CN103857722A - Epoxy resin mixture, epoxy resin composition, prepreg, and curing product of each - Google Patents
Epoxy resin mixture, epoxy resin composition, prepreg, and curing product of each Download PDFInfo
- Publication number
- CN103857722A CN103857722A CN201280036890.0A CN201280036890A CN103857722A CN 103857722 A CN103857722 A CN 103857722A CN 201280036890 A CN201280036890 A CN 201280036890A CN 103857722 A CN103857722 A CN 103857722A
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- carbonatoms
- phenolic compound
- formula
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 213
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 213
- 239000000203 mixture Substances 0.000 title claims description 163
- -1 phenol compound Chemical class 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000002989 phenols Chemical class 0.000 claims description 101
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000000463 material Substances 0.000 claims description 51
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000011049 filling Methods 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 239000004065 semiconductor Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 3
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 41
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 41
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 40
- 239000000243 solution Substances 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- 238000005406 washing Methods 0.000 description 21
- 230000006837 decompression Effects 0.000 description 19
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000004821 distillation Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000013019 agitation Methods 0.000 description 16
- 239000004593 Epoxy Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst 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
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 238000006735 epoxidation reaction Methods 0.000 description 13
- 239000011120 plywood Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 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
- 230000000052 comparative effect Effects 0.000 description 8
- 238000011033 desalting Methods 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 238000010926 purge Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 239000002585 base Substances 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 125000005594 diketone group Chemical group 0.000 description 5
- 235000012141 vanillin Nutrition 0.000 description 5
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 4
- 150000004780 naphthols Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 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
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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 compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005575 aldol reaction Methods 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-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
- 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
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-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
- LXBHHIZIQVZGFN-UHFFFAOYSA-N 4-hydroxy-3-methylacetophenone Chemical compound CC(=O)C1=CC=C(O)C(C)=C1 LXBHHIZIQVZGFN-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
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-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
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 2
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
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- 150000003456 sulfonamides Chemical class 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-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
- 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
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound 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
- 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
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000006200 vaporizer Substances 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
-
- 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
- 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
Abstract
The present invention provides an epoxy resin having a curing product that has a high thermal conductivity, and having a low viscosity and superior workability. The epoxy resin contains an epoxy resin (A) obtained by reacting epihalohydrin and a phenol compound (a) obtained by reacting the compounds represented by formula (1) and formula (6), and further contains: an epoxy resin (B) obtained by reacting epihalohydrin to the phenol compound (b) represented by formula (7); and/or an epoxy resin (C) obtained by reacting epihalohydrin and the phenol compound (c) represented by formula (8).
Description
Technical field
The present invention relates to neo-epoxy resin mixture and composition epoxy resin.In addition, relate to the cured article of prepreg of being formed by this composition epoxy resin etc.
Background technology
Composition epoxy resin generally can become the good cured articles such as mechanical properties, water tolerance, chemical-resistant, thermotolerance, electrical property, is applied to the field widely such as tackiness agent, coating, plywood, shaped material, mould material.In recent years, for the cured article of the epoxy resin using in these fields, require with high purity turn to representative, every characteristic such as flame retardant resistance, thermotolerance, wet fastness, toughness, low linear expansion rate, low-k characteristic further improves.
Especially, be in electric and electronic industrial field in the representative purposes of composition epoxy resin, carrying out with multifunction, high performance, the small-sized semi-conductive high-density installation of object and the high-density wiring of printed wiring board of turning to, but follow high-density installation and high-density wiring, what produce from semiconductor element or printed wiring intralamellar part is heat gain, may become the reason that causes mishandle.Therefore, how the heat of generation is discharged into outside effectively, also becomes important problem from energy efficiency, equipment design aspect.As these hot countermeasures, carry out using metal core substrate, assembling the structure of easily heat radiation or compactly fill the various designs such as high thermal conduction filler in used polymer materials (epoxy resin) in the design phase.But low as the thermal conductivity of polymer materials of adhesive acts that connects high thermal conduction position, therefore the heat conduction velocity of polymer materials becomes rate-limiting step, present case is still can not effectively dispel the heat.
As the means of high thermal conduction that realize epoxy resin, in patent documentation 1, report and in structure, introduced mesomorphic group, in the document, record and there is epoxy resin of biphenyl backbone etc. as the epoxy resin with mesomorphic group.In addition, the epoxy resin of having recorded phenol benzoate type is as the epoxy resin beyond biphenyl backbone, but this epoxy resin need to manufacture by the epoxidation reaction based on oxidation, there is obstacle in security and cost aspect therefore, can not say practical.There is the example of the epoxy resin of biphenyl backbone as use, can enumerate patent documentation 2~4, wherein, in patent documentation 3, recorded the method that is used in combination the inorganic filling material with high heat conductance.But, the heat conductivity of the cured article obtaining by the method for recording in these documents not meets the level of market demand, requires to use the epoxy resin that can obtain more cheaply, the composition epoxy resin that the cured article with higher thermal conductivity is provided.
In addition, in order to obtain having the cured article of high thermal conductivity, as the desired characteristic of epoxy resin, certainly can be set forth in while forming cured article and show high thermal conductivity, still, in addition, the melt viscosity of resin is low is also important characteristic.Generally speaking, high thermal conduction filler is compared with general filler, and particle shape majority is non-spherical, is difficult to high filling.Therefore, epoxy resin viscosity under molten state is lower, and workability more improves.Therefore,, in order to be the desired level in market by the viscosity adjustment of epoxy resin, strongly wish lowering viscousity.
Prior art document
Patent documentation
Patent documentation 1: Japanese kokai publication hei 11-323162 communique
Patent documentation 2: TOHKEMY 2004-2573 communique
Patent documentation 3: TOHKEMY 2006-63315 communique
Patent documentation 4: TOHKEMY 2003-137971 communique
Summary of the invention
Invent problem to be solved
The present invention is the result of studying in order to solve such problem, provide its cured article have high thermal conductivity, low viscosity and the good epoxy resin composition of workability.
For the means of dealing with problems
The inventor has carried out research extensively and profoundly in order to solve aforementioned problems, and result has completed the present invention.
, the present invention relates to:
(1) a kind of epoxy resin composition, its phenolic compound (a) obtaining that reacts that contains more than one compounds that represent with following formula (6) in the compound that makes to represent by following formula (1)~(5) reacts the epoxy resin (A) obtaining with epihalohydrins, and contain that phenolic compound (b) by epihalohydrins and following formula (7) are represented react the epoxy resin (B) that obtains and/or by making epihalohydrins react with the phenolic compound (c) of following formula (8) expression the epoxy resin (C) obtaining
In formula (1), R
1exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro or the carbonatoms 1~10 of carbonatoms 6~10, l represents R
1number, be 1~4 integer;
In formula (2), R
2there is independently of one another any one in alkoxyl group, morpholinyl carbonyl, phthalimide-based, piperonyl or the hydroxyl of the alkyl-carbonyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~15, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10;
In formula (3), R
3exist independently of one another, any one in alkoxyl group or the hydroxyl of the aryl of the alkyl-carbonyl of expression hydrogen atom, carbonatoms 0~10, the alkyl of carbonatoms 1~10, carbonatoms 6~10, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10, n represents carbonatoms, represent any one integer in 0,1,2, m represents R
3number, meet the relation of 1≤m≤n+2;
In formula (4), R
4there is independently of one another any one in alkoxyl group or the hydroxyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10;
In formula (5), R
5exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10, alkyl ester group or the hydroxyl of carbonatoms 1~10, in addition, the integer that m is 1~10;
In formula (6), R
6exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro, formyl radical, allyl group or the carbonatoms 1~10 of carbonatoms 6~10, k represents R
6number, be 1~4 integer;
In formula (7), R
7, X and Y exist independently of one another, represents any one in the alkoxyl group of alkyl or aryl, hydroxyl or carbonatoms 1~10 of hydrogen atom, carbonatoms 1~10, k represents R
7number, represent 1~4 integer;
In formula (8), R
8exist independently of one another, any one in the alkoxyl group of alkyl or aryl, hydroxyl or the carbonatoms 1~10 of expression hydrogen atom, carbonatoms 1~10, l represents R
8number, represent 1~4 integer, A represents direct key or has the alkylidene of the carbonatoms 5~15 of cyclic rings.
(2) epoxy resin composition as described in (1), it is by making epihalohydrins and containing phenolic compound (a) and contain phenolic compound (b) and/or the phenolic compound mixture reaction of phenolic compound (c) obtains.
(3) epoxy resin composition as described in (2), it obtains by the mixture reaction that makes epihalohydrins and phenolic compound, and the mixture of described phenolic compound is that in the mixture of the described phenolic compound (a) of the preceding paragraph (1) of reacting with epihalohydrins~(c), phenolic compound (b) and the shared ratio sum of phenolic compound (c) are the mixture of the phenolic compound of 1~30 quality %.
(4) composition epoxy resin, it contains epoxy resin composition and the solidifying agent described in any one in (1)~(3).
(5) composition epoxy resin, wherein, in the composition epoxy resin (4) Suo Shu, contains phenolic compound (a) as solidifying agent.
(6) composition epoxy resin as described in (4) or (5), wherein, contains inorganic filling material more than thermal conductivity 20W/mK.
(7) composition epoxy resin as described in any one in (4)~(6), it is for encapsulating semiconductor purposes.
(8) prepreg, it comprises in (4)~(6) composition epoxy resin described in any one and the fiber base material of sheet.
