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  • C08G18/08—Processes
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  • C08G18/30—Low-molecular-weight compounds
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  • C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
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  • C08G18/40—High-molecular-weight compounds
  • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
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  • C08G18/40—High-molecular-weight compounds
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  • C08G18/44—Polycarbonates
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  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4804—Two or more polyethers of different physical or chemical nature
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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  • C08G18/4804—Two or more polyethers of different physical or chemical nature
  • C08G18/4808—Mixtures of two or more polyetherdiols
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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  • C08G18/4804—Two or more polyethers of different physical or chemical nature
  • C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
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  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4825—Polyethers containing two hydroxy groups
• • C—CHEMISTRY; METALLURGY
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4829—Polyethers containing at least three hydroxy groups
• • C—CHEMISTRY; METALLURGY
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
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• • C—CHEMISTRY; METALLURGY
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
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• • C—CHEMISTRY; METALLURGY
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  • C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
  • C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
  • C08G18/5084—Phosphate compounds
• • C—CHEMISTRY; METALLURGY
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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  • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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  • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
  • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
  • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • C—CHEMISTRY; METALLURGY
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  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/78—Nitrogen
  • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
  • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
  • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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  • C08K5/00—Use of organic ingredients
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  • C08K5/10—Esters; Ether-esters
  • C08K5/101—Esters; Ether-esters of monocarboxylic acids
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• • C—CHEMISTRY; METALLURGY
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  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/52—Phosphorus bound to oxygen only
  • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
  • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
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  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
  • C09K5/08—Materials not undergoing a change of physical state when used
  • C09K5/14—Solid materials, e.g. powdery or granular
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Definitions

• the present invention relates to a curable composition, a urethane resin obtained by curing the curable composition, and a heat radiating member containing the urethane resin.
• a heat conductive resin is known as a resin that dissipates (heats heat) heat generated by an electronic component or the like to the outside.
• a heat dissipation method using a heat conductive resin a method of laminating a heat conductive resin on a housing of a heating element is known, and in order to efficiently dissipate heat by such a method, excellent heat is obtained. Not only conductivity but also flexibility that can follow the shape of the heating element and adhere to the surface of the heating element is required.
• the polyurethane polymer described in Patent Document 1 is known.
• the polyurethane polymer described in Patent Document 1 does not have sufficient thermal conductivity, and if the amount of the heat-dissipating (heat-conducting) filler is increased in order to enhance the heat-dissipating property, the flexibility is lowered and the heat-dissipating efficiency is lowered. There was a problem. Further, in recent years, since the number of heat generating members having a large amount of heat generation and a complicated shape has increased, it has been required to develop a heat conductive resin capable of achieving both excellent heat conductivity and flexibility.
• An object of the present invention is to provide a thermally conductive urethane resin having excellent thermal conductivity and excellent flexibility.
• the present inventors have arrived at the present invention as a result of diligent studies to solve the above problems. That is, in the present invention, the polyol (A), the polyisocyanate (B), the phosphoric acid ester (C1) represented by the following general formula (1), the fatty acid (C2) having 12 to 24 carbon atoms, and the sucrose fatty acid ester It contains at least one dispersant for inorganic filler (C) selected from the group consisting of (C3), sorbitan fatty acid ester (C4) and glycerin fatty acid ester (C5), and the inorganic filler (D) as described below.
• It contains at least one dispersant for inorganic filler (C) selected from the group consisting of (C3), sorbitan
• the polyol (A) contains 50% by weight or more of the polyalkylene glycol (A1) having a chemical formula amount or a number average molecular weight of 1000 or less based on the weight of the polyol (A).
• the inorganic filler (D) is contained in an amount of 70 to 97% by weight based on the weight of the curable composition.
• the total weight of the dispersant (C) for an inorganic filler is 1 to 5 parts by weight with respect to 100 parts by weight of the inorganic filler (D).
• R 1 is a hydrogen atom, an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms
• a 1 O is an alkyleneoxy group having 2 to 3 carbon atoms.
• N1 is an integer of 3 to 15
• R 2 is a hydrogen atom or- (A 2 O) n2 R 3 (R 3 is an alkyl group having 2 to 18 carbon atoms, or 2 to 18 carbon atoms.
• an alkenyl group, a 2 O is an alkyleneoxy group having 2-3 carbon atoms
• n2 is an an integer of 3-15).
• the curable composition of the present invention comprises a polyol (A), a polyisocyanate (B), and the following general formula (1).
• R 1 is a hydrogen atom, an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms
• a 1 O is an alkyleneoxy group having 2 to 3 carbon atoms.
• N1 is an integer of 3 to 15
• R 2 is a hydrogen atom or- (A 2 O) n2 R 3 (R 3 is an alkyl group having 2 to 18 carbon atoms, or 2 to 18 carbon atoms.
• a phosphate ester represented by, a fatty acid (C2) having 12 to 24 carbon atoms, a sucrose fatty acid ester (C3), a sorbitan fatty acid ester (C4) and a glycerin fatty acid ester (C5). It contains one kind of dispersant for an inorganic filler (C) and an inorganic filler (D).
• the curable composition of the present invention contains all of the polyol (A), the polyisocyanate (B), the dispersant for an inorganic filler (C) and the inorganic filler (D) in one agent (first aspect).
• the curable composition of the first aspect contains a polyol (A), a polyisocyanate (B), a dispersant for an inorganic filler (C) and an inorganic filler (D) in one agent.
• the polyol (A) contains 50% by weight or more of the polyalkylene glycol (A1) having a chemical formula amount or a number average molecular weight of 1000 or less based on the weight of the polyol (A).
• the polyalkylene glycol (A1) include diols obtained by addition polymerization of an aliphatic diol having 2 to 20 carbon atoms and an alkylene oxide having 2 to 4 carbon atoms (hereinafter referred to as AO).
• Examples of the aliphatic diol having 2 to 20 carbon atoms include ethylene glycol, propylene glycol, 1,3- and 1,4-butanediol, 1,6-hexanediol, neopentyl glycol and the like, and ethylene glycol is preferable.
• Propylene glycol more preferably ethylene glycol.
• Examples of AO include ethylene oxide, 1,2- or 1,3-propylene oxide and 1,2-, 1,3-, 1,4- or 2,3-butylene oxide, and ethylene oxide is preferable.
