WO2021106992A1 - 硬化性組成物セット及び物品 - Google Patents

硬化性組成物セット及び物品 Download PDF

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WO2021106992A1
WO2021106992A1 PCT/JP2020/043978 JP2020043978W WO2021106992A1 WO 2021106992 A1 WO2021106992 A1 WO 2021106992A1 JP 2020043978 W JP2020043978 W JP 2020043978W WO 2021106992 A1 WO2021106992 A1 WO 2021106992A1
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Prior art keywords
curable composition
meth
acrylate
liquid
composition set
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English (en)
French (fr)
Japanese (ja)
Inventor
望 松原
優希 中村
直樹 古川
弘 横田
剛 森本
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Resonac Corp
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Showa Denko Materials Co Ltd
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Priority to CN202080080616.8A priority Critical patent/CN114729091A/zh
Priority to EP20893504.9A priority patent/EP4056611A4/en
Priority to JP2021561479A priority patent/JPWO2021106992A1/ja
Priority to US17/779,130 priority patent/US20230016868A1/en
Priority to KR1020227020268A priority patent/KR20220108081A/ko
Publication of WO2021106992A1 publication Critical patent/WO2021106992A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1063—Esters of polycondensation macromers of alcohol terminated polyethers
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • 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
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K3/02—Elements
    • C08K3/08—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
    • 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
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C08K2003/0812—Aluminium
    • 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
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives
    • 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

Definitions

  • the present invention relates to a curable composition set and an article.
  • a heat conductive material (sometimes called a heat radiating material) called a thermal interface material (TIM) is a material provided between a heat source and a heat radiating member such as a heat sink, and provides thermal resistance between the heat source and the heat radiating member. It reduces and promotes heat conduction from the heat source. Since the heat generated from the heat source is efficiently conducted to the cooling member via the TIM, the heat is easily dissipated from the heat radiating member.
  • Patent Document 1 discloses a thermally conductive grease composition containing a liquid hydrocarbon oil and / or a fluorinated hydrocarbon oil and a predetermined amount of a thermally conductive inorganic filler.
  • Patent Document 2 discloses a thermally conductive grease containing a specific phenyl ether-based base oil, a specific phenol-based antioxidant, and an inorganic powder filler.
  • a pump-out phenomenon may occur in which the grease is pushed out from between the members due to dripping after application or deformation of the member to which the thermally conductive grease is applied.
  • the dripping or pump-out phenomenon causes voids between the grease and the member to reduce the adhesion of the grease to the member and cause an increase in thermal resistance between the thermal grease and the member. Due to the dripping or pump-out phenomenon, other members may be contaminated with grease, resulting in poor insulation.
  • a heat conductive material formed in a solid state such as a sheet may be used.
  • a solid heat conductive material By using a solid heat conductive material, dripping or pump-out phenomenon can be suppressed.
  • an electronic component including a member that generates heat and a member that dissipates heat repeated cooling and heating may cause deformation such as warpage of the member. Therefore, as a solid heat conductive material, a material having low elasticity and excellent elongation is required so as to be able to follow the deformation of the member.
  • An object of the present invention is to provide a curable composition set capable of obtaining a cured product having low elasticity and excellent elongation in one aspect.
  • a cured product of a curable composition set containing a specific compound having a polyoxyalkylene chain and two (meth) acryloyl groups has low elasticity and elongation. Found to be excellent. Further, they have found that this curable composition is suitably used as a heat conductive material because it contains a heat conductive filler, and completed the present invention.
  • the present invention provides the following [1] to [11] in some aspects.
  • a curable composition set comprising a first liquid containing an oxidizing agent and a second liquid containing a reducing agent. At least one of the first liquid and the second liquid contains a compound represented by the following formula (1), and contains.
  • R 11 and R 12 each independently represent a hydrogen atom or a methyl group, and R 13 represents a divalent group having a polyoxyalkylene chain.
  • a curable composition set in which at least one of the first liquid and the second liquid contains a heat conductive filler.
  • a curable composition set capable of obtaining a cured product having low elasticity and excellent elongation.
  • FIG. 5 is a schematic cross-sectional view showing an embodiment of an article comprising a cured product of a curable composition set.
  • FIG. 6 is a schematic cross-sectional view showing another embodiment of an article comprising a cured product of a curable composition set.
