CA2465281A1 - Process for making polytrimethylene terephthalate - Google Patents
Process for making polytrimethylene terephthalate Download PDFInfo
- Publication number
- CA2465281A1 CA2465281A1 CA002465281A CA2465281A CA2465281A1 CA 2465281 A1 CA2465281 A1 CA 2465281A1 CA 002465281 A CA002465281 A CA 002465281A CA 2465281 A CA2465281 A CA 2465281A CA 2465281 A1 CA2465281 A1 CA 2465281A1
- Authority
- CA
- Canada
- Prior art keywords
- precondensation
- product
- solid byproduct
- pdo
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 229920002215 polytrimethylene terephthalate Polymers 0.000 title claims abstract description 37
- -1 polytrimethylene terephthalate Polymers 0.000 title claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 92
- 239000006227 byproduct Substances 0.000 claims abstract description 71
- 239000003054 catalyst Substances 0.000 claims abstract description 52
- 239000000047 product Substances 0.000 claims abstract description 38
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 230000032050 esterification Effects 0.000 claims abstract description 29
- 238000005886 esterification reaction Methods 0.000 claims abstract description 29
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 24
- 239000003085 diluting agent Substances 0.000 claims abstract description 22
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 238000009835 boiling Methods 0.000 claims abstract description 13
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 9
- 230000000737 periodic effect Effects 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 238000004064 recycling Methods 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 42
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 19
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 19
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- 229910052718 tin Inorganic materials 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims 11
- 238000010926 purge Methods 0.000 claims 1
- 230000029087 digestion Effects 0.000 description 30
- 238000004821 distillation Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 16
- 239000010936 titanium Substances 0.000 description 15
- 239000010802 sludge Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 12
- 238000011084 recovery Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- 239000011135 tin Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- ZHVZTRUUPYIJTQ-UHFFFAOYSA-N bis(3-hydroxypropyl) benzene-1,4-dicarboxylate Chemical compound OCCCOC(=O)C1=CC=C(C(=O)OCCCO)C=C1 ZHVZTRUUPYIJTQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010808 liquid waste Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004246 zinc acetate Substances 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/785—Preparation processes characterised by the apparatus 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
- C08G63/02—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
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34100001P | 2001-10-30 | 2001-10-30 | |
| US60/341,000 | 2001-10-30 | ||
| PCT/EP2002/012181 WO2003037958A1 (en) | 2001-10-30 | 2002-10-29 | Process for making polytrimethylene terephthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2465281A1 true CA2465281A1 (en) | 2003-05-08 |
Family
ID=23335843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002465281A Abandoned CA2465281A1 (en) | 2001-10-30 | 2002-10-29 | Process for making polytrimethylene terephthalate |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6657044B1 (https=) |
| EP (1) | EP1456276B1 (https=) |
| JP (1) | JP4074250B2 (https=) |
| KR (1) | KR20050040830A (https=) |
| CN (1) | CN1273514C (https=) |
| AT (1) | ATE403689T1 (https=) |
| BR (1) | BR0213547A (https=) |
| CA (1) | CA2465281A1 (https=) |
| DE (1) | DE60228122D1 (https=) |
| ES (1) | ES2311646T3 (https=) |
| MX (1) | MXPA04004014A (https=) |
| MY (1) | MY129191A (https=) |
| SA (1) | SA03240057B1 (https=) |
| TW (1) | TWI255276B (https=) |