• 1,2- or 1,3-propylene oxide, more preferably 1,2- or 1,3-propylene oxide. Two or more of these AOs may be used in combination, and in the case of two or more types of AO, the binding mode of AO may be block addition, random addition, or a combination thereof.
• the chemical formula amount or number average molecular weight of the polyalkylene glycol (A1) is 1000 or less, preferably 500 or less, and more preferably 300 or less.
• the chemical formula amount or the number average molecular weight of the polyalkylene glycol (A1) is 1000 or less, the content of the inorganic filler in the curable composition can be increased, and a cured product of the curable composition can be easily obtained. Can be done.
• the chemical formula amount or number average molecular weight of the polyalkylene glycol (A1) exceeds 1000, it tends to be difficult to increase the amount of the inorganic filler in the curable composition and to obtain a cured product of the curable composition. ..
• the proportion of the polyalkylene glycol (A1) contained in the polyol (A) is 50% by weight or more, preferably 70 to 100% by weight, and more preferably 90 to 100% by weight based on the weight of the polyol (A). be.
• the ratio of the polyalkylene glycol (A1) in the polyol (A) is 50% by weight or more, the content of the inorganic filler in the curable composition can be increased, and the cured product of the curable composition can be easily prepared. Can be obtained.
• the proportion of the polyalkylene glycol (A1) contained in the polyol (A) is less than 50% by weight based on the weight of the polyol (A), the content of the inorganic filler in the curable composition may be increased. It becomes difficult, and it becomes difficult to obtain a cured product of the curable composition.
• the number average molecular weight (Mn) is a value measured under the following conditions using gel permeation chromatography (hereinafter abbreviated as GPC).
• Device body HLC-8120 (manufactured by Tosoh Corporation)
• Column TSKgel ⁇ 6000, G3000 PWXL manufactured by Tosoh Corporation Detector: RI (Refractive Index)
• Eluent 0.5% sodium acetate / water / methanol (volume ratio 70/30)
• Eluent flow rate 1.0 ml / min
• Injection volume 200 ⁇ l
• Standard substance TSK STANDARD POLYETHYLENE OXIDE manufactured by Tosoh Corporation
• Data processing software GPC-8020modelII (manufactured by Tosoh Corporation)
• the polyalkylene glycol (A1) having a chemical formula amount or a number average molecular weight of 1000 or less can be produced by a known method, and for example, AO is added to the above-mentioned aliphatic diol having 2 to 20 carbon atoms by a known method. There is a way to do it. By adjusting the amount of AO used, the chemical formula amount or the number average molecular weight can be reduced to 1000 or less.
• the polyalkylene glycol (A1) may be used alone or in combination of two or more.
• the polyol (A) may contain other polyols (A2) in addition to the polyalkylene glycol (A1).
• Examples of the other polyol (A2) include an aliphatic diol (A21), a trivalent or higher aliphatic polyol (A22), and an AO adduct of the aliphatic diol (A21) having a chemical formula amount or a number average molecular weight of 1000.
• AO adduct (A23) exceeding AO adduct (A23), AO adduct (A24) of the aliphatic polyol (A22), alicyclic polyol (A25), AO adduct (A26) of the alicyclic polyol (A25), divalent or higher.
• Examples thereof include an AO adduct (A27), a polyester polyol (A28), a polybutadiene polyol (A29), and a polycarbonate polyol (A30).
• Examples of the aliphatic diol (A21) include an aliphatic diol having 2 to 20 carbon atoms, and the aliphatic diol is preferably 2 to 10 and more preferably 2 to 5 carbon atoms.
• Examples of the trivalent or higher aliphatic polyol (A22) include alcohols having a trivalent or higher valence among aliphatic polyols having 3 to 20 carbon atoms, glycerin, pentaerythritol and the like, and glycerin is preferable.
• Examples of the AO adduct (A23) of the aliphatic diol (A21) include the compound obtained by adding AO to the aliphatic diol (A21), and the amount of AO added can be adjusted to exceed 1000 chemical formulas or. Examples thereof include those having a number average molecular weight.
• the AO the AO having 2 to 4 carbon atoms exemplified in the description of the polyalkylene glycol (A1) can be used, and the preferred one is also the same.
• Examples of the AO adduct (A23) of the aliphatic diol (A21) include polypropylene glycol, polyethylene glycol, polytetramethylene glycol and the like having a chemical formula amount or a number average molecular weight of more than 1000, and among them, polypropylene glycol and polytetra are preferable. Methylene glycol, more preferably polypropylene glycol.
• Examples of the AO adduct (A24) of the aliphatic polyol (A22) include a compound obtained by adding AO to the aliphatic polyol (A22).
• the AO the same ones as exemplified in the description of (A1) can be used, and the preferred ones are also the same.
• Examples of the AO adduct (A24) of the aliphatic polyol (A22) include an AO adduct of glycerin and an AO adduct of pentaerythritol, and specific examples thereof include polyoxyethylene triol (polyethylene glyceryl ether) and polyoxypropylene.
• triol polyoxypropylene glyceryl ether
• polyoxyethylene polyoxypropylene triol polyoxyethylene polyoxypropylene glyceryl ether
• polypropylene triol, polyoxyethylene polyoxypropylene triol, and polyoxypropylene triol are preferable, and polyoxyethylene polyoxypropylene triol and polyoxypropylene triol are more preferable.
• Examples of the alicyclic polyol (A25) include alicyclic polyols having 4 to 16 carbon atoms (1,4-cyclohexanediol, 1,4-cyclohexanedimethanol and hydrogenated bisphenol A).
• Examples of the AO adduct (A26) of the alicyclic polyol (A25) include a compound obtained by adding AO to the alicyclic polyol (A25).
• the AO the same ones as exemplified in the description of (A1) can be used, and the preferred ones are also the same.
• Examples of the divalent or higher phenol in the AO adduct (A27) of the divalent or higher phenol include polyvalent phenols having 6 to 16 carbon atoms (bisphenol A, bisphenol S, hydroquinone, etc.) and the like.
• Examples of the AO adduct (A27) of a divalent or higher phenol include the above-mentioned compound in which AO is added to a divalent or higher phenol.
• the same ones as exemplified in the description of (A1) can be used, and the preferred ones are also the same.
