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KR-102961316-B1 - Organopolysiloxane, method of manufacturing the same, and thermally conductive silicone composition

KR102961316B1KR 102961316 B1KR102961316 B1KR 102961316B1KR-102961316-B1

Abstract

An organopolysiloxane represented by the general formula: (wherein R1 is an identical or different aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R2 is an identical or different monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have an aliphatic unsaturated bond, R3 is an identical or different alkyl group having 1 to 3 carbon atoms, n is an integer from 1 to 500, and a is 0 or 1), and a thermally conductive silicone composition having good handling workability even when containing a large amount of a thermally conductive filler, wherein the organopolysiloxane is used as a surface treatment agent or main component of a thermally conductive filler.

Inventors

  • 후꾸이, 히로시
  • 도야마, 쿄코
  • 키시모또, 노리히사

Assignees

  • 다우 도레이 캄파니 리미티드

Dates

Publication Date
20260508
Application Date
20201030
Priority Date
20191030

Claims (11)

  1. General formula: [Tue 26] (In the formula, R1 is an identical or different aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R2 is an identical or different monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have an aliphatic unsaturated bond, R3 is an identical or different alkyl group having 1 to 3 carbon atoms, n is an integer from 10 to 500, and a is 0 or 1) Organopolysiloxane represented as
  2. In paragraph 1, organopolysiloxane, which is a surface treatment agent for mineral powder.
  3. ◈Claim 3 was waived upon payment of the establishment registration fee.◈ In paragraph 2, the inorganopolysiloxane is a thermally conductive powder.
  4. General formula: [Tue 27] (In the formula, R1 is an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R2 is an identical or different monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have an aliphatic unsaturated bond, R3 is an alkyl group having 1 to 3 carbon atoms, and n is an integer from 10 to 500) Organopolysiloxane represented by, and general formula: R 1 R 2 a Si(OR 3 ) (3-a) (In the formula, R1 is an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R2 is a monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have the same or different aliphatic unsaturated bonds, R3 is an alkyl group having 1 to 3 carbon atoms that is the same or different, and a is 0 or 1) A method for producing an organopolysiloxane as described in claim 1, characterized by performing a dealolytic condensation reaction on an alkoxysilane represented by
  5. (A) General formula: [Tue 28] (In the formula, R1 is an identical or different aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, R2 is an identical or different monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have an aliphatic unsaturated bond, R3 is an identical or different alkyl group having 1 to 3 carbon atoms, n is an integer from 10 to 500, and a is 0 or 1) Organopolysiloxane represented by, and (B) Thermally conductive filler A thermally conductive silicon composition comprising at least [the following].
  6. In claim 5, a thermally conductive silicon composition having an average particle size of (B) 0.01 to 100 μm.
  7. In paragraph 5, a thermally conductive silicon composition in which (B) the component is alumina powder.
  8. A thermally conductive silicon composition according to claim 7, wherein (B) the composition comprises a mixture of (B 1 ) spherical or round alumina powder having an average particle size of 5 to 50 μm (provided that 5 μm is not included) and (B 2 ) spherical or irregular alumina powder having an average particle size of 0.1 to 5 μm.
  9. A thermally conductive silicon composition according to claim 8, wherein component (B) consists of 30 to 90 mass% of component ( B1 ) and 10 to 70 mass% of component ( B2 ).
  10. A thermally conductive silicon composition according to claim 5, wherein the content of component (B) is 500 to 3,000 parts by mass per 100 parts by mass of component (A).
  11. In claim 5, a thermally conductive silicone composition further comprising (C) a crosslinking agent.

