WO2009119513A1 - エポキシ樹脂組成物及び硬化物 - Google Patents
エポキシ樹脂組成物及び硬化物 Download PDFInfo
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- WO2009119513A1 WO2009119513A1 PCT/JP2009/055676 JP2009055676W WO2009119513A1 WO 2009119513 A1 WO2009119513 A1 WO 2009119513A1 JP 2009055676 W JP2009055676 W JP 2009055676W WO 2009119513 A1 WO2009119513 A1 WO 2009119513A1
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- epoxy resin
- resin composition
- epoxy
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- inorganic filler
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Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- 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 is an epoxy resin composition useful for applications such as sealing of electrical and electronic parts, coating materials, laminated materials, composite materials, etc. that give excellent cured products with excellent heat resistance, low thermal expansion, etc.
- the present invention relates to a cured product and a cured product thereof, and is suitably used for printed wiring boards, insulating materials in the electric and electronic fields such as semiconductor sealing, carbon fiber reinforced composite materials, and the like.
- Epoxy resins have been used in a wide range of industrial applications, but their required performance has become increasingly sophisticated in recent years.
- a semiconductor sealing material in a typical field of a resin composition mainly composed of an epoxy resin, but in recent years, as the integration degree of semiconductor elements has improved, the package size has become larger and thinner, and mounting The system is also shifting to surface mounting, and the development of materials with higher solder heat resistance is desired.
- bisphenol A type epoxy resin, bisphenol F type epoxy resin and the like are generally widely known as low viscosity epoxy resins, but they are not sufficient in terms of low viscosity and heat resistance.
- JP-A-4-359909 proposes an epoxy resin having an oxymethylene chain, but it is not sufficient in terms of heat resistance.
- an object of the present invention is to provide an epoxy resin composition that provides a cured product excellent in low viscosity, heat resistance, low thermal expansion, and the like, and a cured product thereof.
- the present invention relates to an epoxy resin composition containing an epoxy resin and an epoxy resin curing agent, and the following general formula (1) (Wherein R is a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, n is 4 and all may be the same or different).
- the present invention relates to an epoxy resin composition having a viscosity of 0.01 to 100 Pa ⁇ s at 25 ° C. when a composition (not including an inorganic filler) is used.
- the abundance ratio (molar ratio) of 1,3-disubstituted and 1,4-disubstituted epoxyethyl groups is in the range of 1: 9 to 9: 1. There should be.
- a polyvalent hydroxy compound is preferable.
- Said epoxy resin composition can contain an inorganic filler, and the content rate of the inorganic filler in that case is good to be 83 weight% or more.
- the present invention also relates to the above-mentioned epoxy resin composition for sealing electric and electronic parts and a cured epoxy resin obtained by curing the above epoxy resin composition.
- the epoxy resin composition of the present invention has an epoxy resin and a curing agent for epoxy resin as essential components, and these essential components as main components of the resin component.
- the epoxy resin composition of the present invention can contain an inorganic filler.
- the above essential components and the inorganic filler are the main components.
- the epoxy resin used in the epoxy resin composition of the present invention is represented by the above general formula (1).
- the epoxy resin of the general formula (1) has a structure in which two epoxyethyl groups are substituted on the benzene skeleton, and the isomers include 1,2-disubstituted, 1,3-disubstituted, There are 1,4-disubstituted.
- the epoxy resin used in the present invention may be a mixture of these isomers, but those having a high content of 1,3-disubstituted products and 1,4-disubstituted products have heat resistance and low viscosity.
- the epoxy resin represented by the general formula (1) is in the range of 1: 9 to 9: 1 in the presence ratio (molar ratio) of the 1,3-di-substituted product and the 1,4-di-substituted product. More preferably, it is in the range of 3: 7 to 7: 3, and still more preferably in the range of 4: 6 to 6: 4.
- the abundance ratio (molar ratio) of 1,3-di-substituted product is higher than this range, heat resistance may not be sufficiently exhibited, and the abundance ratio of 1,4-di-substituted product (molar ratio). Is higher than this range, the crystallinity may be exhibited, and the handling property of the liquid epoxy resin composition is inferior.
