JPS6381139A - Prepreg for bonding - Google Patents
Prepreg for bondingInfo
- Publication number
- JPS6381139A JPS6381139A JP22482786A JP22482786A JPS6381139A JP S6381139 A JPS6381139 A JP S6381139A JP 22482786 A JP22482786 A JP 22482786A JP 22482786 A JP22482786 A JP 22482786A JP S6381139 A JPS6381139 A JP S6381139A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- prepreg
- resin composition
- solution
- saturated polyester
- 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
Links
- 229920005989 resin Polymers 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 28
- 239000011342 resin composition Substances 0.000 claims abstract description 12
- 229920001225 polyester resin Polymers 0.000 claims abstract description 11
- 239000004645 polyester resin Substances 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 8
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 8
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims abstract description 7
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 5
- 239000004643 cyanate ester Substances 0.000 claims description 9
- -1 cyanic acid ester Chemical class 0.000 abstract description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 3
- QQZZMAPJAKOSNG-UHFFFAOYSA-N (3-cyanatophenyl) cyanate Chemical compound N#COC1=CC=CC(OC#N)=C1 QQZZMAPJAKOSNG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 description 12
- 230000001070 adhesive effect Effects 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
- 238000001723 curing Methods 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000005476 soldering Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- QMTFKWDCWOTPGJ-KVVVOXFISA-N (z)-octadec-9-enoic acid;tin Chemical compound [Sn].CCCCCCCC\C=C/CCCCCCCC(O)=O QMTFKWDCWOTPGJ-KVVVOXFISA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVTMVUFBBYUSKS-UHFFFAOYSA-N 1,4-bis(prop-2-enyl)benzene Chemical compound C=CCC1=CC=C(CC=C)C=C1 JVTMVUFBBYUSKS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GGSRTHRSSCWGGK-UHFFFAOYSA-L 2,2-dibutyl-5-hydroxy-1,3,2-dioxastannepane-4,7-dione Chemical compound CCCC[Sn]1(CCCC)OC(=O)CC(O)C(=O)O1 GGSRTHRSSCWGGK-UHFFFAOYSA-L 0.000 description 1
- ACUUVWABACRCCZ-UHFFFAOYSA-N 2-(2-ethyl-1h-imidazol-5-yl)propanenitrile Chemical compound CCC1=NC=C(C(C)C#N)N1 ACUUVWABACRCCZ-UHFFFAOYSA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- SIQHSJOKAUDDLN-UHFFFAOYSA-N 2-methyl-1-propylimidazole Chemical compound CCCN1C=CN=C1C SIQHSJOKAUDDLN-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- UCNCZASVJWGNBZ-UHFFFAOYSA-N 3-(2-ethyl-5-methyl-1h-imidazol-4-yl)propanenitrile Chemical compound CCC1=NC(CCC#N)=C(C)N1 UCNCZASVJWGNBZ-UHFFFAOYSA-N 0.000 description 1
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- SZUPZARBRLCVCB-UHFFFAOYSA-N 3-(2-undecylimidazol-1-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC=CN1CCC#N SZUPZARBRLCVCB-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- GQICUEKWMLCHMZ-UHFFFAOYSA-N O(C#N)C1=CC=C(C=C1)C(CC)(C1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N Chemical compound O(C#N)C1=CC=C(C=C1)C(CC)(C1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N GQICUEKWMLCHMZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 description 1
- CNUHQZDDTLOZRY-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfanylphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1SC1=CC=C(OC#N)C=C1 CNUHQZDDTLOZRY-UHFFFAOYSA-N 0.000 description 1
- BUPOATPDNYBPMR-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfonylphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1S(=O)(=O)C1=CC=C(OC#N)C=C1 BUPOATPDNYBPMR-UHFFFAOYSA-N 0.000 description 1
- PPZSVSGWDQKBIW-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphanyloxyphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OP(OC=1C=CC(OC#N)=CC=1)OC1=CC=C(OC#N)C=C1 PPZSVSGWDQKBIW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920006230 thermoplastic polyester resin Polymers 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Reinforced Plastic Materials (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、低誘電率、高電気絶縁性、高耐熱性、可撓性
、低吸湿性、高接着性などの物性に優れ、樹脂流れが少
なく、埋め込み性に優れた接着用プリプレグであり、多
層プリント板の層間接着や表層金属箔の接着用プリプレ
グ、半導体チップ装着用の凸部及びその凸部周囲に一段
以上の電極用端子部を有する多層プリント板の層間接着
用プリプレグ、金属箔張金属芯積層板用の金属箔接着用
プリプレグ、熱放散用の金属板接着用のプリプレグ、可
撓性のプリント配線板、半硬化金属箔付きプリプレグな
どに好適に使用されるものである。[Detailed Description of the Invention] [Field of Industrial Application] The present invention has excellent physical properties such as low dielectric constant, high electrical insulation, high heat resistance, flexibility, low moisture absorption, and high adhesiveness, and It is an adhesive prepreg with low embeddability and excellent embeddability, and is used for interlayer adhesion of multilayer printed boards and adhesion of surface metal foil, as well as for attaching protrusions for mounting semiconductor chips and one or more stages of electrode terminals around the protrusions. prepreg for adhesion between layers of multilayer printed boards, prepreg for adhesion of metal foil for metal foil-clad metal core laminates, prepreg for adhesion of metal plates for heat dissipation, flexible printed wiring boards, prepreg with semi-hardened metal foil It is suitably used for such purposes.
