KR20020030794A - 폴리에스테르 중합촉매 및 이것을 사용하여 제조된폴리에스테르 및 폴리에스테르의 제조방법 - Google Patents
폴리에스테르 중합촉매 및 이것을 사용하여 제조된폴리에스테르 및 폴리에스테르의 제조방법 Download PDFInfo
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- KR20020030794A KR20020030794A KR1020027002253A KR20027002253A KR20020030794A KR 20020030794 A KR20020030794 A KR 20020030794A KR 1020027002253 A KR1020027002253 A KR 1020027002253A KR 20027002253 A KR20027002253 A KR 20027002253A KR 20020030794 A KR20020030794 A KR 20020030794A
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- Prior art keywords
- acid
- polyester
- compounds
- compound
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- 229920000728 polyester Polymers 0.000 title claims abstract description 81
- 239000002685 polymerization catalyst Substances 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 8
- -1 aluminum compound Chemical class 0.000 claims abstract description 95
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 24
- 239000011574 phosphorus Substances 0.000 claims abstract description 24
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003009 phosphonic acids Chemical class 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 238000006068 polycondensation reaction Methods 0.000 abstract description 33
- 150000001463 antimony compounds Chemical class 0.000 abstract description 9
- 239000000835 fiber Substances 0.000 abstract description 4
- 229920006351 engineering plastic Polymers 0.000 abstract description 3
- 239000012770 industrial material Substances 0.000 abstract description 3
- 238000000465 moulding Methods 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 58
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 20
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 18
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 description 11
- 239000005020 polyethylene terephthalate Substances 0.000 description 11
- 229910052787 antimony Inorganic materials 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 150000002334 glycols Chemical class 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 150000003018 phosphorus compounds Chemical class 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 4
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002291 germanium compounds Chemical class 0.000 description 4
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 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
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229960000380 propiolactone Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- JTGJSHWRMGFNQK-UHFFFAOYSA-N (2-methylphenyl)-phenylphosphinic acid Chemical compound CC1=CC=CC=C1P(O)(=O)C1=CC=CC=C1 JTGJSHWRMGFNQK-UHFFFAOYSA-N 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- CEGRHPCDLKAHJD-UHFFFAOYSA-N 1,1,1-propanetricarboxylic acid Chemical compound CCC(C(O)=O)(C(O)=O)C(O)=O CEGRHPCDLKAHJD-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 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 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 2
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 2
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 description 2
- AOCDMIRIBTWZTI-UHFFFAOYSA-N 2-dimethylphosphorylbutanedioic acid Chemical compound CP(C)(=O)C(C(O)=O)CC(O)=O AOCDMIRIBTWZTI-UHFFFAOYSA-N 0.000 description 2
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 2
