JPH0248173B2 - Hokozokuhoriesuteruseikeihinnoseizoho - Google Patents
HokozokuhoriesuteruseikeihinnoseizohoInfo
- Publication number
- JPH0248173B2 JPH0248173B2 JP20184086A JP20184086A JPH0248173B2 JP H0248173 B2 JPH0248173 B2 JP H0248173B2 JP 20184086 A JP20184086 A JP 20184086A JP 20184086 A JP20184086 A JP 20184086A JP H0248173 B2 JPH0248173 B2 JP H0248173B2
- Authority
- JP
- Japan
- Prior art keywords
- aromatic polyester
- molded article
- terminal carboxyl
- producing
- aromatic
- 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 - Lifetime
Links
- 229920000728 polyester Polymers 0.000 claims description 274
- 125000003118 aryl group Chemical group 0.000 claims description 254
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 154
- -1 alkylene glycol Chemical compound 0.000 claims description 118
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 110
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 107
- 238000006243 chemical reaction Methods 0.000 claims description 105
- 238000006116 polymerization reaction Methods 0.000 claims description 81
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 60
- 239000002253 acid Substances 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 28
- 238000000465 moulding Methods 0.000 claims description 28
- 239000000155 melt Substances 0.000 claims description 21
- 238000002844 melting Methods 0.000 claims description 18
- 230000008018 melting Effects 0.000 claims description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229920005992 thermoplastic resin Polymers 0.000 claims description 14
- 239000012778 molding material Substances 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 claims description 5
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 claims description 5
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 10
- 150000001491 aromatic compounds Chemical class 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 66
- 229920000642 polymer Polymers 0.000 description 46
- 239000000047 product Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 38
- 229920000139 polyethylene terephthalate Polymers 0.000 description 38
- 239000005020 polyethylene terephthalate Substances 0.000 description 38
- 150000008064 anhydrides Chemical class 0.000 description 32
- 239000008188 pellet Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 24
- KKKKCPPTESQGQH-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=NCCO1 KKKKCPPTESQGQH-UHFFFAOYSA-N 0.000 description 20
- 150000002430 hydrocarbons Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 239000000835 fiber Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- HUPHGMKBBSQNKV-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole-2-carboxamide Chemical compound NC(=O)C1=NCCO1 HUPHGMKBBSQNKV-UHFFFAOYSA-N 0.000 description 12
- 238000001125 extrusion Methods 0.000 description 12
- 238000009987 spinning Methods 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 8
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical compound C1COC=NC1 YWOIQIYQBRDOQA-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VOGDKZZTBPDRBD-UHFFFAOYSA-N 2-[2-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1C1=NCCO1 VOGDKZZTBPDRBD-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000002981 blocking agent Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000002074 melt spinning Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- VCKMMTTWCKGKKY-UHFFFAOYSA-N 3-[2-(2-carbamoyl-1,3-oxazinan-3-yl)ethyl]-1,3-oxazinane-2-carboxamide Chemical compound NC(=O)C1OCCCN1CCN1C(C(N)=O)OCCC1 VCKMMTTWCKGKKY-UHFFFAOYSA-N 0.000 description 2
- YTDWINDMGUQTBS-UHFFFAOYSA-N 4-hexyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCC1COC=N1 YTDWINDMGUQTBS-UHFFFAOYSA-N 0.000 description 2
- IFIUFEBEPGGBIJ-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC=N1 IFIUFEBEPGGBIJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 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 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011521 glass Substances 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
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 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
- 150000003891 oxalate salts Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920001281 polyalkylene Polymers 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
- 239000000843 powder Substances 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
- 238000010992 reflux Methods 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-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
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- WIJHUWWUJBVBPD-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2OCCN=2)=N1 WIJHUWWUJBVBPD-UHFFFAOYSA-N 0.000 description 1
- FRQIBBYGBMZVCQ-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C=2OCCN=2)=N1 FRQIBBYGBMZVCQ-UHFFFAOYSA-N 0.000 description 1
- URRFGQUOWOILSP-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-5,6-dihydro-4h-1,3-oxazine Chemical compound O1CCN=C1C1=NCCCO1 URRFGQUOWOILSP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- AWZAKUFLIAIORL-UHFFFAOYSA-N 2-[3-(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=CC(C=2OC(=O)C(C)(C)N=2)=C1 AWZAKUFLIAIORL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ROVLJQDICPLANK-UHFFFAOYSA-N 2-ethoxy-3-hydroxybenzoic acid Chemical compound CCOC1=C(O)C=CC=C1C(O)=O ROVLJQDICPLANK-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 1
- XFDQYYUJIBWHQS-UHFFFAOYSA-N 3,10-dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene-2,11-dione Chemical compound O=C1OCCCCCCOC(=O)C2=CC=C1C=C2 XFDQYYUJIBWHQS-UHFFFAOYSA-N 0.000 description 1
- CQZPWWXBOUBLMX-UHFFFAOYSA-N 3-[10-(2-carbamoyl-1,3-oxazinan-3-yl)decyl]-1,3-oxazinane-2-carboxamide Chemical compound NC(=O)C1OCCCN1CCCCCCCCCCN1C(C(N)=O)OCCC1 CQZPWWXBOUBLMX-UHFFFAOYSA-N 0.000 description 1
- YRCCNENMHWNWKD-UHFFFAOYSA-N 3-[2-(2-carbamoyl-1,3-oxazinan-3-yl)phenyl]-1,3-oxazinane-2-carboxamide Chemical compound NC(=O)C1OCCCN1C1=CC=CC=C1N1C(C(N)=O)OCCC1 YRCCNENMHWNWKD-UHFFFAOYSA-N 0.000 description 1
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- TYUWZAWZLNQJLG-UHFFFAOYSA-N 3-[3-(2-carbamoyl-1,3-oxazinan-3-yl)propyl]-1,3-oxazinane-2-carboxamide Chemical compound NC(=O)C1OCCCN1CCCN1C(C(N)=O)OCCC1 TYUWZAWZLNQJLG-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Description
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è³éŠæããªãšã¹ãã«ããæãæååã®è£œé æ³ã
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20184086A JPH0248173B2 (ja) | 1986-08-29 | 1986-08-29 | Hokozokuhoriesuteruseikeihinnoseizoho |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20184086A JPH0248173B2 (ja) | 1986-08-29 | 1986-08-29 | Hokozokuhoriesuteruseikeihinnoseizoho |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7657980A Division JPS572335A (en) | 1980-06-09 | 1980-06-09 | Preparation of aromatic polyester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6284128A JPS6284128A (ja) | 1987-04-17 |
| JPH0248173B2 true JPH0248173B2 (ja) | 1990-10-24 |
Family
ID=16447763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20184086A Expired - Lifetime JPH0248173B2 (ja) | 1986-08-29 | 1986-08-29 | Hokozokuhoriesuteruseikeihinnoseizoho |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0248173B2 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010235824A (ja) * | 2009-03-31 | 2010-10-21 | Toray Ind Inc | äºè»žé åããªãšã¹ãã«ãã£ã«ã |
-
1986
- 1986-08-29 JP JP20184086A patent/JPH0248173B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010235824A (ja) * | 2009-03-31 | 2010-10-21 | Toray Ind Inc | äºè»žé åããªãšã¹ãã«ãã£ã«ã |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6284128A (ja) | 1987-04-17 |
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