• polyester polyol (A28) examples include polyols [the polyalkylene glycol (A1), the aliphatic diol (A21), the aliphatic polyol (A22), the AO adduct (A23) of the aliphatic diol (A21), and the aliphatic polyol. (A22) AO adduct (A24), alicyclic polyol (A25), alicyclic polyol (A25) AO adduct (A26), divalent or higher phenol AO adduct (A27), etc.] Examples thereof include a condensate with a polycarboxylic acid.
• polycarboxylic acid examples include chain aliphatic polycarboxylic acids having 2 to 20 carbon atoms [succinic acid, malonic acid, dipropylmalonic acid, succinic acid, 2,2-dimethylsuccinic acid, glutaric acid, 2-methylglutaric acid.
• polybutadiene polyol (A29) those obtained from the market such as “G-1000”, “G-2000” and “G-3000” [manufactured by Nippon Soda Co., Ltd.] may be used. Further, as the polybutadiene polyol (A29), a hydrogenated product of the polybutadiene polyol may be used, and the hydrogenated products are "GI-1000", “GI-2000” and “GI-3000” [manufactured by Nippon Soda Co., Ltd.]. Etc., can be obtained from the market.
• polycarbonate polyol (A30) examples include polyols [the polyalkylene glycol (A1), the aliphatic diol (A21), the aliphatic polyol (A22), the AO adduct (A23) of the aliphatic diol (A21), and the aliphatic polyol.
• the other polyol (A2) used together with the polyalkylene glycol (A1) is preferably an aliphatic diol (A21) or an aliphatic polyol (A21) from the viewpoint of excellent moldability of a molded product obtained from a curable composition.
• AO adduct and a polycarbonate polyol which is a reaction product of 3-methyl-1,5-pentanediol, 1,6 hexanediol and phosgen.
• moldability of a molded product obtained from a curable composition may be simply referred to as “moldability”.
• excellent in moldability means that it is easy to mold into a desired shape.
• the polyol (A2) may be used alone or in combination of two or more.
• the polyol (A) preferably has at least two or more hydroxyl groups on average per molecule from the viewpoint of excellent moldability.
• the number average molecular weight of the polyol (A) is preferably 1,000 to 10,000, more preferably 1,500 to 9,000 from the viewpoint of excellent moldability.
• polyisocyanate (B) examples include chain aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and isocyanurates of these polyisocyanates.
• chain aliphatic polyisocyanate examples include chain aliphatic polyisocyanates having 4 to 20 carbon atoms, preferably ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, and 2,2,4-trimethyl. Examples thereof include hexamethylene diisocyanate and lysine diisocyanate.
• alicyclic polyisocyanate examples include an alicyclic polyisocyanate having 6 to 17 carbon atoms, preferably isophorone diisocyanate, 4,4-dicyclohexylmethane diisocyanate, cyclohexene diisocyanate, methylcyclohexene diisocyanate, and bis (2-). Isocyanatoethyl) -4-cyclohexene-1,2-dicarboxylate and 2,5- or 2,6-norbornane diisocyanate and the like. As the alicyclic polyisocyanate, it can be obtained from the market as Death Module I [Sumika Covestro Urethane Co., Ltd.].
• aromatic polyisocyanate examples include aromatic polyisocyanates having 8 to 22 carbon atoms, preferably 1,3- or 1,4-phenylenediocyanate, 2,4- or 2,6-tolylene diisocyanate (TDI). ), 4,4'-or 2,4'-diphenylmethane diisocyanate (MDI), m- or p-isocyanatophenylsulfonyl isocyanate, 4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4 '-Diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, 1,5-naphthylene diisocyanate, m- or p-isocyanatophenylsulfonyl isocyanate, m- or p-xylylene Examples thereof include isocyanate (XDI) and ⁇ , ⁇ , ⁇ ''
• Examples of the isocyanurate form of the polyisocyanate include a trimer of the polyisocyanate (the above-mentioned chain aliphatic polyisocyanate, alicyclic polyisocyanate, aromatic polyisocyanate, etc.).
• the isocyanurate form of polyisocyanate can be obtained from the market as TLA-100 [Asahi Kasei Co., Ltd.] or the like.
• polyisocyanates (B) from the viewpoint of excellent moldability, chain aliphatic polyisocyanates, alicyclic polyisocyanates, isocyanurates of chain aliphatic polyisocyanates and isocyanurates of alicyclic polyisocyanates are used. preferable.
• the polyisocyanate (B) may be used alone or in combination of two or more.
• the ratio of the total weight of the polyol (A) and the polyisocyanate (B) in the curable composition is preferably 3 to 30% by weight, more preferably 3 to 20% by weight, based on the weight of the curable composition. %.
• the isocyanate index of the polyol (A) and the polyisocyanate (B) [total number of moles of isocyanate groups of the polyisocyanate (B) / total number of moles of hydroxyl groups of the polyol (A)] is 0.2 to 1.0. (More preferably 0.5 to 0.8). When the isocyanate index is in the above range, the curability of the curable composition and the flexibility of the cured product are good.
• the curable composition of the present invention comprises a phosphate ester (C1) represented by the following general formula (1), a fatty acid (C2) having 12 to 24 carbon atoms, a sucrose fatty acid ester (C3), and a sorbitan fatty acid ester (C4). ) And at least one dispersant (C) for an inorganic filler selected from the group consisting of the glycerin fatty acid ester (C5).
• R 1 is a hydrogen atom, an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms
• a 1 O is an alkyleneoxy group having 2 to 3 carbon atoms.
• N1 is an integer of 3 to 15
• R 2 is a hydrogen atom or- (A 2 O) n2 R 3 (R 3 is an alkyl group having 2 to 18 carbon atoms, or 2 to 18 carbon atoms.
• an alkenyl group, a 2 O is an alkyleneoxy group having 2-3 carbon atoms
• n2 is an an integer of 3-15).
• R 1 is a hydrogen atom, an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms.
• Alkyl groups having 2 to 18 carbon atoms include ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group and tetradecyl group. Examples thereof include a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group and the like, and each of them may be linear or branched.
• alkenyl group having 2 to 18 carbon atoms examples include an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group and a tetradecenyl group.
• Examples thereof include a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, etc., each of which may be linear or branched, and the position of the double bond is not limited.
• R 1 may be linear or branched, but it is preferably linear. Further, an alkyl group having 12 to 18 carbon atoms is preferable from the viewpoint of the mechanical strength of the cured product of the curable composition and the dispersibility of the inorganic filler.