(9) cured article, it is by solidifying the composition epoxy resin described in any one in (4)~(7) or the described prepreg of preceding paragraph (8) to obtain.
Invention effect
The melt viscosity of epoxy resin composition of the present invention is low, and therefore workability is good, and in addition, the thermal conduction of its cured article is good, therefore useful in the time of the various matrix materials for take semiconductor-encapsulating material, prepreg as representative, tackiness agent, coating etc.
Embodiment
Epoxy resin composition of the present invention comprises and contains following epoxy resin (A) and contain following epoxy resin (B) and/or the mixture of following epoxy resin (C).First be, phenolic compound (a)~(c) describe to the precursor of each epoxy resin (A)~(C).
More than one in the compound that phenolic compound (a) represents by following formula (1)~(5) obtain with the reacting of compound that following formula (6) represents.
In formula (1), R
1exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro or the carbonatoms 1~10 of carbonatoms 6~10, l represents R
1number, be 1~4 integer.
In formula (1), R
1exist independently of one another, be preferably the alkoxyl group of alkyl, hydroxyl or the carbonatoms 1~10 of hydrogen atom, carbonatoms 1~10, the particularly preferably alkoxyl group of hydrogen atom, carbonatoms 1~3.
As the concrete example of compound that the formula of reacting (1) for the compound that represents with formula (6) represents in order to obtain phenolic compound (a), can enumerate: 2-hydroxy acetophenone, 3-hydroxy acetophenone, 4-hydroxyacetophenone, 2 ', 4 '-resacetophenone, 2 ', 5 '-resacetophenone, 3 ', 4 '-resacetophenone, 3 ', 5 '-resacetophenone, 2 ', 3 ', 4 '-trihydroxy-acetophenone, 2 ', 4 ', 6 '-trihydroxy-acetophenone monohydrate, 4 '-hydroxyl-3 '-methyl acetophenone, 4 '-hydroxyl-2 '-methyl acetophenone, 2 '-hydroxyl-5 '-methyl acetophenone, 4 '-hydroxyl-3 '-methoxyacetophenone, 2 '-hydroxyl-4 '-methoxyacetophenone, 4 '-hydroxyl-3 '-nitro-acetophenone, 4 '-hydroxyl-3 ', 5 '-dimethoxy-acetophenone, 4 ', 6 '-dimethoxy-2 '-hydroxy acetophenone, 2 '-hydroxyl-3 ', 4 '-dimethoxy-acetophenone, 2 '-hydroxyl-4 ', 5 '-dimethoxy-acetophenone, 5-acetylsalicylic acid methyl esters, 2 ', 3 '-dihydroxyl-4 '-methoxyacetophenone hydrate.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferred 4 '-hydroxyl-3 '-methyl acetophenone, 4 '-hydroxy acetophenone.
In formula (2), R
2there is independently of one another any one in alkoxyl group, morpholinyl carbonyl, phthalimide-based, piperonyl or the hydroxyl of the alkyl-carbonyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~15, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10.
As the concrete example of compound that the formula of reacting (2) for the compound that represents with formula (6) represents in order to obtain phenolic compound (a), can enumerate: acetone, 1,3-phenylbenzene-2-acetone, 2-butanone, 1-phenyl-1,3-dimethyl diketone, 2 pentanone, propione, 4-methyl-2 pentanone, methyl ethyl diketone, methyl-n-butyl ketone, 3-hexanone, isopentyl methyl ketone, ethyl isobutyl ketone, 4-methyl-methyl-n-butyl ketone, 2,5-hexanedione, 1,6-phenylbenzene-1,6-hexanedione, 2-heptanone, 3-heptanone, dipropyl ketone, 2-methyl-dipropyl ketone, 5-methyl-3-heptanone, 6-methyl-2-heptanone, valerone, methyln-hexyl ketone, 3-octanone, 4-octanone, 5-methyl-methyln-hexyl ketone, methyl n-heptyl ketone, 3-nonanone, 4-nonanone, butyl ketone, 2-decanone, 3-decanone, propyl hexyl ketone, 5-decanone, 2-undecyl ketone, 3-undecyl ketone, 4-undecyl ketone, 5-undecyl ketone, 6-undecyl ketone, 2-methyl-4-undecyl ketone, 2-ten diketone, 3-ten diketone, 4-ten diketone, 5-ten diketone, 6-ten diketone, 2-ten tetraketones, 3-ten tetraketones, 8-15 ketone, 10-19 ketone, 7-ten triketones, 2-15 ketone, 3-16 ketone, pelargone, 11-bis-undecyl ketones, 12-tricosanone, 14-bis-margarones, palmitone, 18-pentatriacontanone, 4-oxyethyl group-2-butanone, 4-(4-p-methoxy-phenyl)-2-butanone, 4-methoxyl group-4-methyl-2 pentanone, 4-anisole benzylacetone, methoxy acetone, phenoxy acetone, methyl acetoacetate, methyl aceto acetate, propyl acetoacetate, butyl-acetoacetate, isobutyl acetoacetate, the secondary butyl ester of etheric acid, tert-butyl acetoacetate, etheric acid 3-pentyl ester, etheric acid pentyl ester, isoamyl acetoacetate, the own ester of etheric acid, etheric acid heptyl ester, etheric acid n-octyl, benzyl acetoacetate, ethanoyl Succinic acid dimethylester, acetone dimethyl malonate, acetone diethyl malonate, acetyl-acetic acid 2-methoxy-ethyl ester, acetoacetic acid allyl ester, 4-sec-butoxy-2-butanone, benzyl butyl ketone, Bisdemethoxycurcumin, 1,1-dimethoxy-3-butanone, 1,3-diacetoxy acetone, 4-medical midbodies of para (ortho)-hydroxybenzoic acetone, 4-(4-hydroxy phenyl)-2-butanone, isopentyl methyl ketone, 4-hydroxy-2-butanone, 5-hexene-2-ketone, acetonyl-acetone, 3,4-dimethoxy-phenyl acetone, piperonyl methyl ketone, piperonylacetone, phthalimide-based acetone, 4-isopropoxy-2-butanone, 4-isobutoxy-2-butanone, acetoxyl group-2-acetone, N-acetoacetyl morpholine, 1-ethanoyl-4-piperidone etc.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferred acetone.
In formula (3), R
3exist independently of one another, any one in alkoxyl group or the hydroxyl of the aryl of the alkyl-carbonyl of expression hydrogen atom, carbonatoms 0~10, the alkyl of carbonatoms 1~10, carbonatoms 6~10, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10, n represents carbonatoms, represent any one integer in 0,1,2, m represents R
3number, meet the relation of 1≤m≤n+2.
In addition, in formula (3), R
3during for the replacement of carbonatoms 0 or unsubstituted alkyl-carbonyl, representing to comprise the main framing that forms general formula (3) is the carbonyl structure of the carbon atom of naphthenic hydrocarbon, for example can enumerate: 1,3-cyclopentanedione etc.
As the concrete example of compound that the formula of reacting (3) for the compound that represents with formula (6) represents in order to obtain phenolic compound (a), can enumerate: cyclopentanone, 3-benzyl ring pentanone, 2-ethanoyl cyclopentanone, 1,3-cyclopentanedione, 2-methyl isophthalic acid, 3-cyclopentanedione, 2-ethyl-1,3-cyclopentanedione, pimelinketone, 3-methylcyclohexanone, 4-methylcyclohexanone, 4-ethyl cyclohexanone, 4-tertiary butyl pimelinketone, 4-amyl group pimelinketone, 3-benzyl ring hexanone, 4-benzyl ring hexanone, 3,3-dimethylcyclohexanon, 3,4-dimethylcyclohexanon, 3,5-dimethylcyclohexanon, 4,4-dimethylcyclohexanon, 3,3,5-trimethylcyclohexanone, 2-acetyl cyclohexanone, 4-pimelinketone ethyl formate, Isosorbide-5-Nitrae-cyclohexanedione monoethylene acetal, connection hexanaphthene-4,4 '-diketone monoethylene glycol ketal, Isosorbide-5-Nitrae-cyclohexanedione list-2,2-dimethyl trimethylene ketal, 2-ethanoyl-5,5-dimethyl-hydroresorcinol, 1,2-cyclohexanedione, hydroresorcinol, Isosorbide-5-Nitrae-cyclohexanedione, 2-methyl isophthalic acid, hydroresorcinol, 5-methyl isophthalic acid, hydroresorcinol, methone, Isosorbide-5-Nitrae-cyclohexanedione-2,5-dioctyl phthalate dimethyl ester, 4,4 '-Lian pimelinketone, two (the 4-oxo cyclohexyl) propane of 2,2-, suberone etc.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferably cyclopentanone, pimelinketone, suberone, 4-methylcyclohexanone.
In formula (4), R
4there is independently of one another any one in alkoxyl group or the hydroxyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10.
In formula (4), R
4exist independently of one another, be preferably the unsubstituted alkyl of hydrogen atom, carbonatoms 1~20, the unsubstituted aryl of carbonatoms 6~10, unsubstituted alkoxyl group or the hydroxyl of carbonatoms 1~10.
As the concrete example of compound that the formula of reacting (4) for the compound that represents with formula (6) represents in order to obtain phenolic compound (a), can enumerate: biacetyl, 2,3-diacetylmethane, 3,4-hexanedione, 5-methyl-2,3-hexanedione, 2,3-heptanedione etc.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferred biacetyl.
In formula (5), R
5exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10, alkyl ester group or the hydroxyl of carbonatoms 1~10, in addition, the integer that m is 1~10.
