WO2008010297A1 - Composition pour résine thermodurcissable conduisant la chaleur et procédé pour la produire - Google Patents

Composition pour résine thermodurcissable conduisant la chaleur et procédé pour la produire Download PDF

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Publication number
WO2008010297A1
WO2008010297A1 PCT/JP2006/314509 JP2006314509W WO2008010297A1 WO 2008010297 A1 WO2008010297 A1 WO 2008010297A1 JP 2006314509 W JP2006314509 W JP 2006314509W WO 2008010297 A1 WO2008010297 A1 WO 2008010297A1
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WO
WIPO (PCT)
Prior art keywords
melting point
thermosetting resin
vol
carbon
resin composition
Prior art date
Application number
PCT/JP2006/314509
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English (en)
Japanese (ja)
Inventor
Tsuneo Kamiyahata
Yoko Kato
Yasuyuki Agari
Kiichi Hasegawa
Original Assignee
Nippon Kagaku Yakin Co., Ltd.
Osaka Municipal Technical Research Institute
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Kagaku Yakin Co., Ltd., Osaka Municipal Technical Research Institute filed Critical Nippon Kagaku Yakin Co., Ltd.
Priority to PCT/JP2006/314509 priority Critical patent/WO2008010297A1/fr
Publication of WO2008010297A1 publication Critical patent/WO2008010297A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity

Definitions

  • thermosetting resin composition and method for producing the same
  • the present invention relates to a heat conductive thermosetting resin composition having high thermal conductivity and excellent molding processability, and a method for producing the same.
  • Patent Document 1 JP-A-5-239321
  • the present invention provides a thermally conductive thermosetting resin composition that solves the above-described problems, has high thermal conductivity, and is excellent in molding processability, and a method for producing the same. Aimed. Means for solving the problem
  • thermosetting resin as a matrix resin and made a low melting point alloy a semi-molten state in which a solid phase part and a liquid phase part are mixed, and the difference in viscosity between the resin and the low melting point alloy.
  • the present invention has been completed by finding that the low melting point alloy is easily dispersed in the resin by making it less susceptible to the influence of the above, and that a high thermal conductivity can be obtained. That is, the thermal conductivity of the present invention
  • the thermosetting resin composition is 10 vol% or more of thermosetting resin, 2 to 80 vol% of heat conductive filler consisting of metal powder and carbon-based filler with a melting point of 500 ° C or more, and a melting point of 300 °. It is characterized by containing 1 to 20 vol% of a low melting point alloy of C or less.
  • the resin composition of the present invention kneads a mixed powder composed of a low melting point alloy, a heat conductive filler and a thermosetting resin while being heated to a temperature at which the low melting point alloy is in a semi-molten state. Can be obtained.
  • the viscosity of the low melting point alloy is made higher than in the case of complete melting so that the difference in viscosity from the thermosetting resin is reduced. Dispersion can be facilitated by curable rosin.
  • thermosetting resin in which the low melting point alloy is more uniformly dispersed in the thermosetting resin can be obtained.
  • the low melting point alloy is in contact with the heat conductive filler, and the heat conductive fillers are welded together to form a three-dimensional heat transfer path.
  • the low melting point alloy uniformly dispersed in the thermosetting resin connects the heat conductive fillers with a smaller volume content than before, and forms a heat transfer path that is evenly distributed in three dimensions. To do.
  • thermosetting resin binds to heat conductive fillers and low melting point alloys by its strong adhesive force, and fixes the formed heat transfer path. As a result, it is possible to provide a resin composition having a high thermal conductivity without lowering the molding processability by setting the volume content of the resin as a matrix to 10 vol% or more.
  • the metal powder iron, copper, nickel, titanium, chromium, and a group force selected from their alloy strength can be used.
  • the resin composition of the present invention as a carbon-based filler, graphite, carbon black, carbon fiber, carbon nanotube, carbon whisker, and a combined force of these are selected.
  • a carbon-based filler graphite, carbon black, carbon fiber, carbon nanotube, carbon whisker, and a combined force of these are selected.
  • One kind can be used.
  • the resin composition of the present invention includes Bi-Sn, Bi-In, In-Zn, In-Ag, In-Na-Na-Sn, Na-Au, Na as low melting point alloys.
  • —Ba ⁇ Na—Li ⁇ Li—Ag, Li—Ca and Li Ba Group power At least one selected can be used.
  • the resin composition of the present invention can be used as a thermally conductive filler containing carbon fiber in an amount of 5 to 15 vol% with respect to the resin composition. Furthermore, carbon fibers having a thermal conductivity of lOOWZm'K or more can be used. [0011]
  • the thermally conductive thermosetting resin composition of the present invention can be produced by the following production method. That is, the method for producing the heat conductive thermosetting resin composition of the present invention comprises a thermosetting resin, a metal powder having a melting point of 500 ° C. or higher, and a heat conductive filler that also has a carbon-based filler.
  • a mixed powder containing a low melting point alloy having a melting point of 300 ° C or lower is heated to a semi-molten state in which the low melting point alloy is mixed with a solid phase portion and a liquid phase portion, and the thermosetting resin is melted and kneaded.
  • the mixture is formed into a desired shape.
  • thermosetting resin 2 to 80 vol% of a heat conductive filler, and a low melting point alloy in the balance
  • a mixed powder containing 10 vol% or more of thermosetting resin, 2 to 80 vol% of a heat conductive filler, and a low melting point alloy in the balance can be used.
  • the resin composition of the present invention has a thermal conductivity of 5 WZm'K or more, which is difficult for conventional heat conductive compositions containing metals, alloys or ceramics, and has excellent moldability. A shape can be obtained.
  • the resin composition of the present invention has a thermosetting resin of 10 vol% or more, a heat conductive filler composed of a metal powder having a melting point of 500 ° C. or more and a carbon-based filler, and a melting point of 300 vol. It contains 1 to 20 vol% of low melting point alloy below ° C.
  • thermosetting resin used in the present invention includes phenol resin, polyimide resin, epoxy resin, isocyanate resin, furan resin, polyurethane resin, aryl resin, key resin resin, and unsaturated resin.
  • Japanese polyester resin, diallyl phthalate resin, melamine resin and the like can be mentioned, and epoxy resin is preferable. It is also preferable that the deflection temperature under load specified in JIS K 7191 is 100 ° C or higher!
  • the epoxy resin is not particularly limited, and a known epoxy resin can be used.
  • examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, tetrabromobisphenol A type epoxy resin, naphthalene type epoxy resin, biphenol type epoxy resin, tetramethylbiphenol type.
  • Polyfunctional epoxy resins such as fats, phenol aralkyl epoxy resins, naphthol aralkyl epoxy resins, naphthol novolac epoxy resins and the like can be used.
  • Curing agents include amine curing agents such as aliphatic amines, aromatic amines, and aliphatic cyclic amines, phenol novolaks, xylene novolacs, biphenol novolacs, bisphenol A novolacs, dicyclopentadiene phenol novolacs, etc.
