WO2013077351A1 - Mélange de résines époxy, composition de résine époxy, préimprégné et produits polymérisés à base de ceux-ci - Google Patents
Mélange de résines époxy, composition de résine époxy, préimprégné et produits polymérisés à base de ceux-ci Download PDFInfo
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- WO2013077351A1 WO2013077351A1 PCT/JP2012/080153 JP2012080153W WO2013077351A1 WO 2013077351 A1 WO2013077351 A1 WO 2013077351A1 JP 2012080153 W JP2012080153 W JP 2012080153W WO 2013077351 A1 WO2013077351 A1 WO 2013077351A1
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- WIPO (PCT)
- Prior art keywords
- epoxy resin
- group
- carbon atoms
- formula
- resin composition
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 165
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 165
- 239000000203 mixture Substances 0.000 title claims abstract description 95
- -1 phenol compound Chemical class 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000011256 inorganic filler Substances 0.000 claims description 18
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 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 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004065 semiconductor Substances 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005543 phthalimide group Chemical group 0.000 claims description 3
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 3
- 238000005538 encapsulation Methods 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000047 product Substances 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 150000002989 phenols Chemical class 0.000 description 22
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 18
- 238000005406 washing Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000004593 Epoxy Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
- 238000006735 epoxidation reaction Methods 0.000 description 10
- 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 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 8
- 238000010926 purge Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 6
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 5
- 235000012141 vanillin Nutrition 0.000 description 5
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 3
- GSOHKPVFCOWKPU-UHFFFAOYSA-N 3-methylpentane-2,4-dione Chemical compound CC(=O)C(C)C(C)=O GSOHKPVFCOWKPU-UHFFFAOYSA-N 0.000 description 3
- YNMZZHPSYMOGCI-UHFFFAOYSA-N Aethyl-octyl-keton Natural products CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 2
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
- YNPDFBFVMJNGKZ-UHFFFAOYSA-N 2'-Hydroxy-5'-methylacetophenone Chemical compound CC(=O)C1=CC(C)=CC=C1O YNPDFBFVMJNGKZ-UHFFFAOYSA-N 0.000 description 2
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-UHFFFAOYSA-N 0.000 description 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 2
- WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 description 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CJPNOLIZCWDHJK-UHFFFAOYSA-N 2-Pentadecanone Chemical compound CCCCCCCCCCCCCC(C)=O CJPNOLIZCWDHJK-UHFFFAOYSA-N 0.000 description 2
- POQLVOYRGNFGRM-UHFFFAOYSA-N 2-Tetradecanone Chemical compound CCCCCCCCCCCCC(C)=O POQLVOYRGNFGRM-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- UCQUAMAQHHEXGD-UHFFFAOYSA-N 3',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1 UCQUAMAQHHEXGD-UHFFFAOYSA-N 0.000 description 2
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 2
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 description 2
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 2
- XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 description 2
- FEUATHOQKVGPEK-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarbaldehyde Chemical compound OC1=CC=C(C=O)C=C1C=O FEUATHOQKVGPEK-UHFFFAOYSA-N 0.000 description 2
- PQCLJXVUAWLNSV-UHFFFAOYSA-N 5-Methyl-2,3-hexanedione Chemical compound CC(C)CC(=O)C(C)=O PQCLJXVUAWLNSV-UHFFFAOYSA-N 0.000 description 2
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- LTMXHUUHBSCKEK-UHFFFAOYSA-N Hexadecan-3-one Chemical compound CCCCCCCCCCCCCC(=O)CC LTMXHUUHBSCKEK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- DOACSXJVHDTDSG-UHFFFAOYSA-N henicosan-11-one Chemical compound CCCCCCCCCCC(=O)CCCCCCCCCC DOACSXJVHDTDSG-UHFFFAOYSA-N 0.000 description 1
- YAVJSVDUZGIQPQ-UHFFFAOYSA-N heptyl 3-oxobutanoate Chemical compound CCCCCCCOC(=O)CC(C)=O YAVJSVDUZGIQPQ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- QNZLAXONNWOLJY-UHFFFAOYSA-N hexyl 3-oxobutanoate Chemical compound CCCCCCOC(=O)CC(C)=O QNZLAXONNWOLJY-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- KNRCVAANTQNTPT-UHFFFAOYSA-N methyl-5-norbornene-2,3-dicarboxylic anhydride Chemical compound O=C1OC(=O)C2C1C1(C)C=CC2C1 KNRCVAANTQNTPT-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- IKYDDBGYKFPTGF-UHFFFAOYSA-N octyl 3-oxobutanoate Chemical compound CCCCCCCCOC(=O)CC(C)=O IKYDDBGYKFPTGF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- PFTIWTQFHWICDR-UHFFFAOYSA-N pentan-3-yl 3-oxobutanoate Chemical compound CCC(CC)OC(=O)CC(C)=O PFTIWTQFHWICDR-UHFFFAOYSA-N 0.000 description 1
- DMCJFWXGXUEHFD-UHFFFAOYSA-N pentatriacontan-18-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCCCCCCCCCC DMCJFWXGXUEHFD-UHFFFAOYSA-N 0.000 description 1
- IDZAUPYMMSSVHP-UHFFFAOYSA-N pentyl 3-oxobutanoate Chemical compound CCCCCOC(=O)CC(C)=O IDZAUPYMMSSVHP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G59/18—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- 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
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a novel epoxy resin mixture and an epoxy resin composition. Moreover, it is related with hardened
- Epoxy resin compositions are generally cured products with excellent mechanical properties, water resistance, chemical resistance, heat resistance, electrical properties, etc., such as adhesives, paints, laminates, molding materials, casting materials, etc. It is used in a wide range of fields. In recent years, cured products of epoxy resins used in these fields have begun to be highly purified and have various properties such as flame retardancy, heat resistance, moisture resistance, toughness, low linear expansion coefficient, and low dielectric constant characteristics. There is a need for improvement.
