Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • 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
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/44—Polycarbonates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets
• • 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
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
• • 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
  • C08K7/00—Use of ingredients characterised by shape
  • C08K7/16—Solid spheres
  • C08K7/18—Solid spheres inorganic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
  • C08L75/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • 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

Definitions

• the present disclosure relates to a thermally conductive resin composition and its cured product, as well as a thermally conductive sheet and a method for producing the same.
• thermoly conductive sheet between the heat generating member and the cooling member in order to facilitate heat transfer from the heat generating member to the cooling member in these products.
• the thermally conductive sheet is sometimes required to be flexible in order to reduce thermal resistance (contact resistance) by increasing adhesion to the heat generating member and the cooling member (for example, Patent Document 1 (Patent No. 6732145)).
• Patent Document 2 Patent No. 5989219 describes the use of a sealing material with excellent heat dissipation and flexibility for electrical and electronic components that generate heat.
• the thermally conductive sheet described in Patent Document 1 and the sealing material described in Patent Document 2 contain a filler. Fillers are sometimes used for the purpose of improving electrical insulation and thermal conductivity. When the content of the filler in the thermally conductive sheet and the encapsulating material is increased in order to improve the thermal conductivity, the hardness of the thermally conductive sheet and the encapsulating material increases, and the flexibility may decrease. In addition, thermally conductive sheets and sealing materials are required to have excellent heat resistance that can withstand use under high temperature conditions.
• An object of the present disclosure is to provide a thermally conductive resin composition capable of obtaining a cured product having excellent flexibility, excellent thermal conductivity, and excellent heat resistance, and a thermally conductive sheet containing the same. .
• the thermally conductive resin composition of the present disclosure contains a polycarbonate polyol compound (A) having a hydroxyl equivalent of 200 g/eq to 800 g/eq, a polyisocyanate compound (B), and a spherical alumina filler (C), and a plasticizer (D) may be included.
• A polycarbonate polyol compound having a hydroxyl equivalent of 200 g/eq to 800 g/eq
• B polyisocyanate compound
• C spherical alumina filler
• D plasticizer
• the equivalent ratio (isocyanate group/hydroxyl group) of the isocyanate group in the polyisocyanate compound (B) to the hydroxyl group in the polycarbonate polyol compound (A) is 0.26 or more and 0.40 or less.
• the content of the spherical alumina filler (C) is , 400 parts by mass or more and 900 parts by mass or less, and the content of the plasticizer (D) is 30 parts by mass or less.
• thermally conductive resin composition of the present disclosure it is possible to provide a cured product having excellent flexibility, excellent thermal conductivity, and excellent heat resistance, and a thermally conductive sheet containing the cured product.
• Embodiment 1 The thermally conductive resin composition of the present embodiment (hereinafter sometimes referred to as "this composition") comprises a polycarbonate polyol compound (A), a polyisocyanate compound (B), and a spherical alumina filler (C). and may contain a plasticizer (D).
• the composition may further contain one or more components other than the polycarbonate polyol compound (A), the polyisocyanate compound (B), the spherical alumina filler (C), and the plasticizer (D).
• Polycarbonate polyol compound (A) The composition contains a polycarbonate polyol compound (A) (hereinafter sometimes referred to as "polyol compound (A)").
• the hydroxyl equivalent of the polyol compound (A) is 200 g/eq or more and 800 g/eq or less.
• the polyol compound (A) contained in the present composition may be one kind or two or more kinds.
• the polyol compound (A) is a compound having two or more hydroxyl groups in one molecule and a polycarbonate structure in the molecule.
• the hydroxyl groups contained in the polyol compound (A) react with the isocyanate groups contained in the polyisocyanate compound (B) to form urethane bonds.
• a crosslinked structure can be introduced into the cured product of the present composition, so that the cured product obtained using the present composition can have excellent electrical insulation and excellent heat resistance.
• the number of hydroxyl groups contained in the polyol compound (A) is not particularly limited as long as it is 2 or more per molecule, but 2 is preferred.