- the viscosity of the epoxy resin represented by the general formula (1) at 25 ° C. is 50 mPa ⁇ s or less, more preferably 30 mPa ⁇ s or less. If the viscosity at 25 ° C. is higher than 50 mPa ⁇ s, the viscosity of the epoxy resin composition increases, which is disadvantageous in terms of fluidity during molding and a high filling rate of inorganic fillers, fluidity and low linear expansion. The improvement of performance, such as property, cannot be expected.
- the epoxy resin represented by the general formula (1) having the above characteristics is also referred to as an epoxy resin of the general formula (1).
- the epoxy resin represented by the general formula (1) as described above is obtained by epoxidizing a vinyl group with divinylbenzenes.
- divinylbenzenes can be oxidized with an oxidizing agent such as organic peroxide or hydrogen peroxide to obtain a desired epoxy resin.
- R is H or a hydrocarbon group having 1 to 8 carbon atoms, preferably H, a methyl group or an ethyl group.
- divinylbenzene means a mixture of such isomers of substituted or unsubstituted divinylbenzene.
- the mixing ratio of the isomers of divinylbenzene is preferably substantially the same as the mixing ratio of the isomers of the epoxy resin.
- Examples of the oxidizing agent used in the epoxidation reaction include organic peroxides such as organic peroxides, organic peroxides, hydroperoxides, peroxide esters, and diacyl peroxides, and hydrogen peroxide.
- organic peracid When organic peracid is used as the organic peroxide, formic acid, peracetic acid, perpropionic acid, m-chlorobenzoic acid and the like are exemplified.
- the organic peracetic acid may be used in combination with a catalyst.
- a catalyst for example, an alkali such as sodium carbonate or an acid such as sulfuric acid may be used as a catalyst.
- organic peroxide examples thereof include di-tert-butyl peroxide, bistriphenylmethyl peroxide, and dicumyl peroxide.
- hydroperoxide is used as the organic peroxide
- tert-butyl hydroperoxide cumene hydroperoxide, triphenylmethyl hydroperoxide and the like are exemplified.
- tert-butyl peracetate tert-butyl perpivalate, tert-butyl perisobutyrate, tert-butyl perbenzoate, tert-butyl p-nitrobenzoate, etc. Illustrated.
- diacyl peroxide When diacyl peroxide is used as the organic peroxide, lauroyl peroxide, benzoyl peroxide, acetyl peroxide, propionyl peroxide and the like are exemplified.
- tungstic acid When hydrogen peroxide is used as an oxidizing agent, tungstic acid, molybdic acid, heteropoly acid, etc. are used as catalysts, or some or all of the protons of these acids are converted to organic quaternary ammonium salts, alkali metals, and alkaline earths. It is preferable to use, as a catalyst, a salt or the like substituted with at least one selected from the group consisting of similar metals.
- the charging amount (molar ratio) of the oxidizing agent and divinylbenzenes is not particularly limited, but is, for example, in the range of 0.1 to 20, more preferably 0.1 to 10. It is a range.
- the reaction temperature is not particularly limited and may be a conventional range, but a temperature range in which the epoxidation reaction proceeds preferentially over the decomposition reaction or side reaction of the oxidizing agent is preferable.
- the temperature range is preferably in the range of ⁇ 30 to 200 ° C., more preferably in the range of ⁇ 10 to 100 ° C.
- a solvent can be used as necessary.
- a solvent for example, aromatic solvents such as toluene and xylene, halogen solvents such as chloroform and dichloromethane chlorobenzene, ester solvents such as ethyl acetate and butyl acetate, ketone solvents such as acetone and methyl ethyl ketone, dioxane and the like Or a polar solvent such as acetonitrile, or a mixed solvent of two or more of these.
- the usage-amount of a solvent can be set arbitrarily.
- the epoxy resin thus obtained may contain a small amount of impurities derived from the reaction raw materials and reaction by-products, but these are limited to 20% by weight or less, preferably 10% by weight or less. Is good.
