JPH0158207B2 - - Google Patents
Info
- Publication number
- JPH0158207B2 JPH0158207B2 JP5709281A JP5709281A JPH0158207B2 JP H0158207 B2 JPH0158207 B2 JP H0158207B2 JP 5709281 A JP5709281 A JP 5709281A JP 5709281 A JP5709281 A JP 5709281A JP H0158207 B2 JPH0158207 B2 JP H0158207B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- vinyl
- dimaleimide
- peroxide
- resin
- 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.)
- Expired
Links
- -1 N-vinyl-pyrrolidone compound Chemical class 0.000 claims description 22
- 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 claims description 8
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 7
- 239000011342 resin composition Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229920006015 heat resistant resin Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920006337 unsaturated polyester resin Polymers 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
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229940120693 copper naphthenate Drugs 0.000 description 2
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010438 heat treatment Methods 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- 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
- NAWAHSSRMQMAFB-UHFFFAOYSA-N (4-acetyloxy-3,6-dioxocyclohexa-1,4-dien-1-yl) acetate Chemical compound CC(=O)OC1=CC(=O)C(OC(C)=O)=CC1=O NAWAHSSRMQMAFB-UHFFFAOYSA-N 0.000 description 1
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- ZPOUDMYDJJMHOO-UHFFFAOYSA-N 1-(1-hydroxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(O)CCCCC1 ZPOUDMYDJJMHOO-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- OEUTXEVXKFXZPB-UHFFFAOYSA-N 1-[12-(2,5-dioxopyrrol-1-yl)dodecyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCCCCCCCN1C(=O)C=CC1=O OEUTXEVXKFXZPB-UHFFFAOYSA-N 0.000 description 1
- PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 1
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 description 1
- VWGJOEJUQXVFPK-UHFFFAOYSA-N 1-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCN1C(=O)C=CC1=O VWGJOEJUQXVFPK-UHFFFAOYSA-N 0.000 description 1
- LNAIBNHJQKDBNR-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)-2-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=C(N2C(C=CC2=O)=O)C=CC=C1N1C(=O)C=CC1=O LNAIBNHJQKDBNR-UHFFFAOYSA-N 0.000 description 1
- FJKKJQRXSPFNPM-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(N2C(C=CC2=O)=O)C=C1N1C(=O)C=CC1=O FJKKJQRXSPFNPM-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- FXEKNWLZNLIDNR-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)propyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCN1C(=O)C=CC1=O FXEKNWLZNLIDNR-UHFFFAOYSA-N 0.000 description 1
- WXXSHAKLDCERGU-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)butyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCN1C(=O)C=CC1=O WXXSHAKLDCERGU-UHFFFAOYSA-N 0.000 description 1
- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
- XAZPKEBWNIUCKF-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XAZPKEBWNIUCKF-UHFFFAOYSA-N 0.000 description 1
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- LYCKDYZIIOVFCX-UHFFFAOYSA-N 1-[[3-[(2,5-dioxopyrrol-1-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC(CN2C(C=CC2=O)=O)=C1 LYCKDYZIIOVFCX-UHFFFAOYSA-N 0.000 description 1
- XFRPTDABLAIJMY-UHFFFAOYSA-N 1-[[4-[(2,5-dioxopyrrol-1-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC(C=C1)=CC=C1CN1C(=O)C=CC1=O XFRPTDABLAIJMY-UHFFFAOYSA-N 0.000 description 1
- ZOZNCAMOIPYYIK-UHFFFAOYSA-N 1-aminoethylideneazanium;acetate Chemical compound CC(N)=N.CC(O)=O ZOZNCAMOIPYYIK-UHFFFAOYSA-N 0.000 description 1
- NAGSMIOYEJTYQT-UHFFFAOYSA-N 1-ethenyl-3,3,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)C(=O)N1C=C NAGSMIOYEJTYQT-UHFFFAOYSA-N 0.000 description 1
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- QYXHDJJYVDLECA-UHFFFAOYSA-N 2,5-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)C=C1C1=CC=CC=C1 QYXHDJJYVDLECA-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- VFEXYZINKMLLAK-UHFFFAOYSA-N 2-(trichloromethyl)oxirane Chemical compound ClC(Cl)(Cl)C1CO1 VFEXYZINKMLLAK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- PIUOYUWMRQKWGT-UHFFFAOYSA-N 2-methyl-2-(trichloromethyl)oxirane Chemical compound ClC(Cl)(Cl)C1(C)CO1 PIUOYUWMRQKWGT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- CPHURRLSZSRQFS-UHFFFAOYSA-N 3-[4-[2-[4-(3-hydroxypropoxy)phenyl]propan-2-yl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)(C)C1=CC=C(OCCCO)C=C1 CPHURRLSZSRQFS-UHFFFAOYSA-N 0.000 description 1
- NWVWKBFJWAALRI-UHFFFAOYSA-N 3-methyl-1-[2-(3-methyl-2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1CCN1C(=O)C(C)=CC1=O NWVWKBFJWAALRI-UHFFFAOYSA-N 0.000 description 1
- JOIKTXAWXLKFFD-UHFFFAOYSA-N 3-methyl-1-[4-[[4-(3-methyl-2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C(C)=CC2=O)=O)C=C1 JOIKTXAWXLKFFD-UHFFFAOYSA-N 0.000 description 1
- RVOLLKNEKYKCQB-UHFFFAOYSA-N 3-methyl-1-[6-(3-methyl-2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1CCCCCCN1C(=O)C(C)=CC1=O RVOLLKNEKYKCQB-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- YQLVIOYSGHEJDA-UHFFFAOYSA-N 3-methyloxane-2,6-dione Chemical compound CC1CCC(=O)OC1=O YQLVIOYSGHEJDA-UHFFFAOYSA-N 0.000 description 1
- AOCWQPKHSMJWPL-UHFFFAOYSA-N 3-methylpyrrolidin-2-one Chemical compound CC1CCNC1=O AOCWQPKHSMJWPL-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- 229910004762 CaSiO Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- AVGYVDOSBJFXFR-UHFFFAOYSA-N diphenyl sulfite Chemical compound C=1C=CC=CC=1OS(=O)OC1=CC=CC=C1 AVGYVDOSBJFXFR-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- NXOCXWBPHYAIGC-UHFFFAOYSA-N ethanimidamide;sulfuric acid Chemical compound CC(N)=N.OS(O)(=O)=O NXOCXWBPHYAIGC-UHFFFAOYSA-N 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- VGIYPVFBQRUBDD-UHFFFAOYSA-N ethenoxycyclohexane Chemical compound C=COC1CCCCC1 VGIYPVFBQRUBDD-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 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
- 239000011159 matrix material Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- ABTNKPAZMOYEAS-UHFFFAOYSA-N oxo-bis(prop-2-enoxy)phosphanium Chemical compound C=CCO[P+](=O)OCC=C ABTNKPAZMOYEAS-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003865 secondary ammonium salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は耐熱性にすぐれた樹脂に転化する熱硬
化性樹脂組成物に関する。
近年電気機器ならびに電子機器の大容量化、小
型軽量化あるいは高信頼性化に伴ない、耐熱性に
すぐれた絶縁材料が要求されている。
そのような耐熱性樹脂としては、高温において
高い安定性と強度とを保持する点で、ポリイミド
を代表とするヘテロ環ポリマーが秀でている。し
かしそれらは一般に重縮合型であり、硬化時に揮
発生物質を放出するとか、溶融成形しにくいとい
うことなどのために、成形材料、積層材あるいは
塗膜形成用粉体材料などとしての応用が制約され
ている。このような欠点を改善するために、付加
重合型イミド化合物例えばビスマレイミドとエポ
キシ化合物、不飽和ポリエステルなどとを併用す
る提案がなされている。しかし、これらにおいて
も速硬化性、各種溶媒に対る溶解性、材料原価な
どに問題があつて、成形材料、プリプレグ材料、
塗膜形成用粉体材料、接着剤などの用途における
製品化を阻害していた。
本発明は、上述のような情況に鑑み、溶媒に対
する溶解性が良好であり、150〜200℃程度の温度
範囲に短時間加熱することによつて、高温強度に
すぐれた硬化物に転化できる熱硬化性樹脂組成物
を提供することを目的とする。その特徴は、
(a) 一般式
(式中R1は水素またはメチル基を表わし、
R2は2価の有機基を表わす)で示されるビス
マレイミドと、
(b) N―ビニル―ピロリドン系化合物
(c) ポリパラヒドロキシスチレン
を含む熱硬化性樹脂組成物である。
本発明において、(a)一般式
(式中R1は水素またはメチル基を表わし、R2は
2価の有機基を表わす)で示されるビスマレイミ
ドとしては、例えばN,N′―エチレンジマレイ
ミド、N,N′―エチレンビス〔2―メチルマレ
イミド〕、N,N′―トリメチレンジマレイミド、
N,N′―テトラメチレンジマレイミド、N,
N′―ヘキサメチレンジマレイミド、N,N′―ヘ
キサメチレンビス〔2―メチルマレイミド〕、N,
N′―ドデカメチレンジマレイミド、、N,N′―m
―フエニレンジマレイミド、N,N′―p―フエ
ニレンジマレイミド、N,N′―(オキシ―p―
フエニレン)ジマレイミド、N,N′―(メチレ
ン―ジ―p―フエニレン)ジマレイミド、N,
N′―(メチレン―ジ―p―フエニレン)ビス
〔2―メチルマレイミド〕、N,N′―2,4―ト
リレンジマレイミド、N,N′―2,6―トリレ
ンジマレイミド、N,N′―m―キシリレンジマ
レイミド、N,N′―p―キシリレンジマレイミ
ド、N,N′―オキシプロピレンジマレイミド、
N,N′―エチレンビス(オキシプロピレンマレ
イミド)、N,N′―オキシジエチレンジマレイミ
ドなどのN,N′―置換ビスマレイミドがあり、
単独もしくは2種以上あわせて使用される。
また、本発明に於いて、N―ビニル―ピロリド
ン系化合物(b)としては、例えば、N―ビニル―2
―ピロリドン、N―ビニル―2―ピペリドン、N
―ビニル―ε―カプロダクタム、N―ビニル―5
―メチル―2―ピロリドン、N―ビニル―3,
3,5―トリメチル―2―ピロリドン、3―メチ
ル―2―ピロリドン、あるいは、N―ビニル―2
―ピロリドンの2量体、また、N―ビニル―ピロ
リドンと、アクリロニトル、アリルアルコール、
アリルアセテート、エチレン、無水マレイン酸、
メチルメタクリレート、スチレン、ビニルアセテ
ート、ビニルクロライド、ビニレンカーボネー
ト、ビニルシクロヘキシルエーテル、ビニルフエ
ニルエーテルなどの共重合体、あるいはまた、ポ
リビニルピロリドンなどがあり、それらの1種以
上を併用して使用することができる。
本発明において、前記ビスマレイミド(a)と、N
―ビニル―ピロリドン系化合物(b)とは、重量比1
対9ないし9対1の範囲で使用できる。ビスマレ
イミド(a)が多くなると、組成物の流動性が低下
し、成形加工性が悪くなり、少なくなると、耐熱
性が低下する。
一層好ましい重量比は1対4ないし4対1であ
る。
また、ポリパラヒドロキシスチレン系の化合物
(c)としては、一般式
で示される、平均分子量500〜10000の化合物であ
り、丸善石油(株)より市販されているNレジン、あ
るいは、Mレジンとジエン系化合物の共重合体が
用いられる。
ポリパラヒドロキシスチレン系化合物の配合割
合としては、前記、ビスマレイミド(a)と、N―ビ
ニルピロリドン系化合物(b)との和で100重量部に
対して、10〜1000重量部の範囲で用いれば本発明
の目的とする硬化物を得ることが出来る。
また、本発明の樹脂組成物には不飽和ポリエス
テル樹脂を添加して使用してもよい。不飽和ポリ
エステル樹脂としては、不飽和二塩基酸、飽和二
塩基酸およびその無水物またはこれらの低級アル
キルエステル誘導体等とジオールまたはアルキル
レンモノオキサイドおよびその誘導体等から、触
媒の存在または不存在下にエステル化、エステル
交換等の反応を利用して縮合または付加重合する
ことによつて合成された不飽和基を含有するポリ
エステル樹脂母体と、エチレン系(例えばビニル
基、アリル基等)の重合性化合物、ならびに過酸
化物触媒との混合物からなるものである。この他
に、ビスフエノールA型ならびにノボラツク型等
のエポキシ化合物とメタアクリル酸またはアクリ
ル酸と反応して得られるビニルエステル系樹脂も
有用である。ここで、前記不飽和二塩基酸、飽和
二塩基酸の代表的なものとしてはマレイン酸、無
水マレイン酸、フマール酸、クロロマレイン酸、
ジクロロマレイン酸、シトラコン酸、無水シトラ
コン酸、メサコン酸、メタコン酸、コハク酸、ア
ジピン酸、セバシン酸、アゼライン酸、フタール
酸、無水フタール酸、イソフタール酸、テレフタ
ール酸、無水メチルグルタル酸、ピメリン酸、ヘ
キサヒドロフタル酸および無水物、テトラヒドロ
フタル酸、無水カーピツク酸、ヘツト酸およびそ
の無水物、テトラクロロフタール酸およびその無
水物、テトラブロムフタール酸およびその無水
物、これらの低級アルキルエステル等が使用さ
れ、ジオール成分としてはエチレングリコール、
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、プロピレングリコ
ール、ジプロピレングリコール、トリメチレング
リコール、テトラメチレングリコール、ヘキサメ
チレングリコール、2,2―ジエチルプロパンジ
オール1,3,ネオペンチルグリコール、ジグロ
ムネオペンチルグリコール、ピスフエノールジオ
キシエチルエーテル、水素化ビスフエノールA、
2,2―ジ(4―ヒドロキシプロポキシフエニ
ル)プロパン、エチレンオキサイド、プロピレン
オキサイド、3,3,3―トリクロロプロピレン
オキサイド、2―メチル―3,3,3―トリクロ
ロプロピレンオキサイド、フエニールグリシジー
ルエーテル、アリルグリジルエーテル等が使用さ
れる。また、必要に応じ、本発明の目的を損なわ
ない範囲で、3官能以上の多塩基酸およびまたは
多価アルコールを併用してもよい。
架橋剤としては例えばスチレン、ビニルトルエ
ン、α―メチルスチレン、ジビニルベンゼン、ジ
アリルフタレート、ジアリルフタレートプレポリ
マー、クロルスチレン、ジクロルスチレン、ブロ
ムスチレン、ジブロムスチレン、ジアリルベンゼ
ンホスホネート、ジアリルアリールホスフイル酸
エステル、アクリル酸エステル、メタアクリル酸
エステル、トリアリルシアヌレート、トリブロモ
フエノールアリルエーテルなどが用いられる。本
発明において、酸成分、アルコール成分、架橋剤
は1種に限定するものではなく2種以上の併用も
可能である。また各種の変性および変性剤の添加
も可能である。また、不飽和ポリエステル樹脂も
1種に限定するものではなく2種以上の混合も可
能である。
また、本発明の樹脂組成物には重合開始剤を添
加することが出来る。例えば、ベンゾイルパーオ
キシド、パラクロロベンゾイルパーオキシド、
2,4―ジクロロベンゾイルパーオキシド、カブ
リリルパーオキシド、ラウロイルパーオキシド、
アセチルパーオキシド、メチルエチルケトンパー
オキシド、シクロヘキサノンパーオキシド、ビス
(1―ヒドロキシシクロヘキシルパーオキシド)、
ヒドロキシヘブチルパーオキシド、t―ブチルハ
イドロパーオキシド、p―メンタンハイドロパー
オキシド、クメンハイドロパーオキシド、2,5
―ジメチルヘキシル―2,5―ジヒドロパーオキ
シド、ジターシヤリ―ブチルパーオキシド、ジク
ミルパーオキシド、2,5―ジメチル―2,5ジ
(t―ブチルパーオキシ)ヘキサン、2,5―ジ
メチルヘキシル―2,5―ジ(パオキシベンゾエ
ート)、t―ブチルパーベンゾエート、t―ブチ
ルパーアセテート、t―ブチルパーオクトエー
ト、t―ブチルパーオキシイリブチレート、ジ―
t―ブチルジ―パーフタレート等の有機過酸化物
の1種または2種以上を併用して用いることが出
来る。
また、本発明では上述の触媒と以下の様な公知
の促進剤を併用することも可能である。即ち、ラ
ウリルメリカプタン、N―ブチルサルフアイト、
ジフエニルサルフアイト、p―トルエンスルホン
酸、第4級アンモニウム塩、β―ジケトン類、過
酢酸型エポキシ化合物、スルホニウム塩類、亜硫
酸ガス、硫化水素、ナフテン酸マンガン、オクト
エ酸バナジル、ナフテン酸銅、ナフテン酸カルシ
ウム、その他ナフテン酸の金属塩、金属キレート
化合物、アミン類、含リン化合物、含硫黄化合物
である。また、以下の様な重合防止剤を使用する
こともできる。例えばp―ベンゾキノン、ナフト
キノン、フエナンスラキノン、パラキシロキノ
ン、2,5―ジフエニル―p―ベンゾキノン、
2,5―ジアセトキシ―p―ベンゾキノンなどの
キノン類、ハイドロキノン、p―t―ブチルカテ
コール、2,5―ジ―t―ブチルハイドロキノ
ン、モノ―t―ブチルハイドロキノンなどのハイ
ドロキノン類、ジ―t―ブチル、パラクレゾー
ル、ハイドロキノンモノメチルエーテル、アルフ
アナフトール等のフエノール類、ナフテン酸銅な
どの有機ならびに無機の銅塩、アセトアミジンア
セテート、アセトアミジンサルフエートなどのア
ミジン類、フエニルヒドラジン塩酸塩、ヒドラジ
ン塩酸塩などのヒドラジン塩類、その他第級アン
モニウム塩類、アミン類、ニトロ化合物、オキシ
ム類、硫黄、多価フエノール類、アミン塩酸塩類
を使用することができる。
更に、本発明の樹脂組成物には、目的を損なわ
ない範囲で、例えばポリエチレン、ポリスチレ
ン、フエノール樹脂、エポキシ樹脂、メラミン樹
脂あるいは尿素樹脂、フツ素樹脂など公知の樹脂
用改質剤、ステアリン酸、ステアリン酸亜鉛、ス
テアリン酸カルシウム、ヘキストワツクス、カル
ナバワツクスなどの離型剤、樹脂と充填剤とのカ
ツプリング効果有するビニルシラン、エポキシシ
ラン、アミノシランなどのカツプリング剤、ある
いはチタン酸、酸化クロム、群青、弁柄、カーボ
ンブラツクなどの着色剤、酸化マグネシウムなど
の増粘剤、シラノール基を持つた10〜20mμの無
水ケイ酸などの揺変剤を配合することもできる。
次に本発明について実施例を示し具体的に説明
する。尚、以下の各例φに部とあるのは重量部を
意味する。
実施例 1〜5
N,N′―(メチレン―ジ―p―フエニレン)
ジマレイミドと、N―ビニル―2―ピロリドン
と、ポリパラヒドロキシルスチレン(丸善石油製
PHP―113、平均分子量1700)とを、表1に示す
所定配合量の種類の配合物を作つた。これに、ジ
クミルパーオキシド(DCPO)3重量部を加え、
50〜80℃で加熱状態で、撹域混合した後、曲げ試
験用金型に、上記配合物を流し込み、200℃、3
時間硬化した。試片をを150℃で、曲げ強さを測
定した。また、240℃で、30日放置後の曲げ強さ
の保持率を示した。
The present invention relates to a thermosetting resin composition that is converted into a resin with excellent heat resistance. In recent years, as electric and electronic devices have become larger in capacity, smaller and lighter, and more reliable, insulating materials with excellent heat resistance have been required. As such heat-resistant resins, heterocyclic polymers such as polyimide are excellent in that they maintain high stability and strength at high temperatures. However, they are generally polycondensation type, and their application as molding materials, laminated materials, or powder materials for coating film formation is limited because they emit volatile substances during curing and are difficult to melt and mold. has been done. In order to improve these drawbacks, proposals have been made to use addition-polymerizable imide compounds such as bismaleimide in combination with epoxy compounds, unsaturated polyesters, and the like. However, even with these, there are problems with fast curing, solubility in various solvents, material cost, etc., and molding materials, prepreg materials, etc.
