TWI387608B - An epoxy resin, a hardened resin composition containing the same, and a use thereof - Google Patents
An epoxy resin, a hardened resin composition containing the same, and a use thereof Download PDFInfo
- Publication number
- TWI387608B TWI387608B TW095106334A TW95106334A TWI387608B TW I387608 B TWI387608 B TW I387608B TW 095106334 A TW095106334 A TW 095106334A TW 95106334 A TW95106334 A TW 95106334A TW I387608 B TWI387608 B TW I387608B
- Authority
- TW
- Taiwan
- Prior art keywords
- epoxy resin
- group
- formula
- resin
- solvent
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 136
- 229920000647 polyepoxide Polymers 0.000 title claims description 136
- 239000011342 resin composition Substances 0.000 title claims description 75
- 239000002904 solvent Substances 0.000 claims description 86
- 229920005989 resin Polymers 0.000 claims description 71
- 239000011347 resin Substances 0.000 claims description 71
- -1 cyanate compound Chemical class 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 18
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 15
- 229930185605 Bisphenol Natural products 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000000502 dialysis Methods 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical group C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 claims description 2
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical group CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 claims description 2
- WYAFQPYCJBLWAS-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]oxirane Chemical group CC1=CC=CC(OCC2OC2)=C1 WYAFQPYCJBLWAS-UHFFFAOYSA-N 0.000 claims description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical group C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- BKYSFVJCBRHGMA-UHFFFAOYSA-N 2-(naphthalen-2-yloxymethyl)oxirane Chemical group C=1C=C2C=CC=CC2=CC=1OCC1CO1 BKYSFVJCBRHGMA-UHFFFAOYSA-N 0.000 claims 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical group C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000005577 anthracene group Chemical group 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 73
- 239000010410 layer Substances 0.000 description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- 150000002989 phenols Chemical group 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000853 adhesive Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 15
- 238000003860 storage Methods 0.000 description 15
- 239000002966 varnish Substances 0.000 description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 150000002576 ketones Chemical group 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 239000007822 coupling agent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000004917 carbon fiber Substances 0.000 description 5
- 229910000420 cerium oxide Inorganic materials 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 239000011810 insulating material Substances 0.000 description 5