| WO (1) | WO2003037958A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1433439B (zh) * | 2000-02-11 | 2012-08-29 | 纳幕尔杜邦公司 | 用于产生聚(对苯二甲酸丙二醇酯)的连续方法 |
| TWI255821B (en) * | 2003-01-22 | 2006-06-01 | Asahi Kasei Chemicals Corp | Polytrimethylene terephthalate resin and method for production thereof |
| JP4552462B2 (ja) * | 2003-04-07 | 2010-09-29 | 三菱化学株式会社 | ポリエステル重縮合反応留出物の処理方法 |
| US7531617B2 (en) * | 2005-12-21 | 2009-05-12 | E. I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
| US7504474B2 (en) * | 2005-12-21 | 2009-03-17 | E. I. Du Pont De Nemours And Company | Poly(trimethylene therephthalate) continuous manufacturing process |
| US7524921B2 (en) * | 2005-12-21 | 2009-04-28 | E. I. Du Pont De Nemours And Company | Continuous manufacture of poly(trimethylene terephthalate) |
| US7772362B2 (en) * | 2007-07-16 | 2010-08-10 | Texas State University | Treatment method for imparting self-healing and shape memory properties to certain CBDO copolymers |
| US20090043016A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043021A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043017A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US7855244B2 (en) * | 2007-08-06 | 2010-12-21 | E.I. Du Pont De Nemours And Company | Flame retardant polytrimethylene terephthalate composition |
| US20090043019A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| CN102186912A (zh) * | 2008-10-16 | 2011-09-14 | 纳幕尔杜邦公司 | 阻燃剂聚(对苯二甲酸丙二醇酯)组合物 |
| WO2010077937A1 (en) | 2008-12-17 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Reduction of whitening of poly(trimethylene terephthalate) parts by solvent exposure |
| WO2010077905A1 (en) | 2008-12-17 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) polymer blends that have reduced whitening |
| US20100152411A1 (en) | 2008-12-17 | 2010-06-17 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) with reduced whitening |
| JP2012519756A (ja) | 2009-03-03 | 2012-08-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | オリゴマーが低減したポリ（トリメチレンテレフタレート）ペレット及びオリゴマーの低減を測定する方法 |
| EP2643383A1 (en) | 2010-11-22 | 2013-10-02 | E.I. Du Pont De Nemours And Company | Block copolymers comprising poly(1,3-trimethylene terephthalate) and poly(1,3-trimethylene 2,6-naphthalate) |
| KR20160047218A (ko) * | 2014-10-22 | 2016-05-02 | 에스케이케미칼주식회사 | 부산물의 함량이 낮은 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 방법 |
| CN104629021B (zh) * | 2015-02-15 | 2017-07-07 | 张家港美景荣化学工业有限公司 | 一种聚对苯二甲酸丙二醇酯及其生产方法 |
| CN105622907A (zh) * | 2016-04-08 | 2016-06-01 | 张家港美景荣化学工业有限公司 | 高粘聚对苯二甲酸丙二醇酯及其共聚酯的制备方法 |
| KR20180035522A (ko) * | 2016-09-29 | 2018-04-06 | 주식회사 엘지화학 | 폴리에테르에스테르 공중합체의 제조방법 |
| EP3814562A1 (en) | 2018-06-28 | 2021-05-05 | DuPont Industrial Biosciences USA, LLC | Spun yarn comprising polyester staple fibre and fabric comprising the same |
| JP2020050820A (ja) * | 2018-09-28 | 2020-04-02 | 東レ株式会社 | 高収率ポリエステルの製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4424337A (en) | 1982-09-07 | 1984-01-03 | The Goodyear Tire & Rubber Company | Polyisophthalate and copolymers thereof having reduced cyclic dimer content, and a process for making the same |
| US4418188A (en) | 1982-09-07 | 1983-11-29 | The Goodyear Tire & Rubber Company | Polyethylene isophthalate having reduced cyclic dimer content and process therefore |
| US4835247A (en) | 1988-08-08 | 1989-05-30 | The Goodyear Tire & Rubber Company | Process for the synthesis of a copolyester adhesive resin |
| US4921929A (en) | 1988-08-08 | 1990-05-01 | The Goodyear Tire & Rubber Company | Process for the synthesis of a copolyester adhesive resin |
| MY118950A (en) | 1997-04-30 | 2005-02-28 | Shell Int Research | Purification of by- product stream in preparation of polytrimethylene terephthalate |
| US6245879B1 (en) | 1999-01-29 | 2001-06-12 | Shell Oil Company | Purification of 1,3-propanediol in carbonyl-containing stream |
| ES2195465T3 (es) | 1999-04-22 | 2003-12-01 | Zimmer Ag | Procedimiento para producir poli(tereftalato de trimetileno) (ptt). |