Description

Organopolysiloxane, method of manufacturing the same, and thermally conductive silicone composition The present invention relates to a novel organopolysiloxane, a method for manufacturing the same, and a thermally conductive silicone composition using the organopolysiloxane. Patent documents 1 to 3 disclose that an organopolysiloxane having a silicon atom bonding hydrolyzable group at the molecular chain end acts as a surface treatment agent for a thermally conductive filler to obtain a high thermally conductive silicone composition by filling a large amount of thermally conductive filler. However, even when using such an organopolysiloxane, if a high amount of thermally conductive filler such as alumina is filled, the viscosity of the resulting silicone composition increases rapidly, and there was a problem in that its handling workability and moldability were significantly reduced. First, the organopolysiloxane of the present invention will be described in detail. The organopolysiloxane of the present invention is of the general formula: [Painting 4] It is displayed as. In the above formula, R1 is an aliphatic unsaturated monovalent hydrocarbon group having 2 to 12 carbon atoms, which may be the same or different. Specifically, examples include straight-chain alkenyl groups such as vinyl, allyl, butenyl, hexenyl, decenyl, undecenyl, and dodecenyl groups; branched-chain alkenyl groups such as iso-propenyl, 2-methyl-2-propenyl, and 2-methyl-10-undecenyl groups; aliphatic unsaturated cyclic alkyl groups such as vinylcyclohexyl; aryl groups containing aliphatic unsaturation such as vinylphenyl; and aralkyl groups containing aliphatic unsaturation such as vinylbenzyl and vinylphenethyl groups. Preferably, it is a straight-chain alkenyl group, and particularly preferably, it is a vinyl, allyl, or hexenyl group. The position of the aliphatic unsaturated bond in R1 is not limited, but it is preferred that it be a position far from the silicon atom to which R1 is bonded. In addition, among the above formulas, R2 is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms that does not have an aliphatic unsaturated bond, and specifically, examples include straight-chain alkyl groups such as methyl, ethyl, propyl, and butyl groups; branched-chain alkyl groups such as iso-propyl, tert-butyl, and tert-pentyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; aryl groups such as phenyl, tolyl, and xylyl groups; aralkyl groups such as benzyl and phenethyl groups; and halogenated alkyl groups such as 3-chloropropyl and 3,3,3-trifluoropropyl groups, and preferably is an alkyl group or an aryl group, more preferably is an alkyl group having 1 to 4 carbon atoms, and particularly preferably is a methyl or ethyl group. In addition, in the above formula, R3 is an alkyl group having 1 to 3 carbon atoms that is the same or different, specifically exemplified by a methyl group, an ethyl group, or a propyl group, and preferably a methyl group or an ethyl group. In addition, in the above formula, n is an integer from 1 to 500, preferably n is at least 5, at least 10, at least 15, or at least 20, while at most 400, at most 300, or at most 200. The range of n can be any range formed by combining the upper and lower limits mentioned above. This is because if n is above the lower limit of the above range, volatility becomes insufficient, while if it is below the upper limit of the above range, the surface of the inorganic filler, particularly the thermally conductive filler, can be sufficiently treated. In addition, among the above formulas, a is 0 or 1, and preferably 0. As a method for preparing such organopolysiloxanes, for example, general formula: [Tuesday 5] Organopolysiloxane represented by, and general formula: R 1 R 2 a Si(OR 3 ) (3-a) One method is to perform a dealolysis condensation reaction on an alkoxysilane represented by [this]. R1 , R2 , and n in the above organopolysiloxane are the same as above. Such organopolysiloxane can be prepared by using an alkyl lithium or lithium silanolate as a polymerization initiator, as disclosed in, for example, U.S. Patent No. 5486635 (Japanese Patent Publication No. Hei 7-292109) or Japanese Patent Publication No. Hei 10-7801, and then performing a non-equilibrium polymerization reaction of a cyclic trisiloxane in the presence or absence of an organosilane or organosiloxane having a hydroxyl group at the end of a molecular chain, which is a molecular weight regulator, and then stopping the non-equilibrium polymerization reaction with an acid. In addition, it is preferable to perform the non-equilibrium polymerization reaction in the presence of a nitrile compound or an ester compound and a polar solvent that does not have active hydrogen, after pre-silylating or acetylating trace amounts of silanol group-containing impurities present in the cyclic trisiloxane. Thus, it is possible to suppress the formation of by-products of uni-term no