JPH0135846B2 - - Google Patents
Info
- Publication number
- JPH0135846B2 JPH0135846B2 JP5709181A JP5709181A JPH0135846B2 JP H0135846 B2 JPH0135846 B2 JP H0135846B2 JP 5709181 A JP5709181 A JP 5709181A JP 5709181 A JP5709181 A JP 5709181A JP H0135846 B2 JPH0135846 B2 JP H0135846B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- bis
- phenyl
- maleimidophenoxy
- acid
- 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 ester compound Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000011342 resin composition Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005462 imide group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000002253 acid Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 239000004641 Diallyl-phthalate Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 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 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
- 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 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 2
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 239000004693 Polybenzimidazole Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst 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
- 150000002431 hydrogen Chemical class 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
- 239000000178 monomer Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- 229920002480 polybenzimidazole Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-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
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical class C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 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
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-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
- XJBSYHZLEOIPEJ-UHFFFAOYSA-N 1-[4-[2,6-dibromo-4-[2-[3,5-dibromo-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C(Br)=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(Br)=CC=1C(C(F)(F)F)(C(F)(F)F)C(C=C1Br)=CC(Br)=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XJBSYHZLEOIPEJ-UHFFFAOYSA-N 0.000 description 1
- OGPFZTQPAAOEAG-UHFFFAOYSA-N 1-[4-[2-bromo-4-[1-[3-bromo-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]ethyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(Br)=CC=1C(C)C(C=C1Br)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O OGPFZTQPAAOEAG-UHFFFAOYSA-N 0.000 description 1
- QMQYJRMHXYICMD-UHFFFAOYSA-N 1-[4-[2-bromo-4-[2-[3-bromo-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(Br)=CC=1C(C)(C)C(C=C1Br)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O QMQYJRMHXYICMD-UHFFFAOYSA-N 0.000 description 1
- MKVPTXFTWXTKBN-UHFFFAOYSA-N 1-[4-[2-bromo-4-[[3-bromo-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]methyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(Br)=CC=1CC(C=C1Br)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O MKVPTXFTWXTKBN-UHFFFAOYSA-N 0.000 description 1
- ACJJFTVZJOVGSN-UHFFFAOYSA-N 1-[4-[2-butan-2-yl-4-[2-[3-butan-2-yl-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound CCC(C)C1=CC(C(C)(C)C=2C=C(C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)C(C)CC)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O ACJJFTVZJOVGSN-UHFFFAOYSA-N 0.000 description 1
- MSMRYSXMPLWMFH-UHFFFAOYSA-N 1-[4-[2-butyl-4-[2-[3-butyl-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound CCCCC1=CC(C(C)(C)C=2C=C(CCCC)C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O MSMRYSXMPLWMFH-UHFFFAOYSA-N 0.000 description 1
- LRLKRMWSHCJOQL-UHFFFAOYSA-N 1-[4-[2-chloro-4-[1-[3-chloro-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]ethyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(Cl)=CC=1C(C)C(C=C1Cl)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O LRLKRMWSHCJOQL-UHFFFAOYSA-N 0.000 description 1