熱可塑性ポリエステル樹脂変性の多官能性シアン酸エス
テル樹脂組成物は、そのままフィルムとして、又はガラ
ス布、石英繊維布、アラミド布、などの繊維布を基材と
するプリプレグとすることが知られている(特開昭60
−192779 、同6O−233175)。これらは
、優れた接着力、耐熱性などを有するものであるが、よ
り低誘電率を要求される用途には必ずしも充分ではなく
、より優れた電気特性が要求されていた。It is known that a polyfunctional cyanate ester resin composition modified with a thermoplastic polyester resin can be used as a film as it is or as a prepreg based on fiber cloth such as glass cloth, quartz fiber cloth, aramid cloth, etc. (Unexamined Japanese Patent Publication 1986
-192779, 6O-233175). Although these have excellent adhesive strength and heat resistance, they are not necessarily sufficient for applications requiring lower dielectric constants, and even better electrical properties have been required.
又、フッ素樹脂は、低誘電率であることなど電気特性の
優れた樹脂であり、多孔質のフィルムやシートも知られ
ている。しかし、これは接着性に劣るという欠点があっ
た。Furthermore, fluororesin is a resin with excellent electrical properties such as a low dielectric constant, and porous films and sheets are also known. However, this had the drawback of poor adhesiveness.
本発明は、誘電率などの電気特性により優れ、厚みの均
一性、プリント配線網の埋め込み性、低樹脂流れ性に優
れた接着用プリプレグを得るべく検討した結果、完成し
たものである。The present invention was completed as a result of studies aimed at obtaining an adhesive prepreg that has excellent electrical properties such as dielectric constant, uniformity of thickness, ease of embedding printed wiring networks, and low resin flowability.
すなわち、本発明は、(a)分子中にシアナト基を2個
以上含有する多官能性シアン酸エステル樹脂組成物と(
b)実質的に非結晶性の熱可塑性飽和ポリエステル樹脂
とを必須成分とする熱硬化性樹脂組成物の溶液を(c)
延伸多孔質四弗化エチレン樹脂シートもしくはフィルム
に含浸し、乾燥し、樹脂成分を半硬化状態としてなるこ
とを特徴とする接着用プリプレグである。That is, the present invention provides (a) a polyfunctional cyanate ester resin composition containing two or more cyanato groups in the molecule;
b) A solution of a thermosetting resin composition containing a substantially amorphous thermoplastic saturated polyester resin as an essential component (c)
This adhesive prepreg is characterized in that it is impregnated into a stretched porous polytetrafluoroethylene resin sheet or film and dried to bring the resin component into a semi-cured state.
以下、本発明の構成について説明する。The configuration of the present invention will be explained below.
本発明の接着用プリプレグの製造に用いる樹脂成分(a
)である多官能性シアン酸エステル樹脂組成物とは、シ
アナト基を有する多官能性シアン酸エステル、そのプレ
ポリマー等を必須成分としてなるものであり、シアナト
樹脂(特公昭41−1928、同45−11712、同
44−1222 、DB−1,190,184等)、シ
アン酸エステル−マレイミド樹脂、シアン酸エステル−
マレイミド−エポキシ樹脂(特公昭54−30440、
同52−31279、USP−4,110,364等)
、シアン酸エステル−エポキシ樹脂(特公昭46−41
112)などで代表されるものである。The resin component (a) used in the production of the adhesive prepreg of the present invention
) is a polyfunctional cyanate ester resin composition that contains a polyfunctional cyanate ester having a cyanato group, its prepolymer, etc. as essential components, and is a cyanato resin (Japanese Patent Publication No. 41-1928; -11712, 44-1222, DB-1,190,184, etc.), cyanate ester-maleimide resin, cyanate ester-
Maleimide-epoxy resin (Special Publication No. 54-30440,
52-31279, USP-4,110,364, etc.)
, cyanate ester-epoxy resin (Special Publication No. 46-41
112), etc.
ここに、成分(a)の必須成分である多官能性シアン酸
エステルとして好適なものは、下記一般式(1)%式%
(1)
(式中のmは2以上、通常5以下の整数であり、Rは芳
香族の有機基であって、上記シアナト基は該有機基の芳
香環に結合しているもの)
で表される化合物である。具体的に例示すれば1゜3−
又は1,4−ジアリルベンゼン、1.3.5− )リシ
アナトベンゼン、1.3−、1.4−、1.6−、1.
8−、2.6−又は2゜7−ジシアナトナフタレン、1
.3.6−)リシアナトナフタレン、4.10”ジシア
ナトビフェニル、ビス(4−ジシアナトフエニル)メタ
ン、2.2−ビス(4−シアナトフェニル)プロパン、
2.2−ビス(3,5−ジクロロ−4−シアナトフェニ
ル)プロパン、2,2−ビス(3,5−シfロモー4−
シアナトフェニル)プロパン、ビス(4−シアナトフェ
ニル)エーテル、ビス(4−シアナトフェニル)チオエ
ーテル、ビス(4−シアナトフェニル)スルホン、トリ
ス(4−シアナトフェニル)ホスファイト、トリス(4
−シアナトフェニル)ホスフェート、およびノボラック
とハロゲン化シアンとの反応により得られるシアン酸エ
ステルなどである。これらのほかに特公昭41−192
8、同43−18468、同44−4791 、同45
−11712、同46−41112、同47−2685
3および特開昭51−63149などに記載のシアン酸
エステルも用いつる。Here, a preferable polyfunctional cyanate ester which is an essential component of component (a) has the following general formula (1)% formula%
(1) (In the formula, m is an integer of 2 or more and usually 5 or less, R is an aromatic organic group, and the cyanato group is bonded to the aromatic ring of the organic group) It is a compound that is To give a concrete example, 1゜3-
or 1,4-diallylbenzene, 1.3.5-) lycyanatobenzene, 1.3-, 1.4-, 1.6-, 1.
