WO2013084750A1 - Composition d'agent adhésif autocollant thermoconducteur, moulage en forme de feuille d'adhésif autocollant thermoconducteur, procédés de production correspondants et dispositif électronique - Google Patents

Composition d'agent adhésif autocollant thermoconducteur, moulage en forme de feuille d'adhésif autocollant thermoconducteur, procédés de production correspondants et dispositif électronique Download PDF

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Publication number
WO2013084750A1
WO2013084750A1 PCT/JP2012/080574 JP2012080574W WO2013084750A1 WO 2013084750 A1 WO2013084750 A1 WO 2013084750A1 JP 2012080574 W JP2012080574 W JP 2012080574W WO 2013084750 A1 WO2013084750 A1 WO 2013084750A1
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meth
acid ester
mass
sensitive adhesive
conductive pressure
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PCT/JP2012/080574
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English (en)
Japanese (ja)
Inventor
明子 北川
拓朗 熊本
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日本ゼオン株式会社
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Priority to KR1020147012482A priority Critical patent/KR20140099866A/ko
Priority to CN201280059147.7A priority patent/CN103946331A/zh
Publication of WO2013084750A1 publication Critical patent/WO2013084750A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K7/00—Constructional details common to different types of electric apparatus
    • H05K7/20—Modifications to facilitate cooling, ventilating, or heating
    • H05K7/2039—Modifications to facilitate cooling, ventilating, or heating characterised by the heat transfer by conduction from the heat generating element to a dissipating body
    • H05K7/20436—Inner thermal coupling elements in heat dissipating housings, e.g. protrusions or depressions integrally formed in the housing
    • H05K7/20445—Inner thermal coupling elements in heat dissipating housings, e.g. protrusions or depressions integrally formed in the housing the coupling element being an additional piece, e.g. thermal standoff
    • H05K7/20472—Sheet interfaces
    • H05K7/20481—Sheet interfaces characterised by the material composition exhibiting specific thermal properties
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
    • H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
    • H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
    • H01L23/3737—Organic materials with or without a thermoconductive filler
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • the present invention relates to a heat conductive pressure-sensitive adhesive composition, a heat conductive pressure-sensitive adhesive sheet-like molded article, a production method thereof, and the heat conductive pressure-sensitive adhesive composition or the heat conductive pressure-sensitive adhesive sheet.
  • the present invention relates to an electronic device provided with a shaped molded body.
  • a method of dissipating heat by attaching a heat dissipator such as a metal heat sink, heat dissipating plate, heat dissipating fin or the like to a heat generating element provided in an electronic component or the like is employed. In order to dissipate heat in this way, it is preferable that heat can be efficiently transferred from the heating element to the heat dissipation element.
  • thermo conductive sheet having high thermal conductivity is generally used between the heat generating body and the heat radiating body.
  • a composition hereinafter referred to as “heat conductive pressure sensitive adhesive composition”.
  • the heat conductive pressure-sensitive adhesive composition and the heat conductive pressure-sensitive adhesive sheet-like molded body are used as one of the purposes for transferring heat from the heat generating body to the heat radiating body.
  • the flexibility etc. which can adhere to a body are calculated
  • Examples of the technology related to the heat conductive pressure-sensitive adhesive sheet-like molded article having excellent flexibility include the heat conductive sheet disclosed in Patent Document 1 and the heat conductive pressure-sensitive adhesive sheet disclosed in Patent Document 2. .
  • Alumina and aluminum hydroxide are known as additives that can be added to the resin composition to improve the thermal conductivity of the thermally conductive pressure-sensitive adhesive sheet-like molded body obtained from the resin composition. .
  • these additives are contained in the heat conductive pressure-sensitive adhesive composition or the heat conductive pressure-sensitive adhesive sheet-like molded article, the heat conductive pressure-sensitive adhesive composition or the heat conductive There was a problem that the flexibility of the pressure-adhesive sheet-like molded body was impaired.
  • a plasticizer may be added.
  • a plasticizer only by adding a small amount of plasticizer to the resin composition, it is difficult to obtain the effect of improving the flexibility of the heat conductive pressure-sensitive adhesive sheet-like molded product obtained from the resin composition.
  • the composition thickens and gels, and the cohesive force of the resin composition decreases, making it difficult to mold a heat conductive pressure-sensitive adhesive composition or a heat conductive pressure-sensitive adhesive sheet-like molded body.
  • the present invention provides both a heat conductive pressure-sensitive adhesive composition and a heat conductive pressure-sensitive adhesive sheet-like molded article that have both high thermal conductivity and sufficient flexibility, and the surface portion has sufficient cohesive force, It is an object of the present invention to provide these production methods and an electronic device provided with the heat conductive pressure-sensitive adhesive composition or the heat conductive pressure-sensitive adhesive sheet-like molded body.
  • the first aspect of the present invention is a (meth) acrylic acid ester polymer (A1), a (meth) acrylic acid ester monomer ( ⁇ 1), and a polyfunctional monomer having a plurality of polymerizable unsaturated bonds.
  • D 100 parts by mass of the (meth) acrylic resin composition (A), and 250 parts by mass to 1000 parts by mass of the thermally conductive filler (B1) having a BET specific surface area of 1.0 m 2 / g or more.
  • the dispersant (C) is a fatty acid ester of a polyhydric alcohol polymer.
  • (meth) acryl means “acryl and / or methacryl”.
  • Polymerization reaction of (meth) acrylic acid ester monomer ( ⁇ 1) and polyfunctional monomer (D) refers to (meth) acrylic acid ester monomer ( ⁇ 1) and polyfunctional monomer ( It means one or a plurality of polymerization reactions among a copolymerization reaction with D), a polymerization reaction of (meth) acrylate monomer ( ⁇ 1), and a polymerization reaction of polyfunctional monomer (D). .
  • (Meth) acrylic acid ester polymer (A1) and / or (meth) acrylic acid ester monomer ( ⁇ 1) -derived polymer cross-linking reaction means (meth) acrylic acid ester polymer Cross-linking reaction between (A1), cross-linking reaction between polymers containing structural units derived from (meth) acrylic acid ester monomer ( ⁇ 1), and (meth) acrylic acid ester polymers (A1) and (meth) Among crosslinking reactions with a polymer containing a structural unit derived from an acrylate monomer ( ⁇ 1), it means one or more crosslinking reactions.
  • the “BET specific surface area” means that measured by the following method.
  • a mixed gas of nitrogen and helium is introduced into a BET specific surface area measuring apparatus, and a sample cell containing a sample (an object to be measured for BET specific surface area) is immersed in liquid nitrogen to adsorb nitrogen gas to the sample surface. After reaching adsorption equilibrium, the sample cell is placed in a water bath and warmed to room temperature, and nitrogen adhering to the sample is desorbed. Since the mixing ratio of the gas before and after passing through the sample cell changes during the adsorption and desorption of nitrogen gas, this change is detected by a thermal conductivity detector (TCD) using a gas with a constant mixing ratio of nitrogen and helium as a control. Then, the adsorption amount and desorption amount of nitrogen gas are obtained.
  • TCD thermal conductivity detector
  • thermoly conductive filler is added to improve the thermal conductivity of the thermally conductive pressure-sensitive adhesive composition (F) and the thermally conductive pressure-sensitive adhesive sheet-like molded body (G) described later. Means an additive having a thermal conductivity of 1 W / m ⁇ K or more.
  • the second aspect of the present invention is a (meth) acrylic acid ester polymer (A1), a (meth) acrylic acid ester monomer ( ⁇ 1), and a polyfunctional monomer having a plurality of polymerizable unsaturated bonds.
  • D 100 parts by mass of the (meth) acrylic resin composition (A), and 250 parts by mass to 1000 parts by mass of the thermally conductive filler (B1) having a BET specific surface area of 1.0 m 2 / g or more.
  • the dispersant (C) and the dispersant (C) is a fatty acid ester of a polyhydric alcohol polymer into a sheet shape Or while forming the mixed composition into a sheet, the polymerization reaction of the (meth) acrylic acid ester monomer ( ⁇ 1) and the polyfunctional monomer (D), and the (meth) acrylic acid ester Polymer (A1) and / or said (meta) And cross-linking reaction of acrylic acid ester monomer ([alpha] 1) polymerization comprising a structural unit derived from body, comprising been conducted, it is a heat-conductive and pressure-sensitive adhesive sheet-like molded article (G).
  • the third aspect of the present invention is a (meth) acrylic acid ester polymer (A1), a (meth) acrylic acid ester monomer ( ⁇ 1), and a polyfunctional monomer having a plurality of polymerizable unsaturated bonds.
  • D 100 parts by mass of the (meth) acrylic resin composition (A), and 250 parts by mass to 1000 parts by mass of the thermally conductive filler (B1) having a BET specific surface area of 1.0 m 2 / g or more.
  • the fourth aspect of the present invention is a (meth) acrylic acid ester polymer (A1), a (meth) acrylic acid ester monomer ( ⁇ 1), and a polyfunctional monomer having a plurality of polymerizable unsaturated bonds.
  • D 100 parts by mass of the (meth) acrylic resin composition (A), and 250 parts by mass to 1000 parts by mass of the thermally conductive filler (B1) having a BET specific surface area of 1.0 m 2 / g or more.
  • a thermally conductive pressure-sensitive adhesive sheet-like molded article comprising a step of performing a crosslinking reaction of a polymer containing a structural unit derived from the polymer (A1) and / or the (meth) acrylic acid ester monomer ( ⁇ 1). It is a manufacturing method of (G).
  • a heat radiator and the heat conductive pressure-sensitive adhesive composition (F) of the first aspect of the present invention bonded to the heat radiator, or the heat radiator and the heat radiator. It is the electronic device provided with the heat conductive pressure-sensitive-adhesive sheet-like molded object (G) of the 2nd aspect of this invention combined.
  • thermoly conductive pressure-sensitive adhesive composition and a thermally conductive pressure-sensitive adhesive sheet whose surface portion has sufficient cohesive force.
  • the heat conductive pressure-sensitive adhesive composition (F) of the present invention comprises a plurality of (meth) acrylic acid ester polymer (A1), (meth) acrylic acid ester monomer ( ⁇ 1), and polymerizable unsaturated bonds.
  • thermal conductive filler (B1) BET specific surface area of 1.0 m 2 / g or more
  • thermally conductive filler (B1) BET specific surface area of 1.0 m 2 / g or more
  • thermally conductive filler (B1)) 250 parts by weight or more and 1000 parts by weight or less
  • dispersant (C) by 5 parts by weight or more and 55 parts by weight or less
  • the dispersant (C) is a fatty acid ester of a polyhydric alcohol polymer
  • a polymerization reaction of the (meth) acrylic acid ester monomer ( ⁇ 1) and the polyfunctional monomer (D) The (meth) acrylic acid ester polymer (A ) And and / or the (meth) cross-linking reaction of a polymer containing structural units derived from an acrylic acid ester monomer ([alpha] 1), in which is taking place.
  • the thermally conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention is obtained by molding the (meth) acrylic after the mixed composition is formed into a sheet or while the mixed composition is molded into a sheet. Polymerization reaction of the acid ester monomer ( ⁇ 1) and the polyfunctional monomer (D), the (meth) acrylic acid ester polymer (A1) and / or the (meth) acrylic acid ester monomer ( and a crosslinking reaction of a polymer containing a structural unit derived from ⁇ 1).
  • the substance which comprises a heat conductive pressure sensitive adhesive composition (F) and a heat conductive pressure sensitive adhesive sheet-like molded object (G) is demonstrated below.
  • the (meth) acrylic resin composition (A) used in the present invention comprises a (meth) acrylic acid ester polymer (A1), a (meth) acrylic acid ester monomer ( ⁇ 1), and a plurality of polymerizable unsaturated bonds.
  • the polyfunctional monomer (D) which has.
  • the said (meth) acrylic acid ester monomer ((alpha) 1).
  • a cross-linking reaction of the polymer By carrying out the polymerization and the crosslinking reaction, the polymer containing the structural unit derived from the (meth) acrylate monomer ( ⁇ 1) and the polyfunctional monomer (D) are converted into a (meth) acrylate polymer ( It is mixed and / or partially combined with the component A1).
  • the usage-amount of an acrylic ester polymer (A1) and the (meth) acrylic ester monomer ((alpha) 1) is (meth) with respect to 100 mass% of (meth) acrylic resin compositions (A). It is preferable that they are 5 mass% or more and 49.9 mass% or less of acrylate polymer (A1), and (meth) acrylic acid ester monomer ((alpha) 1) 50 mass% or more and 94.9 mass% or less.
  • the amount of the polyfunctional monomer (D) used is preferably 0.1% by mass or more and 15% by mass or less, with the (meth) acrylic resin composition (A) being 100% by mass, More preferably, it is 0.1 mass% or more and 10 mass% or less, More preferably, it is 0.1 mass% or more and 5 mass% or less.
  • a polyfunctional monomer (D) By making the usage-amount of a polyfunctional monomer (D) into the said range, it is a pressure sensitive adhesive to a heat conductive pressure sensitive adhesive composition (F) and a heat conductive pressure sensitive adhesive sheet-like molded object (G). It becomes easy to achieve both flexibility and tensile strength.
  • the components contained in the (meth) acrylic resin composition (A) will be described in more detail.
  • the (meth) acrylic acid ester polymer (A1) that can be used in the present invention is not particularly limited, but the (meth) acrylic acid ester monomer that forms a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower. It is preferable to contain the unit (a1) and the monomer unit (a2) having an organic acid group.
  • the (meth) acrylic acid ester monomer (a1m) which gives the unit (a1) of the (meth) acrylic acid ester monomer is not particularly limited.
  • ethyl acrylate the glass transition temperature of the homopolymer is -24 ° C
  • n-propyl acrylate (-37 ° C)
  • n-butyl acrylate (-54 ° C)
  • sec-butyl acrylate 22 ° C
  • n-heptyl acrylate - 60 ° C
  • n-octyl acrylate -65 ° C
  • 2-ethylhexyl acrylate -50 ° C
  • 2-methoxyethyl acrylate (-50) ° C)
  • 3-methoxypropyl acrylate (-75 ° C)
  • 3-methoxybutyl acrylate (-56 ° C)
  • n-butyl acrylate, 2-ethylhexyl acrylate, and 2-methoxyethyl acrylate are preferable, n-butyl acrylate and 2-ethylhexyl acrylate are more preferable, and 2-ethylhexyl acrylate is more preferable.