| US6277947B1 (en) | 2000-04-21 | 2001-08-21 | Shell Oil Company | Process of producing polytrimethylene terephthalate (PTT) |
| DE60018429T2 (de) * | 1999-08-25 | 2006-04-13 | E.I. Du Pont De Nemours And Co., Wilmington | Herstellung von poly(trimethylenterephthalat) |
| US20020123606A1 (en) * | 1999-08-26 | 2002-09-05 | Kurian Joseph Varapadavil | Poly(trimethylene terephthalate) with low level of DI(1,3-propylene glycol) |
-
2002
- 2002-10-18 US US10/274,317 patent/US6657044B1/en not_active Expired - Fee Related
- 2002-10-29 ES ES02802309T patent/ES2311646T3/es not_active Expired - Lifetime
- 2002-10-29 CA CA002465281A patent/CA2465281A1/en not_active Abandoned
- 2002-10-29 MY MYPI20024047A patent/MY129191A/en unknown
- 2002-10-29 MX MXPA04004014A patent/MXPA04004014A/es active IP Right Grant
- 2002-10-29 TW TW091132056A patent/TWI255276B/zh not_active IP Right Cessation
- 2002-10-29 KR KR1020047006349A patent/KR20050040830A/ko not_active Ceased
- 2002-10-29 CN CNB028215737A patent/CN1273514C/zh not_active Expired - Fee Related
- 2002-10-29 AT AT02802309T patent/ATE403689T1/de not_active IP Right Cessation
- 2002-10-29 JP JP2003540233A patent/JP4074250B2/ja not_active Expired - Fee Related
- 2002-10-29 EP EP02802309A patent/EP1456276B1/en not_active Expired - Lifetime
- 2002-10-29 BR BR0213547-7A patent/BR0213547A/pt not_active IP Right Cessation
- 2002-10-29 WO PCT/EP2002/012181 patent/WO2003037958A1/en not_active Ceased
- 2002-10-29 DE DE60228122T patent/DE60228122D1/de not_active Expired - Fee Related
-
2003
- 2003-03-29 SA SA03240057A patent/SA03240057B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050040830A (ko) | 2005-05-03 |
| CN1273514C (zh) | 2006-09-06 |
| DE60228122D1 (de) | 2008-09-18 |
| EP1456276A1 (en) | 2004-09-15 |
| ATE403689T1 (de) | 2008-08-15 |
| WO2003037958A1 (en) | 2003-05-08 |
| JP2005536574A (ja) | 2005-12-02 |
| TWI255276B (en) | 2006-05-21 |
| SA03240057B1 (ar) | 2007-05-09 |
| MXPA04004014A (es) | 2004-07-23 |
| TW200302839A (en) | 2003-08-16 |
| CN1578800A (zh) | 2005-02-09 |
| BR0213547A (pt) | 2004-10-26 |
| ES2311646T3 (es) | 2009-02-16 |
| EP1456276B1 (en) | 2008-08-06 |
| MY129191A (en) | 2007-03-30 |
| US6657044B1 (en) | 2003-12-02 |
| JP4074250B2 (ja) | 2008-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6657044B1 (en) | Process for making polytrimethylene terephthalate | |
| EP0723951A1 (en) | Process to prepare bis (2-hydroxyethyl) terephthalate | |
| EP0798336B1 (en) | Process for depolymerizing polyesters | |
| US5559159A (en) | Process including depolymerization in polyester reactor for recycling polyester materials | |
| EP1989244B1 (en) | Process for making polybutylene terephthalate (pbt) from polythylene terephthalate(pet) | |
| US20130041053A1 (en) | Process for the Preparation of Polyesters with High Recycle Content | |
| WO2013025186A1 (en) | Process for the preparation of polyesters with high recycle content | |
| US6576774B2 (en) | Process for recycling polytrimethylene terephthalate cyclic dimer | |
| JP2002512279A (ja) | イソソルビドをコモノマーとして含有させたポリエステルおよびそれの製造方法 | |
| JP2008534715A (ja) | 低酸ポリブチレンテレフタレートの調製、および低酸ポリブチレンテレフタレートからの大環状ポリエステルオリゴマーの調製 | |
| US6812321B1 (en) | Method for the continuous production of polybutyleneterephthalate from terephthalic acid and butanediol | |
| US6657040B1 (en) | Method for the continuous production of polybutylene terephthalate from terephthal acid and butane diole | |
| JP7538958B2 (ja) | ビス－２－ヒドロキシエチルテレフタレートの高純度化精製方法およびそれを含むポリエステル樹脂 | |
| JP2006016548A (ja) | ポリエステルの製造方法 | |
| EP3347401B2 (en) | Process for enhancing the molecular weight of a polyester by solid state polymerization | |
| JP3803198B2 (ja) | ポリエステルの製造方法 | |
| JP3782906B2 (ja) | 粗ビス−β−ヒドロキシエチルテレフタレート精製方法 | |
| JP4660108B2 (ja) | ポリエステル製造用難沈殿性微細チタン触媒 | |
| EP0854130A1 (en) | Recovery of monomers from polyethylene naphthalate | |
| JP2000256451A (ja) | ポリエステルの製造方法 | |
| JPH0912696A (ja) | ポリエステルの製造方法 | |
| JP2000256614A (ja) | 粉体塗料用ポリエステル樹脂の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |