TWI522340B - Phenol compounds, epoxy resins, epoxy resin compositions, prepregs and the like - Google Patents
Phenol compounds, epoxy resins, epoxy resin compositions, prepregs and the like Download PDFInfo
- Publication number
- TWI522340B TWI522340B TW100103607A TW100103607A TWI522340B TW I522340 B TWI522340 B TW I522340B TW 100103607 A TW100103607 A TW 100103607A TW 100103607 A TW100103607 A TW 100103607A TW I522340 B TWI522340 B TW I522340B
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- Prior art keywords
- group
- substituted
- epoxy resin
- carbon atoms
- unsubstituted
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 173
- 229920000647 polyepoxide Polymers 0.000 title claims description 173
- 239000000203 mixture Substances 0.000 title claims description 78
- 150000002989 phenols Chemical class 0.000 title claims description 18
- 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 title description 7
- -1 morpholinylcarbonyl group Chemical group 0.000 claims description 96
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000011256 inorganic filler Substances 0.000 claims description 24
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 17
- 125000005907 alkyl ester group Chemical group 0.000 claims description 10
- 239000002861 polymer material Substances 0.000 claims description 9
- 239000004065 semiconductor Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 241000208818 Helianthus Species 0.000 claims description 6
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 6
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 claims description 6
- 229950000188 halopropane Drugs 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 150000004060 quinone imines Chemical group 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 92
- 239000000047 product Substances 0.000 description 41
- 239000002904 solvent Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 26
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- 239000004848 polyfunctional curative Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 238000006735 epoxidation reaction Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 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 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-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
- 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
- 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 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 230000002378 acidificating effect Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 238000001721 transfer moulding Methods 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
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 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
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LTMXHUUHBSCKEK-UHFFFAOYSA-N Hexadecan-3-one Chemical compound CCCCCCCCCCCCCC(=O)CC LTMXHUUHBSCKEK-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920003986 novolac Polymers 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
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 150000003839 salts Chemical class 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 description 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-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
- 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
- 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
- GUARKOVVHJSMRW-UHFFFAOYSA-N 3-ethylpentane-2,4-dione Chemical compound CCC(C(C)=O)C(C)=O GUARKOVVHJSMRW-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