  • acrylic acid ester monomers (a1m) may be used alone or in combination of two or more.
  • the monomer unit (a1) derived therefrom is preferably 80% by mass or more and 99.9% by mass in the (meth) acrylic acid ester polymer (A1). In the following, it is preferable to use it in the polymerization in such an amount that it is 85 mass% or more and 99.5 mass% or less.
  • the amount of the (meth) acrylic acid ester monomer (a1m) is within the above range, the viscosity of the polymerization system at the time of polymerization can be easily maintained within an appropriate range.
  • the monomer (a2m) that gives the monomer unit (a2) having the organic acid group is not particularly limited, but representative examples thereof include organic acid groups such as a carboxyl group, an acid anhydride group, and a sulfonic acid group.
  • monomers containing sulfenic acid groups, sulfinic acid groups, phosphoric acid groups, and the like can also be used.
  • the monomer having a carboxyl group include, for example, ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid, and ⁇ , ⁇ such as itaconic acid, maleic acid, and fumaric acid.
  • ⁇ , ⁇ -ethylenically unsaturated polyvalent carboxylic acid partial esters such as monomethyl itaconate, monobutyl maleate and monopropyl fumarate can be exemplified.
  • the monomer having a sulfonic acid group examples include allyl sulfonic acid, methallyl sulfonic acid, vinyl sulfonic acid, styrene sulfonic acid, ⁇ , ⁇ -unsaturated sulfonic acid such as acrylamide-2-methylpropane sulfonic acid, And salts thereof.
  • the monomer (a2m) among the monomers having an organic acid group exemplified above, a monomer having a carboxyl group is more preferable, and a monomer having acrylic acid or methacrylic acid is particularly preferable. . These monomers are industrially inexpensive and can be easily obtained, have good copolymerizability with other monomer components, and are preferable in terms of productivity. In addition, a monomer (a2m) may be used individually by 1 type, and may use 2 or more types together.
  • the monomer unit (a2) derived therefrom is 0.1% by mass or more and 20% by mass or less in the (meth) acrylic acid ester polymer (A1), preferably It is preferable to use it for the polymerization in such an amount that it is 0.5 to 15% by mass.
  • the usage-amount of the monomer (a2m) which has an organic acid group exists in the said range, it will become easy to maintain the viscosity of the polymerization system at the time of superposition
  • the monomer unit (a2) having an organic acid group is introduced into the (meth) acrylic acid ester polymer (A1) by polymerization of the monomer (a2m) having an organic acid group as described above.
  • an organic acid group may be introduced by a known polymer reaction after the (meth) acrylic acid ester polymer (A1) is produced.
  • the (meth) acrylic acid ester polymer (A1) may contain a monomer unit (a3) derived from a monomer (a3m) having a functional group other than an organic acid group.
  • Examples of the functional group other than the organic acid group include a hydroxyl group, an amino group, an amide group, an epoxy group, and a mercapto group.
  • Examples of the monomer having a hydroxyl group include (meth) acrylic acid hydroxyalkyl esters such as (meth) acrylic acid 2-hydroxyethyl and (meth) acrylic acid 3-hydroxypropyl.
  • Examples of the monomer having an amino group include N, N-dimethylaminomethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, and aminostyrene.
  • Examples of monomers having an amide group include ⁇ , ⁇ -ethylenically unsaturated carboxylic acid amide monomers such as acrylamide, methacrylamide, N-methylol acrylamide, N-methylol methacrylamide, and N, N-dimethylacrylamide. Can be mentioned.
  • Examples of the monomer having an epoxy group include glycidyl (meth) acrylate and allyl glycidyl ether.
  • the monomer (a3m) having a functional group other than the organic acid group one type may be used alone, or two or more types may be used in combination.
  • the monomer unit (a3) derived therefrom is 10% by mass or less in the (meth) acrylate polymer (A1). It is preferable to use it for polymerization in such an amount.
  • the monomer (a3m) of 10% by mass or less it becomes easy to keep the viscosity of the polymerization system during polymerization in an appropriate range.
  • the (meth) acrylic acid ester polymer (A1) has a (meth) acrylic acid ester monomer unit (a1) that forms a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower, and an organic acid group.
  • a monomer derived from the monomer (a4m) copolymerizable with the above-described monomer may be contained.
  • a monomer (a4m) may be used individually by 1 type, and may use 2 or more types together.
  • the amount of the monomer unit (a4) derived from the monomer (a4m) is preferably 10% by mass or less, more preferably 5% by mass or less, based on the acrylate polymer (A1).
  • the monomer (a4m) is not particularly limited, and specific examples thereof include (meth) acrylate monomers other than the (meth) acrylate monomer (a1m), ⁇ , ⁇ -ethylenic monomers. Saturated polycarboxylic acid complete ester, alkenyl aromatic monomer, conjugated diene monomer, non-conjugated diene monomer, vinyl cyanide monomer, carboxylic acid unsaturated alcohol ester, olefin monomer, etc. Can be mentioned.
  • the (meth) acrylate monomer other than the (meth) acrylate monomer (a1m) include methyl acrylate (homopolymer having a glass transition temperature of 10 ° C.), methyl methacrylate. (105 ° C.), ethyl methacrylate (63 ° C.), n-propyl methacrylate (25 ° C.), n-butyl methacrylate (20 ° C.), and the like.
  • ⁇ , ⁇ -ethylenically unsaturated polyvalent carboxylic acid complete ester examples include dimethyl fumarate, diethyl fumarate, dimethyl maleate, diethyl maleate, dimethyl itaconate and the like.
  • alkenyl aromatic monomer examples include styrene, ⁇ -methylstyrene, methyl ⁇ -methylstyrene, vinyl toluene, and divinylbenzene.
  • conjugated diene monomer examples include 1,3-butadiene, 2-methyl-1,3-butadiene (synonymous with isoprene), 1,3-pentadiene, and 2,3-dimethyl-1,3-butadiene. 2-chloro-1,3-butadiene, cyclopentadiene and the like.
  • non-conjugated diene monomer examples include 1,4-hexadiene, dicyclopentadiene, ethylidene norbornene and the like.
  • vinyl cyanide monomer examples include acrylonitrile, methacrylonitrile, ⁇ -chloroacrylonitrile, ⁇ -ethylacrylonitrile and the like.
  • carboxylic acid unsaturated alcohol ester monomer examples include vinyl acetate.
  • olefin monomer examples include ethylene, propylene, butene, pentene and the like.
  • the weight average molecular weight (Mw) of the (meth) acrylic acid ester polymer (A1) is measured by gel permeation chromatography (GPC method) and may be in the range of 1,000 to 1,000,000 in terms of standard polystyrene. Preferably, it is in the range of 100,000 or more and 500,000 or less, more preferably in the range of 200,000 or more and 500,000 or less.
  • the (meth) acrylic acid ester polymer (A1) is a (meth) acrylic acid ester monomer (a1m) that forms a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower, and a monomer having an organic acid group (A2m), a monomer containing a functional group other than an organic acid group (a3m) used as required, and a monomer copolymerizable with these monomers used as needed ( a4m) can be obtained particularly preferably by copolymerization.
