JPS6330927B2 - - Google Patents
Info
- Publication number
- JPS6330927B2 JPS6330927B2 JP56189166A JP18916681A JPS6330927B2 JP S6330927 B2 JPS6330927 B2 JP S6330927B2 JP 56189166 A JP56189166 A JP 56189166A JP 18916681 A JP18916681 A JP 18916681A JP S6330927 B2 JPS6330927 B2 JP S6330927B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- polyether
- block copolymer
- compound
- 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 glycidyl ester compound Chemical class 0.000 claims description 37
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 32
- 229920000570 polyether Polymers 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- 229920001400 block copolymer Polymers 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 230000006866 deterioration Effects 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- UYLNEXRLQPVSOZ-UHFFFAOYSA-N 1-[3-(hydroxymethyl)-2,2,5,5-tetramethylpyrrol-1-yl]ethanone Chemical compound CC(=O)N1C(C)(C)C=C(CO)C1(C)C UYLNEXRLQPVSOZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 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
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- KTEARTXATWOYDB-UHFFFAOYSA-N 1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)C1=CC=C(Cl)C=C1 KTEARTXATWOYDB-UHFFFAOYSA-N 0.000 description 1
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- BTBJCTWMARHHQD-UHFFFAOYSA-N 2-heptadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O BTBJCTWMARHHQD-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VWYIWOYBERNXLX-KTKRTIGZSA-N Glycidyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CO1 VWYIWOYBERNXLX-KTKRTIGZSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VKEFGOTVPWVWCH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-methylbenzene-1,4-dicarboxylate Chemical compound CC1=CC(C(=O)OCC2OC2)=CC=C1C(=O)OCC1CO1 VKEFGOTVPWVWCH-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- JQDCYGOHLMJDNA-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) butanedioate Chemical compound C1OC1COC(=O)CCC(=O)OCC1CO1 JQDCYGOHLMJDNA-UHFFFAOYSA-N 0.000 description 1
- KTPIWUHKYIJBCR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C1C=CCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KTPIWUHKYIJBCR-UHFFFAOYSA-N 0.000 description 1
- UTDPRMMIFFJALK-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,1-dicarboxylate Chemical compound C1CCCCC1(C(=O)OCC1OC1)C(=O)OCC1CO1 UTDPRMMIFFJALK-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- NFVGWOSADNLNHZ-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) decanedioate Chemical compound C1OC1COC(=O)CCCCCCCCC(=O)OCC1CO1 NFVGWOSADNLNHZ-UHFFFAOYSA-N 0.000 description 1
- QGTGWZMXYMSFJE-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) dodecanedioate Chemical compound C1OC1COC(=O)CCCCCCCCCCC(=O)OCC1CO1 QGTGWZMXYMSFJE-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- AUNDMQBAPCPNJA-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) naphthalene-1,2-dicarboxylate Chemical compound C=1C=C2C=CC=CC2=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 AUNDMQBAPCPNJA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000000903 blocking effect Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003086 colorant Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- LOGTZDQTPQYKEN-HZJYTTRNSA-N oxiran-2-ylmethyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1CO1 LOGTZDQTPQYKEN-HZJYTTRNSA-N 0.000 description 1
- SJVUKRJWTDCMSJ-UHFFFAOYSA-N oxiran-2-ylmethyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCC1OC1 SJVUKRJWTDCMSJ-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- BEJZOPYRAQVYHS-UHFFFAOYSA-N oxiran-2-ylmethyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OCC1CO1 BEJZOPYRAQVYHS-UHFFFAOYSA-N 0.000 description 1
- PGXFPHPLDLNGQY-UHFFFAOYSA-N oxiran-2-ylmethyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC1CO1 PGXFPHPLDLNGQY-UHFFFAOYSA-N 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- KYVUJPJYTYQNGJ-UHFFFAOYSA-N oxiran-2-ylmethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1CO1 KYVUJPJYTYQNGJ-UHFFFAOYSA-N 0.000 description 1
- DJTYNOVDSWHTJM-UHFFFAOYSA-N oxiran-2-ylmethyl nonanoate Chemical compound CCCCCCCCC(=O)OCC1CO1 DJTYNOVDSWHTJM-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- MRQLRZQLPODMPG-UHFFFAOYSA-N tris(phenylsulfanyl)phosphane Chemical compound C=1C=CC=CC=1SP(SC=1C=CC=CC=1)SC1=CC=CC=C1 MRQLRZQLPODMPG-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