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-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
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
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- 230000007257 malfunction Effects 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 150000004692 metal hydroxides Chemical class 0.000 description 1
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- 229920002647 polyamide Polymers 0.000 description 1
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- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000004151 quinonyl group Chemical group 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 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
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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Description
本發明係關於一種新穎之酚化合物、環氧樹脂及環氧樹脂組成物。另外係關於一種藉由該環氧樹脂組成物而形成之預浸體等之硬化物。
環氧樹脂組成物通常製成機械性質、耐水性、耐化學品性、耐熱性、電氣性質等優異之硬化物而用於接著劑、塗料、積層板、成形材料、澆鑄材料等廣泛之領域。近年來,對用於該等領域之環氧樹脂之硬化物謀求進而提昇以高純度化為代表之難燃性、耐熱性、耐濕性、強韌性、低線膨脹率、低介電率特性等各種特性。
尤其於作為環氧樹脂組成物之代表性之用途的電氣、電子產業領域,正在發展以多功能化、高性能化、小型化為目的之半導體之高密度構裝或印刷配線板之高密度配線化,但隨著高密度構裝化或高密度配線化,自半導體元件或印刷配線板之內部產生之熱量增加,從而可成為引起故障之原因。因此,就能量效率或機器設計方面而言,如何使所產生之熱量有效地釋放至外部亦成為重要之課題。該等熱對策,存在使用金屬芯基板、或於設計之階段組合易放熱之構造或於所使用之高分子材料(環氧樹脂)緻密地填充高導熱填料等各種方法。然而,當前由於接合高導熱部位之用於黏合劑的高分子材料之導熱率較低,故而限制了高分子材料之導熱速度,無法有效地放熱。
專利文獻1中報告有於構造中導入液晶性基(Mesogenic group)來作為實現環氧樹脂之高導熱化的方法,且記載有具有聯苯骨架之環氧樹脂等來作為具有液晶性基之環氧樹脂。另外,記載有苯甲酸苯酯型環氧樹脂來作為除聯苯骨架以外之環氧樹脂,但該環氧樹脂需要藉由利用氧化之環氧化反應而製造,因此於安全性或成本方面有困難,認為不實用。使用具有聯苯骨架之環氧樹脂之例,可列舉專利文獻2~4,其中專利文獻3中記載有併用具有高導熱率之無機填充材料之方法。然而,藉由該等文獻所記載之方法而獲得之硬化物之導熱性並非滿足市場要求之水平,謀求使用可相對廉價地獲得之環氧樹脂且提供具有更高導熱率之硬化物的環氧樹脂組成物。
另外,迄今為止所報告之具有液晶性基之高導熱性環氧樹脂大多熔點非常高而以樹脂狀取出較為困難,並且溶劑可溶性差。上述環氧樹脂於進行硬化時,在完全熔融之前開始硬化,故而難以製作均勻之硬化物,認為不佳。
進而,認為與環氧樹脂同樣,環氧樹脂組成物所含之硬化劑亦為實現高導熱化之重要因素。先前,作為強調其硬化物具有高導熱率之環氧樹脂組成物所含之硬化劑,專利文獻1中記載有4,4'一苯甲酸二胺基二苯酯、4,4'-二胺基二苯甲烷,專利文獻2及3中記載有使用1,5-萘二胺等胺系硬化劑之例。然而,由於該等胺系硬化劑具有硬化促進作用,故而難以確保製作硬化物時之壽命,認為不佳。於專利文獻4中,作為將酚化合物用作硬化劑之例,使用鄰苯二酚酚醛清漆,藉由該文獻所記載之方法而獲得之硬化物之導熱性亦並非滿足市場要求之水平,期望開發提供具有更高導熱率之硬化物之環氧樹脂組成物。
[專利文獻1]日本特開平11-323162號公報
[專利文獻2]日本特開2004-2573號公報
[專利文獻3]日本特開2006-63315號公報
[專利文獻4]日本特開2003-137971號公報
本發明係為解決上述問題進行研究之結果而成,提供一種其硬化物具有高導熱性且溶劑可溶性優異之環氧樹脂及作為其前驅物之酚化合物。
本發明人等為解決上述課題進行潛心研究,結果完成本發明。
即,本發明係關於如下所述。
(1)一種酚化合物,其係藉由下述式(1)~(5)所示之化合物之一種以上與下述式(6)所示之化合物進行反應而獲得:
(式(1)中,R1分別獨立存在,表示氫原子、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、羥基、硝基、或碳數1~10之經取代或未經取代之烷氧基中之任一者,1表示R1數,為0~4之整數)
(式(2)中,R2分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~15之經取代或未經取代之烷羰基(alkylcarbonyl)、碳數2~10之經取代或未經取代之烷基酯基、碳數1~10之經取代或未經取代之烷氧基、嗎啉基羰基(morpholinylcarbonyl)、酞醯亞胺基、向日葵基、或羥基中之任一者)
(式(3)中,R3分別獨立存在,表示氫原子、碳數0~10之經取代或未經取代之烷羰基、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數2~10之經取代或未經取代之烷基酯基、碳數1~10之經取代或未經取代之烷氧基、或羥基中之任一者,n表示碳數,表示0、1、2之任一整數,m表示R3數,滿足0≦m≦n+2之關係)
(式(4)中,R12分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~10之經取代或未經取代之烷氧基、或羥基中之任一者)
(式(5)中,R13分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~10之經取代或未經取代之烷氧基、碳數1~10之經取代或未經取代之烷基酯基、或羥基中之任一者;另外m為1~10之整數)
(式(6)中,R4分別獨立存在,表示氫原子、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、羥基、硝基、甲醯基、烯丙基、或碳數1~10之經取代或未經取代之烷氧基中之任一者,k表示R4數,為0~4之整數)。
(2)一種環氧樹脂,其係使環氧鹵丙烷(epihalohydrin)與如前項(1)之酚化合物進行反應而獲得。
(3)如前項(2)之環氧樹脂,其中,總鹵素量為1800ppm以下。
(4)一種環氧樹脂組成物,其係含有前項(2)或(3)之環氧樹脂、前項(1)之酚化合物中之至少一者而成。
(5)如前項(4)之環氧樹脂組成物,其係含有導熱率20W/m‧K以上之無機填充材料而成。
(6)如前項(4)或(5)之環氧樹脂組成物,其係用於半導體密封用途。
(7)一種預浸體,其係由前項(4)或(5)之環氧樹脂組成物及片狀纖維基材構成。
(8)一種硬化物,其係使前項(4)至(6)中任一項之環氧樹脂組成物、或前項(7)之預浸體硬化而成。
(9)一種前項(3)之環氧樹脂之製造方法,其係於酚化合物與環氧鹵丙烷反應時,於反應系統內添加薄片狀氫氧化鈉。