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 2
- QXFUBAAEKCHBQY-UHFFFAOYSA-N 3-[hydroxy(methyl)phosphoryl]propanoic acid Chemical compound CP(O)(=O)CCC(O)=O QXFUBAAEKCHBQY-UHFFFAOYSA-N 0.000 description 2
- MORLYCDUFHDZKO-UHFFFAOYSA-N 3-[hydroxy(phenyl)phosphoryl]propanoic acid Chemical compound OC(=O)CCP(O)(=O)C1=CC=CC=C1 MORLYCDUFHDZKO-UHFFFAOYSA-N 0.000 description 2
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 2
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 2
- NBPZIGIKBFFYOZ-UHFFFAOYSA-N [3-(2-hydroxyethoxy)-3-oxopropyl]-methylphosphinic acid Chemical compound CP(O)(=O)CCC(=O)OCCO NBPZIGIKBFFYOZ-UHFFFAOYSA-N 0.000 description 2
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- PEGCITODQASXKH-UHFFFAOYSA-N [methyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(C)C1=CC=CC=C1 PEGCITODQASXKH-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- YNCDEEFMDXHURQ-UHFFFAOYSA-N aluminum;ethyl 3-oxobutanoate Chemical compound [Al].CCOC(=O)CC(C)=O YNCDEEFMDXHURQ-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 150000002367 halogens Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-N pentane-1-sulfonic acid Chemical compound CCCCCS(O)(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FTFVOGZSTXSQRO-UHFFFAOYSA-N phenyl-(2-phenylphenyl)phosphinic acid Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1P(=O)(O)C1=CC=CC=C1 FTFVOGZSTXSQRO-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ATLPLEZDTSBZQG-UHFFFAOYSA-N propan-2-ylphosphonic acid Chemical compound CC(C)P(O)(O)=O ATLPLEZDTSBZQG-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 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
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
-
- 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
-
- 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
- C08G63/84—Boron, aluminium, gallium, indium, thallium, rare-earth metals, or compounds thereof
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)
Abstract
Description
촉매 | 첨가량 | IV(㎗g-1) | |
실시예 1 | 염화알루미늄페닐포스폰산디메틸 | 0.015몰%0.02몰% | 0.55 |
실시예 2 | 초산알루미늄벤질포스폰산디에틸 | 0.03몰%0.01몰% | 0.57 |
실시예 3 | 수산화염화알루미늄디페닐포스핀산 | 0.05몰%0.07몰% | 0.62 |
실시예 4 | 알루미늄아세틸아세토네이트페닐포스폰산디메틸 | 0.01몰%0.01몰% | 0.6 |
실시예 5 | 수산화알루미늄디페닐포스핀옥사이드 | 0.065몰%0.03몰% | 0.59 |
실시예 6 | 초산알루미늄벤질포스폰산디에틸초산리튬 | 0.01몰%0.005몰%0.025몰% | 0.6 |
실시예 7 | 염화알루미늄페닐포스폰산디메틸초산나트륨 | 0.005몰%0.01몰%0.05몰% | 0.62 |
비교예 1 | 염화알루미늄 | 0.015몰% | 0.31 |
비교예 2 | 페닐포스폰산디메틸 | 0.02몰% | 0.27 |
Claims (9)
- 알루미늄화합물과 인화합물로 된 폴리에스테르 중합촉매.
- 제1항에 있어서, 인화합물이, 포스폰산계 화합물, 포스핀산계 화합물, 포스핀옥사이드계 화합물, 아포스폰산계 화합물, 아포스핀산계 화합물, 포스핀계 화합물로 이루어진 군으로부터 선택되는 1종 또는 2종 이상의 화합물인 폴리에스테르 중합촉매.
- 제1항에 있어서, 인화합물이, 1종 또는 2종 이상의 포스폰산계 화합물인 폴리에스테르 중합촉매.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 인화합물이, 방향환구조를 갖는 화합물인 것을 특징으로 하는 폴리에스테르 중합촉매.
- 제1항에 있어서, 인화합물이, 하기 (식1)~(식3)으로 나타내어지는 화합물로 이루어진 군으로부터 선택되는 1종 또는 2종 이상인 폴리에스테르 중합촉매.(상기 (식1)~(식3) 중, R1, R4, R5, R6은 각각 독립적으로 수소, 탄소수 1~50의 탄화수소기, 수산기 또는 할로겐기 또는 알콕실기 또는 아미노기를 포함하는 탄소수 1~50의 탄화수소기를 나타낸다. R2, R3은 각각 독립적으로 수소, 탄소수 1~10의 탄화수소기를 나타낸다. 단, 탄화수소기는 지환구조나 방향환구조를 포함하고 있더라도 좋다.)
- 제5항에 있어서, R1, R4, R5, R6이 방향환구조를 갖는 기인 폴리에스테르 중합촉매.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 알칼리금속 또는 그들의 화합물 또는 알칼리토류금속 또는 그들의 화합물로 이루어진 군으로부터 선택되는 1종 또는 2종 이상의 금속 및/또는 금속화합물이 공존하는 것을 특징으로 하는 폴리에스테르 중합촉매.
- 제1항 내지 제7항 중 어느 한 항의 촉매를 사용하여 제조된 폴리에스테르.