- UTUDZIVGWZEXJH-UHFFFAOYSA-N 1-[4-[2-chloro-4-[2-[3-chloro-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(Cl)=CC=1C(C)(C)C(C=C1Cl)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O UTUDZIVGWZEXJH-UHFFFAOYSA-N 0.000 description 1
- TVIXEYAIMZLQSY-UHFFFAOYSA-N 1-[4-[2-chloro-4-[[3-chloro-4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]methyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(Cl)=CC=1CC(C=C1Cl)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O TVIXEYAIMZLQSY-UHFFFAOYSA-N 0.000 description 1
- LDQRVPVSQDLCBY-UHFFFAOYSA-N 1-[4-[4-[1,1,1,3,3,3-hexachloro-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(Cl)(Cl)Cl)(C(Cl)(Cl)Cl)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O LDQRVPVSQDLCBY-UHFFFAOYSA-N 0.000 description 1
- OJDDBNNNPILOKG-UHFFFAOYSA-N 1-[4-[4-[1-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-methylphenyl]ethyl]-2-methylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(C)=CC=1C(C)C(C=C1C)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O OJDDBNNNPILOKG-UHFFFAOYSA-N 0.000 description 1
- VZBQHKQTICAEPG-UHFFFAOYSA-N 1-[4-[4-[1-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]ethyl]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=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O VZBQHKQTICAEPG-UHFFFAOYSA-N 0.000 description 1
- UMMCCUYTTMFIPQ-UHFFFAOYSA-N 1-[4-[4-[1-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(CC)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O UMMCCUYTTMFIPQ-UHFFFAOYSA-N 0.000 description 1
- XRHJTQFPYUPMRJ-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-ethylphenyl]propan-2-yl]-2-ethylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound CCC1=CC(C(C)(C)C=2C=C(CC)C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XRHJTQFPYUPMRJ-UHFFFAOYSA-N 0.000 description 1
- YKSGJSKYCBPXDT-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-methoxyphenyl]propan-2-yl]-2-methoxyphenoxy]phenyl]pyrrole-2,5-dione Chemical compound COC1=CC(C(C)(C)C=2C=C(OC)C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O YKSGJSKYCBPXDT-UHFFFAOYSA-N 0.000 description 1
- SLHJINOEGOLHQE-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-methylphenyl]propan-2-yl]-2-methylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound CC1=CC(C(C)(C)C=2C=C(C)C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O SLHJINOEGOLHQE-UHFFFAOYSA-N 0.000 description 1
- OVBYYBVBCLQSQZ-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-propan-2-ylphenyl]propan-2-yl]-2-propan-2-ylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound CC(C)C1=CC(C(C)(C)C=2C=C(C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)C(C)C)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O OVBYYBVBCLQSQZ-UHFFFAOYSA-N 0.000 description 1
- IAKITQMGMOKJGX-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-propylphenyl]propan-2-yl]-2-propylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound CCCC1=CC(C(C)(C)C=2C=C(CCC)C(OC=3C=CC(=CC=3)N3C(C=CC3=O)=O)=CC=2)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O IAKITQMGMOKJGX-UHFFFAOYSA-N 0.000 description 1
- PYTZZNUKESXWLN-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]-1,1,1,3,3,3-hexafluoropropan-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(F)(F)F)(C(F)(F)F)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O PYTZZNUKESXWLN-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
- BWBAEDNJLKKODI-UHFFFAOYSA-N 1-[4-[4-[3-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]pentan-3-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(CC)(CC)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O BWBAEDNJLKKODI-UHFFFAOYSA-N 0.000 description 1