8-, 2.6- or 2°7-dicyanatonaphthalene, 1
.. 3.6-) lycyanatonaphthalene, 4.10” dicyanatobiphenyl, bis(4-dicyanatophenyl)methane, 2.2-bis(4-cyanatophenyl)propane,
2.2-bis(3,5-dichloro-4-cyanatophenyl)propane, 2,2-bis(3,5-cyflomo4-
Cyanatophenyl)propane, bis(4-cyanatophenyl)ether, bis(4-cyanatophenyl)thioether, bis(4-cyanatophenyl)sulfone, tris(4-cyanatophenyl)phosphite, tris(4-cyanatophenyl)propane,
-cyanatophenyl) phosphate, and cyanic acid esters obtained by the reaction of novolaks with cyanogen halides. In addition to these, the special public interest
8, 43-18468, 44-4791, 45
-11712, 46-41112, 47-2685
Cyanic acid esters described in No. 3 and JP-A-51-63149 can also be used.
また、上述した多官能性シアン酸エステルはプレポリマ
ーとして用いることができる。これらのプレポリマーは
、前記シアン酸エステル中のシアン基が三量化すること
によって形成されるsym −トリアジン環を、一般に
分子中に有している。本発明においては、数平均分子量
300〜6.000の前記プレポリマーを用いるのが好
ましい。Moreover, the above-mentioned polyfunctional cyanate ester can be used as a prepolymer. These prepolymers generally have a sym-triazine ring in the molecule, which is formed by trimerization of the cyanide groups in the cyanate ester. In the present invention, it is preferable to use the prepolymer having a number average molecular weight of 300 to 6.000.
上記の多官能性シアン酸エステルには、必要に応じて熱
硬化性のモノマーもしくはプレポリマーを配合した組成
物として使用する。このようなものとしては、ビス(4
−マレイミドフェニル)メタンなどの多官能性マレイミ
ド化合物;多官能性(メタ)アクリレート、アルキル(
メタ)アクリレート、エポキシ(メタ)アクリレートな
どのポリ(メタ)アクリレート類;ジアリルフタレート
、ジビニルベンゼン、ジアリルベンゼン、トリアルケニ
ルイソシアヌレートなどのポリアリル化合物及びそのプ
レポリマー;ジシクロペンタジェン、シクロペンタジェ
ン及びそのプレポリマー;フェノール樹脂;エポキシ樹
脂などの公知の樹脂類が例示され、特に、多官能性マレ
イミド化合物、エポキシ樹脂、アルキル(メタ)アクリ
レート及びアルキル−ポリ−(メタ)アクリレート等が
接着力の向上や作業性の改善等の面より好ましく使用さ
れる。The above polyfunctional cyanate ester is used as a composition containing a thermosetting monomer or prepolymer, if necessary. Such items include screws (4
- polyfunctional maleimide compounds such as maleimidophenyl)methane; polyfunctional (meth)acrylates, alkyl(
Poly(meth)acrylates such as meth)acrylate and epoxy(meth)acrylate; polyallyl compounds and their prepolymers such as diallyl phthalate, divinylbenzene, diallylbenzene, trialkenyl isocyanurate; dicyclopentadiene, cyclopentadiene and their Known resins such as prepolymers, phenolic resins, and epoxy resins are exemplified, and in particular, polyfunctional maleimide compounds, epoxy resins, alkyl (meth)acrylates, and alkyl-poly-(meth)acrylates can improve adhesive strength and It is preferably used from the viewpoint of improving workability.
本発明の(b)成分の実質的に非結晶性の熱可塑性飽和
ポリエステル樹脂とは、芳香族乃至脂肪族のジカルボン
酸と脂肪族乃至脂環族のジオール若しくはそのプレポリ
マーとを主成分として重縮合させてなるものである。本
発明では、通常、末端官能基数より算出される数平均分
子量が1.500〜25、000、好ましくは5.00
0〜22.000のものが相溶性などより好ましい。又
、水酸基価が1〜30mg40117gのものが好適で
ある。これは、実質的に非結晶性の熱可塑性飽和ポリエ
ステル樹脂に遊離の水酸基もしくはカルボキシル基が過
剰に有った場合には、これらの基と(a)成分のシアナ
ト基とが除々に常温においても反応し、組成物の保存安
定性が劣ることとなるためである。また、結晶性は低い
程好ましく、用いる酸およびアルコール成分の種類およ
び使用量比を選択する。The substantially non-crystalline thermoplastic saturated polyester resin of component (b) of the present invention is a polyester resin mainly composed of an aromatic or aliphatic dicarboxylic acid and an aliphatic or alicyclic diol or a prepolymer thereof. It is formed by condensation. In the present invention, the number average molecular weight calculated from the number of terminal functional groups is usually 1.500 to 25,000, preferably 5.00.
