DE60017264T3 - Copolyester mit reaktorqualität für den einsatz in schrumpffolien - Google Patents
Copolyester mit reaktorqualität für den einsatz in schrumpffolien Download PDFInfo
- Publication number
- DE60017264T3 DE60017264T3 DE60017264T DE60017264T DE60017264T3 DE 60017264 T3 DE60017264 T3 DE 60017264T3 DE 60017264 T DE60017264 T DE 60017264T DE 60017264 T DE60017264 T DE 60017264T DE 60017264 T3 DE60017264 T3 DE 60017264T3
- Authority
- DE
- Germany
- Prior art keywords
- mole percent
- copolyester
- residues
- rxn
- ppm
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920001634 Copolyester Polymers 0.000 title claims description 157
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 188
- 239000000203 mixture Substances 0.000 claims description 122
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 57
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 48
- 150000002009 diols Chemical class 0.000 claims description 42
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 38
- 229920006300 shrink film Polymers 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000004056 anthraquinones Chemical class 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 238000003490 calendering Methods 0.000 claims description 2
- 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 claims 2
- 239000004800 polyvinyl chloride Substances 0.000 description 26
- 229920000915 polyvinyl chloride Polymers 0.000 description 25
- 239000000463 material Substances 0.000 description 20
- 229920000139 polyethylene terephthalate Polymers 0.000 description 19
- 239000005020 polyethylene terephthalate Substances 0.000 description 18
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 18
- 238000001035 drying Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229920006257 Heat-shrinkable film Polymers 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 239000008188 pellet Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 3
- -1 phosphate ester Chemical class 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 2
- VGWDZDOVIHVYBQ-UHFFFAOYSA-N (2-hydroxyphenyl)methyl 2-hydroxybenzoate;manganese Chemical compound [Mn].OC1=CC=CC=C1COC(=O)C1=CC=CC=C1O VGWDZDOVIHVYBQ-UHFFFAOYSA-N 0.000 description 1
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- IUYYVMKHUXDWEU-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,1-diol Chemical compound CC(C)CC(C)(C)C(O)O IUYYVMKHUXDWEU-UHFFFAOYSA-N 0.000 description 1
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 description 1
- ICPXIRMAMWRMAD-UHFFFAOYSA-N 2-[3-[2-[3-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=CC(OCCO)=CC=1C(C)(C)C1=CC=CC(OCCO)=C1 ICPXIRMAMWRMAD-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
- FQCHNZLQGCBANT-UHFFFAOYSA-L 2-hydroxyacetate;manganese(2+) Chemical compound [Mn+2].OCC([O-])=O.OCC([O-])=O FQCHNZLQGCBANT-UHFFFAOYSA-L 0.000 description 1
- ACOQOLIJGGKILA-UHFFFAOYSA-N 2-methylpentane-1,1-diol Chemical compound CCCC(C)C(O)O ACOQOLIJGGKILA-UHFFFAOYSA-N 0.000 description 1
- CPHURRLSZSRQFS-UHFFFAOYSA-N 3-[4-[2-[4-(3-hydroxypropoxy)phenyl]propan-2-yl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)(C)C1=CC=C(OCCCO)C=C1 CPHURRLSZSRQFS-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- UNRVMLDKEXPNDG-UHFFFAOYSA-N butanedioic acid;manganese Chemical compound [Mn].OC(=O)CCC(O)=O UNRVMLDKEXPNDG-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002696 manganese Chemical class 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