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The present invention relates to a polyetherester block copolymer composition having excellent heat deterioration resistance and hydrolysis resistance. Polyether ester block copolymers having alternating polyether and polyester parts in their molecular chains are known as polymers with rubber-like elasticity and are useful as fibers, films, and molded products. However, since polyether ester block copolymers contain unstable polyether blocks in their main chains, they are susceptible to oxidative deterioration, and as the degree of polymerization decreases, mechanical properties decrease, surface cracks occur, coloring and severe When this happens, undesirable phenomena such as decomposition and volatilization of polyether occur. In particular, this oxidative deterioration is accelerated by heat, and its use is restricted in high-temperature atmospheres. In order to improve these properties, the addition of antioxidants such as hindered phenols, aromatic amines, sulfur compounds, and phosphorus compounds has been considered to prevent thermal deterioration. However, there is a problem with coloring of the polymer due to antioxidants, and the effect of improving heat resistance is insufficient. In addition, since polyether ester block copolymers have ester groups in their molecular chains, they are susceptible to hydrolysis, and when placed in water, alcohol, acidic or alkaline solutions, their physical properties decrease as the degree of polymerization decreases. Therefore, there are restrictions on its use in this respect as well. In order to improve these properties, a method has also been proposed in which a compound having a reactive polyfunctional group is added to the polyether ester block copolymer to block the terminal groups of the copolymer. For example, JP-A-49-
Publication No. 13298 describes a method for improving abrasion resistance, hydrolytic stability, and high-temperature properties by adding a difunctional or higher-functionality polyepoxide and a curing agent to a polyether ester block copolymer. Polyglycidyl ether compounds derived from epichlorohydrin and phenols or epichlorohydrin and alcohols are described in the Examples. It is true that abrasion resistance etc. can be improved by blocking the terminals of a polyether ester block copolymer with a polyglycidyl ether compound, but the polyglycidyl ether compound itself has poor reactivity, so it is difficult to use curing agents such as polyamines. I need. It was also found that sufficient improvement effects could not be obtained simply by blending the curing agent into the polyether ester block copolymer without using a curing agent. Therefore, the present inventors have developed a compound that is highly reactive to polyether ester block copolymers and that can reliably improve the heat deterioration resistance or hydrolysis resistance of polyether ester block copolymers simply by blending them. As a result of intensive studies, we have arrived at the following invention. That is, the present invention provides a polyether ester block copolymer composition characterized in that 0.01 to 20% by weight of a glycidyl ester compound represented by the following general formula is blended with the polyether ester block copolymer. It is something. (In the formula, R is an n-valent organic carboxylic acid residue having 1 to 30 carbon atoms, and n is an integer of 1 to 4.) The polyether ester block copolymer in the present invention refers to a polyester hard segment. It is a copolymer consisting of polyether soft segments with a number average molecular weight of approximately 200 to 6000, and the ratio of hard segments to soft segments is 15 to 90% by weight.
85 to 10% by weight. Dicarboxylic acid components forming polyester hard segments include terephthalic acid, isophthalic acid, phthalic acid,
Aromatic dicarboxylic acids such as 2,6- and 1,5-naphthalene dicarboxylic acid, bis(p-carboxyphenyl)methane, anthracene dicarboxylic acid, 4,4â²-diphenyl ether dicarboxylic acid,
Examples include alicyclic dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid, cyclopentanedicarboxylic acid, and 4,4'-dicyclohexyldicarboxylic acid, and aliphatic dicarboxylic acids such as adipic acid, sebacic acid, azelaic acid, and dimic acid. but,
From the viewpoint of mechanical properties and heat resistance, it is preferable to use aromatic dicarboxylic acid in an amount of at least 50 mol %, and use of terephthalic acid is particularly recommended. In addition, the diol components constituting the hard segment include aliphatic or alicyclic diols having 2 to 12 carbon atoms, such as ethylene glycol, propylene glycol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol,
1,6-hexanediol, decamethylene glycol, cyclohexanedimethanol, bis(p
Bisphenols such as -hydroxy)diphenyl, bis(p-hydroxyphenyl)methane, bis(p-hydroxyphenyl)propane and mixtures thereof may be used, but especially aliphatic or alicyclic groups having 2 to 8 carbon atoms. Diols are preferably used. In addition, the poly(alkylene oxide) glycols constituting the polyether soft segment are polyethylene glycol, poly(1,3- and 1,
2-propylene glycol, poly(tetramethylene oxide) glycol, polyethylene glycol polypropylene glycol block copolymer,
These include polyethylene glycol-poly(tetramethylene oxide) glycol block copolymers, and poly(tetramethylene oxide) glycol is particularly preferred, although it is of course possible to use these in combination. The average molecular weight of these polyether glycols ranges from about 200 to 6000. The polyether ester block copolymer made of these components can be produced by any method, but one example of a suitable polymerization method is to add dimethyl ester of dicarboxylic acid to an excess of about 1.2 to 2.0 moles relative to the acid.