- the epoxy resin may include an oligomer in which the epoxy group in the resin is oligomerized as an ether bond, but when the oligomer component increases, the viscosity is improved, so that the viscosity at 25 ° C. is 50 mPa ⁇ s or less. Must be molecular weight.
- the amount of hydrolyzable chlorine in the epoxy resin used in the present invention is preferably small from the viewpoint of improving the reliability of the electronic component to be sealed. Although it does not specifically limit, 50 ppm or less is preferable, More preferably, it is 10 ppm or less.
- the hydrolyzable chlorine as used in the field of this invention means the value measured by the following method. That is, 0.5 g of a sample was dissolved in 30 ml of dioxane, 10 ml of 1N-KOH was added and the mixture was boiled and refluxed for 30 minutes, cooled to room temperature, and further 100 ml of 80% acetone water was added, and potentiometric titration with 0.002N-AgNO 3 aqueous solution. Is a value obtained by performing
- epoxy resin component used in the present invention in addition to the epoxy resin of the general formula (1), other known and commonly used epoxy resins can be used in combination as long as the effects of the present invention are not impaired.
- examples of other epoxy resins include bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, 2,2′2-biphenol, 3,3 ′, 5,5′-tetramethyl-4,4′-dihydroxybiphenol, resorcin, Epoxidized products of divalent phenols such as naphthalenediols, tris- (4-hydroxyphenyl) methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, phenol novolac, o-cresol novolac, etc.
- curing agent for epoxy resin used in the epoxy resin composition of the present invention all compounds that are commonly used as curing agents for ordinary epoxy resins can be used, aliphatic amines such as diethylenetriamine and triethylenetetramine, Aromatic amines such as metaphenylenediamine, diaminodiphenylmethane, and diaminodiphenylsulfone, polyhydric hydroxy compounds such as phenol novolac resin, orthocresol novolac resin, naphthol novolak resin, phenol aralkyl resin, and modified products thereof, phthalic anhydride, Examples thereof include acid anhydride-based curing agents such as maleic anhydride, hexahydrophthalic anhydride, and pyromellitic anhydride, and latent curing agents such as dicyandiamide, imidazole, BF 3 -amine complexes, and guanidine derivatives.
- polyvalent hydroxy compounds suitable for semiconductor sealing materials are preferably used.
- divalent phenols such as bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, 4,4 ′ -biphenol, 2,2 ′ -biphenol, hydroquinone, resorcin, catechol, naphthalenediols, Trivalent or higher phenols typified by tris- (4-hydroxyphenyl) methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, phenol novolak, o-cresol novolak, naphthol novolak, polyvinylphenol, etc.
- phenols, naphthols, or bisphenol A bisphenol F, bisphenol S, fluorene bisphenol, 4,4 '-biphenol, 2,2' -biphenol, hydroquinone, resorcin, catechol
- Divalent phenols such as naphthalenediol and formaldehyde, acetaldehyde, benzaldehyde, p-hydroxybenzaldehyde, p-xylylene glycol, p-xylylene glycol dimethyl ether, divinylbenzene, diisopropenylbenzene, dimethoxymethylbiphenyls, divinylbiphenyl
- polyvalent hydroxy compounds synthesized by reaction with a crosslinking agent such as diisopropenylbiphenyls.
- the softening point range of the polyvalent hydroxy compound is preferably 40 to 150 ° C, more preferably 50 to 120 ° C.
- the temperature is lower than 40 ° C., for example, when the epoxy resin composition is filled with an inorganic material, there is a problem that the viscosity becomes too low and the inorganic material settles.
- the temperature is higher than 150 ° C., kneadability at the time of preparing the epoxy resin composition There is a problem in formability.
- the melt viscosity at 150 ° C. is preferably 1 Pa ⁇ s or less, more preferably 0.5 Pa ⁇ s or less.
- an epoxy resin composition means a composition comprising all epoxy resins and all curing agents blended in the epoxy resin composition.