• a 1 O means an alkyleneoxy group having 2 to 3 carbon atoms, and examples thereof include an ethyleneoxy group and a propyleneoxy group. Of these, ethyleneoxy groups are preferable from the viewpoint of dispersibility.
• n1 is an integer of 3 to 15, preferably 3 to 13, and more preferably 4 to 11 from the viewpoint of good dispersibility of the inorganic filler and good mechanical strength of the cured product.
• R 2 is a hydrogen atom or- (A 2 O) n2 R 3 (R 3 is an alkyl group having 2 to 18 carbon atoms or an alkenyl group having 2 to 18 carbon atoms, and A 2 O is an alkenyl group having 2 to 18 carbon atoms. It is an alkyleneoxy group of 3 to 3, and n2 is an integer of 3 to 15).
• R 3 include the same as those of R 1, and the same applies to preferable ones.
• a 2 O the same as A 1 O can be mentioned, and the preferable one is also the same.
• R 2 is a hydrogen atom
• the compound of the general formula (1) is a monoester
• R 2 is ⁇ (A 2 O) n2 R 3
• the compound of the general formula (1) is a diester
• R 1 and R 3 may be the same or different.
• n1 and n2 may be the same or different.
• phosphoric acid ester represented by formula (1) (C1) may be used as a mixture of different ones R 1 2 or more, monoester (R 2 is H) and diester (R 2 is - A mixture of (A 2 O) n2 R 3 ) may be used.
• the phosphoric acid ester (C1) represented by the general formula (1) is generally obtained as a mixture of a monoester and a diester (mono-di mixture).
• a salt of a phosphoric acid ester represented by the general formula (1) metal salt such as sodium, potassium and magnesium, ammonium salt, etc.
• metal salt such as sodium, potassium and magnesium, ammonium salt, etc.
• Preferred examples of the phosphoric acid ester (C1) represented by the general formula (1) include an alkyl ether phosphoric acid ester, an alkyl phosphoric acid ester and the like, and an alkyl ether phosphoric acid ester is more preferable.
• the phosphoric acid ester (C1) represented by the general formula (1) can be obtained by phosphorylation with a polyether and phosphor oxide, and is also available on the market at Disparon DA-375 [manufactured by Kusumoto Kasei Co., Ltd.].
• Plysurf A208N [Daiichi Kogyo Seiyaku Co., Ltd.], Phosphanol RL-210 [manufactured by Toho Chemical Industry Co., Ltd., R 1, R 3: C 18 H 37, mono-di- mixture, n1, n2: 2 ], Phosphanol RS-710 [manufactured by Toho Chemical Industry Co., Ltd., R 1 , R 3 : C12-15 alkyl group, mono-dimixture, n1, n2: 9], Phosphanol RS-410 [ manufactured by Toho Chemical Industry Co., Ltd., R 1, R 3: an alkyl group of C12 ⁇ 15, mono-di- mixture, n1, n2: available as 3], and the like.
• Examples of the fatty acid (C2) having 12 to 24 carbon atoms include saturated fatty acids having 12 to 24 carbon atoms (dodecanoic acid, hexadecanoic acid, eicosanoic acid, tetracosanoic acid, etc.) and unsaturated fatty acids having 12 to 24 carbon atoms (hexadecenoic acid, octadecene). Acids, octadecandienic acid, etc.) and the like, and hexadecenoic acid (oleic acid) is preferable.
• sucrose fatty acid ester (C3) examples include an ester of sucrose and a fatty acid having 8 to 22 carbon atoms.
• sucrose fatty acid ester (C3) the sorbitan fatty acid ester (C4) and the glycerin fatty acid ester (C5)
• the sorbitan fatty acid ester (C4) is preferable, and the sorbitan oleic acid monoester is more preferable.
• the ratio of the total weight of the phosphoric acid ester (C1) and the fatty acid (C2) having 12 to 24 carbon atoms is based on the weight of the curable composition from the viewpoint of dispersibility and moldability of the inorganic filler (D). It is preferably 1 to 5% by weight, more preferably 1 to 3% by weight, still more preferably 1 to 2% by weight.
• the ratio of the total weight of the sucrose fatty acid ester (C3), the sorbitan fatty acid ester (C4) and the glycerin fatty acid ester (C5) is the weight of the curable composition from the viewpoint of dispersibility and moldability of the inorganic filler (D). It is preferably 1 to 5% by weight, more preferably 1 to 3% by weight, still more preferably 1 to 2% by weight.
• the dispersant (C) for the inorganic filler is at least one selected from the group consisting of a phosphate ester (C1) and a fatty acid (C2) having 12 to 24 carbon atoms. And at least one selected from the group consisting of sucrose fatty acid ester (C3), sorbitan fatty acid ester (C4) and glycerin fatty acid ester (C5).
• the total weight of the dispersant (C) for an inorganic filler is 1 to 5 parts by weight, preferably 1 to 3 parts by weight, and more preferably 1 to 2 parts by weight with respect to 100 parts by weight of the inorganic filler (D). ..
• the total weight of the dispersant (C) for the inorganic filler is 1 to 5 parts by weight with respect to 100 parts by weight of the inorganic filler (D)
• the dispersibility of the inorganic filler (D) is excellent and the moldability is excellent. ..
• the ratio is less than 1 part by weight, the dispersibility of the inorganic filler may be deteriorated, and if the ratio is more than 5 parts by weight, the moldability may be deteriorated.
• Examples of the inorganic filler (D) include silicates (talc, clay, mica, glass, etc.), metal oxides (titanium oxide, alumina, silica, magnesium oxide, etc.), and metal carbonates (calcium carbonate, magnesium carbonate, etc.). , And hydrotalcite, etc.), metal hydroxides (aluminum hydroxide, magnesium hydroxide, calcium hydroxide, etc.), metal (sub) sulfates (barium sulfate, calcium sulfate, calcium sulfite, etc.), metal boric acid, etc.
• silicates talc, clay, mica, glass, etc.
• metal oxides titanium oxide, alumina, silica, magnesium oxide, etc.
• metal carbonates calcium carbonate, magnesium carbonate, etc.
• metal hydroxides aluminum hydroxide, magnesium hydroxide, calcium hydroxide, etc.
