TWI336713B - Production process for polyester, polyester composition and polyester fiber - Google Patents
Production process for polyester, polyester composition and polyester fiber Download PDFInfo
- Publication number
- TWI336713B TWI336713B TW93118019A TW93118019A TWI336713B TW I336713 B TWI336713 B TW I336713B TW 93118019 A TW93118019 A TW 93118019A TW 93118019 A TW93118019 A TW 93118019A TW I336713 B TWI336713 B TW I336713B
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- TW
- Taiwan
- Prior art keywords
- polyester
- compound
- acid
- titanium
- group
- Prior art date
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- 229920000728 polyester Polymers 0.000 title claims description 296
- 239000000203 mixture Substances 0.000 title claims description 256
- 238000004519 manufacturing process Methods 0.000 title claims description 67
- 239000000835 fiber Substances 0.000 title claims description 65
- 229910052698 phosphorus Inorganic materials 0.000 claims description 317
- 239000011574 phosphorus Substances 0.000 claims description 281
- -1 phosphorus compound Chemical class 0.000 claims description 235
- 239000010936 titanium Substances 0.000 claims description 108
- 229910052719 titanium Inorganic materials 0.000 claims description 98
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 96
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 93
- 150000003609 titanium compounds Chemical class 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 71
- 125000004437 phosphorous atom Chemical group 0.000 claims description 37
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 36
- 229910052751 metal Inorganic materials 0.000 claims description 35
- 239000002184 metal Substances 0.000 claims description 35
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000002245 particle Substances 0.000 claims description 27
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 24
- 239000011572 manganese Substances 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 15
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 14
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 150000002697 manganese compounds Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004185 ester group Chemical group 0.000 claims description 11
- 229910052748 manganese Inorganic materials 0.000 claims description 11
- 239000004745 nonwoven fabric Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 238000009958 sewing Methods 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000002743 phosphorus functional group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 164
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 126
- 239000000243 solution Substances 0.000 description 67
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 66
- 229920000642 polymer Polymers 0.000 description 62
- 239000000306 component Substances 0.000 description 53
- 229940125904 compound 1 Drugs 0.000 description 45
- 238000002074 melt spinning Methods 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 41
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 38
- 238000009987 spinning Methods 0.000 description 38
- 229940126062 Compound A Drugs 0.000 description 34
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000002253 acid Substances 0.000 description 29
- 238000006116 polymerization reaction Methods 0.000 description 28
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 24
- 235000015165 citric acid Nutrition 0.000 description 22
- 229960004106 citric acid Drugs 0.000 description 22
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 21
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 20
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 19
- 239000013522 chelant Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000002002 slurry Substances 0.000 description 13
- 229920000139 polyethylene terephthalate Polymers 0.000 description 12
- 239000005020 polyethylene terephthalate Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- 229940071125 manganese acetate Drugs 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 239000004744 fabric Substances 0.000 description 10
- 239000004310 lactic acid Substances 0.000 description 10
- 235000014655 lactic acid Nutrition 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 239000000052 vinegar Substances 0.000 description 10
- 235000021419 vinegar Nutrition 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 9