  • the polymerization method is not particularly limited, and any of solution polymerization, emulsion polymerization, suspension polymerization, bulk polymerization, and the like may be used.
  • Solution polymerization is preferred, and among them, solution polymerization using a carboxylic acid ester such as ethyl acetate or ethyl lactate or an aromatic solvent such as benzene, toluene or xylene as the polymerization solvent is more preferred.
  • the monomer may be added in portions to the polymerization reaction vessel, but it is preferable to add the whole amount at once.
  • the method for initiating the polymerization is not particularly limited, but it is preferable to use a thermal polymerization initiator as the polymerization initiator.
  • the thermal polymerization initiator is not particularly limited, and may be either a peroxide or an azo compound.
  • Peroxide polymerization initiators include hydroperoxides such as t-butyl hydroperoxide, peroxides such as benzoyl peroxide and cyclohexanone peroxide, and persulfates such as potassium persulfate, sodium persulfate and ammonium persulfate. Can be mentioned. These peroxides can also be used as a redox catalyst in appropriate combination with a reducing agent.
  • the usage-amount of a polymerization initiator is not specifically limited, It is preferable that it is the range of 0.01 to 50 mass parts with respect to 100 mass parts of monomers.
  • polymerization conditions (polymerization temperature, pressure, stirring conditions, etc.) of these monomers are not particularly limited.
  • the obtained polymer is separated from the polymerization medium if necessary.
  • the separation method is not particularly limited.
  • the (meth) acrylic acid ester polymer (A1) can be obtained by placing the polymerization solution under reduced pressure and distilling off the polymerization solvent.
  • the weight average molecular weight of the (meth) acrylic acid ester polymer (A1) can be controlled by appropriately adjusting the amount of the polymerization initiator used in the polymerization and the amount of the chain transfer agent.
  • the (meth) acrylate monomer ( ⁇ 1) is not particularly limited as long as it contains the (meth) acrylate monomer, but forms a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower. It is preferable to contain the (meth) acrylic acid ester monomer (a5m).
  • a (meth) acrylate monomer (a5m) that forms a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower, it is used for the synthesis of a (meth) acrylate polymer (A1) (meth) )
  • a (meth) acrylic acid ester monomer (a5m) may be used individually by 1 type, and may use 2 or more types together.
  • the ratio of the (meth) acrylate monomer (a5m) in the (meth) acrylate monomer ( ⁇ 1) is preferably 50% by mass to 100% by mass, more preferably 75% by mass to 100% by mass. It is as follows. By making the ratio of the (meth) acrylic acid ester monomer (a5m) in the (meth) acrylic acid ester monomer ( ⁇ 1) in the above range, the heat conductive pressure-sensitive adhesive having excellent pressure-sensitive adhesiveness and flexibility. It becomes easy to obtain the agent composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G).
  • the (meth) acrylic acid ester monomer ( ⁇ 1) includes, in addition to the (meth) acrylic acid ester monomer (a5m) forming a homopolymer having a glass transition temperature of ⁇ 20 ° C. or lower. It is good also as a mixture containing the monomer (a6m) which can be copolymerized.
  • Examples of the monomer (a6m) include monomers having an organic acid group similar to those exemplified as the monomer (a2m) used for the synthesis of the (meth) acrylic acid ester polymer (A1). be able to.
  • a monomer (a6m) may be used individually by 1 type, and may use 2 or more types together.
  • the ratio of the monomer (a6m) in the (meth) acrylic acid ester monomer ( ⁇ 1) is preferably 30% by mass or less, and more preferably 10% by mass or less.
  • the (meth) acrylic acid ester monomer ( ⁇ 1) in addition to the (meth) acrylic acid ester monomer (a5m) and the monomer (a6m) having an organic acid group that can be optionally copolymerized, It is good also as a mixture containing the monomer (a7m) copolymerizable with these.
  • the ratio of the monomer (a7m) in the (meth) acrylic acid ester monomer ( ⁇ 1) is preferably 20% by mass or less, and more preferably 15% by mass or less.
  • Examples of the monomer (a7m) include the monomer (a3m) used for the synthesis of the (meth) acrylic acid ester polymer (A1) and the same amount as those exemplified as the monomer (a4m).
  • the body can be mentioned.
  • a monomer (a7m) may be used individually by 1 type, and may use 2 or more types together.
  • Polyfunctional monomer (D) As the polyfunctional monomer (D), one that can be copolymerized with the monomer contained in the (meth) acrylic acid ester monomer ( ⁇ 1) is used.
  • the polyfunctional monomer (D) preferably has a plurality of polymerizable unsaturated bonds, and preferably has the unsaturated bond at the terminal.
  • intramolecular and / or intermolecular crosslinking is introduced into the copolymer, and the heat conductive pressure sensitive adhesive composition (F) and the heat conductive pressure sensitive are introduced.
  • the cohesive force as a pressure-sensitive adhesive of the adhesive sheet-like molded body (G) can be increased.
  • polymerization such as radical thermal polymerization
  • a certain degree of crosslinking reaction proceeds without using a polyfunctional monomer.
  • the polyfunctional monomer (D) is usually used.
  • polyfunctional monomer (D) used in the present invention examples include 1,6-hexanediol di (meth) acrylate, 1,2-ethylene glycol di (meth) acrylate, 1,12-dodecanediol di ( (Meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri ( Polyfunctional (meth) acrylates such as (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and 2 4- bis other substituted triazines, such as
  • monoethylenically unsaturated aromatic ketones such as 4-acryloxy benzophenone can be used.
  • pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate are preferable.
  • a polyfunctional monomer may be used individually by 1 type, and may use 2 or more types together.
  • Examples of the polymerization initiator that can be used in the present invention include a photopolymerization initiator, an azo thermal polymerization initiator, and an organic peroxide thermal polymerization initiator.
  • an organic peroxide thermal polymerization initiator is used. It is preferable to use it.
  • acylphosphine oxide compounds are preferred.
  • Preferred examples of the acylphosphine oxide compound that is a photopolymerization initiator include bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • azo-based thermal polymerization initiator 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2-methylbutyronitrile) ) And the like.
  • organic peroxide thermal polymerization initiator examples include hydroperoxides such as t-butyl hydroperoxide, benzoyl peroxide, cyclohexanone peroxide, 1,6-bis (t-butylperoxycarbonyloxy) hexane, 1,1-bis ( and a peroxide such as t-butylperoxy) -3,3,5-trimethylcyclohexanone.
  • hydroperoxides such as t-butyl hydroperoxide, benzoyl peroxide, cyclohexanone peroxide, 1,6-bis (t-butylperoxycarbonyloxy) hexane, 1,1-bis ( and a peroxide such as t-butylperoxy) -3,3,5-trimethylcyclohexanone.
  • organic peroxide thermal polymerization initiators those having a 1-minute half-life temperature of 100 ° C. or more and 170 ° C. or less are preferable.
  • the amount of the polymerization initiator used is preferably 0.01 parts by mass or more and 10 parts by mass or less, and 0.1 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic resin composition (A). It is more preferable that it is 0.3 mass part or more and 1 mass part or less.
  • the polymerization conversion rate of the (meth) acrylic acid ester monomer ( ⁇ 1) is preferably 95% by mass or more.