In formula (5), R
5exist independently of one another, be preferably the alkyl of hydrogen atom, carbonatoms 1~20, alkoxyl group or the hydroxyl of carbonatoms 1~10.
As the concrete example of compound that the formula of reacting (5) for the compound that represents with formula (6) represents in order to obtain phenolic compound (a); can enumerate: ethyl-diacetyl-acetate, 2; 5-hexanedione, 3-methyl-2; 4-diacetylmethane, 3-ethyl-2; 4-diacetylmethane, 3-butyl-2; 4-diacetylmethane, 3-phenyl-2,4-diacetylmethane, 4-ethanoyl-5-oxo ethyl hexanoate etc.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferred 3-methyl-2,4-diacetylmethane, 3-ethyl-2,4-diacetylmethane.
In formula (6), R
6exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro, formyl radical, allyl group or the carbonatoms 1~10 of carbonatoms 6~10, k represents R
6number, be 1~4 integer.
In above formula (6), R
6exist independently of one another, be preferably the alkoxyl group of carbonatoms 1~3.
As in order to obtain phenolic compound (a) for the concrete example of compound representing with more than one the formula of reacting (6) that is selected from compound that formula (1)~(5) represent, can enumerate: Benzaldehyde,2-hydroxy, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, 2,3-Dihydroxy benzaldehyde, 2,4-Dihydroxy benzaldehyde, 2,5-Dihydroxy benzaldehyde, 3,4-Dihydroxy benzaldehyde, syringic aldehyde, DTHB, isovanillin, 4-hydroxyl-3-nitrobenzaldehyde, 5-hydroxyl-2-nitrobenzaldehyde, 3,4-dihydroxyl-5-nitrobenzaldehyde, Vanillin, o-vanillin, 2-hydroxyl-1-naphthalene Formaldehyde, 2-hydroxyl-5-nitro meta-anisaldehyde 99, 2-hydroxy-5-methyl base m-terephthal aldehyde, 2-hydroxyl-4-methoxybenzaldehyde, 1-hydroxyl-2-naphthaldehyde, 2-hydroxy-5-methyl oxygen benzaldehyde, 5-nitro Vanillin, 5-allyl group-3-methoxysalicyl aldehyde, 3,5-di-tert-butyl salicylaldehyde, 3-oxyethyl group salicylic aldehyde, 4-hydroxyl m-terephthal aldehyde, 4-hydroxyl-3,5-dimethylbenzaldehyde, 2,4,6-tri hydroxybenzaldehyde, 2,4,5-tri hydroxybenzaldehyde, 2,3,4-tri hydroxybenzaldehyde, 3,4,5-tri hydroxybenzaldehyde, vanirom etc.These materials can only use one, also can be used in combination.Wherein, because the solvent solubility when by obtained phenolic compound epoxidation is high and the cured article of composition epoxy resin shows high thermal conductivity, therefore preferably use separately Vanillin.
Phenolic compound (a) can carry out aldol reaction with the compound of formula (6) expression by more than one that make compound that formula (1)~(5) represent under acidic conditions or under alkaline condition and obtain.
The compound representing for formula (6), 1 mole of the compound representing with respect to formula (1) preferably uses 1.0~1.05 moles, preferably 2.0~3.15 moles of the uses of 1 mole of the compound that represents with respect to formula (2), formula (3), formula (4) and formula (5).
Carry out aldol reaction under acidic conditions time, as operable an acidic catalyst, can enumerate: the mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, the organic acids such as toluenesulphonic acids, xylene monosulfonic acid, oxalic acid.These catalyzer can use separately, also can use by multiple combination.1 mole of the compound that the usage quantity of an acidic catalyst represents with respect to formula (6) is preferably 0.01~1.0 mole, more preferably 0.2~0.5 mole.
On the other hand, carry out aldol reaction under alkaline condition time, as operable basic catalyst, can enumerate: the metal hydroxidess such as sodium hydroxide and potassium hydroxide, the carbonic acid such as salt of wormwood and sodium carbonate an alkali metal salt, the sulfonamide derivativess such as diethylamine, triethylamine, Tributylamine, tri-isobutylamine, pyridine and piperidines, and the aminoalcohol derivative such as dimethylaminoethanol and DEAE diethylaminoethanol.The in the situation that of alkaline condition, the basic catalyst of enumerating above can use separately, also can use by multiple combination.1 mole of the compound that the usage quantity of basic catalyst represents with respect to formula (6) is preferably 0.1~2.5 mole, more preferably 0.2~2.0 mole.
Obtaining in the reaction of phenolic compound (a), can use as required solvent.As operable solvent, there is reactive solvent with the compound of formula (6) expression like this and be not particularly limited so long as not resembling ketone for example, the viewpoint of the compound dissolution representing from the formula (6) easily making as raw material is considered, preferably uses alcohols as solvent.
Temperature of reaction is generally 10~90 ℃, preferably 35~70 ℃.Reaction times is generally 0.5~10 hour, still, due to according to the kind of starting compound and to some extent difference of reactivity, is therefore not limited to this.After reaction finishes, while taking-up with the form of resin, reaction product is removed to unreacted reactant, solvent etc. after washing or under the condition of not washing under heating decompression from reaction solution.While taking-up with the form of crystallization, by reaction solution being dripped in a large amount of water and crystallization.While reaction under alkaline condition, the phenolic compound of the present invention of generation may be dissolved in water, therefore by adding hydrochloric acid etc. to be adjusted to neutrality~acidic conditions, its form with crystallization is separated out.
Phenolic compound (b) is represented by following formula (7):
In formula (7), R
7, X and Y exist independently of one another, represents any one in the alkoxyl group of alkyl or aryl, hydroxyl or carbonatoms 1~10 of hydrogen atom, carbonatoms 1~10, k represents R
7number, represent 1~4 integer.
In formula (7), consider R from the viewpoint that can keep high heat conductance
7, X and Y exist independently of one another, is preferably the alkyl of hydrogen atom, carbonatoms 1~3.
As phenolic compound (b), can enumerate various bisphenols.Can enumerate particularly: BPF, BPA, BPE, Methylene bis-p-CR, TM-BPF, Bis-C, Bis P-MIBK, Bis26X-A, Bis P-AP, Bis OPP-A, Ultrite P, DHBP, Bis OC-F, Bis P-B, Bis P-IBTD, Bis-BA, Bis P-IOTD, Bis OIPP-A, Bis P-DED, Bis OSBP-A, Bis OTBP-A, Bis2M6B-IBTD, Bis OCHP-A, Ph-CC-AP (being Honshu chemical industry manufacture) etc.
Wherein, consider from the viewpoint that can keep high heat conductance, preferably BPF, BPA, particularly preferably BPF.
Phenolic compound (c) is represented by following formula (8):
In formula (8), R
8exist independently of one another, any one in the alkoxyl group of alkyl or aryl, hydroxyl or the carbonatoms 1~10 of expression hydrogen atom, carbonatoms 1~10, l represents R
8number, represent 1~4 integer, A represents direct key or has the alkylidene of the carbonatoms 5~15 of cyclic rings.
As phenolic compound (c), except the xenol, 3 of the position of the A biphenyl backbone that is direct key, 3 ', 5,5 '-tetramethyl--4, beyond 4 '-diphenol compound, can also enumerate separately that suitable annular aliphatic ketone reacts with phenols and the phenolic compound that obtains.
As concrete compound, the compound shown in can being listed below.
Aforementioned phenolic compound can obtain commercially available product, for example can enumerate: Bis P-CP, Bis P-Z, Bis P-TMC, Bis OC-TMC, Bis P-MZ, Bis P-3MZ, Bis P-IPZ, Bis CR-IPZ, Bis26X-IPZ, Bis P-TCD, Bis OC-CDE, Bis26X-CDE, Bis P-CHEP, Bis P-COCT, Bis P-CPeDE (being Honshu chemical industry manufacture), TCDBP (METROPORITAN EXIMCHEM XTD) etc.
Below, epoxy resin composition of the present invention is described.
Epoxy resin composition of the present invention, by reacting above-mentioned each phenolic compound, epoxidation obtains with epihalohydrins.In addition, when epoxidation, can make epihalohydrins react with each phenolic compound (a)~(c) in advance and obtain epoxy resin (A)~(C), and each epoxy resin is obtained by mixing.As the method that epihalohydrins is reacted with each phenolic compound, as long as known method can be used without particular limitation, can use particularly the method for recording in for example Japanese kokai publication hei 05-155978 communique, TOHKEMY 2008-179739 communique.
But the viewpoint from manufacturing considers, preferably make the mixture reaction of epihalohydrins and phenolic compound (a)~(c) and obtain epoxy resin composition.By adopting this manufacture method, can obtain the mixture of epoxy resin (A)~(C), and also produce the epoxy resin that the skeleton of a part of each phenolic compound (a)~(c) connects by the glycidyl of open loop.
As epoxy resin composition of the present invention, particularly due to the cured article that obtains showing low melting viscosity and thering is high heat conductance, therefore, preferably contain the reacting of compound of compound and formula (3) expression representing as through type (6) and the epoxy resin (A) of the epoxide of the phenolic compound (a) that obtains and contain epoxy resin (B) and/or the mixture of epoxy resin (C).
Below, describe for the method that obtains epoxy resin composition by the mixture reaction that makes epihalohydrins and phenolic compound (a)~(c).