- 239000002685 polymerization catalyst Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000008358 core component Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000004408 titanium dioxide Substances 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 150000001463 antimony compounds Chemical class 0.000 description 5
- 229940011182 cobalt acetate Drugs 0.000 description 5
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 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 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000004594 Masterbatch (MB) Substances 0.000 description 3
- DEMJYWYZJFNNNB-UHFFFAOYSA-N OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O Chemical compound OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O DEMJYWYZJFNNNB-UHFFFAOYSA-N 0.000 description 3
- FHQZHFOPHNMDHU-UHFFFAOYSA-N P(O)(O)O.P(O)(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(C(C)(C)C)(O)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C Chemical compound P(O)(O)O.P(O)(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(C(C)(C)C)(O)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C FHQZHFOPHNMDHU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JBTXGEJRJCNRLU-UHFFFAOYSA-N [2-(dihydroxyphosphanyloxymethyl)-3-hydroxy-2-(hydroxymethyl)propyl] dihydrogen phosphite Chemical compound OP(O)OCC(CO)(CO)COP(O)O JBTXGEJRJCNRLU-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 150000001869 cobalt compounds Chemical class 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- DMDRBXCDTZRMHZ-UHFFFAOYSA-N 1,4-bis(2,4,6-trimethylanilino)anthracene-9,10-dione Chemical compound CC1=CC(C)=CC(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C=C1C DMDRBXCDTZRMHZ-UHFFFAOYSA-N 0.000 description 2
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 2
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- TYFJTEPDESMEHE-UHFFFAOYSA-N 6,8-dihydroxy-3-[2-(4-methoxyphenyl)ethyl]-3,4-dihydroisochromen-1-one Chemical compound C1=CC(OC)=CC=C1CCC1OC(=O)C2=C(O)C=C(O)C=C2C1 TYFJTEPDESMEHE-UHFFFAOYSA-N 0.000 description 2
- PQNIFBMBZQFSNO-UHFFFAOYSA-L C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].[Mn+2] Chemical compound C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].[Mn+2] PQNIFBMBZQFSNO-UHFFFAOYSA-L 0.000 description 2
- AFEBURQVBVFCHW-UHFFFAOYSA-N CC(C)P(O)=O Chemical compound CC(C)P(O)=O AFEBURQVBVFCHW-UHFFFAOYSA-N 0.000 description 2
- MTWVYGIIHVUGNL-UHFFFAOYSA-N CCCCP(O)=O Chemical compound CCCCP(O)=O MTWVYGIIHVUGNL-UHFFFAOYSA-N 0.000 description 2
- DGLXNOJGOHKWTN-UHFFFAOYSA-N CCCP(O)=O Chemical compound CCCP(O)=O DGLXNOJGOHKWTN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
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- 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
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- 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
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- 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
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- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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- 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
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- 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
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- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2003182227A JP4329427B2 (ja) | 2003-06-26 | 2003-06-26 | ポリエステル組成物及びそれからなる繊維 |
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| TW200504114A TW200504114A (en) | 2005-02-01 |
| TWI336713B true TWI336713B (en) | 2011-02-01 |
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| TW93118019A TWI336713B (en) | 2003-06-26 | 2004-06-23 | Production process for polyester, polyester composition and polyester fiber |
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| JP (1) | JP4329427B2 (enExample) |
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| MY (1) | MY138779A (enExample) |
| TW (1) | TWI336713B (enExample) |
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| CN1938461B (zh) * | 2004-03-30 | 2011-04-27 | 帝人纤维株式会社 | 海岛型复合纤维及其制造方法 |
| DE102005018617A1 (de) * | 2005-04-21 | 2006-10-26 | Mitsubishi Polyester Film Gmbh | Biaxial orientierte Folie auf Basis von titankatalysierten Polyestern |
| JP2007056420A (ja) * | 2005-08-26 | 2007-03-08 | Toray Ind Inc | カチオン可染性制電性ポリエステル繊維 |
| JP2007063714A (ja) * | 2005-08-31 | 2007-03-15 | Toray Ind Inc | ポリエステル極細繊維および布帛 |
| JP2007063713A (ja) * | 2005-08-31 | 2007-03-15 | Toray Ind Inc | 染色性に優れたポリエステル未延伸糸 |
| CN101346409B (zh) | 2005-12-23 | 2012-05-30 | 东丽纤维研究所（中国）有限公司 | 用于制备聚酯的催化剂和聚酯的制备方法 |
