JPS636090B2 - - Google Patents
Info
- Publication number
- JPS636090B2 JPS636090B2 JP7486180A JP7486180A JPS636090B2 JP S636090 B2 JPS636090 B2 JP S636090B2 JP 7486180 A JP7486180 A JP 7486180A JP 7486180 A JP7486180 A JP 7486180A JP S636090 B2 JPS636090 B2 JP S636090B2
- Authority
- JP
- Japan
- Prior art keywords
- aromatic polyester
- reaction
- iminoester
- group
- biscyclic
- 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
- 229920000728 polyester Polymers 0.000 claims description 193
- 125000003118 aryl group Chemical group 0.000 claims description 187
- -1 alkylene glycol Chemical compound 0.000 claims description 113
- 238000006243 chemical reaction Methods 0.000 claims description 107
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 104
- 238000006116 polymerization reaction Methods 0.000 claims description 76
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 238000000465 moulding Methods 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000000155 melt Substances 0.000 claims description 21
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 229920001281 polyalkylene Polymers 0.000 claims description 6
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 229920001169 thermoplastic Polymers 0.000 claims 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 57
- 238000000034 method Methods 0.000 description 45
- 230000000052 comparative effect Effects 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 229920000139 polyethylene terephthalate Polymers 0.000 description 19
- 239000005020 polyethylene terephthalate Substances 0.000 description 19
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 18
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 16
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 229920005992 thermoplastic resin Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 11
- 239000000806 elastomer Substances 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- BWLYWJSWRDLSGY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=COC1=O BWLYWJSWRDLSGY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HTQKMAGYKHPFQM-UHFFFAOYSA-N 4-methyl-4h-1,3-oxazol-5-one Chemical compound CC1N=COC1=O HTQKMAGYKHPFQM-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006473 carboxylation reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- DGEYLAXCRHMGLG-UHFFFAOYSA-N 4-(2-methylpropyl)-4h-1,3-oxazol-5-one Chemical compound CC(C)CC1N=COC1=O DGEYLAXCRHMGLG-UHFFFAOYSA-N 0.000 description 4
- DANDTMGGYNCQLG-UHFFFAOYSA-N 4h-1,3-oxazol-5-one Chemical compound O=C1CN=CO1 DANDTMGGYNCQLG-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 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 4
- 230000021523 carboxylation Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000003901 oxalic acid esters Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- DUILGEYLVHGSEE-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1CO1 DUILGEYLVHGSEE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920003232 aliphatic polyester Polymers 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- ZFEMNACSNMBKPE-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)phenyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1C1=CC=C(C=2OC(=O)C(C)(C)N=2)C=C1 ZFEMNACSNMBKPE-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- VNKZACZQXVQWKA-UHFFFAOYSA-N 4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound CC(C)C1N=COC1=O VNKZACZQXVQWKA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 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
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005470 impregnation 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
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 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
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003746 solid phase reaction Methods 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
- 239000008096 xylene Substances 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- QBUXRIUNFDMSAK-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-3-propylpyrrolidine-2,5-dione Chemical compound O=C1C(CCC)CC(=O)N1CC1OC1 QBUXRIUNFDMSAK-UHFFFAOYSA-N 0.000 description 1
- KTCCGEXQRZSXIJ-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1OC1 KTCCGEXQRZSXIJ-UHFFFAOYSA-N 0.000 description 1
- QVNQWADZKGITKV-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CC1OC1 QVNQWADZKGITKV-UHFFFAOYSA-N 0.000 description 1
- SNGZGCFWZHOVOS-UHFFFAOYSA-N 2-(2-methyloctoxymethyl)oxirane Chemical compound CCCCCCC(C)COCC1CO1 SNGZGCFWZHOVOS-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- GKBGCVILKYKJIA-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound O=C1C2CCCCC2C(=O)N1CC1CO1 GKBGCVILKYKJIA-UHFFFAOYSA-N 0.000 description 1
- ZAWQXYPBFKPQLD-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound O=C1C2CC=CCC2C(=O)N1CC1CO1 ZAWQXYPBFKPQLD-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- ARJYLIOEJWMXTA-UHFFFAOYSA-N 2-[(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)methyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CC1=NC(C)(C)C(=O)O1 ARJYLIOEJWMXTA-UHFFFAOYSA-N 0.000 description 1
- RFLLHIZFIWJOIH-UHFFFAOYSA-N 2-[(4-oxo-3,1-benzoxazin-2-yl)methyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 RFLLHIZFIWJOIH-UHFFFAOYSA-N 0.000 description 1