  • a phenolic curing agent or a catalytic curing agent such as dicyanamide can be used.
  • accelerators such as tertiary amines, imidazoles, and aromatic polyamines can be used.
  • the volume content of the thermosetting resin is 10 vol% or more, preferably 10 to 90 vol%, more preferably 30 to 90 vol%, in order to ensure molding processability.
  • the thermally conductive filler used in the present invention includes a metal powder having a melting point of 500 ° C or higher and a carbon-based filler.
  • a metal powder having a melting point of 500 ° C or higher and a carbon-based filler.
  • metal powder one kind of metal powder selected from the group consisting of iron, copper, nickel, titanium, chromium, and alloys thereof, more preferably iron, copper or nickel, and more preferably copper is used. it can.
  • the shape is not particularly limited, and any shape such as a spherical shape, a teardrop shape, a lump shape, a dendritic shape, and a plate shape can be used, but particularly preferred are dendritic and plate-like copper powders.
  • the particle size of the metal powder is 5 to 150 / ⁇ ⁇ , more preferably 5 to LOO m.
  • carbon-based filler one selected from graphite, carbon black, carbon fiber, carbon nanotube, carbon whisker, and a group force selected from a combination force thereof can be used. More preferred is graphite.
  • copper powder and graphite powder can be used as the heat conductive filler.
  • a method may be used.
  • the copper-graphite composite powder is obtained by coating graphite powder with copper powder via solder or the like, or is a powder obtained by electrolytically or electrolessly plating copper powder on graphite powder, or graphite powder. Any combination of copper and copper powder by mechanical caloring can be used.
  • the particle size of the copper-graphite composite powder is 1-15 O ⁇ m, more preferably 25-: LOO / zm. From particle size force m / J, Saito, or 150 This is because it is larger than ⁇ m and difficult to disperse in the matrix resin.
  • Copper powder has high thermal conductivity among metals, but has a high specific gravity. Therefore, by combining a graphite having a low specific gravity and copper powder, a powder having a low specific gravity and a high thermal conductivity can be obtained. In addition, even if copper is oxidized, graphite is difficult to oxidize, so the amount of decrease in the thermal conductivity of the composite powder can be minimized. In addition, graphite powder with copper powder attached is less susceptible to copper ductility because copper is a plating film. Therefore, there is also an effect of reducing torque generation during molding with less copper deformation during injection molding.
  • the volume content of the heat conductive filler is 2 to 80 vol%, more preferably 10 to 80 vol%, and still more preferably 10 to 70 vol% with respect to the resin composition.
  • the volume content of the metal powder is 1 to 40 vol%, more preferably 1 to 3 Ovol%. If it is less than lvol%, the effect of improving the thermal conductivity is insufficient. If it is more than 40 vol%, the specific gravity of the molded product becomes heavy and the mechanical strength is lowered.
  • the volume content of the carbon-based filler is 1 to 60 vol%, more preferably 1 to 50 vol%.
  • the volume content of copper powder is preferably 1-30 vol%, and the volume content of graphite powder is preferably 1-50 vol%.
  • carbon fiber can be used in addition to the graphite powder.
  • the carbon fiber include those made mainly of cellulose, PAN, and pitch, and those made by vapor phase growth. Since carbon fiber exhibits good thermal conductivity in the fiber direction, it has the effect of connecting metal powders to form a three-dimensional heat conduction path.
  • the carbon fibers are connected to each other through a low melting point alloy to form a three-dimensional heat conduction path, and the effect of improving the heat diffusibility and heat dissipation of the resin composition can be obtained.
  • the thermal conductivity of the carbon fiber in the fiber direction is lOOWZm'K or more, more preferably 700 WZm.K or more.
  • the carbon fiber has a diameter of 1 to 35 ⁇ m, more preferably 5 to 20 ⁇ m, The length is 5 to: LOO ⁇ m, more preferably 20 to 80 ⁇ m. This is because if the diameter of the carbon fiber is smaller than 1 ⁇ m, it will be finely powdered and difficult to handle, and if it is larger than 35 m, it will be easily crushed when kneaded with the resin.
  • the blending ratio of the carbon fiber is 1 to 20 vol%, more preferably 5 to 15 vol%, and further preferably 5 to L0 vol% in the resin composition. If the amount is less than lvol%, the effect of improving the thermal conductivity is not sufficient. If the amount is more than 20 vol%, the moldability of the resin composition decreases.
  • the surface of the thermally conductive filler can be modified with a coupling agent or a sizing agent.
  • a coupling agent such as silane, titanium, or an anorium can be used.
  • the metal powder for example, isopropyl triisostearoyl titanate, acetoalkoxyaluminum diisopropylate and the like can be used.
  • epoxy resin, urethane-modified epoxy resin, polyurethane resin, and polyamide resin can be used as a sizing agent.
  • the heat conductive filler is immersed in a solution in which the coupling agent is dissolved in water or an organic solvent for a predetermined time, or the solution in which the coupling agent is dissolved is sprayed on the heat conductive filler.
  • a solution in which the coupling agent is dissolved in water or an organic solvent for a predetermined time or the solution in which the coupling agent is dissolved is sprayed on the heat conductive filler.
  • the low melting point alloy used in the present invention preferably has a melting point (liquidus temperature) of 300 ° which is preferably a semi-molten state at the melting temperature of the thermosetting resin. Alloys of C or less can be used. Specifically, Bi-Sn, Bi-In, In-Zn, In-Sn, In-Ag, In-Ag, In-Na ⁇ Na-Sn, Na-Au, Na-Ba ⁇ Na-Li ⁇ Li — Ag, Li—Ca ⁇ Li—Ba, and the like. More preferably, at least one alloy selected from the group consisting of Bi—Sn, Bi—In, In—Zn, and In—Sn can be used.
  • Bi—Sn can be used. This is because the selection range of the melting point is wide and the thermal conductivity is high.
  • the particle size of the low melting point alloy is preferably 5 mm or less. If the particle size is larger than 5 mm, it takes time to melt, and furthermore, it is a force that uniformly disperses in the thermosetting resin.