  • a heat conductive filler (B1) is used for the heat conductive pressure sensitive adhesive composition (F) and the heat conductive pressure sensitive adhesive sheet-like molded body (G) of the present invention.
  • the heat conductive filler (B1) is an additive that can improve the heat conductivity of the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) when added.
  • the BET specific surface area is 1.0 m 2 / g or more.
  • BET specific surface area of the thermally conductive filler (B1) is preferably at 1.0 m 2 / g or more 10 m 2 / g or less, more preferably at most 1.0 m 2 / g or more 5 m 2 / g, More preferably, it is 1.0 m 2 / g or more and 3 m 2 / g or less.
  • Mixing which is a precursor of the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) by setting the BET specific surface area of the heat conductive filler (B1) within the above range.
  • the thermally conductive filler (B1) having a BET specific surface area in the above predetermined range, when the dispersant (C) described in detail later is used in combination, the surface cohesive force of the mixed composition is maintained and heat is applied. While maintaining the moldability of the conductive pressure-sensitive adhesive composition (F) and the thermally conductive pressure-sensitive adhesive sheet-like molded body (G), the amount of the dispersant (C) added can be increased. This is because the thermal conductive filler (B1) absorbs the dispersant (C) to some extent when the specific surface area of the thermal conductive filler (B1) is not less than the above lower limit, and the dispersant (C) is a mixed composition. This is presumed to prevent it from appearing on the surface.
  • thermally conductive filler (B1) examples include aluminum hydroxide, gallium hydroxide, indium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, and boric acid.
  • examples thereof include zinc hydrate, kaolin clay, calcium aluminate hydrate, calcium carbonate, aluminum carbonate, dawsonite, aluminum oxide, magnesium oxide, zinc oxide, boron nitride, aluminum nitride, and silica.
  • aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium oxide, zinc oxide and aluminum oxide are preferable, aluminum hydroxide and aluminum oxide are more preferable, and aluminum oxide is more preferable.
  • a heat conductive filler (B1) may be used individually by 1 type, and may use 2 or more types together.
  • the amount of the heat conductive filler (B1) used in the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) is (meth) acrylic resin composition (A) 100. It is 250 to 1000 parts by mass, preferably 300 to 800 parts by mass, and more preferably 300 to 600 parts by mass with respect to parts by mass.
  • the mixed composition is a precursor of the heat conductive pressure sensitive adhesive composition (F) and the heat conductive pressure sensitive adhesive sheet-like molded body (G).
  • the viscosity of the product does not increase, preventing the heat conductive pressure sensitive adhesive composition (E) and the heat conductive pressure sensitive adhesive sheet-like molded product (F) from becoming difficult to be molded, and the heat conductive pressure sensitive adhesive composition It suppresses that the hardness of (F) and a heat conductive pressure-sensitive-adhesive sheet-like molded object (G) increases, and shape followability falls. Moreover, a heat conductive pressure sensitive adhesive composition (F) and a heat conductive pressure sensitive adhesive sheet are used by using a heat conductive filler (B1) as content of a heat conductive filler (B1) is more than the said minimum. The effect of improving the thermal conductivity of the shaped molded body (G) is sufficiently obtained.
  • thermoly conductive filler (B2) In addition to the heat conductive filler (B1), the heat conductive pressure sensitive adhesive composition (F) and the heat conductive pressure sensitive adhesive sheet-like molded body (G) of the present invention have a BET specific surface area of 1 described later.
  • Thermally conductive filler (B2) (hereinafter sometimes simply referred to as “thermally conductive filler (B2)”) less than 0.0 m 2 / g may be used in combination.
  • the heat conductive filler (B2) is an additive that can improve the heat conductivity of the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) when added. And the BET specific surface area is less than 1.0 m 2 / g.
  • a heat conductive filler (B2) the same thing can be used except a heat conductive filler (B1) differing in a BET specific surface area.
  • the amount of the heat conductive filler (B2) contained in the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) is (meth) acrylic resin composition (A) 100.
  • the amount is preferably 800 parts by mass or less, and more preferably 600 parts by mass or less with respect to parts by mass.
  • the mixed composition is a precursor of the heat conductive pressure sensitive adhesive composition (F) and the heat conductive pressure sensitive adhesive sheet-like molded body (G).
  • the heat-sensitive pressure-sensitive adhesive composition prevents the heat-sensitive pressure-sensitive adhesive composition (F) and the heat-conductive pressure-sensitive adhesive sheet-like molded body (G) from becoming difficult to be molded without increasing the viscosity of the product. It suppresses that the hardness of (F) and a heat conductive pressure-sensitive-adhesive sheet-like molded object (G) increases, and shape followability falls.
  • a dispersant (C) is used for the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) of the present invention.
  • the mixture composition is added to the mixed composition.
  • a solid additive contained therein for example, the above-mentioned thermally conductive filler (B1), etc., hereinafter may be referred to as “filler” is uniformly dispersed in the mixed composition to improve slippage between the fillers.
  • a heat conductive pressure sensitive adhesive composition (F) and a heat conductive pressure sensitive adhesive sheet-like molded object (G) can be improved.
  • a dispersant (C) it is preferable to use a fatty acid ester of a polyhydric alcohol polymer.
  • the filler is uniformly dispersed and improves the slippage between the fillers, if there is a dispersant, slipping between the fillers tends to occur due to the application of horizontal stress. This means that the arrangement of the fillers is loosened, so that the flexibility and shape following property of the obtained heat conductive pressure-sensitive adhesive sheet-shaped body (G) can be improved.
  • fatty acid ester of the polyhydric alcohol polymer examples include polyglycerin fatty acid ester, polysorbitan fatty acid ester, and polypropylene glycol fatty acid ester. Of these, polyglycerol fatty acid esters are more preferable.
  • polyglycerin fatty acid ester examples include polyglycerin condensed ricinoleic acid ester, polyglycerin ricinoleic acid ester, polyglycerin oleic acid ester, polyglycerin stearic acid ester, and the like. Among them, polyglycerin condensed ricinoleic acid ester is particularly preferable.
  • polysorbitan fatty acid ester include polysorbitan condensed ricinoleic acid ester, polysorbitan ricinoleic acid ester, polysorbitan oleic acid ester, polysorbitan stearic acid ester, and the like.
  • polypropylene glycol fatty acid ester examples include polypropylene glycol condensed ricinoleic acid ester, polypropylene glycol ricinoleic acid ester, polypropylene glycol oleic acid ester, and polypropylene glycol stearic acid ester.
  • ricinoleic acid is a compound having both a carboxyl group and a hydroxyl group
  • a compound obtained by esterification of the carboxyl group possessed by ricinoleic acid and the hydroxyl group possessed by ricinoleic acid, which is a separate molecule is referred to as “condensed ricinolein”.
  • acid a compound obtained by esterification of the carboxyl group possessed by ricinoleic acid and the hydroxyl group possessed by ricinoleic acid, which is a separate molecule
  • the polyglycerin condensed ricinoleic acid ester is obtained by an esterification reaction between a carboxyl group in condensed ricinoleic acid and a hydroxyl group in a compound having a hydroxyl group.
  • the dispersant (C) preferably has a number average molecular weight of 1,000 to 10,000. Moreover, it is preferable that a dispersing agent (C) is a liquid under the temperature of 10 degreeC or more and 40 degrees C or less under 1 atmosphere.