- Patent Document 1 As a means for realizing high thermal conductivity of an epoxy resin, it is reported in Patent Document 1 that a mesogenic group is introduced into the structure.
- an epoxy resin having a mesogenic group an epoxy resin having a biphenyl skeleton, etc. Is described.
- an epoxy resin other than the biphenyl skeleton a phenyl benzoate type epoxy resin is described.
- the epoxy resin needs to be produced by an epoxidation reaction by oxidation, there are difficulties in safety and cost, and it is practical. It can not be said.
- Patent Documents 2 to 4 Examples of using an epoxy resin having a biphenyl skeleton include Patent Documents 2 to 4, and among them, Patent Document 3 describes a technique in which an inorganic filler having a high thermal conductivity is used in combination.
- the thermal conductivity of the cured product obtained by the methods described in these documents is not at a level that satisfies the market demand, and a cured product having higher thermal conductivity using an epoxy resin that is available at a relatively low cost.
- an epoxy resin composition that provides.
- Japanese Unexamined Patent Publication No. 11-323162 Japanese Unexamined Patent Publication No. 2004-2573 Japanese Unexamined Patent Publication No. 2006-63315 Japanese Unexamined Patent Publication No. 2003-137971
- the present invention has been made as a result of studies to solve such problems, and provides an epoxy resin mixture in which the cured product has high thermal conductivity, low viscosity and excellent workability.
- each R 1 is independently present and is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or an alkoxy having 1 to 10 carbon atoms.
- each R 2 is independently present, and is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkylcarbonyl group having 1 to 15 carbon atoms, or a carbon number.
- R 2 represents any of an alkyl ester group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a morpholinylcarbonyl group, a phthalimide group, a piperonyl group or a hydroxyl group.
- each R 3 is independently present and is a hydrogen atom, an alkylcarbonyl group having 0 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a carbon number.
- n represents the number of carbon atoms, and represents an integer of 0, 1 or 2.
- m is the number of R 3 And satisfies the relationship 1 ⁇ m ⁇ n + 2.
- each R 4 is independently present and is any of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a hydroxyl group. Represents.
- R 5 is independently present, and is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 1 carbon atom. Represents an alkyl ester group or a hydroxyl group of ⁇ 10, and m is an integer of 1 to 10.)
- each R 6 is independently present and is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, a formyl group, an allyl group, or a carbon atom. Represents any one of the alkoxy groups of 1 to 10.
- k represents the number of R 6 and is an integer of 1 to 4.
- the epoxy resin mixture of the present invention has a cured product excellent in heat conduction, and the epoxy resin mixture has a low viscosity and excellent workability. Therefore, various composite materials including semiconductor sealing materials and prepregs, adhesives, This is useful when used in paints.
- the epoxy resin mixture of the present invention comprises the following epoxy resin (A) and further comprises a mixture containing the following liquid epoxy resin (B).
- the phenol compound (a) which is a precursor of the epoxy resin (A) will be described.
- the phenol compound (a) is obtained by a reaction between one or more compounds selected from the compounds represented by the following formulas (1) to (5) and a compound represented by the following formula (6).
- each R 1 is independently present and is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or an alkyl group having 1 to 10 carbon atoms.
- each R 1 is independently present and is preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyl group or an alkoxy group having 1 to 10 carbon atoms, particularly a hydrogen atom or carbon number 1 1-3 alkoxy groups are preferred.
- Specific examples of the compound represented by the formula (1) used for the reaction with the compound represented by the formula (6) in order to obtain the phenol compound (a) include 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2 ′, 4′-dihydroxyacetophenone, 2 ′, 5′-dihydroxyacetophenone, 3 ′, 4′-dihydroxyacetophenone, 3 ′, 5′-dihydroxyacetophenone, 2 ′, 3 ′, 4′- Trihydroxyacetophenone, 2 ′, 4 ′, 6′-trihydroxyacetophenone monohydrate, 4′-hydroxy-3′-methylacetophenone, 4′-hydroxy-2′-methylacetophenone, 2′-hydroxy-5 ′ -Methylacetophenone, 4'-hydroxy-3'-methoxyacetophenone, 2 -Hydroxy-4'-methoxyacetophenone, 4'-hydroxy-3'-nitroacetophenone, 4'-hydroxy-3 ', 5'
- each R 2 is independently present, and is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkylcarbonyl group having 1 to 15 carbon atoms, or a carbon number.
- R 2 represents any of an alkyl ester group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a morpholinylcarbonyl group, a phthalimide group, a piperonyl group or a hydroxyl group.
- Specific examples of the compound represented by the formula (2) used for the reaction with the compound represented by the formula (6) in order to obtain the phenol compound (a) include acetone, 1,3-diphenyl-2- Propanone, 2-butanone, 1-phenyl-1,3-butanedione, 2-pentanone, 3-pentanone, 4-methyl-2-pentanone, acetylacetone, 2-hexanone, 3-hexanone, isoamylmethylketone, ethylisobutylketone, 4-methyl-2-hexanone, 2,5-hexanedione, 1,6-diphenyl-1,6-hexanedione, 2-heptanone, 3-heptanone, 4-heptanone, 2-methyl-4-heptanone, 5- Methyl-3-heptanone, 6-methyl-2-heptanone, 2,6-dimethyl-4-heptanone, 2-octanone, 3-octa , 4-octanone
- each R 3 is independently present and is a hydrogen atom, an alkylcarbonyl group having 0 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a carbon number.