The amount sum of phenolic compound (b) and phenolic compound (c) shared ratio in the total amount of phenolic compound (a)~(c) is preferably 1~30 quality %, further preferred 5~30 quality %.The ratio of the amount sum of phenolic compound (b) and phenolic compound (c) is if below 30 quality %, and heat conductivity can not reduce, and more than 1 quality %, viscosity can not improve if, can not reduce the adhesivity of metal, therefore preferred.
Obtaining in the reaction of the epoxy resin containing in epoxy resin composition of the present invention, can use Epicholorohydrin, Alpha-Methyl Epicholorohydrin, Beta-methyl Epicholorohydrin, epibromohydrin etc. as epihalohydrins, the facile Epicholorohydrin of preferred industrial appearance.The usage quantity of epihalohydrins is generally 2~20 moles with respect to 1 mole of the hydroxyl of phenolic compound, and preferably 2~15 moles, particularly preferably 2~6.5 moles.Epoxy resin (A) by carrying out addition by phenolic compound and epihalohydrins under the existence of alkalimetal oxide, and then, by 1 of generation, 2-halohydrin ether closed loop is carried out epoxidised reaction and obtains.Now, by use epihalohydrins than conventionally significantly low amount as mentioned above, can increase molecular weight and the expansion molecular weight distribution of epoxy resin.As a result, the epoxy resin obtaining takes out from system with the form of the arborescens thing with lower softening temperature, shows good solvent solubility.
As operable alkali metal hydroxide in epoxidation reaction, can enumerate sodium hydroxide, potassium hydroxide etc., these oxyhydroxide can directly use solid substance, or also can use its aqueous solution.While using the aqueous solution, can be following method: the aqueous solution of this alkali metal hydroxide is added in reaction system continuously, and from the mixed solution of the water that distillates continuously and epihalohydrins, remove and anhydrate by separatory under reduced pressure or under normal pressure, only epihalohydrins is turned back in reaction system continuously.The usage quantity of alkali metal hydroxide is generally 0.9~3.0 mole with respect to 1 mole of the hydroxyl of phenolic compound, and preferably 1.0~2.5 moles, more preferably 1.0~2.0 moles, particularly preferably 1.0~1.3 moles.
In addition, the inventor finds, uses laminar sodium hydroxide by special in epoxidation reaction, with use aqueous solution form sodium hydroxide time compared with, can reduce significantly halogen quantity contained in obtained epoxy resin.This halogen derives from epihalohydrins, sneaks into manyly in epoxy resin, more can cause the decline of the heat conductivity of cured article.In addition, the preferred portion-wise addition of this laminar sodium hydroxide is in reaction system.By carrying out portion-wise addition, can prevent the sharply reduction of temperature of reaction, can prevent thus as 1 of impurity, the generation of 3-halohydrin form or halogenated methylene form, can form the cured article that thermal conductivity is higher.
In order to promote epoxidation reaction, preferably add the quaternary ammonium salts such as tetramethyl ammonium chloride, 4 bromide, trimethyl benzyl ammonia chloride as catalyzer.The usage quantity of quaternary ammonium salt is generally 0.1~15g, preferably 0.2~10g with respect to 1 mole of the hydroxyl of phenolic compound of the present invention.
In addition, when epoxidation, adding that alcohols, dimethyl sulfone, methyl-sulphoxide, tetrahydrofuran (THF), the dioxane isopolarity aprotic solvent etc. such as methyl alcohol, ethanol, Virahol react in reaction is preferred aspect carrying out.Wherein, preferred alcohols or methyl-sulphoxide.While using alcohols, can obtain epoxy resin with high yield.On the other hand, while using methyl-sulphoxide, can further reduce the halogen quantity in epoxy resin.
While using above-mentioned alcohols, its usage quantity is generally 2~50 quality % with respect to the usage quantity of epihalohydrins, preferably 4~35 quality %.In addition, while using polar aprotic solvent, be generally 5~100 quality % with respect to the usage quantity of epihalohydrins, preferably 10~80 quality %.
Temperature of reaction is generally 30~90 ℃, preferably 35~80 ℃.Reaction times is generally 0.5~10 hour, preferably 1~8 hour.
After reaction finishes, will after reaction product washing or under the condition of not washing, under heating decompression, from reaction solution, remove epihalohydrins, solvent etc.In addition, in order further to reduce contained halogen quantity in the epoxy resin obtaining, the epoxy resin composition of the present invention reclaiming is dissolved in toluene, methyl iso-butyl ketone (MIBK) equal solvent, and the aqueous solution that adds the alkali metal hydroxide such as sodium hydroxide, potassium hydroxide reacts, closed loop reliably.Now, the usage quantity of alkali metal hydroxide is generally 0.01~0.3 mole, preferably 0.05~0.2 mole with respect to 1 mole of the hydroxyl of phenolic compound of the present invention.Temperature of reaction is generally 50~120 ℃, and the reaction times is generally 0.5~2 hour.
After reaction finishes, remove the salt of generation by filtration, washing etc., then distillation, except desolventizing, obtains epoxy resin composition of the present invention thus under heating decompression.In addition, when epoxy resin composition of the present invention is separated out with crystallized form, the salt of generation can be dissolved in after a large amount of water, filter the crystallization of collecting epoxy resin composition.
As mentioned above, use total halogen quantity of the epoxy resin composition of the present invention that laminar sodium hydroxide obtains to be generally below 1800ppm, preferably below 1600ppm, further preferably below 700ppm.When total halogen quantity is too much, except the electric reliability of cured article is had a negative impact, also residual as uncrosslinked end, when molten state while therefore solidifying, do not carry out the orientation between molecule, cause heat conductivity to decline.
The epoxy equivalent (weight) of epoxy resin composition of the present invention, considers from the viewpoint that obtains low-viscosity epoxy resin compound, preferably below 350g/eq., particularly preferably below 300g/eq..In addition, the epoxy equivalent (weight) of epoxy resin composition of the present invention refers to the mean value of the epoxy equivalent (weight) of the each epoxy resin containing in obtained epoxy resin composition.
Below, composition epoxy resin of the present invention is described.Composition epoxy resin of the present invention contains epoxy resin composition of the present invention as neccessary composition.
In composition epoxy resin of the present invention, epoxy resin composition of the present invention can be used in combination with other epoxy resin.
As the concrete example of other epoxy resin, can enumerate: phenols (phenol, the phenol that alkyl replaces, the phenol that aromatic series replaces, naphthols, the naphthols that alkyl replaces, dihydroxy-benzene, dihydroxy-benzene and dihydroxy naphthlene etc. that alkyl replaces) and various aldehyde (formaldehyde, acetaldehyde, alkyl aldehydes, phenyl aldehyde, the phenyl aldehyde that alkyl replaces, hydroxy benzaldehyde, naphthaldehyde, glutaraldehyde, o-phthalaldehyde(OPA), crotonic aldehyde and phenylacrolein etc.) polycondensate, the polycondensate of the aromatics such as dimethylbenzene and formaldehyde and the polycondensate of phenols, phenols and various diolefin (dicyclopentadiene, terpenes, vinyl cyclohexene, norbornadiene, vinyl norbornene, tetrahydroindene, Vinylstyrene, divinyl biphenyl, diisopropenyl biphenyl, divinyl and isoprene etc.) polycondensate, phenols and ketone (acetone, methylethylketone, methyl iso-butyl ketone (MIBK), methyl phenyl ketone and benzophenone etc.) polycondensate, the polycondensate of phenols and aromatic series diformazan alcohols (xylyl alcohol and biphenyl dimethanol etc.), the polycondensate of phenols and aromatic series dichloromethane base class (α, α '-xylene dichloride and dichloride methyl biphenyl etc.), phenols and aromatic series bis-alkoxy methyl class (bi-methoxy methylbenzene, bi-methoxy methyl diphenyl and two phenoxymethyl biphenyl etc.) polycondensate, the polycondensate of bisphenols and various aldehyde, and the glycidyl ether based epoxy resin that the glycidyls such as alcohols are obtained, alicyclic epoxy resin, Racemic glycidol amine epoxy resin, glycidyl ester based epoxy resins etc., as long as normally used epoxy resin is not limited to this.These materials can only use one also can be used in combination.
In the situation that being used in combination other epoxy resin, more than in whole epoxy resin compositions of epoxy resin composition of the present invention in composition epoxy resin of the present invention, shared ratio is preferably 30 quality %, more preferably more than 40 quality %, further preferably more than 70 quality %, particularly preferably 100 quality % (not being used in combination the situation of other epoxy resin).But, in the situation that the properties-correcting agent using epoxy resin composition of the present invention as composition epoxy resin uses, add with the ratio that reaches 1~30 quality % in whole epoxy resin.
As the solidifying agent containing in composition epoxy resin of the present invention, can enumerate such as aminated compounds, anhydrides compound, amides and phenolic compound etc.The object lesson of these solidifying agent is as shown in following (a)~(e).
(a) aminated compounds
Diaminodiphenyl-methane, diethylenetriamine, Triethylenetetramine (TETA), diaminodiphenylsulfone(DDS), isophorone diamine and naphthylene diamine etc.
(b) anhydrides compound
Tetra hydro Phthalic anhydride, trimellitic acid 1,2-anhydride, pyromellitic acid acid anhydride, maleic anhydride, Tetra Hydro Phthalic Anhydride, methyl tetrahydrophthalic anhydride, methyl carbic anhydride, hexahydrophthalic anhydride and methylhexahydrophthalic anhydride etc.
(c) amides
Dyhard RU 100 or by linolenic dipolymer and the synthetic polyimide resin of quadrol etc.
(d) phenolic compound
Polyatomic phenol (dihydroxyphenyl propane, Bisphenol F, bisphenol S, fluorenes bis-phenol, terpene diphenol, 4,4 '-dihydroxybiphenyl, 2,2 '-dihydroxybiphenyl, 3,3 ', 5,5 '-tetramethyl--(1,1 '-biphenyl)-4,4 '-glycol, Resorcinol, Resorcinol, naphthalenediol, three (4-hydroxy phenyl) methane and 1,1,2,2-tetra-(4-hydroxy phenyl) ethane etc.); The phenol resins that phenols (naphthols, dihydroxy-benzene and dihydroxy naphthlene etc. that phenol, naphthols, the alkyl that for example, phenol, alkyl replace replaces) obtains with the condensation of aldehydes (formaldehyde, acetaldehyde, phenyl aldehyde, p-Hydroxybenzaldehyde, salicylaldhyde and furfural etc.), ketone (parahydroxyacet-ophenone and o-hydroxyacetophenone etc.) or dienes (dicyclopentadiene and three polycyclopentadienes etc.); The biphenyl class (4 of above-mentioned phenols and replacement, 4 '-bis-(chloromethyl)-1,1 '-biphenyl and 4,4 '-bis-(methoxymethyl)-1,1 '-biphenyl etc.) or replace phenyl class (1, two (chloromethyl) benzene of 4-, Isosorbide-5-Nitrae-bis-(methoxymethyl) benzene and Isosorbide-5-Nitrae-bis-(hydroxymethyl) benzene etc.) etc. polycondensation and the phenol resins that obtains; The modifier of above-mentioned phenols and/or above-mentioned phenol resins; The halogenation phenols such as tetrabromo-bisphenol and brominated phenols resin.
(e) other imidazoles, BF
3-amine complex, guanidine derivative.
In these solidifying agent, the condenses of the aminated compoundss such as preferred diaminodiphenyl-methane, diaminodiphenylsulfone(DDS) and naphthylene diamine and catechol and aldehydes, ketone, dienes, the biphenyl class of replacement or the phenols of replacement etc. has the solidifying agent of the structure of active hydrogen base adjacency, in addition, as one of composition of the present invention be the arrangement that the phenolic compound (a) of the precursor of epoxy resin (A) contributes to epoxy resin, therefore preferred.
In composition epoxy resin of the present invention, the usage quantity of solidifying agent is preferably 0.8~1.2 equivalent with respect to epoxy group(ing) 1 equivalent of epoxy resin, and particularly preferably 0.95~1.05.
Composition epoxy resin of the present invention can contain the good inorganic filling material of thermal conduction as required, can give thus its cured article better high thermal conductivity.
The inorganic filling material that composition epoxy resin of the present invention is contained, add for the object of the cured article of composition epoxy resin being given to higher thermal conductivity, therefore, in the case of the thermal conductivity of inorganic filling material itself is too low, the high heat conductance obtaining by the combination of epoxy resin and solidifying agent is likely impaired.Therefore, as the contained inorganic filling material of composition epoxy resin of the present invention, the preferably high inorganic filling material of thermal conductivity, as long as having, 20W/mK is above, preferred above, the more preferably inorganic filling material of thermal conductivity more than 50W/mK of 30W/mK conventionally, without any restriction.In addition, in this said thermal conductivity, be the value of measuring according to the method for ASTM E1530.As the object lesson of inorganic filling material with such characteristic, can enumerate: the inorganic powder packing materials such as boron nitride, aluminium nitride, silicon nitride, silicon carbide, titanium nitride, zinc oxide, wolfram varbide, aluminum oxide, magnesium oxide, the cellulosic such as synthon, ceramic fiber packing material, tinting material etc.The shape of these inorganic filling materials can be any one shapes such as powder (block, spherical), ultimate fibre, macrofiber, particularly flat shape if, by the stacked effect of inorganic filling material self, the heat conductivity of cured article is higher, the thermal diffusivity of cured article further improves,, therefore preferred.
The usage quantity of inorganic filling material in composition epoxy resin of the present invention, be generally 2~1000 mass parts with respect to resinous principle 100 mass parts in composition epoxy resin, in order to improve as much as possible thermal conductivity, the operation in the concrete purposes of composition epoxy resin of the present invention etc. not being caused in the scope of obstacle, preferably increase as much as possible the usage quantity of inorganic filling material.These inorganic filling materials can only use one, also can be used in combination.
In addition, can be using in the thermal conductivity of packing material entirety remains scope more than 20W/mK, also can be that more than 20W/mK inorganic filling material is used in combination lower than the packing material of 20W/mK and thermal conductivity by thermal conductivity, for the object of the present invention of cured article that obtains high as far as possible thermal conductivity, thermal conductivity should be limited to bottom line lower than the use of the packing material of 20W/mK.Kind, the shape of the packing material that can be used in combination are not particularly limited.
Composition epoxy resin of the present invention is in the situation of encapsulating semiconductor purposes, consider from viewpoints such as the thermotolerance of cured article, wet fastness, mechanical properties, preferably use the inorganic filling material of thermal conductivity more than 20W/mK to account for the ratio of 75~93 quality % in composition epoxy resin.Now, all the other are epoxy resin composition, curing agent component and other additive adding as required, as additive, are other inorganic filling material that can be used in combination, curing catalyst described later etc.
In composition epoxy resin of the present invention, can contain curing catalyst.As the curing catalyst that can use, for example can enumerate: the imidazoles such as glyoxal ethyline, 2-ethyl imidazol(e), 2-phenylimidazole and 2-ethyl-4-methylimidazole, 2-(dimethylamino methyl) phenol, triethylenediamine, trolamine and 1, the tertiary amines such as 8-diazabicyclo (5.4.0) 11 carbon-7-alkene, the organic phosphine classes such as triphenylphosphine, diphenylphosphine and tributylphosphine, the metallic compounds such as stannous octoate, tetraphenyl
tetraphenyl borate and tetraphenyl
ethyl triphenyl borates etc. are quaternary
the tetraphenyl borates such as quaternary borate, 2-ethyl-4-methylimidazole tetraphenyl borate and N-methylmorpholine tetraphenyl borate etc.Curing catalyst uses 0.01~15 mass parts as required with respect to epoxy resin 100 mass parts.
In composition epoxy resin of the present invention, can add as required the various Synergist S-421 95s such as silane coupling agent, releasing agent and pigment, various thermosetting resin and various thermoplastic resins etc.As the concrete example of thermosetting resin and thermoplastic resin, can enumerate vinylester resin, unsaturated polyester resin, maleimide resin, cyanate ester resin, isocyanate compound, benzo
the modifier of piperazine compound, vinyl benzyl ether compound, polyhutadiene and modifier thereof, acrylonitrile copolymer, indene resin, fluorine resin, polyorganosiloxane resin, polyetherimide, polyethersulfone, polyphenylene oxide, polyacetal, polystyrene, polyethylene, dicyclopentadiene resin etc.Thermosetting resin or thermoplastic resin use with the amount accounting in composition epoxy resin of the present invention below 60 quality %.
Composition epoxy resin of the present invention, can be by above-mentioned each composition is mixed to obtain equably, and its preferable use can be enumerated semiconductor-encapsulating material, printed wiring board etc.
Composition epoxy resin of the present invention can easily obtain its cured article by the method same with existing known method.For example, using the epoxy resin as the neccessary composition of composition epoxy resin of the present invention, solidifying agent and thermal conductivity are inorganic filling material more than 20W/mK, and curing catalyst as required, Synergist S-421 95, forcing machine for various thermosetting resins or various thermoplastic resins etc., kneader, cylinders etc. are fully mixed into and evenly obtain composition epoxy resin of the present invention, then, this composition epoxy resin is passed through to melt casting method, transfer molding method, the moulding such as blow molding method or compressed moulding method, then more than fusing point heat at it 2~10 hours, can obtain thus the cured article of composition epoxy resin of the present invention.By semiconductor element encapsulation lead frame etc. above being carried with aforesaid method, can be by composition epoxy resin of the present invention for encapsulating semiconductor purposes.
In addition, composition epoxy resin of the present invention can be made to the varnish that contains solvent.This varnish for example can be by least containing epoxy resin composition of the present invention, and containing as required thermal conductivity is mixture and the toluene of other compositions such as inorganic filling material more than 20W/mK, dimethylbenzene, acetone, methylethylketone, methyl iso-butyl ketone (MIBK), pimelinketone, cyclopentanone, N, N '-dimethyl formamide, N, N '-N,N-DIMETHYLACETAMIDE, methyl-sulphoxide, N-Methyl pyrrolidone, glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dme, dipropylene glycol diethyl ether, TRIGLYME, the glycol ethers such as triethylene glycol diethyl ether, ethyl acetate, butylacetate, methylcellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, Trivalin SF acetic ester, propylene glycol methyl ether acetate, pentanedioic acid dialkyl, succsinic acid dialkyl, the ester classes such as hexanodioic acid dialkyl, the cyclic ester classes such as gamma-butyrolactone, sherwood oil, petroleum naphtha, the organic solvents such as the petroleum-type such as hydrogenated naphtha and solvent naphtha solvent are obtained by mixing.The amount of solvent is generally 10~95 quality % with respect to varnish entirety, preferably 15~85 quality %.
After the varnish that makes to obtain is in the above described manner infiltrated up in the fiber base materials such as glass fibre, carbon fiber, trevira, tynex, sapphire whisker and paper, by adding heat extraction solvent, and make composition epoxy resin of the present invention become semi-cured state, can obtain thus prepreg of the present invention.In addition, in this said " semi-cured state ", refer to a part of epoxy group(ing) unreacted as reactive functional groups and residual state.By hot-forming this prepreg, can obtain cured article.