A value of 0 to 22,000 is preferable in terms of compatibility. Moreover, those having a hydroxyl value of 1 to 30 mg and 40,117 g are suitable. This means that when a substantially non-crystalline thermoplastic saturated polyester resin has an excess of free hydroxyl groups or carboxyl groups, these groups and the cyanato groups of component (a) gradually dissolve even at room temperature. This is because the composition will react and the storage stability of the composition will be poor. Furthermore, the lower the crystallinity, the better, and the types and usage ratios of the acid and alcohol components to be used are selected.
芳香族乃至脂肪族のポリカルボン酸としては、例えば、
テレフタル酸、イソフタル酸、マロン酸、コハク酸、ア
ジピン酸、ピメリン酸、スペリン酸、アゼライン酸、セ
パチン酸、およびこれらの低級アルキルエステル、酸無
水物、並びに、カルボキシル基末端飽和ポリエステル樹
脂の低分子量の熱分解物などが挙げられる。Examples of aromatic to aliphatic polycarboxylic acids include:
Terephthalic acid, isophthalic acid, malonic acid, succinic acid, adipic acid, pimelic acid, superric acid, azelaic acid, sepacic acid, lower alkyl esters and acid anhydrides thereof, and low molecular weight carboxyl group-terminated saturated polyester resins. Examples include thermal decomposition products.
又、脂肪族乃至脂環族のポリオール若しくはそのプレポ
リマーとしては、エチレングリコール、プロピレングリ
コール、1.3−プロパンジオール、1.4−ブタンジ
オール、1.5−ベンタンジオール、1゜6−ヘキサン
ジオール、ネオペンチルグリコール、ジエチレングリコ
ール、トリエチレングリコール、ポリエチレングリコー
ル、ポリプロピレングリコール、ポリブチレングリコー
ル、ポリカプロラクトンジオール、2.2−ジメチルプ
ロパンジオール、2.2−ビス(4−ヒドロキシシクロ
ヘキシル)ブロハ:/、1.4−ジヒドロキシメチルシ
クロへ一1F−サ7、トリメチロールプロパン、1.2
.3−トリヒドロキシプロパン、テトラメチロールメタ
ンなどが挙げられ、非結晶性とする為に、分子毒が低い
ものを用いるのが良い。In addition, examples of aliphatic to alicyclic polyols or prepolymers thereof include ethylene glycol, propylene glycol, 1.3-propanediol, 1.4-butanediol, 1.5-bentanediol, and 1゜6-hexanediol. , neopentyl glycol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, polybutylene glycol, polycaprolactone diol, 2.2-dimethylpropanediol, 2.2-bis(4-hydroxycyclohexyl)broha:/, 1. 4-dihydroxymethylcyclohe-1F-S7, trimethylolpropane, 1.2
.. Examples include 3-trihydroxypropane and tetramethylolmethane, and in order to make it non-crystalline, it is preferable to use one with low molecular toxicity.
かかる実質的に非結晶性の熱可塑性飽和ポリエステル樹
脂としては、日本合成化学工業Glから商品名「ポリエ
スタ−」として市販されているものが好適である。As such a substantially non-crystalline thermoplastic saturated polyester resin, one commercially available from Nippon Gosei Chemical Industry Co., Ltd. under the trade name "Polyester" is suitable.
上記した成分(a)と成分(b)との配合比率は、特に
限定のないものであるが、通常、成分(a)30〜95
重量部、成分ら)70〜5重量部である。The blending ratio of component (a) and component (b) described above is not particularly limited, but usually component (a) is 30 to 95
(parts by weight, components, etc.) 70 to 5 parts by weight.
成分(a)及びら)の混合方法は特に限定されないが、
通常、(a)成分の溶液を調製し、これに(b)成分又
は(b)成分の溶液を混合する方法;無溶剤でそれぞれ
の成分を溶融混合した後、溶液とする方法;更に、前記
した併用可能成分のなかの反応性希釈剤などを使用し無
溶剤の液状乃至ペースト状の組成物とする方法等によっ
て樹脂組成物を予め調製し、これに必要に応じて後記す
る触媒を添加し混合する方法;前記した混合時に触媒等
を併用して混合する方法などによる。有機溶媒としては
好適には、メチルエチルケトン、アセトン、トルエン、
キシレン、トリクロロエチレン、ジオキサンなどが例示
され、濃度としては含浸に必要な樹脂量及び粘度により
選択されるが、通常、20〜60重量%が好適である。The method of mixing components (a) and (a) is not particularly limited, but
Usually, a method of preparing a solution of component (a) and mixing it with component (b) or a solution of component (b); a method of melting and mixing each component without a solvent and then preparing a solution; A resin composition is prepared in advance by a method such as a method of making a solvent-free liquid or paste composition using a reactive diluent among the components that can be used in combination, and a catalyst described later is added to this as necessary. Mixing method: The method of mixing using a catalyst or the like at the time of mixing as described above. Suitable organic solvents include methyl ethyl ketone, acetone, toluene,
Examples include xylene, trichloroethylene, dioxane, etc., and the concentration is selected depending on the amount of resin and viscosity required for impregnation, but usually 20 to 60% by weight is suitable.