  • (meth) acryloyl means “acryloyl” and the corresponding “methacryloyl”, and the same applies to similar expressions such as “(meth) acrylate” and “(meth) acrylic”. ..
  • the weight average molecular weight (Mw) in the present specification means a value determined by using gel permeation chromatography (GPC) under the following conditions and using polystyrene as a standard substance.
  • GPC gel permeation chromatography
  • -Analytical column TSKgel SuperMultipore HZ-H (3 connected) (Product name, manufactured by Tosoh Corporation) -Guard column: TSKguardvolume SuperMP (HZ) -H (product name, manufactured by Tosoh Corporation) -Eluent: THF ⁇ Measurement temperature: 25 ° C
  • the curable composition set includes a first liquid containing an oxidizing agent and a second liquid containing a reducing agent.
  • the oxidizing agent and the reducing agent react to generate free radicals, and the polymerization of the polymerizable component such as the compound represented by the formula (1) described later proceeds.
  • the curable composition set according to the present embodiment by mixing the first liquid and the second liquid, a cured product of a mixture of the first liquid and the second liquid (hereinafter, this cured product is referred to as "curable”.
  • a cured product of the composition set) is obtained.
  • the oxidizing agent contained in the first liquid has a role as a polymerization initiator (radical polymerization initiator).
  • the oxidizing agent may be, for example, an organic peroxide or an azo compound.
  • the organic peroxide may be, for example, hydroperoxide, peroxydicarbonate, peroxyester, peroxyketal, dialkyl peroxide, diacyl peroxide or the like.
  • the azo compound may be AIBN (2,2'-azobisisobutyronitrile), V-65 (azobisdimethylvaleronitrile) or the like.
  • AIBN 2,2'-azobisisobutyronitrile
  • V-65 azobisdimethylvaleronitrile
  • hydroperoxide examples include diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutylhydroperoxide, cumene hydroperoxide and the like.
  • peroxydicarbonate examples include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxymethoxyperoxydicarbonate, and di-2-ethoxymethoxyperoxydicarbonate.
  • Examples thereof include (2-ethylhexylperoxy) dicarbonate, dimethoxybutylperoxydicarbonate, and di (3-methyl-3methoxybutylperoxy) dicarbonate.
  • peroxyester examples include cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, and t.
  • Peroxyketals include 1,1-bis (t-hexylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) cyclohexane, and 1,1-.
  • dialkyl peroxide examples include ⁇ , ⁇ '-bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane, and t-. Butylcumyl peroxide and the like can be mentioned.
  • Diacyl peroxides include isobutyl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, and dichloromethane peroxide. , Benzoyl peroxide, toluene, benzoyl peroxide and the like.
  • the oxidizing agent is preferably a peroxide, more preferably a hydroperoxide, and further preferably 1,1,3,3-tetramethylbutylhydroperoxide or cumene hydroperoxide. , And particularly preferably 1,1,3,3-tetramethylbutylhydroperoxide.
  • the content of the oxidizing agent may be 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more based on the total amount of the first liquid and the second liquid, and is 10% by mass or less. It may be 5% by mass or less, or 3% by mass or less.
  • the reducing agent contained in the second liquid may be, for example, a tertiary amine, a thiourea derivative, a transition metal salt, or the like.
  • a tertiary amine include triethylamine, tripropylamine, tributylamine, N, N-dimethylparatoluidine and the like.
  • the thiourea derivative include 2-mercaptobenzimidazole, methylthiourea, dibutylthiourea, tetramethylthiourea, ethylenethiourea and the like.
  • the transition metal salt include cobalt naphthenate, copper naphthenate, vanadyl acetylacetonate and the like.
  • the reducing agent may be used alone or in combination of two or more.
  • the reducing agent is preferably a thiourea derivative or a transition metal salt from the viewpoint of excellent curing rate.
  • the thiourea derivative may be, for example, ethylene thiourea.
  • the transition metal salt is preferably vanadyl acetylacetonate.
  • the content of the reducing agent may be 0.05% by mass or more, 0.1% by mass or more, or 0.3% by mass or more based on the total amount of the first liquid and the second liquid, and is 5% by mass. Hereinafter, it may be 3% by mass or less, or 1% by mass or less.
  • At least one of the first liquid and the second liquid contains a compound represented by the following formula (1).
  • R 11 and R 12 each independently represent a hydrogen atom or a methyl group
  • R 13 represents a divalent group having a polyoxyalkylene chain.