  • the shape is especially Without limitation, any shape such as a spherical shape, a teardrop shape, a lump shape, or a dendritic shape can be used.
  • the volume content of the low melting point alloy is 1 to 20 vol%, more preferably 1 to: LOvol%. If it is less than lv ⁇ 1%, the amount of the low melting point alloy connecting the heat conductive filler is reduced, and the thermal conductivity is lowered. On the other hand, if it is larger than 20 vol%, the amount of the low melting point alloy having a small thermal conductivity increases and the thermal conductivity decreases.
  • the resin composition of the present invention improves the strength and elastic modulus of the molded product, so that the metal fiber made of the above metal, glass fiber, alumina fiber, titanic acid is used. It can contain ceramic fibers such as calcium fibers and nitrided silicon fibers, or calcium carbonate.
  • the resin composition of the present invention is obtained by dry-blending a thermally conductive filler in advance and using a roll, a mixer, a kneader, a kneader, a single-screw kneading extruder, a twin-screw kneading extruder, etc. It can be molded by melting and kneading fat, a heat conductive filler, or the like. In the case of a thermosetting resin for molding materials, it is kneaded, cooled and pulverized, pelletized or tableted, and can be molded into a desired shape by transfer molding, compression molding, injection molding or the like.
  • the kneading temperature is preferably within the range of the kneading temperature of the resin, and is further set to a temperature at which the low melting point alloy is mixed in a solid phase and a liquid phase.
  • a Henschel mixer, a super mixer, a tumbler, or the like can be used.
  • the metal powder having a high density can be dry blended separately from the resin, fed from the middle of extrusion (side feed), and kneaded.
  • the fibrous filler can also be kneaded by side feeding separately from the metal powder.
  • kneading with the low melting point alloy and the filler kneading is performed at a temperature not higher than the curing temperature of the thermosetting resin, preferably not higher than 200 ° C. It is preferable to do.
  • the resin composition of the present invention is excellent in molding processability and has a high thermal conductivity. It can be suitably used for a heat dissipation sheet disposed between a plate or a fan motor. Moreover, it can be used as a conductive adhesive for electric / electronic parts by utilizing its excellent adhesiveness. Furthermore, it can be used for any molded product that requires heat dissipation. For example, parts for household and commercial electrical appliances, for automobiles, heat dissipation measures for cabins, heat dissipation components for heat dissipation measures for inverters between batteries and motors in hybrid vehicles, flooring materials such as flooring for floor heating, etc. It can also be used for a separator in a fuel cell such as a member.
  • it can be used in LED packages for improving heat dissipation of high-power LEDs for electrical and electronic parts. It can also be used in LED module cases that are integrated with a substrate and a heat sink to improve the heat dissipation of LED devices for lighting and backlighting. For example, it can be used as a substrate for mounting semiconductor elements as a heat dissipation measure for semiconductor devices as electrical / electronic components.
  • epoxy resin ortho-cresol novolac type epoxy resin (manufactured by Nippon Yakuhin Co., Ltd., EOCN-103S) (Examples 1 to 4), biphenol type epoxy resin and tetramethylbiphenol type epoxy A mixture of rosin (Japan Epoxy Resin Co., Ltd., YL6121H) (Examples 5 to 8) was used, and the curing agent was a phenolic curing agent (Nippon Yakuyaku Co., Ltd. 83 ° C) was used.
  • Copper powder (Nikko Materials, particle size 20-25 ⁇ m) for metal powder, Graphite (manufactured by Nishimura Graphite, particle size 40-50 ⁇ m), Bi-Sn alloy for low melting point alloy Powder (average particle size 25 ⁇ m) was used.
  • Bi-Sn alloy is (15- 98%) Bi-Sn composition was used.
  • the thermal conductivity was calculated using the laser flash method.
  • the thermal diffusivity was measured according to JIS R 1611 by laser flash method using a thermal constant measuring device (model number TC7000) manufactured by ULVAC-RIKO Co., Ltd., and the specific heat was measured by a heat flux differential scanning heat flow meter (model number DSC manufactured by Shimadzu Corporation).
  • — 50 was measured according to JIS K7123, and the density was measured according to the JIS K7112A method by the underwater substitution method, and these were multiplied to calculate the thermal conductivity.
  • Table 1 shows the results of thermal conductivity measurements.
  • the thickness direction of the sample and the direction of the heat flow at the time of measurement are matched (this is referred to as non-orientation direction, hereinafter referred to as non-orientation) and the length of the sample
  • the direction was measured in accordance with the direction of the heat flow at the time of measurement (this is referred to as the orientation direction, hereinafter referred to as orientation).
  • orientation the orientation direction
  • the filler is generally oriented in the extrusion direction, and thus takes a dispersed state oriented in the length direction of the molded product.
  • the thermally conductive thermosetting resin composition of the present invention is excellent in molding processability and has a high thermal conductivity. Only body members It can also be used for various molded products that require heat dissipation.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine thermodurcissable conduisant la chaleur, ladite résine ayant une conductibilité thermique élevée et une excellente aptitude au moulage, et un procédé permettant de la produire. La composition de résine de l'invention contient : de 2 à 80 % en volume d'une charge conductrice thermique comprenant au moins 10 % en volume d'une résine thermodurcissable ; une poudre métallique ayant un point de fusion au moins égal à 500 °C ; une charge carbonée ; et de 1 à 20 % en volume d'un alliage à bas point de fusion dont le point de fusion ne dépasse pas 300 °C.
PCT/JP2006/314509 2006-07-21 2006-07-21 Composition pour résine thermodurcissable conduisant la chaleur et procédé pour la produire WO2008010297A1 (fr)

