigments such as cyanine green and polybrominated copper arsenic; other various fluorescent pigments, metals Powder pigments and body pigments. The amount of the coloring agent is preferably from 1 to 50% by mass, more preferably from 5 to 25% by mass, based on the total amount of the curable resin composition. The pigment can also be used as a pigment in the hardenable ink. Examples of the pigment dispersant include higher fatty acid salts, alkyl sulfates, alkyl ester sulfates, decyl sulfates, trans-salt salts, naphthalene acid 323923 61 201247745 salts, The activation of salt, polyoxygen (4) hetero-salt, polyoxy-phenylene phenyl ether, glycerol s, sorbus red-like β-mimi-ester and polyoxyethylene fatty decylamine is activated by styrene, stupid ethylene derivatives, a copolymer of a vinyl naphthalene derivative, an acrylic acid, an acrylic acid derivative, a diacid derivative, an itaconic acid = a cannic acid derivative, a transbutyric acid, and a fumaric acid derivative, or a random copolymer The copolymer and the dispersion method of the coloring agent in the hardened ink can be exemplified by using a mill, a sand mill, an attritor, a roll mill, a mixer, a Henschel mixer, a rubber mill, and a super A method of various dispersing machines such as a sonic homogenizer, a bead mill, and a wet nozzle powder oscillating machine. Further, the predetermined treatment can be carried out by using a centrifuge or a filter for the purpose of removing coarse particles of the pigment dispersion in the curable ink. When the pigment ink is used as the above coloring agent, the average particle hollow of the pigment particles in the pigment ink is selected in consideration of stability, image density, glossiness, light resistance, etc. in the curable ink, and is increasing. From the viewpoint of gloss and texture improvement, it is preferred to appropriately select the average particle diameter of the pigment particles. The curable resin composition of the present embodiment exhibits heat-resistant yellowing and high transparency, and is suitable for use in spectacle lenses, optical device lenses, CD and DVD reading lenses, automotive headlight lenses, and projectors. The material of the lens such as a lens is used for various optical member materials such as an optical fiber, an optical waveguide, a filter, an optical adhesive, a disk substrate, a display substrate, and a curable resin for nanoimprint. The curable resin composition of the present embodiment can be used as a first semiconductor 323923 62 201247745 sealing material, which is a cured product which is suitable for use as a transparent resin for a semiconductor package, and the above-mentioned optical semiconductor sealing material can be obtained by molding. body. The sealing material for an optical semiconductor is applied to a workpiece subjected to a base film treatment after plasma treatment, and is directly applied by a coating device such as a dispenser or a rotary dispenser. The coated optical semiconductor sealing material can be cured or cured by a molding machine or the like. [Examples] Hereinafter, the present invention will be specifically described by way of Examples and Comparative Examples, but the present invention is not limited to the examples below. In the examples and comparative examples, the measurement and evaluation were carried out in the following manner. &lt;(1) Calculation of Reaction Rate of SiH&gt; A sample reaction solution of 0.05 g (i.e., a reaction solution in the synthesis of an organopolyoxane in the examples and comparative examples described later), 72 hours after the start of the reaction The solution was dissolved in lg of a gas-like imitation solvent as a measurement sample. Then, the measurement sample was subjected to iH NMR measurement at a cumulative number of times at 4 〇〇 MHz (manufactured by JASCO Corporation, α-400), and the results of the measurement were analyzed. The reaction rate of the SiH was determined by calculating the area ratio of the peak of 0.2 ppm from Si-CH3 and the peak of 4. 6 ppm from SiH before and after the reaction, and then calculated according to the following formula. After that, when the reaction rate of SiH is 98% or more, it is ©, 90% or more, and 323923 63 201247745 is 〇 when it is less than 98%, and χ when it is less than 9%.

Reaction rate of SiH = [

XI . g pain against U1~Y1) /XI]xlOO X1 · Peak area ratio of reaction (peak area of Siii before reaction) / 彳5 temple &amp; area) dry / (Si-CIL peak before reaction) Y1 ·· Peak area ratio after reaction (peak area of SiH after reaction) / (peak area of si-CH3 after reaction) &lt; (2) Determination of molecular structure> Relative to 20 mg, examples and comparisons described later The sample of the organic hydrooxane (A1) to (A17) produced in the example was dissolved in a deuterated gas in a ratio of ig as a measurement sample, and the measurement sample was manufactured by JASCO Corporation. The α _4 进行 was measured by iH nmr in the cumulative number of times 200 times, and the result of the analysis was analyzed. The solution dissolved in the oxime gas agent at a ratio of lg was used as a measurement sample with respect to the sample of 〇.3 g. The measurement sample was subjected to % 疋' reanalysis measurement by α_400 manufactured by the Japanese division in a cumulative number of 20,000 times. The gas was dissolved in the gas and the respective agent at a ratio of 1 g with respect to the sample of ^. And add 8 相对 relative to the siloxane

A solution of Cr(aCac)3 was used as the ruthenium sample. Further, with the measurement sample, α_4〇〇 manufactured by Knife Co., Ltd. of 里/〇 was measured by the cumulative number of times 4〇〇〇2, and the result of the measurement was analyzed. _ After that, the molecular structure of (H1 NMR, 丨3C NMR, 29Si Nmr 323923) t 201204545 = Γ = = (Α1) to (Al7) is analyzed. (3) Calculation of Functional Group Equivalent of (Mercapto) Acryloxy Group> The organic-based gas-like solution (4) liquid prepared in the comparative example of 30 mg of the above-mentioned bismuth-oxygen (8) to (A17) As a result of the dissolution of the atmosphere after the manufacture of the Japanese spectrophotometer, the sample was determined, and the analysis was carried out. The average composition of the knot was 200 times. 1 molecule = one sample for 0.15g The 8th (fourth) heart of the oxysonic gas is used for the measurement of the sample. Then, the sample is measured by the sputum, the sputum is divided into ΓΓ400, and the cumulative number of times is 4,000 times. The result of the analysis of the heart is determined by the organic (tetra) oxy-burning scorpion. After the average group, the results obtained by one side and one% of the households were analyzed and calculated (the functional equivalent of the methoxy group of the thiophene (the mass per i mole of the functional group). &lt; (4) Calculation of the weight average molecular weight &gt; ^ With respect to 100 mg of the sample for measurement of the organopolyoxane (A1) to (A17) prepared in the examples and the comparative examples described later, it was dissolved in a chloroform solvent at a ratio of 0.45. Filtration of βπι filter membrane as a sample solution. Re-column temperature 4 (TC, dissolved The flow rate of the liquid (chloroform) is imL/min, and the column (the structure of the column is used to protect the column using the Tskguard column Η hour-H (registered by 323923 65 201247745) manufactured by Sakamoto Tosoh Corporation). Tskgel (registered trademark) G5000H hour manufactured by Tosoh Corporation of Japan and Tskgel (registered trademark) G3000H hour manufactured by Sakamoto Tosoh Corporation, Tskgel (registered trademark) G1000H hour manufactured by Tosoh Corporation of Japan In addition, the molecular weights of 7,500,000, 2,560,000, 841, 700, 320,000, 148,000, 59, 500, 28, 500, 10, 850, 2, 930, 580, which are manufactured by Polymer Laboratories, are previously prepared. The molecular weight monodisperse polystyrene standard and the styrene monomer (molecular weight 104) were determined by RI to determine the calibration curve of the elution time. Then, the elution time and the detection intensity of the sample solution were measured, and the molecular weight was calculated from the calibration curve. &lt;(5) Measurement of Viscosity> Samples for measurement of organopolyoxane (A1) to (A17) produced in Examples and Comparative Examples described later, manufactured by Nippon Seiki Co., Ltd. Manufactured as TVE-22H, the viscosity at a temperature of 25 ° C was measured. (6) The content of the compound represented by the formula (10) [WB] relative to the content of the compound represented by the formula (9) [WA] Calculation of ratio ([WB]/[WA])> Values of [WA] and [WB] are matrix-assisted free time-of-flight mass spectrometry using organopolysiloxanes (hereinafter referred to as MALDI-TOF/MS) The intensity of the peak corresponding to the mass of each of the structures conforming to the general formulae (9) and (10) and the mass of the nanomass 23 is measured. In addition, the mass of each structure conforming to the general formula (9) and the general formula (10), when the constituent elements of the above structure have an isotope, means that the existence ratio is the highest within the mass of the isotope of each element. The value calculated for the mass of the isotope. 323923 66 201247745 A compound having the structure of the general formula (9) and a compound represented by the formula (1〇) when a plurality of peaks of the general formula (9) and the general formula (10) are present at the same time The content [WB], each line corresponds to the total value of the peak intensity of the structure. However, the maximum intensity of the peak corresponding to the mass of each of the structures conforming to the general formula (9) and the general formula (1) and the total mass of the sodium mass 23 has a peak intensity of 3% or less, and is calculated. The sum of the peak intensities is excluded. The measurement method of MALDI-TOF/MS was carried out in the following manner. &lt;Measurement Method of MALDI-T0F/MS&gt; The organopolysiloxane produced in the examples and the comparative examples described later in O.lg is 5), (human 6), (411) at room temperature. And (412) a solution of tetrahydrocyanate dissolved in 1 Torr, and a solution of 1 〇mg of Di thrano 1 dissolved in 1 mL of tetrahydrofuran at room temperature in a volume ratio: 1 ratio is uniformly mixed into a solution, followed by 1; i / L in a test dish of 1 〇 mg of sodium iodide dissolved in 1 mL of acetone and then dropped into 1 eL of solution a' After evaporating the solvent at room temperature, the measurement of MALDI-TOF/MS was carried out under the following measurement conditions. (Measurement conditions) Device: Japan Shimadzu Corporation AXIMA CFR plus Laser light: Nitrogen laser light (337nm) Detector form: Linear ion detection: Positive ion (positive ion type) Cumulative number: 500 times 323923 67 .201247745 &lt; (7 Heat-resistant yellowing property> The cured product produced in the examples and the comparative examples described later is a sample for measurement, and a cured product having a thickness of 3 mm is used, and a spectrophotometer CM-3600d manufactured by Konica Corporation of Japan is used. Name) Determine its γι (yellowness). Next, 'the cured product was coated with aluminum foil and heat-treated at 150 ° C for 150 hours in the air', and then measured by a spectrophotometer CM-3600d (trade name) manufactured by K〇nica-Minolta Co., Ltd., Japan. Γι (yellowness). Among them, the change in Y1 before and after the heat treatment was ΔΥ1, and it was evaluated that ΔΥ1 was less than 1.0, ◎, 1.0 or more and less than 3.0 were 〇, and 3.0 or more was χ. &lt; (8) Light resistance> The cured product produced in the examples and the comparative examples described later is a sample for measurement, and a cured product having a thickness of 3 mm is used, and a spectrophotometer CM manufactured by Konica-Minolta Co., Ltd., Japan is used. 3600d (trade name) measures its Y1 (yellowness). Next, the cured product was placed in a constant temperature dryer set to 50 ° C, and then a UV irradiation device (manufactured by Sakamoto Ushio Electric Co., Ltd., trade name: SP-7) equipped with a 365 nm band pass filter. Irradiation at 365 nm with an illumination of 4 W/cm 2 for 1 hour. Thereafter, the Y1 (yellowness) was measured again by a spectrophotometer CM-3600d (trade name) manufactured by Konica-Minolta Co., Ltd., Japan. The change in enthalpy before and after uv irradiation is ΔΥ1 ’. ΔΥ1 is less than 1.0, and 1.0 or more and less than 3.0 is 〇, and 3.0 or more is X. 323923 68 201247745 &lt; (9) Cold and thermal shock resistance> The outer shell of the molded body of a polyphenylene amide resin (AModel 4122 manufactured by s〇lvay Co., Ltd.) having a groove of 1 mm in depth at a center of a plate of 20 mm x 20 mn ix 2 mm 5mmx5mmx0. 2mm stone lithium wafer is arranged in the material. Next, 'the cured resin composition prepared in Examples 1 to 17 and Comparative Examples 1 to 6 is injection molded', and then heated or photohardened to form a cured product (sealing material) of the sealed stone wafer, thereby obtaining an optical semiconductor. Test of the device The test piece obtained was further observed by a small thermal shock device TSE-11 manufactured by Espec Corporation of Japan at room temperature to -40 ° C (15 minutes) to 1203⁄4 (15 minutes) to room temperature for 1 cycle. The number of times until the peeling occurs is 0. If the peeling does not occur in 100 cycles or more, the peeling is ©, and the peeling occurs when 50 or more and less than 100 times. When the number is less than 50, the person who produces the peeling is X ° &lt; 10) Hardness&gt; The cured product produced in the examples and the comparative examples described later is a sample for the preparation of the sample, which is a cured product having a length of 35 mm x a width of 8 mm and a thickness of 2 mm, and is measured by MCR-301 manufactured by AntAn Parr Co., Ltd., Japan. Dynamic viscoelasticity at -120 ° C to 150 ° C (temperature increase rate 2 ° C / min). The hardness is 30 ° C (the value of storage modulus), when it is 1〇7 or more, it is ©, when it is 1〇6 or more and below 107, it is 〇, and when it is less than 1〇6, it is χ. 11) Adhesiveness> In the model of a polyphthalamide resin (AModel 4122 manufactured by S〇ivay Co., Ltd.) in which a groove of ΙΟπιηΐφ, a depth of 323923 69, and 201247745 lmra was provided in the center of a 20 mm×20 mm×2 mm plate, Example 1 was 17. The curable resin composition prepared in Comparative Examples 1 to 6 was injection molded, and then subjected to heating or photohardening to obtain a test piece. The obtained test piece was further used as a small thermal shock device TSE-11 manufactured by Espec Corporation of Japan. From room temperature to _4 〇〇 c (15 minutes) to i2 〇 cc (15 minutes) to room temperature for 1 cycle, the number of times until peeling occurred was visually observed. The detachment occurred in 100 cycles or more. When 50 or more and less than 100 times, the peeling is 〇, and when it is less than 50 times, the peeling is X ° &lt; (12) Gas barrier properties> The cured products prepared in the examples and comparative examples described later are measured. Use the sample 'use a thickness of 〇. 2mm l〇〇mmxi〇〇mm hardened material to Systech The oxygen transmission rate measuring device M〇del 8001 manufactured by Illinois Japan Co., Ltd. measures the oxygen permeability at a temperature of 23 ° C under dry conditions. When the oxygen transmission rate is less than 500 cc/m 2 /day, it is ◎, 5 〇〇 cc / When m2/day or more and less than l00 cc/mVday, it is 〇, and l〇〇〇cc/mVday or more is parent. [Example 1] &lt;Organic polyoxyalkylene (A1) having a group containing an unsaturated bond Manufacture &gt; In a 3-neck retort of 3. 〇L equipped with a stirring device, a thermometer, and a reflux condenser, 53 g (0.2 mol) of 1,3,5'7-tetraindole as the (al) component was added. Base ring tetraoxane, 27 § (〇.1 mole) as the (32) component of methyl tris(dimethyl methoxy) decane, 242 g (〇. 3 mole) for 323923 70 201247745 for ( The bl) component is a polydimethylsiloxane having a weight average molecular weight of 780 as shown in the following average composition formula (B1-1), and a vinyl dimethoxy end group of 101 g (0.9 mol) (c) component of 6-vinylbicyclo [2.2.1] hept-2-ene, 1600 g of terpene and 0.05 g of hydroquinone monoterpene ether (polymerization inhibitor), stirred under nitrogen and simultaneously heated to 60 ° C. C H2=CHSi(Me)2〇-(Si(Me)2〇)8-Si(Me)2CH=CH2.. (B1-1) wherein, in the above average composition formula (B1-1), Me represents 曱The basis is the same in the average composition formula shown in the examples and comparative examples in the present specification. ). Thereafter, a chloropropanoic acid isopropanol solution was added to make the weight of the metal to the organic polyoxoflame of the addition reaction product to be 2 ppm. After confirming the start of the rhodium hydrogenation reaction, the reaction system was kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. After analyzing the contents of the steamed bottle, it was found that the reaction rate of the S i thiol group was 98%. Thereafter, the activated carbon treatment is carried out to distill off the volatile component, whereby 350 g of an organic polyoxosiloxane (A1) having an unsaturated bond group represented by the following formula (40) can be obtained. The obtained unsaturated polyether-containing organopolyoxane (A1), which does not contain (mercapto) acryloxy group, has a functional group equivalent of 694 g/mol of an unsaturated bond group, as determined by GPC The calculated weight average molecular weight was 37,500, and the viscosity at 25 ° C was 2,800 mPa · s. 323923 71 201247745

•••(40) In the above formula (40), m represents an integer of 10 on average; η represents an integer of 8 in average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -17.2ppm

Ml: + 8.8ppm T : -66.2ppm D2 : -19.8ppm D3 : -21.2ppm a/ ( b+c ) has a value of 0.78. However, no peak of S: -32. 3ppm was observed; the value of d/a was zero. &lt;5 parts by mass of peroxy-2-ethylhexyl group in an organic polyoxyalkylene (A1) 323923 72 201247745 containing 100 parts by mass of an unsaturated bond-containing group The acid tertiary amyl ester (manufactured by the Japanese chemical company Akzo Co., Ltd., trade name: Trigonox 121-50E, 50% by mass solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was poured into a frame model made of SUS316, and the hardened material was obtained by curing at 100 ° C for 4 hours and at 150 ° C for 1 hour. The evaluation results of the obtained cured product characteristics are shown in Table 1 below. [Example 2] &lt;Production of a mercapto propylene oxy group-containing organopolyoxane (A2)&gt; In a 3.0 L retort equipped with a stirring device, a thermometer, and a reflux condenser, 53 g (0.2 mol) of 1,3,5,7-tetradecylcyclotetraoxane as an (al) component, and 27 g (0.1 mol) of a sulfhydryl group (a) as a component (a2) Oxy)decane, 242 g (0.3 mol) of a polydifluorenyl group having a weight average molecular weight of 780 as shown in the following average composition formula (B1-2) as a component (bl)矽 烷 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 118 Stir and simultaneously warm to 60 °C. CH2=CHSi(Me)2〇-(Si(Me)2〇)8-Si(Me)2CH=CH2. (B1-2) After that, add isopropyl alcohol solution in isopropyl alcohol to make the starting metal, The weight of the organopolyoxane relative to the addition reaction product was 20 ppm. After confirming the start of the rhodium hydrogenation reaction, the reaction system was incubated and maintained at 55 to 65 ° C with water cooling or air cooling at 323923 73 • 201247745 while stirring for 72 hours. Thereafter, the contents of the distillation flask were analyzed, and the reaction rate of the SiH group was found to be 99%. Thereafter, the activated carbon treatment is carried out to distill off the volatile component, whereby 370 g of the mercaptopropenyloxy group-containing organopolyoxane (A2) represented by the following formula (41) can be obtained. The obtained mercaptopropenyloxy group-containing organopolyoxane (A2) had a functional group equivalent of 714 g/mol, a weight average molecular weight calculated by GPC of 38,200, and a viscosity at 25 ° C of 2,600 mPa·s.

In the above formula (41), m represents an integer of 1 平均 on average; n represents an integer of 8 in average.

As a result of Si NMR measurement, a peak represented by the following 323923 201247745 which is equivalent to the constituent unit was observed. F1 : -18. 2pPm Ml : +8. 8ΡΡ® T : -66. 2pPffl D2 : -19.8pPm D3 : -21. The value of 2pPm a/ (b+c) is 〇. 78. 0, but a peak of S. -32. 3ppm is observed in the same place; d/a &lt;manufacturing and characteristics of the hardened material s are determined> in 100 parts by mass of the methacryloxy group containing methoxy group (A2) 2. 5 parts by mass of peroxy-2-ethylhexanide = oxazane. The chemical is manufactured by Akzo, trade name: Trig〇n〇x 12^酉(曰曰畺% solution) under milk 〉 Kunming, the mixing is carried out so that 50 can be defoamed to obtain a hardenable composition. After the Danshishi, the sclerosing sputum was injected into the frame model of _16, and the hardened material was obtained by looking for 4 hours and then 15 〇ΐ 丨 。. 1 W tearing hardening reaction, the result Evaluation of the properties of the cured product [Example 3] * As shown in Table 1 below. &lt;Lv: base (10) decyloxy organic material Oxygen (Α3) is distilled with a stirring device, a thermometer, a reflux condenser 3. The muscle 3 3 3 5 7 ~ A ^ ^ ^ (〇. 2 Moer) as (5)) The composition of the 323923 component of the four (^ four dreams, Moer) as (10) (-W gas base) Wei 2G3g (〇. 3 mole) as the (1) 75 201247745 component, as shown in the following average composition formula (B1-3), the weight average molecular weight of 780 is the vinyl dimethyl methoxy end of the polydimethyl hydrazine. Oxysilane, 118 g (0.9 mol) of methacrylic acid-3-butenyl ester as component (c), 1500 g of fluorene benzene and 0.05 g of hydroquinone monoterpene ether (polymerization inhibitor), stirred under nitrogen And simultaneously heated to 60 ° C. CH2 = CHSi (Me) 2 〇 - (Si (Me) 2 〇 ) 8 - Si (Me) 2 CH = CH 2 · · (B1-3), after adding chloroplatinic acid Isopropanol solution to make platinum metal relative to addition The weight of the organic polysulfide of the product to be formed was 2Oppm. After the start of the hydrogenation reaction, the reaction system was kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. Then, the content of the retort was analyzed, and the reaction rate of the SiH group was 97%. Then, after the activated carbon treatment and the volatile component were distilled off, 330 g of the ruthenium represented by the following formula (42) was obtained. Alkyloxy alkoxy-organopolyoxyalkylene (A3). The obtained functional group equivalent of the mercaptopropenyloxy-containing organopolyoxane (A3) is 626 g/mo, and the weight average calculated by GPC The molecular weight is 34,200, and the viscosity at 25 ° C is 3500 mPa · s. 323923 76 201247745