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 3
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical compound BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 3
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- 229910052582 BN Inorganic materials 0.000 description 3
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- SFHGONLFTNHXDX-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenyl]phenyl]methanol Chemical group C1=CC(CO)=CC=C1C1=CC=C(CO)C=C1 SFHGONLFTNHXDX-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 150000001913 cyanates Chemical class 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000010445 mica Substances 0.000 description 3
- 229910052618 mica group Inorganic materials 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- DHBZRQXIRAEMRO-UHFFFAOYSA-N 1,1,2,2-tetramethylhydrazine Chemical compound CN(C)N(C)C DHBZRQXIRAEMRO-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 2
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- 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
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Description
本發明係關於一種高分子量之環氧樹脂及該組合物之硬化物,其對於高可靠性半導體密封用等電氣/電子零件絕緣材料以及積層板(印刷布線板、裝配基板)或CFRP(碳纖維強化塑膠),進而對於以光學材料為主之各種複合材料、接著劑、塗料等可提供有用之硬化性樹脂組合物。
又,本發明係關於一種樹脂組合物,其由於低介電常數、低介電正切故而可形成耐熱性、耐水性及耐火性優良之硬化物且操作性優良,可適用於積層板、金屬箔披覆積層板、裝配基板用絕緣材料等。
環氧樹脂組合物因其操作性以及其硬化物所具有之優良電氣特性、耐熱性、接著性及耐濕性(耐水性)等,故而可廣泛用於電氣/電子零件、構造用材料、接著劑及塗料等領域。
但是,近年來,伴隨著電氣/電子領域之發展,以樹脂組合物之高純度化為主,要求進一步提高樹脂組合物之耐濕性、密著性、介電特性、用以高效填充填充料之低黏度化、用以縮短成型週期之反應性提高等各特性。又,要求用於航空宇宙材料、休閒/運動器具用途等輕量且機械物性優良之材料作為構造材料。進而,近年來,鹵素系環氧樹脂與三氧化銻常用於耐火劑,尤其多用於電氣電子零件之耐火劑,然而存有下述意見:使用有該等之產品廢棄後由於處理不當,有助於生成二噁英等有毒物質。作為解決上述問題之方法之一,於專利文獻1或專利文獻2等中揭示可使用具有聯苯骨架之苯酚芳烷基樹脂或其環氧化物。然而,因具有該構造之樹脂結晶性較強,製造時樹脂之取出狀況或保管狀態可導致結晶析出,熔融黏度增加。又,溶解於溶劑中之情形時,亦析出、沈澱有結晶,作為組合物而使用時存有極大問題。
鑒於上述背景,於專利文獻3中,藉由控制分子內之定向性而降低其結晶性之探討還未必充分。
進而,近年來,電腦、通信機器等上所搭載之印刷布線板,其高密度化以及薄膜化不斷得以推進,則要求其具有高耐熱性、絕緣性。進而,為對應信號之高速化、高頻率化,則要求具有低介電常數以及低介電正切之材料。眾所周知氰酸酯樹脂或BT樹脂(雙馬來醯亞胺-三嗪樹脂)係兼具高耐熱性與低介電特性之樹脂材料,藉由於其中添加環氧樹脂而可降低吸水率,提高接著性及加工性。於專利文獻4中揭示有將以通式(7):
所表示之環氧樹脂、氰酸酯樹脂與溶劑所混合之清漆樹脂。
[專利文獻1]日本專利特開平11-140277號公報[專利文獻2]日本專利特開平11-140166號公報[專利文獻3]日本專利特開2003-301031號公報[專利文獻4]日本專利特開2002-309085號公報
本發明之目的在於提供一種環氧樹脂,其係苯酚芳烷基型環氧樹脂,其可抑制結晶析出,提高製造組合物時之操作性及品質管理性,進而可提高耐熱性等各特性,藉此可適用於以電氣電子零件用絕緣材料(高可靠性半導體密封材料等)以及積層板(印刷布線板、裝配基板等)或CFRP為主之各種複合材料、接著劑、塗料等。
上述專利文獻4中所揭示之環氧樹脂具有優良耐水性,然而,亦存有下述問題:因分子結構方面對稱性較高,故而溶劑溶解性較低,一旦調製成清漆樹脂後,低分子量體易作為結晶析出。進而,若單純為避免結晶性問題而提高軟化點,則反而存有難以溶解於溶劑中之可能性。
本發明之目的在於提供一種樹脂組合物,其係未析出有低分子量體且操作性優良之樹脂組合物,且可形成耐熱性、介電特性、耐水性及耐火性優良之硬化物。
本發明者等為解決上述課題努力研究之後,發現藉由控制苯酚芳烷基型環氧樹脂之聚合組成即可解決上述問題點,從而完成本發明。
即,本發明係關於(1)一種環氧樹脂,其特徵在於:包含二官能基含量(以凝膠透析層析儀測定之面積%)為20%以下之苯酚芳烷基型環氧樹脂;(2)如上述(1)中之環氧樹脂,其中苯酚芳烷基型環氧樹脂係以通式(1)所表示之構造:
(式(1)中,n表示1至10之重複數之平均值。又,Ar表示通式(2):
或通式(3):
之縮水甘油醚基,相互之間亦可相同,亦可相異。通式(2)、(3)中,m表示0至3之整數,R分別表示氫原子、碳數1至8之飽和或不飽和烷基、芳基中之任一者,相互之間亦可相同,亦可相異。);(3)如上述(2)中之環氧樹脂,其中苯酚芳烷基型環氧樹脂係以通式(4)所表示之構造:
(式中,m表示0至3之整數,n表示1至10之重複數之平均值,R分別表示氫原子、碳數1至8之飽和或者不飽和烷基、芳基中之任一者,相互之間亦可相同,亦可相異。);(4)如上述(2)中之環氧樹脂,其中通式(1)中所有R係氫原子;(5)如上述(1)至(4)中任一項之環氧樹脂,其中軟化點為70℃以上;(6)如上述(1)至(4)中任一項之環氧樹脂,其中軟化點為60℃以上,環氧當量為270 g/eq以上;(7)一種上述(1)至(6)中任一項之環氧樹脂之製造方法,其特徵在於:使用該環氧樹脂中三官能基以上之分子以及良好溶劑之溶解性較低之溶劑(以下,稱為貧溶劑),自將苯酚芳烷基型環氧樹脂或該環氧樹脂與其良好溶劑所混合之溶液中萃取去除二官能基;(8)如上述(7)中之環氧樹脂之製造方法,其中良好溶劑係酮系溶劑或者酯系溶劑;(9)如上述(7)或(8)中之環氧樹脂之製造方法,其中貧溶劑係醇類;(10)一種硬化性樹脂組合物,其含有上述(1)至(6)中任一項之環氧樹脂以及硬化劑而成;(11)一種硬化物,其係上述(10)中之硬化性樹脂組合物硬化而成;(12)一種樹脂組合物,其特徵在於:含有上述(1)中之環氧樹脂,以及以通式(5)所表示之氰酸酯化合物及/或以其作為原料之預聚物:
(式中,Qa表示直接鍵結或者自伸甲基、異亞丙基、六氟異亞丙基、亞乙基、亞乙基、雙(亞甲基)苯基、雙(亞甲基)聯苯基、聯苯亞甲基、苯基亞甲基、雙(異亞丙基)苯基、二環戊二烯基、氧原子以及硫原子之群中所選擇之取代基或者原子。Qb表示氫原子或者碳數1至4之烷基,各Qb相互之間亦可相同,亦可相異。)
或者以通式(6):
(式中,Qc表示碳數5至10之環狀或者鏈狀亞烷基或者亞茀基。Qb與通式(5)中相同。);(13)如上述(12)中之樹脂組合物,其中環氧樹脂係上述(2)中之環氧樹脂;(14)如上述(12)或(13)中之樹脂組合物,其中氰酸酯化合物係具有雙酚型構造之化合物;(15)如上述(12)至(14)中任一項之樹脂組合物,其中氰酸酯化合物中,通式(5)中之Qa係異亞丙基;(16)如上述(12)至(15)中任一項之樹脂組合物,其中通式(1)之Ar係選自由苯基縮水甘油醚基、鄰甲酚縮水甘油醚基、間甲酚縮水甘油醚基以及對甲酚縮水甘油醚基所組成之群中之縮水甘油醚基;(17)如上述(12)至(15)中任一項之樹脂組合物,其中通式(1)之Ar係α-萘酚縮水甘油醚基或者β-萘酚縮水甘油醚基;(18)如上述(12)至(17)中任一項之樹脂組合物,其中通式(1)中,Ar係通式(2)中之縮水甘油醚基,且R係氫原子或者甲基;(19)一種預浸料,其特徵在於:將上述(12)至(18)中任一項之樹脂組合物含浸於基材中而成;以及(20)一種積層板,其使用上述(19)中之預浸料而獲得。
以下,就本發明之苯酚芳烷基型環氧樹脂加以說明。
一般而言,所謂苯酚芳烷基型環氧樹脂,其係指由分子中含有苯酚類、萘酚類等酚類化合物單位以及胺基丙酸化合物單位之酚醛清漆樹脂構造之苯酚芳烷基樹脂所衍生而成之環氧樹脂。
例如,以通式(7):
(式中n表示重複數。)
所表示之環氧樹脂係於近年來,因其耐火性、密著性、耐水性等各特性優良而備受關注之苯酚芳烷基型環氧樹脂。一般而言,作為本發明之環氧樹脂原料之苯酚芳烷基樹脂可以日本專利第3122834號或日本專利特開2001-40053中所揭示之方法合成。具體而言,可列舉於酸性條件下縮合4,4'-二甲氧基甲基聯苯與酚類,或者於酸性條件下縮合4,4'-二鹵代甲基聯苯與酚類等,取代伸甲基聯苯化合物與酚類之縮合反應作為一般性合成反應之範例。將以如此方式所獲得之苯酚芳烷基樹脂進行縮水甘油化,藉此可獲得上述通式(1)之化合物。可列舉例如日本化藥股份有限公司製造之NC-3000、NC-3000-H作為市售品。
於合成上述苯酚芳烷基樹脂時所使用之酚類,其係於芳香環上具有一個苯酚性羥基之化合物。作為芳香環之苯酚性羥基以外之取代基,可列舉氫原子、碳數1至8之飽和或者不飽和烷基、芳基等。作為上述酚類之具體例,可列舉苯酚、鄰甲酚、間甲酚、對甲酚、乙基苯酚、正丙基苯酚、異丙基苯酚、第三丁基苯酚、辛基苯酚、壬基苯酚、苯基苯酚、環己基苯酚、二甲苯酚、甲基丙基苯酚、甲基丁基苯酚、α-萘酚以及β-萘酚等,但並非僅限定於該等。本發明中,該等酚類中,較好的是苯酚、甲酚、烯丙基苯酚、苯基苯酚以及萘酚。
藉由如上所述之單一環氧化所獲得之通式(1)之苯酚芳烷基型環氧樹脂,特別是其純度越高越好,以溶解於溶劑中之狀態保管之情形時,將會析出結晶。其原因在於:特別是用於液狀硬化性樹脂組合物中之情形時,製造時組合物中有機成分為均一狀態,但由於冷藏保管時會析出結晶,導致成分不均,造成硬化不良或無法獲得符合設計之硬化物性之問題。又,依照專利文獻3,於通式(8):
(式中n表示重複數。)
之構造中,可確認如下:伸甲基與羥基之鍵結位置關係係對位鍵結之比例越多,則越會顯著地產生如此之結晶化。因此,報道有於通式(8)之構造中,藉由降低伸甲基與羥基之鍵結位置關係係對位鍵合之比例,可防止結晶化。然而,使用該方法,溶劑溶解性之改善並不充分。
本發明之苯酚芳烷基型環氧樹脂,其特徵在於:二官能基物即環氧基個數為二之化合物,其含量(以凝膠透析層析儀(GPC)所測定之面積%)為20%以下。若就上述通式(1)之化合物而言,二官能基物相當於n=1之化合物。若二官能基物含量可設為20面積%以下,則於專利文獻3規定之範圍外,即,即使原位鍵結與對位鍵結之比例為1.2以下之化合物亦可避免結晶化。又,原位鍵結/對位鍵結之莫耳比超過1.2之化合物之情形時,可進一步長期地避免結晶化。
以下,就本發明之苯酚芳烷基型環氧樹脂之較好之製造法加以說明,然而,若本發明之環氧樹脂之製造法中可將二官能基物含量設為20面積%以下,則並非僅限於以下所說明之本發明之較好製造法。
以下所說明之本發明之環氧樹脂之較好製造法之要點在於選擇性去除(切除)低分子量物。關於選擇性去除低分子量物之方法,將會詳細加以說明。
一般而言,環氧樹脂之溶劑溶解性存有下述傾向:溶解於醇系或烴系化合物中之溶解性較低,又,伴隨成為高分子量,溶解於其溶劑中之溶解性亦顯著下降,由於構造原因而於芳香族烴類或酮類、酯類等中之溶解度亦會降低。藉由調節該溶解度,可選擇性去除未滿寡聚物層次之低分子量之苯酚芳烷基型環氧樹脂,可簡便取出寡聚物層次之苯酚芳烷基型環氧樹脂。藉由本方法,亦可去除原料中所含有之雜質,可改善其硬化特性、硬化物物性。
本發明之苯酚芳烷基型環氧樹脂之較好製造法大致以下述三步驟構成。即,(a)於容易溶解環氧樹脂之溶劑(良好溶劑)中溶解環氧樹脂,將環氧樹脂與溶劑均勻混合之步驟;(b)將步驟(a)中所獲得之混合物與該環氧樹脂中三官能基物以上之分子以及良好溶劑溶解性較低之溶劑(貧溶劑)混合,進行兩層分離之步驟;(c)將分離為兩層之溶液或者懸濁液進行分離,自良好溶劑層中去除溶劑,回收環氧樹脂之步驟。
再者,步驟(a)中,若不使用良好溶劑,亦可將液狀環氧樹脂直接提供至步驟(b),或者加熱熔融固體狀環氧樹脂後提供至步驟(b)。又,即使於使用良好溶劑之情形時,亦可加熱熔融樹脂。