本発明の(c)成分の延伸多孔質四弗化エチレン樹脂シ
ートもしくはフィルムとは、例えば、特公昭51−18
991号公報に記載の方法により製造されるものが挙げ
られ、通常、厚み0.05〜0.3mmで気孔度40〜
97%の微細な連続気泡を有するものである。The stretched porous tetrafluoroethylene resin sheet or film of component (c) of the present invention is, for example,
Examples include those manufactured by the method described in Japanese Patent No. 991, and usually have a thickness of 0.05 to 0.3 mm and a porosity of 40 to 40.
It has 97% fine open cells.
上記で調製した本樹脂溶液を(c)成分の延伸多孔質四
弗化エチレン樹脂シートもしくはフィルムである基材に
含浸した後、120〜170℃、1〜20分間乾繰して
溶剤を除去し、未硬化の溶剤の無いものとするか、所謂
r[i−1−5ta J化する。本接着用プリプレグの
樹脂量は、全重量に対して 30〜80重量%の範囲か
ら選択する。After impregnating the resin solution prepared above into a base material, which is a stretched porous polytetrafluoroethylene resin sheet or film (component (c)), the solvent was removed by drying at 120 to 170°C for 1 to 20 minutes. , uncured solvent-free, or so-called r[i-1-5ta J. The amount of resin in the adhesive prepreg is selected from a range of 30 to 80% by weight based on the total weight.
以上、説明した本発明の成分(a)、(b)を必須成分
とする樹脂組成物を含浸・乾繰してなる接着用プリプレ
グはそのままでも加熱により硬化するが、硬化を促進す
る目的で触媒或いは硬化剤を配合する。As described above, the adhesive prepreg obtained by impregnating and drying the resin composition containing the components (a) and (b) of the present invention as essential components can be cured by heating as it is, but a catalyst is used to accelerate the curing. Alternatively, a curing agent may be added.
このような化合物としては、過酸化ベンゾイル、ラウロ
イルパーオキサイド、カプリルバートキサイド、アセチ
ルパーオキサイド、パラクロロベンゾイルパーオキサイ
ド、ジーtert−ブチルージーパーフタレート等で例
示される有機過酸化物;アゾビスニトリル等のアゾ化合
物;2−メチルイミダゾール、2−ウンデシルイミダゾ
ール、2−ヘプタデシルイミダゾール、2−フェニルイ
ミダゾール、2−エチル−4−メチルイミダゾール、1
−ベンジル−2−メチルイミダゾール、1−プロピル−
2−メチルイミダゾール、1−シアノエチル−2−メチ
ルイミダゾール、1−シアノエチル−2−エチルイミダ
ゾール、1−シアノエチル−2−ウンデシルイミダゾー
ル、1−シアノエチル−2−フェニルイミダゾール、1
−シアノエチル−2−エチル−4−メチルイミダゾール
、1−グアナミンエチル−2−メチルイミダゾールで例
示されるイミダゾール類、さらには、これらのイミダゾ
ール類へのカルボン酸もしくはその無水物類の付加体な
ど;N、N−ジメチルベンジルアミン、N、 N−ジメ
チルアニリン、N、N−ジメチルトルイジン、NlN−
ジメチル−p−アニシジン、p−ハロゲノ−N、N−ジ
メチルアニリン、2−N−二チルアニリノエタノール、
トリーn−ブチルアミン、ピリジン、キノリン、N−メ
チルモルホリン、トリエタノールアミン、トリエチレン
ジアミン、N、 N、 N’ 、 N’−テトラメチル
ブタンジアミン、N−メチルピペリジンなどの第3級ア
ミン類;フェノール、キシレノール、クレゾール、レゾ
ルシン、カテコール、フロログリシンなどのフェノール
類;ナフテン酸鉛、ステアリン酸鉛、ナフテン酸亜鉛、
オクチル酸亜鉛、オレイン酸錫、ジブチル錫マレート、
ナフテン酸マンガン、ナフテン酸コバルト、アセチルア
セトン鉄などの有機金属塩; 5nC14、ZnCl2
、AlCl3などの無機金属塩;無水マレイン酸、無水
フタル酸、無水ラウリル酸、無水ピロメリット酸、無水
トリメリット酸、ヘキサヒドロ無水フタル酸、ヘキサヒ
ドロ無水トリメリット酸、ヘキサヒドロ無水ピロメリッ
ト酸などの酸無水物等が挙げられる。本発明における重
合開始剤と熱硬化触媒との添加量は、一般的な意味での
触媒量の範囲で充分であり、たとえば全組成物に対して
10wt%以下、通常、数%以下の量で使用される。Such compounds include organic peroxides such as benzoyl peroxide, lauroyl peroxide, caprylic peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl di-perphthalate; azobisnitrile; Azo compounds such as 2-methylimidazole, 2-undecylimidazole, 2-heptadecyl imidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 1
-benzyl-2-methylimidazole, 1-propyl-
2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1
-Imidazoles exemplified by cyanoethyl-2-ethyl-4-methylimidazole and 1-guanamineethyl-2-methylimidazole, as well as adducts of carboxylic acids or their anhydrides to these imidazoles; N , N-dimethylbenzylamine, N, N-dimethylaniline, N, N-dimethyltoluidine, NlN-
Dimethyl-p-anisidine, p-halogeno-N, N-dimethylaniline, 2-N-ditylanilinoethanol,
Tertiary amines such as tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, N, N, N', N'-tetramethylbutanediamine, N-methylpiperidine; phenol, Phenols such as xylenol, cresol, resorcin, catechol, phloroglycin; lead naphthenate, lead stearate, zinc naphthenate,
Zinc octylate, tin oleate, dibutyltin malate,
Organic metal salts such as manganese naphthenate, cobalt naphthenate, iron acetylacetonate; 5nC14, ZnCl2
, AlCl3; acid anhydrides such as maleic anhydride, phthalic anhydride, lauric anhydride, pyromellitic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, hexahydrotrimellitic anhydride, hexahydropyromellitic anhydride Examples include things. In the present invention, the amount of the polymerization initiator and thermosetting catalyst to be added is sufficient within the range of the catalyst amount in a general sense, for example, an amount of 10 wt% or less, usually several % or less, based on the total composition. used.
本発明の接着用プリプレグを用いて、他の基体と接着し
、シート、板など及び接着構造物などを製造するための
硬化条件は、硬化剤や触媒・組成成分の種類などによっ
ても変化するが、通常100〜300℃の範囲で選ばれ
ればよい。加熱硬化に際して圧力を加えることが好まし
く、一般的に言って0.1〜100 kg / csl
、好ましくは5〜50kg/C[+!の範囲内で適宜選
ばれる。又、積層成形にあたっては、100mm11g
以下の酔うな実質的に真空状態で積層成形する方法も好
適である。The curing conditions for manufacturing sheets, plates, etc., adhesive structures, etc. by adhering to other substrates using the adhesive prepreg of the present invention vary depending on the type of curing agent, catalyst, composition components, etc. , usually selected within the range of 100 to 300°C. It is preferable to apply pressure during heat curing, generally speaking 0.1 to 100 kg/csl
, preferably 5 to 50 kg/C [+! be selected as appropriate within the range. In addition, for lamination molding, 100 mm 11 g
The following method of lamination molding in a substantially vacuum state is also suitable.
以下、実施例、比較例によって本発明をさらに具体的に
説明する。尚、実施例、比較例中の部、%は特に断らな
い限り重量部である。Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples. Note that parts and percentages in Examples and Comparative Examples are parts by weight unless otherwise specified.
実施例−1
2,2−ビス(4−シアナトフェニル)プロパン 60
部を160℃で4時間予備反応させてプレポリマーとし
た。このプレポリマーに実質的に非結晶性の熱可塑性飽
和ポリエステル樹脂(商品名:ポリエスタ−LP−03
5、日本合成化学工業01製、末端官能基数より算出さ
れる数平均分子ffi 16,000 、水酸基価6m
g KOII/ g ) 25部、さらにビスフェノー
ルA型エポキシ樹脂(商品名:エピコート828、油化
シェルエポキシQ↑)製)15部を加え、メチルエチル
ケトン(以下、)、l E Kという)に溶解混合し、
濃度30%の溶液とした(フェス(a)という)。Example-1 2,2-bis(4-cyanatophenyl)propane 60
A prepolymer was obtained by preliminarily reacting a portion at 160° C. for 4 hours. This prepolymer is a substantially non-crystalline thermoplastic saturated polyester resin (trade name: Polyester-LP-03).
5. Manufactured by Nippon Gosei Kagaku Kogyo 01, number average molecule ffi 16,000 calculated from the number of terminal functional groups, hydroxyl value 6m
g KOII/g ) and 15 parts of bisphenol A type epoxy resin (product name: Epicote 828, Yuka Shell Epoxy Q ,
A solution with a concentration of 30% was prepared (referred to as FES (a)).
このフェス(a)を、厚み0.060mm、気孔度68
%の延伸多孔質四フッ化エチレン樹脂フィルムに含浸し
、150℃で5分間加熱し、樹脂量60%、ゲル化時間
2.4分(at 170℃)のプリプレグを得た。This face (a) has a thickness of 0.060 mm and a porosity of 68
% stretched porous tetrafluoroethylene resin film and heated at 150° C. for 5 minutes to obtain a prepreg with a resin content of 60% and a gelation time of 2.4 minutes (at 170° C.).
厚み1.0mmのアルミニウム板の上に、上記で得たプ
リプレグを1枚、その上に厚み35ρの銅箔を置き、1
70℃、2時間、25kg / Cntの条件で積層成
形し、厚み1.095m+nの銅張板を得た。Place one prepreg obtained above on an aluminum plate with a thickness of 1.0 mm, and place a copper foil with a thickness of 35ρ on top of it.
Lamination molding was carried out under the conditions of 25 kg/Cnt at 70° C. for 2 hours to obtain a copper clad plate with a thickness of 1.095 m+n.
この銅張板の銅箔の引剥し強度は2.1kg / cm
、半田耐熱性は300℃で2分以上で異常無し、表面抵
抗は3X10′4Ωであった。The peel strength of the copper foil of this copper clad board is 2.1 kg/cm
The soldering heat resistance was maintained at 300° C. for 2 minutes or more without any abnormality, and the surface resistance was 3×10′4Ω.
実施例−2
実施例−1において、フェス(a)を、厚み0.090
mm、気孔度68%の延伸多孔質四フッ化エチレン樹脂
フィルムに含浸し、150℃で5分間加熱し、樹脂量6
1%、ゲル化時間2.1分(at 170℃)のプリプ
レグを得た。Example-2 In Example-1, the face (a) has a thickness of 0.090
It was impregnated into a stretched porous polytetrafluoroethylene resin film with a porosity of 68% and heated at 150°C for 5 minutes to reduce the amount of resin to 68%.