(10)如前項(9)之製造方法,其係分複數次將上述薄片狀氫氧化鈉添加至反應系統內。
(11)如前項(9)或(10)之製造方法,其中,相對於上述酚化合物之羥基1莫耳,使用2~15莫耳上述環氧鹵丙烷。
(12)如前項(9)或(10)之製造方法,其中,相對於上述酚化合物之羥基1莫耳,使用2~4.5莫耳上述環氧鹵丙烷。
本發明之酚化合物及環氧樹脂由於其硬化物之導熱性優異,故而使用於以半導體密封材料、預浸體為代表之各種複合材料、接著劑、塗料等之情形時較為有用。另外,本發明之環氧樹脂由於熔點低於具有液晶性基之環氧樹脂,進而溶劑可溶性亦優異,故而可提供均勻之硬化物。
首先,對本發明之酚化合物進行說明。本發明之酚化合物係藉由選自下述式(1)~(5)所示之化合物中之一種以上與下述式(6)所示之化合物進行反應而獲得:
(式(1)中,R1分別獨立存在,表示氫原子、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、羥基、硝基、或碳數1~10之經取代或未經取代之烷氧基中之任一者,1表示R1數,為0~4之整數)。
於式(1)中,R1分別獨立存在,較佳為氫原子、碳數1~10之未經取代之烷基、碳數6~10之未經取代之芳基、羥基、硝基或碳數1~10之未經取代之烷氧基。
為獲得本發明之酚化合物,用於與式(6)所示之化合物進行反應的式(1)所示之化合物的具體例,可列舉:2-羥基苯乙酮、3-羥基苯乙酮、4-羥基苯乙酮、2',4'-二羥基苯乙酮、2',5'-二羥基苯乙酮、3',4'-二羥基苯乙酮、3',5'-二羥基苯乙酮、2',3',4'-三羥基苯乙酮、2',4',6'-三羥基苯乙酮一水合物、4'-羥基-3'-甲基苯乙酮、4'-羥基-2'-甲基苯乙酮、2'-羥基-5'-甲基苯乙酮、4'-羥基-3'-甲氧基苯乙酮、2'-羥基-4'-甲氧基苯乙酮、4'-羥基-3'-硝基苯乙酮、4'-羥基-3',5'-二甲氧基苯乙酮、4',6'-二甲氧基-2'-羥基苯乙酮、2'-羥基-3',4'-二甲氧基苯乙酮、2'-羥基-4',5'-二甲氧基苯乙酮、5-乙醯水楊酸甲酯、2',3'-二羥基-4'-甲氧基苯乙酮水合物。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,且環氧樹脂組成物之硬化物顯示高導熱性之方面而言,該等之中較佳為4'-羥基-3'-甲氧基苯乙酮、4'-羥基苯乙酮。
(式(2)中,R2分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~15之經取代或未經取代之烷羰基、碳數2~10之經取代或未經取代之烷基酯基、碳數1~10之經取代或未經取代之烷氧基、嗎啉基羰基、酞醯亞胺基、向日葵基、或羥基中之任一者)。
於式(2)中,上述取代基較佳為選自由羰基、酯基、烯基、苯基、烷氧基、醚基、酞醯亞胺基及向日葵基所組成之群中之至少1種。
為獲得本發明之酚化合物,用於與式(6)所示之化合物進行反應的式(2)所示之化合物之具體例,可列舉:丙酮(acetone)、1,3-二苯基-2-丙酮(propanone)、2-丁酮、1-苯基-1,3-丁二酮、2-戊酮、3-戊酮、4-甲基-2-戊酮、乙醯丙酮、2-己酮、3-己酮、異戊基甲基酮、乙基異丁基酮、4-甲基-2-己酮、2,5-己二酮、1,6-二苯基-1,6-己二酮、2-庚酮、3-庚酮、4-庚酮、2-甲基-4-庚酮、5-甲基-3-庚酮、6-甲基-2-庚酮、2,6-二甲基-4-庚酮、2-辛酮、3-辛酮、4-辛酮、5-甲基-2-辛酮、2-壬酮、3-壬酮、4-壬酮、5-壬酮、2-癸酮、3-癸酮、4-癸酮、5-癸酮、2-十一酮、3-十一酮、4-十一酮、5-十一酮、6-十一酮、2-甲基-4-十一酮、2-十二酮、3-十二酮、4-十二酮、5-十二酮、6-十二酮、2-十四酮、3-十四酮、8-十五酮、10-十九酮、7-十三酮、2-十五酮、3-十六酮、9-十七酮、11-二十一酮、12-二十三酮、14-二十七酮、16-三十一酮、18-三十五酮、4-乙氧基-2-丁酮、4-(4-甲氧基苯基)-2-丁酮、4-甲氧基-4-甲基-2-戊酮、4-甲氧基苯基丙酮、甲氧基丙酮、苯氧基丙酮、乙醯乙酸甲酯、乙醯乙酸乙酯、乙醯乙酸丙酯、乙醯乙酸丁酯、乙醯乙酸異丁酯、乙醯乙酸第二丁酯、乙醯乙酸第三丁酯、乙醯乙酸3-戊酯、乙醯乙酸戊酯、乙醯乙酸異戊酯、乙醯乙酸己酯、乙醯乙酸庚酯、乙醯乙酸正辛酯、乙醯乙酸苄酯、乙醯丁二酸二甲酯、丙酮基丙二酸二甲酯、丙酮基丙二酸二乙酯、乙醯乙酸-2-甲氧基乙酯、乙醯乙酸烯丙酯、4-第二丁氧基-2-丁酮、苄基丁基酮、雙去甲氧基薑黃素、1,1-二甲氧基-3-丁酮、1,3-二乙醯氧基丙酮、4-羥基苯基丙酮、4-(4-羥基苯基)-2-丁酮、異戊基甲基酮、4-羥基-2-丁酮、5-己烯-2-酮、丙酮基丙酮、3,4-二甲氧基苯基丙酮、向日葵基甲基酮、向日葵基丙酮、鄰苯二甲醯亞胺丙酮、4-異丙氧基-2-丁酮、4-異丁氧基-2-丁酮、乙醯氧基-2-丙酮、N-乙醯乙醯基嗎啉、1-乙醯-4-哌啶酮等。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,且環氧樹脂組成物之硬化物顯示高導熱性之方面而言,該等之中較佳為丙酮。
(式(3)中,R3分別獨立存在,表示氫原子、碳數0~10之經取代或未經取代之烷羰基、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數2~10之經取代或未經取代之烷基酯基、碳數1~10之經取代或未經取代之烷氧基、或羥基中之任一者。n表示碳數,表示0、1、2之任一整數。m表示R3數,滿足0≦m≦n+2之關係)。
再者,於式(3)中,R3為碳數0之經取代或未經取代之烷羰基之情況,係指包含構成通式(3)之主骨架即環烷烴的碳原子而成之羰基構造,例如可列舉1,3-環戊二酮等。
於式(3)中,上述取代基較佳為醚基或羰基。
為獲得本發明之酚化合物,用於與式(6)所示之化合物進行反應的式(3)所示之化合物之具體例,可列舉:環戊酮、3-苯基環戊酮、2-乙醯環戊酮、1,3-環戊二酮、2-甲基-1,3-環戊二酮、2-乙基-1,3-環戊二酮、環己酮、3-甲基環己酮、4-甲基環己酮、4-乙基環己酮、4-第三丁基環己酮、4-戊基環己酮、3-苯基環己酮、4-苯基環己酮、3,3-二甲基環己酮、3,4-二甲基環己酮、3,5-二甲基環己酮、4,4-二甲基環己酮、3,3,5-三甲基環己酮、2-乙醯環己酮、4-環己酮甲酸乙酯、1,4-環己二酮單乙二醇縮酮、雙環己烷-4,4'-二酮單乙二醇縮酮、1,4-環己二酮單-2,2-二甲基三亞甲基縮酮、2-乙醯-5,5-二甲基-1,3-環己二酮、1,2-環己二酮、1,3-環己二酮、1,4-環己二酮、2-甲基-1,3-環己二酮、5-甲基-1,3-環己二酮、達米酮、1,4-環己二酮-2,5-二甲酸二甲酯、4,4'-雙環己酮、2,2-雙(4-氧代環己基)丙烷、環庚酮等。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,且環氧樹脂組成物之硬化物顯示高導熱性之方面而言,該等之中較佳為環戊酮、環己酮、環庚酮、4-甲基環己酮。
(式(4)中,R12分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~10之經取代或未經取代之烷氧基、或羥基中之任一者)。
於式(4)中,R12分別獨立存在,較佳為氫原子、碳數1~20之未經取代之烷基、碳數6~10之未經取代之芳基、碳數1~10之未經取代之烷氧基、或羥基。
為獲得本發明之酚化合物,用於與式(6)所示之化合物進行反應的式(4)所示之化合物之具體例,可列舉:二乙醯、2,3-戊二酮、3,4-己二酮、5-甲基-2,3-己二酮、2,3-庚二酮等。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,且環氧樹脂組成物之硬化物顯示高導熱性之方面而言,該等之中較佳為二乙醯。
(式(5)中,R13分別獨立存在,表示氫原子、碳數1~20之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、碳數1~10之經取代或未經取代之烷氧基、碳數1~10之經取代或未經取代之烷基酯基、或羥基中之任一者。另外,m為1~10之整數)。