於此可使用之環氧樹脂,亦可為市售品,亦可為經過合成者。若構造為苯酚芳烷基型之環氧樹脂,則並無特別限定。具體而言,可列舉將苯酚類、萘酚類等酚類化合物與芳香族烷氧甲基、羥甲基、鹵代甲基(4,4'-雙(氯甲基)-1,1'-聯苯、4,4'-雙(甲氧基甲基)-1,1'-聯苯、1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯、4,4'-雙(羥基甲基)-1,1'-聯苯、1,4-雙(溴甲基)苯等)之聚合物(苯酚芳烷基樹脂)進行縮水甘油化而成之苯酚芳烷基型環氧樹脂;將苯酚類、萘酚類等酚類化合物與芳香族二氯甲基類(α,α'-二氯二甲苯、雙氯甲基聯苯等)之聚合物(苯酚芳烷基樹脂)進行縮水甘油化而成之苯酚芳烷基型環氧樹脂。
作為於上述製造法中所使用之良好溶劑,可列舉酮系溶劑、酯系溶劑、醚系溶劑、非質子性極性高沸點溶劑或者芳香族烴類。具體而言,可列舉丙酮、甲基乙基酮、甲基異丁基酮、環戊酮、環己酮等酮系溶劑,乙酸乙酯、乙酸丁酯、丁酸乙酯、卡必醇乙酸酯、γ-丁內酯等酯系溶劑,四氫呋喃、二惡烷、丙二醇單甲醚等醚系溶劑,N-甲基吡咯酮、二甲基亞碸、二甲基碸、二甲基甲醯胺、二甲基乙醯胺等非質子性極性高沸點溶劑,甲苯、二甲苯等芳香族烴等,該等中較好的是酮系溶劑或者酯系溶劑。該等亦可單獨使用,亦可與其他溶劑混合使用。然而,亦可考慮與如下所述之貧溶劑之組合後加以選擇。即,例如使用有接近極性之溶劑之情形時,亦有時無需兩層分離即可成為均一溶液。或者,有可能由於組合使用而僅呈膠體狀分散。因此,必須充分考慮到樹脂、良好溶劑、貧溶劑之組合。又,根據所選擇之該溶劑,可規定殘留於樹脂中之二官能基物量。
作為用於上述製造法之貧溶劑,可列舉醇類、酮系溶劑、酯系溶劑、脂肪族/芳香族烴類,該等亦可為含水溶劑。關於是否成為貧溶劑係決定於所使用之樹脂,可溶出至樹脂之貧溶劑中較為重要。基本而言,上述所示之貧溶劑中,較好的是有機溶劑。具體而言,可列舉甲醇、乙醇、異丙醇、丁醇、乙烯醇、丙二醇等醇類,甲基異丁基酮、3-己酮等鏈狀酮,乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類,己烷、戊烷、環己烷等脂肪族烴。其中最好的是醇類。作為較好的組合,可列舉使用酮系溶劑/酯系溶劑作為良好溶劑且使用醇類作為貧溶劑之組合。該等亦可單獨使用,亦可與其他溶劑混合使用。
以下,關於上述製造法之各步驟追加說明。
.步驟(a):良好溶劑之使用量相對於樹脂為500重量%以下,較好的是100重量%以下。加熱溫度為室溫至200℃。於室溫中溶解或者呈液狀之樹脂亦可無需加熱。
.步驟(b):貧溶劑之使用量相對於樹脂為50至1000重量%,較好的是50至300重量%。混合時,為充分分散樹脂,較好的是進行加熱攪拌或回流。根據步驟(a)中良好溶劑與步驟(b)中貧溶劑之組合或使用量,可控制所獲得之環氧樹脂之純度、軟化點。例如,若二官能基物之量較少,則軟化點變高。再者,本發明中作為對象之苯酚芳烷基型環氧樹脂,由於其構造之特異性,於上述本發明之較好製造法中可選擇性去除二官能基物。例如,將甲基異丁基酮作為良好溶劑而將甲醇作為貧溶劑使用,若以苯酚芳烷基型環氧樹脂係通式(4)之環氧樹脂之情形為例,則甲醇中所含之環氧樹脂分子量分佈係二官能基物成為60面積%以上。
.步驟(c):步驟(c)中,自步驟(b)開始之靜置時間若為兩層分離階段,則並無特別指定,較好的是以10分種至5小時作為標準。最後,自已經去除貧溶劑層之殘部中回收溶劑,藉此可獲得所需之苯酚芳烷基型環氧樹脂。再者,重複操作該(a)至(c),亦可進一步降低低分子量份。
以上述方式所獲得之環氧樹脂係結晶性較低且以三官能基以上為主之環氧樹脂,該環氧當量為270 g/eq以上,較好的是280 g/eq以上且350 g/eq以下。
又,所獲得之環氧樹脂之軟化點為60℃以上,較好的是70℃以上,進而考慮到使用容易度,較好的是130℃以下,更好的是110℃以下。
繼而,關於本發明之硬化性樹脂組合物加以說明。本發明之硬化性樹脂組合物含有本發明之環氧樹脂以及硬化劑。
於以本發明之環氧樹脂以及硬化劑作為必需成分之硬化性樹脂組合物中,本發明之環氧樹脂可單獨或者與其他環氧樹脂併用。併用之情形時,環氧樹脂中之本發明之環氧樹脂比例較好的是5重量%以上,更好的是10重量%以上。再者,本發明之環氧樹脂亦可作為本發明之硬化性樹脂組合物以外之樹脂組合物之添加劑或者改質材料而使用,可提高可撓性、耐熱性等。通常,為提高韌性等特性,一般使用以橡膠成分或熱可塑性樹脂作為改質材料添加之方法,一般而言,若缺乏韌性則會使耐熱性等機械特性下降,其係眾所周知之事實。然而,即使將本發明之環氧樹脂作為添加劑而使用,亦不會降低其耐熱性即可改質物性。
與本發明之環氧樹脂併用之其他環氧樹脂,作為其具體例可列舉:雙酚類(雙酚A、雙酚F、雙酚S、雙酚、雙酚AD等)、酚類(苯酚、烷基取代苯酚、芳香族取代苯酚、萘酚、烷基取代萘酚、二羥基苯、烷基取代二羥基苯、二羥基萘等)與各種醛(甲醛、乙醛、烷醛、苯醛、烷基取代苯甲醛、羥基苯甲醛、萘醛、戊二醛、苯二甲醛、巴豆醛、桂皮醛等)之縮聚物,酚類與各種二烯化合物(二環戊二烯、萜類、乙烯環己烯、降冰片二烯、乙烯降冰片烯、四氫芴、二伸乙基苯、二伸乙基聯苯、二異丙烯基聯苯、丁二烯、異戊二烯等)之聚合物,酚類與酮類(丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮、二苯甲酮等)之縮聚物,酚類與芳香族烷氧甲基、羥甲基、鹵代甲基(4,4'-雙(氯甲基)-1,1'-聯苯、4,4'-雙(甲氧基甲基)-1,1'-聯苯、1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯、4,4'-雙(羥基甲基)-1,1'-聯苯、1,4-雙(溴甲基)苯等)之聚合物(苯酚芳烷基樹脂);二官能基含量超過20%者,雙酚類與各種醛之縮聚物,醇類等加以縮水甘油化之縮水甘油醚系環氧樹脂,脂環式環氧樹脂,縮水甘油胺系環氧樹脂,縮水甘油酯系環氧樹脂等;然而,只要係通常所使用之環氧樹脂,則並非僅限定於該等。該等亦可單獨使用,亦可使用兩種以上。