• metal (sub) sulfates barium sulfate, calcium sulfate,
• an inorganic filler having a thermal conductivity of 0.5 to 200 W / m ⁇ K (more preferably 1 to 200 W / m ⁇ K, particularly preferably 10 to 200 W / m ⁇ K) is preferably used.
• the thermal conductivity of the inorganic filler is within the above range, the cured product of the curable composition can be preferably used as a heat radiating member.
• the inorganic filler (D) is preferably a metal, a metal oxide, a metal nitride, or metal water. Oxides and metal carbonates, more preferred are metal oxides, and particularly preferred are magnesium oxide and alumina. These may be used alone or in combination of two or more.
• the shape of the inorganic filler (D) is not particularly limited, and fibrous and particulate ones can be preferably used. In the case of particles, spherical, plate-shaped, needle-shaped or amorphous (obtained by crushing or the like) particles or the like can be used. From the viewpoint of excellent moldability, spherical particles are preferable as the shape of the inorganic filler (D).
• the volume average particle diameter of the inorganic filler (D) [D50: the particle diameter at which the integrated particle amount in the particle size distribution on a volume basis is 50%] has a formability. From the viewpoint of superiority and the like, it is preferably 0.01 to 200 ⁇ m, and more preferably 0.1 to 150 ⁇ m.
• the volume average particle size of the inorganic filler (D) can be measured using a laser diffraction type particle size distribution measuring device [SALD-2000A manufactured by Shimadzu Corporation, LA-920 manufactured by HORIBA, Ltd., etc.]. can. When the components other than the inorganic filler (D) are dissolved in the solvent, the solution of the composition may be measured.
• the inorganic filler (D) contained in the curable composition has a particle size distribution curve (volume basis, volume standard, obtained from measurement by a laser diffraction type particle size distribution measuring device).
• Horizontal axis log particle size [ ⁇ m]
• vertical axis frequency [%])
• the total frequency is more preferably 10% or less, and particularly preferably 1 to 5.5%.
• the total frequency of particles with a particle size of 1 ⁇ m or less is the sum of the frequencies of each particle size with a particle size of 1 ⁇ m or less in the particle size distribution curve (volume basis, horizontal axis: log particle size [ ⁇ m], vertical axis: frequency [%]). That is, the cumulative frequency at a particle size of 1 ⁇ m.
• an inorganic filler (D) a mixture of two or more kinds of inorganic fillers having different volume average particle diameters may be used.
• the inorganic filler having a volume average particle diameter of less than 1 ⁇ m is preferably contained in an amount of 1 to 10% by weight based on the total weight of the inorganic filler (D). It is more preferable to contain 3 to 7% by weight. Further, as the inorganic filler having a volume average particle diameter of 1 ⁇ m or more, an inorganic filler (Da) having a volume average particle diameter of 1 to 10 ⁇ m and an inorganic filler (Db) having a volume average particle diameter of 10 to 100 ⁇ m are included.
• the inorganic filler (Da) and the inorganic filler (Db) are preferably Da: Db from 10:90 to 90:10 (more preferably 20:80 to 80:20, and particularly preferably 30:70 to 20). It is preferably contained in a weight ratio of 70:30).
• the curable composition contains the inorganic filler (D) in an amount of 70 to 97% by weight, preferably 80 to 97% by weight, based on the weight of the curable composition.
• the content of the inorganic filler (D) is 70% by weight or more, the thermal conductivity of the cured product of the curable composition is good, and when it is 97% by weight or less, the moldability is good. Can be. If the content of the inorganic filler (D) is less than 70% by weight, the thermal conductivity of the cured product may be insufficient, and if it exceeds 97% by weight, the moldability may be deteriorated.
• the curable composition of the first aspect contains a polyol (A), a polyisocyanate (B), a dispersant for an inorganic filler (C), and other components not corresponding to the inorganic filler (D). good.
• the other component include a surfactant (E), a plasticizer (F), and a urethanization catalyst (G).
• the curable composition may further contain, as other components, known additives used for urethane resins (antioxidants and ultraviolet absorbers described in JP-A-2018-076537).
• surfactant (E) examples include a polyoxyalkylene type nonionic surfactant (E1), an ester type nonionic surfactant (E2), an anionic surfactant (E3) and a cationic surfactant (E4). Can be preferably used.
• Examples of the polyoxyalkylene type nonionic surfactant (E1) include aliphatic alcohols (4 to 30 carbon atoms), alkyl (1 to 30 carbon atoms) phenols, aliphatic (4 to 30 carbon atoms) amines, and aliphatic (4 to 30 carbon atoms) amines. Examples thereof include an AO adduct of an amide having 4 to 30 carbon atoms (preferable addition molars are 1 to 30).
• the aliphatic alcohol constituting the polyoxyalkylene type nonionic surfactant (E1) is preferably n-, i-, sec- or t-butanol, octanol, dodecanol and the like, and the alkylphenol is phenol, methylphenol and the like.
• nonylphenol and the like are preferable, as the aliphatic amine, laurylamine and methylstearylamine are preferable, and as the aliphatic amide, stearic acid amide and the like are preferable.
• ester-type nonionic surfactant (E2) examples include ester compounds of fatty acids having 4 to 30 carbon atoms (lauric acid, stearic acid, oleic acid, etc.) and polyhydric alcohols other than sucrose, sorbitol, and glycerin. Can be mentioned.
• Examples of the anionic surfactant (E3) include a carboxylate type, a sulfate ester type and a sulfonate type.
• Examples of the carboxylate type include alkali metal salts of the fatty acids having 4 to 30 carbon atoms and alkali metal salts of polyoxyalkylene alkyl ether carboxylic acids
• examples of the sulfate ester type include the alkali metal salts having 4 to 30 carbon atoms.
• Examples thereof include an aliphatic alcohol or a sulfate ester alkali metal salt of an AO adduct of an aliphatic alcohol
• examples of the sulfonate type include a sulfonic acid alkali metal salt of an alkylphenol. It can also be obtained from the market as a polyether carboxylic acid [Kao Corporation, Kao Akipo RLM-100] or the like.
• Examples of the cationic surfactant (E4) include primary to tertiary amine salt types and quaternary ammonium salt types.
• Examples of the 1st to 3rd grade amine salt type include aliphatic amines having 4 to 30 carbon atoms [primary (laurylamine, etc.), secondary (dibutylamine, etc.) and tertiary amines (dimethylstearylamine, etc.)] hydrochloride, and the like.