- n represents the number of carbon atoms, and represents an integer of 0, 1 or 2.
- m is the number of R 3 And satisfies the relationship 1 ⁇ m ⁇ n + 2.
- R 3 is an alkylcarbonyl group having 0 carbon atoms represents a carbonyl structure containing a carbon atom constituting the cycloalkane which is the main skeleton of the general formula (3)
- An example is 1,3-cyclopentanedione.
- Specific examples of the compound represented by the formula (3) used for the reaction with the compound represented by the formula (6) in order to obtain the phenol compound (a) include cyclopentanone and 3-phenylcyclopentanone.
- the solvent solubility when the obtained phenol compound is epoxidized is high, and the cured product of the epoxy resin composition exhibits high thermal conductivity. Therefore, cyclopentanone, cyclohexanone, cycloheptanone, 4- Methylcyclohexanone is preferred.
- each R 4 is independently present and is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a hydroxyl group. Represents one of these.
- Specific examples of the compound represented by the formula (4) used for the reaction with the compound represented by the formula (6) in order to obtain the phenol compound (a) include diacetyl, 2,3-pentanedione, 3 , 4-hexanedione, 5-methyl-2,3-hexanedione, 2,3-heptanedione, and the like. Of these, diacetyl is preferred because of high solvent solubility when the resulting phenol compound is epoxidized and high thermal conductivity of the cured product of the epoxy resin composition.
- R 5 is independently present, and is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 1 carbon atom. Represents an alkyl ester group of ⁇ 10 or a hydroxyl group, and m is an integer of 1-10.
- each R 5 is independently present, and is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a hydroxyl group.
- Specific examples of the compound represented by the formula (5) used for the reaction with the compound represented by the formula (6) in order to obtain the phenol compound (a) include ethyl diacetate and 2,5-hexanedione. 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, 3-butyl-2,4-pentanedione, 3-phenyl-2,4-pentanedione, 4-acetyl-5 -Ethyl oxohexanoate and the like.
- 3-methyl-2,4-pentanedione, 3-methyl-2,4-pentanedione, 3) is highly soluble in solvent when the resulting phenol compound is epoxidized, and the cured product of the epoxy resin composition exhibits high thermal conductivity.
- -Ethyl-2,4-pentanedione is preferred.
- each R 6 is independently present and is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, a formyl group, an allyl group, or a carbon atom.
- k represents the number of R 6 and is an integer of 0 to 4.
- R 6 is independently present and is preferably an alkoxy group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by the formula (6) used in the reaction with one or more selected from the compounds represented by the formulas (1) to (5) to obtain the phenol compound (a) include: For example, 2-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, syringaldehyde, 3 , 5-di-tert-butyl-4-hydroxybenzaldehyde, isovanillin, 4-hydroxy-3-nitrobenzaldehyde, 5-hydroxy-2-nitrobenzaldehyde, 3,4-dihydroxy-5-nitrobenzaldehyde, vanillin, o-vanillin , 2-hi Droxy-1-naphthaldehyde, 2-hydroxy-5-nitro-m-anisaldehyde, 2-hydroxy-5-methyliso
- the phenol compound (a) is an aldol condensation reaction between one or more compounds selected from the compounds represented by the formulas (1) to (5) and the compound represented by the formula (6) under acidic conditions or basic conditions. Obtained by etc.
- the compound represented by the formula (6) is 1.0 to 1.05 mol per 1 mol of the compound represented by the formula (1), the formula (2), the formula (3), the formula (4) and the formula It is preferable to use 2.0 to 3.15 mol with respect to 1 mol of the compound represented by (5).
- examples of the acidic catalyst that can be used include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, and organic acids such as toluenesulfonic acid, xylenesulfonic acid, and oxalic acid. These may be used alone or in combination of a plurality of types.
- the amount of the acidic catalyst to be used is generally 0.01 to 1.0 mol, preferably 0.2 to 0.5 mol, per 1 mol of the compound represented by the formula (6).
- usable basic catalysts include metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as potassium carbonate and sodium carbonate, diethylamine, Examples include amine derivatives such as triethylamine, tributylamine, diisobutylamine, pyridine and piperidine, and amino alcohol derivatives such as dimethylaminoethyl alcohol and diethylaminoethyl alcohol. Also in the case of basic conditions, the basic catalysts listed above may be used alone, or a plurality of types may be used in combination. The amount of the basic catalyst to be used is generally 0.1 to 2.5 mol, preferably 0.2 to 2.0 mol, per 1 mol of the compound represented by the formula (6).
- a solvent may be used as necessary.
- the solvent that can be used is not particularly limited as long as it does not have reactivity with the compound represented by the formula (6) such as ketones, but the compound represented by the formula (6) as a raw material can be easily used. It is preferable to use alcohols as the solvent in terms of dissolution in the solvent.
- the reaction temperature is usually 10 to 90 ° C., preferably 35 to 70 ° C.
- the reaction time is usually 0.5 to 10 hours, but is not limited to this because the reactivity varies depending on the type of raw material compound.
- an unreacted substance, a solvent, etc. are removed from a reaction liquid under heating and pressure reduction, after washing
- crystallization a crystal
- the produced phenol compound (a) may dissolve in water, so that it is precipitated as crystals under neutral to acidic conditions by adding hydrochloric acid or the like.
- the epoxy compound (A) of the phenol compound exhibits excellent solvent solubility, and a cured product having high thermal conductivity can be obtained.