  • R 11 and R 12 may be a hydrogen atom and the other may be a methyl group, and in another embodiment, both R 11 and R 12 may be hydrogen atoms. In another embodiment, both R 11 and R 12 may be methyl groups.
  • the polyoxyalkylene chain comprises a structural unit represented by the following formula (2).
  • R 13 may be a divalent group having a polyoxyethylene chain, and the compound represented by the formula (1) is preferably a compound represented by the following formula (1-2) (polyethylene glycol di). (Meta) acrylate).
  • (1-2) polyethylene glycol di).
  • R 11 and R 12 have the same meanings as R 11 and R 12 in the formula (1)
  • m is an integer of 2 or more.
  • the polyoxyalkylene chain comprises a structural unit represented by the following formula (3). This makes it possible to facilitate the handling of the curable composition.
  • R 13 may be a divalent group having a polyoxypropylene chain, and the compound represented by the formula (1) is preferably a compound represented by the following formula (1-3) (polypropylene glycol di). (Meta) acrylate).
  • (1-3) polypropylene glycol di).
  • R 11 and R 12 have the same meanings as R 11 and R 12 in the formula (1)
  • n is an integer of 2 or more.
  • the polyoxyalkylene chain is preferably described above from the viewpoint of facilitating both the strength of the cured product of the compound represented by the formula (1) and the handleability of the curable composition. It is a copolymer chain containing a structural unit represented by the formula (2) and a structural unit represented by the formula (3).
  • the copolymer chain may be any of an alternating copolymer chain, a block copolymer chain, and a random copolymer chain.
  • the copolymer chain is preferably a random copolymer chain from the viewpoint of further lowering the crystallinity of the compound represented by the formula (1) and further facilitating the handling of the curable composition.
  • the polyoxyalkylene chain contains an oxytetramethylene group, an oxybutylene group, and an oxypentylene group in addition to the structural unit represented by the formula (2) and the structural unit represented by the formula (3). Or the like, it may have an oxyalkylene group having 4 to 5 carbon atoms as a structural unit.
  • R 13 may be a divalent group having another organic group in addition to the polyoxyalkylene chain described above.
  • Other organic groups may be polyoxyalkylene chain non-chain groups, for example, methylene chain (-CH 2 - chain to the structural units), containing polyester chain (-COO- into the structural unit Chain), polyurethane chain (chain containing —OCON— in the structural unit) and the like.
  • the compound represented by the formula (1) may be a compound represented by the following formula (1-4).
  • R 11 and R 12 have the same meanings respectively as R 11 and R 12 in the formula (1)
  • R 14 and R 15 are each independently an alkylene group having 2 to 5 carbon atoms
  • K1, k2 and k3 are independently integers of 2 or more.
  • k2 may be, for example, an integer of 16 or less.
  • a plurality of R 14 and R 15 may be the same as each other or may be different from each other.
  • the plurality of R 14 and R 15 preferably contain an ethylene group and a propylene group, respectively. That is, the polyoxyalkylene chain represented by (R 14 O) k1 and the polyoxyalkylene chain represented by (R 15 O) k3 are each preferably represented by an oxyethylene group (represented by the above formula (2)). It is a copolymer chain containing an oxypropylene group (a structural unit represented by the above formula (3)).
  • the number of oxyalkylene groups in the polyoxyalkylene chain is preferably 100 or more.
  • the main chain of the compound represented by the formula (1) becomes longer, so that the elongation of the cured product is further excellent and the strength of the cured product is also increased. Can be done.
  • the number of oxyalkylene groups corresponds to m in the formula (1-2), n in the formula (1-3), and k1 and k3 in the formula (1-4), respectively.
  • the number of oxyalkylene groups in the polyoxyalkylene chain is more preferably 130 or more, 180 or more, 200 or more, 220 or more, 250 or more, 270 or more, 300 or more, or 320 or more.
  • the number of oxyalkylene groups in the polyoxyalkylene chain may be 600 or less, 570 or less, or 530 or less.
  • the weight average molecular weight of the compound represented by the formula (1) is preferably 5000 or more, 6000 or more, 7000 or more, 8000 or more, 9000 or more, 10000 or more, 11000 from the viewpoint that the cured product has lower elasticity and excellent elongation. 12000 or more, 13000 or more, 14000 or more, or 15000 or more.