A heating reaction is carried out with twice the molar amount of low molecular weight glycol and poly(alkylene oxide) glycol at a temperature of about 150 to 260°C under normal pressure in the presence of a normal esterification catalyst to perform transesterification and distill off methanol. It can be produced by heating polycondensation at 200 to 270°C under reduced pressure of 5 mmHg or less. If necessary, a polyfunctional copolymer component that can be partially chemically crosslinked, such as polycarboxylic acid, polyol, polyoxycarboxylic acid, etc., may be used in the polyether ester block copolymer. The glycidyl ether compound blended into the polyether ester block copolymer in the composition of the present invention is represented by the following general formula. (In the formula, R is an n-valent organic carboxylic acid residue having 1 to 30 carbon atoms, and n is an integer of 1 to 4.) Here, R is an n-valent organic carboxylic acid residue having 1 to 30 carbon atoms. It is a residue, and includes aliphatic groups with 30 or less carbon atoms, alicyclic groups such as cyclohexylene, phenylene, naphthylene,
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ã«ãªãæéãšãããIt contains an aromatic group such as [Formula]. n is 1~
It is an integer of 4. Here, specific examples of the glycidyl ester compounds include glycidyl benzoate, p-toluic acid glycidyl ester, cyclohexanecarboxylic acid glycidyl ester, pelargonic acid glycidyl ester, stearic acid glycidyl ester, lauric acid glycidyl ester, palmitic acid glycidyl ester, Behenic acid glycidyl ester, versatile acid glycidyl ester, oleic acid glycidyl ester, linoleic acid glycidyl ester, linolenic acid glycidyl ester,
Behenolic acid glycidyl ester, stearic acid glycidyl ester, terephthalic acid diglycidyl ester, isophthalic acid diglycidyl ester, phthalic acid diglycidyl ester, naphthalene dicarboxylic acid diglycidyl ester, bibenzoic acid diglycidyl ester, methyl terephthalic acid diglycidyl ester, Hexahydrophthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, cyclohexanedicarboxylic acid diglycidyl ester, adipic acid diglycidyl ester, succinic acid diglycidyl ester, sebacic acid diglycidyl ester, dodecanedioic acid diglycidyl ester, octadecanedicarboxylic acid Examples include diglycidyl ester, trimellitic acid triglycidyl ester, pyromellitic acid tetraglycidyl ester, etc., and these may be used singly or in combination.
More than one species can be used. The amount of glycidyl ester compound added is 0.01 to the polyether ester block copolymer.
A range of ~20% by weight, preferably 0.05 to 10% by weight is appropriate, and if it is less than 0.01% by weight, a sufficient effect of improving heat deterioration resistance and hydrolysis resistance cannot be obtained.
Moreover, if the content is 20% by weight, gelation of the polymer tends to occur during compounding or molding, which is not preferable. The method for adding a glycidyl ester compound to a polyether ester block copolymer is as follows:
Examples include a method of melt-mixing immediately after polymerization, or a method of melt-mixing after polymerization (before molding).