- 폴리에스테르를 제조할 때에, 제1항 내지 제7항 중 어느 한 항의 촉매를 사용하는 것을 특징으로 하는 폴리에스테르의 제조방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP23748599 | 1999-08-24 | ||
JPJP-P-1999-00237485 | 1999-08-24 |
Publications (2)
Publication Number | Publication Date |
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KR20020030794A true KR20020030794A (ko) | 2002-04-25 |
KR100753265B1 KR100753265B1 (ko) | 2007-08-29 |
Family
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KR1020027002253A KR100753265B1 (ko) | 1999-08-24 | 2000-08-24 | 폴리에스테르 중합촉매 및 이것을 사용하여 제조된폴리에스테르 및 폴리에스테르의 제조방법 |
Country Status (10)
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US (2) | US7208565B1 (ko) |
EP (1) | EP1227117B1 (ko) |
KR (1) | KR100753265B1 (ko) |
CN (1) | CN1233687C (ko) |
AT (1) | ATE283882T1 (ko) |
AU (1) | AU6729800A (ko) |
DE (1) | DE60016447T2 (ko) |
ES (1) | ES2230142T3 (ko) |
MX (1) | MXPA02001863A (ko) |
WO (1) | WO2001014448A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100748290B1 (ko) * | 2001-02-23 | 2007-08-09 | 토요 보세키 가부시기가이샤 | 폴리에스테르 중합촉매 및 이를 사용하여 제조된폴리에스테르 및 폴리에스테르의 제조방법 |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7361680B2 (en) | 1999-07-23 | 2008-04-22 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
JP4288554B2 (ja) * | 2001-03-28 | 2009-07-01 | 東洋紡績株式会社 | ポリエステル組成物およびその製造方法並びにフイルム |
US6953768B2 (en) | 2002-11-26 | 2005-10-11 | Teck Cominco Metals Ltd. | Multi-component catalyst system for the polycondensation manufacture of polyesters |
DE10322099A1 (de) * | 2003-05-15 | 2005-01-27 | Dupont Sabanci Polyester Europe B.V. | Polymerisationskatalysator für die Herstellung von Polyestern, Verfahren zur Herstellung von Polyethylenterephthalat und Verwendung des Polymerisationskatalysators |
TW200602381A (en) * | 2004-02-10 | 2006-01-16 | Toyo Boseki | Polyester polymerization catalyst, polyester produced by using thereof and process for producing polyester |
EP1759834A4 (en) * | 2004-06-17 | 2007-06-06 | Teijin Dupont Films Japan Ltd | LAMINATED FOIL FOR REFLECTION PLATE |
DE102004046771A1 (de) * | 2004-09-24 | 2006-04-06 | Zimmer Ag | Mischung, Polyesterzusammensetzung, Folie sowie Verfahren zu deren Herstellung |
US8557950B2 (en) | 2005-06-16 | 2013-10-15 | Grupo Petrotemex, S.A. De C.V. | High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates |
WO2006137145A1 (ja) * | 2005-06-24 | 2006-12-28 | Toyo Boseki Kabushiki Kaisha | ポリエステルの製造方法およびこれを用いて製造されたポリエステル並びにポリエステル成形体 |
FR2888851A1 (fr) * | 2005-07-25 | 2007-01-26 | Tergal Fibres Sa | Systeme catalytique pour la fabrication de polyester par polycondensation, procede de fabrication de polyester |
US20090082529A1 (en) * | 2005-09-14 | 2009-03-26 | Katsuhiko Kageyama | Polyester, Process for Producing Polyester, and Polyester Molded Article |
US7655746B2 (en) | 2005-09-16 | 2010-02-02 | Eastman Chemical Company | Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers |
US7838596B2 (en) | 2005-09-16 | 2010-11-23 | Eastman Chemical Company | Late addition to effect compositional modifications in condensation polymers |