  • the weight average molecular weight of the compound represented by the formula (1) is preferably 100,000 or less, 80,000 or less, 60,000 or less, 34,000 or less, 31,000 or less, or 28,000 or less from the viewpoint of facilitating the adjustment of the viscosity of the curable composition. Is.
  • the compound represented by the formula (1) may be liquid at 25 ° C.
  • the viscosity of the compound represented by the formula (1) at 25 ° C. is preferably 1000 Pa ⁇ s or less from the viewpoint of facilitating coating on the coated surface and improving the adhesion of the cured product to the coated surface. , 800 Pa ⁇ s or less, 600 Pa ⁇ s or less, 500 Pa ⁇ s or less, 350 Pa ⁇ s or less, 300 Pa ⁇ s or less, or 200 Pa ⁇ s or less.
  • 0.1 Pa ⁇ s or more is 0.1 Pa ⁇ s or more, 0.2 Pa ⁇ s or more, 0.3 Pa ⁇ s or more, 1 Pa ⁇ s or more, 2 Pa ⁇ s or more, or 3 Pa ⁇ s or more. It may be s or more.
  • the compound represented by the formula (1) may be in a solid state at 25 ° C.
  • the compound represented by the formula (1) is preferably liquid at 50 ° C. from the viewpoint of further improving the handleability of the curable composition.
  • the viscosity of the compound represented by the formula (1) at 50 ° C. is preferably 100 Pa ⁇ s or less, more preferably 50 Pa ⁇ s or less, from the viewpoint of further improving the handleability of the curable composition. It is more preferably 30 Pa ⁇ s or less, and particularly preferably 20 Pa ⁇ s or less.
  • the viscosity of the compound represented by the formula (1) at 50 ° C. may be 0.1 Pa ⁇ s or more, 0.2 Pa ⁇ s or more, or 0.3 Pa ⁇ s or more.
  • Viscosity means a value measured based on JIS Z 8803, and specifically, a value measured by an E-type viscometer (for example, PE-80L manufactured by Toki Sangyo Co., Ltd.).
  • the calibration of the viscometer can be performed based on JIS Z 8809-JS14000.
  • the viscosity of the compound represented by the formula (1) can be adjusted by adjusting the weight average molecular weight of the compound.
  • the content of the compound represented by the formula (1) is preferably 1% by mass or more, more preferably 1% by mass or more, based on the total amount of the first liquid and the second liquid, from the viewpoint that the cured product has lower elasticity and excellent elongation. Is 1.5% by mass or more, more preferably 2% by mass or more.
  • the content of the compound represented by the formula (1) may be 20% by mass or less, 17% by mass or less, or 15% by mass or less based on the total amount of the first liquid and the second liquid.
  • the curable composition may contain a polymerizable compound (details will be described later) other than the compound represented by the formula (1).
  • the content of the compound represented by the formula (1) is the total of the compound represented by the formula (1) and other polymerizable compounds (hereinafter, from the viewpoint that the cured product has lower elasticity and excellent elongation). It is preferably 10 parts by mass or more, 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more with respect to 100 parts by mass (referred to as "total content of polymerizable components").
  • the content of the compound represented by the formula (1) may be 80 parts by mass or less, 60 parts by mass or less, or 50 parts by mass or less with respect to 100 parts by mass of the total content of the polymerizable component.
  • the curable composition set at least one of the first liquid and the second liquid contains a heat conductive filler.
  • the thermally conductive filler refers to a filler having a thermal conductivity of 10 W / m ⁇ K or more. It is preferable that both the first liquid and the second liquid contain a heat conductive filler.
  • the thermally conductive filler may be insulating or conductive, and is preferably an insulating filler.
  • Materials constituting the insulating heat conductive filler include aluminum oxide, aluminum hydroxide, magnesium oxide, beryllium oxide, boron nitride, aluminum nitride, silicon nitride, silicon carbide, silicon dioxide, aluminum fluoride, and calcium fluoride. Examples include zinc oxide. Examples of the material constituting the conductive heat conductive filler include aluminum, silver, and copper.
  • the shape of the thermally conductive filler may be spherical or polyhedral.
  • the average particle size of the thermally conductive filler is preferably 50 ⁇ m or less, more preferably 40 ⁇ m or less, still more preferably 30 ⁇ m or less, 0.05 ⁇ m or more, 0, from the viewpoint that the cured product of the curable composition set can be arranged thinly. It may be 1 ⁇ m or more, or 0.3 ⁇ m or more.