X

HjC

-/ i, (JJ, 〆•~CHj V HjC〆, 〆? ! v ί 于, 丨X! a «i \/ y . VW, 〇) rsN. 0-1, H2C. H#, ./ λ/'

r\ H into haa: called -0 &quot;vww, 1 {^C /Hz ΐ / ,)~ H b '"vOdc^C,; 〆一tC HlC-SI-CH3 -«, »3^Γ2 Ηβ , household ^f), Hac^ ), n (Ah2 'produced * v, ΓΗν'々-γΐ?Ό:sj/.Vv^^sv^csCI \_/4s^^xhy Η^ί), -( salty r ^ 兮 '/CH3 h'/Ch3h: • - (42) In the above formula (42), m represents an integer of 5; and n represents an integer of 8 on average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 · -18.2ppm Ml : + 8.8ppm D2 : -19.8ppm 323923 77 201247745 D3 : -21. 2pPm S : -32.3pPra a/ (b+c) The value is 丨· 08 ; The value of d/a is 〇 · 〇8. &lt;Manufacturing and Characterization of Hardened Material&gt; 2.5 parts by weight of pervaporized _2-ethylhexanoic acid in the mass part of the methyl propyl-oxy group-containing organic polyoxo (A3) The third pentaacetic acid (manufactured by Akzo Co., Ltd., trade name: Trig〇n〇x 121_pass, 5〇 mass% solution) is mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain hardening. Sexual composition. The composition of the middle bismuth compound is injected into the framework model of the 6th system, and the cured product is obtained at 4C for 4 hours and then at 15 minutes. ', hardening reaction at the time' Evaluation of the obtained cured product [Example 4] The following shows the following. &lt;organic polycondensation containing acryloxy group in the assembly «mixing device, warm material, (four) condensation 1-, one ring four is:), the composition of the composition such as T-single-form (called) _ 86... Stir under benzene and _ while heating to 6 generations. After the nitrogen is present, 3% 923923 CH2, Si(Me)2(Ksi(Me)2〇)8_Si(Me)2CH, 2. . . (bh) 78 201247745, add the gas-alcoholic isopropanol solution to make the metal The weight of the organic polyoxygenator relative to the addition reaction product was 2 ppm. After confirming the start of the rhodium hydrogenation reaction, the reaction system was kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. After analyzing the contents of the steamed bottle, it was found that the reaction rate of the S i thiol group was 99%. Thereafter, the activated carbon treatment is carried out to distill off the volatile component, whereby 205 g of the mercaptopropenyloxy group-containing organopolyoxane (A4) represented by the following formula (43) can be obtained. The obtained mercaptopropenyloxy group-containing organopolyoxane (A4) had a functional group equivalent of 600 g/mol, a weight average molecular weight calculated by GPC of 19,800, and a viscosity at 25 ° C of 4,500 mPa·s.

•••(43) In the above formula (43), m represents an integer of 15 on average; η represents an integer of 8 in average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -18.2ppm 323923 79 201247745

Ml: + 8.8 ppm D2: -19.8 ppm D3: -21.2 ppm a/ (b+c) has a value of 13.13. However, no peak of S · -32. 3ppm was observed; the value of d/a was 〇. 5质量份的氧化氧乙乙酸的第第5质量份的乙乙乙乙酸酸Triamhyl ester (product name: Trigonox 121-50 Ε, 50% by mass solution manufactured by Akzo Co., Ltd.) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was injected into a frame model made of SUS316 to obtain a cured product by 10 (4 hours at TC and then at 150 ° C for 1 hour). The obtained cured product was evaluated. The results are shown in the following Table 1. [Example 5] &lt;Production of a methacryloxy group-containing organopolyoxane (A5)> A stirring apparatus, a thermometer, and a reflux condenser were used. In 3L 3, '68g (G 3 mole) is added as a component of (al)·component, such as Si Shi Xi Oxygen, 51 “°. 3 Moh” (bi) The molecular weight of the formula (β1_5) is dimethyl oxalate of the oxy group at the end of the U6, 11% of the methacrylic acid butyrate of 〇.9 benzene and 0 〇, 795 After the .4 氲腼 monomethyl ether (polymerization inhibitor), stirred under nitrogen atmosphere and 323923 201247745 simultaneously heated to 6 ° ° c reaction CH2 = CHSi (Me) 2 〇 ^ Cs.ru χ y UMe) 2 〇)8-Si(Me)2CH=CH2. . . (Bl-5) ', the isopropyl alcohol solution of the gas-storing acid, the weight of the organic poly-burning of the metal with respect to the addition reaction is 2Gppm The amount of After the start of the reaction, the reaction was kept warm and kept at 55 to 653⁄4 with water or air cooling while stirring for 72 hours. After analyzing the contents of the distillation flask, the reaction rate of the siH group was 99%. Further, after the activated carbon treatment and distillation of the volatile component, 188 g of the fluorenyl-containing fluorenyloxy group represented by the following formula (44), the following formula (45), and the following formula (46) can be obtained. The organopolyoxyalkylene (A5). The obtained methacryloxy-containing organopolyoxane (A5) has a functional group equivalent of 350 g/mol, and the weight average molecular weight calculated by GPC is 16,400,25. The value of [WB]/[WA] of the obtained methacryloxy group-containing organic polyfluorene oxide (A5) is 1.7. Further, the formula (45) ) corresponds to the formula (9) ' The formula (46) corresponds to the formula (1).

323923 • · (44) 201247745

In the above formula (44), m represents an integer of 25; and η represents an integer of 0.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 · -18.2ppm Ml : + 8.8ppm D2 : -19·8ppm a/ (b+c) The value is 1. 04. However, no peak of S: -32. 3ppm was observed; the value of d/a was zero. 5质量份的氧化氧化乙乙酸酸的。 The mass of the methacryloxy-containing organopolyoxane (A5) in an amount of 2.5 parts by mass of peroxy-2-ethylhexanoic acid Triamyl ester (曰323923 82.201247745 manufactured by Akzo Co., Ltd., trade name. Quality. Solution) is mixed under air gas, and = _Χ121-pass is passed, and 50 is defoamed to obtain a curable composition. After the whole is made, the cured composition is obtained by injecting the curable composition into a coffee bean, 10 10 ° ° CT 4 , J &gt; a $ &gt;# 15 15 , ± . In the case of C, the hardening reaction was carried out, and the evaluation results of the obtained cured product characteristics are shown in the following Table i. [Example 6] <Production of organopolyoxyalkylene (A6) containing methacryloxyloxy group> In a steaming crane bottle equipped with a sputum, a thermometer, and a reflux condenser, 201 g (0.8 mol) of the (al) component is represented by the following average composition formula (B1_6), which is a component of (4) 莫 (4) 乍 (8)). a polydimethylsiloxane having a vinyl dimethoxy end group having a molecular weight of 186, 97 g (0.7 mol) of a methacrylic acid _3-butenyl ester as a component (c), and 2i38 g of toluene and 0. 05g of hydroquinone monomethyl ether (polymerization inhibitor), stirred under nitrogen atmosphere and simultaneously heated to 60 ° C reaction. CH2=CHSi (Me)2〇~(Si (Me)2〇)8_Si (Me)2CH=CH2· ·. (B1_6) Then add 'Ig platonic acid in isopropanol solution to form platinum metal relative to addition reaction The weight of the organic polyoxane of the substance is 2 〇 ppm. After the start of the helium gasification reaction was determined, the reaction system was kept warm and kept at 55 炱 65 ° C with water cooling or air cooling while stirring for 72 hours. Thereafter, the contents of the distillation flask were analyzed, and the reaction rate of the SiH group was found to be 99%. 323923 83 201247745 After that, after the activated carbon treatment and distillation of the volatile component, 520 g of the methyl group represented by the following formula (47), the following formula (48), and the following formula (49) can be obtained. Alkyloxy-organopolyoxymethane (A6). The obtained mercaptopropenyloxy group-containing organopolyoxane (A6) had a functional group equivalent of 1157 g/mol, a weight average molecular weight calculated by GPC of 98,600, and a viscosity at 25 ° C of 26,000 mPa·s. The value of [WB]/[WA] of the obtained fluorenyl propylene oxy group-containing organopolyoxane (A6) was 10.1. Further, the formula (48) corresponds to the formula (9), and the formula (49) corresponds to the formula (10).

HaC I/

(47) 323923 84 201247745

'c/CH3 I P〆,

In the above formula (47), m represents an integer of 30 on average; n represents an integer of 0.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -18.2ppm Ml : + 8.8ppm D2 · -19.8ppm a/ (b+c) The value is 0.16. 323923 85 201247745 However, no S: -32.3 ppm peak was observed; d/a has a value of zero. &lt;Manufacturing and Characterization of Hardened Material> In 100 parts by mass of an organopolyoxyalkylene group containing a mercaptopropenyloxy group (2.5 parts by weight of a perylene-2-ethylhexanoic acid, a third amyl group) The product (trade name: Trig_x 1215〇Ε, 5〇 mass% solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to prepare a hard-shirt composition. Inject the 4 hardening composition into the frame model of the other $316, to 100. 〇: the next 4 small β main π. The temple, and then harden the reaction at 15 ° C for 1 hour to obtain the hardened material. The evaluation results of the properties of the cured product are as follows (Example 7) <Manufacture of organopolyoxyalkylene (A?) containing methacryloxyloxy group&gt; • Mounted with stirring agricultural, thermometer, reflux condenser 3. In the 3 bottles of the Luo Museum, add f η 1苜[, ! Q, 7 (0. 1 mol) as the (al) component of the 22nd: methyl ring Si Shixi Oxygen, 13g ( 〇·05 Moer) (10) :, earth (dimethoxy) decane and 0.1 g (0.002 mol) of tetradecane, U9g 9 # ή·, &gt;&amp;&amp; ^ Έ0 · Moer) as a (bl) component, as shown in the following sentence, K (BM), weight average bis- oxy end group, polydiphenyl ketone, 53 丄 2: as U) component (tetra)丙, 〇. 〇 5g of hydroquinone monomethyl ether "yang (four), 曰,,, and the heating to 6 (TC reaction. (d)), under nitrogen atmosphere (four) and at the same time CH2.Si (Me) Thai ( Si(Me)2〇)8_si(Me)2CH=cH2...(10)π 323923 86 201247745 Then, a solution of chloroplatinic acid in isopropanol is added to make the platinum metal with respect to the addition reaction product of the organic polysulfide The weight is 2Oppm. After determining the start of the hydrogenation reaction, the reaction system is kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. After analyzing the contents of the distillation bottle, it is known that The reaction rate of the SiH group is 99%. After that, the activated carbon is treated and the volatile component is distilled off to obtain 180 g of an organopolyoxyalkylene group having a mercaptopropenyloxy group represented by the following formula (50). (A7) The functional group equivalent of the obtained mercaptopropenyloxy group-containing organopolyoxane (A7) is 767 g/mol, which is calculated by GPC. The average molecular weight of the viscosity of the 189800,25 ° C 4500OmPa · s.