A prepreg with a gelation time of 1% and a gelation time of 2.1 minutes (at 170°C) was obtained.
銅箔厚み35JU、厚み0.8mmの両面銅張ガラス布
基材エポキシ樹脂積層板の片面に、ICチップ接続端子
を有する配線網をフォトエツチング法により形成し、こ
のプリント配線板の上に上記プリプレグ所定位置に8m
m角の孔を明けしたもの、次いで厚み0.8化の片面銅
張ガラス布基材エポキシ樹脂積層板の所定位置に8mm
角の孔を明けしたものを位置合わせして重ね、圧力30
kg/co?、 170℃で2時間加熱硬化した。A wiring network having IC chip connection terminals is formed on one side of a double-sided copper-clad glass cloth base epoxy resin laminate with a copper foil thickness of 35 JU and a thickness of 0.8 mm by photoetching, and the above prepreg is placed on this printed wiring board. 8m in place
Drill an m square hole, then place an 8 mm hole in a predetermined position on a single-sided copper-clad glass cloth base epoxy resin laminate with a thickness of 0.8 mm.
Align and overlap the pieces with holes in the corners, and apply pressure to 30
kg/co? , Heat curing was carried out at 170°C for 2 hours.
次いで、得られた多層板の所定位置に貫通孔を明け、I
Cチップ用端子部に保護膜を塗布して、公知方法でスル
ーホール板を得た。Next, through holes were made at predetermined positions in the obtained multilayer board, and I
A protective film was applied to the terminal portion for the C chip, and a through-hole plate was obtained by a known method.
この多層板の8m+n角孔部への本プリプレグからの樹
脂のしみだし距離は0.08mmであった。又、半田耐
熱性は300℃で60秒以上で異常無しであった。The distance at which the resin seeped out from the prepreg into the 8m+n square holes of this multilayer board was 0.08 mm. Further, the soldering heat resistance was maintained at 300° C. for 60 seconds or more without any abnormality.
実施例−3
2,2−ビス(4−シアナトフェニル)プロパン 50
部とビス(4−マレイミドフェニル)メタン5部とを1
60℃で2時間予備反応させてプレポリマーとした。こ
れに実施例−1と同様のポリエステル樹脂 20部、ビ
スフェノールA型エポキシ樹脂(商品名:エビコート1
001 、融点68℃、エポキシ当量450〜500、
油化シェルエポキシ■製)20部、更に反応性の末端ビ
ニル基含有アクリロニトリル−ブタジェンゴム(商品名
; VTBNX 、粘度2.8×10’cPS at
27℃、アクリリックビニル基3.8%、アクリロニト
リル結合16.2%、宇部興産G→製)5部を加え、メ
チルエチルケトン(以下、MEKという)に溶解混合し
、濃度40%の溶液とした(フェスの)という)。Example-3 2,2-bis(4-cyanatophenyl)propane 50
1 part and 5 parts of bis(4-maleimidophenyl)methane.
A prepolymer was prepared by pre-reacting at 60° C. for 2 hours. To this, 20 parts of the same polyester resin as in Example-1, bisphenol A type epoxy resin (trade name: Ebicoat 1
001, melting point 68°C, epoxy equivalent 450-500,
(manufactured by Yuka Shell Epoxy ■), 20 parts of reactive acrylonitrile-butadiene rubber containing terminal vinyl groups (trade name: VTBNX, viscosity 2.8 x 10'cPS at)
At 27°C, 5 parts of acrylic vinyl group 3.8%, acrylonitrile bond 16.2%, manufactured by Ube Industries G→) were added, dissolved and mixed in methyl ethyl ketone (hereinafter referred to as MEK) to make a solution with a concentration of 40% (Fes ).
このフェス(b)に、触媒として、オクチル酸亜鉛0.
04部を加え均一に混合し、厚み0.10mm、気孔度
68%の延伸多孔質口フッ化エチレン樹脂フィルムに含
浸し、140℃で7分間加熱し、樹脂量55%、ゲル化
時間2.5分(at 170℃)のプリプレグを得た。To this phase (b), 0.0% zinc octylate was added as a catalyst.
04 parts were added and mixed uniformly, impregnated into a stretched porous fluorinated ethylene resin film with a thickness of 0.10 mm and a porosity of 68%, and heated at 140°C for 7 minutes to obtain a resin amount of 55% and a gelation time of 2. A prepreg was obtained for 5 minutes (at 170°C).
厚み0.8mmのアラミド繊維布基材口フッ化エチレン
樹脂銅張積層板の片面に公知方法で所定の配線網を形成
し7た後、金属す) IJウム系のフッ素樹脂用の表面
処理液で表面処理した。After forming a predetermined wiring network on one side of a fluorinated ethylene resin copper-clad laminate with a thickness of 0.8 mm using a known method, a surface treatment liquid for IJium-based fluororesin is applied. The surface was treated with
この積層板上に、上記で得たプリプレグ、厚み351の
銅箔を重ね、170℃、30kg/cafで90分間積
層成形し、再び、所定位置に所定の配線網を形成し、上
記で得たプリプレグを重ね積層成形する方法を繰り返し
て内層が4層で外層が銅箔の多層シールド板を得、貫通
孔を開け、公知方法でスルーホールメッキ、エツチング
を行い多層プリント板を製造した。On this laminate, the prepreg obtained above and the copper foil with a thickness of 351 were stacked and laminated at 170°C and 30 kg/caf for 90 minutes, and a predetermined wiring network was formed at a predetermined position again. A multilayer shield plate with four inner layers and a copper foil outer layer was obtained by repeating the method of overlapping and laminating prepregs, and a multilayer printed board was produced by punching through holes and through-hole plating and etching using known methods.