• the number of hydroxyl groups per molecule contained in the polyol compound (A) increases, the crosslink density of the cured product of the present composition tends to increase, the hardness of the cured product increases, and the flexibility of the cured product tends to decrease. It is in.
• the number of hydroxyl groups per molecule contained in the polyol compound (A) decreases, the cross-linking reaction between the hydroxyl groups and the isocyanate groups tends to proceed more slowly, making it difficult to sufficiently cure the present composition.
• Hardness in this specification refers to Asker C hardness.
• the hydroxyl equivalent of the polyol compound (A) is 200 g/eq or more, preferably 300 g/eq or more, may be 350 g/eq or more, and is 800 g/eq or less and 700 g/eq or less. and may be 650 g/eq or less.
• the hydroxyl equivalent of the polyol compound (A) is reduced, the crosslink density of the cured product of the composition tends to increase, the hardness of the cured product increases, and the flexibility of the cured product tends to decrease.
• the hydroxyl equivalent of the polyol compound (A) increases, the cross-linking reaction between the hydroxyl groups and the isocyanate groups becomes difficult to proceed, and the present composition tends to be difficult to sufficiently cure.
• the hydroxyl group equivalent of the polyol compound (A) can be measured by the method described in Examples below.
• the polycarbonate structure contained in the polyol compound (A) is a structure having polymer chains bonded via carbonate bonds.
• the polycarbonate structure is contained in the polyol compound (A).
• the polycarbonate structure is preferably contained in the main chain structure of the polyol compound (A), and more preferably the main chain structure is the polycarbonate structure.
• a known compound can be used as the polyol compound (A).
• a reaction product of a compound having two or more hydroxyl groups in one molecule and at least one of carbonate ester and phosgene can be used.
• compounds having two or more hydroxyl groups in one molecule include ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-ethyl-2-butyl-1,3 -propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-pentanediol, 1,7-heptanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,8-nonanediol, 1,10-de
• Carbonic acid esters include, for example, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate, ethylbutyl carbonate, ethylene carbonate, propylene carbonate, diphenyl carbonate, dibenzyl carbonate and the like.
• the content of the polyol compound (A) in the composition can be adjusted by the types of the polyol compound (A) and the polyisocyanate compound (B) contained in the composition.
• the content of the polyol compound (A) in the composition is, for example, 40 parts by mass or more with respect to 100 parts by mass of the total amount of the polyol compound (A), the polyisocyanate compound (B), and the plasticizer (D). It may be 50 parts by mass or more, may be 60 parts by mass or more, may be 90 parts by mass or less, may be 80 parts by mass or less, or may be 70 parts by mass It may be below.
• the composition contains a polyisocyanate compound (B).
• the polyisocyanate compound (B) is a compound having two or more isocyanate groups in one molecule.
• the polyisocyanate compound (B) contained in the present composition may be one kind or two or more kinds.
• the isocyanate groups contained in the polyisocyanate compound (B) react with the hydroxyl groups contained in the polyol compound (A) to form urethane bonds.
• a crosslinked structure can be introduced into the cured product of the present composition, so that the cured product can have excellent electrical insulation and excellent heat resistance.
• the number of isocyanate groups contained in the polyisocyanate compound (B) is not particularly limited as long as it is 2 or more per molecule, but 3 is preferred.
• the number of isocyanate groups per molecule contained in the polyisocyanate compound (B) increases, the crosslink density of the cured product of the present composition tends to increase, so the hardness of the cured product increases and the flexibility of the cured product increases. tend to decline.
• the number of isocyanate groups per molecule contained in the polyisocyanate compound (B) is reduced, the cross-linking reaction between the hydroxyl groups and the isocyanate groups becomes difficult to proceed, and the composition tends to be difficult to sufficiently cure.
• a known compound can be used as the polyisocyanate compound (B), and examples thereof include aliphatic polyisocyanate compounds, alicyclic polyisocyanate compounds, aromatic polyisocyanate compounds, isocyanurate-type polyisocyanate compounds, and the like.
