WO2011114935A1 - Composition de résine époxyde et substance durcie - Google Patents

Composition de résine époxyde et substance durcie Download PDF

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Publication number
WO2011114935A1
WO2011114935A1 PCT/JP2011/055302 JP2011055302W WO2011114935A1 WO 2011114935 A1 WO2011114935 A1 WO 2011114935A1 JP 2011055302 W JP2011055302 W JP 2011055302W WO 2011114935 A1 WO2011114935 A1 WO 2011114935A1
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WO
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Prior art keywords
epoxy resin
resin composition
curing
epoxy
anhydride
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PCT/JP2011/055302
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English (en)
Japanese (ja)
Inventor
篤彦 片山
スレスタ・二ランジャン・クマール
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新日鐵化学株式会社
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Priority to JP2012505621A priority Critical patent/JP5676563B2/ja
Publication of WO2011114935A1 publication Critical patent/WO2011114935A1/fr

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Classifications

    • 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
    • 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
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3218—Carbocyclic compounds
    • 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
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic
    • 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
    • C08G59/621—Phenols
    • 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 resins, bisphenol F type epoxy resins 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.
  • an epoxy resin excellent in low viscosity Japanese Patent No. 3339083 proposes an epoxy resin having an oxymethylene chain in a cyclohexane skeleton.
  • the epoxy resin having an oxymethylene chain in the cyclohexane skeleton is excellent in transparency and weather resistance as compared with an epoxy resin having an aromatic ring, but 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 that is excellent in low viscosity, heat resistance, low thermal expansion, and the like, and a cured product thereof.
  • this invention relates to the epoxy resin composition containing the epoxy resin represented by the following Formula (1) in the epoxy resin composition containing the epoxy resin and the hardening
  • the epoxy resin is preferably 1,2,4-triepoxyethylcyclohexane.
  • 1,2,4-Triepoxyethylcyclohexane is represented by the following formula (2).
  • the curing agent for epoxy resin is selected from amines, acid anhydrides, polyhydric phenols, imidazoles, Bronsted acid salts, dicyandiamides, organic acid hydrazides, polycarboxylic acids and organic phosphines. It is preferable that it is at least one compound.
  • the present invention relates to the above epoxy resin composition containing 83 wt% or more of the inorganic filler.
  • the present invention relates to the above-mentioned epoxy resin composition for encapsulating electric / electronic parts and the cured epoxy resin obtained by curing the above epoxy resin composition.
  • the epoxy resin composition of the present invention includes 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 essential component and the inorganic filler are the main components.
  • the epoxy resin composition of the present invention is characterized by the structure of the epoxy resin represented by the formula (1), and is excellent in low viscosity by bonding an epoxy group and cyclohexane via an ether bond, and Gives a cured product with excellent heat resistance and low thermal expansion. Therefore, appropriate conditions can be used for the type and amount of additives such as epoxy resin curing agents.
  • the epoxy resin used in the epoxy resin composition of the present invention is represented by the formula (1).
  • substitution position of the epoxyethyl group in the epoxy resin of the formula (1) is not particularly limited, but is preferably 1,2 represented by the formula (2) substituted at the 1-position, 2-position and 4-position of the cyclohexane skeleton. 4-Triepoxyethylcyclohexane.
  • the epoxy resin component used in the present invention can be used in combination with other epoxy resins 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.
  • Two or more of these other epoxy resins may be used in combination. When these other epoxy resins are used in combination, the amount used is preferably 50 wt% or less, more preferably 20 wt% or less of the total epoxy resin.
  • Examples of the curing agent for epoxy resin used in the epoxy resin composition of the present invention include the following.
  • Aliphatic and alicyclic amines such as undecane, metaphenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diethyltoluenediamine, 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3 , 5-diethyl-2,6-diaminobenzene, 1,3,5-triethyl-2,6-diaminobenzene, 3,3′-diethyl-4,4′-diaminodiphenylmethane, 3,5,3 ′, 5 Aromatic amines such as' -tetramethyl
  • Acid anhydrides aromatic anhydrides such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride Cyclic aliphatic acid anhydrides such as methylendomethylenetetrahydrophthalic anhydride, cyclododecenyl succinic anhydride, and trialkyltetrahydrophthalic anhydride.
  • Multivalent phenols such as catechol, resorcin, hydroquinone, bisphenol F, bisphenol A, bisphenol S, biphenol, phenol novolacs, cresol novolacs, bisphenol A, etc.
  • imidazoles such as 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole and their salts, dicyandiamides and organic acid hydrazides.
  • These epoxy resin curing agents may be used singly or in combination of two or more.
  • polyamines and polyvalent hydroxy compounds suitable for semiconductor encapsulating materials are preferably used in terms of heat resistance, moisture resistance, electrical characteristics, and the like.
  • polyamines and acid anhydrides are particularly preferably used for resin applications that require heat resistance, moisture resistance, electrical characteristics, and transparency.