本發明之硬化性樹脂組合物中,作為硬化劑,例如可列舉胺系化合物、酸酐系化合物、醯胺系化合物以及酚系化合物等。作為可使用之硬化劑之具體例,可列舉二胺二苯基甲烷、二乙烯三胺、三乙烯四胺、二胺二苯基碸、異佛爾酮二胺等胺系化合物,二氰基二醯胺、亞麻酸之二量體與乙烯二胺所合成之聚醯胺樹脂等醯胺系化合物,苯二甲酸酐、偏苯三酸酐、均苯四甲酸酐、馬來酸酐、四氫苯二甲酸酐、甲基四氫苯二甲酸酐、甲基耐地酸酐、六氫苯二甲酸酐、甲基六氫苯二甲酸酐等酸酐系化合物,雙酚類(雙酚A、雙酚F、雙酚S、雙酚、雙酚AD等)、酚類(苯酚、烷基取代苯酚、芳香族取代苯酚、萘酚、烷基取代萘酚、二羥基苯、烷基取代二羥基苯、二羥基萘等)與各種醛(甲醛、乙醛、烷醛、苯醛、烷基取代苯甲醛、羥基苯甲醛、萘醛、戊二醛、苯二甲醛、巴豆醛、桂皮醛等)之縮聚物,酚類與各種二烯化合物(二環戊二烯、萜類、乙烯環己烯、降冰片二烯、乙烯降冰片烯、四氫芴、二伸乙基苯、二伸乙基聯苯、二異丙烯基聯苯、丁二烯、異戊二烯等)之聚合物,酚類與酮類(丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮、二苯甲酮等)之縮聚物,酚類與芳香族烷氧甲基、羥基甲基、鹵代甲基(4,4'-雙(氯甲基)-1,1'-聯苯、4,4'-雙(甲氧基甲基)-1,1'-聯苯、1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯、4,4'-雙(羥基甲基)-1,1'-聯苯、1,4-雙(溴甲基)苯等)之聚合物(苯酚芳烷基樹脂),酚類與芳香族二氯甲基類(α,α'-二氯二甲苯、雙氯甲基聯苯等)之縮聚物,雙酚類與各種醛之縮聚物以及該等改性物等酚系化合物、咪唑、BF3
-胺錯合物、胍衍生物等,但並非僅限定於該等。
本發明之硬化性樹脂組合物中,硬化劑之使用量相對於環氧樹脂之環氧基1當量,較好的是0.5至1.5當量,特別好的是0.6至1.2當量。相對於1當量環氧基,不足0.5當量之情形時或者超過1.5當量之情形時,則均容易造成硬化不完全或無法獲得良好之硬化物性。
又,使用上述硬化劑時,亦可併用硬化促進劑。作為所使用之硬化促進劑,例如可列舉2-甲基咪唑、2-乙基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑等咪唑類,2-(二甲基胺甲基)苯酚、三乙烯二胺、三乙醇胺、1,8-二氮雜雙環[5.4.0]十一碳烯-7等第三級胺類,三苯基膦、二苯基膦、三丁基膦等有機膦類,辛酸錫等金屬化合物,四苯基膦/四苯基硼酸酯、四苯基膦/乙基三苯基硼酸酯等四取代膦/四取代硼酸酯,2-乙基-4-甲基咪唑/四苯基硼酸酯、N-甲基嗎啉/四苯基硼酸酯等四苯基硼鹽等。使用硬化促進劑時之使用量,其相對於環氧樹脂100重量份,根據需要可使用0.01至15重量份。
進而,本發明之硬化性樹脂組合物中,根據需要,可添加無機填充劑或矽烷偶合材料、脫模劑、顏料等各種添加劑以及各種熱硬化性樹脂。作為無機填充劑,可列舉結晶性氧化矽、熔融氧化矽、氧化鋁、鋯石、矽酸鈣、碳酸鈣、碳化矽、氮化矽、氮化硼、氧化鋯、鎂橄欖石、塊滑石、尖晶石、二氧化鈦、滑石等粉體或者將該等球形化後之珠子等,但並非僅限定於該等。該等亦可單獨使用,亦可使用兩種以上。考慮到環氧樹脂組合物之硬化物之耐熱性、耐濕性、力學性質等方面,較好的是該等無機填充劑於硬化性樹脂組合物中所占比例為50至90重量%。
進而,本發明之硬化性樹脂組合物中,根據需要,可添加眾所周知之添加劑。作為所使用之添加劑之具體例,可列舉聚丁二烯及其改性物、丙烯腈共聚物之改性物、聚苯醚、聚苯乙烯、聚乙烯、聚醯亞胺、氟樹脂、馬來醯亞胺系化合物、氰酸酯系化合物、矽膠、矽油以及氧化矽、氧化鋁、碳酸鈣、石英粉、鋁粉末、石墨、滑石、黏土、氧化鐵、氧化鈦、氮化鋁、石棉、雲母、玻璃粉末、玻璃纖維、玻璃不織布或者碳纖維等無機填充材料,矽烷偶合劑等之填充材料之表面處理劑、脫模劑,碳黑、酞菁藍、酞菁綠等著色劑。
本發明之硬化性樹脂組合物可以將上述各成分均一混合之方式而獲得。進而,本發明之硬化性樹脂組合物以與先前所知之方法同樣方法,可容易地獲得其硬化物。例如,根據需要而使用押出機、捏和機、滾筒等,將環氧樹脂與硬化劑以及根據需要而使用之硬化促進劑以及無機填充劑、添加劑、各種熱硬化性樹脂充分混合均勻,藉此可獲得本發明之硬化性樹脂組合物,可使用熔融鑄造法或者傳送成型法或注射成型法、壓縮成型法等成型該硬化性樹脂組合物,進而於80至200℃下加熱2至10小時,可獲得硬化物。
又,依據情形,本發明之硬化性樹脂組合物亦可含有溶劑。含有溶劑之硬化性樹脂組合物係藉由熱壓成形含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙等基材中經過加熱乾燥而獲得之預浸料,可獲得本發明之硬化性樹脂組合物之硬化物。該硬化性樹脂組合物之溶劑含量,其相對於本發明之硬化性樹脂組合物與該溶劑之總量,通常為10至70重量%,較好的是15至70重量%左右。又,含有該溶劑之硬化性樹脂組合物亦可作為清漆樹脂而使用。作為溶劑,例如可列舉γ-丁內酯類、N-甲基吡咯酮(NMP)、N,N-二甲基甲醯胺(DMF)、N,N-二甲基乙醯胺、N,N-二甲基咪唑啉酮等醯胺系溶劑,四伸甲基碸等碸類、二乙烯醇二甲醚、二乙烯醇二乙醚、丙二醇單甲醚、丙二醇單甲醚單乙酸酯、丙二醇單丁醚等醚系溶劑,較好的是低級伸烷醇單或二低級烷基醚、甲基乙基酮、甲基異丁基酮等酮系溶劑,較好的是兩個烷基亦可相同或亦可不同之二低級烷酮、甲苯、二甲苯等芳香族系溶劑。該等亦可為單獨溶劑,或者亦可為兩種以上之混合溶劑。又,於剝離膜上塗布上述清漆樹脂,加熱去除溶劑且實行B級化,藉此可獲得薄層狀接著劑。該薄層狀接著劑可作為多層基板等中之層間絕緣層使用。
本發明中所獲得之硬化物可用作各種用途。一般而言,可列舉出使用有環氧樹脂等熱硬化性樹脂之各種用途,例如除接著劑、塗料、塗層劑、成形材料(含有薄層、薄膜、FRP等)、絕緣材料(包含印刷基板、電線被覆層等)、密封劑以外,亦可列舉其他樹脂等中之添加劑等。
作為接著劑,除土木用、建築用、汽車用、一般事務用、醫療用之接著劑以外,亦可列舉電子材料用之接著劑。該等之中作為電子材料用之接著劑,可列舉裝配基板等多層基板之層間接著劑、芯片接合劑、底層填料等半導體用接著劑、BGA加強用底層填料、異方性導電性膜(ACF)、異方性導電性糊膠(ACP)等安裝用接著劑等。
作為密封劑,可列舉電容器、電晶體、二極體、發光二極體、IC、LSI等用之焊接、浸塗、壓鑄模具密封,IC、LSI類之COB、COF、TAB等用之焊接密封,覆晶等用之底層填料、QFP、BGA、CSP等IC封裝類安裝時之密封(含有加強用之底層填料)等。
繼而,就本發明之其他種類之樹脂組合物加以說明。
該樹脂組合物含有本發明之環氧樹脂及以通式(5):
(式中,Qa表示直接鍵結或者伸甲基、異亞丙基、六氟異亞丙基、亞乙基、亞乙基、雙(亞甲基)苯基、雙(亞甲基)聯苯基、聯苯亞甲基、苯基亞甲基、雙(異亞丙基)苯基、二環戊二烯基、氧原子以及硫原子之群中所選擇之取代基或者原子。Qb表示氫原子或者碳數1至4之烷基,各Qb相互之間亦可相同,亦可相異。)
或者以通式(6):
(式中,Qc表示碳數5至10之環狀或者鏈狀伸烷基或者亞茀基。Qb與通式(5)中相同。)
所表示之氰酸酯化合物及/或以其為原料之預聚物。該預聚物係可藉由加熱通式(5)或者(6)之化合物而獲得。該等氰酸酯化合物以及其預聚物係可藉由眾所周知之方法獲得。