- LQWLNDOQUYXJKL-UHFFFAOYSA-N 1-[4-[4-[[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]-3-methylphenyl]methyl]-2-methylphenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C(C)=CC=1CC(C=C1C)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O LQWLNDOQUYXJKL-UHFFFAOYSA-N 0.000 description 1
- OBPBQKFGLIVSKR-UHFFFAOYSA-N 1-[4-[4-[[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]methyl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1OC(C=C1)=CC=C1CC(C=C1)=CC=C1OC1=CC=C(N2C(C=CC2=O)=O)C=C1 OBPBQKFGLIVSKR-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- KBLZUSCEBGBILB-UHFFFAOYSA-N 2,2-dimethylthiolane 1,1-dioxide Chemical compound CC1(C)CCCS1(=O)=O KBLZUSCEBGBILB-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
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- 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
- DZLUPKIRNOCKJB-UHFFFAOYSA-N 2-methoxy-n,n-dimethylacetamide Chemical compound COCC(=O)N(C)C DZLUPKIRNOCKJB-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
- 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
- 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
- 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
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- YQLVIOYSGHEJDA-UHFFFAOYSA-N 3-methyloxane-2,6-dione Chemical compound CC1CCC(=O)OC1=O YQLVIOYSGHEJDA-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- QLZINFDMOXMCCJ-UHFFFAOYSA-N 7-(7-hydroxyheptylperoxy)heptan-1-ol Chemical compound OCCCCCCCOOCCCCCCCO QLZINFDMOXMCCJ-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
- 239000005995 Aluminium silicate Substances 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
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 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
- 125000002947 alkylene group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910000085 borane Inorganic materials 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 239000004927 clay Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 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
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 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
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-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
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 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
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 229910052623 talc Inorganic materials 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
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- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明は、加熱することにより架橋して、耐熱
性のすぐれた硬化物を提供可能な樹脂組成物に関
する。
近年、電気機器あるいは、電子機器の大容量
化、小型軽量化あるいは高信頼度化、高密度化に
伴ない、それらに用いられる材料には、耐熱性に
すぐれ、しかも速硬化が可能な有機材料が要求さ
れている。
従来、耐熱性のすぐれた樹脂としては、ポリイ
ミド、ポリベンズイミダゾール、シリコーンなど
があるが、ポリイミド、ポリベンズイミダゾール
については硬化時の揮発性成分が多いこと、速硬
化性の付与がむずかしいこと、シリコーンについ
ては硬化物の透湿性、機械強度などに問題があつ
た。
一方、ポリスルホン、ポリカーボネートなどの
熱可塑系の耐熱材料については、成形加工性はす
ぐれているが、耐熱性の点で更に改善が要求され
ている。
本研究は、このような状況に鑑みてなされたも
ので、その要旨は、
一般式〔〕
〔式中、R1〜R4は水素、低級アルキル基、低級
アルコキシ基、塩素または臭素を示し、互いに同
じであつても異なつていてもよい。R5及びR6は
水素、メチル基、エチル基、トルフルオルメチル
基またはトリクロロメチル基であり、互いに同じ
であつても異なつていてもよい。Ｄは２ないし24
個の炭素原子をもつ２価の有機基〕で表わされる
エーテルイミド系化合物と、１ケ以上のイミド基
を含むポリアリルエステル化合物を必須成分とす
ることを特徴とする耐熱性のすぐれた樹脂組成物
である。
本発明の一般式〔〕で表わされるエーテルイ
ミド系化合物としては、例えば２，２−ビス〔４
−（４−マレイミドフエノキシ）フエニル〕プロ
パン、２，２−ビス〔３−メチル−４−（４−マ
レイミドフエノキシ）フエニル〕プロパン、２，
２−ビス〔３−クロロ−４−（４−マレイミドフ
エノキシ）フエニル〕プロパン、２，２−ビス
〔３−ブロモ−４−（４−マレイミドフエノキシ）
フエニル〕プロパン、２，２−ビス〔３−エチル
−４−（４−マレイミドフエノキシ）フエニル〕
プロパン、２，２−ビス〔３−プロピル−４−
（４−マレイミドフエノキシ）フエニル〕プロパ
ン、２，２−ビス〔３−イソプロピル−４−（４