- the phenol compound (a) obtained by reaction with the compound represented by Formula (3) is preferable.
- the phenol compound (b) that is a precursor of the liquid epoxy resin (B) will be described.
- the phenol compound (b) if the epoxy resin obtained by reacting with epihalohydrin is liquid at room temperature (25 ° C.), it can be used without any problem, but the viscosity of the resulting epoxy resin is The measured value with an E-type viscometer at room temperature (25 ° C.) is preferably 20 Pa ⁇ s or less, and it is preferable to use one having a viscosity of 5.0 Pa ⁇ s or less.
- Specific examples of such a phenol compound (b) include, for example, bisphenol A, bisphenol F, resorcin novolac, and dihydroxynaphthalene.
- a liquid epoxy resin shows a liquid epoxy resin at room temperature (25 degreeC).
- the epoxy resins (A) and (B) can be obtained by reacting the phenol compound (a), the phenol compound (b) and the epihalohydrin obtained by the above method and epoxidizing them.
- the phenol compound (a) and the phenol compound (b) may be mixed after epoxidation, or the phenol compound (a) and the phenol compound (b) are mixed in advance before epoxidation. May be.
- any phenol compound that is usually used as a raw material for the epoxy resin can be used without particular limitation, but the cured product has a high thermal conductivity. It is preferable that the amount of the phenol compound that can be used in combination is as small as possible, since the effect of the present invention that it has excellent workability of the epoxy resin mixture may be impaired.
- the sum of the amount of the phenol compound (a) in the total amount of the phenol compounds (a) and (b) is 1 to 50 mass. %, More preferably 10 to 50% by mass. If the proportion of the amount of the phenol compound (a) is small, the thermal conductivity of the cured product may be low, and if the proportion is large, the viscosity may be high.
- the epoxidation procedure is the same even when epoxidizing each of the phenolic compound (a) and the phenolic compound (b) or when epoxidizing the phenolic compound (a) and the phenolic compound (b) in advance. Can be done.
- epichlorohydrin, ⁇ -methylepichlorohydrin, ⁇ -methylepichlorohydrin, epibromohydrin, etc. can be used as the epihalohydrin, but epichlorohydrin is easily available industrially. Is preferred.
- the amount of epihalohydrin used is usually 2 to 20 mol, preferably 2 to 15 mol, particularly preferably 2 to 6.5 mol, per 1 mol of the hydroxyl group of the phenol compound.
- the epoxy resin can be obtained by a reaction in which a phenol compound and an epihalohydrin are added in the presence of an alkali metal oxide, and then the resulting 1,2-halohydrin ether group is cyclized to epoxidize.
- epihalohydrin in an amount significantly smaller than usual as described above, the molecular weight of the epoxy resin can be increased and the molecular weight distribution can be broadened.
- the resulting epoxy resin can be removed from the system as a resinous material having a relatively low softening point, and exhibits excellent solvent solubility.
- Examples of the alkali metal hydroxide that can be used for the epoxidation reaction include sodium hydroxide, potassium hydroxide, and the like, and these may be used as they are, or an aqueous solution thereof may be used.
- an aqueous solution the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system and separated from a mixture of water and epihalohydrin distilled continuously under reduced pressure or normal pressure. Alternatively, water may be removed and only the epihalohydrin is continuously returned to the reaction system.
- the amount of the alkali metal hydroxide used is usually 0.9 to 3.0 mol, preferably 1.0 to 2.5 mol, more preferably 1.0 to 2.0 mol per mol of the hydroxyl group of the phenol compound.
- the present inventors remarkably reduce the amount of halogen contained in the epoxy resin obtained by using flaky sodium hydroxide in the epoxidation reaction, rather than using sodium hydroxide as an aqueous solution. It came to know that it became possible.
- This halogen is derived from epihalohydrin, and the more it is mixed in the epoxy resin, the lower the thermal conductivity of the cured product.
- the flaky sodium hydroxide is preferably added in portions in the reaction system. By carrying out divided addition, it is possible to prevent a rapid decrease in the reaction temperature, thereby preventing the formation of impurities such as 1,3-halohydrin and halomethylene, and a cured product with higher thermal conductivity. Can be formed.
- a quaternary ammonium salt such as tetramethylammonium chloride, tetramethylammonium bromide, trimethylbenzylammonium chloride as a catalyst.
- the amount of the quaternary ammonium salt used is usually 0.1 to 15 g, preferably 0.2 to 10 g, per 1 mol of the hydroxyl group of the phenol compound.
- an alcohol such as methanol, ethanol or isopropyl alcohol, or an aprotic polar solvent such as dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran or dioxane.
- alcohols or dimethyl sulfoxide are preferable.
- an epoxy resin can be obtained with a high yield.
- dimethyl sulfoxide is used, the halogen content in the epoxy resin can be further reduced.
- the amount used is usually 2 to 50% by mass, preferably 4 to 35% by mass, based on the amount of epihalohydrin used.
- an aprotic polar solvent is used, it is usually 5 to 100% by mass, preferably 10 to 80% by mass, based on the amount of epihalohydrin used.
- the reaction temperature is usually 30 to 90 ° C, preferably 35 to 80 ° C.
- the reaction time is usually 0.5 to 10 hours, preferably 1 to 8 hours.
- the reaction product is washed with water or without washing with water, and the epihalohydrin, the solvent and the like are removed from the reaction solution under heating and reduced pressure.
- the recovered epoxy resin is dissolved in a solvent such as toluene or methyl isobutyl ketone, and an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is obtained.
- the reaction can be carried out by adding an aqueous solution of to ensure ring closure.