Embodiment
Below, be described more specifically the present invention by embodiment, still, the invention is not restricted to these embodiment.In synthesis example, embodiment, comparative example, part refers to mass parts.
In addition, epoxy equivalent (weight), ICI viscosity, thermal conductivity are measured under the following conditions.
Epoxy equivalent (weight)
The method of recording by JIS K-7236 is measured, and unit is g/eq..
Melt viscosity
Based on the melt viscosity of 150 ℃ of cone-plate methods
Metering equipment: cone-plate (ICI) high temperature viscosimeter
(RESEACH EQUIPMENT (LONDON) LTD. manufacture)
Thermal conductivity
Measure according to the method for ASTM E1530, unit is W/mK.
Synthesis example 1
Having in the flask of agitator, reflux condensing tube, whipping appts, add 136 parts of 4 '-hydroxy acetophenones, 152 parts of Vanillins and 200 parts of ethanol and dissolve.After adding therein 20 parts, 97 quality % sulfuric acid, be warmed up to 60 ℃, at this temperature, react 10 hours, then reaction solution is injected in 1200 parts, water and carries out crystallization.Leach after crystallization, 600 parts of washed twice of water, carry out vacuum-drying afterwards, obtain the phenolic compound 1 of 256 parts of yellow crystals.The endotherm peak temperature of measuring by DSC of the crystallization of gained is 233 ℃.
Synthesis example 2
Having in the flask of agitator, reflux condensing tube, whipping appts, add 166 parts of 4 '-hydroxyl-3 '-methoxyacetophenones, 122 parts of 4-hydroxy benzaldehydes and 200 parts of ethanol and dissolve.After adding therein 20 parts, 97% sulfuric acid, be warmed up to 50 ℃, at this temperature, react 10 hours, then reaction solution is injected in 1200 parts, water and carries out crystallization.Leach after crystallization, 600 parts of washed twice of water, carry out vacuum-drying afterwards, obtain the phenolic compound 2 of 285 parts of dark brown crystallizations.The endotherm peak temperature of measuring by DSC of the crystallization of gained is 193 ℃.
Synthesis example 3
Having in the flask of agitator, reflux condensing tube, whipping appts, add 56 parts of 4-methylcyclohexanones, 152 parts of Vanillins and 150 parts of ethanol and dissolve.After adding 10 parts, 97 quality % sulfuric acid, be warmed up to 50 ℃, at this temperature, react 10 hours, then add 25 parts of tripoly phosphate sodium STPPs, and stir 30 minutes.Then add after 500 parts of methyl iso-butyl ketone (MIBK), 200 parts of washed twice of water, utilize vaporizer distillation except desolventizing afterwards, obtain 304 parts of semisolid phenolic compound 3.
Synthesis example 4
Having in the flask of agitator, reflux condensing tube, whipping appts, add 29 parts, acetone, 152 parts of Vanillins and 300 parts of ethanol and dissolve.After adding therein 80 parts of 50 quality % aqueous sodium hydroxide solutions, be warmed up to 45 ℃, at this temperature, react 120 hours, then reaction solution is injected in 1.5N hydrochloric acid 800mL and carries out crystallization.Leach after crystallization, 600 parts of washed twice of water, carry out vacuum-drying afterwards, obtain the phenolic compound 4 of 165 parts of yellow crystals.The fusing point of the crystallization of gained is determined as 201 ℃ by DSC.
Embodiment 1
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add the phenolic compound that obtains in 80 parts of synthesis examples 11,20 part 4,4 '-xenol, 300 portions of Epicholorohydrins, 75 parts of methyl-sulphoxides (hereinafter referred to as DMSO), under agitation being warmed up to 70 ℃ dissolves, with 33 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 70 ℃, carry out reaction in 2.5 hours.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 290 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 9 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 130 parts of epoxy resin compositions 1.The epoxy equivalent (weight) of gained epoxy resin composition is 200g/eq., and melt viscosity is 0.03Pas.
Embodiment 2
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add the phenolic compound that obtains in 80 parts of synthesis examples 22,20 part 4,4 '-xenol, 300 portions of Epicholorohydrins, 75 parts of DMSO, under agitation being warmed up to 70 ℃ dissolves, with 33 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 70 ℃, carry out reaction in 2.5 hours.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 290 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 9 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 130 parts of epoxy resin compositions 2.The epoxy equivalent (weight) of gained epoxy resin composition is 201g/eq., and melt viscosity is 0.03Pas.
Embodiment 3
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add the phenolic compound that obtains in 80 parts of synthesis examples 33,20 part 4,4 '-xenol, 235 portions of Epicholorohydrins, 59 parts of DMSO, under agitation being warmed up to 45 ℃ dissolves, with 26 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 45 ℃, carry out reaction in 1.5 hours, be then warmed up to 70 ℃ and carry out reaction in 30 minutes.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 271 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 8 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 122 parts of epoxy resin compositions 3.The epoxy equivalent (weight) of gained epoxy resin composition is 235g/eq., and melt viscosity is 0.03Pas.
Embodiment 4
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add the phenolic compound that obtains in 80 parts of synthesis examples 44,20 part 4,4 '-xenol, 261 portions of Epicholorohydrins, 65 parts of DMSO, under agitation being warmed up to 45 ℃ dissolves, with 29 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 45 ℃, carry out reaction in 1.5 hours, be then warmed up to 70 ℃ and carry out reaction in 30 minutes.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 279 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 8 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 126 parts of epoxy resin compositions 4.The epoxy equivalent (weight) of gained epoxy resin composition is 220g/eq., and melt viscosity is 0.03Pas.
Embodiment 5
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add 1,10 parts of Bisphenol F of phenolic compound (BPF) of obtaining in 90 parts of synthesis examples 1,284 portions of Epicholorohydrins, 71 parts of methyl-sulphoxides (hereinafter referred to as DMSO), under agitation being warmed up to 70 ℃ dissolves, with 32 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 70 ℃, carry out reaction in 2.5 hours.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 286 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 9 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 128 parts of epoxy resin compositions 5.The epoxy equivalent (weight) of gained epoxy resin composition is 204g/eq., and melt viscosity is 0.03Pas.
Embodiment 6
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add 2, the 10 parts of BPF of phenolic compound that obtain in 90 parts of synthesis examples 2,284 portions of Epicholorohydrins, 71 parts of DMSO, under agitation being warmed up to 70 ℃ dissolves, with 32 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 70 ℃, carry out reaction in 2.5 hours.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 286 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 9 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 129 parts of epoxy resin compositions 6.The epoxy equivalent (weight) of gained epoxy resin composition is 205g/eq., and melt viscosity is 0.03Pas.
Embodiment 7
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add 3, the 10 parts of BPF of phenolic compound that obtain in 90 parts of synthesis examples 3,212 portions of Epicholorohydrins, 53 parts of DMSO, under agitation being warmed up to 45 ℃ dissolves, with 24 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 45 ℃, carry out reaction in 1.5 hours, be then warmed up to 70 ℃ and carry out reaction in 30 minutes.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 264 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 7 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 119 parts of epoxy resin compositions 7.The epoxy equivalent (weight) of gained epoxy resin composition is 250g/eq., and melt viscosity is 0.03Pas.
Embodiment 8
Having in the flask of agitator, reflux condensing tube, whipping appts, in carrying out nitrogen purging, add 4, the 10 parts of BPF of phenolic compound that obtain in 90 parts of synthesis examples 4,241 portions of Epicholorohydrins, 60 parts of DMSO, under agitation being warmed up to 45 ℃ dissolves, with 27 parts of laminar sodium hydroxide of 90 minutes portion-wise addition, then at 45 ℃, carry out reaction in 1.5 hours, be then warmed up to 70 ℃ and carry out reaction in 30 minutes.After reaction finishes, use rotatory evaporator distillation under 135 ℃, decompression to remove excessive Epicholorohydrin equal solvent.Residue is dissolved in 273 parts of MIBK, then washes except desalting.After washing, MIBK solution is warmed up to 70 ℃, under agitation add 7 part of 30% aqueous sodium hydroxide solution, carry out reaction in 1 hour, then wash until washing water are neutral, use rotatory evaporator distillation under 180 ℃, decompression to remove methyl iso-butyl ketone (MIBK) etc. obtained solution, obtain thus 123 parts of epoxy resin compositions 8.The epoxy equivalent (weight) of gained epoxy resin composition is 229g/eq., and melt viscosity is 0.03Pas.
Embodiment 9~24 and comparative example 1,2
With the ratio (part) of table 1 by various components matching, mixing and the compressing tablet with mixing roll, then be shaped and prepare resin molded body by transmission, at 160 ℃, heat 2 hours, at 180 ℃, heat 8 hours again, obtain thus composition epoxy resin of the present invention and relatively use the cured article of resin combination.The measurement result of the thermal conductivity of these cured articles is as shown in table 1.