於式(5)中,R13分別獨立存在,較佳為氫原子、碳數1~20之未經取代之烷基、碳數6~10之未經取代之芳基、碳數1~10之未經取代之烷氧基、碳數1~10之未經取代之烷基酯基或羥基。
為獲得本發明之酚化合物,用於與式(6)所示之化合物進行反應的式(5)所示之化合物之具體例,可列舉:二乙醯乙酸乙酯、2,5-己二酮、3-甲基-2,4-戊二酮、3-乙基-2,4-戊二酮、3-丁基-2,4-戊二酮、3-苯基-2,4-戊二酮、4-乙醯-5-氧代己酸乙酯等。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,且環氧樹脂組成物之硬化物顯示高導熱性之方面而言,該等之中較佳為3-甲基-2,4-戊二酮、3-乙基-2,4-戊二酮。
(式(6)中,R4分別獨立存在,表示氫原子、碳數1~10之經取代或未經取代之烷基、碳數6~10之經取代或未經取代之芳基、羥基、硝基、甲醯基、烯丙基、或碳數1~10之經取代或未經取代之烷氧基中之任一者。k表示R4數,為0~4之整數)。
為獲得本發明之酚化合物,用於與選自式(1)~(5)所示之化合物中之1種以上進行反應的式(6)所示之化合物之具體例,例如可列舉:2-羥基苯甲醛、3-羥基苯甲醛、4-羥基苯甲醛、2,3-二羥基苯甲醛、2,4-二羥基苯甲醛、2,5-二羥基苯甲醛、3,4-二羥基苯甲醛、丁香醛、3,5-二-第三丁基-4-羥基苯甲醛、異香草醛、4-羥基-3-硝基苯甲醛、5-羥基-2-硝基苯甲醛、3,4-二羥基-5-硝基苯甲醛、香草醛、鄰香草醛、2-羥基-1-萘甲醛、2-羥基-5-硝基-間茴香醛、2-羥基-5-甲基異苯二甲醛、2-羥基-4-甲氧基苯甲醛、1-羥基-2-萘甲醛、2-羥基-5-甲氧基苯甲醛、5-硝基香草醛、5-烯丙基-3-甲氧基柳醛、3,5-二-第三丁基柳醛、3-乙氧基柳醛、4-羥基異苯二甲醛、4-羥基-3,5-二甲基苯甲醛、2,4,6-三羥基苯甲醛、2,4,5-三羥基苯甲醛、2,3,4-三羥基苯甲醛、3,4,5-三羥基苯甲醛、3-乙氧基-4-羥基苯甲醛等。該等可僅使用1種,亦可併用2種以上。就將所獲得之酚化合物環氧化時之溶劑可溶性較高,環氧樹脂組成物之硬化物顯示尤其高之導熱性之方面而言,該等之中較佳為單獨使用香草醛。
本發明之酚化合物係藉由式(1)~(5)所示之化合物中之一種以上與式(6)所示之化合物於酸性條件下或鹼性條件下進行醇醛縮合反應而獲得。
式(6)所示之化合物相對於式(1)所示之化合物1莫耳使用1.0~1.05莫耳,相對於式(2)、式(3)、式(4)及式(5)所示之化合物1莫耳使用2.0~3.15莫耳。
當於酸性條件下進行醇醛縮合反應時,可使用之酸性觸媒可列舉:鹽酸、硫酸、硝酸之類的無機酸,甲苯磺酸、二甲苯磺酸、草酸等有機酸。該等可單獨使用,亦可併用複數種。酸性觸媒之使用量相對於式(6)所示之化合物1莫耳為0.01~1.0莫耳,較佳為0.2~0.5莫耳。
另一方面,當於鹼性條件下進行醇醛縮合反應時,可使用之鹼性觸媒可列舉:氫氧化鈉及氫氧化鉀等金屬氫氧化物,碳酸鉀及碳酸鈉等碳酸鹼金屬鹽,二乙胺、三乙胺、三丁胺、二異丁胺、吡啶及哌啶等胺衍生物,及二甲基胺基乙醇及二乙基胺基乙醇等胺基醇衍生物。於鹼性條件下時,亦可單獨使用先前所列舉之鹼性觸媒,亦可併用複數種。鹼性觸媒之使用量相對於式(6)所示之化合物1莫耳為0.1~2.5莫耳,較佳為0.2~2.0莫耳。
於獲得本發明之酚化合物之反應中,亦可視需要使用溶劑。可使用之溶劑,只要為與例如如酮類之式(6)所示之化合物具有反應性者,則無特別限制,就易溶解原料之式(6)所示之化合物之方面而言,較佳為使用醇類作為溶劑。
反應溫度通常為10~90℃,較佳為35~70℃。反應時間通常為0.5~10小時,但由於反應性根據原料化合物之種類而存在差異,故而並不限制於此。反應結束後,於作為樹脂取出之情形時,於對反應物進行水洗後或不對其進行水洗,而於加熱減壓下自反應溶液中去除未反應物或溶劑等。於以結晶取出之情形時,藉由於大量水中滴加反應溶液而使結晶析出。當於鹼性條件下進行反應時,所生成之本發明之酚化合物亦可溶解於水中,因此添加鹽酸等,於中性~酸性條件下以結晶析出。
其次,對本發明之環氧樹脂進行說明。
本發明之環氧樹脂係藉由使利用上述方法獲得之本發明之酚化合物與環氧鹵丙烷進行反應,並進行環氧化而獲得。再者,於環氧化時,本發明之酚化合物可僅使用1種,亦可併用2種以上。另外,亦可於本發明之酚化合物中併用除本發明之酚化合物以外之酚化合物。
可併用之除本發明之酚化合物以外之酚化合物,只要為通常用作環氧樹脂之原料之酚化合物,則可無特別限制地使用,但有損害作為本發明之效果之硬化物具有高導熱率之虞,因此較佳為可併用之酚化合物之使用量極少,尤佳為僅使用本發明之酚化合物。
本發明之環氧樹脂,就顯示特別優異之溶劑可溶性且可獲得具有高導熱率之硬化物之方面而言,較佳為藉由式(6)所示之化合物與式(3)所示之化合物進行反應而獲得之本發明之酚化合物的環氧化物。
於獲得本發明之環氧樹脂之反應中,環氧鹵丙烷可使用環氧氯丙烷、α-甲基環氧氯丙烷、β-甲基環氧氯丙烷、環氧溴丙烷(epibromohydrin)等,較佳為工業上易獲得之環氧氯丙烷。環氧鹵丙烷之使用量相對於本發明之酚化合物之羥基1莫耳,通常為2~20莫耳,較佳為2~15莫耳,尤佳為2~4.5莫耳。環氧樹脂係藉由於鹼金屬氧化物之存在下使酚化合物與環氧鹵丙烷進行加成,繼而使所生成之1,2-鹵醇醚基開環並進行環氧化之反應而獲得。此時,可藉由如上所述之以明顯少於通常之量來使用環氧鹵丙烷,而增加環氧樹脂之分子量並且擴展分子量分佈。其結果顯示:所獲得之環氧樹脂可作為具有相對低之軟化點的樹脂狀物而自反應系統中取出,且顯示優異之溶劑可溶性。
於環氧化反應中可使用之鹼金屬氫氧化物,可列舉:氫氧化鈉、氫氧化鉀等,該等可直接使用固形物,或者亦可使用其水溶液。於使用水溶液之情形時,亦可為如下方法:連續地於反應系統內添加該鹼金屬氫氧化物之水溶液,並且藉由將於減壓下或常壓下連續地蒸餾出之水及環氧鹵丙烷之混合液進行分液來去除水,而僅使環氧鹵丙烷連續地返回至反應系統內。鹼金屬氫氧化物之使用量相對於本發明之酚化合物之羥基1莫耳,通常為0.9~3.0莫耳,較佳為1.0~2.5莫耳,更佳為1.0~2.0莫耳,尤佳為1.0~1.3莫耳。
另外,本發明人等達成如下見解:於環氧化反應中,藉由尤其使用薄片狀氫氧化鈉,可顯著降低使用製成水溶液之氫氧化鈉亦可得到之環氧樹脂所含之鹵素量。該鹵素來自環氧鹵丙烷,於環氧樹脂中混入越多越能夠降低硬化物之導熱性。進而,該薄片狀氫氧化鈉較佳為分割添加於反應系統內。藉由分割添加,可防止反應溫度之急劇下降,藉此可防止生成作為雜質之1,3-鹵醇體或鹵代甲烷體,可形成導熱率更高之硬化物。
為促進環氧化反應,較佳為添加氯化四甲銨、溴化四甲銨、氯化三甲基苄基銨等四級銨鹽作為觸媒。四級銨鹽之使用量相對於本發明之酚化合物之羥基1莫耳,通常為0.1~15g,較佳為0.2~10g。
另外,於環氧化時,就反應進行方面而言,較佳為添加甲醇、乙醇、異丙醇等醇類,二甲基碸、二甲基亞碸、四氫呋喃、二烷等非質子性極性溶劑等而進行反應。其中,較佳為醇類或二甲基亞碸。於使用醇類之情形時,可以高產率獲得環氧樹脂。另一方面,於使用二甲基亞碸之情形時,可更降低環氧樹脂中之鹵素量。
於使用上述醇類之情形時,其使用量相對於環氧鹵丙烷之使用量,通常為2~50質量%,較佳為4~35質量%。另外,於使用非質子性極性溶劑之情形時,其使用量相對於環氧鹵丙烷之使用量,通常為5~100質量%,較佳為10~80質量%。
反應溫度通常為30~90℃,較佳為35~80℃。反應時間通常為0.5~10小時,較佳為1~8小時。
於反應結束後,於對反應物進行水洗後或不對其進行水洗,而於加熱減壓下自反應溶液中去除環氧鹵丙烷或溶劑等。另外,為了進而降低所獲得之環氧樹脂中所含之鹵素量,亦可將所回收之本發明之環氧樹脂溶解於甲苯、甲基異丁基酮等溶劑中,並添加氫氧化鈉、氫氧化鉀等鹼金屬氫氧化物之水溶液進行反應而形成確實之閉環。此時,鹼金屬氫氧化物之使用量相對於本發明之酚化合物之羥基1莫耳通常為0.01~0.3莫耳,較佳為0.05~0.2莫耳。反應溫度通常為50~120℃,反應時間通常為0.5~2小時。