• the polyisocyanate compound (B) is preferably an isocyanurate-type polyisocyanate compound.
• the isocyanate group equivalent of the polyisocyanate compound (B) may be, for example, 52 g/eq or more, 80 g/eq or more, 100 g/eq or more, or 120 g/eq or more. It may be 320 g/eq or less, 250 g/eq or less, or 200 g/eq or less.
• the isocyanate group equivalent of the polyisocyanate compound (B) can be measured by the method described in Examples below.
• the content of the polyisocyanate compound (B) in the composition can be adjusted by the types of the polyol compound (A) and the polyisocyanate compound (B) contained in the composition.
• the content of the polyol compound (A) in the composition is, for example, 1 part by mass or more with respect to 100 parts by mass of the total amount of the polyol compound (A), the polyisocyanate compound (B), and the plasticizer (D). It may be 3 parts by mass or more, may be 5 parts by mass or more, may be 25 parts by mass or less, may be 20 parts by mass or less, or may be 15 parts by mass It may be below.
• composition composition of polyol compound (A) and polyisocyanate compound (B)
• content of the polyol compound (A) and the polyisocyanate compound (B) in the present composition is such that the equivalent ratio (isocyanate group/hydroxyl group) of the isocyanate group in the polyisocyanate compound (B) to the hydroxyl group in the polyol compound (A) is , 0.26 or more and 0.40 or less.
• the equivalent ratio may be 0.30 or more, or may be 0.35 or less.
• the flexibility of the cured product obtained using the present composition can be improved.
• the content of the spherical alumina filler (C) in the present composition is increased, the increase in hardness of the cured product is suppressed, resulting in a cured product with excellent flexibility. Obtainable.
• the equivalent ratio is large, the hardness of the cured product increases and the flexibility of the cured product tends to decrease.
• the composition contains a spherical alumina filler (C) (hereinafter sometimes referred to as "filler (C)").
• the content of the filler (C) in the present composition is 400 parts by mass or more and 900 parts by mass or less with respect to 100 parts by mass of the total amount of the polyol compound (A), the polyisocyanate compound (B), and the plasticizer (D). is.
• the filler (C) is composed of alumina (aluminum oxide), it has electrical insulation and excellent thermal conductivity. Therefore, the cured product obtained using the present composition containing the filler (C) can have excellent thermal conductivity and excellent electrical insulation.
• the filler (C) is spherical.
• Spherical in the present specification means that the average sphericity is 0.80 or more.
• the average sphericity is preferably 0.82 or more, more preferably 0.85 or more.
• Average sphericity can be measured by the following microscopy method. That is, a particle image taken with an electron microscope or the like is taken into an image analyzer, and the projected area (a) and the circumference of one particle in the taken particle image are measured. The area of a perfect circle having the same perimeter as the measured perimeter is defined as (b), and the sphericity of the particle is determined as a/b.
• the particle size is determined by the above procedure. and its arithmetic mean value is taken as the average sphericity.
• the spherical filler (C) can reduce the surface area compared to an amorphous (non-spherical) alumina filler. Therefore, in the present composition, the contact area between the filler (C) and the resin such as the polyol compound (A) and the polyisocyanate compound (B) can be reduced, thereby suppressing an increase in the viscosity of the present composition. can do. As a result, when the present composition is molded into a sheet or the like, a molded article having a good appearance can be obtained. On the other hand, when an amorphous (non-spherical) alumina filler is used, the viscosity of the composition tends to increase, which may cause cracks in the molded product, resulting in poor appearance.
• the average particle size of the filler (C) is not particularly limited.
• the composition may contain two or more fillers (C) having different average particle sizes.
• the average particle size of the filler (C) is, for example, 3 ⁇ m or more, may be 5 ⁇ m or more, may be 40 ⁇ m or more, may be 50 ⁇ m or more, or may be 60 ⁇ m or more, and It may be 100 ⁇ m or less, 80 ⁇ m or less, 20 ⁇ m or less, or 10 ⁇ m or less.