  • the amount of the dispersant (C) used in the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) of the present invention is the (meth) acrylic resin composition (A). 100 parts by mass, 5 parts by mass to 55 parts by mass, preferably 10 parts by mass to 50 parts by mass, and more preferably 15 parts by mass to 45 parts by mass.
  • Mixing composition which is a precursor of heat conductive pressure sensitive adhesive composition (F) and heat conductive pressure sensitive adhesive sheet-like molded object (G) because content of a dispersing agent (C) is below the said upper limit.
  • a dispersant has been used for the purpose of reducing the viscosity of the resin composition by adding it to the resin composition and improving the productivity of a molded product made of the resin composition.
  • a dispersing agent is normally used in the ratio of about 1 mass part with respect to 100 mass parts of resin compositions.
  • the present inventors have used the conventional composition as described above for the heat conductive pressure-sensitive adhesive composition (F) and the mixed composition which is a precursor of the heat conductive pressure-sensitive adhesive sheet-like molded body (G). It has been found that the flexibility of the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) can be improved by adding a larger amount of the dispersant (C) than the amount. It was. When the amount of the dispersant (C) used is increased, the surface cohesive force of the mixed composition is likely to be reduced.
  • the heat conductive filler (B1) and the dispersant (C) in combination even if the amount of the dispersant (C) added is larger than the conventional amount used, the surface cohesive force of the mixed composition can be increased. Can be maintained. That is, according to the present invention, the heat-conductive pressure-sensitive adhesive composition (F) and the heat-conductive pressure-sensitive adhesive composition in which the surface portion has sufficient cohesive strength even when a larger amount of the dispersant (C) is added than the conventional use amount. An adhesive sheet-like molded body (G) can be obtained.
  • thermoelectric pressure-sensitive-adhesive composition (F) and a heat conductive pressure-sensitive-adhesive sheet-like molded object (G) by using a heat conductive filler (B1). Therefore, according to the present invention, it is possible to achieve both high thermal conductivity and sufficient flexibility, and the thermally conductive pressure-sensitive adhesive composition (F) and the thermal conductivity in which the surface portion has sufficient cohesive force.
  • a pressure-sensitive adhesive sheet-like molded product (G) can be obtained.
  • the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention include at least the (meth) acrylic resin composition (A) and the heat conductive filler ( B1) and the dispersing agent (C) may be contained in a predetermined ratio, and a known additive may be further added within a range that does not hinder the above-described effect by using these in combination.
  • additives include phosphoric acid esters; foaming agents (including foaming aids); flame retardant thermally conductive inorganic compounds such as metal hydroxides and metal salt hydrates; glass fibers; expanded graphite powder; Thermally conductive inorganic compounds such as PITCH carbon fibers; external cross-linking agents; pigments such as carbon black and titanium dioxide; other fillers such as clay; nanoparticles such as fullerenes and carbon nanotubes; polyphenols, hydroquinones, hindered amines, etc. Antioxidants; thickeners such as acrylic polymer particles, fine silica, and magnesium oxide; and the like.
  • the thermally conductive pressure-sensitive adhesive composition (F) of the present invention is prepared by mixing the substances described so far to prepare a mixed composition, and then the (meth) acrylic acid ester monomer ( ⁇ 1). And a structural unit derived from the polymerization reaction of the polyfunctional monomer (D) and the (meth) acrylic acid ester polymer (A1) and / or the (meth) acrylic acid ester monomer ( ⁇ 1). It can be obtained by performing at least a crosslinking reaction of the polymer.
  • the method for producing the thermally conductive pressure-sensitive adhesive composition (F) of the present invention comprises (meth) acrylic acid ester polymer (A1), (meth) acrylic acid ester monomer ( ⁇ 1), and polymerizability.
  • a dispersing agent (C) and a step of preparing a mixed composition in which the dispersing agent (C) is a fatty acid ester of a polyhydric alcohol polymer, and in the mixed composition, )
  • Step of performing a crosslinking reaction in the body includes a.
  • the substance which can be used, the preferable content ratio of each substance, the preferable average particle diameter of each substance, and the like are as described above, and the description is omitted.
  • the heat conductive pressure-sensitive-adhesive sheet-like molded object (G) of this invention shape
  • the method for producing the heat conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention comprises (meth) acrylic acid ester polymer (A1), (meth) acrylic acid ester monomer ( ⁇ 1), and A (meth) acrylic resin composition (A) containing a polyfunctional monomer (D) having a plurality of polymerizable unsaturated bonds, and a thermally conductive filler having a BET specific surface area of 1.0 m 2 / g or more ( B1) and a dispersant (C), and a step of producing a mixed composition in which the dispersant (C) is a fatty acid ester of a polyhydric alcohol polymer, and the mixed composition in a sheet form After molding, or while molding the mixed composition into a sheet, the polymerization reaction of the (meth) acrylic acid ester monomer ( ⁇ 1) and the polyfunctional monomer (D) and the (meta) ) Acrylic ester polymer (A1) and / or ( Data) includes the step of performing a
  • heating is preferably performed when the polymerization and the crosslinking reaction are performed.
  • heating for example, hot air, an electric heater, infrared rays, or the like can be used.
  • the heating temperature at this time is preferably a temperature at which the polymerization initiator is efficiently decomposed and the polymerization of the (meth) acrylic acid ester monomer ( ⁇ 1) and the polyfunctional monomer (D) proceeds.
  • the preferred temperature range varies depending on the type of polymerization initiator used, but is preferably 100 ° C. or higher and 200 ° C. or lower, and more preferably 130 ° C. or higher and 180 ° C. or lower.
  • the method for molding the mixed composition into a sheet shape is not particularly limited.
  • a suitable method for example, a method of forming a sheet by applying the above-mentioned mixed composition onto a release film such as a release-treated polyester film, and if necessary, between two release-released films A method of forming a sheet by pressing between the rolls with the mixed composition interposed therebetween, and extruding the mixed composition using an extruder, and controlling the thickness through a die at that time Examples of the method include molding.
  • the thickness of the thermally conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention is preferably 0.05 mm or more and 3 mm or less, and more preferably 0.01 mm or more and 2 mm or less.
  • the heat conductive pressure-sensitive adhesive sheet-shaped molded product (G) is disposed between the heating element and the heat radiating body.
  • the heat resistance in the heat conductive pressure-sensitive adhesive sheet-like molded body (G) does not increase, and heat is easily transferred from the heating element to the heat dissipation element, which is preferable.
  • the heat conductive pressure-sensitive adhesive sheet-shaped molded product (G) is equal to or more than the lower limit, air is applied when the heat conductive pressure-sensitive adhesive sheet-shaped molded product (G) is applied to the heating element or the heat radiating body. As a result, it is difficult to entrain, and as a result, the thermal resistance does not increase and the workability in the step of attaching to the adherend is not inferior.
  • the heat conductive pressure-sensitive adhesive sheet-like molded body (G) can be molded on one side or both sides of the substrate.
  • the material which comprises the said base material is not specifically limited.
  • Specific examples of the substrate include metals having excellent thermal conductivity such as aluminum, copper, stainless steel, and beryllium copper, and polymers having excellent thermal conductivity such as foils of alloys and thermally conductive silicone.