H3C CHaHjC CHjH^C CH3 H3\ H3C—Si—CH3 0H3C ch3 〜T,), 〆HAr ch3 h2 /\ l\ I\ h2 HaC CH^3C CHaHaC CH3

• -(50) 323923 87 201247745 In the above formula (50), '10 represents an integer of 5 Å on average; n is an integer of 8 each. τ

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 ·· -18. 2ppm

Ml : + 8.8ppm T : -66.2ppm D2 : -19.8ppm D3 : -21·2ppm a/ (b+c) The value is 〇. 7〇. However, no peak of S: -32. 3ppm was observed; the value of d/a was 〇. &lt;Manufacturing and Characterization of Hardened Material&gt; ' 2.5 parts by volume of peroxy-2-ethylhexanoic acid in 100 parts by mass of methacryloxy-containing organopolyoxane (Α7) The saponin (manufactured by Akzo Co., Ltd., trade name: Trig〇n〇x 121, 5〇e, 5〇 mass% solution) is mixed under nitrogen, stirred to make the whole uniform, and then defoamed. A hardenable composition can be obtained. Then, the curable composition was poured into a frame model made of Qing 16 and the hardened material was obtained by performing a hardening reaction under the boots for 4 hours and then under the boots for 1 hour. Evaluation of the obtained cured product characteristics [Example 8] &lt;Production of organic (tetra)oxygen (A8) containing methyl (10) decyloxy group] 3. 0 L equipped with (iv) apparatus, thermometer, reflux condenser 3 323923 88 201247745 mouth retort, adding 53g (0.2 mol) 1,3,5,7-tetramethylcyclotetraoxane, 27\(〇^ as the constituent of the (31) component (dioxaoxy) decane, 235 mol) (a2) is a component of (b2), and the average molecular weight of the following is § § (〇·3 mol). The average molecular weight is 760 hydroxy dioxime = Bb8 ) shown as a flat burnt, 118g (0.9m) of polydiamine decyl butyl methacrylate, 1600g of toluene and 〇 · 〇 5g of methacrylic acid -3- in a gas atmosphere Stir and simultaneously heat to 6 $ early 曱 ( (polymerization inhibitor), HO-Si (Me) 2 〇 - (Si (Me) 2 〇) 8_Si (Me) 2 〇 H reaction. After that, a solution of the isoammonic acid of the chlorobutyric acid is added, and the organic polyoxane which is the reaction product is estimated to be added to the amount of the platinum metal after the start of the dehydrogenation reaction. . Cool or air-cooled at 55 to 65 ° C while stirring?; Department: temperature ' and after water analysis of the contents of the money ship, can be 96%. After the reaction rate of the thiol group, the methyl group represented by the following formula (9) is subjected to activated carbon treatment to distill off the oxime (A8). The organic polyglycol-containing organic poly-sand &amp; functional group equivalent of the obtained base is 7〇3g/mol, and the amount of jA8) calculated by GPC is 34,500, and the viscosity at 25〇C is 2500mPa . s.篁 average molecular 323923 89 201247745

In the above formula (51), m represents an integer of 10 on average; η represents an integer of 8 in average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -18.2ppm T : -66.2ppm D1 and D2 : -19.8ppm D3 · -21.2ppm S : -32.3ppm a/ (b+c) is 1.33; d/a is 0· 09 . 5质量份的氧化氧化乙乙酸酸3。 The mass of the thiol propylene oxy-containing organopolyoxane (A8) Amyl ester (曰323923 90 201247745, manufactured by Akzo Co., Ltd., trade name: Trigonox 121-50E, 50% by mass solution), mixed under nitrogen, stirred for uniformity, and then defoamed to obtain a hardenable composition. . Then, the curable composition was poured into a frame model made of SUS316, and the hardened product was obtained by performing a hardening reaction under ion: 4 hours and then for 15 hours. 1 is shown. <Manufacture of Organic Jujube (a9) containing A, Dilute Oxyloxy Group>

3 kinds of base distillation &amp; dish count, reflux condenser 3. 0L of 3 steaming 瑕, add 啕 ((). 2 Mo 5, 7, methyl ring four tender 3 (= U2) composition The average molecular weight t of 兀97S (0.3 mol) as the component (b2), and the weight of the butene vinegar of the formula (B1'9), l5GGg&lt;¥—the methacrylic acid-3 as the component (C) is cooled in a nitrogen atmosphere and the hydrogen roller monogram (G.Q5g) in the nitrogen atmosphere (polymerization inhibitor), and the .SUM phase is heated to the order reaction.

Sl(Me)Thai (Si (after, knowing the reserve Ue) 2'0H··. (B1-9) The reaction product is formed by the &quot;isopropanol money' fairy metal relative to the weight added to the C burnt Become the amount of 4〇_. Cold or air-cooled after the start of ^, the reaction system will be kept warm, and after the water is deducted two to 65 &lt; t, while stirring for 72 hours. 323923 steamed her contents, we know its The reaction rate of the SiH group is 977% in the amount of 201247745. Thereafter, after the activated carbon treatment and the volatile component are distilled off, 325 g of the organopolyoxyl group having a mercapto propylene oxy group represented by the following formula (52) can be obtained. Alkane (A9). The obtained organopolyoxyalkylene (A9) having a mercaptopropenyloxy group has a functional group equivalent of 617 g/mo. The weight average molecular weight calculated by GPC is 33,200, and the viscosity at 25 ° C. It is 3400 mPa · s.

•••(52) In the above formula (52), m represents an integer of 5; and η represents an integer of 8 in average. 323923 92 201247745

As a result of Si NMR measurement, "#. F1 : -18.2ppm T * -66.2ppm D3 : -21.2ppm S : -32·3ppm a/ (b+c) The value is i. 75 ; The value of d/a is 〇. 〇8. 5质量份的氧化氧乙乙酸酸的。 The mass of the methacryloxy-containing organopolyoxane (A9) in an amount of 2.5 parts by mass of peroxy-2-ethylhexanoic acid Triamyl ester (manufactured by Akzo Co., Ltd., trade name: Trig〇n〇x 12 Bu 5〇E, 5〇 mass% solution) is mixed under nitrogen, stirred to make the whole uniform, and then defoamed. A hardenable composition is obtained. Then, the curable composition was poured into a frame model made of SUS316, and the cured product was obtained at 4 ° C at 100 °C. J, hour, and further hardening reaction at 15 ° C for 1 hour [Example 10] The evaluation results of the obtained cured product characteristics are shown in Table 2 below. <Methyl propylene oxy group-containing organic polyhard Wei 〇) Manufacturing &gt;

93 201247745 Mole) as a component (c) of 3-butenyl methacrylate, 864 g of toluene and 0.05 g of hydroquinone monomethyl ether (polymerization inhibitor), stirred under nitrogen atmosphere and simultaneously heated React to 60 ° C. H0-Si(Me)20-(Si(Me)20)8-Si(Me)2-0H. ·. (B1-10) After that, add isopropyl alcohol solution in isopropyl alcohol to make the starting metal relative to the addition. The weight of the organic polyoxygenated product of the reaction product was 40 ppm. Immediately after the start of the dehydrogenation reaction, the reaction system was kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. Thereafter, the contents of the steaming bottle were analyzed, and it was found that the reaction rate of the S i thiol group was 96%. Thereafter, after the activated carbon treatment and distillation of the volatile component, 20 lg of the mercaptopropenyloxy group-containing organopolyoxane (A10) represented by the following formula (53) can be obtained. The obtained mercaptopropenyloxy group-containing organopolyoxane (A10) had a functional group equivalent of 591 g/mol, a weight average molecular weight calculated by GPC of 19,500, and a viscosity at 25 ° C of 4,200 mPa·s.

•••(53) 323923 94 201247745 In the above formula (53), 1 〇 represents an integer of 15 on average; n represents an integer of 8 in average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 * -18.2ppm T : -66.2ppm D3 : -21·2ppm S · -32.3ppm a/ (b+c) has a value of 113; d/a has a value of 〇 〇8. 5质量份的氧化氧乙乙酸的第第5质量份的乙乙乙乙酸酸的。 The mass of the methacryloxy-containing organopolyoxane (A10) in an amount of 2.5 parts by mass of peroxy-2-ethylhexanoic acid Triamyl ester (manufactured by Paeki Akz Co., Ltd., trade name: Trigonox 121-50E, 50% by mass solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was poured into a frame model made of SUS316 at 100 C for 4 hours, and then hardened by i5 (1 hour at TC) to obtain a cured product. The obtained cured product characteristics were evaluated as follows. [Table 11] [Example 11] &lt;Production of 3-methyl oxime-oxygenated organopolyoxane (All)&gt; The oxime was equipped with a stirring device, a thermometer, and a reflux condenser. 0L of 3 i 3,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, 477 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 Benzyl 3-butenyl ester, 795 g of hydrazine and 0.05 g of hydroquinone monoterpene ether (polymerization inhibitor), stirred under nitrogen atmosphere and simultaneously heated to 60 ° C. H〇-Si (Me)2〇-(Si(Me)2〇)8-Si(Me)2-〇H. . . (B1-11), then add chloroplatinic acid in isopropanol solution to make platinum metal relative to addition Reaction product The weight of the polyoxygen was 40 ppm. After determining the start of the dehydrogenation reaction, the reaction was kept warm and kept at 55 to 65 ° C with water or air cooling while stirring for 72 hours. The content of the SiH group was found to be 99%. Then, after the activated carbon treatment and the volatile component were distilled off, 183 g of the following formula (54), the following formula (55) and the following were obtained. The organopolyoxyalkylene (All) having a mercaptopropenyloxy group represented by the formula (56). The functional group equivalent of the obtained methacryloxy group-containing organopolyoxane (All) is 340 g/mol, the weight average molecular weight calculated by GPC is 17600, and the viscosity at 25 ° C is 1450 OmPa · s. [WB]/ of the obtained organopolyoxyalkylene (All) containing mercapto acryloxy group. The value of [WA] is 1.9. Further, the general formula (55) corresponds to the general formula (9), and the general formula (56) corresponds to the general formula (10).