−マレイミドフエノキシ）フエニル〕プロパン、
２，２−ビス〔３−ブチル−４−（４−マレイミ
ドフエノキシ）フエニル〕プロパン、２，２−ビ
ス〔３−sec−ブチル−４−（４−マレイミドフエ
ノキシ）フエニル〕プロパン、２，２−ビス〔３
−メトキシ−４−（４−マレイミドフエノキシ）
フエニル〕プロパン、１，１−ビス〔４−（４−
マレイミドフエノキシ）フエニル〕エタン、１，
１−ビス〔３−メチル−４−（４−マレイミドフ
エノキシ）フエニル〕エタン、１，１−ビス〔３
−クロロ−４−（４−マレイミドフエノキシ）フ
エニル〕エタン、１，１−ビス〔３−ブロモ−４
−（４−マレイミドフエノキシ）フエニル〕エタ
ン、ビス〔４−（４−マレイミドフエノキシ）フ
エニル〕メタン、ビス〔３−メチル−４−（４−
マレイミドフエノキシ）フエニル〕メタン、ビス
〔３−クロロ−４−（４−マレイミドフエノキシ）
フエニル〕メタン、ビス〔３−ブロモ−４−（４
−マレイミドフエノキシ）フエニル〕メタン、
１，１，１，３，３，３−ヘキサフルオロ−２，
２−ビス〔４−（４−マレイミドフエノキシ）フ
エニル〕プロパン、１，１，１，３，３，３−ヘ
キサクロロ−２，２−ビス〔４−（４−マレイミ
ドフエノキシ）フエニル〕プロパン、３，３−ビ
ス〔４−（４−マレイミドフエノキシ）フエニル〕
ペンタン、１，１−ビス〔４−（４−マレイミド
フエノキシ）フエニル〕プロパン、１，１，１，
３，３，３−ヘキサフルオロ−２，２−ビス
〔３，５−ジブロモ−４（４−マレイミドフエノキ
シ）フエニル〕プロパン、１，１，１，３，３，
３−ヘキサフルオロ−２，２−ビス〔３−メチル
−４（４−マレイミドフエノキシ）フエニル〕プ
ロパンなどがあり、これらの１種以上を併用して
用いることも出来る。
また、本発明において、１ケ以上のイミド基を
含むポリアリルエステル化合物としては
〔式中、Ｘは−Ｏ−、−CH2、−Ｓ−、−SO2−、
なしのいずれか〕
などがある。
本発明において、一般式〔〕で表わされるエ
ーテルイミド系化合物と、１ケ以上のイミド結合
を有するポリアリルエステル化合物との配合割合
については、一般的には、前者100重量部に対し
て、後者を10〜1000重量部の範囲で用いれば、本
発明の目的とする耐熱性、可撓性の付与された硬
化物を得ることができる。
また、本発明の樹脂組成物の硬化方法について
は、特に限定するものではないが、100〜200℃、
１〜30分間と云う短時間加熱することにより、耐
熱性のすぐれた硬化物を得ることが出来る。ま
た、本発明の樹脂組成物は、ビニル、アリルおよ
びアクリル型でありうる少なくとも１種の重合可
能なCH2＝Ｃ基を含有する単量体を添加すること
により変性できる。ここで、単量体としては、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、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、メタアクリル酸エステル、トリアリルシアヌ
レート、トリアリルシアヌレートプレポリマ、ト
リブロモフエノールアリルエーテルなどがあり、
これらの１種または２種以上を併用して使用でき
る。
また、本発明の樹脂組成物には公知の不飽和ポ
リエステルを加えることにより、硬化前に変性可
能である。ここで、不飽和ポリエステルとは、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、イタコ
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そ
の無水物、テトラヒドロフタル酸、無水カービツ
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、ジブロムネオペンチルグリコール、
ビ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、アリルグリシジル
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れない範囲で、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、ジプロムスチレン、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。
本発明の樹脂組成物には、短時間の加熱によつ
てその硬化を完了させる目的で、重合開始剤を添
加することが望ましい。そのような重合開始剤と
しては、ベンゾイルパーオキシド、Ｐ−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、カプ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−ヒドロキシミ
クロヘキシルパーオキシド）、ヒドロキシヘプチ
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、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
ーオキシイソブチレート、ジ−ｔ−ブチルパーフ
タレートなどの有機過酸化物が有用であり、その
１種または２種以上を用いることができる。
本発明においては、上述の重合解媒に、例えば
メルカプタン類、サルフアイト類、β−ジケトン
類、金属キレート類、金属石酸など公知の促進剤
を併用することも可能である。また樹旨組成物の
室温における貯蔵安定性良好にするために、例え
ばＰ−ベンゾキノン、ナフトキノン、フエナント
ラ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
ハイドロキノンなどのフエノール類や、ニトロ化
合物、金属塩類など公知の重合防止剤を、用途に
応じて使用できる。
さらに、本発明の樹脂組成物には、その用途に
応じて、種々の素材が配合される。
すなわち、例えば成形材料としての用途には、
ジルコン、シリカ、アルミナ、水酸化アルミニウ
ム、ナタニア、亜鉛華、炭酸カルシウム、マグネ
ナイト、クレー、カオリン、タルク、珪砂、カラ
ス、溶融石英ガラス、アスベスト、マイカ、各種
ウイスカー、カーホンフラツク、黒鉛、二硫化モ
リブデンなどのような無機質充填剤、高級脂肪酸
やワツクスなどのような離型剤、エポキシシラ
ン、ビニルシラン、ボランやアルコキシチタネー
ト系化合物などのようなカツプリンク剤が配合さ
れる。また必要に従つて、含ハロゲン化合物、酸
化アンチモンやリン化合物などの難燃性付与剤な
どを用いることができる。
またワニスなどのように、溶液として使用する
こともできる。その際用いられる溶剤としては、
Ｎ−メチル−２−ピロリドン、Ｎ，Ｎ−ジメチル
アセトアミド、Ｎ，Ｎ−ジメチルホルムアミド、
Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルホル
ムアミド、ジメチルスルホオキシド、Ｎ，Ｎ−ジ
エチルアセトアミド、Ｎ，Ｎ−ジメチルメトキシ
アセトアミド、ヘキサメチルフオスホルアミド、
ピリシン、ジメチルスルホン、テトラメチルスル
ホン、ジメチルテトラメチレンスルホン等があ
り、また、フエノール系溶剤群としては、フエノ
ール、クレゾール、キシレノールなどがある。
以上のものについては単独または２種以上の混
合して使用される。
次に実施例によつて本発明を具体的に説明す
る。
実施例 １〜９
アリルエステル化合物としては、次の４種類の
化合物を用いた。
上述の４種類の化合物と、Ｎ，Ｎ−置換ビスマ
レイミド化合物、トリアリルイソシアヌレートを
表１に示す所定割合に配合した。
上記９種類の配合物を、50〜70℃の２本ロール
で10分間混練した後、粕粉砕して、目的の組成物
を得た。
次いで、上記組成物を180℃、70Kg／cm2、２分
間の条件で、各種特性測定用の試験片をトランス
フアモールドした。