- YIHQSMBNBPAEJC-UHFFFAOYSA-L manganese(2+);dibenzoate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YIHQSMBNBPAEJC-UHFFFAOYSA-L 0.000 description 1
- KEGIEOGUARJXQU-UHFFFAOYSA-L manganese(2+);naphthalene-1-carboxylate Chemical compound [Mn+2].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 KEGIEOGUARJXQU-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003278 mimic effect Effects 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
- 238000004806 packaging method and process Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002784 stomach Anatomy 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
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
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
- C08G63/66—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
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14929899P | 1999-08-17 | 1999-08-17 | |
| US149298P | 1999-08-17 | ||
| US636320 | 2000-08-11 | ||
| US09/636,320 US6362306B1 (en) | 1999-08-17 | 2000-08-11 | Reactor grade copolyesters for shrink film applications |
| EP00957443A EP1204694B2 (en) | 1999-08-17 | 2000-08-15 | Reactor grade copolyesters for shrink film applications |
| PCT/US2000/022296 WO2001012697A1 (en) | 1999-08-17 | 2000-08-15 | Reactor grade copolyesters for shrink film applications |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE60017264D1 DE60017264D1 (de) | 2005-02-10 |
| DE60017264T2 DE60017264T2 (de) | 2005-06-23 |
| DE60017264T3 true DE60017264T3 (de) | 2012-02-09 |
Family
ID=26846614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60017264T Expired - Lifetime DE60017264T3 (de) | 1999-08-17 | 2000-08-15 | Copolyester mit reaktorqualität für den einsatz in schrumpffolien |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6362306B1 (https=) |
| EP (1) | EP1204694B2 (https=) |
| JP (2) | JP2003531214A (https=) |
| CN (1) | CN1210327C (https=) |
| BR (1) | BR0013359A (https=) |
| DE (1) | DE60017264T3 (https=) |
| MX (1) | MXPA02001410A (https=) |
| WO (1) | WO2001012697A1 (https=) |
Families Citing this family (37)
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| KR100593971B1 (ko) * | 2004-06-18 | 2006-06-30 | 에스케이씨 주식회사 | 내충격성 열수축성 폴리에스터 필름 |
| KR101293098B1 (ko) * | 2004-08-30 | 2013-08-12 | 미쓰비시 가가꾸 폴리에스테르 필름 가부시키가이샤 | 이형용 폴리에스테르 필름 |
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| KR101190348B1 (ko) * | 2007-12-11 | 2012-10-11 | 코오롱인더스트리 주식회사 | 열수축성 폴리에스테르계 필름 |
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| WO2011068195A1 (ja) * | 2009-12-04 | 2011-06-09 | 株式会社クラレ | 常圧可染ポリエステル繊維及びその製造方法 |
| WO2013056011A1 (en) * | 2011-10-14 | 2013-04-18 | Avery Dennison Corporation | Shrink film for label |
| US9427945B2 (en) * | 2011-12-30 | 2016-08-30 | Liberman Distributing And Manufacturing Co. | Extendable self-supporting material composites and manufacture thereof |
| EP2802453A1 (en) | 2012-01-11 | 2014-11-19 | Avery Dennison Corporation | Multi-layered shrink film with polyolefin core |
| US10329393B2 (en) | 2012-12-12 | 2019-06-25 | Eastman Chemical Company | Copolysters plasticized with polymeric plasticizer for shrink film applications |
| KR102082304B1 (ko) | 2013-05-02 | 2020-02-27 | 에스케이케미칼 주식회사 | 공중합 폴리에스테르 수지 및 이를 이용한 성형제품 |