  • Polyamines include aliphatic amines such as polyethylenediamine, metaxylenediamine, trimethylhexamethylenediamine and 2-methylpentanemethylenediamine, isophoronediamine, 1,3-bisaminomethylcyclohexane, bis (4-aminocyclohexyl) methane, Preferred are alicyclic polyamines such as norborneneamine, 1,2-diaminocyclohexane and bis (4-amino-3-methylcyclohexyl) methane, and aromatic polyamines such as diaminodiphenylmethane, metaphenylenediamine, diaminodiphenylsulfone and diethyltoluenediamine. Can be mentioned.
  • aliphatic amines such as polyethylenediamine, metaxylenediamine, trimethylhexamethylenediamine and 2-methylpentanemethylenediamine, isophoronediamine, 1,3-bisamino
  • polyvalent hydroxy compound examples include 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.
  • 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,
  • novolac resins are particularly preferable because they are excellent in terms of heat resistance, moisture resistance, electrical characteristics, and the like.
  • 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 preferable melt viscosity in 150 degreeC is 1 Pa * s or less, More preferably, it is 0.5 Pa * s or less.
  • the viscosity at 25 ° C. when the epoxy resin composition (not including inorganic filler) is 0.00. It is appropriately selected so as to be 01 to 100 Pa ⁇ s.
  • Preferable examples include novolak resins available as Amanukawa Kogyo Co., Ltd. Tamanol PA, Tamanol 531, Tamanol 758, Tamanol 759, DIC Corporation TD-2131, TD-2106, TD-2091, TD-2090.
  • Acid anhydrides include hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, 3-methylhexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, 3-methyltetrahydrophthalic anhydride, 4-methyltetrahydro Including phthalic anhydride, methyl nadic anhydride, dodecenyl succinic anhydride, Diels-Alder reaction product of decatriene and maleic anhydride such as ⁇ -terpinene and alloocimene and their hydrogenated products, structural isomers or geometric isomers, Those mixed modified products are preferred. More preferred are these hydrogenated products.
  • the equivalent ratio of the functional group of the curing agent and the epoxy group of the epoxy resin is preferably in the range of 0.5 to 2.0. Preferably, it is in the range of 0.8 to 1.2.
  • a curing accelerator is preferably blended separately from the epoxy resin curing agent.
  • the curing accelerator those known as curing accelerators for epoxy resins can be used. Tris (dimethylaminomethyl) phenol, benzyldimethylamine, 1,8-diazabicyclo (5,4,0) undecene-7 Tertiary amines such as (DBU), imidazoles such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole and their salts, organic phosphines such as dicyandiamide, triphenylphosphine, etc. Is preferred.
  • DBU dimethylaminomethyl
  • imidazoles such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole and their salts
  • organic phosphines such as dicyandiamide, triphenylphosphine, etc. Is preferred.
  • These curing accelerators
  • the epoxy resin composition of the present invention preferably has a low viscosity in order to blend the inorganic filler with a high content. Therefore, the viscosity of the epoxy resin composition with the inorganic filler removed from the epoxy resin composition is set to 0.01 to 100 Pa ⁇ s, preferably 0.1 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 above 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.
  • the epoxy resin represented by the above formula (1) can be obtained by using trivinylcyclohexane as a raw material and oxidizing the vinyl group with a peroxide to carry out an epoxidation reaction.
  • the epoxy resin represented by the above formula (2) is obtained using 1,2,4-trivinylcyclohexane as a raw material.
  • the peroxide used in the epoxidation reaction a known production method can be adopted, and specifically, a normal peracid or an organic peroxide is used. Examples include performic acid, peracetic acid, perpropionic acid, m-chlorobenzoic acid and the like.
  • Examples 1 to 3 and Comparative Examples 1 to 4 An epoxy resin composition was prepared by kneading using the following epoxy resin, curing agent, and curing accelerator at the blending ratios shown in Tables 1 and 2.
  • the brackets in Tables 1 and 2 represent parts by weight.
  • an epoxy resin EP-a represented by the above formula (2) (epoxy equivalent 93 / eq. Viscosity at 25 ° C. is 115 mPa ⁇ s), for comparison, an epoxy resin having an oxymethylene chain in a cyclohexane skeleton 1,4-cyclohexanedimethanol diglycidyl ether epoxy resin EP-b (manufactured by Shin Nippon Rika Co., Ltd., DME-100; epoxy equivalent 158 g / eq, viscosity at 25 ° C.
  • PN phenol novolak resin, manufactured by Arakawa Chemical, Tamanol 758; OH equivalent 103, softening point 82 ° C.
  • MH-700 4-methylhexahydrophthalic anhydride / hexahydrophthalic anhydride mixture (70/30 ), Shin Nippon Rika Co., Ltd., Ricacid MH-700
  • EC-100 1-methyl-3,5-diethyl-2,4-diaminobenzene and 1-methyl-3,5-diethyl-2,6-diamino
  • Ecure 100 manufactured by Albemarle Japan Ltd. was used.
  • 2E4MZ (2-ethyl-4-methylimidazole) was used as a curing accelerator component.
  • fillers 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 Admatechs Co., Ltd. A mixture of four types, 0.9 ⁇ m diameter) and SO—C2 (average particle diameter 0.5 ⁇ m) was used. The mixing ratio was 20: 50: 10: 20 by weight.
  • 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.
  • the gel time the epoxy resin composition was poured into the concave portion of a gelation tester (Nisshin Kagaku Co., Ltd.) that had been heated to 175 ° C. in advance, and a speed of two revolutions per second using a fluororesin rod. And 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.
  • the epoxy resin composition of the present invention has a low viscosity before curing, good fluidity at the time of moldability, and can give a cured product excellent in heat resistance, moisture resistance, low thermal expansion and the like. Recognize. These cured products are useful for electrical / electronic component sealing materials such as semiconductor sealing materials, molding materials, laminated materials, adhesive materials, and the like.
  • 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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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