反應結束後,藉由利用過濾、水洗等去除所生成之鹽,進而於加熱減壓下蒸餾去除溶劑,而獲得本發明之環氧樹脂。另外,於本發明之環氧樹脂以結晶析出之情形時,亦可於大量水中溶解所生成之鹽後,過濾取得本發明之環氧樹脂之結晶。
如上所述,使用薄片狀氫氧化鈉而獲得之本發明之環氧樹脂的總鹵素量通常為1800ppm以下,較佳為1600ppm以下,更佳為700ppm以下。總鹵素量過多之環氧樹脂不僅對硬化物之電氣可靠性造成惡劣影響而且作為未交聯之末端而殘留,因此硬化時之熔融狀態下的分子未彼此取向,導致導熱性下降。
以下,對本發明之環氧樹脂組成物進行揭示。本發明之環氧樹脂組成物係含有本發明之環氧樹脂及本發明之酚化合物中之至少一者作為必需成分。
於本發明之環氧樹脂組成物中,本發明之環氧樹脂可單獨使用,或者亦可與其他環氧樹脂併用而使用。
其他環氧樹脂之具體例,可列舉:雙酚類(雙酚A、雙酚F、雙酚S、聯苯酚、雙酚AD及雙酚I等)或苯酚類(苯酚、烷基取代苯酚、芳香族取代苯酚、萘酚、烷基取代萘酚、二羥基苯(dihydroxybenzene)、烷基取代二羥基苯及二羥基萘等)與各種醛(甲醛、乙醛、烷基醛、苯甲醛、烷基取代苯甲醛、羥基苯甲醛、萘甲醛、戊二醛、苯二甲醛、巴豆醛(Crotonaldehyde)及肉桂醛(Cinnamaldehyde)等)之聚縮合物;二甲苯等芳香族化合物、甲醛之聚縮合物與苯酚類之聚縮合物;苯酚類與各種二烯化合物(二環戊二烯、萜烯類、乙烯環己烯、降冰片二烯(norbornadiene)、乙烯降冰片烯、四氫茚、二乙烯苯、二乙烯聯苯、二異丙烯聯苯、丁二烯及異戊二烯等)之聚合物;苯酚類與酮類(丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮及二苯甲酮等)之聚縮合物;苯酚類與芳香族二甲醇類(苯二甲醇及聯苯二甲醇等)之聚縮合物;苯酚類與芳香族二氯甲基類(α,α'-二氯二甲苯及雙氯甲基聯苯等)之聚縮合物;苯酚類與芳香族雙烷氧基甲基類(雙甲氧基甲基苯、雙甲氧基甲基聯苯及雙苯氧基甲基聯苯等)之聚縮合物;雙酚類與各種醛之聚縮合物;以及將醇類等環氧丙基化而成之環氧丙基醚系環氧樹脂、脂環族環氧樹脂、環氧丙基胺系環氧樹脂、環氧丙基酯系環氧樹脂等;只要為通常所使用之環氧樹脂,則並不限定於該等。該等可僅使用1種,亦可併用2種以上。
於併用其他環氧樹脂之情形時,於本發明之環氧樹脂組成物中本發明之環氧樹脂占總環氧樹脂成分之比例較佳為30質量%以上,更佳為40質量%以上,進而更佳為70質量%以上,尤佳為100質量%(未併用其他環氧樹脂之情形)。其中,於將本發明之環氧樹脂用作環氧樹脂組成物之改質劑之情形時,以於總環氧樹脂中成為1~30質量%之比例添加。
本發明之酚化合物作為硬化劑而包含於本發明之環氧樹脂組成物中。此時之硬化樹脂,可為上述本發明之環氧樹脂,亦可為除此以外之其他環氧樹脂。
於本發明之環氧樹脂組成物中,本發明之酚化合物可單獨使用,或者亦可與其他硬化劑併用而使用。
本發明之環氧樹脂組成物所含有之其他硬化劑,例如可列舉:胺系化合物、酸酐系化合物、醯胺系化合物及苯酚系化合物等。該等其他硬化劑之具體例示於下述(a)~(e)。
(a)胺系化合物:二胺基二苯甲烷、二伸乙三胺、三伸乙四胺、二胺基二苯基碸、異佛爾酮二胺及萘二胺等
(b)酸酐系化合物:苯二甲酸酐、苯偏三酸酐、焦蜜石酸二酐、順丁烯二酸酐、四氫苯二甲酸酐、甲基四氫苯二甲酸酐、甲基耐地酸酐、六氫苯二甲酸酐及甲基六氫苯二甲酸酐等
(c)醯胺系化合物:二氰基二醯胺、或二氰次亞麻油酸之二聚物與乙二胺合成之聚醯胺樹脂等
(d)苯酚系化合物:多酚類(雙酚A、雙酚F、雙酚S、茀雙酚、萜二酚、4,4'-二羥基聯苯、2,2'-二羥基聯苯、3,3',5,5'-四甲基-(1,1'-聯苯)-4,4'-二酚、對苯二酚、間苯二酚、萘二酚、三-(4-羥基苯基)甲烷及1,1,2,2-四(4-羥基苯基)乙烷等);藉由苯酚類(例如苯酚、烷基取代苯酚、萘酚、烷基取代萘酚、二羥基苯及二羥基萘等)與醛類(甲醛、乙醛、苯甲醛、對羥基苯甲醛、鄰羥基苯甲醛及糠醛等)、酮類(對羥基苯乙酮及鄰羥基苯乙酮等)或二烯類(二環戊二烯及三環戊二烯等)之縮合而獲得之苯酚樹脂;藉由上述苯酚類與取代聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)或取代苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)等之聚縮合而獲得之苯酚樹脂;上述苯酚類及/或上述苯酚樹脂之改質物;四溴雙酚A及溴化苯酚樹脂等之鹵化苯酚類
(e)其他咪唑類:BF3-胺錯合物、胍衍生物於該等其他硬化劑中,二胺基二苯甲烷、二胺基二苯基碸及萘二胺等胺系化合物,及鄰苯二酚與醛類、酮類、二烯類、取代聯苯類或取代苯基類之縮合物等具有鄰接活性氫基之構造的硬化劑由於有助於環氧樹脂之排列,故而較佳。
其他硬化劑可單獨使用,亦可併用複數種。於併用其他硬化劑之情形時,本發明之酚化合物占本發明之環氧樹脂組成物中之總硬化劑成分的比例較佳為20質量%以上,更佳為30質量%以上,再更佳為70質量%以上,尤佳為100質量%(於未併用其他硬化劑之情形)。
於本發明之環氧樹脂組成物中,包含本發明之酚化合物之總硬化劑之使用量相對於總環氧樹脂之環氧基1當量,較佳為0.5~2.0當量,尤佳為0.6~1.5當量。
本發明之環氧樹脂組成物,最佳為使用100質量%本發明之環氧樹脂作為環氧樹脂且使用100質量%本發明之酚化合物作為硬化劑之情形。
本發明之環氧樹脂組成物可視需要而藉由含有導熱性優異之無機填充材料來賦予其硬化物更優異之高導熱性。
本發明之環氧樹脂組成物所含之無機填充材料係用以賦予環氧樹脂組成物之硬化物更高之導熱率而添加,故於無機填充材料自身之導熱率過低之情形時,存在損害因環氧樹脂與硬化劑之組合而獲得之高導熱率之虞。因此,本發明之環氧樹脂組成物所含之無機填充材料,導熱率越高越好,只要具有通常為20W/m‧K以上、較佳為30W/m‧K以上、更佳為50W/m‧K以上之導熱率,則無任何限制。再者,此處所述之導熱率,係指藉由依據ASTM E1530之方法進行測定而獲得之值。具有此種特性之無機填充材料之具體例,可列舉:氮化硼、氮化鋁、氮化矽、碳化矽、氮化鈦、氧化鋅、碳化鎢、氧化鋁、氧化鎂等無機粉末填充材料,合成纖維、陶瓷纖維等纖維質填充材料,著色劑等。該等無機填充材料之形狀可為粉末(塊狀、球狀)、單纖維、長纖維等之任一者,尤其若為平板狀,則根據無機填充材料自身之積層效果而更提高硬化物之導熱性且進而提昇硬化物之放熱性,故而較佳。
本發明之環氧樹脂組成物中之無機填充材料之使用量相對於環氧樹脂組成物中之樹脂成分100質量份,通常為2~1000質量份,為儘量提高導熱率,較佳為於不妨礙本發明之環氧樹脂組成物之具體用途中之操作等的範圍內,儘可能增加無機填充材料之使用量。該等無機填充材料可僅使用1種,亦可併用2種以上。
另外,只要為可將填充材料整體之導熱率維持在20W/m‧K以上之範圍,則亦可於導熱率20W/m‧K以上之無機填充材料中併用導熱率未達20W/m‧K之填充材料,就本發明之目的:獲得導熱率儘可能較高的硬化物而言,導熱率未達20W/m‧K之填充材料之使用應該限制在最低限度。可併用之填充材料之種類或形狀並無特別限制。
於將本發明之環氧樹脂組成物用於半導體密封用途之情形時,就硬化物之耐熱性、耐濕性、力學性質等方面而言,較佳為於環氧樹脂組成物中,以占75~93質量%之比例使用導熱率為20W/m‧K以上之無機填充材料。此時,剩餘部分為環氧樹脂成分、硬化劑成分及其他視需要而添加之添加劑,添加劑為可併用之其他無機填充材料或下述硬化促進劑等。
於本發明之環氧樹脂組成物中,亦可含有硬化促進劑。可使用之硬化促進劑例如可列舉:2-甲基咪唑、2-乙基咪唑、2-苯基咪唑及2-乙基-4-甲基咪唑等咪唑類,2-(二甲基胺基甲基)苯酚、三乙二胺、三乙醇胺及1,8-二氮雜雙環(5,4,0)十一烯-7等三級胺類,三苯基膦、二苯基膦及三丁基膦等有機膦類,辛酸亞錫等金屬化合物,四苯基鏻-四苯基硼酸鹽及四苯基鏻-乙基三苯基硼酸鹽等四取代鏻-四取代硼酸鹽,2-乙基-4-甲基咪唑-四苯基硼酸鹽及N-甲基嗎啉-四苯基硼酸鹽等四苯基硼酸鹽等。硬化促進劑相對於環氧樹脂100質量份,可視需要使用0.01~15質量份。