作為本發明之上述樹脂組合物中所使用之以上述式(5)或者上述式(6)所表示之氰酸酯化合物之具體例,可列舉雙(3,5-二甲基-4-苯基氰酸酯)甲烷、雙(4-苯基氰酸酯)甲烷、雙(3-甲基-4-苯基氰酸酯)甲烷、雙(3-乙基-4-苯基氰酸酯)甲烷、4,4-異亞丙基雙苯基異氰酸酯、4,4-異亞丙基雙-2-甲基苯基異氰酸酯、1,1-雙(4-苯基氰酸酯)乙烷、1,2-雙(4-苯基氰酸酯)乙烷、2,2-雙(4-苯基氰酸酯)丙烷等具有雙酚型構造之化合物,或4,4-二氰酸酯聯苯、二(4-苯基氰酸酯)醚、二(4-苯基氰酸酯)硫醚、二(4-氰酸酯-3-第三丁基-6-甲基苯基)硫醚、1,4-雙(4-苯基氰酸酯甲基)苯、4,4{1,3-伸苯基雙(1-甲基亞乙基)}雙苯基氰酸酯、4,4{1,3-伸苯基雙甲基亞乙基異亞丙基)}雙苯基氰酸酯、4,4-雙(4-苯基氰酸酯)甲基-1,1-聯苯、4,4-雙(4-氰酸酯-3-甲基苯基)甲基-1,1-聯苯、2,2-雙(4-苯基氰酸酯)-1,1,1,3,3,3-六氟丙烷、二(4-苯基氰酸酯)芴、1,1-雙(4-苯基氰酸酯)環己烷、2,2-雙(4-苯基氰酸酯)金剛烷、9,9-雙(4-苯基氰酸酯)芴、9,9-雙(4-氰酸酯-3-甲基苯基)芴、9,9-雙(4-氰酸酯-3-苯基苯基)芴、9,9-雙(4-氰酸酯-3-烯丙基苯基)芴、4,4-雙(苯基異氰酸酯甲基)-1,1'-聯苯等。又,作為三元酚之氰酸酯,例如可列舉1,1,1-三(4-苯基氰酸酯乙烷)-4-苯基氰酸酯-1,1,1-乙烷等。該等中,較好的是具有雙酚型構造之化合物。
該等氰酸酯化合物之中,究竟使用哪一種氰酸酯化合物係自具有硬化物所要求之特性者,或者自由於其構造而於常溫下呈液狀者乃至固體者均具有廣泛特性者之中,可根據用途適當加以選擇,並非特別限定者,若使用2,2-雙(4-苯基氰酸酯)丙烷或者以其預聚物作為主要成分之氰酸酯化合物,則因生產性或使用性以及成本方面良好,故而特別可取。又,預先將氰酸酯化合物進行預聚物化(通常,生成環狀三量體),可降低介電常數,又可防止成為清漆樹脂時之再結晶。本發明之樹脂組合物中,氰酸酯化合物及/或以其作為原料之預聚物,其於該成分與作為本發明之環氧樹脂以及任意成分所使用之其他環氧樹脂(下述)三種成分(以下,稱為樹脂成分)之合計重量中所占比例,通常為30至95重量%,較好的是於50至85重量%之範圍中使用。
本發明中,由於併用雙馬來醯亞胺樹脂,故而可獲得電氣特性等更加優良之硬化物。於本發明中所使用之雙馬來醯亞胺樹脂中含有多官能性馬來醯亞胺樹脂。具體而言,可列舉1,3-或1,4-二馬來醯亞胺苯、1,3-或1,4-雙(馬來醯亞胺伸甲基)苯、1,3-或1,4-二馬來醯亞胺環己烷、1,3-或1,4-雙(馬來醯亞胺伸甲基)環己烷、4,4'-二馬來醯亞胺聯苯、雙(4-馬來醯亞胺苯基)甲烷、雙(4-馬來醯亞胺苯基)醚、雙(4-馬來醯亞胺苯基)碸、雙(4-馬來醯亞胺-3-甲基苯基)甲烷、雙(4-馬來醯亞胺-3-氯苯基)甲烷、雙(4-馬來醯亞胺-3,5-二甲基苯基)甲烷、2,2'-雙(4-馬來醯亞胺-3-甲基苯基)丙烷、2,2'-雙(4-馬來醯亞胺-3,5-二溴苯基)丙烷、雙(4-馬來醯亞胺苯基)苯基甲烷、3,4-二馬來醯亞胺苯基-4'-馬來醯亞胺苯基甲烷、1,1-雙(4-馬來醯亞胺苯基)-1-苯基甲烷,以及自三聚氰胺及兩個以上苯胺之苯環藉由伸甲基鍵合之甲醛與苯胺之加成生成物所衍生而成之馬來醯亞胺等。
本發明之樹脂組合物中,本發明之環氧樹脂亦可與其他環氧樹脂併用。作為可使用之其他環氧樹脂,可列舉雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚型環氧樹脂、酚類酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、三苯基甲烷型環氧樹脂、苯酚/二環戊二烯共聚型環氧樹脂等。該等環氧樹脂可僅使用一種,或者兩種以上併用。本發明之樹脂組合物中,含有本發明之環氧樹脂與其他環氧樹脂之環氧樹脂(以下,稱為全環氧樹脂),其於樹脂成分中所占比例通常為5至70重量%,較好的是於15至50重量%之範圍內使用。
本發明之樹脂組合物中,作為賦與耐火性成分亦可含有磷化合物。作為含磷化合物,亦可為反應型者,亦可為添加型者。作為含磷化合物之具體例,可列舉三甲基磷酸酯、三乙基磷酸酯、三甲苯磷酸酯、三苯二甲基磷酸酯、甲苯二苯基磷酸酯、甲苯-2,6-二苯二甲基磷酸酯、1,3-伸苯基雙(二苯二甲基磷酸酯)、1,4-伸苯基雙(二苯二甲基磷酸酯)、4,4'-聯苯(二苯二甲基磷酸酯)等磷酸酯類,9,10-二氫-9-氧雜-10-膦菲-10-氧化物,10(2,5-二羥基苯基)-10H-9-氧雜-10-膦菲-10-氧化物等膦類,環氧樹脂與上述膦類之活性氫反應所得之含磷環氧化合物、赤磷等,較好的是磷酸酯類、膦類或含磷環氧化合物,特別好的是1,3-伸苯基雙(二苯二甲基磷酸酯)、1,4-伸苯基雙(二苯二甲基磷酸酯)、4,4'-聯苯(二苯二甲基磷酸酯)或含磷環氧化合物。本發明之樹脂組合物中,較好的是含磷化合物含量為含磷化合物/全環氧樹脂=0.1至0.6。0.1以下時,耐火性不充分,0.6以上時,可能會對硬化物之吸濕性、介電特性造成不良影響。
本發明之樹脂組合物中,為提高組合物之薄膜形成能,根據需要可添加黏合劑樹脂。作為黏合劑樹脂,可列舉丁醛系樹脂、縮醛系樹脂、丙烯系樹脂、環氧-尼龍系樹脂、NBR-苯酚系樹脂、環氧-NBR系樹脂、聚醯胺系樹脂、聚醯亞胺系樹脂、聚矽氧系樹脂等,然而並非僅限定於該等。黏合劑樹脂之添加量,其較好的是處於不會損害硬化物之耐火性、耐熱性之範圍內,相對於所需樹脂成分100重量份,通常為0.05至50重量份,較好的是0.05至20重量份,可根據需要加以使用。
根據需要,可於本發明之樹脂組合物中添加硬化促進劑。對於硬化促進劑並無特別限定,存有鐵、銅、鋅、鈷、鎳、錳及錫之有機金屬鹽或者金屬有機錯合物以及咪唑類等。作為有機金屬鹽或者有機金屬錯合物,具體而言可列舉環烷酸鋅、環烷酸鈷、環烷酸銅、環烷酸鉛、環烷酸鋅等環烷酸類,辛酸錫、辛酸鋅等辛酸類,乙醯丙酮鉛、乙醯丙酮銅、乙醯丙酮鈷、二丁基馬來酸錫等金屬螯合化合物類。作為咪唑類,可列舉2-甲基咪唑、2-苯基咪唑、2-十一烷咪唑、2-十七烷咪唑、2-苯基-4-甲基咪唑、1-苄基-2-甲基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-苯基咪唑、1-氰基乙基-2-十一烷咪唑、2,4-二胺基-6(2'-甲基咪唑(1'))乙基-s-三嗪、2,4-二胺基-6(2'-十一烷咪唑(1')乙基乙基-s-三嗪、2,4-二胺基-6(2-乙基,4-甲基咪唑(1'))乙基-s-三嗪,2,4-二胺基-6(2-甲基咪唑(1'))乙基-s-三嗪/異三聚氰酸加成物、2-甲基咪唑異三聚氰酸之2:3加成物、2-苯基咪唑異三聚氰酸加成物、2-苯基-3,5-二羥基甲基咪唑、2-苯基-3,5-二氧基乙氧基甲基咪唑之各種咪唑類,以及該等咪唑類與苯二甲酸、異苯二甲酸、對苯二甲酸、偏苯三酸、均苯四甲酸、萘二羧酸、馬來酸、水草酸等多價羧酸之鹽類。硬化促進劑相對於樹脂成分100重量份,通常為0.01至5重量份,較好的是可根據需要使用0.1至3重量份,。