The latter is particularly preferred. The heat deterioration resistance of the composition of the present invention is further improved by adding heat-resistant stability. Examples of these stabilizers include 4,4'-bis(2,6-di-tertiary
butylphenol), 1,3,5-trimethyl-
2,4,6-tris(3,5-di-tert-butyl-4
-hydroxybenzyl)benzene, tetrakis[methylene-3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane, hexamethylene glycol bis[β-(3,5-di-tert-butyl-4-) hydroxyphenyl)propionate], 6-(4-hydroxy-3,5-di-tertiary)
butylanilino)-2,4-bisoctylthio-
1,3,5-triazine, 2,2'-thiodiethyl-bis[3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3(3,5-di-tert-butyl- 4-hydroxyphenyl) propionate, N,N'-hexamethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamide, tris(3,5-di-tert-butyl-4-hydroxyphenyl) enyl) isocyanurate, tris[β-(3,5-di-tert-butyl-
Various hindered phenols such as 4-hydroxyphenyl) propionyl-oxyethylene] isocyanurate, N,N'-bis(β-naphthyl)
-p-phenylenediamine and 4,4'-bis(4-
Aromatic amines such as α,α-dimethylbenzyl)diphenylamine, thioether compounds such as dilaurylthiodipropionate and distearylthiodipropionate, triphenylphosphite, trinonylphosphite, and tricresylphosphite. Examples include phosphite compounds, thiophosphite compounds such as trinonyltrithiophosphite, trilauryltrithiophosphite, and triphenyltrithiophosphite. In particular, when one or both of a thioether compound or a thiophosphite compound is added to hindered phenols, excellent heat deterioration resistance without coloring can be obtained. In addition, the polyether ester block copolymer composition of the present invention may contain light stabilizers such as substituted benzophenones, benzotriazoles, and piperidine compounds, colorants (application materials, dyes), antistatic agents, conductive agents, crystal nuclei, etc. Additives such as agents, lubricants, fillers, reinforcing agents, adhesion aids, plasticizers, mold release agents, and flame retardants may be optionally blended. The present invention will be explained below with reference to Examples. In the examples, all "parts" or "%" are expressed as weight ratios. Further, the logarithmic viscosity shown in the text and examples is a value measured in orthochlorophenol at 30°C and at a concentration of 0.5%. Example Polymer A 90.8 parts of dimethyl terephthalate, 30.3 parts of dimethyl isophthalate, 69.0 parts of poly(tetramethylene oxide) glycol having a number average molecular weight of 1000, and 84.2 parts of 1,4-butanediol were stirred in a helical ribbon type with 0.10 part of titanium tetrabutoxide catalyst. The mixture was charged into a reaction vessel equipped with blades and heated at 210°C for 2 hours to distill off 95% of the theoretical amount of methanol from the system. Next, the temperature was raised to 245°C, and the pressure inside the system was reduced to 0.2 mmHg over 50 minutes, and polymerization was carried out under these conditions for 2 hours. The resulting polyether ester (A) has a melting point of 162â and a logarithmic viscosity.
It was 0.98. Polymer B: 194 parts of dimethyl terephthalate, number average molecular weight
Polyether ester (B ) was obtained. Polymer C: 48.4 parts of dimethyl terephthalate, number average molecular weight
2000 poly(tetramethylene oxide) glycol 110 parts, ethylene glycol 44.0 parts, zinc acetate
From 0.080 parts and germanium dioxide 0.048 parts,
Polymerized under the same conditions as Polymer A, melting point 210â,
A polyether ester (C) with a logarithmic viscosity of 1.3 was obtained. Examples 1 to 5 and Comparative Examples 1 to 5 1.0% or 2.0% of the glycidyl ether compounds listed in Table 1 or a comparative glycidyl ether compound or polycarbodiimide compound was blended with polyether ester (A), and the mixture was heated to 240°C. The mixture was melt-kneaded in a heated 30 mmÏ extruder and then pelletized. After vacuum drying the pellets,
It was pressurized at 240°C to form a press sheet with a thickness of 0.9 to 1.1 mm and punched into JIS K-6301 No. 3 dumbbell-shaped test pieces. The test piece was aged in a hot air oven at 140°C to determine its heat resistance life. The heat-resistant life was defined as the time when the retention rate of elongation at break reached 50%. In addition, the test piece was placed in a stainless steel pressure cylinder with water at 100°C.
The hydrolysis life was determined by heating. The hydrolysis life is similar to the heat life, and the elongation retention rate at break is 50.
%.
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ã調ã¹ãã[Table] As is clear from the examples and comparative examples, excellent heat deterioration resistance and hydrolysis resistance can be obtained only when a glycidyl ester compound is added, and excellent resistance to heat deterioration and hydrolysis can be obtained by adding a glycidyl ether compound or a polycarbodiimide compound. , only a slight improvement effect was observed. Examples 6 to 7, Comparative Examples 6 to 9 An injection molding machine in which the glycidyl ester compound and heat stabilizer listed in Table 2 were blended with polyether ester (B) or polyether ester (C) and heated to 240°C. A JIS K7113 No. 2 dumbbell-shaped test piece was molded from the sample. This test piece was aged in a hot air oven at 140°C, and the heat resistance life and presence or absence of yellowing were examined. In addition, as a comparison, a compound other than the glycidyl ester compound and a heat-resistant stabilizer were blended, and after molding into a test piece in the same manner as in the example, the heat deterioration resistance was examined.