US7932345B2 (en) | 2005-09-16 | 2011-04-26 | Grupo Petrotemex, S.A. De C.V. | Aluminum containing polyester polymers having low acetaldehyde generation rates |
US9267007B2 (en) | 2005-09-16 | 2016-02-23 | Grupo Petrotemex, S.A. De C.V. | Method for addition of additives into a polymer melt |
US8431202B2 (en) | 2005-09-16 | 2013-04-30 | Grupo Petrotemex, S.A. De C.V. | Aluminum/alkaline or alkali/titanium containing polyesters having improved reheat, color and clarity |
US20080027207A1 (en) * | 2006-07-28 | 2008-01-31 | Jason Christopher Jenkins | Non-precipitating alkali/alkaline earth metal and aluminum compositions made with mono-ol ether solvents |
US7745368B2 (en) | 2006-07-28 | 2010-06-29 | Eastman Chemical Company | Non-precipitating alkali/alkaline earth metal and aluminum compositions made with organic hydroxyacids |
US7709593B2 (en) | 2006-07-28 | 2010-05-04 | Eastman Chemical Company | Multiple feeds of catalyst metals to a polyester production process |
US7709595B2 (en) | 2006-07-28 | 2010-05-04 | Eastman Chemical Company | Non-precipitating alkali/alkaline earth metal and aluminum solutions made with polyhydroxyl ether solvents |
US8563677B2 (en) * | 2006-12-08 | 2013-10-22 | Grupo Petrotemex, S.A. De C.V. | Non-precipitating alkali/alkaline earth metal and aluminum solutions made with diols having at least two primary hydroxyl groups |
US20090186177A1 (en) * | 2008-01-22 | 2009-07-23 | Eastman Chemical Company | Polyester melt phase products and process for making the same |
US8791225B2 (en) * | 2008-06-06 | 2014-07-29 | Dak Americas Mississippi Inc. | Titanium-nitride catalyzed polyester |
KR101515396B1 (ko) * | 2008-12-31 | 2015-04-27 | 에스케이케미칼주식회사 | 폴리에스테르 수지의 제조방법 |
CN101962437B (zh) * | 2009-07-24 | 2013-04-17 | 常州化学研究所 | 用酯化缩聚法合成pet的新型铝催化剂 |
CN102344561B (zh) * | 2010-08-03 | 2015-03-25 | 中国石油化工股份有限公司 | 一种环境友好聚酯缩聚催化剂及利用该催化剂制备聚酯的方法 |
US9475911B2 (en) | 2012-03-29 | 2016-10-25 | Toyobo Co., Ltd. | Polyester composition and polyester film |
KR101995457B1 (ko) | 2012-05-25 | 2019-07-02 | 에스케이케미칼 주식회사 | 폴리에스테르 수지의 제조 방법 |
KR101952941B1 (ko) | 2012-06-05 | 2019-02-27 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 및 이의 제조 방법 |
CN104736573B (zh) * | 2012-11-13 | 2017-02-22 | 日本曹达株式会社 | (甲基)丙烯酸改性聚丁二烯的制造方法 |
CN111527125B (zh) | 2017-12-28 | 2022-07-22 | 帝人株式会社 | 聚(酯)碳酸酯和聚(酯)碳酸酯的制造方法 |
CN113429549B (zh) * | 2021-07-29 | 2023-03-21 | 天津斯坦利新型材料有限公司 | 一种复合催化剂、制备方法以及应用其制备的聚对苯二甲酸亚环己基二亚甲酯 |
Family Cites Families (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1348146A (en) * | 1918-09-03 | 1920-08-03 | Mcquay Norris Mfg Co | Piston-ring |
US3329651A (en) | 1964-08-10 | 1967-07-04 | Monsanto Co | Phenylene antimonate iii polyester catalysts |
US3574174A (en) * | 1965-06-18 | 1971-04-06 | Owens Illinois Inc | Polymerization processes in the presence of catalyst compositions comprising (1) reaction product of a vanadium oxide and organic phosphorus compounds,(2) a hydrocarbyl silane and a halo-aluminum compound |