• Examples thereof include inorganic acid (hydrochloride, sulfuric acid, nitrate, phosphoric acid, etc.) salts of triethanolamine and monoesters of fatty acids having 4 to 30 carbon atoms, and examples of the quaternary ammonium salt type are quaternary salts having 4 to 30 carbon atoms.
• examples thereof include inorganic acid salts of ammonium (butyltrimethylammonium, diethyllaurylmethylammonium, dimethyldistearylammonium, etc.). It can also be obtained from the market as Nopcos Perth 092 [manufactured by San Nopco Ltd., cationic surfactant] and the like.
• plasticizer (F) examples include phthalic acid-based plasticizers [diisononylphthalate, di- (2-ethylhexyl) phthalate, diisodecylphthalate, butylbenzylphthalate, etc.], fatty acid ester-based plasticizers [di- (2-ethylhexyl) adipate, etc.].
• urethanization catalyst (G) examples include amine catalysts [triethylenediamine, N-ethylmorpholin, diethylethanolamine and 1,8-diazabicyclo (5,4,0) undecene-7, etc.] and metal catalysts [bismastris (2-). Ethylhexanoate), stannous octylate, dibutyltin dilaurate, lead octylate, etc.] and the like. It can also be obtained from the market as an inorganic bismuth catalyst [Nitto Kasei Co., Ltd., Neostan U-600] and the like.
• the curable composition of the first aspect contains the surfactant (E), it contains 0.001 to 30 parts by weight of the surfactant (E) with respect to 100 parts by weight of the inorganic filler (D). It is preferable, more preferably 0.01 to 10 parts by weight, and particularly preferably 0.1 to 5 parts by weight.
• the amount of the plasticizer (F) is 25 parts by weight or less based on 100 parts by weight of the total weight of the polyol (A) and the polyisocyanate (B). It is preferably 1 to 25 parts by weight, and particularly preferably 5 to 20 parts by weight.
• the amount of the urethanization catalyst (G) is 3 parts by weight or less based on the total weight of the polyol (A) and the polyisocyanate (B) of 100% by weight. It is preferably 0.001 to 3 parts by weight, and particularly preferably 0.005 to 3 parts by weight.
• the curable composition of the first aspect comprises a polyol (A), a polyisocyanate (B), a dispersant for an inorganic filler (C) and an inorganic filler (D), and other components (surfactant) used as necessary.
• (E), plasticizer (F), urethanization catalyst (G), etc.) are uniformly mixed using a known mixing device (mixing tank with a stirring device, etc.).
• each component may be mixed in a batch, or any two or more components may be mixed in advance and the remaining components (the remaining components may be a mixture) are mixed. You may.
• a cured product can be obtained by subjecting the curable composition of the first aspect to a urethanization reaction on an arbitrary substrate or in a molding having a shape according to a purpose by a known method.
• the components of the polyol (A), the polyisocyanate (B), the dispersant (C) for an inorganic filler and the inorganic filler (D) are contained in the first agent and the second agent. Included in two parts.
• the second aspect is preferable from the viewpoint that the composition immediately after mixing the first agent and the second agent has low fluidity and high adhesion to the substrate.
• the inorganic filler (D) is contained in the first inorganic filler (D1) contained in the first agent and the second agent. It consists of two inorganic fillers (D2), the first agent contains a polyol (A), a dispersant for inorganic fillers (C), and a first inorganic filler (D1), and the second agent is.
• An embodiment containing a polyisocyanate (B) and a second inorganic filler (D2) can be mentioned.
• the second aspect will be described with a focus on the aspect A.
• the polyol (A), the dispersant for an inorganic filler (C), and the first inorganic filler (D1) contained in the first agent will be described in the first aspect.
• the same ones as the above-mentioned polyol (A), the dispersant for inorganic filler (C), and the inorganic filler (D) can be used, and the preferred ones are also the same.
• the weight ratio of the polyalkylene glycol (A1) contained in the polyol (A) is 50% by weight or more, preferably 70 to 100% by weight, more preferably 70% by weight, based on the weight of the polyol (A). It is preferably 90 to 100% by weight.
• the weight ratio of the polyalkylene glycol (A1) in the polyol (A) is 50% by weight or more, the content of the inorganic filler in the curable composition can be increased, and the cured product of the curable composition can be obtained. It can be easily obtained.
• the weight ratio of the polyalkylene glycol (A1) contained in the polyol (A) is less than 50% by weight based on the weight of the polyol (A)
• the content of the inorganic filler in the curable composition is increased. And it becomes difficult to obtain a cured product of the curable composition.
• the total weight of the dispersant (C) for the inorganic filler is 1 to 5 parts by weight, preferably 1 to 3 parts by weight, based on 100 parts by weight of the total of the inorganic filler (D). , More preferably 1 to 2 parts by weight.
• the total weight of the dispersant (C) for the inorganic filler is 1 to 5 parts by weight with respect to 100 parts by weight of the inorganic filler (D)
• the dispersibility of the inorganic filler is excellent and the moldability is excellent. If the weight is less than 1 part by weight, the dispersibility of the inorganic filler may be deteriorated, and if it exceeds 5 parts by weight, the moldability may be deteriorated.
• the curable composition contains the inorganic filler (D) in an amount of 70 to 97% by weight, preferably 80 to 97% by weight, based on the weight of the curable composition.
• the content of the inorganic filler (D) is 70% by weight or more, the thermal conductivity of the cured product of the curable composition is good, and when it is 97% by weight or less, the moldability is good. Can be. If the content of the inorganic filler (D) is less than 70% by weight, the thermal conductivity of the cured product may be insufficient, and if it exceeds 97% by weight, the moldability may be deteriorated.
• the weight of the curable composition means the total weight of the first agent and the second agent.
• the content of the first inorganic filler (D1) in the first agent is preferably 70 to 97% by weight, more preferably 80 to 97% by weight, still more preferably 85 to 85% based on the weight of the first agent. It is 95% by weight.
• the content of the first inorganic filler (D1) in the first agent is 70% by weight or more, the heat conduction of the cured product obtained after mixing and curing the first agent and the second agent. The sex can be made better.
• the content of the first inorganic filler (D1) in the first agent is 97% by weight or less, the flexibility of the cured product obtained after mixing and curing the first agent and the second agent. Can be made better.