• the average particle size of the filler (C) having a relatively large average particle size may be, for example, 40 ⁇ m or more, or 50 ⁇ m or more. 60 ⁇ m or more, 100 ⁇ m or less, or 80 ⁇ m or less.
• the average particle size of the filler (C) having a relatively small average particle size is, for example, 3 ⁇ m or more, may be 5 ⁇ m or more, may be 20 ⁇ m or less, or may be 10 ⁇ m or less.
• the average particle size of the filler (C) can be measured by the method described in Examples below.
• the content of the filler (C) in the composition is 400 parts by mass or more with respect to 100 parts by mass of the total amount of the polyol compound (A), the polyisocyanate compound (B), and the plasticizer (D). It may be at least 900 parts by mass, may be at most 750 parts by mass, and is preferably at most 650 parts by mass.
• the cured product obtained using the present composition can have excellent thermal conductivity and excellent electrical insulation.
• the thermal conductivity of the cured product tends to decrease.
• the filler (C) may be surface-treated.
• the surface treatment include a treatment for modifying the surface of spherical alumina particles using a titanate coupling agent; a silane coupling agent; a surfactant; an organic acid such as oleic acid or stearic acid.
• filler (C) for example, those obtained by flame spraying of aluminum hydroxide powder, Bayer method, ammonium alum pyrolysis method, organoaluminum hydrolysis method, aluminum underwater discharge method, freeze-drying method, etc. can be used. can.
• the composition may or may not contain a plasticizer (D), but preferably contains a plasticizer (D).
• the plasticizer (D) contained in the present composition may be one kind or two or more kinds. By including the plasticizer (D) in the present composition, it becomes easier to obtain a cured product with low hardness and excellent flexibility.
• the content of the plasticizer (D) in the present composition is the total amount of the polyol compound (A), the polyisocyanate compound (B), and the plasticizer (D) 100 With respect to parts by mass, it is 30 parts by mass or less, may be 25 parts by mass or less, may be more than 0 parts by mass, may be 10 parts by mass or more, and may be 20 parts by mass or more. There may be.
• the content of the plasticizer (D) contained in the composition increases, the reactivity between the polyol compound (A) and the polyisocyanate compound (B) decreases, and the composition tends to be difficult to cure.
• a known material can be used as the plasticizer (D), but it is preferably an aromatic carboxylic acid ester.
• aromatic carboxylic acid esters include benzoic acid ester plasticizers, phthalic acid plasticizers, and trimellitic acid plasticizers, and benzoic acid ester plasticizers are preferred.
• the composition may contain components other than the polyol compound (A), the polyisocyanate compound (B), the filler (C), and the plasticizer (D).
• Other components include curing accelerators, flame retardants, flame retardant aids, colorants, antioxidants, UV absorbers, heat stabilizers, crystallization accelerators, dispersants, surface conditioners, antifoaming agents, and adhesion. Imparting agents, solvents such as organic solvents, and the like are included.
• the composition may contain one or more other ingredients.
• the present composition is produced by, for example, mixing the polyol compound (A), the filler (C), and other components as necessary to remove water, and then mixing the polyisocyanate compound (B). can do.
• the mixing device for mixing these components is not particularly limited, and kneaders such as mixing rolls, kneaders, Banbury mixers and planetary mixers; vacuum defoaming stirrers and the like can be used. If air bubbles are entrapped during mixing of the above components, mechanical properties such as tensile strength and tear strength of the cured product of the present composition may be lowered, and thermal conductivity may be lowered.
• the mixing device it is preferable to use a planetary mixer or a vacuum stirrer that can suppress the inclusion of air bubbles, and it is more preferable to use a rotation-revolution vacuum stirrer or a planetary mixer under vacuum conditions. preferable.
• Embodiment 2 The cured product of the present embodiment is obtained by curing the present composition described in the first embodiment. Curing of the present composition can be carried out by various methods, for example, a method of thermally polymerizing the present composition by heating, a method of polymerizing the present composition at room temperature, and the like. Since the present composition can be cured at a low temperature, it is possible to reduce environmental load when obtaining a cured product using the present composition.