第１表に、曲げ強さと加熱劣化特性を示した。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a resin composition that can be crosslinked by heating to provide a cured product with excellent heat resistance. In recent years, as electric and electronic devices have become larger in capacity, smaller and lighter, more reliable, and more dense, organic materials that have excellent heat resistance and can harden quickly are being used as materials for these devices. is required. Conventionally, resins with excellent heat resistance include polyimide, polybenzimidazole, and silicone, but polyimide and polybenzimidazole contain many volatile components during curing, and it is difficult to impart fast curing properties. However, there were problems with the moisture permeability and mechanical strength of the cured product. On the other hand, thermoplastic heat-resistant materials such as polysulfone and polycarbonate have excellent moldability, but further improvement is required in terms of heat resistance. This research was carried out in view of this situation, and its gist is that the general formula [] [In the formula, R 1 to R 4 represent hydrogen, a lower alkyl group, a lower alkoxy group, chlorine or bromine, and may be the same or different from each other. R 5 and R 6 are hydrogen, a methyl group, an ethyl group, a trifluoromethyl group, or a trichloromethyl group, and may be the same or different. D is 2 to 24
A resin composition with excellent heat resistance characterized by containing as essential components an etherimide compound represented by a divalent organic group having 1 carbon atom and a polyallyl ester compound containing one or more imide groups. It is a thing. Examples of the etherimide compound represented by the general formula [] of the present invention include 2,2-bis[4
-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[3-methyl-4-(4-maleimidophenoxy)phenyl]propane, 2,
2-bis[3-chloro-4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[3-bromo-4-(4-maleimidophenoxy)
phenyl]propane, 2,2-bis[3-ethyl-4-(4-maleimidophenoxy)phenyl]
Propane, 2,2-bis[3-propyl-4-
(4-maleimidophenoxy)phenyl]propane, 2,2-bis[3-isopropyl-4-(4
-maleimidophenoxy)phenyl]propane,
2,2-bis[3-butyl-4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[3-sec-butyl-4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[3
-methoxy-4-(4-maleimidophenoxy)
phenyl]propane, 1,1-bis[4-(4-
maleimidophenoxy)phenyl]ethane, 1,
1-bis[3-methyl-4-(4-maleimidophenoxy)phenyl]ethane, 1,1-bis[3
-chloro-4-(4-maleimidophenoxy)phenyl]ethane, 1,1-bis[3-bromo-4
-(4-maleimidophenoxy)phenyl]ethane, bis[4-(4-maleimidophenoxy)phenyl]methane, bis[3-methyl-4-(4-
maleimidophenoxy) phenyl]methane, bis[3-chloro-4-(4-maleimidophenoxy)
phenyl]methane, bis[3-bromo-4-(4
-maleimidophenoxy)phenyl]methane,
1,1,1,3,3,3-hexafluoro-2,
2-bis[4-(4-maleimidophenoxy)phenyl]propane, 1,1,1,3,3,3-hexachloro-2,2-bis[4-(4-maleimidophenoxy)phenyl] Propane, 3,3-bis[4-(4-maleimidophenoxy)phenyl]
Pentane, 1,1-bis[4-(4-maleimidophenoxy)phenyl]propane, 1,1,1,
3,3,3-hexafluoro-2,2-bis[3,5-dibromo-4(4-maleimidophenoxy)phenyl]propane, 1,1,1,3,3,
Examples include 3-hexafluoro-2,2-bis[3-methyl-4(4-maleimidophenoxy)phenyl]propane, and one or more of these can also be used in combination. In addition, in the present invention, as a polyallyl ester compound containing one or more imide groups, [Wherein, X is -O-, -CH2 , -S-, -SO2- ,
None] and so on. In the present invention, the blending ratio of the etherimide compound represented by the general formula [] and the polyallyl ester compound having one or more imide bonds is generally 100 parts by weight of the former to 100 parts by weight of the latter. When used in an amount of 10 to 1000 parts by weight, it is possible to obtain a cured product that has the heat resistance and flexibility that are the object of the present invention. Furthermore, the method for curing the resin composition of the present invention is not particularly limited;
