CS200541B2 - Method of producing linear homopolyesters or copolyesters - Google Patents
Method of producing linear homopolyesters or copolyesters Download PDFInfo
- Publication number
- CS200541B2 CS200541B2 CS781196A CS119678A CS200541B2 CS 200541 B2 CS200541 B2 CS 200541B2 CS 781196 A CS781196 A CS 781196A CS 119678 A CS119678 A CS 119678A CS 200541 B2 CS200541 B2 CS 200541B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- ester
- polyester
- stabilizing agent
- copolyesters
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 229920001634 Copolyester Polymers 0.000 title claims description 6
- 229920000728 polyester Polymers 0.000 claims abstract description 36
- 239000003381 stabilizer Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000006068 polycondensation reaction Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 7
- 239000011574 phosphorus Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- -1 hydroxyl compound Chemical class 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000012760 heat stabilizer Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 3
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical class CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000007014 Michaelis-Becker reaction Methods 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 2
- 229940119177 germanium dioxide Drugs 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 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 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-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
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 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
- CMTHUKRBWPWGHX-UHFFFAOYSA-N 1-dimethoxyphosphoryl-1-methoxyethane Chemical compound COC(C)P(=O)(OC)OC CMTHUKRBWPWGHX-UHFFFAOYSA-N 0.000 description 1
- RYRZSXJVEILFRR-UHFFFAOYSA-N 2,3-dimethylterephthalic acid Chemical compound CC1=C(C)C(C(O)=O)=CC=C1C(O)=O RYRZSXJVEILFRR-UHFFFAOYSA-N 0.000 description 1
- CCEIRYAIQPIQFO-UHFFFAOYSA-N 2-bis[2-(2-bromoethyl)phenoxy]phosphorylethylphosphonic acid Chemical compound C1=CC=C(C(=C1)CCBr)OP(=O)(CCP(=O)(O)O)OC2=CC=CC=C2CCBr CCEIRYAIQPIQFO-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-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
- QJGNSTCICFBACB-UHFFFAOYSA-N 2-octylpropanedioic acid Chemical compound CCCCCCCCC(C(O)=O)C(O)=O QJGNSTCICFBACB-UHFFFAOYSA-N 0.000 description 1
- RGUZWBOJHNWZOK-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2-diol Chemical compound CC1=CC=C(C)C(O)=C1O RGUZWBOJHNWZOK-UHFFFAOYSA-N 0.000 description 1
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- YKWPKCGAYIYEHB-UHFFFAOYSA-N CCCC(OC)P(=O)(OC)OC Chemical compound CCCC(OC)P(=O)(OC)OC YKWPKCGAYIYEHB-UHFFFAOYSA-N 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 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
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 description 1
- JMJWCUOIOKBVNQ-UHFFFAOYSA-N ethyl 3-diethoxyphosphorylpropanoate Chemical compound CCOC(=O)CCP(=O)(OCC)OCC JMJWCUOIOKBVNQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 1
- YATNMHXCCAUZTH-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylbutanoate Chemical compound COC(=O)C(CC)P(=O)(OC)OC YATNMHXCCAUZTH-UHFFFAOYSA-N 0.000 description 1
- DHZKKMDGNCSNPK-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylpentanoate Chemical compound CCCC(C(=O)OC)P(=O)(OC)OC DHZKKMDGNCSNPK-UHFFFAOYSA-N 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
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6926—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2708790A DE2708790C2 (de) | 1977-03-01 | 1977-03-01 | Lineare Homo- oder Copolyester, Verfahren zur Herstellung der Polyester und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200541B2 true CS200541B2 (en) | 1980-09-15 |
Family
ID=6002463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS781196A CS200541B2 (en) | 1977-03-01 | 1978-02-24 | Method of producing linear homopolyesters or copolyesters |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4254018A (de) |
| JP (1) | JPS53106751A (de) |
| AR (1) | AR217679A1 (de) |
| AT (1) | AT370751B (de) |
| BR (1) | BR7801202A (de) |
| CH (1) | CH640547A5 (de) |
| CS (1) | CS200541B2 (de) |
| DE (1) | DE2708790C2 (de) |
| ES (1) | ES467183A1 (de) |
| FR (1) | FR2382476A1 (de) |
| GB (1) | GB1568190A (de) |
| IT (1) | IT1102726B (de) |
| LU (1) | LU79133A1 (de) |
| MX (1) | MX148902A (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539355A (en) * | 1982-06-23 | 1985-09-03 | Sumitomo Chemical Company, Limited | Phosphorus-containing compounds, their production and their use as antioxidants |
| DE4327616A1 (de) * | 1993-08-17 | 1995-02-23 | Hoechst Ag | Verfahren zur Herstellung von Polyestern mit verbessertem Weißgrad |
| GB2313126A (en) * | 1996-05-14 | 1997-11-19 | Albright & Wilson Uk Ltd | Polymer compositions containing phosphorus |
| DE19631069A1 (de) * | 1996-08-01 | 1998-02-05 | Zimmer Ag | POY-Polyesterfaser für Strecktexturierung und Verfahren zu deren Herstellung |
| DE19915683A1 (de) * | 1998-04-30 | 1999-11-11 | Inventa Ag | Polyesterfasern und -filamente und Verfahren zu deren Herstellung |
| US6384180B1 (en) | 1999-08-24 | 2002-05-07 | Eastman Chemical Company | Method for making polyesters employing acidic phosphorus-containing compounds |
| JP3209336B1 (ja) * | 2000-05-17 | 2001-09-17 | エスケー ケミカルズ カンパニー リミテッド | １，４−シクロヘキサンジメタノールが共重合されたポリエステル樹脂の製造方法 |
| ITMI20011206A1 (it) * | 2001-06-07 | 2002-12-07 | Montefibre Spa | Procedimento per la preparazione di resine poliesteri |
| ES2296998T3 (es) * | 2001-09-20 | 2008-05-01 | Teijin Limited | Procedimiento para producir resina de poli(ester dicarboxilato aromatico de etileno) y productos de la resina. |
| TW200408531A (en) * | 2002-09-05 | 2004-06-01 | Teijin Dupont Films Japan Ltd | Base film for membrane switch and membrane switch |
| EP1433806A1 (de) * | 2002-12-03 | 2004-06-30 | Nan Ya Plastics Corp. | Methode zur Reduzierung des Gehaltes an zyklischen Oligomeren in Polyester-Produkten |
| US20060057373A1 (en) * | 2003-01-07 | 2006-03-16 | Teijin Fibers Limited | Polyester fiber structures |
| CA2513056A1 (en) * | 2003-01-09 | 2004-07-29 | Teijin Fibers Limited | Polyester fiber knitted or woven fabric |
| DE60327716D1 (de) * | 2003-01-14 | 2009-07-02 | Teijin Fibers Ltd | Polyesterfasern mit verformtem profil |
| JP2004218125A (ja) * | 2003-01-14 | 2004-08-05 | Teijin Fibers Ltd | 異形断面ポリエステル繊維の製造方法 |
| RU2303090C2 (ru) * | 2003-01-14 | 2007-07-20 | Тейдзин Файберз Лимитед | Волокна из сложного полиэфира с модифицированным поперечным сечением |
| AU2003292688A1 (en) * | 2003-01-16 | 2004-08-10 | Teijin Fibers Limited | Polyester fiber and false twist yarn comprising the same |
| RU2303091C2 (ru) * | 2003-01-16 | 2007-07-20 | Тейдзин Файберз Лимитед | Смешанная пряжа с элементарными нитями с различными степенями усадки из сложных полиэфиров |
| CA2513348A1 (en) * | 2003-01-16 | 2004-07-29 | Teijin Fibers Limited | Differential-shrinkage polyester combined filament yarn |
| JP2004218158A (ja) * | 2003-01-16 | 2004-08-05 | Teijin Fibers Ltd | ポリエステル繊維及びそれからなる仮撚加工糸 |
| JP4064273B2 (ja) * | 2003-03-20 | 2008-03-19 | 帝人ファイバー株式会社 | ポリエステル繊維の製造方法 |
| DE102004046771A1 (de) | 2004-09-24 | 2006-04-06 | Zimmer Ag | Mischung, Polyesterzusammensetzung, Folie sowie Verfahren zu deren Herstellung |
| WO2006057228A1 (ja) * | 2004-11-24 | 2006-06-01 | Toyo Boseki Kabushiki Kaisha | 難燃性ポリエステル及びその製造方法 |
| EP1719795A1 (de) * | 2005-04-13 | 2006-11-08 | Huntsman Textile Effects (Germany) GmbH | Umsetzungsprodukte von Phosphonoestern mit Alkoholen oder Aminen |