• the heating temperature is, for example, 70°C or higher and 100°C or lower, or may be 70°C or higher and 90°C or lower.
• the heating time is, for example, 0.05 hours or more and 72 hours or less, and may be 0.1 hours or more and 10 hours or less.
• the room temperature can be 15° C. or higher and 40° C. or lower, and the curing time at room temperature is preferably 12 hours or longer and 72 hours or shorter.
• the curing treatment of the present composition may be performed in an air atmosphere, in a nitrogen atmosphere, in an argon atmosphere, or under vacuum conditions.
• the shape of the cured product is not particularly limited.
• the cured product may be formed into, for example, a film, sheet, plate, cylinder, prism, or the like, and the composition is formed by applying the composition to a desired position. It may have an irregular shape.
• the cured product contains this composition, it has excellent thermal conductivity and excellent heat resistance while improving flexibility. Therefore, the cured product can be used in electronic products and electrical products. and heat-dissipating spacer; can be used for sealing parts of electronic products and electric products.
• the thermally conductive sheet of the present embodiment contains the cured product described in the second embodiment, and may be composed only of the cured product.
• a thermally conductive sheet can be obtained, for example, by forming the present composition described in Embodiment 1 into a sheet and curing the sheet.
• the thermally conductive sheet contains the cured product of this composition, it has excellent flexibility and thermal conductivity, as well as excellent heat resistance.
• the present composition contains a relatively large amount of filler (C) in order to improve thermal conductivity. hydroxyl group) is adjusted to a predetermined range, it is possible to suppress an increase in the hardness of the thermally conductive sheet.
• the Asker C hardness of the thermally conductive sheet is preferably 40 or less, may be less than 40, may be 35 or less, may be 30 or less, or may be 1 or more. It may be 5 or more, or 10 or more.
• a thermally conductive sheet having an Asker C hardness within the above range has good flexibility and a small compressive stress when the thermally conductive sheet is compressed. This makes it easier to bring the thermally conductive sheet into close contact with the member to be attached, thereby reducing thermal resistance.
• the Asker C hardness of the thermally conductive sheet increases, a large compressive stress is required to compress the thermally conductive sheet.
• the Asker C hardness can be measured by the method described in Examples below.
• the thermal conductivity of the thermally conductive sheet is preferably 2.0 W/(mK) or more, may be 2.1 W/(mK) or more, and may be 2.2 W/(mK). ) or more, and usually 6.0 W/(m ⁇ K) or less.
• a thermally conductive sheet having a thermal conductivity within the above range has excellent thermal conductivity, and therefore can exhibit good thermal conductivity when attached to a member to be attached.
• the thermally conductive sheet has an Asker C hardness within the range described above, it is possible to improve the adhesion to the attached member, so when the thermally conductive sheet is attached to the attached member, the heat conduction It is possible to further improve the properties.
• the thermal conductivity can be measured by the method described in Examples below.
• the thickness of the thermally conductive sheet is not particularly limited.
• the thickness of the thermally conductive sheet is preferably 0.1 mm or more, more preferably 0.3 mm or more, and preferably 10 mm or less, more preferably 5 mm or less. When the thickness of the thermally conductive sheet becomes small, the handleability of the thermally conductive sheet may deteriorate.
• Embodiment 4 Method for producing thermally conductive sheet
• the method for producing a thermally conductive sheet according to the present embodiment includes the steps of obtaining a sheet-like molded product obtained by molding the present composition described in Embodiment 1 into a sheet, and curing the sheet-like molded product by heating. ,including.
• a step of cutting out a thermally conductive sheet from the cured sheet-like molding may be included.
• the thermally conductive sheet described in the third embodiment can be suitably manufactured.
• the step of obtaining the sheet-shaped molding can be performed by a method capable of molding the present composition into a sheet, and the method is not particularly limited.
• the method for forming the present composition into a sheet include press molding; roll molding; bar coater molding; extrusion molding; and the like.