- MNKGJLCEYRTBNX-UHFFFAOYSA-N 2-[(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)methyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CC1=NC(C(C)C)C(=O)O1 MNKGJLCEYRTBNX-UHFFFAOYSA-N 0.000 description 1
- WVFQIHLBBWLQGN-UHFFFAOYSA-N 2-[(5-oxo-4h-1,3-oxazol-2-yl)methyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CC1=NCC(=O)O1 WVFQIHLBBWLQGN-UHFFFAOYSA-N 0.000 description 1
- YEGYPUXZMURDLE-UHFFFAOYSA-N 2-[10-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)decyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCCCCCCCC1=NC(C)(C)C(=O)O1 YEGYPUXZMURDLE-UHFFFAOYSA-N 0.000 description 1
- DFAWQYROSGGZCU-UHFFFAOYSA-N 2-[10-(5-oxo-4h-1,3-oxazol-2-yl)decyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCCCCCCCCCC1=NCC(=O)O1 DFAWQYROSGGZCU-UHFFFAOYSA-N 0.000 description 1
- QRCCSIXJZWWTKH-UHFFFAOYSA-N 2-[2-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)ethyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCC1=NC(C)(C)C(=O)O1 QRCCSIXJZWWTKH-UHFFFAOYSA-N 0.000 description 1
- VLHWFGPIHRTPLY-UHFFFAOYSA-N 2-[2-(4-oxo-3,1-benzoxazin-2-yl)ethyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CCC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 VLHWFGPIHRTPLY-UHFFFAOYSA-N 0.000 description 1
- PQJFVRDLOVJMPY-UHFFFAOYSA-N 2-[2-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)ethyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CCC1=NC(C(C)C)C(=O)O1 PQJFVRDLOVJMPY-UHFFFAOYSA-N 0.000 description 1
- VEENQZKPWOABER-UHFFFAOYSA-N 2-[2-(5-oxo-4h-1,3-oxazol-2-yl)ethyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCC1=NCC(=O)O1 VEENQZKPWOABER-UHFFFAOYSA-N 0.000 description 1
- SORNEPWIFZWRMH-UHFFFAOYSA-N 2-[3-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C=3C=CC=C(C=3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 SORNEPWIFZWRMH-UHFFFAOYSA-N 0.000 description 1
- JRCBWKUHJXPNEX-UHFFFAOYSA-N 2-[3-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)phenyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1C1=CC=CC(C=2OC(=O)C(C(C)C)N=2)=C1 JRCBWKUHJXPNEX-UHFFFAOYSA-N 0.000 description 1
- ZBSAQMZWFNJJAY-UHFFFAOYSA-N 2-[3-(5-oxo-4h-1,3-oxazol-2-yl)phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1C1=CC=CC(C=2OC(=O)CN=2)=C1 ZBSAQMZWFNJJAY-UHFFFAOYSA-N 0.000 description 1
- GCKLGLKRQJLXNN-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)butyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCC1=NC(C)(C)C(=O)O1 GCKLGLKRQJLXNN-UHFFFAOYSA-N 0.000 description 1
- IQDGOCFFOPHWLN-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)butyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CCCCC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 IQDGOCFFOPHWLN-UHFFFAOYSA-N 0.000 description 1
- BBITXNWQALLODC-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C3=CC=C(C=C3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 BBITXNWQALLODC-UHFFFAOYSA-N 0.000 description 1
- UYDSINLMNOLIDT-UHFFFAOYSA-N 2-[4-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)butyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CCCCC1=NC(C(C)C)C(=O)O1 UYDSINLMNOLIDT-UHFFFAOYSA-N 0.000 description 1
- ILXWYZXWLRUHJC-UHFFFAOYSA-N 2-[4-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)phenyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1C1=CC=C(C=2OC(=O)C(C(C)C)N=2)C=C1 ILXWYZXWLRUHJC-UHFFFAOYSA-N 0.000 description 1
- VQWJISOFRUNGDF-UHFFFAOYSA-N 2-[4-(5-oxo-4h-1,3-oxazol-2-yl)butyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCCCC1=NCC(=O)O1 VQWJISOFRUNGDF-UHFFFAOYSA-N 0.000 description 1
- XGFJSJXJDMMICL-UHFFFAOYSA-N 2-[4-(5-oxo-4h-1,3-oxazol-2-yl)phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1C1=CC=C(C=2OC(=O)CN=2)C=C1 XGFJSJXJDMMICL-UHFFFAOYSA-N 0.000 description 1
- QYDLRLMAAAQEJO-UHFFFAOYSA-N 2-[6-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)hexyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCCCC1=NC(C)(C)C(=O)O1 QYDLRLMAAAQEJO-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
Description
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Claims (1)
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ç¯å²ç¬¬ïŒïŒé ã®è£œé æ³ã
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7486180A JPS572330A (en) | 1980-06-05 | 1980-06-05 | Preparation of aromatic polyester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7486180A JPS572330A (en) | 1980-06-05 | 1980-06-05 | Preparation of aromatic polyester |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20183986A Division JPS6264826A (ja) | 1986-08-29 | 1986-08-29 | è³éŠæããªãšã¹ãã«æååã®è£œé æ³ |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS572330A JPS572330A (en) | 1982-01-07 |
JPS636090B2 true JPS636090B2 (ja) | 1988-02-08 |
Family
ID=13559522
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7486180A Granted JPS572330A (en) | 1980-06-05 | 1980-06-05 | Preparation of aromatic polyester |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS572330A (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6264826A (ja) * | 1986-08-29 | 1987-03-23 | Teijin Ltd | è³éŠæããªãšã¹ãã«æååã®è£œé æ³ |
-
1980
- 1980-06-05 JP JP7486180A patent/JPS572330A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS572330A (en) | 1982-01-07 |
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