於本發明之環氧樹脂組成物中,可視需要添加矽烷偶合劑、脫模劑及顏料等各種摻合劑,各種熱固性樹脂及各種熱塑性樹脂等。熱固性樹脂及熱塑性樹脂之具體例,可列舉:乙烯酯樹脂、不飽和聚酯樹脂、馬來醯亞胺樹脂、氰酸酯樹脂、異氰酸酯化合物、苯并化合物、乙烯苄基醚化合物、聚丁二烯及其改質物、丙烯腈共聚物之改質物、茚樹脂、氟樹脂、聚矽氧樹脂、聚醚醯亞胺、聚醚碸、聚苯醚、聚縮醛、聚苯乙烯、聚乙烯、二環戊二烯樹脂等。熱固性樹脂或熱塑性樹脂可以占本發明之環氧樹脂組成物60質量%以下之量來使用。
本發明之環氧樹脂組成物可藉由將上述各成分均勻混合而獲得,其較佳之用途可列舉半導體密封材料或印刷配線板等。
本發明之環氧樹脂組成物可利用與先前已知之方法同樣之方法容易地製成其硬化物。例如,可藉由利用熔融澆鑄法、轉注成型法、射出成型法、壓縮成型法等將如下方式所獲得之本發明之環氧樹脂組成物進行成型,進而於其熔點以上之溫度下加熱2~10小時,而獲得本發明之環氧樹脂組成物之硬化物,上述本發明之環氧樹脂組成物係將本發明之環氧樹脂組成物之必需成分即環氧樹脂、硬化劑及導熱率為20W/m‧K以上之無機填充材料,以及視需要添加之硬化促進劑、摻合劑、各種熱固性樹脂或各種熱塑性樹脂等,視需要利用擠出機、捏合機或輥等充分混合直至均勻而獲得。可藉由利用上述方法將搭載於導線架等之半導體元件密封,而將本發明之環氧樹脂組成物用於半導體密封用途。
另外,本發明之環氧樹脂組成物亦可製成含有溶劑之清漆。該清漆可藉由例如將於環氧樹脂、硬化劑中之至少一者含有本發明之環氧樹脂或本發明之酚樹脂之至少一者且視需要含有導熱率為20W/m‧K以上之無機填充材料等其他成分之混合物與如下有機溶劑混合而獲得,該有機溶劑係:甲苯、二甲苯、丙酮、甲基乙基酮、甲基異丁基酮、環己酮、環戊酮、N,N'-二甲基甲醯胺、N,N'-二甲基乙醯胺、二甲基亞碸、N-甲基吡咯烷酮、乙二醇二甲醚、乙二醇二乙醚、二丙二醇二甲醚、二丙二醇二乙醚、三乙二醇二甲醚、三乙二醇二乙醚等二醇醚類,乙酸乙酯、乙酸丁酯、甲基賽路蘇乙酸酯、乙基賽路蘇乙酸酯、丁基賽路蘇乙酸酯、卡必醇乙酸酯、丙二醇單甲醚乙酸酯、戊二酸二烷基酯、丁二酸二烷基酯、己二酸二烷基酯等酯類,γ-丁內酯等環狀酯類,石油醚、石油精、氫化石油精及石腦油溶劑等石油系溶劑等。溶劑之量相對於清漆整體,通常為10~95質量%,較佳為15~85質量%。
可藉由以下方式獲得本發明之預浸體:將以上述方式獲得之清漆含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維及紙等纖維基材之後,利用加熱去除溶劑並且將本發明之環氧樹脂組成物形成為半硬化狀態。再者,此處所謂「半硬化狀態」,係指作為反應性官能基之環氧基一部分未進行反應而剩餘之狀態。可對該預浸體進行熱壓成型而獲得硬化物。
[實施例]
以下,利用實施例對本發明進行更詳細地說明,但本發明並不限定於該等實施例。於合成例、實施例、比較例中,份係指質量份。
再者,環氧當量、熔點、軟化點、全氯量、導熱率係於以下之條件下進行測定。
‧環氧當量
藉由JIS K-7236所記載之方法進行測定,單位為g/eq.。
‧熔點
Seiko Instruments Inc.製造之EXSTAR6000
測定試樣:2mg~5mg,升溫速度:10℃/min.
‧軟化點
藉由依據JIS K-7234之方法進行測定,單位為℃。
‧全氯量
於試樣之丁基卡必醇溶液中添加1N-KOH丙二醇溶液,回流10分鐘,藉此利用硝酸銀滴定法測定游離之氯量(莫耳),並除以試樣之重量而獲得之值。
‧導熱率
藉由依據ASTM E1530之方法進行測定,單位為W/m‧K。
實施例1
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中添加136份4'-羥基苯乙酮、152份香草醛及200份乙醇並溶解。於其中添加20份97質量%之硫酸後升溫至60℃,於該溫度下反應10小時後,將反應溶液注入至1200份水中進行晶析。濾出結晶後,利用600份水水洗2次,其後進行真空乾燥,而獲得256份黃色結晶之酚化合物1。對所獲得之結晶進行DSC測定而獲得之吸熱峰值溫度為233℃。
實施例2
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中添加166份4'-羥基-3'-甲氧基苯乙酮、122份4-羥基苯甲醛及200份乙醇並溶解。於其中添加20份97%之硫酸後升溫至50℃,於該溫度下反應10小時後,將反應溶液注入至1200份水中進行晶析。濾出結晶後,利用600份水水洗2次,其後進行真空乾燥,而獲得285份茶褐色結晶之酚化合物2。藉由對所獲得之結晶進行DSC測定而獲得之吸熱峰值溫度為193℃。
實施例3
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中添加56份4-甲基環己酮、152份香草醛及150份乙醇並溶解。添加10份97質量%之硫酸後升溫至50℃,於該溫度下反應10小時後,添加25份三聚磷酸鈉並攪拌30分鐘。其後添加500份甲基異丁基酮後,利用200份水水洗2次,其後利用蒸發器蒸餾去除溶劑,而獲得304份半固形之酚化合物3。
實施例4
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加135份實施例1中所獲得之酚化合物1、925份環氧氯丙烷、139份二甲基亞碸(以下為DMSO),於攪拌下升溫至45℃而溶解,用90分鐘分次添加40份薄片狀氫氧化鈉後,於45℃下維持1.5小時,其後升溫至70℃,進行30分鐘之反應。反應結束後,利用旋轉蒸發器於70℃、減壓下,蒸餾去除800份過剩之環氧氯丙烷等溶劑。將殘留物注入至1500份水中而使結晶析出。將結晶過濾後,利用600份甲醇進行清洗,其後於70℃下進行真空乾燥,藉此獲得181份環氧樹脂1。所獲得之環氧樹脂之環氧當量為210g/eq.,藉由DSC測定而獲得之吸熱峰值溫度為118℃、130℃。另外,測定所獲得之環氧樹脂之全氯量,結果為1400ppm。
實施例5
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面進行氮氣沖洗一面添加135份實施例2中所獲得之酚化合物2、925份環氧氯丙烷、139份DMSO,於攪拌下升溫至45℃而溶解,用90分鐘分次添加40份薄片狀氫氧化鈉後,於45℃下維持1.5小時,其後升溫至70℃,進行30分鐘之反應。反應結束後,利用旋轉蒸發器於70℃、減壓下,蒸餾去除800份過剩之環氧氯丙烷等溶劑。將殘留物注入至1500份水中而使結晶析出。將結晶過濾後利用600份甲醇進行清洗,其後於70℃下進行真空乾燥,藉此獲得180份環氧樹脂2。所獲得之環氧樹脂之環氧當量為212g/eq.,利用DSC測定之熔點為133℃。另外,測定所獲得之環氧樹脂之全氯量,結果為1500ppm。
實施例6
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加160份實施例3中所獲得之酚化合物3、925份環氧氯丙烷、139份DMSO,於攪拌下升溫至45℃而溶解,用90分鐘分次添加40份薄片狀氫氧化鈉後,於45℃下維持1.5小時,其後升溫至70℃進行30分鐘之反應。反應結束後,利用旋轉蒸發器於70℃、減壓下,蒸餾去除800份過剩之環氧氯丙烷等溶劑。將殘留物注入至1500份水中而使結晶析出。將結晶過濾後利用600份甲醇進行清洗,其後於70℃下進行真空乾燥,藉此獲得199份環氧樹脂3。所獲得之環氧樹脂之環氧當量為298g/eq.,利用DSC測定之熔點為119℃。另外,測定所獲得之環氧樹脂之全氯量,結果為1450ppm。
實施例7~15及比較例1、2
以表1之比例(份)摻合各種成分,利用混練機混練且製成錠劑後,藉由轉注成形製備樹脂成形體,於160℃下加熱2小時,進而於180℃下加熱8小時,而獲得本發明之環氧樹脂組成物及比較用樹脂組成物之硬化物。測定該等硬化物之導熱率而獲得之結果示於表1。
環氧樹脂4:下述式(7)所示之環氧樹脂(商品名:NC-3000,日本化藥製造,環氧當量為276g/eq.)
環氧樹脂5:含有等莫耳下述式(8)及(9)所示之環氧樹脂之聯苯型環氧樹脂(商品名:YL-6121H,Japan Epoxy Resin製造,環氧當量為175g/eq.)