η / . . . - (56) In the above formula (54), m represents an integer of 25; and η represents an integer of 0. 323923 97 201247745

The peak shown by the result of Si NMR measurement. It can be observed that the composition is equivalent to the following F1 · -18.2ppm T : -66. The value of 2ppm a/ ( b+c) is 1. 〇〇. However, it is not observed that S: - 3 2 q <The manufacturing and characteristics of the cured product are lower than the peak value of d'd/d; Manufactured in an amount of 2.5 parts by mass of an organic polyoxochemical compound Akzo Co., Ltd., containing 100 parts by mass of methicone (AU), commercial monoethylhexanoic acid third vinegar (daily mass%) The solution is mixed under nitrogen, and two = lg_121~50E' 50. The defoaming composition can be obtained by defoaming. &amp;, 'After the whole - after', and then the curable composition, the middle 1 · 1 1 , into the frame model made by SUS316

The cured product was obtained by using T M 100C for 4 hours and then J. The hardening reaction was carried out every hour, and the evaluation results of the obtained cured product [Example 12] are shown in Table 2 below. &lt;Production of methacryloxyl-containing organic ketone ketone oxane (A12)> In the assembly of the mixing plant, the field selection ^. λ summer, the meter, the reflux condenser. In the 0L of 3 σ distillation flask, add 2〇lg, . / 1 N ΛΑ V υ·8 mol) as the (al) component of I' 3' 5' 7-tetradecyl ring tetrahydroxane, 24 〇g (1. 4 mol) as the (b2) component, as shown in the following average composition formula (B 12), the molecular weight of 166 is dimethyl oxime (tetra) dimethyl di 11 nu (three).? Mohr) as the component (c), thiol-acidic acid _3_butene vinegar, 2l38g of benzene benzene 323923 98 201247745 and 〇.〇5g of hydroquinone monomethyl ether (polymerization inhibitor) Under the environment and simultaneously warm to 60 C reaction. H〇-Si(Me)2〇-(Si(Me)2〇)8-Si(Me)2^〇H (b (1) after adding 'isopropyl chloride solution of chloroplatinic acid, sigh' makes platinum metal relative to The weight of the organic polyoxane of the addition reaction product is &amp; ^ 叹 40 40 ppm. After determining the start of the dehydrogenation reaction, the e ^ reaction system will be kept warm and kept at 55 to 65 by water cooling or air cooling. °C, at the same time after searching for 72 丨, the contents of the retort were analyzed, and the reaction rate of the SiH group was 93%. After that, it was treated with activated carbon, distilled, and removed. Thus, 490 g of an organopolyoxyalkylene (M2) having a mercaptopropenyloxy group which is not represented by the following formula (57) and the following formula ( _ and the following formula (59) can be obtained. The molar energy average calculated by Gpc is 9 ' '25. (The viscosity is 咖 咖 pa s.) The ruthenium equivalent of ^(tetra)pyrene (10)) is l〇94g/mo. The organic propylene oxy group of the organic (four) city ((10) ventilating two: 9.6. And the general formula (58) corresponds to the general formula (4), and the general formula (59) corresponds to the general formula (1 〇). 323923 99 201247745

323923 100 201247745

η / . . . - (59) In the above formula (57), m represents an integer of 30; and η represents an integer of 0.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -18.2ppm T : -66. The value of 2ppm a/ (b+c) is 0.15. However, no peak of S: -32. 3ppm was observed; the value of d/a was zero. 5质量份的氧化氧乙乙酸的第第5质量份的氧化乙乙乙酸酸的。 The mass of the thiol propylene oxy group-containing organopolyoxane (A12) in an amount of 2.5 parts by mass of peroxy-2-ethylhexanoic acid Triamyl ester (manufactured by Akzo Co., Ltd., trade name: Trigonox 121-50E, 50% by mass solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was poured into a frame model made of SUS316, and the hardened material was obtained by curing at 100 ° C for 4 hours and at 150 ° C for 1 hour. 323923 101 201247745 The evaluation results of the obtained cured product characteristics are shown in Table 2 below. [Example 13] <Production of an organic polydecane (A13) containing a mercapto propylene oxy group> In a 3.0 liter retort equipped with a stirring device, a thermometer, and a reflux condenser, 24 g was added. (0. 1 mol) of 1,3,5,7-tetradecylcyclotetraoxane as an (al) component, and 13 g (0.05 mol) of a mercapto III as a component (a2) Dimethoxy) decane and O.lg (0.002 mol) of tetramethyl decane, 116 g (0.2 mol) of (b2) component, weight average molecular weight as shown by the following average composition formula (B1-13) 5克。 The hydroxy hydroxy hydroxy end of the polydidecyl fluorinated argon, 53g (0.3 m) of the component (c) as a component (c) methacrylate methacrylate, 768g of benzene and 0. 05g Hydroquinone monoterpene ether (polymerization inhibitor), stirred under a nitrogen atmosphere and simultaneously heated to 60 ° C reaction. HO-Si(Me)2〇-(Si(Me)2〇)8-Si(Me)2-OH. . . (B1-13) After that, add a solution of gas-acidic isopropanol to make the metal relative The weight of the organic polyoxoflame of the addition reaction product was 40 ppm. After the start of the deamination reaction was determined, the reaction system was kept warm and kept at 55 to 65 ° C with water cooling or air cooling while stirring for 72 hours. Thereafter, the contents of the distillation flask were analyzed, and the reaction rate of the SiH group was found to be 97%. Thereafter, the activated carbon is treated and the volatile component is distilled off to obtain 170 g of a mercaptopropenyloxy group-containing organopolyoxane (A13) represented by the following formula (60). The obtained mercaptopropenyloxy-containing organopolyoxane (A13) 323923 102 201247745 has a functional group equivalent of 756 g/mol, a weight average molecular weight calculated by GPC of 182100, and a viscosity at 25 ° C of 42300 mPa. · s.

•••(60) In the above formula (60), m represents an integer of 50 on average; η represents an integer of 8 in average.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 · -18.2ppm T : -66. 2ppm D3 : -21.2ppm S · -32. 3ppm a/ (b+c) has a value of 1. 25 ; d/a has a value of 0.10. 5质量份的氧化氧化-2-2 The oxidized product of the oxidized product of the methicone The third ester of ethylhexanoate (manufactured by the Japanese chemical company Akzo, trade name: Trigonox 121-50E, 50% by mass solution) is mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a hardenable composition. Things. Then, the curable composition was poured into a frame model made of SUS316, and the cured product was obtained by performing a hardening reaction at 100 ° C for 4 hours and at 15 ° C for 1 hour. The obtained cured product characteristics were evaluated as follows. [Table 14] [Production of &lt;Production of a mercapto propylene oxy group-containing organopolyoxane (A14)&gt; 3. A stirring device, a thermometer, and a reflux condenser were installed. In a 3-point steaming bottle, add 96g (〇·4 moles) of 1,3,5,7-tetramethylcyclotetraoxane as an (al) component, and 1〇7g (〇. 8m). The molecular weight of the fluorenyl-113,3-tetradecyldioxane as a component (a2) and 269 g (1.4 mol) as the component (bl) has a molecular weight of 186 as shown in the following average composition formula (B1-14). Vinyl dimethyloxy-terminated dimercaptodioxane, 97 g (0.7 mol) of methacrylic acid-3-butenyl ester as component (c), 2138 g of fluorene benzene and hydrazine. 05 g Hydroquinone monoterpene ether (polymerization inhibitor), scrambled under nitrogen atmosphere and simultaneously heated to 6 (TC reaction. CH2=CHSi(Me)2〇~(Si(Me)2〇)8-Si(Me ) 2CH=CH2·.. (B Bu 14) After 'Tian The isopropyl alcohol solution of gas platinum acid makes the weight of the platinum metal relative to the organic polyoxyalkylene of the addition reaction product to be 20 ppm. After determining the start of the hydrogenation reaction, the reaction system is kept warm, and is 323,923,104. 201247745 The water cooling is maintained at 55 to 65t, and the mixing is carried out for 72 hours. It is 99%. The content of the money bottle is π, and it can be known that the reaction rate of the (10) group is 52〇gh, and then treated with activated carbon to remove volatile components. Thus, an organopolyoxyalkylene (A14) having a methyl propylene oxide oxy group represented by the following formula (8) and the following formula (10): 520. The obtained methacryloxy group-containing organic polymer The functional group equivalent of the decane (A14) is 1300 g/mol, and the weight average molecular weight calculated by GPC is 11,000, and the viscosity at 25 Torr is 600 mPa. s. The obtained methacryloxy group-containing organic polyoxyl Alkane (AM), a hydrogenated polyoxoquinone containing at least a ruthenium (5) SiH group in one molecule of two raw materials = common (4) (al) and (a2). Therefore, the resulting 3 fluorene-based oxy-oxygen Based on the organic poly-stone hospital (A14 is low, and its viscosity is reduced. X (four) 4

323923 (61) 105 201247745

HaC

-CH3

In the above formula (61), m represents an integer of averaging 30; n represents an integer of 0; and r represents an integer of 0.

As a result of Si NMR measurement, a peak as shown below corresponding to the constituent unit was observed. F1 : -18.2ppm

Ml: + 8.8ppm D2: -19.8ppm F2: + 7. Oppm a/ (b+c) has a value of 0.16. However, no S: -32. 3ppm front was observed; the value of d/a was zero. 5质量份的氧化氧化乙乙酸酸的。 The propylene oxide oxy-containing organopolyoxane (A14) in an amount of 2.5 parts by mass of peroxy-2-ethylhexanoic acid Triamyl ester (manufactured by Akzo Co., Ltd., trade name: Trigonox 121-50E, 50% by mass solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was poured into a frame model made of SUS316, and the hardened material was obtained by curing at 100 ° C for 4 hours and at 150 ° C for 1 hour, and 323923 106 201247745. Each of the obtained cured product characteristics [Example 15] The results of the heart are as shown in Table 2 below. &lt;Methyl propylene oxy group-containing organic oxy-combustion (return to the first stage reaction) As the component (10) of the 1,3,5,7 rQ·2 isomol as the U1) component in the 31-piece retort of the falling device flow condenser: 1 base _ Wei, 27 g ( ; / ... Mo The ear) (4) into t 匕曱 欢 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The aerated alcohol solution of platinum gas is used to make the amount of oxygen in the platinum metal relative to the addition reaction (4) (4) into 2Gppra. After determining the start of the gasification reaction, the reaction system is kept warm and the water is cooled or air cooled. The reaction of the second stage is carried out in the reaction liquid of the above first stage, and 242 g (Q.3 mol) of bl (b. The weight average molecular weight is polydimethyl sulfide of the end of the dimethyl oxy group of the county, the reaction is pure temperature, and is kept at 55 to catch by water cooling or air cooling, and 72 hours are searched. After analyzing the contents of the steamed bottle, it can be seen that the reaction rate of the base is 99% 0, and then, after 1 reactive treatment, the volatile component is removed, and 360g of the following is obtained. (41) Organic 323923 107 201247745 oxoxane (A2) containing no methacryloxy group. The s-energy group of the organopolyoxyalkylene (A2) containing methacryloxyloxy group f is 7l4g/m〇i 'The weight average molecular weight calculated by Gpc is 38200, 25. (The viscosity below is 26〇〇mPa · s.