- the epoxy resin composition of the present invention preferably has a low viscosity in order to mix the inorganic filler with a high content. Therefore, the viscosity of the epoxy resin composition in a state where the inorganic filler is removed from the epoxy resin composition is 0.01 to 100 Pa ⁇ s, preferably 1 to 100 Pa ⁇ s at 25 ° C.
- An inorganic filler can be blended in the epoxy resin composition of the present invention.
- An epoxy resin composition containing an inorganic filler is suitable for sealing.
- the inorganic filler include silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, mullite, titania, and one of these or Two or more kinds may be combined, but it is preferable to use fused silica as a main component, and examples of the form include crushed or spherical forms. Usually, silica is used in combination with those having several kinds of particle size distributions.
- the average particle diameter of the silica to be combined is preferably 0.5 to 100 ⁇ m.
- the content is preferably 83% by weight or more, more preferably 83 to 90% by weight. If it is less than 83% by weight, the organic component content will be high, and the moisture resistance and low linear expansion will not be sufficiently exhibited.
- an oligomer or a polymer compound such as polyester, polyamide, polyimide, polyether, polyurethane, petroleum resin, indene coumarone resin, or phenoxy resin is appropriately blended as necessary.
- additives such as pigments, refractory agents, thixotropic agents, coupling agents, fluidity improvers and the like can be blended.
- the pigment include organic or inorganic extender pigments and scaly pigments.
- the thixotropic agent include silicon-based, castor oil-based, aliphatic amide wax, oxidized polyethylene wax, and organic bentonite-based.
- curing accelerators such as amines, imidazoles, organic phosphines, and Lewis acids can be blended.
- the blending amount of the curing accelerator is preferably 0.2 to 5 parts by weight with respect to 100 parts by weight of the epoxy resin.
- the resin composition of the present invention includes a release agent such as carnauba wax and OP wax, a coupling agent such as ⁇ -glycidoxypropyltrimethoxysilane, a colorant such as carbon black, and trioxide.
- a flame retardant such as antimony, a low stress agent such as silicone oil, a lubricant such as calcium stearate, and the like can be blended.
- the cured product of the present invention can be obtained by curing the epoxy resin composition by a molding method such as casting, compression molding, transfer molding or the like.
- the temperature at which the cured product is produced is usually 120 to 220 ° C.
- 1640 g of a 30% peracetic acid ethyl acetate solution was added dropwise over 3 hours. During the dropping, the reaction temperature was controlled to 30 ° C. After dropping, the mixture was further stirred at 30 ° C. for
- Synthesis example 2 In a four-necked separable flask, 65 g of hydroquinone, 546 g of epichlorohydrin, and 82 g of diethylene glycol dimethyl ether were added and dissolved by stirring. After uniformly dissolving, maintaining at 65 ° C. under a reduced pressure of 130 mmHg, 98.4 g of 48% aqueous sodium hydroxide solution was added dropwise over 4 hours, and water and epichlorohydrin refluxed during this addition were separated in a separation tank, and epichlorohydrin was The mixture was returned to the reaction vessel, and water was removed from the system to react.
- Example 1 and Comparative Examples 1 and 2 An epoxy resin composition was prepared by kneading at the blending ratio shown in Table 1 using the epoxy resin, curing agent and inorganic filler shown below and triphenylphosphine as a curing accelerator.
- the epoxy resin a obtained in the above synthesis example 1 the hydroquinone type epoxy resin b obtained in the above synthesis example 2 for comparison, and an epoxy resin c (bisphenol F type epoxy resin, manufactured by Tohto Kasei Co., Ltd.) YDF-170; epoxy equivalent of 167 g / eq., Viscosity at 25 ° C. is 2.9 Pa ⁇ s).
- an epoxy resin c bisphenol F type epoxy resin, manufactured by Tohto Kasei Co., Ltd.
- PN phenol novolak resin, manufactured by Gunei Chemical Co., Ltd., PSM-4261; OH equivalent 103, softening point 82 ° C.