本發明之樹脂組合物中亦可使用填充材料。作為填充材料,可列舉熔融氧化矽、結晶性氧化矽、碳化矽、氮化矽、氮化硼、碳酸鈣、硫酸鋇、硫酸鈣、雲母、滑石、黏土、氧化鋁、氧化鎂、氧化鋯、氫氧化鋁、氫氧化鎂、矽酸鈣、矽酸鋁、矽酸鋰鋁、矽酸鋯、鈦酸鋇、玻璃纖維、碳纖維、二硫化鉬以及石棉等,較好的是熔融氧化矽、結晶性氧化矽、氮化矽、氮化硼、碳酸鈣、硫酸鋇、硫酸鈣、雲母、滑石、黏土、氧化鋁以及氫氧化鋁。又,該等填充材料亦可一種單獨使用,或者兩種以上混合使用。
本發明之樹脂組合物中,根據使用目的,可適當添加著色劑、偶合劑、勻化劑、離子捕獲劑等。作為著色劑並無特別限制,可列舉酞菁、偶氮、二重氮、喹吖啶酮、蒽醌、黃烷士酮、Perynone、二萘嵌苯、二惡嗪、縮合偶氮、偶氮甲基等各種有機系色素,氧化鈦、硫酸鉛、鉻黃、鋅黃、鉻朱紅、孟加拉紅、鈷紫、藍、青、群青、碳黑、鉻綠、氧化鉻、鈷綠等無機顏料。
作為偶合劑,可列舉3-縮水甘油氧基丙基三甲氧基矽烷、3-縮水甘油氧基丙基三甲氧基矽烷、3-縮水甘油氧基丙基甲基二甲氧基矽烷、3-縮水甘油氧基丙基甲基二甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、N-(2-胺乙基)3-胺丙基甲基二甲氧基矽烷、N-(2-胺乙基)3-胺丙基甲基三甲氧基矽烷、3-胺丙基三乙氧基矽烷、3-巰基丙基三甲氧基矽烷、伸乙基三甲氧基矽烷、N-(2-(伸乙基苄基胺基)乙基)-3-胺丙基三甲氧基矽烷鹽酸鹽、3-甲基醯氧基丙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷等矽烷系偶合劑,異丙基(N-乙基胺基乙基乙基胺基)鈦酸酯、二(焦磷酸二辛酯)氧基乙酸鈦、四異丙基二(磷酸二辛酯)鈦酸酯、新烷氧基三(p-N-(β-胺基乙基)胺基苯基)鈦酸酯等鈦系偶合劑,乙醯丙酮鋯、甲基丙烯酸鋯、丙酸鋯、新烷氧基三(十二烷基)苯醯基鋯酸酯、新烷氧基三(乙烯二胺基乙基)鋯酸酯、新烷氧基三(間胺基苯基)鋯酸酯、銨鋯碳酸酯、乙醯丙酮鋁、甲基丙烯酸鋁、丙酸鋁等鋯或者鋁系偶合劑,較好的是矽烷系偶合劑。藉由使用偶合劑,可提高硬化物之耐濕可靠性,獲得吸濕後接著強度下降較少之硬化物。
作為勻化劑,可列舉包含丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯等丙烯酸類且分子量為4000至12000之寡聚物類,環氧化大豆脂肪酸、環氧化松香醇、氫化蓖麻油、改性聚矽氧、陰離子/非離子界面活性劑等。
本發明之樹脂組合物中,例如,可使用亨舍爾混合機、攪拌混煉機等混合機混合氰酸酯化合物及/或以其作為原料之預聚物、含有本發明之環氧樹脂之環氧樹脂成分以及根據需要而使用之含磷化合物、硬化促進劑、黏合劑樹脂、離子捕獲劑、填充劑、偶合劑、著色劑以及勻化劑等添加成分後,藉由兩條滾筒、混煉機、押出機、砂磨機等混煉機均勻分散而獲得。
又,本發明之樹脂組合物係可藉由於溶劑中以特定比例均勻混合上述各成分,製成清漆狀組合物(以下,簡稱為清漆樹脂)。作為所使用之溶劑,例如可列舉γ-丁內酯類、N-甲基吡咯酮(NMP)、N,N-二甲基甲醯胺(DMF)、N,N-二甲基乙醯胺、N,N-二甲基咪唑啉酮等醯胺系溶劑,四伸甲基碸等碸類、二乙烯醇二甲醚、二乙烯醇二乙醚、丙二醇二乙醚、丙二醇單甲醚單乙酸酯、四氫呋喃、二惡烷等醚系溶劑,甲基乙基酮、甲基異丁基酮等酮系溶劑,甲苯、二甲苯等芳香族系溶劑。該等溶劑亦可一種單獨使用,或者亦可兩種以上混合使用。清漆樹脂中之固體成分濃度(溶劑以外之成分之濃度)通常為10至80重量%,較好的是於30至70重量%之範圍內使用溶劑。
為獲得本發明之樹脂組合物之硬化物,亦可於符合硬化系之條件下進行熱硬化。例如,假定作為印刷基板使用之情形時,一般而言,硬化條件係160至240℃下硬化0.5至2小時左右。
於層間絕緣層中使用有本發明之樹脂組合物之裝配布線板可使用眾所周知之方法加以製造,並無特別限定,例如,於成為芯核之硬質積層板上,貼合使用有本發明之樹脂組合物之附帶樹脂之金屬箔後,經由蝕刻、電鍍形成布線、通道後而獲得。
於層間絕緣層中使用有本發明之樹脂組合物之裝配布線板用附帶樹脂之金屬箔,其可使用眾所周知之方法加以製造,並無特別限定,例如,可於電解銅箔上,以刮刀式塗布機塗布本發明之樹脂組合物,以在線乾燥去除溶劑後獲得。又,將上述清漆樹脂含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙等基材中加熱半乾燥後獲得預浸料,將預浸料進行積層、熱壓制成型後製成積層板。
繼而,根據實施例更加具體地說明本發明,但本發明並非僅限定於該等實施例。再者,以下,「份」除有特別指定外均表示重量份。又,實施例中,根據以下條件測定出環氧當量以及軟化點。
1)環氧當量:基於JISK-7236之方法測定。
2)軟化點:基於JISK-7234之方法測定。
3)GPC之測定條件如下所述。
機種:Shodex SYSTEM-21管柱:KF-804L+KF-803L(×2條)聯結溶離液:THF(四氫呋喃);1 mL/min.40℃檢測器:UV(254 nm;UV-41)樣本:約0.4% THF溶液(注射20 μL)解析曲線:使用Shodex製造之標準聚苯乙烯
於具備有攪拌機、回流冷卻管、攪拌裝置之燒瓶中,添加100份之苯酚-聯苯酚醛清漆型環氧樹脂(日本化藥股份有限公司製造,商品名NC-3000-H,環氧當量為288 g/eq,軟化點為68℃,正位鍵合:對位鍵結(莫耳比)=60:40至55:45)、50份之甲基異丁基酮,於100℃下充分溶解。冷卻至60℃後,添加200份之甲醇,將所獲得之懸濁液於回流狀態下攪拌一小時後,於50℃下靜置30分鐘,可確認分離為兩層。以傾析法萃取分離為兩層之上層部,於殘渣中進而追加25份之甲基異丁基酮與200份之甲醇,再次於回流狀態下攪拌一小時。此後,於50℃下靜置30分鐘,可確認分離為兩層。以傾析法分離出分離為兩層之上層部。進而,重複兩次該靜置、分離操作。於加熱減壓條件下回收所獲得之殘渣中之溶劑,藉此獲得83份所需之環氧樹脂(以下,稱為EP1)。所獲得之EP1之環氧當量為294 g/eq,軟化點為78℃。
若將所獲得之環氧樹脂EP1與NC-3000-H之資料進行比較,則如下表1所示。再者,保存穩定性之試驗結果係分別表示於70重量%之甲基乙基酮溶液中5℃下實行冷藏保管時之結果。
[表1]
於具備有攪拌機、回流冷卻管、攪拌裝置之燒瓶中,添加100份之苯酚-聯苯酚醛清漆型環氧樹脂(日本化藥股份有限公司製造,商品名NC-3000,環氧當量為274 g/eq,軟化點為54℃)、50份之甲基異丁基酮,於100℃下充分溶解。冷卻至60℃後,添加200份之甲醇,將所獲得之懸濁液於回流狀態下攪拌1小時後,於50℃下靜置30分鐘,可確認分離為兩層。以傾析法萃取分離為兩層之上層部,於殘渣中進而追加25份之甲基異丁基酮與200份之甲醇,再次於回流狀態下攪拌1小時。此後,於50℃下靜置30分鐘,可確認分離為兩層。以傾析法分離出分離為兩層之上層部。進而,重複三次該靜置、分離操作。於加熱減壓條件下回收所獲得之殘渣中之溶劑,藉此獲得76份所需之環氧樹脂(以下,稱為EP2)。所獲得之EP2之環氧當量為283 g/eq,軟化點為69℃。