Table 1
? | Embodiment 9 | Embodiment 10 | Embodiment 11 | Embodiment 12 | Embodiment 13 | Embodiment 14 | Embodiment 15 | Embodiment 16 |
The composition of title complex | ? | ? | ? | ? | ? | ? | ? | ? |
Epoxy resin composition 1 | 100 | ? | ? | ? | 100 | ? | ? | ? |
Epoxy resin composition 2 | ? | 100 | ? | ? | ? | 100 | ? | ? |
Epoxy resin composition 3 | ? | ? | 100 | ? | ? | ? | 100 | ? |
Epoxy resin composition 4 | ? | ? | ? | 100 | ? | ? | ? | 100 |
Solidifying agent 1 | ? | ? | ? | ? | 68 | ? | ? | ? |
Solidifying agent 2 | ? | ? | ? | ? | ? | 67 | ? | ? |
Solidifying agent 3 | ? | ? | ? | ? | ? | ? | 81 | ? |
Solidifying agent 4 | ? | ? | ? | ? | ? | ? | ? | 74 |
Solidifying agent 5 | 53 | 52 | 45 | 48 | ? | ? | ? | ? |
Curing catalyst | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
The physical property of cured article | ? | ? | ? | ? | ? | ? | ? | ? |
Thermal conductivity (W/mk) | 0.29 | 0.30 | 0.30 | 0.28 | 0.31 | 0.31 | 0.34 | 0.31 |
? | Embodiment 17 | Embodiment 18 | Embodiment 19 | Embodiment 20 | Embodiment 21 | Embodiment 22 | Embodiment 23 | Embodiment 24 | Comparative example 1 | Comparative example 2 |
The composition of title complex | ? | ? | ? | ? | ? | ? | ? | ? | ? | ? |
Epoxy resin composition 5 | 100 | ? | ? | ? | 100 | ? | ? | ? | ? | ? |
Epoxy resin composition 6 | ? | 100 | ? | ? | ? | 100 | ? | ? | ? | ? |
Epoxy resin composition 7 | ? | ? | 100 | ? | ? | ? | 100 | ? | ? | ? |
Epoxy resin composition 8 | ? | ? | ? | 100 | ? | ? | ? | 100 | ? | ? |
Epoxy resin 9 | ? | ? | ? | ? | ? | ? | ? | ? | 100 | ? |
Epoxy resin 10 | ? | ? | ? | ? | ? | ? | ? | ? | ? | 100 |
Solidifying agent 1 | ? | ? | ? | ? | 66 | ? | ? | ? | ? | ? |
Solidifying agent 2 | ? | ? | ? | ? | ? | 66 | ? | ? | ? | ? |
Solidifying agent 3 | ? | ? | ? | ? | ? | ? | 76 | ? | ? | ? |
Solidifying agent 4 | ? | ? | ? | ? | ? | ? | ? | 71 | ? | ? |
Solidifying agent 5 | 51 | 51 | 42 | 46 | ? | ? | ? | ? | 38 | 60 |
Curing catalyst | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
The physical property of cured article | ? | ? | ? | ? | ? | ? | ? | ? | ? | ? |
Thermal conductivity (W/mk) | 0.29 | 0.29 | 0.30 | 0.29 | 0.31 | 0.31 | 0.33 | 0.31 | 0.25 | 0.26 |
Epoxy resin 9: the epoxy resin (trade(brand)name: NC-3000, Japanese chemical drug manufacture, epoxy equivalent (weight) 276g/eq.) that following formula (9) represents
Epoxy resin 10: the biphenyl type epoxy resin (trade(brand)name: YL-6121H, japan epoxy resin manufacture, epoxy equivalent (weight) 175g/eq.) that the epoxy resin that mole following formula (10) and (11) represent such as contains
Solidifying agent 1: the phenolic compound 1 obtaining in synthesis example 1
Solidifying agent 2: the phenolic compound 2 obtaining in synthesis example 2
Solidifying agent 3: the phenolic compound 3 obtaining in synthesis example 3
Solidifying agent 4: the phenolic compound 4 obtaining in synthesis example 4
Solidifying agent 5: phenolic varnish that following formula (12) represents (trade(brand)name: H-1, bright and change into manufacture, hydroxyl equivalent 105g/eq.)
Curing catalyst: triphenylphosphine (northern emerging chemical industry manufacture)
Embodiment 25~40 and comparative example 3,4
With the ratio (part) of table 2 by various components matching, mixing and the compressing tablet with mixing roll, then be shaped and prepare resin molded body by transmission, at 160 ℃, heat 2 hours, at 180 ℃, heat 8 hours again, obtain thus composition epoxy resin of the present invention and relatively use the cured article of resin combination.The measurement result of the thermal conductivity of these cured articles is as shown in table 2.
Table 2
? | Embodiment 25 | Embodiment 26 | Embodiment 27 | Embodiment 28 | Embodiment 29 | Embodiment 30 | Embodiment 31 | Embodiment 32 |
The composition of title complex | ? | ? | ? | ? | ? | ? | ? | ? |
Epoxy resin composition 1 | 100 | ? | ? | ? | 100 | ? | ? | ? |
Epoxy resin composition 2 | ? | 100 | ? | ? | ? | 100 | ? | ? |
Epoxy resin composition 3 | ? | ? | 100 | ? | ? | ? | 100 | ? |
Epoxy resin composition 4 | ? | ? | ? | 100 | ? | ? | ? | 100 |
Solidifying agent 1 | ? | ? | ? | ? | 68 | ? | ? | ? |
Solidifying agent 2 | ? | ? | ? | ? | ? | 67 | ? | ? |
Solidifying agent 3 | ? | ? | ? | ? | ? | ? | 81 | ? |
Solidifying agent 4 | ? | ? | ? | ? | ? | ? | ? | 74 |
Solidifying agent 5 | 53 | 52 | 45 | 48 | ? | ? | ? | ? |
Curing catalyst | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
Inorganic filling material 1 | 350 | 348 | 332 | 339 | 385 | 382 | 414 | 398 |
Inorganic filling material 2 | 200 | 198 | 189 | 193 | 219 | 218 | 236 | 227 |
The physical property of cured article | ? | ? | ? | ? | ? | ? | ? | ? |
Thermal conductivity (W/mk) | 3.8 | 3.8 | 3.9 | 3.7 | 4.1 | 4.2 | 4.7 | 4.0 |
? | Embodiment 33 | Embodiment 34 | Embodiment 35 | Embodiment 36 | Embodiment 37 | Embodiment 38 | Embodiment 39 | Embodiment 40 | Comparative example 3 | Comparative example 4 |
The composition of title complex | ? | ? | ? | ? | ? | ? | ? | ? | ? | ? |
Epoxy resin composition 5 | 100 | ? | ? | ? | 100 | ? | ? | ? | ? | ? |
Epoxy resin composition 6 | ? | 100 | ? | ? | ? | 100 | ? | ? | ? | ? |
Epoxy resin composition 7 | ? | ? | 100 | ? | ? | ? | 100 | ? | ? | ? |
Epoxy resin composition 8 | ? | ? | ? | 100 | ? | ? | ? | 100 | ? | ? |
Epoxy resin 9 | ? | ? | ? | ? | ? | ? | ? | ? | 100 | ? |
Epoxy resin 10 | ? | ? | ? | ? | ? | ? | ? | ? | ? | 100 |
Solidifying agent 1 | ? | ? | ? | ? | 66 | ? | ? | ? | ? | ? |
Solidifying agent 2 | ? | ? | ? | ? | ? | 66 | ? | ? | ? | ? |
Solidifying agent 3 | ? | ? | ? | ? | ? | ? | 76 | ? | ? | ? |
Solidifying agent 4 | ? | ? | ? | ? | ? | ? | ? | 71 | ? | ? |
Solidifying agent 5 | 51 | 51 | 42 | 46 | ? | ? | ? | ? | 38 | 60 |
Curing catalyst | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
Inorganic filling material 1 | 345 | 345 | 325 | 334 | 380 | 380 | 403 | 391 | 316 | 366 |
Inorganic filling material 2 | 196 | 196 | 185 | 190 | 217 | 217 | 230 | 223 | 180 | 208 |
The physical property of cured article | ? | ? | ? | ? | ? | ? | ? | ? | ? | ? |
Thermal conductivity (W/mk) | 3.7 | 3.7 | 3.9 | 3.7 | 4.1 | 4.1 | 4.6 | 4.0 | 3.3 | 3.5 |
Inorganic filling material 1: ball-aluminium oxide (trade(brand)name: DAW-100, electrochemical industry is manufactured, thermal conductivity 38W/mK)
Inorganic filling material 2: boron nitride (trade(brand)name: SGP, electrochemical industry is manufactured, thermal conductivity 60W/mK)
Embodiment 41
At 70 ℃, in 1000 parts of dimethyl formamides, dissolve after the epoxy resin composition 1 obtaining in 100 parts of embodiment 1, return to room temperature.At 70 ℃, in 48 parts of dimethyl formamides, dissolve 20 parts as 1 of solidifying agent, 5-naphthylene diamine (Tokyo changes into manufacture, amine equivalent 40g/eq.), then returns to room temperature.Above-mentioned epoxy resin solution and curing agent solution are mixed, stirred with the homogenizer of agitating vane type, obtain uniform varnish, add again inorganic filling material (trade(brand)name: SGP, electrochemical industry is manufactured, thermal conductivity 60W/mK) 228 parts (being 50 parts by volume with respect to resin solid composition 100 parts by volume) and 100 parts of dimethyl formamides mix, stir, prepare composition epoxy resin of the present invention.
The glass fibre that makes the varnish of this composition epoxy resin be infiltrated up to thickness 0.2mm is weaved cotton cloth in (trade(brand)name: 7628/AS890AW, rising sun シ ュ エ ー ベ Le is manufactured), heat drying and obtain prepreg.After overlapping the Copper Foil of four these prepregs and its both sides configuration, under the condition of 175 ℃ of temperature, pressure 4MPa hot-forming 90 minutes and become one, obtain the plywood of thickness 0.8mm.Measure the thermal conductivity of this plywood, result is 4.1W/mK.