- the amount of alkali metal hydroxide used is usually 0.01 to 0.3 mol, preferably 0.05 to 0.2 mol, per mol of the hydroxyl group of the phenol compound.
- the reaction temperature is usually 50 to 120 ° C., and the reaction time is usually 0.5 to 2 hours.
- the produced salt is removed by filtration, washing with water, etc., and the solvent is distilled off under heating and reduced pressure to obtain an epoxy resin.
- an epoxy resin precipitates as a crystal
- generated in a lot of water you may filter the crystal
- the amount of the epoxy resin (A) in the total amount of the epoxy resin is preferably 1 to 50% by mass, more preferably 10 to 50% by mass. If the proportion of the amount of the epoxy resin (A) is small, the thermal conductivity of the cured product may be low, and if the proportion is large, the viscosity of the epoxy resin mixture may be high.
- the epoxy resin (A) the epoxy equivalent is 350 g / eq. The following are preferred, especially 300 g / eq. The following is preferred.
- the epoxy equivalent is usually 163 g / eq. ⁇ 210 g / eq. 163 g / eq. ⁇ 200 g / eq.
- the value measured with the E-type viscosity meter at room temperature (25 degreeC) is 20 Pa * s or less normally, 15 Pa * s or less is more preferable, and 5.0 Pa * s or less is preferable. Further preferred.
- the amount of the epoxy resin (B) in the total amount of the epoxy resin is preferably 50 to 99% by mass, more preferably 50 to 90% by mass.
- the mixture of each epoxy resin which has said preferable epoxy equivalent is a preferable aspect as this invention.
- the epoxy resin mixture thus obtained has low viscosity and excellent workability, the cured product has high thermal conductivity, and the epoxy resin mixture of the present invention has a low melting point compared to an epoxy resin having a mesogenic group. Furthermore, since it has excellent solvent solubility, a uniform cured product can be obtained.
- the epoxy resin composition of the present invention contains the epoxy resin mixture of the present invention as an essential component.
- the epoxy resin mixture of the present invention can be used alone or in combination with other epoxy resins.
- epoxy resins include bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, bisphenol I, etc.) and phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted) Naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene and dihydroxynaphthalene) and various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.) Of polycondensates with benzene, aromatic compounds such as xylene and formaldehy
- the ratio of the epoxy resin mixture of the present invention to the total epoxy resin components in the epoxy resin composition of the present invention is 30 mass% or more is preferable, 40 mass% or more is more preferable, 70 mass% or more is still more preferable, Especially preferably, it is 100 mass% (when other epoxy resins are not used together).
- the epoxy resin composition of the present invention it is most preferable to use 100% by mass of the epoxy resin mixture of the present invention as an epoxy resin.
- Examples of the curing agent contained in the epoxy resin composition of the present invention include amine compounds, acid anhydride compounds, amide compounds, and phenol compounds. Specific examples of these and other curing agents are shown in the following (a) to (e).
- Phenol compounds Polyhydric phenols (bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, terpene diphenol, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 3,3 ', 5, 5′-tetramethyl- (1,1′-biphenyl) -4,4′-diol, hydroquinone, resorcin, naphthalenediol, tris- (4-hydroxyphenyl) methane and 1,1,2,2-tetrakis (4 -Hydroxyphenyl) ethane and the like; phenols (eg, phenol, alkyl-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene and dihydroxynaphthalene) and aldehydes (formaldehyde, acetaldehyde, benzaldehyde, p-
- active hydrogen groups such as amine compounds such as diaminodiphenylmethane, diaminodiphenylsulfone and naphthalenediamine, and condensates of catechol and aldehydes, ketones, dienes, substituted biphenyls or substituted phenyls.
- curing agent may be used independently and may use multiple.
- the total amount of the curing agent used is preferably 0.5 to 2.0 equivalents, particularly preferably 0.6 to 1.5 equivalents, based on 1 equivalent of the epoxy groups of all epoxy resins.
- the epoxy resin composition of the present invention can impart further excellent high heat conductivity to the cured product by containing an inorganic filler excellent in heat conduction as required.
- the inorganic filler contained in the epoxy resin composition of the present invention is added for the purpose of imparting higher thermal conductivity to the cured product of the epoxy resin composition, and the thermal conductivity of the inorganic filler itself is too low. In some cases, the high thermal conductivity obtained by the combination of the epoxy resin and the curing agent may be impaired. Therefore, as the inorganic filler contained in the epoxy resin composition of the present invention, the one having higher thermal conductivity is preferable, usually 20 W / m ⁇ K or more, preferably 30 W / m ⁇ K or more, more preferably 50 W / m.
- inorganic fillers having such characteristics include inorganic powder fillers such as boron nitride, aluminum nitride, silicon nitride, silicon carbide, titanium nitride, zinc oxide, tungsten carbide, alumina, magnesium oxide, synthetic fibers, Examples thereof include fibrous fillers such as ceramic fibers, and coloring agents.
- the shape of these inorganic fillers may be any of powder (bulk shape, spherical shape), single fiber, long fiber, etc.
- the cured product is cured by the lamination effect of the inorganic filler itself.
- the amount of the inorganic filler used in the epoxy resin composition of the present invention is usually 2 to 1000 parts by mass with respect to 100 parts by mass of the resin component in the epoxy resin composition, but in order to increase the thermal conductivity as much as possible. It is preferable to increase the amount of the inorganic filler as much as possible as long as the handling of the epoxy resin composition of the present invention in a specific application is not hindered.
- These inorganic fillers may be used alone or in combination of two or more.