US3533793A (en) | 1967-03-02 | 1970-10-13 | Eastman Kodak Co | Process for preparing photographic elements |
US3528945A (en) | 1967-08-30 | 1970-09-15 | Fmc Corp | Acetylacetonates as polycondensation catalysts in the direct esterification method of preparing polyesters |
US3528946A (en) | 1967-08-30 | 1970-09-15 | Fmc Corp | Acetylacetonates as polycondensation catalysts in transesterification method of preparing polyesters |
US3594347A (en) | 1968-09-05 | 1971-07-20 | Allied Chem | Polyesters containing aryl phosphinates |
GB1348146A (en) | 1971-05-17 | 1974-03-13 | Ici Ltd | Polyesters |
GB1401771A (en) * | 1971-11-12 | 1975-07-30 | Ici Ltd | Polyesters |
JPS4932676A (ko) | 1972-07-20 | 1974-03-25 | ||
US3953539A (en) * | 1973-03-28 | 1976-04-27 | Teijin Ltd. | Aromatic polyester resin composition having inhibited coloration and method for inhibiting coloration |
US4192775A (en) * | 1975-03-14 | 1980-03-11 | National Petro Chemicals Corporation | Olefin polymerization catalyst |
US4242479A (en) * | 1976-12-23 | 1980-12-30 | Showa Yuka Kabushiki Kaisha | Process for producing an improved ethylenic polymer |
JPS5938973B2 (ja) * | 1977-11-29 | 1984-09-20 | 日東化学工業株式会社 | 含リンポリエステルの製造法 |
JPS55116722A (en) | 1979-03-05 | 1980-09-08 | Toyobo Co Ltd | Preparation of polyester |
US4318799A (en) * | 1980-05-19 | 1982-03-09 | Atlantic Richfield Company | Combination of aluminum and phosphorus passivation process |
JPS57162721A (en) * | 1981-03-31 | 1982-10-06 | Toray Ind Inc | Production of polyester |
US4493903A (en) * | 1981-05-12 | 1985-01-15 | Conoco Inc. | Polymerization process for drag reducing substances |
US4382132A (en) * | 1981-06-01 | 1983-05-03 | El Paso Polyolefins Company | High pressure polyethylene process |
JPS58101021A (ja) * | 1981-12-12 | 1983-06-16 | Toyobo Co Ltd | 2軸延伸ポリエステルフイルム |
JPS6053532A (ja) | 1983-09-01 | 1985-03-27 | Mitsubishi Chem Ind Ltd | 芳香族ポリエステルの製造方法 |
JPS6054326B2 (ja) * | 1984-03-15 | 1985-11-29 | 株式会社クラレ | 酸化チタンを含むポリエステルの製造方法 |
US4565845A (en) | 1984-09-05 | 1986-01-21 | Hitachi Chemical Company, Ltd. | Process for producing polyester and block copolymer thereof |
JPS61101527A (ja) * | 1984-10-24 | 1986-05-20 | Toray Ind Inc | ポリエステルの製造方法 |
US4829113A (en) | 1986-02-25 | 1989-05-09 | Celanese Corporation | Stabilized aromatic polyester compositions |
JPH07121925B2 (ja) * | 1987-04-18 | 1995-12-25 | 三菱化学株式会社 | ラクトン類の製造法 |
JPH0232151A (ja) * | 1988-07-21 | 1990-02-01 | Diafoil Co Ltd | ポリエステル組成物 |
CA2027109C (en) * | 1989-02-10 | 2001-05-01 | Toshiro Nanbu | Thermosetting composition |
US5399607A (en) | 1989-02-10 | 1995-03-21 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | One component composition containing a catalyst and having increased storability |
US4931572A (en) * | 1989-05-17 | 1990-06-05 | Exxon Chemical Patents Inc. | Aromatic carboxylic anhydride catalyst |
USH766H (en) | 1989-05-31 | 1990-04-03 | Hoechst Celanese Corp. | Polyarylate compositions |
US4972036A (en) * | 1989-08-28 | 1990-11-20 | Hi-Tek Polymers, Inc. | Thermosetting acrylic copolymers modified with citric esters |
JP2666502B2 (ja) | 1990-01-18 | 1997-10-22 | 東レ株式会社 | ポリエステルの製造方法 |
JPH03231918A (ja) | 1990-02-07 | 1991-10-15 | Teijin Ltd | ポリエステルの製造法 |
JPH0745357B2 (ja) | 1990-07-03 | 1995-05-17 | 工業技術院長 | 超電導繊維状単結晶およびその製造方法 |
JPH043409A (ja) | 1990-04-20 | 1992-01-08 | Elna Co Ltd | 電解コンデンサ用アルミニウム箔のエッチング方法 |
JP2671568B2 (ja) | 1990-06-19 | 1997-10-29 | 日本電気株式会社 | スイッチング電源回路 |
JP2707807B2 (ja) | 1990-06-19 | 1998-02-04 | 日本電気株式会社 | 圧電トランスdc/dcコンバータ |
US5210155A (en) | 1990-08-24 | 1993-05-11 | Exxon Chemical Patents Inc. | Phenol terminated diester compositions derived from dicarboxylic acids, polyester polymers or alkyd polymers, and curable compositions containing same |
KR940010346B1 (ko) | 1991-06-12 | 1994-10-22 | 한국과학기술연구원 | 폴리부틸렌테레프탈레이트계 중합체의 제조방법 |
JP3200943B2 (ja) | 1992-04-13 | 2001-08-20 | 東レ株式会社 | ポリエステル組成物、製造方法およびポリエステルフィルム |
US5260246A (en) | 1992-09-18 | 1993-11-09 | Industrial Technology Research Institute | Catalyst system for nylon 6 synthesis |
JPH06279579A (ja) | 1993-01-27 | 1994-10-04 | Kanebo Ltd | ポリエステルの製造方法及びポリエステル成形品 |
US5391700A (en) | 1993-04-27 | 1995-02-21 | Nippon Shokubai Co., Ltd. | Process for producing polyester by ring-opening copolymerization |
JP3254309B2 (ja) | 1993-08-17 | 2002-02-04 | 株式会社日本触媒 | 高分子量ポリエステルの製造法 |
US5512635A (en) * | 1993-05-27 | 1996-04-30 | Amoco Corporation | Process for preparing linear monofunctional and telechelic difunctional polymers and compositions obtained thereby |
AU1313395A (en) * | 1993-12-22 | 1995-07-10 | Ciba-Geigy Ag | Process for the stabilization of and stabilizer mixtures for pvdc-containing polyolefin mixtures |
KR100355721B1 (ko) | 1994-02-21 | 2003-01-06 | 이.아이,듀우판드네모아앤드캄파니 | 폴리트리메틸렌테레프탈레이트섬유의염색방법및이렇게염색된섬유의용도 |
DE4430634A1 (de) | 1994-08-29 | 1996-03-07 | Hoechst Ag | Verfahren zur Herstellung thermostabiler, farbneutraler, antimonfreier Polyester und die danach herstellbaren Produkte |
SK284699B6 (sk) | 1994-10-14 | 2005-09-08 | Ciba Specialty Chemicals Holding Inc. | Spôsob zvyšovania molekulovej hmotnosti polykondenzátov |
US5554720A (en) | 1994-12-21 | 1996-09-10 | Eastman Chemical Company | Naphthalenedicarboxylic acid polymers containing aryl thioethers and having reduced fluorescene |
JP3371592B2 (ja) * | 1995-01-19 | 2003-01-27 | ダイソー株式会社 | 乳酸重合体の製造法 |
JP2742892B2 (ja) | 1995-03-03 | 1998-04-22 | 日本コーンスターチ株式会社 | エステル化ポリエステルグラフト化澱粉 |
JP3055001B2 (ja) | 1995-07-14 | 2000-06-19 | 日本コーンスターチ株式会社 | ポリエステルグラフト重合澱粉アロイ |
US5512340A (en) | 1995-06-08 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Catalyst and process for producing polyester |
US5596069A (en) | 1995-06-08 | 1997-01-21 | E. I. Du Pont De Nemours And Company | Catalyst and process for producing catalyst |
US5770682A (en) | 1995-07-25 | 1998-06-23 | Shimadzu Corporation | Method for producing polylactic acid |
JP3517858B2 (ja) | 1995-11-30 | 2004-04-12 | トヨタ自動車株式会社 | ポリ乳酸の製造法 |