• the ratio of the total weight of the phosphate ester (C1) and the fatty acid (C2) having 12 to 24 carbon atoms is based on the weight of the curable composition (that is, the total weight of the first agent and the second agent). It is preferably 1 to 5% by weight, more preferably 1 to 3% by weight, still more preferably 1 to 2% by weight.
• the ratio is 1% by weight or more, the dispersibility of the inorganic filler (D) can be improved, and when it is 5% by weight or less, the curing obtained after mixing with the second agent and curing is obtained.
• the formability of the object can be improved.
• the ratio of the total weight of the sucrose fatty acid ester (C3), the sorbitan fatty acid ester (C4) and the glycerin fatty acid ester (C5) is the weight of the curable composition (that is, the total weight of the first agent and the weight of the second agent). ), It is preferably 1 to 5% by weight, more preferably 1 to 3% by weight, and further preferably 1 to 2% by weight.
• the ratio is 1% by weight or more, the dispersibility of the inorganic filler (D) can be improved, and when it is 5% by weight or less, the curing obtained after mixing with the second agent and curing is obtained.
• the formability of the object can be improved.
• the dispersant (C) for the inorganic filler is composed of a phosphate ester (C1) and a fatty acid (C2) having 12 to 24 carbon atoms. It is preferable to include at least one selected from the group and at least one selected from the group consisting of sucrose fatty acid ester (C3), sorbitan fatty acid ester (C4) and glycerin fatty acid ester (C5).
• the total weight of the dispersant (C) for an inorganic filler contained in the first agent is preferably 1 to 8 parts by weight, more preferably 1 to 6 parts by weight with respect to 100 parts by weight of the first inorganic filler (D1). It is by weight, more preferably 1 to 5 parts by weight.
• the total weight of the dispersant (C) for the inorganic filler is 1 part by weight or more with respect to 100 parts by weight of the first inorganic filler (D1), the dispersibility of the inorganic filler (D) is improved.
• the thermal conductivity and moldability of the cured product obtained after mixing with the two agents and curing can be improved.
• the cured product obtained after mixing with the second agent and curing is obtained.
• the strength can be further improved.
• the same polyisocyanate (B) and the second inorganic filler (D2) contained in the second agent can be used.
• the preferred ones are the same.
• the first inorganic filler (D1) and the second inorganic filler (D2) may be the same or different.
• the difference between the first inorganic filler (D1) and the second inorganic filler (D2) is that the first inorganic filler (D1) and the second inorganic filler (D2) are two or more kinds of inorganic materials, respectively. Including those that differ only in the compounding ratio when they are made of filler.
• the content of the second inorganic filler (D2) in the second agent is preferably 70 to 97% by weight, more preferably 80 to 95% by weight, still more preferably 85 to 85% based on the weight of the second agent. It is 95% by weight.
• the content of the second inorganic filler (D2) in the second agent is 70% by weight or more, the thermal conductivity of the cured product obtained by mixing and curing the first agent and the second agent is further improved. It can be good.
• the content of the second inorganic filler (D2) in the second agent is 97% by weight or less, the flexibility of the cured product obtained after mixing and curing the first agent and the second agent is increased. It can be better.
• the isocyanate index of the polyol (A) contained in the first agent and the polyisocyanate (B) contained in the second agent is preferably 0.2 to 1.0, preferably 0.5 to 0.8. Is more preferable. Within this range, the curability of the curable composition and the flexibility of the cured product are good.
• the ratio of the total weight of the polyol (A) and the polyisocyanate (B) is preferably 3 to 30% by weight based on the weight of the curable composition (that is, the total weight of the first agent and the second agent). More preferably, it is 3 to 20% by weight.
• the weight ratio of the second agent to the first agent is preferably 1/10 to 10/1, more preferably 1/4 to 4 /. 1, more preferably 1/3 to 2/1.
• the weight ratio of the second agent to the first agent is 1/10 or more, the strength of the cured product obtained by mixing the first agent and the second agent is good.
• the weight ratio is 10/1 or less, the curability of the cured product can be improved.
• the first agent and the second agent are the polyol (A), the polyisocyanate (B), the dispersant for an inorganic filler (C) and the inorganic filler (D) exemplified in the description of the curable composition of the first aspect.
• Other components surfactant (E), plasticizer (F), urethanization catalyst (G), etc. may be contained.
• the total amount of the surfactant (E) is 0.001 with respect to 100 parts by weight of the inorganic filler (D) in the curable composition. It is preferably contained in an amount of up to 30 parts by weight, more preferably 0.01 to 10 parts by weight, and particularly preferably 0.1 to 5 parts by weight.
• the total weight of the plasticizer (F) is 25 parts by weight with respect to 100 parts by weight of the total weight of the polyol (A) and the polyisocyanate (B). It is preferably the following, more preferably 1 to 25 parts by weight, and particularly preferably 5 to 20 parts by weight.
• the total weight of the urethanization catalyst (G) is 3 parts by weight based on the total weight of the polyol (A) and the polyisocyanate (B) of 100 weight. It is preferably the following, more preferably 0.001 to 3 parts by weight, and particularly preferably 0.005 to 3 parts by weight.
• the first agent is a polyol (A), a dispersant (C) for an inorganic filler and a first inorganic filler (D1), and other components used as necessary (surfactant (E), plasticizer).
• the agent (F), the urethanization catalyst (G), etc.) are uniformly mixed using a known mixing device (mixing tank with a stirring device, etc.). Each component may be mixed at once, or any two or more components may be mixed in advance and the remaining components (the remaining components may be a mixture) may be mixed.
• the second agent is a polyisocyanate (B) and a second inorganic filler (D2), as well as other components used as needed (surfactant (E), plasticizer (F) and urethanization catalyst (. G), etc.) can be obtained by uniformly mixing using a known mixing device (mixing tank with a stirring device, etc.). Each component may be mixed at once, or any two or more components may be mixed in advance and the remaining components (the remaining components may be a mixture) may be mixed.
• a known mixing device mixing tank with a stirring device, etc.
• the first agent and the second agent are mixed and subjected to a urethanization reaction by a known method on an arbitrary substrate or in a molding having a shape according to a purpose.
• a cured product can be obtained with.
• the first agent and the second agent may be mixed manually or by a known mixing device (such as a container with a stirring device), or may be continuously mixed using a known two-component mixing and feeding device. ..