As a result of Si NMR measurement, a bee shown as follows, which is equivalent to the constituent unit, was observed. F1 : -18.2ppm

Ml : + 8.8ppm T : -66.2ppm D2 : -19.8ppm D3 : -21.2ppm a / (b + c) The value is 〇. 78. However, no peak of S: -32·3ppm was observed; the value of d/a was 〇. &lt;&lt;5&gt; </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; The acid tertiary amyl ester (manufactured by Akzo Co., Ltd., trade name: Trigonox 121-50Ε, 50% by mass solution) is mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. . Thereafter, the curable composition was poured into a frame model made of SUS316, and was further treated at 100 Torr for 4 hours and then at 150 hours. (The hardening reaction is carried out in the next hour, and the cured product is obtained.) The evaluation results of the obtained cured product characteristics are shown in Table 2 below. [Example 16] 323923 108 201247745 <Alkyl-containing propylene-based oxy group Production of Organic Polyoxane (A2)&gt; The organopolyoxyalkylene (A2) having a mercaptopropenyloxy group was produced in the same manner as in Example 2. &lt;Manufacturing and Characterization of Hardened Material&gt 3 parts by mass of 1-hydroxy-cyclohexyl·cyclopropanone (manufactured by BASF Japan Co., Ltd., trade name: IRGACURE 184) in 100 parts by mass of the methacryloxy group-containing organic polyoxo (A2) 3 parts by mass of 2-methyl-bu [4-indolyl-phenyl]-2-N-norpoline propan-1-one (manufactured by BASF Japan, trade name: RGACURE 907) was mixed and carried out. After the mixture is uniformly homogenized, the foaming composition is obtained by defoaming. The curable composition is then placed on a glass plate (50 mm in length, 50 cm in width, 3 mm in thickness and 3 mm in thickness) to form a mold-containing model. 50mmx cross 50匪X thickness 3mm), then inject the hardening composition inside the space and clamp it with glass plate After that, it was exposed to the above-mentioned glass plate side at a cumulative irradiation amount of 2000 mj/cm 2 by an ultraviolet irradiation device (manufactured by Sakamoto SENENGINEERING Co., Ltd.) containing a high-pressure mercury lamp. The hardening was carried out at a temperature of 23 ° C and a humidity of 6 The 〇%RH environment was carried out. After the model was removed, the cured product was obtained. The evaluation results of the obtained cured product characteristics are shown in Table 2 below. [Example 17] &lt;Methyl propylene oxide Manufacture of Organic Polycohol (A2) 〉 Organic (4) Oxygen (A2) containing methyl propyloxy is manufactured in the same manner as in Example 2 of 323923 109 201247745. &lt;Manufacturing and Properties of Hardened Materials Evaluation&gt; 3 parts by mass of 3-methylpropenyloxypropyl decyl dimethane (KBM-502, Shin-Etsu, Japan) in a 100-volume-containing organic chlorinated organic polychlorite (A2) Chemical company made) and 2. 5 2: Oxygen 矽匕 y Betong's peroxy-2-ethylhexanoic acid third amyl ester (manufactured by Akz 〇, Japan, trade name: Trigonox 12 Bu 50E ' 50 quality % solution) under the helium gas, the mixture is disturbed, so that the whole is - after the 'de-foaming The hardened composition is injected into the frame model of the touch 16 system, and the hardening reaction is carried out for 4 hours under the loot and then 15 (1, butyl, and + yp ^ 丄b〇cn hours). The cured product was obtained as shown in the following Table 2. [Comparative Example 1] &lt;A methacryloxy group-containing organic polyfluorene was equipped with a stirring device, a thermometer, Manufactured> In the mouth steamed bottle, add 134g (1G = " 3.0L of 3 oxane, 420g ( 3. 〇 Mo ear) 1' 1,3, 3-tetradecyl 2 Stupid and 〇 · 〇 5g Hydrogen Mu· 1600g Mix and heat to 6 (rc reaction). After the agent is stirred under a nitrogen atmosphere, the organic poly-alcoholic-alcohol solution of the reaction product of the gas-plated rhodium is added to make the platinum metal relative to the weight 1 added to the determination of the hydrogenation reaction. The amount of 20ρρπι. Water cooled or air cooled for 55 s. .彳 'The reaction is kept warm, and 323923 to spider 'simultaneous mixing' hours. 110 201247745 After analyzing the content of the steamed bottle, the reaction rate of the base is 99%. &quot; After that, pass the activated carbon By treating and distilling off the volatile component, 405 g of the methacryloxy group-containing organopolyoxane (A15) represented by the following formula (63) can be obtained. The obtained methacryloxy group-containing oxy group The functional group equivalent of the organopolyoxyalkylene (A15) was 415 g/mol, and the weight average molecular weight calculated by GPC was 400 ', and the viscosity at 25 ° C was i50 mPa · s.

? U U 0 ft II

II CHz (63) &lt;Manufacturing and Characterization of Hardened Material&gt; 2.5 parts by mass of peroxidized _2 in 100 parts by mass of the methacryloxy group-containing organopolyoxane (A15) _ethylhexanoic acid third amyl ester (manufactured by Akzo Co., Ltd., trade name: Trig〇n〇x 1215〇E, 5〇 mass% solution) is mixed under nitrogen, and the mixture is mixed to make the whole uniform, and then After defoaming, a hardenable composition is obtained. Then, the curable composition was poured into a frame model made of SUS316, and the cured product was obtained by curing at 1 〇〇C&gt;C for 4 hours and then at 15 °C for 1 hour. The results of the properties of the cured product to be treated are shown in Table 3 below. [Comparative Example 2] &lt;3 Manufacture of organic polyoxooxime (10) of methyl propyloxy group> The following S (64) shows the organic concentrating oxime of 曱 &amp; 323923 111 201247745 Oxytomane (A16), which is X22_164C manufactured by Shin-Etsu Chemical Co., Ltd., Japan. The methacryloxy group-containing organopolyoxane (A16) had a functional group equivalent of 2,300 g/mol, a weight average molecular weight of 4,500 as determined by GPC, and a viscosity of 3,600 mPa·sS at 25 °C.

&lt;Production and Characterization of Hardened Material&gt; 2.5 parts by mass of peroxy-2-ethylhexanoic acid in 100 parts by mass of the organopolyoxyalkylene (A16) having a mercaptopropenyloxy group Triamyl ester (manufactured by Akzo Co., Ltd., trade name: Trig0n0X 12 Bu 50E, 50% by mass solution) was mixed under nitrogen, stirred to make the whole uniform, and then defoamed to obtain a curable composition. Then, the curable composition was poured into a frame model made of SUS316, and the hardening reaction was carried out at 10 (TC for 4 hours and then for 1 hour) to obtain a cured product. The evaluation results of the obtained cured product characteristics are as follows. (Comparative Example 3) <Production of epoxy group-containing organopolyoxane (A17)&gt; In a 3-neck retort equipped with a stirring shaker, a thermometer, and a reflux condenser 53 g (0.2 mol) of 1,3,5,7-tetramethylcyclotetraoxane as an (al) component, and 27 g (〇.jm) as a (^) component (dimethoxy) decane, 242 g (〇. 3 mol) of the component (bl) as shown in the following average composition formula (B1-1), the weight is 323,923, 112, 2012,477,45, and the average molecular weight is 780. ; burnt, 104g (0.9 moles) ^ ~ polydimethyl sulfonium oxide at the end of the methoxy group, 1300g of stupid, vinyl cyclohexene oxygen in the ^ (C) component (: reaction. After stirring and heating to 60, the organic pups of the reaction product are added to the reaction of the product: the amount of liquid is determined to be added to the dish. After the start, the reaction was kept warm and kept at 55 to 65 C' with water cooling or air cooling while masking for π hours. After analyzing the contents of the distillation flask, the reaction rate of the SiH group was 99%. Further, after the activated carbon treatment and distillation of the volatile component, 310 g of the epoxy group-containing organopolyoxane (A17) represented by the following formula (65) can be obtained. Oxygen (A17), which has no unsaturated bond group. The obtained epoxy group-containing organopolyoxane (A17) has a weight average molecular weight of 30,500 as determined by GPC, and the viscosity at 25 ° C is 5600raPa · s. 323923 113 201247745