- the thermal conductivity of the entire filler can be maintained at 20 W / m ⁇ K or more, the thermal conductivity of the inorganic filler with 20 W / m ⁇ K or more is less than 20 W / m ⁇ K.
- the use of a filler having a thermal conductivity of less than 20 W / m ⁇ K is minimal. Should be kept on.
- the epoxy resin composition of the present invention When the epoxy resin composition of the present invention is used for semiconductor encapsulation, heat conduction is performed at a ratio of 75 to 93% by mass in the epoxy resin composition from the viewpoint of heat resistance, moisture resistance, mechanical properties, etc. of the cured product. It is preferable to use an inorganic filler having a rate of 20 W / m ⁇ K or more.
- the balance is an epoxy resin component, a curing agent component, and other additives that are added as necessary. Examples of the additive include other inorganic fillers that can be used in combination and a curing accelerator that will be described later.
- the epoxy resin composition of the present invention may contain a curing accelerator.
- the curing accelerator that can be used include imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole and 2-ethyl-4-methylimidazole, 2- (dimethylaminomethyl) phenol, triethylenediamine, Tertiary amines such as triethanolamine and 1,8-diazabicyclo (5,4,0) undecene-7, organic phosphines such as triphenylphosphine, diphenylphosphine and tributylphosphine, metal compounds such as tin octylate, Tetrasubstituted phosphonium tetrasubstituted borates such as tetraphenylphosphonium tetraphenylborate and tetraphenylphosphonium ethyltriphenylborate, 2-ethyl-4-methylimidazole
- thermosetting resins and thermoplastic resins include vinyl ester resins, unsaturated polyester resins, maleimide resins, cyanate resins, isocyanate compounds, benzoxazine compounds, vinyl benzyl ether compounds, polybutadiene and its modified products, and acrylonitrile.
- thermosetting resin or thermoplastic resin is used in an amount occupying 60% by mass or less in the epoxy resin composition of the present invention.
- the epoxy resin composition of the present invention can be obtained by uniformly mixing the above-mentioned components, and preferred applications thereof include semiconductor encapsulants and printed wiring boards.
- the epoxy resin composition of the present invention can be easily made into a cured product by the same method as conventionally known.
- an epoxy resin mixture which is an essential component of the epoxy resin composition of the present invention, a curing agent, an inorganic filler having a thermal conductivity of 20 W / m ⁇ K or more, and if necessary, a curing accelerator, a compounding agent, various thermosetting properties
- the epoxy resin composition of the present invention obtained by thoroughly mixing a resin, various thermoplastic resins, etc., as necessary, using an extruder, a kneader, or a roll, until it becomes uniform can be obtained by a melt casting method or a transfer method.
- a cured product of the epoxy resin composition of the present invention can be obtained by molding by a molding method, an injection molding method, a compression molding method, or the like, and further heating for 2 to 10 hours above the melting point.
- the epoxy resin composition of the present invention can be used for semiconductor sealing applications.
- the epoxy resin composition of this invention can also be made into the varnish containing a solvent.
- the varnish includes, for example, at least the epoxy resin mixture of the present invention, and optionally includes a mixture containing other components such as an inorganic filler having a thermal conductivity of 20 W / m ⁇ K or more, toluene, xylene, acetone, Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, N, N′-dimethylformamide, N, N′-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dimethyl ether, Glycol ethers such as dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, ethyl acetate, but
- the amount of the solvent is usually 10 to 95% by mass, preferably 15 to 85% by mass, based on the entire varnish.
- the varnish obtained as described above is impregnated into a fiber substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber and paper, and then the solvent is removed by heating, and the epoxy resin composition of the present invention By making a semi-cured state, the prepreg of the present invention can be obtained.
- the “semi-cured state” means a state in which an epoxy group which is a reactive functional group partially remains unreacted.
- the prepreg can be hot press molded to obtain a cured product.
- Synthesis example 1 A flask equipped with a stirrer, a reflux condenser, and a stirrer was charged with 136 parts of 4′-hydroxyacetophenone, 152 parts of vanillin and 200 parts of ethanol and dissolved. After adding 20 parts of 97 mass% sulfuric acid to this, it heated up to 60 degreeC, and after reacting at this temperature for 10 hours, the reaction liquid was inject
- Synthesis example 2 In a flask equipped with a stirrer, a reflux condenser, and a stirrer, 166 parts of 4′-hydroxy-3′-methoxyacetophenone, 122 parts of 4-hydroxybenzaldehyde and 200 parts of ethanol were charged and dissolved. After adding 20 parts of 97% sulfuric acid thereto, the temperature was raised to 50 ° C., and after reacting at this temperature for 10 hours, the reaction solution was poured into 1200 parts of water for crystallization. The crystals were separated by filtration, washed twice with 600 parts of water, and then vacuum-dried to obtain 285 parts of phenol compound 2 as brown crystals. The endothermic peak temperature of the obtained crystal as measured by DSC was 193 ° C.
- Synthesis example 3 A flask equipped with a stirrer, a reflux condenser, and a stirrer was charged with 56 parts of 4-methylcyclohexanone, 152 parts of vanillin and 150 parts of ethanol and dissolved. After adding 10 parts of 97 mass% sulfuric acid, the temperature was raised to 50 ° C., and after reacting at this temperature for 10 hours, 25 parts of sodium tripolyphosphate was added and stirred for 30 minutes. Thereafter, 500 parts of methyl isobutyl ketone was added, followed by washing twice with 200 parts of water, and then the solvent was distilled off with an evaporator to obtain 304 parts of semi-solid phenol compound 3.
- Synthesis example 4 A flask equipped with a stirrer, a reflux condenser, and a stirrer was charged with 29 parts of acetone, 152 parts of vanillin and 300 parts of ethanol and dissolved. After adding 80 parts of 50% aqueous sodium hydroxide solution to this, the temperature was raised to 45 ° C., and after reacting at this temperature for 120 hours, the reaction solution was poured into 800 mL of 1.5N hydrochloric acid for crystallization. The crystals were separated by filtration, washed twice with 600 parts of water, and then vacuum-dried to obtain 165 parts of phenol compound 4 as yellow crystals. The melting point of the obtained crystal was 201 ° C. by DSC measurement.
- Synthesis example 5 While purging a flask equipped with a stirrer, a reflux condenser, and a stirrer with nitrogen purge, 135 parts of the phenol compound 1 obtained in Synthesis Example 1, 370 parts of epichlorohydrin, and 93 parts of dimethyl sulfoxide (hereinafter, DMSO) were added, Under stirring, the temperature was raised to 70 ° C., and the mixture was dissolved. After 41 parts of flaky sodium hydroxide were added in portions over 90 minutes, the reaction was allowed to proceed at 70 ° C. for 2.5 hours. After completion of the reaction, excess solvent such as epichlorohydrin was distilled off under reduced pressure at 135 ° C. using a rotary evaporator.
- DMSO dimethyl sulfoxide
- the residue was dissolved in 440 parts of methyl isobutyl ketone (hereinafter referred to as MIBK) and then washed with water to remove the salt. After washing with water, the MIBK solution was heated to 70 ° C., and 11 parts of a 30% aqueous sodium hydroxide solution was added with stirring. After reacting for 1 hour, washing was carried out until the washing water became neutral. 200 parts of epoxy resin 1 was obtained by distilling MIBK etc. off under reduced pressure at 180 degreeC using the rotary evaporator. The epoxy equivalent of the obtained epoxy resin is 240 g / eq. The softening point was 56 ° C.
- MIBK methyl isobutyl ketone
- Synthesis Example 6 While purging a flask equipped with a stirrer, a reflux condenser, and a stirrer with nitrogen purge, 135 parts of the phenol compound 2 obtained in Synthesis Example 2, 370 parts of epichlorohydrin, and 93 parts of dimethyl sulfoxide (hereinafter, DMSO) were added. Under stirring, the temperature was raised to 70 ° C., and the mixture was dissolved. After 41 parts of flaky sodium hydroxide were added in portions over 90 minutes, the reaction was allowed to proceed at 70 ° C. for 2.5 hours. After completion of the reaction, excess solvent such as epichlorohydrin was distilled off under reduced pressure at 135 ° C. using a rotary evaporator.
- DMSO dimethyl sulfoxide
- the residue was dissolved in 440 parts of MIBK and then washed with water to remove the salt. After washing with water, the MIBK solution was heated to 70 ° C., and 11 parts of a 30% aqueous sodium hydroxide solution was added with stirring. After reacting for 1 hour, washing was carried out until the washing water became neutral. 201 parts of epoxy resin 2 was obtained by distilling MIBK etc. off under reduced pressure at 180 degreeC using the rotary evaporator. The epoxy equivalent of the obtained epoxy resin is 243 g / eq. The softening point was 60 ° C.
- Synthesis example 7 While purging a flask equipped with a stirrer, a reflux condenser, and a stirrer with nitrogen purge, 190 parts of the phenol compound 3 obtained in Synthesis Example 3, 370 parts of epichlorohydrin, and 93 parts of dimethyl sulfoxide (hereinafter, DMSO) were added. Under stirring, the temperature was raised to 70 ° C., and the mixture was dissolved. After 41 parts of flaky sodium hydroxide were added in portions over 90 minutes, the reaction was allowed to proceed at 70 ° C. for 2.5 hours. After completion of the reaction, excess solvent such as epichlorohydrin was distilled off under reduced pressure at 135 ° C. using a rotary evaporator.
- DMSO dimethyl sulfoxide
- the residue was dissolved in 492 parts of MIBK and then washed with water to remove the salt. After washing with water, the MIBK solution was heated to 70 ° C., and 11 parts of a 30% aqueous sodium hydroxide solution was added with stirring. After reacting for 1 hour, washing was carried out until the washing water became neutral. 224 parts of epoxy resin 3 was obtained by distilling MIBK etc. off under reduced pressure at 180 degreeC using the rotary evaporator. The epoxy equivalent of the obtained epoxy resin is 270 g / eq. The softening point was 62 ° C.
- Synthesis example 8 While purging a flask equipped with a stirrer, a reflux condenser, and a stirrer with nitrogen purge, 163 parts of the phenol compound 4 obtained in Synthesis Example 4, 370 parts of epichlorohydrin, 93 parts of dimethyl sulfoxide (hereinafter, DMSO) were added, Under stirring, the temperature was raised to 70 ° C., and the mixture was dissolved. After 41 parts of flaky sodium hydroxide were added in portions over 90 minutes, the reaction was allowed to proceed at 70 ° C. for 2.5 hours. After completion of the reaction, excess solvent such as epichlorohydrin was distilled off under reduced pressure at 135 ° C. using a rotary evaporator.
- DMSO dimethyl sulfoxide
- the residue was dissolved in 438 parts of MIBK and then washed with water to remove the salt. After washing with water, the MIBK solution was heated to 70 ° C., and 11 parts of a 30% aqueous sodium hydroxide solution was added with stirring. After reacting for 1 hour, washing was carried out until the washing water became neutral. 200 parts of epoxy resin 4 was obtained by distilling MIBK etc. off under reduced pressure at 180 degreeC using the rotary evaporator. The epoxy equivalent of the obtained epoxy resin is 240 g / eq. The softening point was 52 ° C.