JP3517856B2 (ja) | 1995-11-30 | 2004-04-12 | トヨタ自動車株式会社 | ポリ乳酸の製造法 |
JP3517857B2 (ja) | 1995-11-30 | 2004-04-12 | トヨタ自動車株式会社 | ポリ乳酸の製造法 |
KR0174066B1 (ko) | 1995-08-14 | 1999-04-01 | 김상응 | 항균방취 섬유용 폴리에스테르의 제조방법 |
EP0768319A1 (en) * | 1995-09-29 | 1997-04-16 | Nippon Oil Co. Ltd. | Process for the production of polyolefins |
US5847011A (en) | 1995-12-05 | 1998-12-08 | Mitsui Chemicals, Inc. | Degradable copolymer and preparation process thereof |
CN1050621C (zh) | 1995-12-25 | 2000-03-22 | 鞍山钢铁学院 | 一种聚酯薄膜及其制备方法 |
JPH09291141A (ja) | 1996-04-25 | 1997-11-11 | Nippon Ester Co Ltd | ポリエステルの製造方法 |
JPH1036495A (ja) | 1996-07-25 | 1998-02-10 | Nippon Ester Co Ltd | 透明性に優れたポリエステルの連続製造法 |
DE19631068B4 (de) | 1996-08-01 | 2006-06-01 | Zimmer Ag | Verfahren zur Beschleunigung der Polykondensation von Polyester |
EP0826711B1 (en) * | 1996-09-02 | 2003-01-29 | Mitsui Chemicals, Inc. | Preparation process of aliphatic polyester |
DE19638549A1 (de) * | 1996-09-20 | 1998-03-26 | Zimmer Ag | Zeolith-Katalysator zur Polykondensation von Polyester |
US5869582A (en) | 1997-01-22 | 1999-02-09 | Alliedsignal Inc. | Diblock polyester copolymer and process for making |
JP3669803B2 (ja) | 1997-03-10 | 2005-07-13 | 三井化学株式会社 | ポリエステル系樹脂の精製方法 |
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 |
EP0909775B1 (en) | 1997-03-25 | 2003-05-28 | Toray Industries, Inc. | Catalyst for producing polyester, process for producing the same, and process for producing polyester by using the same |
JP3651242B2 (ja) | 1997-03-25 | 2005-05-25 | 東レ株式会社 | 成形加工性に優れたポリエステルおよびその製造方法 |
JP4059360B2 (ja) | 1997-06-04 | 2008-03-12 | 東レ株式会社 | 繊維用ポリエステルの製造方法及びそれに用いる繊維用ポリエステル重合触媒、並びに繊維用ポリエステル重合触媒の製造方法 |
DE59811059D1 (de) * | 1997-06-10 | 2004-04-29 | Acordis Ind Fibers Gmbh | Verfahren zur herstellung von polyestern und copolyestern |
GB9725419D0 (en) | 1997-12-02 | 1998-01-28 | Tioxide Specialties Ltd | Esterification catalysts |
JP3740823B2 (ja) | 1998-02-17 | 2006-02-01 | 東レ株式会社 | ポリエステルの製造方法 |
JP3651228B2 (ja) | 1998-02-18 | 2005-05-25 | 東レ株式会社 | 成形加工性に優れたポリエステルの製造方法 |
US6080303A (en) * | 1998-03-11 | 2000-06-27 | Exxon Chemical Patents, Inc. | Zeolite catalyst activity enhancement by aluminum phosphate and phosphorus |
US6255441B1 (en) * | 1998-04-17 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Titanium-containing catalyst composition and processes therefor and therewith |
US6066714A (en) * | 1998-04-17 | 2000-05-23 | E. I. Du Pont De Nemours And Company | Titanium-containing catalyst composition and processes therefor and therewith |
TWI221861B (en) | 1998-04-22 | 2004-10-11 | Toyo Boseki | Agent for treating metallic surface, surface-treated metal material and coated metal material |
JP2000063504A (ja) | 1998-08-25 | 2000-02-29 | Toray Ind Inc | ポリエステルの製造方法 |
CN1177882C (zh) | 1998-10-23 | 2004-12-01 | 东洋纺织株式会社 | 聚酯的聚合催化剂、聚酯和用于制备聚酯的方法 |
EP1043362A4 (en) * | 1998-10-26 | 2002-05-08 | Toray Industries | POLYESTER COMPOSITION, METHOD FOR THE PRODUCTION THEREOF AND POLYESTER FILM |