  • Plastic films include polyimide, polyethylene terephthalate, polyethylene naphthalate, polytetrafluoroethylene, polyether ketone, polyethersulfone, polymethylpentene, polyetherimide, polysulfone, polyphenylene sulfide, polyamideimide, polyesterimide, aromatic polyamide, etc.
  • a film made of a heat-resistant polymer can be used.
  • the heat conductive pressure-sensitive-adhesive composition (F) and heat conductive pressure-sensitive-adhesive sheet-like molded object (G) of this invention can be used as some electronic components with which an electronic device is equipped. In that case, it can also be directly molded on a base material such as a radiator and provided as a part of the electronic component.
  • the electronic device and electronic component include electroluminescence (EL), a component around a heat generating part in a device having a light emitting diode (LED) light source, a component around a power device such as an automobile, a fuel cell, a solar cell, and a battery.
  • Devices and parts having heat generating parts such as mobile phones, personal digital assistants (PDAs), notebook computers, liquid crystals, surface conduction electron-emitting device displays (SED), plasma display panels (PDP), or integrated circuits (ICs) Can be mentioned.
  • PDAs personal digital assistants
  • SED surface conduction electron-emitting device displays
  • PDP plasma display panels
  • ICs integrated circuits
  • an LED light source is exemplified below. Examples of usage can be mentioned.
  • LED light source is directly attached to the LED light source; sandwiched between the LED light source and the heat dissipation material (heat sink, fan, Peltier element, heat pipe, graphite sheet, etc.);
  • Examples of LED light source applications include backlight devices for display devices having transmissive liquid crystal panels (TVs, mobile phones, PCs, notebook PCs, PDAs, etc.); vehicle lamps; industrial lighting; commercial lighting; Lighting; and the like.
  • LED light source examples include the following. That is, PDP panel; IC heating part; Cold cathode tube (CCFL); Organic EL light source; Inorganic EL light source; High luminance light emitting LED light source; High luminance light emitting organic EL light source; And so on.
  • examples of the method of using the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention include affixing to the housing of the apparatus.
  • affixing to the housing of the apparatus.
  • a device provided in an automobile or the like it is affixed inside a casing provided in the automobile; affixed outside the casing provided in the automobile; a heat generating part (inside the casing provided in the automobile) Connecting the car navigation / fuel cell / heat exchanger) and the housing; affixing to a heat sink connected to the heat generating part (car navigation / fuel cell / heat exchanger) in the housing of the automobile; Etc.
  • the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded body (G) of the present invention can be used in the same manner.
  • personal computers homes; TVs; mobile phones; vending machines; refrigerators; solar cells; surface-conduction electron-emitting device displays (SEDs); organic EL displays; inorganic EL displays; Organic EL display; laptop computer; PDA; fuel cell; semiconductor device; rice cooker; washing machine; laundry dryer; optical semiconductor device combining optical semiconductor elements and phosphors; Is mentioned.
  • the heat conductive pressure-sensitive adhesive composition (F) and the heat conductive pressure-sensitive adhesive sheet-like molded product (G) of the present invention are not limited to the above-described usage methods, and may be used in other methods depending on the application. Is also possible.
  • used for heat uniformity of carpets and warm mats, etc . used as LED light source / heat source sealant; used as solar cell sealant; used as solar cell backsheet Used between the backsheet of the solar cell and the roof; used inside the heat insulating layer inside the vending machine; used inside the housing of the organic EL lighting with a desiccant or a hygroscopic agent; organic EL lighting Use with desiccant and hygroscopic agent on the heat conductive layer inside the housing of the LED; Use with desiccant and hygroscopic agent on the heat conductive layer and heat dissipation layer inside the housing of the organic EL lighting Used for heat conduction layer inside the housing of organic EL lighting, epoxy heat dissipation layer, and on top of it with desiccant and moisture absorbent; cooling equipment, clothing, towels, sheets, etc.
  • the heat conductive pressure sensitive adhesive composition (F) according to the present invention, the heat conductive pressure sensitive adhesive sheet-like molded product (G), the method for producing the heat conductive pressure sensitive adhesive composition (F), and In the method for producing a heat conductive pressure-sensitive adhesive sheet-like molded body (G),
  • the fatty acid ester of the polyhydric alcohol polymer preferably has a number average molecular weight of 1,000 to 10,000 and is liquid at a temperature of 10 ° C. or more and 40 ° C. or less.
  • the heat conductive pressure-sensitive-adhesive composition (F) which concerns on this invention, the heat conductive pressure-sensitive-adhesive sheet-like molded object (G), the manufacturing method of a heat conductive pressure-sensitive-adhesive composition (F), and heat
  • a preferred fatty acid ester of a polyhydric alcohol polymer is a polyglycerol fatty acid ester.
  • a preferable heat conductive filler (B1) is aluminum oxide having a BET specific surface area of 1.0 m 2 / g or more.
  • the (meth) acrylic resin composition (A) is preferably (meth) acrylic acid ester polymer (A1) 5% by mass or more and 49.9% by mass or less, (meth) acrylic acid ester monomer ( ⁇ 1) 50 It contains from 0.1% by mass to 15% by mass and from 0.1% by mass to 15% by mass of the polyfunctional monomer (D).
  • a heat-conductive pressure-sensitive adhesive sheet-like molded body having a thickness of 1 mm was prepared, and then a test piece was prepared by cutting it into a size of 50 mm width ⁇ 110 mm length. Thereafter, the release PET film was peeled off from one surface of the test piece, and a wrap film was stuck on the surface from which the release PET film was peeled off so as not to enter air. The size of the wrap film may be larger than the adhesive surface of the test piece. And the heat conductivity was measured using the test piece which stuck this wrap film.
  • the thermal conductivity (unit: W / m ⁇ K) was measured by a non-stationary hot wire comparison method using a rapid thermal conductivity meter (trade name “QTM-500”, manufactured by Kyoto Electronics Industry Co., Ltd.).
  • a rapid thermal conductivity meter (trade name “QTM-500”, manufactured by Kyoto Electronics Industry Co., Ltd.).
  • silicone sponge current value: 1A
  • silicone rubber current value: 2A
  • quartz current value: 4A
  • a heat-conductive pressure-sensitive adhesive sheet-like molded body having a thickness of 1 mm was prepared, and a plurality of test pieces were prepared by cutting the sheet into a size of 30 mm width ⁇ 50 mm length.
  • the release PET film was peeled off from these test pieces, and the surface from which the release PET film was peeled was pulverized using talc.
  • Test pieces were laminated so that the thickness was about 6 mm, and placed on a sample table of a hardness meter (trade name “CL-150”, manufactured by Kobunshi Keiki Co., Ltd., JIS K7312). Thereafter, the damper was dropped and the hardness was measured.
  • Example 1 A reactor was charged with 100 parts of a monomer mixture composed of 94% 2-ethylhexyl acrylate and 6% acrylic acid, 0.03 parts 2,2′-azobisisobutyronitrile and 700 parts ethyl acetate. Then, after substitution with nitrogen, a polymerization reaction was carried out at 80 ° C. for 6 hours. The polymerization conversion rate was 97%. The obtained polymer was dried under reduced pressure to evaporate ethyl acetate to obtain a viscous solid (meth) acrylic acid ester polymer (A1-1).