| CA2607987A1 (en) * | 2005-05-20 | 2006-11-23 | Ciba Specialty Chemicals Holding, Inc. | Process for improving the thermal and light stability of polyesters |
| EP3000835B1 (de) * | 2014-09-24 | 2020-11-25 | Clariant International Ltd | Katalysatorzusammensetzung für einen Polyesterherstellungsprozess |
| CN114341266A (zh) | 2019-09-05 | 2022-04-12 | 巴斯夫欧洲公司 | 耐热的热塑性模塑组合物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL75176C (de) * | 1948-06-24 | |||
| US2652416A (en) * | 1952-01-02 | 1953-09-15 | Eastman Kodak Co | Reaction of lactones with trialkyl phosphite |
| US2963458A (en) * | 1958-01-14 | 1960-12-06 | Swern Daniel | Vinyl chloride polymer plasticized with alpha-phosphonate compounds |
| NL248141A (de) * | 1959-02-18 | |||
| DE1122252B (de) * | 1959-07-17 | 1962-01-18 | Bayer Ag | Verfahren zur Herstellung von phosphor- und halogenhaltigen geformten Kunstoffen mit hoher Flammfestigkeit auf der Grundlage von ungesaettigten Polyestern |
| NL280017A (de) * | 1961-06-24 | |||
| US3546177A (en) * | 1968-03-07 | 1970-12-08 | Eastman Kodak Co | Polyesters containing sterically hindered trialkyl phosphates |
| US3649722A (en) * | 1968-09-26 | 1972-03-14 | Procter & Gamble | Halogenated phosphonoacetate esters |
| DE2047195A1 (de) * | 1970-09-25 | 1972-03-30 | Kalk Chemische Fabrik Gmbh | Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren Herstellung |
| JPS5232670B2 (de) * | 1973-04-03 | 1977-08-23 | ||
| US3801542A (en) * | 1973-04-23 | 1974-04-02 | Stauffer Chemical Co | Bis(alpha,beta-dihaloalkyl)1-acyloxyalkane phosphonate flame retardants |
| US4133800A (en) * | 1974-01-28 | 1979-01-09 | Imperial Chemical Industries Limited | Polyester production |
| US3959213A (en) * | 1974-08-29 | 1976-05-25 | Eastman Kodak Company | Basic dyeable polyester fiber |
| GB1522081A (en) * | 1975-01-17 | 1978-08-23 | Toyo Boseki | Flame resistant polyesters |
| JPS5273996A (en) * | 1975-12-18 | 1977-06-21 | Teijin Ltd | Preparation of polyesters |
| US4062829A (en) * | 1976-11-08 | 1977-12-13 | Emery Industries, Inc. | Polyester compositions and methods of stabilizing same |
| DE2726189A1 (de) * | 1977-06-10 | 1978-12-21 | Hoechst Ag | Flammwidrig ausgeruestete, biaxial orientierte polyesterfolie |
-
1977
- 1977-03-01 DE DE2708790A patent/DE2708790C2/de not_active Expired
-
1978
- 1978-01-31 AT AT0065378A patent/AT370751B/de not_active IP Right Cessation
- 1978-02-20 CH CH179878A patent/CH640547A5/de not_active IP Right Cessation
- 1978-02-21 ES ES467183A patent/ES467183A1/es not_active Expired
- 1978-02-22 AR AR271195A patent/AR217679A1/es active
- 1978-02-24 CS CS781196A patent/CS200541B2/cs unknown
- 1978-02-27 FR FR7805608A patent/FR2382476A1/fr active Granted
- 1978-02-27 LU LU79133A patent/LU79133A1/de unknown
- 1978-02-27 IT IT48205/78A patent/IT1102726B/it active
- 1978-02-28 BR BR7801202A patent/BR7801202A/pt unknown
- 1978-02-28 JP JP2273978A patent/JPS53106751A/ja active Pending
- 1978-02-28 MX MX172581A patent/MX148902A/es unknown
- 1978-02-28 GB GB7855/78A patent/GB1568190A/en not_active Expired
- 1978-03-01 US US05/882,097 patent/US4254018A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4254018A (en) | 1981-03-03 |
| IT1102726B (it) | 1985-10-07 |
| FR2382476B1 (de) | 1982-04-23 |
| DE2708790A1 (de) | 1978-09-07 |
| GB1568190A (en) | 1980-05-29 |
| AT370751B (de) | 1983-05-10 |
| DE2708790C2 (de) | 1982-02-25 |
| CH640547A5 (de) | 1984-01-13 |
| LU79133A1 (de) | 1978-06-27 |
| ATA65378A (de) | 1982-09-15 |
| JPS53106751A (en) | 1978-09-18 |
| FR2382476A1 (fr) | 1978-09-29 |
| AR217679A1 (es) | 1980-04-15 |
| MX148902A (es) | 1983-06-30 |
| BR7801202A (pt) | 1978-10-10 |
| ES467183A1 (es) | 1978-12-16 |
| IT7848205A0 (it) | 1978-02-27 |
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