This has hindered the commercialization of applications such as powder materials for coating film formation and adhesives. In view of the above-mentioned circumstances, the present invention aims to provide a heat-generating product that has good solubility in solvents and can be converted into a cured product with excellent high-temperature strength by heating to a temperature range of about 150 to 200°C for a short time. The purpose is to provide a curable resin composition. Its characteristics are: (a) General formula (In the formula, R 1 represents hydrogen or a methyl group,
R2 represents a divalent organic group); (b) an N-vinyl-pyrrolidone compound; and (c) polyparahydroxystyrene. In the present invention, (a) general formula (In the formula, R 1 represents hydrogen or a methyl group, and R 2 represents a divalent organic group.) Examples of the bismaleimide include N,N'-ethylene dimaleimide, N,N'-ethylenebis [ 2-methylmaleimide], N,N'-trimethylene dimaleimide,
N,N'-tetramethylene dimaleimide, N,
N'-hexamethylene dimaleimide, N,N'-hexamethylenebis[2-methylmaleimide], N,
N′-dodecamethylene dimaleimide, N,N′-m
-Phenylene dimaleimide, N,N'-p-phenylene dimaleimide, N,N'-(oxy-p-
phenylene) dimaleimide, N,N'-(methylene-di-p-phenylene) dimaleimide, N,
N'-(methylene-di-p-phenylene)bis[2-methylmaleimide], N,N'-2,4-tolylene dimaleimide, N,N'-2,6-tolylene dimaleimide, N,N' -m-xylylene dimaleimide, N,N'-p-xylylene dimaleimide, N,N'-oxypropylene dimaleimide,
There are N,N'-substituted bismaleimides such as N,N'-ethylenebis(oxypropylenemaleimide) and N,N'-oxydiethylene dimaleimide.
Used alone or in combination of two or more. In the present invention, the N-vinyl-pyrrolidone compound (b) includes, for example, N-vinyl-2
-pyrrolidone, N-vinyl-2-piperidone, N
-Vinyl-ε-caprodactum, N-vinyl-5
-Methyl-2-pyrrolidone, N-vinyl-3,
3,5-trimethyl-2-pyrrolidone, 3-methyl-2-pyrrolidone, or N-vinyl-2
- Dimer of pyrrolidone, also N-vinyl-pyrrolidone, acrylonitrile, allyl alcohol,
Allyl acetate, ethylene, maleic anhydride,
Copolymers such as methyl methacrylate, styrene, vinyl acetate, vinyl chloride, vinylene carbonate, vinyl cyclohexyl ether, vinyl phenyl ether, and polyvinylpyrrolidone are available, and one or more of these may be used in combination. can. In the present invention, the bismaleimide (a) and N
- Vinyl-pyrrolidone compound (b) has a weight ratio of 1
It can be used in the range of 9 to 1 to 9 to 1. When the amount of bismaleimide (a) increases, the fluidity of the composition decreases and moldability deteriorates, and when it decreases, the heat resistance decreases. A more preferred weight ratio is 1:4 to 4:1. In addition, polyparahydroxystyrene compounds
(c) is the general formula It is a compound having an average molecular weight of 500 to 10,000 and is commercially available from Maruzen Sekiyu Co., Ltd. N resin or a copolymer of M resin and a diene compound is used. The blending ratio of the polyparahydroxystyrene compound is 10 to 1000 parts by weight based on 100 parts by weight of the sum of the bismaleimide (a) and the N-vinylpyrrolidone compound (b). In this case, it is possible to obtain a cured product which is the object of the present invention. Furthermore, an unsaturated polyester resin may be added to the resin composition of the present invention. The unsaturated polyester resin is made of unsaturated dibasic acids, saturated dibasic acids and their anhydrides, or lower alkyl ester derivatives thereof, diols, alkylene monooxides, and derivatives thereof, etc., in the presence or absence of a catalyst. A polyester resin matrix containing an unsaturated group synthesized by condensation or addition polymerization using reactions such as esterification and transesterification, and an ethylene-based (e.g., vinyl group, allyl group, etc.) polymerizable compound , and a mixture with a peroxide catalyst. In addition, vinyl ester resins obtained by reacting epoxy compounds such as bisphenol A type and novolac type with methacrylic acid or acrylic acid are also useful. Here, typical unsaturated dibasic acids and saturated dibasic acids include maleic acid, maleic anhydride, fumaric acid, chloromaleic acid,
Dichloromaleic acid, citraconic acid, citraconic anhydride, mesaconic acid, methaconic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, methylglutaric anhydride, pimelic acid, Hexahydrophthalic acid and anhydride, tetrahydrophthalic acid, carpicic anhydride, Hett's acid and its anhydride, tetrachlorophthalic acid and its anhydride, tetrabromophthalic acid and its anhydride, lower alkyl esters thereof, etc. are used. , ethylene glycol as a diol component,
Diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, tetramethylene glycol, hexamethylene glycol, 2,2-diethylpropanediol 1,3, neopentyl glycol, diglomneopentyl glycol, pisphenol Dioxyethyl ether, hydrogenated bisphenol A,
2,2-di(4-hydroxypropoxyphenyl)propane, ethylene oxide, propylene oxide, 3,3,3-trichloropropylene oxide, 2-methyl-3,3,3-trichloropropylene oxide, phenyl glycidyl ether , allyl glycyl ether, etc. are used. Further, if necessary, a trifunctional or higher functional polybasic acid and/or a polyhydric alcohol may be used in combination within a range that does not impair the object of the present invention. Examples of crosslinking agents include styrene, vinyltoluene, α-methylstyrene, divinylbenzene, diallyl phthalate, diallyl phthalate prepolymer, chlorstyrene, dichlorostyrene, bromustyrene, dibromostyrene, diallylbenzenephosphonate, and diallyl phosphonate. , acrylic ester, methacrylic ester, triallyl cyanurate, tribromophenol allyl ether, etc. are used. In the present invention, the acid component, alcohol component, and crosslinking agent are not limited to one type, and two or more types can be used in combination. It is also possible to add various modifications and modifiers. Further, the unsaturated polyester resin is not limited to one type, but a mixture of two or more types is also possible. Moreover, a polymerization initiator can be added to the resin composition of the present invention. For example, benzoyl peroxide, parachlorobenzoyl peroxide,
2,4-dichlorobenzoyl peroxide, cabrylyl peroxide, lauroyl peroxide,
Acetyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, bis(1-hydroxycyclohexyl peroxide),
Hydroxyhebutyl peroxide, t-butyl hydroperoxide, p-menthane hydroperoxide, cumene hydroperoxide, 2,5
-dimethylhexyl-2,5-dihydroperoxide, ditertiary-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5 di(t-butylperoxy)hexane, 2,5-dimethylhexyl-2 , 5-di(paoxybenzoate), t-butyl perbenzoate, t-butyl peracetate, t-butyl peroctoate, t-butyl peroxyybutyrate, di-
One type or a combination of two or more types of organic peroxides such as t-butyl di-perphthalate can be used. Further, in the present invention, it is also possible to use the above-mentioned catalyst together with the following known promoters. Namely, lauryl mericcaptan, N-butyl sulfite,
Diphenyl sulfite, p-toluenesulfonic acid, quaternary ammonium salt, β-diketones, peracetic acid type epoxy compound, sulfonium salts, sulfur dioxide gas, hydrogen sulfide, manganese naphthenate, vanadyl octoate, copper naphthenate, naphthene These include calcium acid, other metal salts of naphthenic acid, metal chelate compounds, amines, phosphorus-containing compounds, and sulfur-containing compounds. Moreover, the following polymerization inhibitors can also be used. For example, p-benzoquinone, naphthoquinone, phenanthraquinone, paraxyloquinone, 2,5-diphenyl-p-benzoquinone,
Quinones such as 2,5-diacetoxy-p-benzoquinone, hydroquinones such as hydroquinone, pt-butylcatechol, 2,5-di-t-butylhydroquinone, mono-t-butylhydroquinone, di-t-butyl , paracresol, hydroquinone monomethyl ether, phenols such as alphanaphthol, organic and inorganic copper salts such as copper naphthenate, amidines such as acetamidine acetate, acetamidine sulfate, phenylhydrazine hydrochloride, hydrazine hydrochloride, etc. hydrazine salts, other secondary ammonium salts, amines, nitro compounds, oximes, sulfur, polyhydric phenols, and amine hydrochlorides can be used. Furthermore, the resin composition of the present invention may contain known resin modifiers such as polyethylene, polystyrene, phenolic resin, epoxy resin, melamine resin, urea resin, and fluorine resin, stearic acid, Mold release agents such as zinc stearate, calcium stearate, Hoechstwax, and carnauba wax; coupling agents such as vinylsilane, epoxysilane, and aminosilane that have a coupling effect between resin and filler; titanic acid, chromium oxide, ultramarine blue, and valves. Coloring agents such as handles and carbon black, thickeners such as magnesium oxide, and thixotropic agents such as silicic anhydride having a silanol group and a size of 10 to 20 mμ can also be added. Next, the present invention will be specifically explained by showing examples. In each of the following examples, parts in φ mean parts by weight. Examples 1 to 5 N,N'-(methylene-di-p-phenylene)
dimaleimide, N-vinyl-2-pyrrolidone, and polyparahydroxylstyrene (Maruzen Sekiyu Co., Ltd.)