| CN101328263B (zh) * | 2007-06-22 | 2012-06-06 | 东丽纤维研究所（中国）有限公司 | 生产聚酯用催化剂 |
| JPWO2009088008A1 (ja) * | 2008-01-08 | 2011-05-26 | 帝人ファイバー株式会社 | 常圧カチオン可染性ポリエステル及び繊維 |
| CN101525418B (zh) * | 2008-03-04 | 2012-01-18 | 东丽纤维研究所（中国）有限公司 | 大有光聚对苯二甲酸乙二醇酯 |
| CN101555345B (zh) * | 2008-04-09 | 2012-07-25 | 东丽纤维研究所（中国）有限公司 | 一种具有良好色相磷系共聚阻燃聚酯的制备方法 |
| EP2210910B1 (en) | 2009-01-21 | 2013-01-02 | Nan Ya Plastics Corporation | Antimony-free PET resin and PET polyester fiber made therefrom |
| JP2010180270A (ja) * | 2009-02-03 | 2010-08-19 | Nan Ya Plast Corp | アンチモン非含有ｐｅｔ樹脂およびそれよりなるポリエステル繊維 |
| JP5746684B2 (ja) * | 2009-04-24 | 2015-07-08 | ユニリーバー・ナームローゼ・ベンノートシヤープ | ヘアスタイリング組成物 |
| KR101700630B1 (ko) * | 2009-09-14 | 2017-01-31 | 미쓰비시 쥬시 가부시끼가이샤 | 태양전지 이면 봉지용 2축 배향 폴리에스테르 필름 |
| CN102453239B (zh) * | 2010-10-21 | 2015-08-05 | 东丽纤维研究所（中国）有限公司 | 聚酯组合物及其生产方法 |
| KR101303819B1 (ko) * | 2011-05-31 | 2013-09-04 | 웅진케미칼 주식회사 | 저융점 항균성 재생 폴리에스테르 필라멘트 및 그 제조방법 |
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| US10017629B2 (en) | 2014-02-20 | 2018-07-10 | Teijin Limited | Polyethylene-2,6-naphthalate composition with excellent blow moldability, and molded product thereof |
| DE202015005969U1 (de) | 2015-08-27 | 2015-09-28 | Carl Freudenberg Kg | Vliesstoff umfassend antimonfreien Polyester |
| EP3466385B1 (en) | 2017-10-06 | 2020-05-27 | The Procter & Gamble Company | Absorbent article or wipe comprising a nonwoven material with bicomponent fibers comprising antimony-free polyethylene terephthalate |
| EP3466388B1 (en) * | 2017-10-06 | 2020-05-20 | The Procter & Gamble Company | Absorbent article comprising a nonwoven material with antimony-free polyethylene terephthalate |
| EP3466389B1 (en) | 2017-10-06 | 2020-05-20 | The Procter & Gamble Company | Absorbent article comprising a carded resin-bonded nonwoven web with fibers comprising antimony-free polyethylene terephthalate |
| US11661683B2 (en) * | 2018-03-29 | 2023-05-30 | Milliken & Company | Flame resistant textile |
| CN111019100B (zh) * | 2018-10-10 | 2022-05-03 | 中国石油化工股份有限公司 | 一种蒙脱土改性的阻隔聚酯及其制备方法 |
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| CN115353754B (zh) * | 2022-09-26 | 2023-03-03 | 福建乐钛科技有限公司 | 涤纶色母粒用钛白粉的制备方法 |
| CN119613218B (zh) * | 2024-11-25 | 2025-11-18 | 山东科技大学 | 一种丁基膦酸修饰的镁基加氢脱硫材料及其制备方法 |
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| AT313584B (de) | 1969-05-02 | 1974-02-25 | Goodyear Tire & Rubber | Verfahren zur Herstellung linearer Polyester |
| JP2865979B2 (ja) | 1993-07-13 | 1999-03-08 | 帝人株式会社 | 芳香族ポリエステルの製造方法 |
| DE69731532T2 (de) * | 1996-06-11 | 2006-03-02 | DuPont Teijin Films U.S., Ltd. Partnership, Wilmington | Verfahren zur Herstellung eines Polyesterpolymers |
| JPH10259296A (ja) | 1997-03-21 | 1998-09-29 | Kuraray Co Ltd | 熱安定性に優れたポリエステル |
| GB9725419D0 (en) | 1997-12-02 | 1998-01-28 | Tioxide Specialties Ltd | Esterification catalysts |
| CN1297376A (zh) | 1998-04-17 | 2001-05-30 | 纳幕尔杜邦公司 | 包含钛、胺、磷化合物的催化剂组合物及其制备和用途 |
| JP3998942B2 (ja) | 2001-01-26 | 2007-10-31 | 帝人ファイバー株式会社 | ポリエステル製造用触媒及びそれを用いるポリエステル製造方法 |
| US6489433B2 (en) | 2001-02-23 | 2002-12-03 | E. I. Du Pont De Nemours And Company | Metal-containing composition and process therewith |
| JP4930665B2 (ja) | 2001-08-01 | 2012-05-16 | 東洋紡績株式会社 | ポリエステル重合触媒及びポリエステルの製造方法（オルトエステル） |
| JP2003040991A (ja) | 2001-08-01 | 2003-02-13 | Toyobo Co Ltd | ポリエステル、ポリエステル重合触媒及びポリエステルの製造方法 |
| JP2003147060A (ja) | 2001-11-15 | 2003-05-21 | Mitsubishi Chemicals Corp | 共重合ポリエステル樹脂の製造方法 |
-
2003
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2004
- 2004-06-23 TW TW93118019A patent/TWI336713B/zh not_active IP Right Cessation
- 2004-06-25 US US10/875,557 patent/US7144974B2/en not_active Expired - Lifetime
- 2004-06-25 KR KR1020040048444A patent/KR101113117B1/ko not_active Expired - Fee Related
- 2004-06-25 MY MYPI20042497A patent/MY138779A/en unknown
- 2004-06-28 EP EP20040253857 patent/EP1491572A1/en not_active Withdrawn
- 2004-06-28 CN CN2004100594523A patent/CN1576292B/zh not_active Expired - Fee Related
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|---|---|
| MY138779A (en) | 2009-07-31 |
| CN1576292B (zh) | 2010-08-25 |
| JP4329427B2 (ja) | 2009-09-09 |
| JP2005015630A (ja) | 2005-01-20 |
| US20040266978A1 (en) | 2004-12-30 |
| KR20050002567A (ko) | 2005-01-07 |
| CN1576292A (zh) | 2005-02-09 |
| TW200504114A (en) | 2005-02-01 |
| KR101113117B1 (ko) | 2012-03-13 |
| US7144974B2 (en) | 2006-12-05 |
| EP1491572A1 (en) | 2004-12-29 |
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