硬化劑1:實施例1中所獲得之酚化合物1
硬化劑2:實施例2中所獲得之酚化合物2
硬化劑3:實施例3中所獲得之酚化合物3
硬化劑4:下述式(10)所示之苯酚酚醛清漆(商品名:H-1,明和化成製造,羥基當量為105g/eq.)
硬化促進劑:三苯基膦(北興化學工業製造)
實施例16~24及比較例3、4
以表2之比例(份)摻合各種成分,利用混練機混練且製成錠劑後,藉由轉注成形製備樹脂成形體,於160℃下加熱2小時,進而於180℃下加熱8小時,而獲得本發明之環氧樹脂組成物及比較用樹脂組成物之硬化物。測定該等硬化物之導熱率之結果示於表2。
無機填充材料1:球狀氧化鋁(商品名:DAW-100,電氣化學工業製造,導熱率為38W/m‧K)
無機填充材料2:氮化硼(商品名:SGP,電氣化學工業製造,導熱率為60W/m‧K)
實施例25
於70℃下使100份實施例6中所獲得之環氧樹脂3溶解於1000份二甲基甲醯胺中之後,恢復至室溫。於70℃下使13份作為硬化劑之1,5-萘二胺(東京化成製造,胺當量為40g/eq.)溶解於48份二甲基甲醯胺中之後,恢復至室溫。利用攪拌翼類型之均質攪拌機將上述環氧樹脂溶液與硬化劑溶液加以混合、攪拌而製成均勻之清漆,進而添加無機填充材料(商品名:SGP,電氣化學工業製造,導熱率為60W/m‧K)215份(相對於樹脂固形物成分100體積份為50體積份)及二甲基甲醯胺100份進行混合、攪拌,而製備本發明之環氧樹脂組成物。
使該環氧樹脂組成物之清漆含浸於厚度0.2mm之玻璃纖維織布(商品名:7628/AS890AW,Asahi-Schwebel製造)並進行加熱乾燥而獲得預浸體。使4片該預浸體與配置於其兩側之銅箔重疊後,於溫度175℃、壓力4MPa之條件下進行90分鐘之加熱加壓成型使其成為一體,而獲得厚度0.8mm之積層板。測定該積層板之導熱率,結果為4.9W/m‧K。
實施例26
於70℃下使100份環氧樹脂4(NC-3000)、369份實施例3中所獲得之酚化合物溶解於1000份二甲基甲醯胺之後,恢復至室溫。於70℃下使1份作為硬化促進劑之三苯基膦(北興化學工業製造)溶解於48份二甲基甲醯胺中之後,恢復至室溫。利用攪拌翼類型之均質攪拌機將上述環氧樹脂溶液與硬化促進劑溶液進行混合、攪拌而製成均勻之清漆,進而添加無機填充材料(商品名:SGP電氣化學工業製造,導熱率為60W/m‧K)321份(相對於樹脂固形物成分100體積份為50體積份)及二甲基甲醯胺100份並進行混合、攪拌,而製備本發明之環氧樹脂組成物。
使該環氧樹脂組成物之清漆含浸於厚度0.2mm之玻璃纖維織布(商品名:7628/AS890AW Asahi-Schwebel製造)中並進行加熱乾燥而獲得預浸體。使4片該預浸體與配置於其兩側之銅箔重疊後,於溫度175℃、壓力4MPa之條件下進行90分鐘加熱加壓成型使其成為一體,而獲得厚度0.8mm之積層板。測定該積層板之導熱率,結果為4.7W/m‧K。
比較例5
除將實施例25中之環氧樹脂3變更為100份環氧樹脂5(YL-6121H),將1,5-萘二胺之量變更為23份,將無機填充材料之量變更為234份以外,藉由與實施例25相同之操作次序而獲得積層板。測定該積層板之導熱率,結果為3.6W/m‧K。
比較例6
除將實施例26中之369份酚化合物變更為29份式(10)所示之苯酚酚醛清漆樹脂,將無機填充材料之量變更為245份以外,藉由與實施例26相同之操作次序而獲得積層板。測定該積層板之導熱率,結果為3.9W/m‧K。
實施例27
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中添加29份丙酮、152份香草醛及300份乙醇並溶解。於其中添加80份50%之氫氧化鈉水溶液後升溫至45℃,於該溫度下反應120小時後,將反應溶液注入至800mL1.5N之鹽酸中進行晶析。濾出結晶後,利用600份水水洗2次,其後進行真空乾燥,而獲得165份黃色結晶之苯酚化合物4。對所獲得之結晶藉由DSC測定而獲得之熔點為201℃。
實施例28
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加163份實施例27中所獲得之苯酚化合物4、925份環氧氯丙烷、139份DMSO,於攪拌下升溫至45℃而溶解,用90分鐘分次添加40份薄片狀氫氧化鈉後,於45℃下維持1.5小時,其後升溫至70℃進行30分鐘反應。反應結束後,利用旋轉蒸發器,於70℃、減壓下,蒸餾去除800份過剩之環氧氯丙烷等溶劑。將殘留物注入至1500份水中而使結晶析出。將結晶過濾後,利用600份甲醇進行清洗,其後於70℃下進行真空乾燥,藉此獲得200份環氧樹脂6。所獲得之環氧樹脂之環氧當量為256g/eq.,藉由DSC而獲得之熔點為140℃。另外,測定所獲得之環氧樹脂之全氯量,結果為1400ppm。
實施例29
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加135份合成例1中所獲得之酚化合物1、278份環氧氯丙烷、93份二甲基亞碸、6份水,於攪拌下升溫至40℃,用90分鐘分次添加42份薄片狀氫氧化鈉後,於40℃下維持2小時,於50℃下攪拌2小時,於70℃下攪拌1小時而進行反應。反應結束後,利用旋轉蒸發器於130℃、減壓下,自油層蒸餾去除過剩之環氧氯丙烷或二甲基亞碸等。於殘留物中添加473份甲基異丁基酮而溶解,升溫至70℃。對溶液進行水洗而去除鹽之後,再次升溫至70℃,於攪拌下添加11份30重量%之氫氧化鈉水溶液,反應1小時後,進行水洗直至清洗水成為中性,利用旋轉蒸發器於180℃、減壓下,自所獲得之溶液中蒸餾去除甲基異丁基酮等,藉此獲得173份目標環氧樹脂7。所獲得之環氧樹脂之環氧當量為236g/eq.,JIS軟化點為63℃,全氯量為550ppm。
實施例30
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加135份合成例1中所獲得之酚化合物1、278份環氧氯丙烷、28份甲醇,於攪拌下升溫至70℃而溶解,用90分鐘分次添加42份薄片狀氫氧化鈉後,於70℃下維持進行1.5小時之反應。反應結束後進行水洗,其後利用旋轉蒸發器於130℃、減壓下,自油層蒸餾去除過剩之環氧氯丙烷等。於殘留物中添加382份甲基異丁基酮進行溶解並升溫至70℃。於攪拌下添加12份30重量%之氫氧化鈉水溶液,於70℃下維持進行75分鐘之反應後,進行水洗直至清洗水成為中性,利用旋轉蒸發器於180℃、減壓下,自所獲得之溶液中蒸餾去除甲基異丁基酮等,藉此獲得175份目標環氧樹脂8。所獲得之環氧樹脂之環氧當量為225g/eq.,JIS軟化點為55℃,全氯量為600ppm。
使用氫氧化鈉水溶液之參考例
於具備攪拌機、回流冷卻管、攪拌裝置之燒瓶中,一面實施氮氣沖洗一面添加135份實施例1中所獲得之酚化合物1、231份環氧氯丙烷,於攪拌下升溫至90℃後添加125份16%氫氧化鈉水溶液,其後於90℃下維持攪拌40分鐘,其後進而添加25份40%之氫氧化鈉水溶液而進行20分鐘之反應。反應結束後進行水洗,其後利用旋轉蒸發器於135℃、減壓下,蒸餾去除過剩之環氧氯丙烷等。將殘留物溶解於382份甲基異丁基酮中之後,再次水洗,其後利用旋轉蒸發器於180℃、減壓下,去除甲基異丁基酮等低沸點成分,而獲得181份環氧樹脂9。所獲得之環氧樹脂之環氧當量為270g/eq.,軟化點為68℃。另外,測定所獲得之環氧樹脂之全氯量,結果為5000ppm以上。
含有藉由該等操作而獲得之環氧樹脂1~3、6~8之各種環氧樹脂於60℃、100℃下且樹脂濃度30%下之相對於甲基異丁基酮之可溶性示於表3。
實施例31~37,比較例1、27,參考例1
以表4之比例(份)摻合各種成分,利用混練機混練且製成錠劑後,藉由轉注成形製備樹脂成形體,於160℃下加熱2小時,進而於180℃下加熱8小時,而獲得本發明之環氧樹脂組成物及比較用樹脂組成物之硬化物。測定該等硬化物之導熱率之結果示於表4。
硬化劑5:實施例27中所獲得之酚化合物4
實施例38~44,比較例3、4,參考例2
以表5之比例(份)摻合各種成分,利用混練機混練且製成錠劑後,藉由轉注成形製備樹脂成形體,於160℃下加熱2小時,進而於180℃下加熱8小時,而獲得本發明之環氧樹脂組成物及比較用樹脂組成物之硬化物。測定該等硬化物之導熱率,結果示於表5。
根據以上之結果可確認本發明之環氧樹脂之溶劑可溶性優異,且含有本發明之酚化合物、環氧樹脂中之至少一者之環氧樹脂組成物的硬化物具有優異之導熱性。尤其可確認藉由使用薄片狀氫氧化鈉作為環氧化時之鹼金屬氧化物,可降低全氯量,顯示出良好之導熱性。另外,藉由分次添加,可防止生成雜質即1,3-鹵醇體或鹵代甲烷體,進而可提昇導熱率。
因此,本發明之酚化合物及環氧樹脂使用於電氣、電子構件用絕緣材料及積層板(印刷配線板等)等之情形時極其有用。
已參照特定之態樣對本發明進行詳細說明,但業者明確只要不偏離本發明之精神與範圍可進行各種變更及修正。
再者,本申請案係基於2010年1月29日申請之日本專利申請案(日本特願2010-019269),以引用之方式而援引其全文。另外,所引用之全部參照全部引用於本文中。
[產業上之可利用性]
本發明之環氧樹脂組成物之硬化物與先前之環氧樹脂之硬化物相比,具有優異之導熱性,並且溶劑可溶性亦優異。因此作為密封材料、預浸體等,於電氣電子材料、成型材料、澆鑄材料、積層材料、塗料、接著劑、抗蝕劑、光學材料等廣泛之用途中極其有用。
Claims (12)
- 一種接合高導熱部位之用於黏合劑的高分子材料用之酚化合物,其係藉由下述式(1)~(5)所示之化合物之一種以上與下述式(6)所示之化合物進行反應而獲得:
- 一種接合高導熱部位之用於黏合劑的高分子材料用之環氧樹脂,其係使環氧鹵丙烷(epihalohydrin)與申請專利範圍第1項之酚化合物進行反應而獲得。
- 如申請專利範圍第2項之接合高導熱部位之用於黏合劑的高分子材料用之環氧樹脂,其中,總鹵素量為1800ppm以下。
- 一種接合高導熱部位之用於黏合劑的高分子材料用之環氧樹脂組成物,其係含有申請專利範圍第2或3項之環氧樹脂、申請專利範圍第1項之酚化合物中之至少一者而成。
- 如申請專利範圍第4項之接合高導熱部位之用於黏 合劑的高分子材料用之環氧樹脂組成物,其係含有導熱率20W/m.K以上之無機填充材料而成。
- 如申請專利範圍第4或5項之接合高導熱部位之用於黏合劑的高分子材料用之環氧樹脂組成物,其係用於半導體密封用途。
- 一種預浸體,其係由申請專利範圍第4或5項之環氧樹脂組成物及片狀纖維基材構成。
- 一種硬化物,其係使申請專利範圍第4至6項中任一項之環氧樹脂組成物、或申請專利範圍第7項之預浸體硬化而成。
- 一種申請專利範圍第3項之環氧樹脂之製造方法,其係於酚化合物與環氧鹵丙烷反應時,於反應系統內添加薄片狀氫氧化鈉。
- 如申請專利範圍第9項之製造方法,其係分複數次將該薄片狀氫氧化鈉添加至反應系統內。
- 如申請專利範圍第9或10項之製造方法,其中,相對於該酚化合物之羥基1莫耳,使用2~15莫耳該環氧鹵丙烷。
- 如申請專利範圍第9或10項之製造方法,其中,相對於上述酚化合物之羥基1莫耳,使用2~4.5莫耳該環氧鹵丙烷。
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JP2817474B2 (ja) * | 1991-09-25 | 1998-10-30 | 信越化学工業株式会社 | エポキシ樹脂組成物及び硬化物 |
JPH0597948A (ja) * | 1991-10-09 | 1993-04-20 | Sumitomo Chem Co Ltd | 多価フエノール、それから誘導されるエポキシ樹脂及びエポキシ樹脂組成物 |
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JPH09100339A (ja) * | 1994-09-08 | 1997-04-15 | Sumitomo Chem Co Ltd | エポキシ樹脂組成物および樹脂封止型半導体装置 |
JPH11106472A (ja) * | 1997-10-06 | 1999-04-20 | Nippon Kayaku Co Ltd | エポキシ樹脂の製造法 |
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KR101002935B1 (ko) * | 2003-10-27 | 2010-12-21 | 삼성전자주식회사 | 에폭시기 및 찰콘기를 가지는 화합물, 이의 제조 방법 및이를 포함하는 포토레지스트 조성물 |
DE10360546A1 (de) * | 2003-12-22 | 2005-07-14 | Patent-Treuhand-Gesellschaft für elektrische Glühlampen mbH | Leuchtstoff und Lichtquelle mit derartigem Leuchtstoff |
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JP4706904B2 (ja) * | 2005-05-31 | 2011-06-22 | Dic株式会社 | エポキシ樹脂組成物、その硬化物、新規エポキシ樹脂及びその製造方法 |
JP5224366B2 (ja) * | 2008-05-29 | 2013-07-03 | 日本化薬株式会社 | エポキシ樹脂組成物、プリプレグおよび硬化物 |
JP2010019269A (ja) | 2008-07-08 | 2010-01-28 | Ntn Corp | 回転速度検出装置付き車輪用軸受装置およびその組立方法 |
-
2011
- 2011-01-28 WO PCT/JP2011/051832 patent/WO2011093474A1/ja active Application Filing
- 2011-01-28 US US13/575,661 patent/US20120296011A1/en not_active Abandoned
- 2011-01-28 CN CN201410144317.2A patent/CN103980103B/zh active Active
- 2011-01-28 KR KR1020177018035A patent/KR20170078885A/ko not_active Application Discontinuation
- 2011-01-28 KR KR1020127019904A patent/KR20120120267A/ko not_active Application Discontinuation
- 2011-01-28 CN CN201180007760.XA patent/CN102741315B/zh active Active
- 2011-01-28 DE DE112011100378T patent/DE112011100378T5/de not_active Withdrawn
- 2011-01-28 TW TW100103607A patent/TWI522340B/zh active
- 2011-01-28 JP JP2011551947A patent/JP5757879B2/ja active Active
-
2015
- 2015-06-02 JP JP2015112028A patent/JP6033919B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
CN103980103B (zh) | 2017-04-12 |
JPWO2011093474A1 (ja) | 2013-06-06 |
WO2011093474A1 (ja) | 2011-08-04 |
KR20120120267A (ko) | 2012-11-01 |
US20120296011A1 (en) | 2012-11-22 |
TW201144268A (en) | 2011-12-16 |
CN103980103A (zh) | 2014-08-13 |
CN102741315B (zh) | 2014-12-03 |
JP6033919B2 (ja) | 2016-11-30 |
CN102741315A (zh) | 2012-10-17 |
JP5757879B2 (ja) | 2015-08-05 |
JP2015232131A (ja) | 2015-12-24 |
DE112011100378T5 (de) | 2012-12-06 |
KR20170078885A (ko) | 2017-07-07 |
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