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PCT/JP2006/314509 WO2008010297A1 (fr) 2006-07-21 2006-07-21 Composition pour résine thermodurcissable conduisant la chaleur et procédé pour la produire

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PCT/JP2006/314509 WO2008010297A1 (fr) 2006-07-21 2006-07-21 Composition pour résine thermodurcissable conduisant la chaleur et procédé pour la produire

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011236994A (ja) * 2010-05-12 2011-11-24 Bando Chemical Industries Ltd 高負荷伝動用ｖベルト及びその製造方法
CN103687104A (zh) * 2012-09-14 2014-03-26 滕繁 一种新型电热膜发热体的制备方法
CN105283513A (zh) * 2013-06-03 2016-01-27 昭和电工株式会社 微波加热用导电性树脂组合物
JP2018001685A (ja) * 2016-07-06 2018-01-11 ぺんてる株式会社 筆記具

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50748B1 (fr) * 1970-08-03 1975-01-11
JP2001338529A (ja) * 2000-05-30 2001-12-07 Togo Seisakusho Corp 導電性樹脂組成物
JP2002212443A (ja) * 2001-01-23 2002-07-31 Mitsubishi Plastics Ind Ltd 導電性樹脂組成物及び導電性成形品
WO2003029352A1 (fr) * 2001-09-27 2003-04-10 Nippon Kagaku Yakin Co., Ltd. Composition de resine a conductivite thermique elevee et son procede de production

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50748B1 (fr) * 1970-08-03 1975-01-11
JP2001338529A (ja) * 2000-05-30 2001-12-07 Togo Seisakusho Corp 導電性樹脂組成物
JP2002212443A (ja) * 2001-01-23 2002-07-31 Mitsubishi Plastics Ind Ltd 導電性樹脂組成物及び導電性成形品
WO2003029352A1 (fr) * 2001-09-27 2003-04-10 Nippon Kagaku Yakin Co., Ltd. Composition de resine a conductivite thermique elevee et son procede de production

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011236994A (ja) * 2010-05-12 2011-11-24 Bando Chemical Industries Ltd 高負荷伝動用ｖベルト及びその製造方法
CN103687104A (zh) * 2012-09-14 2014-03-26 滕繁 一种新型电热膜发热体的制备方法
CN105283513A (zh) * 2013-06-03 2016-01-27 昭和电工株式会社 微波加热用导电性树脂组合物
JP2018001685A (ja) * 2016-07-06 2018-01-11 ぺんてる株式会社 筆記具

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