若將所獲得之環氧樹脂EP2與NC-3000之資料進行比較,則如下表2所示。再者,保存穩定性之試驗結果係分別表示於70重量%之甲基乙基酮溶液中5℃下實行冷藏保管時之結果。
於具備有攪拌機、回流冷卻管、攪拌裝置之燒瓶中,對於100份之(苯酚、β-萘酚)-聯苯酚醛清漆型環氧樹脂(根據專利3575776號中揭示之方法製造,萘酚/(苯酚+萘酚)=0.34,環氧當量為284 g/eq,軟化點為69℃)實行與實施例1同樣之操作,藉此獲得81份所需之環氧樹脂(EP3)。所獲得之EP3之環氧當量為299 g/eq,軟化點為83℃,二官能基物之面積%為18%。
對於實施例1中所獲得之本發明之環氧樹脂(EP1)以及NC-3000-H,以苯酚酚醛清漆樹脂(明和化成工業股份有限公司製造,商品名H-1,羥基當量為105 g/eq)作為硬化劑,根據下述表3所表示之添加比添加三苯基膦(TPP)作為硬化促進劑,調製出組合物,藉由傳送成型而獲得樹脂成形體,於160℃下硬化2小時,進而於180℃下硬化8小時。
測定所獲得之硬化物物性之結果示於表4中。再者,根據下述方法測定物性值。
玻璃轉移點:TMA熱機械測定裝置:真空理工(股份有限公司)製造TM-7000升溫速度:2℃/min.DMA動態黏彈性測定裝置:彎曲強度:JIS K-6911破壞韌性(K1C):JIS K-6911
[表4]
根據表5所表示之組成(數值為「份」)混合各成分後調製出清漆樹脂。將所獲得之清漆樹脂保持於5℃之恆溫狀態下,調查保存一個月後有無結晶析出。又,以分別於電解銅箔(厚度35 μm,古川電工製造)上乾燥後之厚度成為75 μm之方式,使用刮刀式塗布機塗布所獲得之清漆樹脂,於150℃下加熱乾燥2分鐘,進而於170℃下加熱乾燥2分鐘之條件下去除溶劑,獲得附帶有樹脂之銅箱。於蝕刻處理後去除銅箔之無鹵FR-4基板(東芝化學製造,商品名TCL-W-555MU,厚度為0.4 mm)兩面上,貼合該附帶有樹脂之銅箔加以硬化(壓力1 Pa、溫度170℃下1小時),作為耐火性試驗用樣本。又,自銅箔上去除上述經過加熱乾燥之殘部,且測定出經過壓縮成型者之玻璃轉移點。清漆樹脂之貯藏穩定性、耐火性試驗以及玻璃轉移點之測定結果示於表5中。
[表5]
註:氰酸酯化合物溶液:氰酸酯樹脂預聚物B-40S(CIBAGEIGY公司製造之雙酚A二氰酸酯樹脂,三量體含有率為40重量%,固體成分為75重量%之MEK溶液)磷化合物:FP-500(旭電化股份有限公司製造、磷系耐火劑)黏合劑樹脂:BPAM-01(日本化藥股份有限公司製造、橡膠改性聚醯胺樹脂)硬化促進劑:二鋅8%(日本化學產業股份有限公司製造、2-乙基己基酸鋅礦油精溶液)
根據以上之結果,因本發明之苯酚芳烷基型環氧樹脂即使溶解於溶劑中後保存於低溫下,亦難以析出結晶,故而於利用有其之硬化性樹脂組合物中,可防止長期保存後之性能下降,有利於提高樹脂組合物之保存穩定性。進而,所獲得之硬化性樹脂組合物之硬化物具有非常高之耐熱性,亦可提高機械性特性。因此,本發明之環氧樹脂及硬化性樹脂組合物極其適用於成形材料、鑄造材料、積層材料、塗料、接著劑、抗蝕劑等廣泛用途。
又,使用有本發明之環氧樹脂之本發明之樹脂組合物(清漆樹脂),其貯藏穩定性優良,且其硬化物表現出優良之耐火性以及耐熱性。
本發明之苯酚芳烷基型環氧樹脂即使溶解於溶劑中後保存於低溫下,亦難以析出結晶,故而於利用有其之樹脂組合物中,可防止長期保存後之性能下降,有利於提高樹脂組合物之保存穩定性。又,含有本發明之環氧樹脂以及硬化劑之硬化性樹脂組合物之硬化物,其與先前可從市場上購得者相比,耐熱性、機械性強度較為優良。以如此方式製造組合物時,可提高操作性或品質管理性,進而亦可提高其硬化物性,故而可適用於電氣電子零件用絕緣材料(高可靠性半導體密封材料等)以及積層板(印刷布線板、裝配基板等)或以CFRP為主之各種複合材料、接著劑、塗料等。
又,含有本發明之環氧樹脂以及氰酸酯化合物類之樹脂組合物,其貯藏穩定性優良,且其硬化物亦具有優良之耐熱性、介電特性、耐水性以及耐火性。該樹脂組合物可適用於製造電子電路基板中所使用之銅披覆積層板,或適用於電子零件中所使用之密封材料/成形材料/鑄造材料/接著劑/電絕緣塗料用材料等。
Claims (18)
- 一種環氧樹脂,其特徵在於:含有二官能基含量為(以凝膠透析層析儀測定之面積%)20%以下之苯酚芳烷基型環氧樹脂,其中該苯酚芳烷基型環氧樹脂係以通式(1)所表示之構造:
- 如請求項1之環氧樹脂,其中苯酚芳烷基型環氧樹脂係以通式(4)所表示之構造:
- 如請求項1之環氧樹脂,其中通式(1)中R全部皆為氫原子。
- 如請求項1至3中任一項之環氧樹脂,其中軟化點為70℃以上。
- 如請求項1至3中任一項之環氧樹脂,其中軟化點為60℃以上,環氧當量為270 g/eq以上。
- 一種請求項1至5中任一項之環氧樹脂之製造方法,其特徵在於:使用該環氧樹脂中三官能基物以上之分子以及良好溶劑之溶解性較低之溶劑(以下,稱為貧溶劑),自苯酚芳烷基型環氧樹脂或者該環氧樹脂與其良好溶劑混合之溶液中萃取而去除二官能基物,其中該苯酚芳烷基型環氧樹脂係以通式(1)所表示之構造:
- 如請求項6之環氧樹脂之製造方法,其中良好溶劑係酮系溶劑或者酯系溶劑。
- 如請求項6或7之環氧樹脂之製造方法,其中貧溶劑係醇類。
- 一種硬化性樹脂組合物,其含有請求項1至5中任一項之環氧樹脂以及硬化劑而成。
- 一種硬化物,其係將請求項9之硬化性樹脂組合物硬化而成。
- 一種樹脂組合物,其特徵在於:含有請求項1之環氧樹脂以及以通式(5)所表示之氰酸酯化合物及/或以其作為 原料之預聚物:
- 如請求項11之樹脂組合物,其中氰酸酯化合物係具有雙酚型構造之化合物。
- 如請求項11至12中任一項之樹脂組合物,其中氰酸酯化合物中,通式(5)之Qa係異亞丙基。
- 如請求項11至13中任一項之樹脂組合物,其中通式(1)之Ar係選自由苯基縮水甘油醚基、鄰甲酚縮水甘油醚基、 間甲酚縮水甘油醚基以及對甲酚縮水甘油醚基所組成之群中之縮水甘油醚基。
- 如請求項11至13中任一項之樹脂組合物,其中通式(1)之Ar係α-萘酚縮水甘油醚基或者β-萘酚縮水甘油醚基。
- 如請求項11至15中任一項之樹脂組合物,其中通式(1)中,Ar係通式(2)之縮水甘油醚基,且R係氫原子或者甲基。
- 一種預浸料,其特徵在於:於基材中含浸有請求項11至16中任一項之樹脂組合物。
- 一種積層板,其係使用請求項17之預浸料而獲得。
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