  • the average particle size of the thermally conductive filler means the particle size (D50) at which the volume cumulative particle size distribution is 50%, and a laser diffraction type particle size distribution measuring device (for example, SALD-2300 (manufactured by Shimadzu Corporation)) is used. Measured using.
  • the content of the heat conductive filler is preferably 60% by mass or more, more preferably 70% by mass, based on the total amount of the first liquid and the second liquid from the viewpoint of enhancing the heat conductivity of the curable composition. % Or more, more preferably 80% by mass or more, and may be 97% by mass or less, 95% by mass or less, or 93% by mass or less.
  • the content of the thermally conductive filler is preferably 70% by volume or more, more preferably 75% by volume or more, based on the total volume of the curable composition, from the viewpoint of enhancing the thermal conductivity of the curable composition. Yes, more preferably 80% by volume or more, 90% by volume or less, 88% by volume or less, or 85% by volume or less.
  • the curable composition may further contain another polymerizable compound that can be copolymerized with the compound represented by the above formula (1) for the purpose of adjusting the physical properties of the curable composition. ..
  • the other polymerizable compound may be, for example, a compound having one (meth) acryloyl group.
  • the compound may be, for example, an alkyl (meth) acrylate.
  • Other polymerizable compounds include, in addition to one (meth) acryloyl group, an aromatic hydrocarbon group, a group containing a polyoxyalkylene chain, a group containing a heterocycle, an alkoxy group, a phenoxy group, a group containing a silane group, and the like. It may be a compound having a group containing a siloxane bond, a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or an epoxy group.
  • the viscosity of the curable composition can be adjusted.
  • the curable composition contains a compound having a hydroxyl group, a carboxyl group, an amino group, or an epoxy group in addition to the (meth) acryloyl group, the curable composition and the member of the cured product are adhered to the curable composition. The sex can be further improved.
  • the alkyl group (alkyl group portion other than the (meth) acryloyl group) in the alkyl (meth) acrylate may be linear, branched or alicyclic.
  • the number of carbon atoms of the alkyl group may be, for example, 1 to 30.
  • the alkyl group may have 1 to 11, 1 to 8, 1 to 6, or 1 to 4, and may have 12 to 30, 12 to 28, 12 to 24, 12 to 22, 12 to 18, or 12 carbon atoms. It may be up to 14.
  • alkyl (meth) acrylate having a linear alkyl group examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, and n-hexyl (n-hexyl).
  • Linear alkyl groups having 1 to 11 carbon atoms such as meta) acrylate, n-heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, or undecyl (meth) acrylate.
  • alkyl (meth) acrylate having a branched alkyl group examples include s-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl (meth) acrylate, isopentyl (meth) acrylate, isoamyl (meth) acrylate, and isooctyl.
  • Alkyl (meth) acrylate having a branched alkyl group having 1 to 11 carbon atoms such as (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, and isodecyl (meth) acrylate, isomyristyl (meth) acrylate.
  • alkyl (meth) acrylates having a branched alkyl group having 12 to 30 carbon atoms such as isostearyl (meth) acrylate and decyltetradecanyl (meth) acrylate.
  • alkyl (meth) acrylate having an alicyclic alkyl group examples include cyclohexyl (meth) acrylate, 3,3,5-trimethylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and terpene (meth). ) Acrylate, dicyclopentanyl (meth) acrylate and the like can be mentioned.
  • Examples of the compound having a (meth) acryloyl group and an aromatic hydrocarbon group include benzyl (meth) acrylate and the like.
  • Examples of the compound having a (meth) acryloyl group and a group containing a polyoxyalkylene chain include polyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, and methoxypolypropylene glycol (meth) acrylate.
  • Examples thereof include polybutylene glycol (meth) acrylate and methoxypolybutylene glycol (meth) acrylate.
  • Examples of the compound having a (meth) acryloyl group and a group containing a heterocycle include tetrahydrofurfuryl (meth) acrylate and the like.
  • Examples of the compound having a (meth) acryloyl group and an alkoxy group include 2-methoxyethyl acrylate.
  • Examples of the compound having a (meth) acryloyl group and a phenoxy group include phenoxyethyl (meth) acrylate and the like.