• a roll forming method is more preferable from the viewpoint of properties.
• the present composition In the step of obtaining a sheet-like molded product, it is preferable to mold the present composition into a sheet while the surface is protected with release paper or a release film. In the step of obtaining the sheet-like molding, it is preferable to obtain the sheet-like molding having a release paper or a release film laminated on one or both sides thereof.
• the curing step examples include a method of thermally polymerizing the sheet-like molding by heating, a method of polymerizing the present composition at room temperature, and the like.
• the heating temperature can be, for example, 70° C. or higher and 100° C. or lower, preferably 70° C. or higher and 90° C. or lower, and the heating time is, for example, 0.05 hours or longer. It can be 72 hours or more, preferably 0.1 hour or more and 10 hours or less.
• the room temperature can be 15° C. or higher and 40° C. or lower, and the curing time at room temperature is preferably 12 hours or longer and 72 hours or shorter.
• the curing step may be performed in an air atmosphere, in a nitrogen atmosphere, in an argon atmosphere, or under vacuum conditions. Since the present composition can be cured at a low temperature, it is possible to reduce the environmental load when producing a thermally conductive sheet using the present composition.
• the curing temperature is, for example, 60°C or higher and 90°C or lower
• the curing time is, for example, 0.5 hours or longer and 72 hours or shorter.
• the curing step may be performed in an air atmosphere, in a nitrogen atmosphere, in an argon atmosphere, or under vacuum conditions.
• the step of cutting out the thermally conductive sheet is, for example, a method of punching out a hardened or cured sheet-like molding by a press using a punching die; and the like.
• the step of cutting out the thermally conductive sheet may be performed before or after the curing step.
• the kneaded material was taken out from the vacuum dryer, and the kneaded material and the polyisocyanate compound (B) were kneaded using a rotation-revolution vacuum stirrer to obtain a resin composition.
• Tables 1 to 3 Each material shown in Tables 1 to 3 is as follows.
• polyether polyol compound obtained by copolymerizing tetrahydrofuran (THF) having a hydroxyl group and neopentyl glycol (NPG).
• - Polyol compound (cA2) Poly-bd (manufactured by Idemitsu Kosan Co., Ltd.). It is a polybutadiene polyol compound having hydroxyl groups.
• ⁇ Filler (cC2) BX153T manufactured by Nippon Light Metal Co., Ltd.
• the resin composition obtained above was poured into a fluororesin beaker having a volume of 100 mL so that the thickness after curing would be 10 mm, and cured by heating at a temperature of 90° C. to prepare a cured product.
• thermoly conductive sheet After coating the resin composition obtained above on a fluororesin sheet using a bar coater so that the thickness after curing is 2.0 mm, it is cured by heating at a temperature of 90° C. to form a thermally conductive sheet. made.
• the particle size distribution of the filler was measured by particle size distribution measurement using a laser diffraction scattering method, and the particle size at 50% volume accumulation was defined as the average particle size of the filler.
• the cured products obtained using the resin compositions of Examples 1 to 7 had low hardness, excellent flexibility, and excellent thermal conductivity and heat resistance.
• Comparative Example 3 it is considered that the resin composition could not be cured even if the equivalent ratio (isocyanate group/hydroxyl group) was 0.40 because the resin composition did not contain a polycarbonate polyol compound.
• the cured product of the resin composition of Comparative Example 4 had high hardness, poor compressibility and flexibility, and poor thermal conductivity and heat resistance.
• Comparative Example 7 the resin composition increased in viscosity due to the large contact area between the amorphous alumina filler used as the filler and the resin.
• Comparative Example 8 it is believed that the resin composition thickened because the hydroxyl group of aluminum hydroxide reacted with the isocyanate compound (B). Therefore, it is considered that both the thermally conductive sheets obtained using the resin compositions of Comparative Examples 7 and 8 had cracks.
• the cured products of the resin compositions of Comparative Examples 9 and 10 are considered to be inferior in heat resistance because the resin compositions do not contain a polycarbonate polyol compound.

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