- spherical fused silica FB-60 (average particle size 21 ⁇ m) and FB-35 (average particle size 12 ⁇ m) manufactured by Denki Kagaku Kogyo Co., Ltd.
- spherical fused silica SO-C3 (average particle size) manufactured by Admatex Co., Ltd.
- a mixture of four types, 0.9 ⁇ m diameter) and SO—C2 (average particle diameter 0.5 ⁇ m) was used.
- the spiral flow and gel time were measured about the epoxy resin composition obtained by mixing a filler with the said epoxy resin composition.
- an epoxy resin composition is molded using a spiral flow measurement mold in accordance with the standard (EMMI-1-66) under conditions of spiral flow injection pressure (150 kgf / cm 2 ) and curing time of 3 minutes. The flow length was examined.
- gel time the epoxy resin composition is poured into a concave portion of a gelation tester (Nisshin Kagaku Co., Ltd.) that has been heated to 175 ° C. in advance and is rotated twice per second using a Teflon rod. The gelation time required for the epoxy resin composition to cure was examined.
- the epoxy resin composition was molded at 175 ° C. and post-cured at 175 ° C. for 12 hours to obtain a cured product test piece, which was then subjected to various physical property measurements.
- the glass transition point was calculated
- the bending test was performed by a three-point bending method for bending strength and bending elastic modulus.
- the water absorption is the value obtained when a disk having a diameter of 50 mm and a thickness of 3 mm is molded using the epoxy resin composition and moisture-absorbed for 100 hours under conditions of 85 ° C. and 85% RH after post-curing.
- Table 1 The results are summarized in Table 1.
- the epoxy resin composition of the present invention is excellent in low viscosity, and can give a cured product excellent in heat resistance and low thermal expansion.
- the epoxy resin composition of the present invention exhibits excellent fluidity during molding by using an epoxy resin excellent in low viscosity. Moreover, the filler filling rate can be increased due to the low viscosity.
- the epoxy resin component does not have a flexible oxymethylene moiety compared to the glycidyl ether group that general epoxy resins have, excellent heat resistance and low thermal expansion are achieved by suppressing the molecular motion of the cured product. Sex is demonstrated. Due to the above excellent fluidity, heat resistance, and low thermal expansibility, it can be suitably used for semiconductor encapsulating materials, various molding materials, laminated materials, powder coating materials, adhesive materials and the like. In particular, it is excellent for electronic component sealing.
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Abstract
Description
(ここで、Rは水素原子又は炭素数1~8の炭化水素基であり、nは4であり、全てが同一でも異なっていてもよい。)で表わされ、2個のエポキシエチル基の置換位置が1,3-ジ置換体及び1,4-ジ置換体であるエポキシ化合物を合計で90重量%以上含有し、25℃での粘度が50mPa・s以下であるエポキシ樹脂を使用し、組成物(無機充填材を含まない)としたときの粘度が25℃で0.01~100Pa・sであることを特徴とするエポキシ樹脂組成物に関する。
