WO2004069928A1 - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
- Publication number
- WO2004069928A1 WO2004069928A1 PCT/JP2003/016667 JP0316667W WO2004069928A1 WO 2004069928 A1 WO2004069928 A1 WO 2004069928A1 JP 0316667 W JP0316667 W JP 0316667W WO 2004069928 A1 WO2004069928 A1 WO 2004069928A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- resin composition
- epoxy
- epoxidized
- molecular weight
- Prior art date
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 100
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 38
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 38
- 229920001195 polyisoprene Polymers 0.000 claims abstract description 38
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 abstract description 9
- 230000001070 adhesive effect Effects 0.000 abstract description 8
- 239000004065 semiconductor Substances 0.000 abstract description 7
- 239000000853 adhesive Substances 0.000 abstract description 6
- 238000005538 encapsulation Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 39
- 239000004593 Epoxy Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 238000005452 bending Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- -1 vinyl aromatic hydrocarbons Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 5
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 5
- 229920003051 synthetic elastomer Polymers 0.000 description 5
- 239000005061 synthetic rubber Substances 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241001282736 Oriens Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- ORICWOYODJGJMY-UHFFFAOYSA-N dibutyl(phenyl)phosphane Chemical compound CCCCP(CCCC)C1=CC=CC=C1 ORICWOYODJGJMY-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N peroxyacetic acid Substances CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- PADOFXALCIVUFS-UHFFFAOYSA-N tris(2,3-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C(=C(OC)C=CC=2)OC)C=2C(=C(OC)C=CC=2)OC)=C1OC PADOFXALCIVUFS-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
Definitions
- the present invention relates to an epoxy resin composition.
- the epoxy resin composition obtained by the present invention is excellent in heat resistance and realizes relaxation of internal stress, and can be suitably used for electronic component materials represented by semiconductor encapsulating materials, adhesive applications, and the like.
- Cured products obtained from epoxy resin-based compositions have excellent adhesive properties, heat resistance, and electrical properties, and are used in a wide variety of applications, including electrical and electronic components such as semiconductor sealing materials, adhesives, and paints.
- electrical and electronic components such as semiconductor sealing materials, adhesives, and paints.
- a cured product is inherently poor in flexibility and brittle, so that internal stress is inevitably accumulated during curing, and as a result, cracks occur in cast products such as electronic parts.
- Adhesives had problems such as poor adhesion, and paints had problems such as cracking and peeling.
- the characteristics required in the field of electronic components and adhesives have become increasingly severe in recent years, and there is a need to improve physical properties such as strength and low elastic modulus while maintaining heat resistance.
- Techniques that can solve these problems and alleviate internal stress during curing include, for example, ⁇ 1> polyfunctional epoxy compounds, reaction condensates of phenolic compounds with formaldehyde, and at least one or more per molecule.
- thermosetting resin composition containing a polybutadiene derivative having a hydroxyl group and an isocyanate group as an essential component see Japanese Patent Application Laid-Open No. 57-186626; ⁇ 2> Epoxy at the terminal or in the molecule
- An epoxy resin composition containing 0.1 to 5% by mass of a synthetic rubber containing a group has been proposed.
- ⁇ 3> toughness is provided which contains a curable aromatic and / or curable alicyclic epoxy resin, a curing agent, and an epoxidized low-viscosity polymer polymer having a specific epoxy content and preferably a specific structure.
- Epoxy resin composition containing a hydroxyl group-containing substance in addition to such a composition see Japanese Patent Application Laid-Open No. Hei 10-125039). No. 96) has been proposed.
- compositions ⁇ 1> to ⁇ 4> are said to impart flexibility by internal plasticization. It is based on technical ideas.
- Japanese Patent Application Laid-Open No. 57-180626 discloses that at least one or more carbonyl group, amino group, hydroxyl group, epoxy group, thiol group, etc.
- the “polybutadiene derivative having an isocyanate group” is a low molecular weight polybutadiene having a functional group at a terminal (2800, 4600 and 4800 used in Examples), and JP-A-61-62511.
- the particularly preferred molecular weight of the “synthetic rubber containing an epoxy group at the terminal or in the molecule” disclosed as substantially useful in ⁇ 2>) is 700 to 3000 (the number average molecular weight of 700 used in Examples).
- the epoxy equivalent of the synthetic rubber containing an epoxy group in the molecule is 190-220 (5.3-4.5 meq / g as the epoxy value), and the epoxy group content is high.
- a composition containing such a low molecular weight polybutene modified with many functional groups there is a problem that heat resistance is reduced.
- synthetic rubbers containing an epoxy group at the end are generally produced by reaction with epichlorohydrin, but such synthetic rubbers contain many impurities such as chloride ions by-produced in the production process.
- the epoxy resin composition has corrosiveness when used for metal parts.
- epoxy resin compositions disclosed in Japanese Patent Publication No. 9-1512039 ( ⁇ 3>) and Japanese Patent Publication No. 10-502696 ( ⁇ 4>) are characterized by imparting toughness.
- the "epoxidized low viscosity polydiene polymers" disclosed as being substantially useful are low molecular weight block polymers containing vinyl aromatic hydrocarbons (4960, 5680, 6000, and Particularly preferred epoxy value is (i) 3.5 to 6 meqZg when the content of vinyl aromatic hydrocarbon is less than 5%; (ii) when the content of pinyl aromatic hydrocarbon is 5 to 20 %: 3-6 meq / g; (iii) 1.5-6 meq / g when the content of vinyl aromatic hydrocarbons is 20% or more.
- an object of the present invention is to provide an excellent heat resistance, sufficient internal stress, and sufficient flexibility to solve problems such as crack generation, adhesion, and peeling of a coating interface due to internal stress. Grant To provide an epoxy resin composition. Disclosure of the invention
- the object is to provide (A) an epoxy resin, (B) a curing agent, and (C) an epoxy group in a molecule in a range of 0.1 to 2 meq / g and a number average molecular weight.
- Epoxidized polyisoprene (c-11) (hereinafter abbreviated as epoxidized polyisoprene (c-11)) or an epoxy group in the molecule in the range of 0.1 to 2 meqZg.
- Epoxidized polybutene (c-12) hereinafter abbreviated as epoxidized polybutadiene (c-2)) having a number average molecular weight in the range of 20,000 to 200,000. Achieved by providing. BEST MODE FOR CARRYING OUT THE INVENTION
- the epoxy resin (A) constituting the epoxy resin composition of the present invention is not particularly limited as long as it can be cured by a curing agent (B).
- a curing agent B
- at least two epoxy groups in one molecule may be used.
- the contained epoxy resin can be suitably used. Specifically, there are a piphenyl epoxy resin, a naphthalene epoxy resin, a diphenyl ether epoxy resin, a diphenyl thioether epoxy resin, a hydroquinone epoxy resin, a biphenyl nopolak epoxy resin, and a cresol nopolak.
- Epoxy resin phenol nopolak epoxy resin, bisphenol A nopolak epoxy resin, trisphenolic epoxy resin, tetraphenylol ethane epoxy resin, dicyclopentagen epoxy resin, bisphenol A epoxy resin And bisphenol F-type epoxy resins.
- One of these epoxy resins may be used alone, or two or more thereof may be used in combination.
- the curing agent (B) constituting the epoxy resin composition of the present invention for example, a phenol resin having two or more phenolic hydroxyl groups in one molecule can be suitably used. Specifically, phenol nopolak resin, resole type phenol resin, phenol aralkyl resin, triphenol alkane resin, and polymers thereof, naphthalene ring-containing phenol resin, dicyclopentagen-modified phenol resin And the like.
- the compounding amount of the curing agent (B) is preferably from 20 to 250 parts by mass, more preferably from 20 to 125 parts by mass, per 100 parts by mass of the epoxy resin (A).
- the amount of the curing agent (B) is 100 parts by mass of the epoxy resin (A). If the amount is less than 20 parts by mass, the unreacted component of the epoxy resin (A) when the epoxy resin composition is cured tends to increase, while if it is more than 250 parts by mass, the curing agent (B) ) Tends to increase.
- the epoxidized polyisoprene (c-11) constituting the epoxy resin composition of the present invention contains an epoxy group in the molecule in a range of 0.15 to 2 meq / g, and has a number average molecular weight of 15,000 to 200,000. In the range.
- the epoxidized polybutadiene (c_2) constituting the epoxy resin composition of the present invention contains an epoxy group in the molecule in the range of 0.15 to 2 meq / g and has a number average molecular weight of 20,000 to 200,000. It is characterized by being within the range.
- the epoxy group content of the epoxidized polyisoprene (c-1) or the epoxidized polybutadiene (c-2) is less than 0.15 meq / g, the compatibility with the epoxy resin (A) becomes low, and the epoxy resin composition Bleed-out of the epoxidized polyisoprene (c-11) or the epoxidized polybutadiene (c-12) becomes remarkable in the cured product of the cured product.
- the cured product tends to lose rubber elasticity due to a decrease in the cross-linking distance of the epoxidized polyisoprene (c-1) or epoxidized polybutadiene (c-2), resulting in brittleness. Becomes bigger.
- the cured product obtained by curing the epoxy resin composition Bleed out of epoxidized polyisoprene (c-1) or epoxidized polybutadiene (c-2) becomes remarkable.
- the number average molecular weight of the epoxidized polyisoprene (c-1) or the epoxidized polybutadiene (c-2) is 200,000 or more, the viscosity of the epoxidized polyisoprene (c-1) increases, and the workability in preparing the epoxy resin composition deteriorates.
- the number average molecular weight in the present specification means a number average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).
- the amount of the epoxidized polyisoprene (c-11) or epoxidized polybutadiene (c-12) is preferably 1 to 40 parts by mass, and more preferably 5 to 25 parts by mass per 100 parts by mass of the epoxy resin (A). More preferably, it is within the range.
- the epoxy resin composition of the present invention is used. In the cured product obtained from the curing of epoxy resin, there is a tendency that sufficient flexibility cannot be imparted. Bleed-out of epoxidized polyisoprene (c-11) or epoxidized polybutadiene (c-2) tends to occur in the cured product obtained by curing the xy-resin composition.
- the method for producing polyisoprene which is a raw material of the epoxidized polyisoprene (c-11), and polybutadiene, which is a raw material of the epoxidized polybutadiene (c-12), are not particularly limited.
- the law can be adopted.
- an alkaline solution such as sodium metal or lithium metal is used.
- Li-metal using an alkyllithium compound such as methyllithium, ethyllithium, n-butyllithium, s-butyllithium, etc. as an initiator, usually at a polymerization temperature of 100 to 100 ° C and a polymerization time of 0.01 to 200 It can be carried out by a method of polymerizing within a time range.
- an alkyllithium compound such as methyllithium, ethyllithium, n-butyllithium, s-butyllithium, etc.
- the carbon-carbon double bond in the molecular chain of the obtained polyisoprene or polybutadiene is epoxidized to obtain epoxidized polyisoprene (c-1) or epoxidized polybutadiene.
- the method of epoxidation is not particularly limited.
- a method of treating with a peracid such as 0-peracetic acid see JP-A-8-134135
- a treatment with a molybdenum complex and t-butyl hydroperoxide See LChem. Soc., Chem. Commun., P. 1686 (1989)
- tungstic acid catalyst and hydrogen peroxide J. Polym. Sci., C, Vol. 28, p.
- a method of treating with a tungsten compound selected from ammonium tungstate or phosphorus tungstate, a quaternary ammonium salt, phosphoric acid, and an aqueous solution of hydrogen peroxide (see JP-A-2002-249516)
- a curing accelerator and / or an inorganic filler may be further added to the epoxy resin composition of the present invention as long as the object and effects of the present invention are not impaired.
- curing accelerator examples include phosphines such as triphenylphosphine, tris (dimethoxyphenyl) phosphine and dibutylphenylphosphine; and amines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine.
- phosphines such as triphenylphosphine, tris (dimethoxyphenyl) phosphine and dibutylphenylphosphine
- amines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine.
- Examples of the inorganic filler include fused silica, crystalline silica, glass, and alumina. You. By adding these inorganic fillers, it is possible to improve the hygroscopicity, thermal conductivity and mechanical strength of the epoxy resin composition of the present invention. In addition, by adding an inorganic filler, the coefficient of linear expansion of the epoxy resin, which is higher than that of the metal, is reduced.For example, when used in semiconductor encapsulation applications, cracks and peeling due to temperature changes during molding should be reduced. Can be.
- the amount is not strictly limited, and the compounding amount may vary depending on the application.
- the amount of the filler is determined by the amount of the epoxy resin (A), the curing agent (B), the epoxidized polyisoprene (c-1) or the epoxidized polybutadiene (c-12), which constitute the epoxy resin composition.
- the curing accelerator is preferably in the range of 70 to 90% by mass based on the total mass of all the components including the inorganic filler.
- the epoxy resin composition of the present invention comprises an epoxy resin (A), a curing agent (B), an epoxidized polyisoprene (c-1) or an epoxidized polybutadiene (c-12), and, if necessary, a curing accelerator, Any method may be used as long as the filler and the like can be uniformly dispersed and mixed. For example, a method in which a predetermined amount of the above-mentioned material is sufficiently mixed by a mixer or the like, then melt-kneaded by a mixing roll, an extruder, or the like, and then cooled and ground.
- a transfer molding method is generally used as a molding method for preparing a molded product by curing the epoxy resin composition according to the present invention by heat, but it is also possible to use an injection molding method, a compression molding method, or the like. Good.
- the epoxy resin composition of the present invention is excellent in heat resistance and realizes relaxation of internal stress.
- the epoxy resin composition is a material having a low elastic modulus while maintaining bending strength, an electronic component represented by a semiconductor sealing material It can be suitably used for materials and adhesives.
- the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.
- the evaluation of the physical properties of the epoxy resin compositions in each of the examples and comparative examples was performed as follows.
- test pieces having a length of 10 O mm, a width of 1 O mm, and a thickness of 3 mm were prepared and measured at room temperature in accordance with JISK 6911.
- EP I CLON ⁇ — 665 (trade name): Cresol nopolak epoxy resin (manufactured by Dainippon Ink & Chemicals, Inc., epoxy value 4.7-5. Ome qZg, softening point 64-72 ° C) Curing agent (B)
- Phenolite TD-2131 (trade name): phenolic nopolak resin (manufactured by Dainippon Ink and Chemicals, Inc., hydroxyl value: 9.7 meq / g, softening point: 80 ⁇ 2 ° C)
- About 0.5 g of e-IR-1 was precisely weighed and dissolved in 1 Om1 of tetrahydrofuran (THF) at 25 ° C. To this solution was added 1 Oml of 0.2N hydrochloric acid in THF and stirred for 30 minutes. After reacting with the epoxy group in e-IR-1 and the excess hydrochloric acid, the epoxy value was measured by titration with 0.1N ethanol solution of potassium hydroxide. However, it was 0.15 meq / g.
- e_IR-2 epoxidized polyisoprene
- e-IR-3 epoxidized polyisoprene
- e-BR-2 epoxidized polybutadiene
- Mn 35300
- Mw / Mn 1.02.
- the epoxy value of e-BR-2 was measured by the hydrochloric acid reverse titration method in the same manner as in ⁇ 2> of Reference Example 1, and it was 0.52 meq / g.
- An epoxy resin composition was prepared in a barrel in the same manner as in Example 1 except that e-IR-1 was not added, and physical properties of the barrel were evaluated. Table 1 shows the results.
- Example 1 was repeated except that 9 parts by mass of the polyisoprene having the number average molecular weight (M n) of 270,000 obtained in Reference Example 1 ⁇ 1> was used in place of e-IR-1 in Example 1.
- An epoxy resin composition was obtained in the same manner as described above, and its physical properties were evaluated. Table 1 shows the results.
- E-1000-8.0 manufactured by Nippon Oil Co., Ltd.
- Mn 40
- Mw 4200
- epoxy value 5.0 An epoxy resin composition was obtained in the same manner as in Example 1 except that 9 parts by mass of meq / g) was used, and its physical properties were evaluated. Table 1 shows the results.
- Example 1 epoxidized polybutadiene was used instead of e-IR-1: trade name "E-1"
- composition ratio of ingredients that make up the extruded composition (quality 1)
- FIG. 1 shows E ′ of the cured product obtained from the three types of epoxy resin compositions of Example 1, Example 2, and Comparative Example 1, and FIG. 2 shows Example 1, Comparative Example 1, Comparative Example 2, and Comparative Example.
- Fig. 3 shows E 'of the cured product obtained from the four types of epoxy resin compositions of Example 1, Comparative Example 1, Comparative Example 4, and Comparative Example 5 obtained from the four types of epoxy resin compositions.
- FIG. 4 shows E ′ of the cured product obtained from the three types of epoxy resin compositions of Example 1, Comparative Example 1 and Comparative Example 6, and FIG. 5 shows Example 3 and Example.
- FIG. 6 shows E ′ of the cured product obtained from the three types of epoxy resin compositions of Comparative Example 4 and Comparative Example 1, and FIG.
- FIG. 6 shows the results obtained from the three types of epoxy resin compositions of Example 3, Comparative Example 1 and Comparative Example 7.
- FIG. 7 shows the E ′ of the cured product
- FIG. 7 shows the E ′ of the cured product obtained from the four types of epoxy resin compositions of Example 3, Comparative Example 1, Comparative Example 4, and Comparative Example 5,
- FIG. 9 shows E ′ of the cured products obtained from the three types of epoxy resin compositions of Example 3, Comparative Example 1 and Comparative Example 6.
- Table 1 it can be seen that a cured product obtained from the epoxy resin composition of the present invention containing an epoxidized polyisoprene (c-1) or an epoxidized polybutadiene (c-2) having a specific range of epoxy value (Example 1).
- the temperature at which E ′ starts to rapidly decrease is defined as the softening onset temperature of the cured products obtained from the epoxy resin compositions of the respective Examples and Comparative Examples, that is, the heat resistance index. It can be. From FIGS. 1 and 5, the cured product obtained from the epoxy resin composition of the present invention containing the epoxidized polyisoprene (c-11) or epoxidized polybutadiene (c-12) having an epoxy value in a specific range (FIG.
- Examples 1-4 were the same as the cured product obtained from the epoxy resin composition of Comparative Example 1 in which the epoxidized polyisoprene (c-11) or the epoxidized polybutadiene (c-2) was not blended. Since E 'is maintained around C, it can be seen that the heat resistance is not impaired. ⁇
- FIGS. 2 and 6 show that unmodified polyisoprene, epoxidized polyisoprene having an epoxy value outside the range of the present invention, or unmodified polybutadiene (Comparative Examples 2, 3, and 7) were similarly added. It can be seen that E ′ is maintained up to around 150 ° C, but the cured products obtained from these compositions can achieve a low elastic modulus as described above, but have an improved fracture bending strength. Has the disadvantage that it is not enough.
- CTBN Comparative Example 4
- epoxidized polybutadiene having an epoxy value outside the range specified in the present invention Comparative Examples 5 and 6 were blended.
- the decrease in E ′ began at a lower temperature than the cured products obtained from the epoxy resin compositions of Example 1 and Example 3. Is inferior in heat resistance.
- the internal stress can be reduced without lowering the heat resistance, and an epoxy resin composition having sufficient flexibility can be obtained.