An integer of 8 each. &lt;Production and Characterization of Hardened Material&gt; In 100 parts by mass of the epoxy group-containing organopolyoxane (A17), 60.5 parts by mass of mercaptohexahydrophthalic anhydride and 1 part by mass are mixed. The azabicycloundecene octoate is stirred to make the whole uniform, and then defoamed to obtain a curable composition. Thereafter, the curable composition was injected into the mold, and the hardening reaction was carried out by performing a curing reaction at 120 ° C for 1 hour and at 150 ° C for 2 hours. The evaluation results of the obtained cured product characteristics are shown in Table 3 below. [Comparative Example 4] 323923 114 201247745 &lt; Curable resin composition (A18) &gt; The curable resin composition (A18), wherein the curable resin composition for the optical semiconductor sealing material is a commercially available Japanese Shin-Etsu Chemical Co., Ltd. Manufactured by KER-2500. &lt;Production and Characterization of Hardened Material&gt; The KER-2500A and KER-2500B which have been sold are mixed in 1 〇Q parts by mass, and the whole is uniform, and then defoamed to obtain a hardenable composition. Things. Then, the curable composition was poured into a SUS316 &lt;frame model&apos; to cure at 10 Gt for 1 hour and then at 150 ° C for 5 hours to obtain a cured product. The evaluation results of the obtained cured product characteristics are shown in Table 3 below. [Comparative Example 5] <Curable resin composition (A19) &gt; A curable resin composition (A19), wherein the curable resin composition for an optical semiconductor sealing material is made of a Shinhan Chemical Co., Ltd., which is already sold. ASP-1010. &lt;Production and characterization of the cured product&gt; The ASP-1010A (trade name, manufactured by Shin-Etsu Chemical Co., Ltd., Japan) and ASP-1010B (trade name, manufactured by Shin-Etsu Chemical Co., Ltd., Japan) are each mixed in 100 parts by mass. The mixture is allowed to be mixed, and then the defoaming is carried out to obtain a curable composition. Then, the curable composition was poured into SUS316, and the cured product was obtained by performing a hardening reaction at 15 hours under 1500 hours and then at 153923 115 201247745. The obtained cured product characteristics were obtained. The evaluation result of the aspect is shown in the following Table 3. [Comparative Example 6] <Curable resin composition (A20) &gt; The curable resin composition (A20), wherein the curable resin composition for the optical semiconductor sealing material is used FX-〇 (U. &lt;Manufacturing and Characterization of Hardened Articles) manufactured by Kaneka Co., Ltd., Japan, sold FX-001A (trade name, manufactured by Kaneka, Japan): 40 parts by mass and FX- 001B (product name, manufactured by Kaneka Co., Ltd., Japan): 60 parts by mass, mixed, and stirred, and the whole is uniform, and then defoamed to obtain a curable composition. The curable composition is then injected into a frame model made of SUS316. In the medium, the hardening reaction is carried out at 100 ° C for 1 hour, at 150 ° C for 1 hour, and then at 180 ° C for 0.5 hours. The evaluation results of the obtained cured product characteristics are as follows: 3 is shown. 323923 116 2 01247745 [Table 1] Pour Example 1 Pour Example 2 List 3 Rhyme Case 4 Pour Example 5 ♦ifef Column 6 Cases 7 Pour Example 8 Organopolyoxane (A1) with unsaturated bond base 100 parts by mass Organopolyoxyalkylene (A2) containing methacryloxyloxy group 100 parts by mass of organopolyoxyalkylene containing methacryloxyloxy group (A3) 100 parts by mass of organopolyfluorene containing anthracenyl acryloxy group Alkane (A4) 100 parts by mass of organopolydecane (A5) containing methacryloxyloxy group 100 parts by mass of organopolyoxyalkylene (A6) containing mercaptopropenyloxy group 100 parts by mass of methacrylic acid containing hydrazine Oxy-organic polypolyoxyalkylene (A7) 100 parts by mass of methacryloxy-containing organopolyoxyalkylene (A8) 100 parts by mass of methacryloxy-containing organopolyoxane (A9) Alkyl propylene oxy-organic organic polyoxyalkylene (A10) methacryloxy-containing organic polyoxyalkylene (All) methacryloxy-containing oxy-organopolyoxyalkylene (A12) Acrylic oxime-based organopolyoxane (A13) containing methacryl Organic polyoxyalkylene (A14) organopolyoxyalkylene containing methacryloxyloxy group (A15) organopolyoxyalkylene containing methacryloxycarbonyl group (A16) Organic polyfluorene containing epoxy group Oxane (A17) Curable resin composition (A18) Curable resin composition (A19) Curable resin composition (A20) 3-mercapto propylene methoxy propyl fluorenyl dimethoxy decyl methyl hexahydrobenzene Dicarboxylic anhydride thermal radical generator 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass of photo radical generating agent di-octane total SiH reaction rate ◎ ◎ 〇 ◎ ◎ ◎ ◎ 〇 〇 〇 〇 ◎ ◎ ◎ ◎ ◎ ◎ 〇 〇 〇 ◎ ◎ ◎ ◎ ◎ ◎ 〇 〇 冷 冷 热 ◎ ◎ ◎ 〇 〇 〇 ◎ ◎ ◎ ◎ 〇〇〇 〇〇〇 〇〇〇 〇〇〇 〇〇. 〇〇〇 gas barrier ◎ 〇〇〇 ◎ ◎ 〇〇 323923 117 201247745 [Table 2] W example 9 Lion case 10 Miscellaneous 11 12 Lion Case 13 Lion Case 14 Lion Case 15 Lion Case 16 Acting Example 17 Organic Polyoxane (A1) Containing Unsaturated Bonds A|Polyylene-based Organic Polyoxane (A2> 100 Quality 100 parts by mass of 100 parts by mass of organopolyoxyalkylene containing methacrylic acid tomb (A3) organic polyoxyalkylene containing methacrylic acid tomb (A4&gt; organic polyfluorene containing methacrylic acid tomb Alkane (A5) Organic polyoxane containing methacrylic oxime tombs &6&gt; Organic polyfluorene containing methacrylic oxime tomb (Α7) Organic polyoxynoxy oxymethane containing methacrylic oxime Α8&gt; Organic polyxane (meth) containing methacrylofluorene tomb (100) parts by mass of organopolyoxyalkylene containing methacrylofluorene (Α10) 100 parts by mass of organic poly(meth) oxirane Hexane (All) 100 parts by mass of an organic polydecane (A12) containing a mercapto propylene oxime group 100 parts by mass of an organic polyfluorene (A13) containing a methacryloxy group. 100 parts by mass of a methyl group Acryloxy Organic polyoxyalkylene (A14) 100 parts by mass of organopolyxylene oxide containing methacryloxyloxy group (A15) Organic polydecane containing amidino propyleneoxy group (A16) Organic polymerization containing epoxy 1 Xenon (A17) Curable resin composition (A18) Curable resin composition (A19) Curable resin composition (A20) 3-mercapto propylene methoxy propyl dimethyl dimethyl hydride 3 Part of mercapto hexahydrophthalic anhydride thermal free radical generator 2.5 parts by mass 2.5 parts by mass 2.5 quality feces 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass photoradical generator 2.5 parts by mass of dinitrogen杂 ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐 耐〇〇 ◎ ◎ ◎ ◎ ◎ Hardness ◎ ◎ ◎ ◎ 〇〇 ◎ ◎ ◎ Adhesive 〇〇〇〇〇〇〇〇 ◎ Gas barrier 〇〇 ◎ ◎ 〇 ◎ 〇〇〇 323923 118 201247745 [Table 3] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Organic polyoxy siloxane (A1) containing an unsaturated bond group Containing methacryl Electrolytic organic polyoxyalkylene (A2) organic polyoxyalkylene containing mercapto propylene oxy group (A3) organic polyfluorene alkane containing fluorenyl propylene oxy group (A4) fluorenyl propylene oxide Organic polyoxyalkylene (A5) organopolyoxyalkylene containing methacryloxyloxy group (A6) organopolyoxyalkylene containing methacryloxyloxy group (A7) Organopolyoxyalkylene (A8) Organopolyoxyalkylene containing methacryloxyloxy group (A9) Organopolyoxyalkylene containing mercaptopropenyloxy group (A10) Organopoly group containing methacryloxyloxy group Hexane (All) Organopolyoxyalkylene containing methacryloxyloxy group (A12) Organopolyoxyalkylene containing methacryloxyloxy group (A13) Organopolyoxyloxy group containing methacryloxyloxy group Alkane (A14) Organopolyoxyalkylene (A15) containing methacryloxyloxy group 100 Quality Organic polyoxyalkylene (A16) containing a mercapto propylene oxime group 100 parts by mass of an organopolysiloxane containing an epoxy group (A17) 100 parts by mass of a curable resin composition (A18) 100 parts by mass of a curable resin (A19) 100 parts by mass of the curable resin composition (A20) 100 parts by mass of 3-methylpropenyloxypropylmethyl dimethyl decylmethylhexahydrophthalic anhydride 60.5 parts by mass of a thermal radical generator 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass 2.5 parts by mass photoradical generator second fading elishifin syrup 1 part by mass SiH reaction rate ◎ — ◎ — — — heat yellowing ◎ ◎ X ◎ 〇〇十光一生'◎ ◎ X ◎ X 〇 cold thermal shock resistance X ◎ ◎ ◎ ◎ X hardness ◎ X ◎ X 〇〇 adhesion 〇〇 ◎ 〇〇〇 gas barrier 〇 X ◎ XX ◎ 323923 119 201247745 This embodiment The organopolyoxane having a molecular structure having (i) F1 and M1, (ii) F1 and T, (iii) of the constituent units F1, μ, and τ represented by the above formulas (1) to (3) ) The constituent unit of any combination of FI, Ml, and T. By containing the constituent units F ft 〇 and T, an organic polysiloxane having excellent heat yellowing resistance and excellent optical properties can be obtained. # At the same time, the constituent unit of the cross-linked structure formed by the constituent unit F1 is m μ(4), and the oxygen is trapped in the molecular structure of the part, so that it can be combined with a hard sound. Resistance to thermal shock and gas barrier. Further, from the examples 1 to π, in terms of the heat yellowing, the light-resistant thermal shock resistance, the hardness, the secret and the blocking, the degree of formation required for the use of the optical semiconductor is sufficient. The organic smoldering of the transparent cured product and the sclerosing tree of the sclerosing slabs of the present invention: It is known from the comparative examples 1 to 6 that since it does not have the above-described configuration of the present embodiment, it is resistant to yellowing, light resistance, heat and cold resistance. From the viewpoints of the desired characteristics among the impact, hardness, serviceability, and gas barrier properties and the balance of these characteristics, the actual properties cannot be obtained completely. Today, the number of s monthly, is also based on the European patent application filed with Japan on March 3, 2011 (pCT/Jp2〇u/〇58115 2〇May 31, U to the Ministry of Economic Affairs of the Republic of China Patent Application No. 323923 120 201247745 (No. l. Mi96), the contents of which are also incorporated herein by reference. [Industrial Applicability] The organic poly(four) hospital of the present invention and the sclerosing properties thereof Resin composition = can be used as a wafer bonding material for optical semiconductors, a coating material, a two-component resin for nano-imprinting, and an ink (four) H. It is profitable in production. [Simplified description of the drawing] None. 】 No. 323923 121

Claims (1)