| CN105670233B (zh) * | 2014-11-18 | 2019-05-21 | 东丽纤维研究所(中国)有限公司 | 一种聚酯组合物及其制备方法和用途 |
| KR101767132B1 (ko) * | 2016-03-02 | 2017-08-14 | 주식회사 휴비스 | 공중합 폴리에스테르 수지 제조용 화합물 및 이를 이용한 공중합 폴리에스테르 수지의 제조방법 |
| US11427688B2 (en) | 2017-04-17 | 2022-08-30 | Eastman Chemical Company | Copolyesters plasticized with polymeric plasticizer |
| US10543656B2 (en) | 2018-01-11 | 2020-01-28 | Eastman Chemical Company | Tough shrinkable films |
| KR102240877B1 (ko) | 2018-04-30 | 2021-04-19 | 에스케이씨 주식회사 | 폴리에스테르 용기의 재생 방법 및 이로부터 제조된 재생 폴리에스테르 칩 |
| KR102153670B1 (ko) | 2018-05-21 | 2020-09-08 | 에스케이씨 주식회사 | 열수축성 필름 및 이의 제조방법 |
| US12116452B2 (en) | 2018-10-08 | 2024-10-15 | Eastman Chemical Company | Crystallizable shrinkable films and thermoformable sheets made from resins blends |
| CN113260652A (zh) * | 2018-12-17 | 2021-08-13 | 伊士曼化工公司 | 含有低二乙二醇的来自对苯二甲酸的共聚酯 |
| US20220250362A1 (en) * | 2019-08-02 | 2022-08-11 | Eastman Chemical Company | Multilayer sheet |
| KR102772283B1 (ko) * | 2019-09-27 | 2025-02-21 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 혼합물, 폴리에스테르 필름 및 이의 제조 방법 |
| CN114787233B (zh) | 2019-10-08 | 2024-08-27 | 伊士曼化工公司 | 用于具有回收料含量的可结晶反应器级树脂的催化剂体系 |
| US20220348715A1 (en) * | 2019-10-25 | 2022-11-03 | Eastman Chemical Company | Copolyesters produced from recycled copolyesters |
| CN110982052A (zh) * | 2019-12-31 | 2020-04-10 | 上海慧翌新材料科技有限公司 | 一种波斯纶用钛基聚酯及其制备方法 |
| CN114316523A (zh) * | 2020-09-30 | 2022-04-12 | 美国克罗克纳潘塔普拉斯特有限公司 | 热收缩膜及其制造方法 |
| CN113334607B (zh) * | 2021-06-09 | 2023-08-29 | 海德里希(厦门)真空机械制造有限公司 | 一种风电叶片生产用多组分混料装置及其控制方法 |
| KR102553960B1 (ko) | 2021-07-05 | 2023-07-11 | 에스케이마이크로웍스 주식회사 | 폴리에스테르 필름, 이를 포함하는 열수축성 라벨 및 포장재 |
| WO2023182803A1 (ko) * | 2022-03-23 | 2023-09-28 | 에스케이케미칼 주식회사 | 열 수축 라벨용 폴리에스테르 공중합체, 이를 포함하는 조성물 및 이를 포함하는 제품 |
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-
2000
- 2000-08-11 US US09/636,320 patent/US6362306B1/en not_active Expired - Lifetime
- 2000-08-15 DE DE60017264T patent/DE60017264T3/de not_active Expired - Lifetime
- 2000-08-15 BR BR0013359-0A patent/BR0013359A/pt not_active Application Discontinuation
- 2000-08-15 EP EP00957443A patent/EP1204694B2/en not_active Expired - Lifetime
- 2000-08-15 WO PCT/US2000/022296 patent/WO2001012697A1/en not_active Ceased
- 2000-08-15 JP JP2001517588A patent/JP2003531214A/ja not_active Withdrawn
- 2000-08-15 CN CN00814093.6A patent/CN1210327C/zh not_active Expired - Lifetime
- 2000-08-15 MX MXPA02001410A patent/MXPA02001410A/es active IP Right Grant
-
2012
- 2012-08-10 JP JP2012178189A patent/JP2012211346A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1399656A (zh) | 2003-02-26 |
| CN1210327C (zh) | 2005-07-13 |
| WO2001012697A1 (en) | 2001-02-22 |
| WO2001012697A8 (en) | 2001-10-25 |
| DE60017264D1 (de) | 2005-02-10 |
| EP1204694B2 (en) | 2011-05-25 |
| MXPA02001410A (es) | 2002-07-30 |
| DE60017264T2 (de) | 2005-06-23 |
| BR0013359A (pt) | 2002-04-30 |
| JP2003531214A (ja) | 2003-10-21 |
| EP1204694A1 (en) | 2002-05-15 |
| US6362306B1 (en) | 2002-03-26 |
| EP1204694B1 (en) | 2005-01-05 |
| JP2012211346A (ja) | 2012-11-01 |
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| 8363 | Opposition against the patent | ||
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Representative=s name: LEDERER & KELLER, 80538 MUENCHEN |