- the epoxy resin composition obtained by the present invention is excellent in heat resistance and realizes relaxation of internal stress, and can be suitably used for electronic component materials represented by semiconductor encapsulating materials, adhesives, and the like.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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US10/544,762 US7652104B2 (en) | 2003-02-10 | 2003-12-25 | Epoxy resin composition |
AT03768202T ATE503800T1 (de) | 2003-02-10 | 2003-12-25 | Epoxidharz-zusammensetzung |
DE60336591T DE60336591D1 (de) | 2003-02-10 | 2003-12-25 | Epoxidharz-zusammensetzung |
CA002514994A CA2514994C (en) | 2003-02-10 | 2003-12-25 | Epoxy resin composition |
EP03768202A EP1607441B1 (en) | 2003-02-10 | 2003-12-25 | Epoxy resin composition |
AU2003292782A AU2003292782A1 (en) | 2003-02-10 | 2003-12-25 | Epoxy resin composition |
Applications Claiming Priority (4)
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JP2003-32765 | 2003-02-10 | ||
JP2003032765A JP4098108B2 (ja) | 2003-02-10 | 2003-02-10 | エポキシ樹脂組成物 |
JP2003032764A JP4098107B2 (ja) | 2003-02-10 | 2003-02-10 | 熱硬化性樹脂組成物 |
JP2003-32764 | 2003-02-10 |
Publications (1)
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WO2004069928A1 true WO2004069928A1 (ja) | 2004-08-19 |
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PCT/JP2003/016667 WO2004069928A1 (ja) | 2003-02-10 | 2003-12-25 | エポキシ樹脂組成物 |
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US (1) | US7652104B2 (ja) |
EP (1) | EP1607441B1 (ja) |
KR (1) | KR100690221B1 (ja) |
AT (1) | ATE503800T1 (ja) |
AU (1) | AU2003292782A1 (ja) |
CA (1) | CA2514994C (ja) |
DE (1) | DE60336591D1 (ja) |
WO (1) | WO2004069928A1 (ja) |
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KR100851263B1 (ko) | 2003-02-28 | 2008-08-08 | 가부시키가이샤 구라레 | 경화성 수지 조성물 |
KR100648648B1 (ko) * | 2005-10-14 | 2006-11-23 | 헨켈코리아 주식회사 | 차체에 강도 및 제진성을 동시에 부여하는 시트 조성물 및그 시트 |
WO2007061037A1 (ja) * | 2005-11-25 | 2007-05-31 | Hitachi Chemical Co., Ltd. | 電子部品用液状樹脂組成物及び電子部品装置 |
DE102012201873B4 (de) | 2012-02-08 | 2016-03-10 | Franken Systems Gmbh | Verfahren zur Bauwerksabdichtung mittels gewebearmierter Beschichtung |
JP6672174B2 (ja) | 2014-12-25 | 2020-03-25 | 株式会社クラレ | 変性液状ジエン系ゴム及び該変性液状ジエン系ゴムを含む樹脂組成物 |
WO2019127172A1 (en) * | 2017-12-28 | 2019-07-04 | Henkel Ag & Co. Kgaa | Epoxy based composition |
CN113072862B (zh) * | 2021-04-28 | 2022-08-19 | 山东冠通交通设施有限公司 | 一种抗裂自修复环氧地坪涂料及其制备工艺 |
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-
2003
- 2003-12-25 CA CA002514994A patent/CA2514994C/en not_active Expired - Fee Related
- 2003-12-25 AU AU2003292782A patent/AU2003292782A1/en not_active Abandoned
- 2003-12-25 US US10/544,762 patent/US7652104B2/en not_active Expired - Fee Related
- 2003-12-25 AT AT03768202T patent/ATE503800T1/de not_active IP Right Cessation
- 2003-12-25 KR KR1020057015154A patent/KR100690221B1/ko active IP Right Grant
- 2003-12-25 DE DE60336591T patent/DE60336591D1/de not_active Expired - Lifetime
- 2003-12-25 WO PCT/JP2003/016667 patent/WO2004069928A1/ja active Application Filing
- 2003-12-25 EP EP03768202A patent/EP1607441B1/en not_active Expired - Lifetime
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JPS57180626A (en) * | 1981-04-30 | 1982-11-06 | Hitachi Ltd | Thermosetting resin composition |
JPS6162511A (ja) * | 1984-09-05 | 1986-03-31 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物 |
EP0632074A2 (en) * | 1993-06-29 | 1995-01-04 | Shell Internationale Researchmaatschappij B.V. | Viscous conjugated diene block copolymers |
US5332783A (en) * | 1993-07-12 | 1994-07-26 | Shell Oil Company | Compatible blends of epoxy resins and epoxidized polydienes |
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Also Published As
Publication number | Publication date |
---|---|
CA2514994C (en) | 2008-04-01 |
US20060142507A1 (en) | 2006-06-29 |
KR100690221B1 (ko) | 2007-03-12 |
EP1607441A1 (en) | 2005-12-21 |
EP1607441B1 (en) | 2011-03-30 |
US7652104B2 (en) | 2010-01-26 |
CA2514994A1 (en) | 2004-08-19 |
KR20050107578A (ko) | 2005-11-14 |
ATE503800T1 (de) | 2011-04-15 |
EP1607441A4 (en) | 2006-05-10 |
DE60336591D1 (de) | 2011-05-12 |
AU2003292782A1 (en) | 2004-08-30 |
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