PHP-113 (average molecular weight: 1700) was used to prepare blends in the predetermined amounts shown in Table 1. Add 3 parts by weight of dicumyl peroxide (DCPO) to this,
After stirring in a heating state at 50 to 80°C, the above mixture was poured into a bending test mold, and heated at 200°C for 30 minutes.
Time cured. The bending strength of the specimen was measured at 150°C. The retention rate of bending strength after being left at 240°C for 30 days was also shown.
【表】
実施例 6〜9
2,2―ビス〔4―(4―マレイミドフエノキ
シ)フエニル〕プロパンと、N―ビニル―2―ピ
ロリドンと、平均分子量の異なるポリパラヒドロ
キシスチレン(丸善石油製;PHP―031平均分子
量2200、PHP―040平均分子量8300)と、トリア
リルイソシアヌレート(TAIC)とを、第2表に
示した所定割合に配合した種類の組成物を作つ
た。
これらのそれぞれに、DCPO、カツプリング剤
KBM―503(信越化学製)、充填剤として、ウオ
ラストナイト(CaSiO3)、溶融石英ガラス粉とを
第2表に示した割合で配合した。
この組成物を、60〜80℃の2本ロールで10分間
混練して、目的の組成物を得た。
これらの組成物を、170℃、70Kg/cm2、1.5分間
の条件で曲げ試験片をトランスフア成形した。[Table] Examples 6 to 9 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, N-vinyl-2-pyrrolidone, and polyparahydroxystyrene with different average molecular weights (Maruzen Oil Co., Ltd.) A composition was prepared in which PHP-031 average molecular weight 2200, PHP-040 average molecular weight 8300) and triallyl isocyanurate (TAIC) were blended in the predetermined proportions shown in Table 2. Each of these includes DCPO, a coupling agent
KBM-503 (manufactured by Shin-Etsu Chemical), wollastonite (CaSiO 3 ) as a filler, and fused silica glass powder were blended in the proportions shown in Table 2. This composition was kneaded with two rolls at 60 to 80°C for 10 minutes to obtain the desired composition. These compositions were transfer-molded into bending test pieces under the conditions of 170° C., 70 kg/cm 2 , and 1.5 minutes.
【表】【table】
【表】【table】
Claims (1)
R2は2価の有機基を表わす)で示されるビス
マレイミドと、 (b) N―ビニル―ピロリドン系化合物 (c) ポリパラヒドロキシスチレン を含む熱硬化性樹脂組成物。 2 ビスマレイミドとN―ビニル―ピロリドン系
化合物との重量比が1対4ないし9対1である特
許請求の範囲第1項記載の耐熱性樹脂組成物。[Claims] 1 (a) General formula (In the formula, R 1 represents hydrogen or a methyl group,
R 2 represents a divalent organic group); (b) an N-vinyl-pyrrolidone compound; and (c) polyparahydroxystyrene. 2. The heat-resistant resin composition according to claim 1, wherein the weight ratio of bismaleimide to N-vinyl-pyrrolidone compound is from 1:4 to 9:1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5709281A JPS57172922A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5709281A JPS57172922A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57172922A JPS57172922A (en) | 1982-10-25 |
JPH0158207B2 true JPH0158207B2 (en) | 1989-12-11 |
Family
ID=13045853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5709281A Granted JPS57172922A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57172922A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0299545A (en) * | 1988-10-07 | 1990-04-11 | Hitachi Ltd | Thermosetting resin composition and prepreg and laminated board using the same |
-
1981
- 1981-04-17 JP JP5709281A patent/JPS57172922A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57172922A (en) | 1982-10-25 |
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