本発明のエポキシ樹脂組成物は、エポキシ樹脂、及びエポキシ樹脂用硬化剤を必須成分とし、且つこれら必須成分を樹脂成分の主成分とする。本発明のエポキシ樹脂組成物は無機充填材を含むことができ、この場合は、上記必須成分と無機充填材を主成分とする。
3L反応器にジビニルベンゼン(新日鐵化学製DVB-960ジビニルベンゼン含有量97%、m-体/p-体=62:38)300g、酢酸エチル1200gを装入し撹拌した。次いで、過酢酸30%酢酸エチル溶液1640gを3時間かけて滴下した。滴下中は反応温度を30℃になるように制御を行った。滴下後、さらに30℃にて3時間撹拌を行った。反応液を室温まで冷却した後、20%NaOH水溶液1208gを加え、1時間撹拌後、水層を分離し、未反応の過酢酸及び、生成した酢酸の除去を行った。エバポレーターにて、酢酸エチルを減圧留去した後、ジエポキシエチルベンゼン151.6gを得た(エポキシ樹脂a)。得られた樹脂のエポキシ当量は111g/eq.25℃における粘度は10mPa・s、純度は94.3%(ガスクロマトグラフィー面積%)、m-体/P-体=64:36(1H-NMR積分比)であった。
四つ口セパラブルフラスコにハイドロキノン65g、エピクロルヒドリン546g、ジエチレングリコールジメチルエーテル82gを入れ撹拌溶解させた。均一に溶解後、130mmHgの減圧下65℃に保ち、48%水酸化ナトリウム水溶液98.4gを4時間かけて滴下し、この滴下中に還流留出した水とエピクロルヒドリンを分離槽で分離しエピクロルヒドリンは反応容器に戻し、水は系外に除いて反応した。反応終了後、濾過により生成した塩を除き、更に水洗したのちエピクロルヒドリンを留去し、エポキシ樹脂120gを得た(エポキシ樹脂b)。得られた樹脂のエポキシ当量は116g/eq.、融点は100℃であった。
下記に示すエポキシ樹脂、硬化剤、無機充填材と、硬化促進剤としてトリフェニルホスフィンを用い、表1に示す配合割合で混練してエポキシ樹脂組成物を調製した。
Claims (6)
- 一般式(1)で表わされるエポキシ樹脂の1,3-ジ置換体と1,4-ジ置換体の存在割合(モル比)が1:9~9:1の範囲である請求項1に記載のエポキシ樹脂組成物。
- エポキシ樹脂用硬化剤が多価ヒドロキシ化合物である請求項1に記載のエポキシ樹脂組成物。
- 無機充填材を83重量%以上含有する請求項1に記載のエポキシ樹脂組成物。
- 電気・電子部品封止用であることを特徴とする請求項1に記載のエポキシ樹脂組成物。
- 請求項1~5のいずれかに記載のエポキシ樹脂組成物を硬化してなることを特徴とするエポキシ樹脂硬化物。
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JP2010505634A JP5450386B2 (ja) | 2008-03-27 | 2009-03-23 | エポキシ樹脂組成物及び硬化物 |
KR1020107022765A KR101522346B1 (ko) | 2008-03-27 | 2009-03-23 | 에폭시수지 조성물 및 경화물 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2010101144A1 (ja) * | 2009-03-05 | 2010-09-10 | 新日鐵化学株式会社 | エポキシ樹脂組成物 |
WO2011071745A1 (en) * | 2009-12-09 | 2011-06-16 | Dow Global Technologies Llc | Epoxy resin compositions |
WO2011103014A1 (en) | 2010-02-19 | 2011-08-25 | Dow Global Technologies Llc | Divinylarene dioxide resin compositions |
JP2011176278A (ja) * | 2009-11-23 | 2011-09-08 | Dow Global Technologies Llc | アンダーフィル用途のためのエポキシ樹脂配合物 |
WO2011119655A3 (en) * | 2010-03-24 | 2011-12-15 | Dow Global Technologies Llc | Process for preparing divinlylarene dioxides |
JP2012092247A (ja) * | 2010-10-28 | 2012-05-17 | Showa Denko Kk | 液状硬化性組成物 |
JP2012124238A (ja) * | 2010-12-07 | 2012-06-28 | Namics Corp | 電子部品実装体、および電子部品の実装方法 |
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JP2012092247A (ja) * | 2010-10-28 | 2012-05-17 | Showa Denko Kk | 液状硬化性組成物 |
JP2013543046A (ja) * | 2010-11-22 | 2013-11-28 | ダウ グローバル テクノロジーズ エルエルシー | 強靱化剤としてdvbdoの付加物を含むエポキシ樹脂 |
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US11267773B2 (en) | 2019-09-10 | 2022-03-08 | Countertrace, LLC | Hexasubstituted benzenes, surfaces modified therewith, and associated methods |
Also Published As
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KR20110008034A (ko) | 2011-01-25 |
JPWO2009119513A1 (ja) | 2011-07-21 |
JP5450386B2 (ja) | 2014-03-26 |
KR101522346B1 (ko) | 2015-05-21 |
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