用いたプリプレグの硬化物の誘電率は2.8 (IMH
z)、誘電正接は0.0050 (IMHz)であり、
多層プリント板の半田耐熱性は60秒以上(280℃)
であった。The dielectric constant of the cured prepreg used was 2.8 (IMH
z), the dielectric loss tangent is 0.0050 (IMHz),
The soldering heat resistance of multilayer printed boards is 60 seconds or more (280℃)
Met.
以上、詳細な説明及び実施例から明白な如く、本発明の
接着用プリプレグは、優れた接着力、電気特性、耐熱性
等を持ち、樹脂流れも極めて小さく、かつ、多層化積層
成形に於ける配線用金属箔の埋め込み性も優れlこもの
であり、多層プリント板の層間接着や表層金属箔の接着
用プリプレグ、半導体チップ装着用の凸部及びその凸部
周囲に一段以上の電極用端子部を有する多層プリント板
の多層化接着用プリプレグ、金属箔張金属芯積層板用の
金属箔接着用プリプレグ、熱放散用の金属板接着用プリ
プレグ、可撓性のプリント配線板、半硬化金属箔付プリ
プレグなどに好適に使用されるものである。As is clear from the above detailed description and examples, the adhesive prepreg of the present invention has excellent adhesive strength, electrical properties, heat resistance, etc., has extremely small resin flow, and is suitable for multilayer lamination molding. The embeddability of metal foil for wiring is also excellent, and it is suitable for interlayer adhesion of multilayer printed boards, prepreg for adhesion of surface metal foil, convex parts for mounting semiconductor chips, and one or more stages of electrode terminals around the convex parts. Pre-preg for multi-layer adhesion of multi-layer printed boards, prepreg for adhesion of metal foil for metal-foil-clad metal-core laminates, prepreg for adhesion of metal plates for heat dissipation, flexible printed wiring boards, prepreg with semi-hardened metal foil It is suitably used for such purposes.
Claims (1)
シアン酸エステル樹脂組成物と (b)実質的に非結晶性の熱可塑性飽和ポリエステル樹
脂とを必須成分とする熱硬化性樹脂組成物の溶液を (c)延伸多孔質四弗化エチレン樹脂シートもしくはフ
ィルムに含浸し、乾燥し、樹脂成分を半硬化状態として
なることを特徴とする接着用プリプレグ。[Claims] The essential components are (a) a polyfunctional cyanate ester resin composition containing two or more cyanato groups in the molecule, and (b) a substantially non-crystalline thermoplastic saturated polyester resin. (c) A stretched porous tetrafluoroethylene resin sheet or film is impregnated with a solution of a thermosetting resin composition, and dried to bring the resin component into a semi-cured state.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22482786A JPS6381139A (en) | 1986-09-25 | 1986-09-25 | Prepreg for bonding |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22482786A JPS6381139A (en) | 1986-09-25 | 1986-09-25 | Prepreg for bonding |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6381139A true JPS6381139A (en) | 1988-04-12 |
Family
ID=16819815
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22482786A Pending JPS6381139A (en) | 1986-09-25 | 1986-09-25 | Prepreg for bonding |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6381139A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6500529B1 (en) | 2001-09-14 | 2002-12-31 | Tonoga, Ltd. | Low signal loss bonding ply for multilayer circuit boards |
US6783841B2 (en) | 2001-09-14 | 2004-08-31 | Tonoga, Inc. | Low signal loss bonding ply for multilayer circuit boards |
JP2008201124A (en) * | 2007-01-24 | 2008-09-04 | Hitachi Chem Co Ltd | Laminated material for electric insulation, and printed wiring board using laminated material |
WO2024075480A1 (en) * | 2022-10-04 | 2024-04-11 | 三菱瓦斯化学株式会社 | Thermosetting resin composition, cured product of same, prepreg, fiber-reinforced composite material, and high-pressure gas container |
-
1986
- 1986-09-25 JP JP22482786A patent/JPS6381139A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6500529B1 (en) | 2001-09-14 | 2002-12-31 | Tonoga, Ltd. | Low signal loss bonding ply for multilayer circuit boards |
US6783841B2 (en) | 2001-09-14 | 2004-08-31 | Tonoga, Inc. | Low signal loss bonding ply for multilayer circuit boards |
US6861092B2 (en) | 2001-09-14 | 2005-03-01 | Tonoga, Inc. | Low signal loss bonding ply for multilayer circuit boards |
JP2008201124A (en) * | 2007-01-24 | 2008-09-04 | Hitachi Chem Co Ltd | Laminated material for electric insulation, and printed wiring board using laminated material |
JP2013173368A (en) * | 2007-01-24 | 2013-09-05 | Hitachi Chemical Co Ltd | Laminated material for electric insulation, and printed wiring board using the laminated material |
WO2024075480A1 (en) * | 2022-10-04 | 2024-04-11 | 三菱瓦斯化学株式会社 | Thermosetting resin composition, cured product of same, prepreg, fiber-reinforced composite material, and high-pressure gas container |
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