ãè¡šããtableã
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æã«ãããã°ãªã·ãžã«ãšã¹ãã«ååç©ãšèç±å®å®
å€ãšãæ·»å ããå Žåã¯é»å€ã®ãªãèç±å£åæ§ãè¯
奜ãªçµæç©ãåŸãããã®ã«å¯Ÿããã°ãªã·ãžã«ãšã¹
ãã«ååç©ãæ·»å ããªãã§èç±å®å®å€ã®ã¿ãæ·»å
ããå Žåããããã¯ã°ãªã·ãžã«ãšãŒãã«ååç©ã
ããªã«ã«ããžã€ããååç©ãšèç±å®å®å€ãšãæ·»å
ããå Žåã¯é»å€ããèç±å£åæ§ãæ¬çºæçµæç©ã
ãããªãå£ã€ããã®ããåŸãããªãã[Table] As is clear from the Examples and Comparative Examples, when the glycidyl ester compound of the present invention and a heat-resistant stabilizer are added, a composition with good heat deterioration resistance without yellowing can be obtained. When only a heat stabilizer was added without adding an ester compound, or when a glycidyl ether compound or a polycarbodiimide compound and a heat stabilizer were added, yellowing occurred and the heat deterioration resistance was considerably inferior to that of the composition of the present invention. I can only get it.
Claims (1)
ããäžèšäžè¬åŒã§ç€ºãããã°ãªã·ãžã«ãšã¹ãã«å
åç©ã0.01ã20ééïŒ é åããããããšãç¹åŸŽãš
ããããªãšãŒãã«ãšã¹ãã«ãããã¯å ±éåäœçµæ
ç©ã ïŒåŒäžïŒ²ã¯ççŽ æ°ïŒã30ã®ïœäŸ¡ã®ææ©ã«ã«ãã³é ž
æ®åºã§ãããïœã¯ïŒãïŒã®æŽæ°ã§ãããïŒ[Scope of Claims] 1. A polyether ester block copolymer composition comprising 0.01 to 20% by weight of a glycidyl ester compound represented by the following general formula based on the polyether ester block copolymer. (In the formula, R is an n-valent organic carboxylic acid residue having 1 to 30 carbon atoms, and n is an integer of 1 to 4.)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18916681A JPS5891758A (en) | 1981-11-27 | 1981-11-27 | Polyether-ester block copolymer composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18916681A JPS5891758A (en) | 1981-11-27 | 1981-11-27 | Polyether-ester block copolymer composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5891758A JPS5891758A (en) | 1983-05-31 |
JPS6330927B2 true JPS6330927B2 (en) | 1988-06-21 |
Family
ID=16236565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP18916681A Granted JPS5891758A (en) | 1981-11-27 | 1981-11-27 | Polyether-ester block copolymer composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5891758A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62218437A (en) * | 1986-03-19 | 1987-09-25 | Mitsubishi Rayon Co Ltd | Polyester resin composition |
KR950008565A (en) * | 1993-09-10 | 1995-04-19 | ë°íêž° | Method for producing polyether ester elastomer |
TW585880B (en) * | 1999-08-05 | 2004-05-01 | Daicel Chem | Process for producing polyester block copolymer |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS48100495A (en) * | 1972-02-28 | 1973-12-18 | ||
JPS5384046A (en) * | 1976-12-30 | 1978-07-25 | Sumitomo Chem Co Ltd | Polyarylate composition |
JPS53104654A (en) * | 1977-02-23 | 1978-09-12 | Unitika Ltd | Aromatic polyester copolymer composition |
JPS5460350A (en) * | 1977-10-20 | 1979-05-15 | Toray Ind Inc | Thermopastic resin composition |
-
1981
- 1981-11-27 JP JP18916681A patent/JPS5891758A/en active Granted
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS48100495A (en) * | 1972-02-28 | 1973-12-18 | ||
JPS5384046A (en) * | 1976-12-30 | 1978-07-25 | Sumitomo Chem Co Ltd | Polyarylate composition |
JPS53104654A (en) * | 1977-02-23 | 1978-09-12 | Unitika Ltd | Aromatic polyester copolymer composition |
JPS5460350A (en) * | 1977-10-20 | 1979-05-15 | Toray Ind Inc | Thermopastic resin composition |
Also Published As
Publication number | Publication date |
---|---|
JPS5891758A (en) | 1983-05-31 |
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