By heating for a short time of 1 to 30 minutes, a cured product with excellent heat resistance can be obtained. The resin compositions of the invention can also be modified by adding monomers containing at least one polymerizable CH 2 =C group, which can be of the vinyl, allyl and acrylic type. Here, examples of the monomer include styrene, vinyltoluene, α-methylstyrene, divinylbenzene, diallylphthalate,
Diallyl phthalate prepolymer, chlorstyrene, dichlorostyrene, bromstyrene, dibromstyrene, diallylbenzene phosphonate, diallylaryl phosphinate, acrylic acid, methacrylic acid ester, triallyl cyanurate, triallyl cyanurate prepolymer, Tribromophenol allyl ether, etc.
These can be used alone or in combination of two or more. Further, the resin composition of the present invention can be modified before curing by adding a known unsaturated polyester. Here, unsaturated polyester is composed 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. Polyester resin matrix containing unsaturated groups synthesized by condensation or addition polymerization using reactions such as esterification and transesterification, and the polymerizability of ethylene-based (e.g. vinyl groups, allyl groups, etc.) 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, itaconic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, methylglutaric anhydride , pimelic acid, hexahydrophthalic acid and its anhydride, tetrahydrophthalic acid, carbicic anhydride, Hett's acid and its anhydride, tetrachlorophthalic acid and its anhydride, tetrabromophthalic acid and its anhydride, lower alkyl thereof Ester etc. are used, and diol components include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol,
Propylene glycol, dipropylene glycol, trimethylene glycol, tetramethylene glycol, hexamethylene glycol, 2,2-
Diethylpropanediol 1,3, neopentyl glycol, dibromneopentyl glycol,
Bisphenol 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 glycidyl ether, etc. are used. Furthermore, 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 the crosslinking agent include styrene, vinyltoluene, α-methylstyrene, divinylbenzene, diallyl phthalate, diallyl phthalate prepolymer, chlorstyrene, dichlorostyrene, bromustyrene, dipromstyrene, diallylbenzenephosphonate, and diallyl phosphinate. , 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 is not limited to one type, and a mixture of two or more types is also possible. It is desirable to add a polymerization initiator to the resin composition of the present invention in order to complete its curing by short-term heating. Such polymerization initiators include benzoyl peroxide, P-chloro-
Benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, caprylyl peroxide,
Lauroyl peroxide, acetyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, bis(1-hydroxymicrohexyl peroxide), hydroxyheptyl peroxide, t-butyl hydroperoxide, P-menthane hydroperoxide, t-butyl peroxide Organic peroxides such as benzoate, t-butyl peracetate, t-butyl peroctoate, t-butyl peroxyisobutyrate, and di-t-butyl perphthalate are useful, and one or more of them may be used. Can be used. In the present invention, it is also possible to use a known accelerator such as mercaptans, sulfites, .beta.-diketones, metal chelates, and metal mineral acids in combination with the above-mentioned polymerization decomposition medium. In addition, in order to improve the storage stability of the tree composition at room temperature, for example, quinones such as P-benzoquinone, naphthoquinone, and phenanthraquinone, hydroquinone, P-
Known polymerization inhibitors such as phenols such as t-butylcatechol and 2,5-di-t-butylhydroquinone, nitro compounds, and metal salts can be used depending on the purpose. Furthermore, various materials may be blended into the resin composition of the present invention depending on its use. That is, for example, for use as a molding material,
Zircon, silica, alumina, aluminum hydroxide, natania, zinc white, calcium carbonate, magneite, clay, kaolin, talc, silica sand, crow, fused silica glass, asbestos, mica, various whiskers, carphone flak, graphite, molybdenum disulfide, etc. Inorganic fillers such as, mold release agents such as higher fatty acids and waxes, and coupling agents such as epoxy silane, vinyl silane, borane and alkoxy titanate compounds are blended. Further, flame retardant imparting agents such as halogen-containing compounds, antimony oxide, and phosphorus compounds can be used as necessary. It can also be used as a solution, such as a varnish. The solvent used in this case is
N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide,
N,N-dimethylformamide, N-methylformamide, dimethylsulfoxide, N,N-diethylacetamide, N,N-dimethylmethoxyacetamide, hexamethylphosphoramide,
Examples include pyricine, dimethylsulfone, tetramethylsulfone, dimethyltetramethylenesulfone, and the phenolic solvent group includes phenol, cresol, xylenol, and the like. The above materials may be used alone or in combination of two or more. Next, the present invention will be specifically explained with reference to Examples. Examples 1 to 9 The following four types of compounds were used as allyl ester compounds. The above-mentioned four types of compounds, an N,N-substituted bismaleimide compound, and triallyl isocyanurate were blended in the predetermined ratios shown in Table 1. The above-mentioned nine types of blends were kneaded with two rolls at 50 to 70°C for 10 minutes, and then ground into lees to obtain the desired composition. Next, the above composition was transform-molded into test pieces for measuring various properties under the conditions of 180° C., 70 kg/cm 2 and 2 minutes. Table 1 shows the bending strength and heat deterioration characteristics. 【table】
Claims (1)
アルコキシ基、塩素または臭素を示し、互いに同
じであつても異なつていてもよい。R5及びR6は
水素、メチル基、エチル基、トルフルオルメチル
基またはトリクロロメチル基であり、互いに同じ
であつても異なつていてもよい。Ｄは２ないし24
個の炭素原子をもつ２価の有機基〕で表わされる
エーテルイミド系化合物と、１ケ以上のイミド基
を含む、ポリアリルエステル化合物を必須成分と
することを特徴とする耐熱性のすぐれた耐熱性樹
脂組成物。[Claims] 1. General formula [] [In the formula, R 1 to R 4 represent hydrogen, a lower alkyl group, a lower alkoxy group, chlorine or bromine, and may be the same or different from each other. R 5 and R 6 are hydrogen, a methyl group, an ethyl group, a trifluoromethyl group, or a trichloromethyl group, and may be the same or different. D is 2 to 24
Excellent heat resistance characterized by having as essential components an etherimide compound represented by a divalent organic group having 1 or more carbon atoms and a polyallyl ester compound containing one or more imide groups. resin composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5709181A JPS57172908A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5709181A JPS57172908A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57172908A JPS57172908A (en) | 1982-10-25 |
| JPH0135846B2 true JPH0135846B2 (en) | 1989-07-27 |
Family
ID=13045825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5709181A Granted JPS57172908A (en) | 1981-04-17 | 1981-04-17 | Heat-resistant resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57172908A (en) |
-
1981
- 1981-04-17 JP JP5709181A patent/JPS57172908A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57172908A (en) | 1982-10-25 |
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