  • Examples of the compound having a (meth) acryloyl group and a group containing a silane group include 3-acryloyloxypropyltriethoxysilane, 10-methacryloyloxydecyltrimethoxysilane, 10-acryloyloxydecyltrimethoxysilane, and 10-methacryloyloxydecyl. Examples thereof include triethoxysilane, 10-acryloyloxydecyl triethoxysilane, and the like.
  • Examples of the compound having a (meth) acryloyl group and a group containing a siloxane bond include silicone (meth) acrylate and the like.
  • Examples of the compound having a (meth) acryloyl group and a halogen atom include trifluoromethyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, and 1,1,1,3,3,3-hexafluoro.
  • Examples of the compound having a (meth) acryloyl group and a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and the like.
  • Hydroxyalkyl (meth) acrylates such as 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, and 12-hydroxylauryl (meth) acrylate.
  • Acrylate examples thereof include hydroxyalkylcycloalkane (meth) acrylate such as (4-hydroxymethylcyclohexyl) methyl (meth) acrylate.
  • Examples of the compound having a (meth) acryloyl group and a carboxyl group include (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, and monohydroxyethyl phthalate acrylate (for example, manufactured by Toa Synthetic Co., Ltd. Aronix M5400 "), 2-acryloyloxyethyl succinate (for example,” NK ester A-SA “manufactured by Shin-Nakamura Chemical Co., Ltd.) and the like.
  • Examples of the compound having a (meth) acryloyl group and an amino group include N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, and N, N-dimethylaminopropyl (meth) acrylate. , N, N-diethylaminopropyl (meth) acrylate and the like.
  • Examples of the compound having a (meth) acryloyl group and an epoxy group include glycidyl (meth) acrylate, glycidyl ⁇ -ethyl (meth) acrylate, glycidyl ⁇ -n-propyl (meth) acrylate, and ⁇ -n-butyl.
  • the content of the other polymerizable compound is based on the total amount of the first liquid and the second liquid from the viewpoint of making it easier to adjust the viscosity of the curable composition or further improving the adhesion of the curable composition. It may be preferably 1% by mass or more, more preferably 3% by mass or more, further preferably 5% by mass or more, and 20% by mass or less, 15% by mass or less, or 10% by mass or less.
  • the content of the other polymerizable compound is based on 100 parts by mass of the total content of the polymerizable component from the viewpoint of making it easier to adjust the viscosity of the curable composition or further enhancing the adhesion of the curable composition. It may be preferably 30 parts by mass or more, more preferably 40 parts by mass or more, further preferably 50 parts by mass or more, and 90 parts by mass or less, 80 parts by mass or less, or 70 parts by mass or less.
  • the curable composition can further contain a plasticizer.
  • a plasticizer such as butadiene rubber, isoprene rubber, silicon rubber, styrene butadiene rubber, chloroprene rubber, nitrile rubber, butyl rubber, ethylene propylene rubber, urethane rubber, acrylic resin, rosin resin, terpene resin, etc., or poly Examples include alkylene glycol.
  • the content of the plasticizer may be 0.1 part by mass or more, 1 part by mass or more, or 3 parts by mass or more, and 20 parts by mass or less, 15 parts by mass with respect to the total content of the polymerizable component of 100 parts by mass. It may be 10 parts by mass or less, 12 parts by mass or less, or 10 parts by mass or less.
  • the curable composition may further contain an antioxidant from the viewpoint of improving the thermal reliability of the cured product of the curable composition set.
  • the antioxidant may be, for example, a phenol-based antioxidant, a benzophenone-based antioxidant, a benzoate-based antioxidant, a hindered amine-based antioxidant, a benzotriazole-based antioxidant, or the like, and preferably a phenol-based oxidation. It is an inhibitor.
  • the phenolic antioxidant has, for example, a hindered phenol structure (hindered phenol ring).
  • the hindered phenol structure may be, for example, a structure in which a t-butyl group is bonded to one or both of the positions of the ortho position with respect to the hydroxyl group in the phenol ring.
  • the phenolic antioxidant has one or more such hindered phenol rings, preferably two or more, more preferably three or more, and even more preferably four or more.
  • the content of the antioxidant may be 0.1% by mass or more, 0.2% by mass or more, or 0.3% by mass or more based on the total amount of the first liquid and the second liquid, and may be 5% by mass. Below, it may be 4% by mass or less, 3% by mass or less, 2% by mass or less, or 1% by mass or less.
  • the curable composition can further contain other additives, if necessary.