L'invention porte sur une composition de résine époxyde ayant une faible viscosité avant durcissement, qui présente une bonne fluidité pendant le moulage et a d'autres bonnes propriétés, parmi lesquels une grande résistance à la chaleur et à l'humidité et un faible degré de dilatation thermique. Une telle composition de résine époxyde est utile par exemple en tant que matériau d'étanchéité pour des composants électriques/électroniques (par exemple un matériau d'étanchéité pour semi-conducteur), un matériau à mouler, un matériau pour stratification ou un matériau adhésif. La composition de résine époxyde présentée contient une résine époxyde et un durcisseur de résine époxyde, ladite résine époxyde étant une résine époxyde de triépoxyéthylmicrohexane, représentée par la formule (1).
PCT/JP2011/055302 2010-03-18 2011-03-08 Composition de résine époxyde et substance durcie WO2011114935A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012020661A1 (fr) * 2010-08-09 2012-02-16 新日鐵化学株式会社 Composition de résine époxy et durcissant
WO2012108305A1 (fr) * 2011-02-10 2012-08-16 新日鐵化学株式会社 Époxy-acrylate, composition durcissable acrylique, produit durci et procédé de fabrication s'y rapportant
WO2014066718A1 (fr) * 2012-10-26 2014-05-01 Dow Global Technologies Llc Compositions durcissables contenant des composés époxy à base de 1,3-dioxiranylcyclopentane et résines thermodurcissables préparées à partir de celles-ci
WO2014066717A1 (fr) * 2012-10-26 2014-05-01 Dow Global Technologies Llc Composés époxy inédits : dérivés de 1,3-dioxiranylcyclopentane
KR20220104959A (ko) * 2021-01-19 2022-07-26 한국화학연구원 삼관능성 지환족 에폭시 화합물을 포함하는 에폭시 수지 제조용 조성물 및 이를 이용한 경화물

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GB930431A (en) * 1960-10-03 1963-07-03 Rhone Poulenc Sa Epoxide derivatives of trivinylcyclohexane
US3251861A (en) * 1966-05-17 Di- and triepoxtoe derivatives of trivinylcyclohexane
JPH103084A (ja) * 1996-06-18 1998-01-06 Sumitomo Bakelite Co Ltd 液晶表示素子用シール材組成物及びそれを用いた液晶表示素子
JP2007197647A (ja) * 2005-12-27 2007-08-09 Sumitomo Electric Ind Ltd 液状熱硬化性樹脂組成物、および接合材

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WO2005056675A1 (fr) * 2003-11-21 2005-06-23 Lord Corporation Agents d'encapsulation appliques a une plaquette a deux etages

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Publication number Priority date Publication date Assignee Title
US3251861A (en) * 1966-05-17 Di- and triepoxtoe derivatives of trivinylcyclohexane
GB930431A (en) * 1960-10-03 1963-07-03 Rhone Poulenc Sa Epoxide derivatives of trivinylcyclohexane
JPH103084A (ja) * 1996-06-18 1998-01-06 Sumitomo Bakelite Co Ltd 液晶表示素子用シール材組成物及びそれを用いた液晶表示素子
JP2007197647A (ja) * 2005-12-27 2007-08-09 Sumitomo Electric Ind Ltd 液状熱硬化性樹脂組成物、および接合材

Cited By (10)

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