• the urethane resin of the present invention is obtained by reacting the curable composition of the present invention.
• the urethane resin of the present invention is a urethane resin obtained by curing the curable composition of the first or second aspect described above by a known method.
• the urethane resin of the present invention is a urethane resin containing an inorganic filler (D) and having excellent flexibility. Therefore, according to the urethane resin of the present invention, functions corresponding to the functions of the inorganic filler (D) such as electromagnetic wave shielding, semiconductor elements (CPU, etc.), LED backlights, batteries, etc. are exhibited without being limited by the shape. can do. Among them, by using an inorganic filler selected from the group consisting of metals, metal oxides, metal nitrides, metal hydroxides and metal carbonates as the inorganic filler (D), the flexibility and thermal conductivity of the urethane resin can be obtained. The sex can be made better.
• the shape of the urethane resin is in the form of a film such as a film or a sheet. Is preferable.
• the heat radiating member of the present invention contains the urethane resin of the present invention.
• the heat-dissipating member of the present invention may include the urethane resin of the present invention and the heat-receiving member, or the urethane resin of the present invention itself may be used as the heat-dissipating member.
• the heat radiating member of the present invention includes the urethane resin of the present invention and the heat receiving member
• the heat receiving member is made of gold, silver, copper, aluminum, nickel, iron, tin, an alloy thereof, or the like. Examples thereof include a sheet-shaped base material and a graphite sheet. From the viewpoint of heat dissipation, the heat radiating member of the present invention preferably has the urethane resin of the present invention and the heat receiving member adhered to each other.
• the heat-dissipating member of the present invention comprises the urethane resin of the present invention and the heat-receiving member
• the heat-dissipating member is a method of applying the curable composition of the present invention onto the heat-receiving member and curing the film. It can be manufactured by a method of laminating and adhering the urethane resin of the present invention molded into a shape and a heat receiving member.
• a known adhesive or the like may be used to bond the urethane resin to the heat receiving member, and if the surface of the urethane resin has adhesiveness, the adhesiveness of the urethane resin itself does not use an adhesive or the like.
• the heat receiving member may be adhered to the contact surface.
• the heat radiating member of the present invention can be used for cooling the heat generating member.
• the heat generating member is a member to be cooled by the heat radiating member, and specific examples thereof include a semiconductor element (CPU or the like), an LED backlight, a battery, and an electric circuit provided with these.
• the heat-dissipating member made of the urethane resin of the present invention is used for cooling the heat-generating member, it is preferable that the heat-dissipating member of the present invention and the heat-generating member are adhered from the viewpoint of heat dissipation. ..
• the mode in which the heat radiating member and the heat generating member are adhered to each other is a method of applying the curable composition of the present invention on the heat generating member to cure the heat radiating member, and the urethane resin of the present invention molded into a film shape and the heat generating member. Can be manufactured by a method of laminating and adhering the above.
• a known adhesive or the like may be used to bond the urethane resin to the heat generating member, and if the surface of the urethane resin has adhesiveness, the adhesiveness of the urethane resin itself is not used. Depending on the property, the heat generating member may be adhered to the contact surface.
• the heat radiating member includes the urethane resin of the present invention and the heat receiving member
• the heat generating member and the heat receiving member are adhered to each other via the urethane resin of the present invention.
• a heat receiving member is adhered to one side or both sides of a heat generating member such as an electric circuit via a urethane resin can be mentioned.
• the urethane resin sheets of Examples 6 to 10 were obtained from the compositions of Examples 1 to 5, and the urethane resin sheets of Comparative Example 6 were obtained from the compositions of Comparative Example 3.
• Comparative Example 4 using the composition of Comparative Example 1 and Comparative Example 5 using the composition of Comparative Example 2, molding was not possible and a urethane resin sheet could not be obtained.
• the molded products (urethane resin sheets of Examples 6 to 10 and urethane resin sheets of Comparative Example 6) were evaluated for thermal conductivity and flexibility by the following methods. The results are shown in Table 2. As for Comparative Examples 4 and 5, the resin sheet could not be obtained as described above, and the thermal conductivity and flexibility could not be measured. Therefore, Table 2 shows “not measurable”.
• the urethane resin sheets of Examples 16 to 20 were obtained from the compositions of Examples 11 to 15, and the urethane resin sheets of Comparative Example 12 were obtained from the compositions of Comparative Example 9.
• Comparative Example 10 using the composition of Comparative Example 7 and Comparative Example 11 using the composition of Comparative Example 8 molding was not possible and a urethane resin sheet could not be obtained.
• the molded products (urethane resin sheets of Examples 16 to 20 and urethane resin sheets of Comparative Example 12) were evaluated for thermal conductivity and flexibility by the following methods. The results are shown in Table 3. As for Comparative Examples 10 and 11, since the resin sheet could not be obtained as described above and the thermal conductivity and the flexibility could not be measured, it was indicated as “not measurable” in Table 3.
• the frequencies of particles having a particle size of 1 ⁇ m or less were totaled, and the total frequency of particles having a particle size of 1 ⁇ m or less (cumulative frequency at a particle size of 1 ⁇ m) was calculated.
• thermo conductivity (unit) is measured by a laser flash method using a thermal conductivity meter "xenon flash analyzer LFA447 NanoFlash, manufactured by Netch Japan Co., Ltd.” : W / m ⁇ K) was measured.
• the urethane resin sheets of Examples 6 to 10 produced using the compositions of Examples 1 to 5 have higher thermal conductivity than the urethane resin sheets of Comparative Example 6 produced using the composition of Comparative Example 3. And it was excellent in flexibility. Further, the urethane resin sheets of Examples 16 to 20 manufactured using the compositions of Examples 11 to 15 have higher thermal conductivity than the urethane resin sheets of Comparative Example 12 manufactured using the composition of Comparative Example 9. It was expensive and had excellent flexibility. From these results, it was found that the curable composition of the present invention can provide a urethane resin having excellent thermal conductivity and excellent flexibility, and a heat radiating member.

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• 2021
  • 2021-06-23 CN CN202180044919.9A patent/CN115768810A/zh active Pending
  • 2021-06-23 US US18/010,053 patent/US12516190B2/en active Active
  • 2021-06-23 WO PCT/JP2021/023790 patent/WO2021261519A1/ja not_active Ceased
  • 2021-06-23 JP JP2022501275A patent/JP7285368B2/ja active Active
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