Embodiment 42
Epoxy resin composition in embodiment 41 1 is become to 100 parts of epoxy resin compositions 3, is 17 parts by the quantitative change of 1,5-naphthylene diamine, is 222 parts by the quantitative change of inorganic filling material, in addition, obtains plywood by the operation steps same with embodiment 41.Measure the thermal conductivity of this plywood, result is 4.6W/mK.
Embodiment 43
Epoxy resin composition in embodiment 41 1 is become to 100 parts of epoxy resin compositions 5, is 20 parts by the quantitative change of 1,5-naphthylene diamine, is 228 parts by the quantitative change of inorganic filling material, in addition, obtains plywood by the operation steps same with embodiment 41.Measure the thermal conductivity of this plywood, result is 4.1W/mK.
Embodiment 44
Epoxy resin composition in embodiment 41 1 is become to 100 parts of epoxy resin compositions 7, is 16 parts by the quantitative change of 1,5-naphthylene diamine, is 222 parts by the quantitative change of inorganic filling material, in addition, obtains plywood by the operation steps same with embodiment 41.Measure the thermal conductivity of this plywood, result is 4.5W/mK.
Comparative example 5
Epoxy resin composition in embodiment 41 1 is become to 100 parts of epoxy resin 10 (YL-6121H), being 23 parts by the quantitative change of 1,5-naphthylene diamine, is 234 parts by the quantitative change of inorganic filling material, in addition, obtain plywood by the operation steps same with embodiment 41.Measure the thermal conductivity of this plywood, result is 3.6W/mK.
Can be confirmed by above result, the cured article of the composition epoxy resin that contains epoxy resin composition of the present invention has good heat conductivity.Therefore, epoxy resin of the present invention is exceedingly useful during with insulating material and plywood (printed wiring board etc.) etc. for electrical and electronic parts.
Understand in detail the present invention with reference to specific embodiment, still, it is obvious to the skilled person that without departing from the spirit and scope of the present invention, can make various changes and modifications.
In addition, the Japanese patent application (Japanese Patent Application 2011-163830) that the application proposed based on July 27th, 2011, the full content of this application is quoted by reference.Whole references of quoting at this in addition, are incorporated in this specification sheets as a whole.
Industrial applicability
The cured article of composition epoxy resin of the present invention has the heat conductivity better than the cured article of existing epoxy resin, and solvent solubility is also good.Therefore, as sealing material, prepreg etc., exceedingly useful for the purposes of the broad range of electric and electronic material, formed material, mould material, stacking material, coating, tackiness agent, resist, optical material etc.
Claims (9)
1. an epoxy resin composition, its phenolic compound (a) obtaining that reacts that contains more than one compounds that represent with following formula (6) in the compound that makes to represent by following formula (1)~(5) reacts the epoxy resin (A) obtaining with epihalohydrins, and contain that phenolic compound (b) by epihalohydrins and following formula (7) are represented react the epoxy resin (B) that obtains and/or by making epihalohydrins react with the phenolic compound (c) of following formula (8) expression the epoxy resin (C) obtaining
In formula (1), R
1exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro or the carbonatoms 1~10 of carbonatoms 6~10, l represents R
1number, be 1~4 integer;
In formula (2), R
2there is independently of one another any one in alkoxyl group, morpholinyl carbonyl, phthalimide-based, piperonyl or the hydroxyl of the alkyl-carbonyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~15, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10;
In formula (3), R
3exist independently of one another, any one in alkoxyl group or the hydroxyl of the aryl of the alkyl-carbonyl of expression hydrogen atom, carbonatoms 0~10, the alkyl of carbonatoms 1~10, carbonatoms 6~10, the alkyl ester group of carbonatoms 2~10, carbonatoms 1~10, n represents carbonatoms, represent any one integer in 0,1,2, m represents R
3number, meet the relation of 1≤m≤n+2;
In formula (4), R
4there is independently of one another any one in alkoxyl group or the hydroxyl of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10;
In formula (5), R
5exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~20, the aryl of carbonatoms 6~10, carbonatoms 1~10, alkyl ester group or the hydroxyl of carbonatoms 1~10, in addition, the integer that m is 1~10;
In formula (6), R
6exist independently of one another, any one in the alkoxyl group of the alkyl of expression hydrogen atom, carbonatoms 1~10, aryl, hydroxyl, nitro, formyl radical, allyl group or the carbonatoms 1~10 of carbonatoms 6~10, k represents R
6number, be 1~4 integer;
In formula (7), R
7, X and Y exist independently of one another, represents any one in the alkoxyl group of alkyl or aryl, hydroxyl or carbonatoms 1~10 of hydrogen atom, carbonatoms 1~10, k represents R
7number, represent 1~4 integer;
In formula (8), R
8exist independently of one another, any one in the alkoxyl group of alkyl or aryl, hydroxyl or the carbonatoms 1~10 of expression hydrogen atom, carbonatoms 1~10, l represents R
8number, represent 1~4 integer, A represents direct key or has the alkylidene of the carbonatoms 5~15 of cyclic rings.
2. an epoxy resin composition, it is by making epihalohydrins and containing phenolic compound claimed in claim 1 (a) and contain phenolic compound (b) and/or the phenolic compound mixture reaction of phenolic compound (c) obtains.
3. epoxy resin composition as claimed in claim 2, it obtains by the mixture reaction that makes epihalohydrins and phenolic compound, and the mixture of described phenolic compound is that in the mixture of the phenolic compound claimed in claim 1 (a) that reacts with epihalohydrins~(c), phenolic compound (b) and the shared ratio sum of phenolic compound (c) are the mixture of the phenolic compound of 1~30 quality %.
4. a composition epoxy resin, it contains the epoxy resin composition described in any one and solidifying agent in claim 1~3.
5. a composition epoxy resin, wherein, in composition epoxy resin claimed in claim 4, contains phenolic compound (a) as solidifying agent.
6. the composition epoxy resin as described in claim 4 or 5, wherein, contains inorganic filling material more than thermal conductivity 20W/mK.
7. the composition epoxy resin as described in any one in claim 4~6, it is for encapsulating semiconductor purposes.
8. a prepreg, the fiber base material that it comprises the composition epoxy resin described in any one in claim 4~6 and sheet.
9. a cured article, it is by solidifying the composition epoxy resin described in any one in claim 4~7 or prepreg claimed in claim 8 to obtain.
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PCT/JP2012/068920 WO2013015344A1 (en) | 2011-07-27 | 2012-07-26 | Epoxy resin mixture, epoxy resin composition, prepreg, and curing product of each |
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KR101503284B1 (en) | 2013-12-17 | 2015-03-17 | 전자부품연구원 | Complex insulator composition with high thermal conductivity and method thereof |
TWI641628B (en) * | 2014-10-24 | 2018-11-21 | 新日鐵住金化學股份有限公司 | Epoxy resin composition and cured article thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09100339A (en) * | 1994-09-08 | 1997-04-15 | Sumitomo Chem Co Ltd | Epoxy resin composition and semiconductor device sealed therewith |
JP2001011296A (en) * | 1999-07-02 | 2001-01-16 | Sumitomo Chem Co Ltd | Thermosetting resin composition, insulation material for build-up construction method, and build-up printed- wiring board |
JP2004137425A (en) * | 2002-10-21 | 2004-05-13 | Dainippon Ink & Chem Inc | Epoxy resin composition and its molded and cured product |
WO2010140674A1 (en) * | 2009-06-05 | 2010-12-09 | 日本化薬株式会社 | Epoxy resin composition, prepreg and cured products thereof |
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JP3708423B2 (en) * | 2000-10-20 | 2005-10-19 | 株式会社日鉱マテリアルズ | Phenolic curing agent for epoxy resin and epoxy resin composition using the same |
JP4955856B2 (en) * | 2001-01-26 | 2012-06-20 | パナソニック株式会社 | Phosphorus-containing epoxy resin composition, prepreg, resin-coated metal foil, adhesive sheet, laminate, multilayer board, phosphorus-containing epoxy resin varnish for coating, phosphorus-containing epoxy resin sealing material, phosphorus-containing epoxy resin casting material, phosphorus for impregnation Containing epoxy resin varnish |
JP2003055434A (en) * | 2001-08-15 | 2003-02-26 | Toto Kasei Co Ltd | Flame retardant for synthetic resin, and flame- retardant resin composition containing the flame retardant |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09100339A (en) * | 1994-09-08 | 1997-04-15 | Sumitomo Chem Co Ltd | Epoxy resin composition and semiconductor device sealed therewith |
JP2001011296A (en) * | 1999-07-02 | 2001-01-16 | Sumitomo Chem Co Ltd | Thermosetting resin composition, insulation material for build-up construction method, and build-up printed- wiring board |
JP2004137425A (en) * | 2002-10-21 | 2004-05-13 | Dainippon Ink & Chem Inc | Epoxy resin composition and its molded and cured product |
WO2010140674A1 (en) * | 2009-06-05 | 2010-12-09 | 日本化薬株式会社 | Epoxy resin composition, prepreg and cured products thereof |
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CN107417890A (en) * | 2016-05-19 | 2017-12-01 | 新日铁住金化学株式会社 | Composition, hardening thing, prepreg and laminated plates |
CN107417890B (en) * | 2016-05-19 | 2021-07-20 | 日铁化学材料株式会社 | Composition, cured product, prepreg, and laminate |
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TW201305272A (en) | 2013-02-01 |
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