  • Other additives include, for example, surface treatment agents (for example, silane coupling agents), dispersants, curing accelerators, colorants, crystal nucleating agents, heat stabilizers, foaming agents, flame retardants, vibration damping agents, dehydrating agents. , Flame retardant aid (for example, metal oxide) and the like.
  • the content of the other additives may be 0.1% by mass or more and 30% by mass or less based on the total amount of the first liquid and the second liquid.
  • the first liquid and the second liquid may be liquid at 25 ° C.
  • it can be suitably applied to the surface of an object such as a member serving as a heat source or a cooling member, and the adhesion to the applied surface can be improved.
  • each component other than the oxidizing agent and the reducing agent is contained in both the first liquid and the second liquid. That is, in one embodiment, the first liquid contains an oxidizing agent, a compound represented by the formula (1) and a thermally conductive filler (further, other components used as necessary), and the second liquid is reduced. It preferably contains an agent, a compound represented by the formula (1), and a thermally conductive filler (further, other components used as necessary).
  • the cured product of the above-mentioned curable composition set has thermal conductivity, low elasticity, and excellent elongation. Therefore, electronic parts such as power modules, CPUs, and ECUs, batteries, LED lighting, LED backlights, etc. , It is suitably used as a heat conductive material (also called a heat radiating material). That is, one embodiment of the present invention provides a heat conductive material containing the compound represented by the above formula (1) and a heat conductive filler.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of an electronic component comprising a cured product of a curable composition set.
  • the electronic component 1A shown in FIG. 1 includes a semiconductor chip 21 as a heat source and a heat sink 22 as a heat radiating portion.
  • the electronic component 1A includes a cured product 11 of the above-mentioned curable composition set provided between the semiconductor chip 21 and the heat sink 22. Since the cured product 11 has thermal conductivity, the cured product 11 acts as a heat conductive material (thermal interface material) in the electronic component 1A, and heat is conducted from the semiconductor chip 21 to the heat sink 22. Then, heat is dissipated from the heat sink 22 to the outside.
  • a heat conductive material thermal interface material
  • the cured product 11 has low elasticity and excellent elongation by using the above-mentioned curable composition set. Therefore, it has high followability to the deformation of the electronic component 1A caused by heat or the like. Therefore, the heat generated from the semiconductor chip 21 can be effectively conducted to the heat sink 22. Further, since the cured product 11 is a cured product of the above-mentioned curable composition set, it is also excellent in strength (for example, breaking strength).
  • the cured product 11 is obtained by arranging the first liquid and the second liquid between the semiconductor chip 21 and the heat sink 22. Therefore, the generation of voids due to dripping and pump-out phenomenon can be suppressed, and as a result, the adhesion of the cured product 11 (adhesion to the surfaces of the semiconductor chip 21 and the heat sink 22) can be improved. ..
  • the cured product 11 is arranged so as to be in direct contact with the semiconductor chip 21 and the heat sink 22, but the cured product 11 may be in thermal contact with the heat source, and the other one. In the embodiment, it may be arranged so as to be in contact with the heat source (semiconductor chip) via another member.
  • FIG. 2 is a schematic cross-sectional view showing another embodiment of an electronic component comprising a cured product of a curable composition set.
  • the electronic component 1B shown in FIG. 1 is located between a semiconductor chip 21 as a heat source, a heat sink 22 as a heat radiating portion, and the semiconductor chip 21 and the heat sink 22 arranged on one surface of the substrate 23 via an underfill 24.
  • It is a processor including a heat spreader 25 provided.
  • a first cured product 11 provided in contact with the semiconductor chip 21 is provided between the semiconductor chip 21 and the heat spreader 25.
  • a second cured product 11 is provided between the heat spreader 25 and the heat sink 22.
  • the substrate 23, the underfill 24, and the heat spreader 25 may be made of a material generally used in the art.
  • the substrate 23 may be a laminated substrate or the like
  • the underfill 24 may be formed of a resin such as an epoxy resin
  • the heat spreader 25 may be a metal plate or the like.
  • the first cured product 11 and the second cured product 11 are cured products of the above-mentioned curable composition set.
  • the first cured product 11 is in direct contact with the semiconductor chip 21 which is a heat source, but the second cured product 11 is thermally heated to the semiconductor chip 21 which is a heat source via the first cured product 11 and the heat spreader 25. Is in contact with.