JP3753219B2 (ja) | 1999-04-20 | 2006-03-08 | 東洋紡績株式会社 | ポリエステル重合触媒、これを用いて製造されたポリエステルおよびポリエステルの製造方法 |
GB9912210D0 (en) * | 1999-05-25 | 1999-07-28 | Acma Ltd | Esterification catalysts |
JP3758068B2 (ja) | 1999-07-16 | 2006-03-22 | 東洋紡績株式会社 | ポリエステル重合触媒およびこれを用いて製造されたポリエステルならびにポリエステルの製造方法 |
JP3506236B2 (ja) | 1999-08-24 | 2004-03-15 | 東洋紡績株式会社 | ポリエステル重合触媒およびこれを用いて製造されたポリエステルならびにポリエステルの製造方法 |
JP4734699B2 (ja) | 1999-09-29 | 2011-07-27 | 東洋紡績株式会社 | ポリエステル重合触媒およびこれを用いて製造されたポリエステルならびにポリエステルの製造方法 |
DE60023811T2 (de) * | 1999-09-14 | 2006-07-20 | Combi Corp. | Wärmevorrichtung für Feuchttücher und Tuchhebeplatte |
JP3292874B2 (ja) | 1999-11-05 | 2002-06-17 | 独立行政法人産業技術総合研究所 | 高分子量化脂肪族ポリエステル系重合体の製造法 |
AU780389B2 (en) * | 1999-11-11 | 2005-03-17 | Mitsubishi Chemical Corporation | Polyester resin and its production process |
EP1242500B1 (en) | 1999-12-10 | 2005-04-20 | Equipolymers GmbH | Catalyst systems for polycondensation reactions |
TWI235754B (en) | 1999-12-27 | 2005-07-11 | Ind Tech Res Inst | Composition and process for preparing a high molecular weight polyester |
US7199212B2 (en) * | 2000-01-05 | 2007-04-03 | Toyo Boseki Kabushiki Kaisha | Polymerization catalyst for polyesters, polyesters produced with the same and process for producing polyesters |
JP5152608B2 (ja) | 2000-01-26 | 2013-02-27 | 東洋紡株式会社 | ポリエステル重合触媒およびこれを用いて製造されたポリエステル並びにポリエステルの製造方法 |
PT1327648E (pt) * | 2000-09-12 | 2007-08-31 | Toyo Boseki | Catalizador de polimerização para poliéster, poliéster produzido com o catalizador e processo para a produção do poliéster |
TWI288155B (en) | 2001-01-12 | 2007-10-11 | Nanya Plastics Corp | Manufacturing method of copolyester for PET bottles comprising low acetaldehyde content |
CN1328300C (zh) | 2001-02-23 | 2007-07-25 | 东洋纺织株式会社 | 聚酯聚合催化剂、利用其制得的聚酯和聚酯的制造方法 |
TW555780B (en) | 2001-03-19 | 2003-10-01 | Nanya Plastics Corp | Manufacturing method of reducing cyclic oligomer content in polyester |
AU2002345717A1 (en) | 2001-07-02 | 2003-01-21 | Dow Global Technologies Inc. | Procedure for the manufacture of polyalkylene terephthalates |
CN1934216B (zh) | 2004-03-25 | 2011-11-23 | 株式会社丰田中央研究所 | 发光材料及其制造方法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100748290B1 (ko) * | 2001-02-23 | 2007-08-09 | 토요 보세키 가부시기가이샤 | 폴리에스테르 중합촉매 및 이를 사용하여 제조된폴리에스테르 및 폴리에스테르의 제조방법 |
Also Published As
Publication number | Publication date |
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EP1227117A1 (en) | 2002-07-31 |
DE60016447T2 (de) | 2005-12-08 |
CN1233687C (zh) | 2005-12-28 |
US7208565B1 (en) | 2007-04-24 |
ATE283882T1 (de) | 2004-12-15 |
EP1227117A4 (en) | 2002-11-27 |
EP1227117B1 (en) | 2004-12-01 |
US8293862B2 (en) | 2012-10-23 |
KR100753265B1 (ko) | 2007-08-29 |
AU6729800A (en) | 2001-03-19 |
CN1373780A (zh) | 2002-10-09 |
ES2230142T3 (es) | 2005-05-01 |
US20070149757A1 (en) | 2007-06-28 |
MXPA02001863A (es) | 2003-07-14 |
WO2001014448A1 (fr) | 2001-03-01 |
DE60016447D1 (de) | 2005-01-05 |
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