201247745 VII. Patent application scope: A kind of organic polyoxygen ray, which is contained in the molecule. The knives contain more than one group containing unsaturated bonds, and have the following general formula (n star Γ1 丄巧到( 3) The constituent units of any combination of (i) F1 and M1, (ii) F1 and T, (iii) F1 and M1 and T in the constituent soap positions F1, M1, T; FY-R2 (R1Si02/ 2) a Μ 1 X—— R^SiOA, b Τ (R1Si03/2 ) 0 Number 1 to (In) i (3) where 'R' means: replaced or unsubstituted carbon = to Η» a substituted, unsubstituted or unsubstituted carbon number of 3 to 1 fluorene:: any of the deuterated aryl group and the substituted or unsubstituted aryl group; R2 represents a carbon number of 2 to fluorene. The base; X represents a divalent hydrocarbon group having a carbon number of 2 5 1 n 1G; Y represents carbon j_; a, bL represents an integer of 1, wherein F1 represents a thousand position). The composition of the smear-like organic polyoxyalkylene 323923 201247745 2. The organic polyoxo-oxygenation according to the scope of claim 1, wherein a, b, and c satisfy the above formulas (1) to (3) The following formula (I), 〇. l^a/ (b+c) · · · (I). 3. In the case of the organic polyoxo oxane described in Item 1 or 2 of the claim, the R2 propylene oxide or methacryl oxime in the constituent unit F1 represented by the above formula (1) base. 4. The organic polylith described in any one of claims 3 to 3, wherein 其中' contains 'any of the constituent units represented by the following general formulae (4) to (4): D1, D2, D3, D 1 : ( R12Si〇2'2) D 2 : ( RlSi〇2/2 ) D 3 : ( R12Si〇 2, 2) (In the general formulae (4) to (6), 'R1 represents: substituted or unsubstituted The choice of the alkyl group having 1 to 10 carbon atoms, the substituted or unsubstituted carbon group having 3 to 1 ring of a cycloalkyl group, the substituted or unsubstituted aryl group, and the substituted or unsubstituted aralkyl group X represents a dihydrocarbyl group having a carbon number of 2 to 1 (); a unit of which is a constituent unit of the 'Db D2 table-like organic polycohol, and 3 is a constituent unit of the chain-like organopolyoxane. The organic polyoxo igniting 'in which' contains the constituent unit s represented by the following general formula (7), 323923 2 201247745 and the general formula (7) is shown in the above. The content of the constituent unit satisfies the following formula (π) with respect to the content of the constituent unit F1 represented by the above formula (1): d/a ^〇.1 ---(11) S: (RiHSi〇2 /2)d (7) (In the formula (7), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 1 ring carbon number, a substitution or Any one selected from the group consisting of an unsubstituted aryl group and a substituted or unsubstituted aryl group; wherein the constituent unit S represents a constituent unit of a cyclic or chain organopolysiloxane. 6. The organopolysiloxane according to any one of claims 1 to 5, which contains only the constituent unit represented by the above formula (1)! ^, as a constituent unit containing the above R2. 7. The organopolyoxane according to any one of the above-mentioned claims, wherein the structural unit F1 represented by the above formula (丨) and the following formula (8) are contained. The constituent unit F2 is a constituent unit containing the above R2 (and, in the following general formula (8), β is contained in the above R2) F 2 : Y - R21 (R12SiCV2) • · · ( 8 ) (above In the formula (8), R1 represents a substituted or unsubstituted carbon group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon group of 3 to 1 fluorene. 323923 3 201247745 Substituted or unsubstituted aryl Any one selected from the group consisting of a substituted or unsubstituted aralkyl group; R21 represents an acryloxy group or a methacryloxy group; and Y represents a carbon number of 2 to 1 Å; , F2 represents the constituent unit of the chain organic polysulfide. An organopolyoxane wherein the 'organic polyoxoxime according to any one of claims 1 to 7 of the patent application range contains 0.1 to 100 parts by mass with respect to 100 parts by mass of the following The cyclic organopolyphosphonium represented by the formula (9): Ri-sio-R1 y^iolx 丨R2 • · · vy ) (In the above formula (9), R1 represents a substituted or unsubstituted carbon Any one selected from the group consisting of an alkyl group having 1 to 10 alkyl groups, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group; R21醯 醯 醯 曱 曱 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示 表示And an organic polyoxane wherein the organic polyoxane as shown in any one of claims 1 to 8 of the patent application range contains 〇. 01 to 1000 parts by mass of a compound represented by the following formula (1〇), 323923 4 201247745 1H-R1 "-810-&gt;-丨S1IR1 V)Γ-lio&gt;-卩10-11 RIS'IY--sIR« R1- wlsio-R 11. I h Rl^IX— R •••(10) (In the above formula (10), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon number of 3 Any one selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group; R21 represents an acryloxy group or a methyl propylene oxide group, X a divalent radical having no carbon number of 2 to 10, g represents an integer of 1 or more; h represents an integer of 0 or more; i represents an integer of 0 to 20.) 10. As in any one of claims 1 to 9 of the patent application. The organopolyoxane having a cyclic organopolyoxane represented by the following formula (9) and a compound represented by the following formula (R) R1 (ping) j - X r1 I R21 • (9) (In the above formula (9), R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon number of 3 to 丨〇. Any one selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; R21 represents a propylene-sensitized oxy group or a fluorenyl propyl group 323923 5 201247745 oxy group; Carbon 2 to 10 divalent hydrocarbon groups; e represents an integer of 1 or more, f represents an integer of 0 or more; e + f represents an integer of 3 to 20) f R1 R1 R1 ksiO^SiOMSiO)-(SiO)- X R1 丫1 + 丄21 R1—SiO—(SiO)i-Si—R1 R1 R1 R1 •••(10) (In the formula (10), R1 represents a substituted or unsubstituted alkyl group having a carbon number of from j to 10, Any one selected from the group consisting of a substituted or unsubstituted cycloalkyl group having 3 to 1 Å carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group; R21 represents an acryloxy group or a group a propylene oxy group; X represents a divalent hydrocarbon group having a carbon number of 2 to 1 Å; g represents an integer above 丨; h represents an integer above 〇; 丨 represents an integer of 〇 to 2〇) which is supported by matrix-assisted free radicalization The intensity of the peak obtained by the time-based mass spectrometry is calculated by the following formula (111), and the ratio of the compound content represented by the above formula (10) (WB) to the content of the compound represented by the formula (8) is: The value is 0. 1 or more and 20. The following is the case. [1] (10)·] = the peak of the mass of the mass henna quality 23 of the structure conforming to the general formula (1)) / Structure corresponding to the formula ⑷f 323923 * sodic quality and the total mass of relatively strong peaks 23 201 247 745 degrees .. ·· (III). The organopolysiloxane described in any one of the above claims, wherein R1 is an alkyl group having 1 to 10 carbon atoms. The organopolyoxane according to any one of claims 1 to 11, wherein the above R1 is a fluorenyl group. 13. The organopolyxide chamber according to any one of claims 1 to 12, wherein the above R2 contains an acryloxy group or a mercaptopropenyloxy group and an acryloxy group or a methacryl group The functional group equivalent of the methoxy group is from 210 to 2100 g/mole. 14. The organic polyoxo fired according to any one of claims 1 to 13 which has a weight average molecular weight of 700 to 5,000,000 and a viscosity at 25 ° C of 50 to loooooo mpa · s. A method for producing an organopolyoxane, which comprises the method of the following steps: - (4) The desired hydrogenated polyoxyalkylene (a2) having a direct ^ (al) on the ship, and the i) having more than two organic polyoxygens directly bonded to the vinyl group (bl) Or the ethylene group with ^ is attached to the Shi Xi atom _ base of the money to burn (10) more than 2 straight: (1) 1 molecule has more than 2 and = and (C) addition reaction, the bond organicization 323923 And the amount of the carbonization reaction catalyst (4) is 2012-0745 R1 R1 ^ίοΗφ〇)^ η R1 (11) (In the formula (11), R1 represents a substituted or unsubstituted carbon number of 1 to 10 Any one selected from the group consisting of an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 1 Å carbon atoms, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group; j represents 1 or more An integer; k represents an integer above 〇, and j+k represents an integer from 3 to 20. 16. The method for producing an organopolysiloxane according to the fifteenth aspect of the invention, wherein the step of performing the addition reaction comprises: a step of preparing a reaction liquid, and adding a hydrogenation reaction to the reaction liquid. a step of the catalyst (d), wherein the reaction liquid contains the hydrogenated polyoxoxime (a/) represented by the above formula (11), and the above-mentioned one or more hydrogens directly bonded to the austenite atom Atomic hydrogenated polyoxyalkylene (a2), a vinyl group-containing organic polyoxyl (bl) having two or more vinyl groups bonded directly to a ruthenium atom, and one molecule = one upper unsaturated bond Organic compound (c), or having more than 2 or more directly bonded to the hair-based (4) oxy-fired ((8) and organic compound having 2 or more unsaturated bonds in one molecule (4) 77 nm Lifanyuan item 15 The manufacturing method of the organic poly-fat is described in (4): the reverse-knocking step of the upper-cutting line, the step of preparing the reaction liquid by 323923 201247745, and the hydrogenation of the imaginary (11) (al) According to the =::: formula, more than one hydrogen atom directly bonded to the ruthenium atom One of the two molecules having two or more unsaturated bonds is It ==:::: = Wei U1), and the hydrogenation of the ruthenium atom with more than one direct bond atom is required. And an adduct of the organic compound (4) having two or more unsaturated bonds in one molecule, and an addition step of the above-mentioned reaction liquid towel, including the above-mentioned ethylene group having two or more f-bonded to 11 atoms a di-organic polyoxyl (b) of B, or a polyoxyalkylene (b2) having two or more groups bonded directly to the Shihe atom. An organic resin composition containing (10) parts by mass of the organic polyoxygenated gas and 10 to 10 parts by mass of the thermal radical generating agent as described in any one of claims 1 to 14 of the patent application . A sclerosing resin composition containing (10) parts by mass of an organic polyoxymethane as described in any of claims 1 to 14 and 5 to 20 parts by mass of photoradical generation Agent. The sclerosing resin composition according to any one of claims 1 to 14, wherein the organic polymerization according to any one of claims 1 to 14 "Oxygen Margin" also contains 0·1 323923 9 201247745 to 10 parts by mass of decane coupling agent. The sclerosing resin composition according to the above-mentioned item of the present invention, wherein the organic material as described in any one of claims 1 to 14 of the patent application is related to 100 parts by mass. The polyoxyalkylene gas further contains (d) % of a hydrogenation catalyst of 0.001 parts by mass or less. The sclerosing resin composition according to any one of claims 1 to 4, wherein the organic polymer according to any one of claims 1 to 14 of the patent application, in relation to 100 parts by mass The oxoxane further contains 0.1 to 500 parts by mass of an inorganic oxide. A sealing material for a photo-semiconductor comprising the curable resin composition according to any one of claims 18 to 22. A die bonding material for a photo-semiconductor, which comprises a curable resin composition according to any one of claims 18 to 22. A coating material comprising the curable resin composition according to any one of claims 18 to 20. A curable resin composition for a nano-imprint, which comprises the curable resin composition according to any one of claims 18 to 22. An ink-based composition comprising a curable resin composition and a coloring agent according to any one of claims 18 to 22. The optical semiconductor package is formed by using a sealing material for an optical semiconductor as described in claim 23 of the patent application. 323923 10 201247745 IV. Designated representative map: There is no schema in this case. (1) The representative representative of the case is: No. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 323923 4