  • first cured product 11 and the second cured product 11 have thermal conductivity, they act as thermal conductive materials (thermal interface materials) in the electronic component 1B. That is, the first cured product 11 promotes heat conduction from the semiconductor chip 21 to the heat spreader 25. The second cured product 11 promotes heat conduction from the heat spreader 25 to the heat sink 22. Then, heat is dissipated from the heat sink 22 to the outside.
  • the first cured product 11 and the second cured product 11 also have low elasticity and excellent elongation by using the above-mentioned curable composition set. Therefore, the first cured product 11 and the second cured product 11 have high followability to the deformation of the electronic component 1B caused by heat. Therefore, the heat generated from the semiconductor chip 21 can be more effectively conducted to the heat spreader 25, and the heat can be more effectively conducted to the heat sink 22. Further, since the first cured product 11 and the second cured product 11 are cured products of the above-mentioned curable composition set, they are also excellent in strength (for example, breaking strength).
  • the first cured product 11 and the second cured product 11 are obtained by arranging the first liquid and the second liquid between the semiconductor chip 21 and the heat spreader 25, or between the heat spreader 25 and the heat sink 22. Therefore, even in the electronic component 1B, it is possible to suppress the generation of voids due to the dripping of the curable composition and the pump-out phenomenon, and as a result, the adhesion of the first cured product 11 and the second cured product 11 ( Adhesion to the surface of the semiconductor chip 21, the heat spreader 25 and / or the heat sink 22) can be made excellent.
  • B-1 4-Hydroxybutyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd.)
  • B-2) Isodecyl acrylate (“FA111A” manufactured by Hitachi Kasei Co., Ltd.)
  • oxidizing agent 1 cumene hydroperoxide (containing about 20% aromatic hydrocarbons) (Tokyo Kasei Kogyo Co., Ltd.), or oxidizing agents 2: 1, in the blending amount (parts by mass) shown in Table 1.
  • a first solution was obtained by mixing with 1,3,3-tetramethylbutylhydroperoxide (“Trigonox TMBH-L” manufactured by Kayaku Akzo Corporation).
  • Trigonox TMBH-L 1,3,3-tetramethylbutylhydroperoxide
  • the common component and the reducing agent ethylene thiourea
  • the blending amount of the common component shown in Table 1 is the blending amount in each of the first liquid and the second liquid.
  • the curing time was evaluated using a rheometer (manufactured by Antonio Par).
  • the first liquid and the second liquid were mixed at the mixed mass ratio shown in Table 1 to obtain a mixture (curable composition) of the first liquid and the second liquid.
  • Approximately 1.5 g of the curable composition is weighed on a rheometer disposable sample dish (Anton Par), and the disposable dish and disposable plate D-PP25 (manufactured by Antonio Par) are used so that the thickness of the curable composition is 0.5 mm. ) was adjusted.
  • the disposable plate was vibrated at 1 Hz and a strain of 2%, and the measurement was started with the sample kept at a constant temperature of 25 ° C. The time from the start of measurement until the value of the storage elastic modulus rises was defined as the curing time.
  • the first liquid and the second liquid were mixed at the mixed mass ratio shown in Table 1 to obtain a mixture (curable composition) of the first liquid and the second liquid.
  • the curable composition is filled in a 10 cm ⁇ 10 cm ⁇ 0.2 mm mold (made of SUS plate), covered with a SUS plate, and then heated at 50 ° C. for 30 minutes to be cured.
  • a cured product of a 0.2 mm curable composition set (a cured product of a mixture of the first liquid and the second liquid) was obtained.
  • the obtained cured product was cut into a square of 10 mm ⁇ 10 mm ⁇ 0.2 mm, blackened with a graphite spray, and then subjected to a xenon flash method (NETZSCH-Geratebau GmbH, Selb / explanation “LFA447 nanoflash”) 25.
  • the thermal diffusivity was measured under the condition of ° C. From the product of this value, the density measured by the Archimedes method, and the specific heat of 25 ° C. measured by a differential scanning calorimeter (“DSC250” manufactured by TA Instrument), the thickness of the cured product is based on the following formula. The thermal conductivity in the direction was determined.
  • Table 1 shows the measurement results of each physical property of the cured products of Examples 1 to 9.
  • 1A, 1B electronic components, 11 ... cured product of curable composition set, 21 ... semiconductor chip (heat source), 22 ... heat sink, 23 ... substrate, 24 ... underfill, 25 ... heat spreader.

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