- Epoxy resins 1 to 4 obtained in the synthesis example were put in flasks, heated and melted in an oil bath, and epoxy resins 5 and 6 were blended in the proportions (parts) shown in Table 1 to obtain EP mixture 1 ⁇ 8 were obtained. The results of measuring these viscosities are shown in Table 1.
- Epoxy resin 5 bisphenol A type epoxy resin (trade name: RE-410S, Nippon Kayaku Epoxy equivalent 185 g / eq.)
- Epoxy resin 6 bisphenol F type epoxy resin (trade name: jER806L, manufactured by Mitsubishi Chemical, epoxy equivalent of 165 g / eq.)
- Examples 9-24 In addition to the EP mixtures 1 to 8 obtained in Examples 1 to 8, various components were blended in the proportions (parts) shown in Table 2, and then poured into a mold, and heated at 160 ° C. for 2 hours and further at 180 ° C. for 8 hours. The cured product of the epoxy resin composition of the present invention and the comparative resin composition was obtained. The results of measuring the thermal conductivity of these cured products are shown in Table 2.
- Curing agent 1 Acid anhydride curing agent (trade name: Kayahard MCD Nippon Kayaku Co., Ltd., viscosity 0.25 Pa ⁇ s)
- Curing agent 2 Aromatic amine-based curing agent (trade name: Kayahard AA Nippon Kayaku Co., Ltd., viscosity 2.5 Pa ⁇ s)
- Curing accelerator 2E4MZ (manufactured by Shikoku Chemicals)
- the cured product of the epoxy resin composition containing the epoxy resin mixture of the present invention has excellent thermal conductivity. Moreover, it was confirmed that the viscosity of the epoxy resin mixture of the present invention is extremely low. Therefore, the epoxy resin mixture of the present invention is extremely useful when used for insulating materials for electric / electronic parts, laminated boards (printed wiring boards, etc.) and the like.
- the cured product of the epoxy resin mixture of the present invention has excellent thermal conductivity as compared with the cured product of the conventional epoxy resin, and the epoxy resin mixture is liquid and has a low viscosity and excellent workability. Therefore, it is extremely useful for a wide range of applications such as an electric / electronic material, a molding material, a casting material, a laminated material, a paint, an adhesive, a resist, and an optical material as a sealing material and a prepreg.
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Abstract
La présente invention concerne un mélange de résines époxy pouvant être polymérisé pour donner un article polymérisé présentant une grande conductivité thermique, une faible viscosité et une remarquable aptitude au façonnage. Ledit mélange de résines époxy comprend une résine époxy (A) qui résulte de la réaction d'une épihalohydrine avec un composé phénolique (a), produit par réaction d'un composé représenté par la formule (1), ou équivalent, avec un composé représenté par la formule (6) ; et une résine époxy liquide (B).
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CN201280058051.9A CN103987752A (zh) | 2011-11-25 | 2012-11-21 | 环氧树脂混合物、环氧树脂组合物、预浸料及它们的固化物 |
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WO2016175001A1 (fr) * | 2015-04-30 | 2016-11-03 | 信越化学工業株式会社 | Composition de graisse de silicone thermoconductrice |
CN114516787A (zh) * | 2020-11-20 | 2022-05-20 | 信越化学工业株式会社 | 酚化合物、导电性糊剂组成物、导电性糊剂组成物的制造方法、导电配线及其制造方法 |
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TWI702204B (zh) * | 2016-02-03 | 2020-08-21 | 日商田岡化學工業股份有限公司 | 具有茀骨架的雙酚類、其製造方法,以及衍生自該雙酚類之聚芳酯樹脂、(甲基)丙烯酸酯化合物及環氧樹脂 |
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2012
- 2012-11-21 WO PCT/JP2012/080153 patent/WO2013077351A1/fr active Application Filing
- 2012-11-21 KR KR1020147013809A patent/KR101931117B1/ko active IP Right Grant
- 2012-11-21 CN CN201280058051.9A patent/CN103987752A/zh active Pending
- 2012-11-23 TW TW101143836A patent/TW201339193A/zh unknown
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JP2011132368A (ja) * | 2009-12-24 | 2011-07-07 | Sekisui Chem Co Ltd | 樹脂組成物及び積層構造体 |
WO2011093474A1 (fr) * | 2010-01-29 | 2011-08-04 | 日本化薬株式会社 | Composé phénolique, résine époxyde, composition de résine époxyde, préimprégné, et leur produit durci |
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WO2016175001A1 (fr) * | 2015-04-30 | 2016-11-03 | 信越化学工業株式会社 | Composition de graisse de silicone thermoconductrice |
JPWO2016175001A1 (ja) * | 2015-04-30 | 2017-08-31 | 信越化学工業株式会社 | 熱伝導性シリコーングリース組成物 |
US10704008B2 (en) | 2015-04-30 | 2020-07-07 | Shin-Etsu Chemical Co., Ltd. | Heat-conductive silicone grease composition |
CN114516787A (zh) * | 2020-11-20 | 2022-05-20 | 信越化学工业株式会社 | 酚化合物、导电性糊剂组成物、导电性糊剂组成物的制造方法、导电配线及其制造方法 |
Also Published As
Publication number | Publication date |
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CN103987752A (zh) | 2014-08-13 |
KR20140103921A (ko) | 2014-08-27 |
JP5840470B2 (ja) | 2016-01-06 |
JP2013112694A (ja) | 2013-06-10 |
KR101931117B1 (ko) | 2018-12-20 |
TW201339193A (zh) | 2013-10-01 |
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