  • the weight average molecular weight (Mw) of the (meth) acrylic acid ester polymer (A1-1) was 270,000, and the weight average molecular weight (Mw) / number average molecular weight (Mn) was 3.1.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) were determined in terms of standard polystyrene by gel permeation chromatography using tetrahydrofuran as an eluent.
  • a thermostatic bath manufactured by Toki Sangyo Co., Ltd., trade name “Biscomate Meat 150III”
  • a Hobart mixer manufactured by Kodaira Manufacturing Co., Ltd., trade name “ACM-5LVT type”, capacity: 5 L
  • the temperature control of the Hobart container was set to 60 ° C.
  • the rotation speed scale was set to 3
  • the mixture was stirred for 10 minutes. This process is referred to as a first mixing process.
  • the mixed composition obtained through the first and second mixing steps is hung on a release PET film having a thickness of 0.1 mm, and another release film having a thickness of 0.1 mm is further formed on the mixed composition. Covered with PET film.
  • This laminate in which the mixed composition was sandwiched between the release PET films was passed through a roll having a distance of 1.2 mm between them to form a sheet. Thereafter, the laminate was put into an oven and heated at 150 ° C. for 15 minutes.
  • Examples 2 to 5 and Comparative Examples 1 to 4 Sheets (G2) to (G5) and (GC1) to (GC4) were obtained in the same manner as in Example 1 except that the composition of each substance was changed as shown in Tables 1 and 2.
  • the sheets (G1) to (G5) according to the examples all had good appearance, and as shown in Table 1, the PET peelability was also excellent. Further, these sheets (G1) to (G5) had high thermal conductivity and excellent flexibility. On the other hand, as shown in Table 2, any of the above performances of the sheets (GC1) to (GC4) according to the comparative examples was inferior. Specifically, it was as follows. -Comparative example 1: The sheet
  • a dispersing agent polyglycerin condensation ricinoleic acid ester
  • Comparative Example 2 The sheet (GC2) of Comparative Example 2 in which the BET specific surface area of the added thermally conductive filler (alumina) is less than the range specified in the present invention is peeled off from the release PET film after the sheet is produced. At that time, material destruction occurred and the shape of the sheet could not be maintained.
  • -Comparative example 3 The sheet
  • Comparative Example 4 The sheet of Comparative Example 4 (GC4) in which the content of the dispersant (polyglycerin condensed ricinoleic acid ester) exceeds the range specified in the present invention (GC4) is peeled off from the release PET film after sheet preparation. Material destruction occurred and the sheet shape could not be maintained.
  • GC4 the sheet of Comparative Example 4 in which the content of the dispersant (polyglycerin condensed ricinoleic acid ester) exceeds the range specified in the present invention

Abstract

L'invention concerne une composition d'agent adhésif autocollant thermoconducteur et un moulage en forme de feuille d'adhésif autocollant thermoconducteur qui combinent une conductivité thermique élevée et une flexibilité suffisante et dont les surfaces présentent une force de cohésion suffisante ; des procédés de production correspondants ; et un dispositif électronique doté de la composition d'agent adhésif autocollant thermoconducteur ou du moulage en forme de feuille d'adhésif autocollant thermoconducteur. La composition d'agent adhésif autocollant thermoconducteur et le moulage en forme de feuille d'adhésif autocollant thermoconducteur sont constitués d'une composition mélangée qui comprend (A) une composition de résine (meth)acrylique, (B1) une charge thermoconductrice ayant une superficie spécifique BET de 1,0 m2/g ou plus, et (C) un agent de dispersion respectivement dans des quantités prescrites, ladite composition de résine (méth)acrylique (A) comprenant (A1) un polymère d'ester (méth)acrylique, (α1) un monomère d'ester (méth)acrylique et (D) un monomère polyfonctionnel ayant de multiples liaisons insaturées polymérisables, et ledit agent de dispersion (C) étant un ester d'acide gras d'un polymère d'alcool polyhydrique, le monomère d'ester (méth)acrylique (α1) et le monomère polyfonctionnel (D) ayant été polymérisés, tandis que le polymère d'ester (méth)acrylique (A1) et/ou un polymère comprenant des unités structurelles dérivées du monomère d'ester (méth)acrylique (α1) ont été réticulés.
PCT/JP2012/080574 2011-12-06 2012-11-27 Composition d'agent adhésif autocollant thermoconducteur, moulage en forme de feuille d'adhésif autocollant thermoconducteur, procédés de production correspondants et dispositif électronique WO2013084750A1 (fr)

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KR1020147012482A KR20140099866A (ko) 2011-12-06 2012-11-27 열전도성 감압 접착제 조성물, 열전도성 감압 접착성 시트상 성형체, 이들의 제조 방법, 및 전자 기기
CN201280059147.7A CN103946331A (zh) 2011-12-06 2012-11-27 导热性压敏粘接剂组合物、导热性压敏粘接性片材状成型体、它们的制造方法、及电子仪器

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JP2013159760A (ja) * 2012-02-08 2013-08-19 Daio Paper Corp 熱伝導性粘着シート
CN103834354A (zh) * 2014-01-25 2014-06-04 深圳市广业电子科技有限公司 一种有机硅压敏胶的制备与应用
WO2015045919A1 (fr) * 2013-09-26 2015-04-02 日本ゼオン株式会社 Composition adhésive sensible à la pression et thermoconductrice, article stratiforme adhésif sensible à la pression et thermoconducteur, leur procédé de production et équipement électronique
WO2015045918A1 (fr) * 2013-09-26 2015-04-02 日本ゼオン株式会社 Composition adhésive autocollante thermoconductrice, article stratiforme adhésif autocollant thermoconducteur, leur procédé de production et matériel électronique
EP3590891A4 (fr) * 2017-03-02 2020-10-14 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Oxyde à base d'alumine thermiquement conducteur et son procédé de production
US11459276B2 (en) 2015-09-16 2022-10-04 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Alumina-based heat conductive oxide and method for producing same

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KR102125306B1 (ko) * 2020-04-07 2020-06-22 이원정 알루미늄 박판을 이용한 재귀반사시트

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JP2002285121A (ja) * 2001-03-27 2002-10-03 Nippon Zeon Co Ltd 感圧接着性組成物およびそれを用いたシート
JP2006233003A (ja) * 2005-02-24 2006-09-07 Nippon Zeon Co Ltd 熱伝導性感圧接着性シート状成形体及びそれを剥離する方法
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JP2013159760A (ja) * 2012-02-08 2013-08-19 Daio Paper Corp 熱伝導性粘着シート
WO2015045919A1 (fr) * 2013-09-26 2015-04-02 日本ゼオン株式会社 Composition adhésive sensible à la pression et thermoconductrice, article stratiforme adhésif sensible à la pression et thermoconducteur, leur procédé de production et équipement électronique
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CN103834354A (zh) * 2014-01-25 2014-06-04 深圳市广业电子科技有限公司 一种有机硅压敏胶的制备与应用
US11459276B2 (en) 2015-09-16 2022-10-04 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Alumina-based heat conductive oxide and method for producing same
EP3590891A4 (fr) * 2017-03-02 2020-10-14 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Oxyde à base d'alumine thermiquement conducteur et son procédé de production

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