KR20080079689A - 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 - Google Patents
폴리(트리메틸렌 테레프탈레이트)의 연속 제조 Download PDFInfo
- Publication number
- KR20080079689A KR20080079689A KR1020087017523A KR20087017523A KR20080079689A KR 20080079689 A KR20080079689 A KR 20080079689A KR 1020087017523 A KR1020087017523 A KR 1020087017523A KR 20087017523 A KR20087017523 A KR 20087017523A KR 20080079689 A KR20080079689 A KR 20080079689A
- Authority
- KR
- South Korea
- Prior art keywords
- propanediol
- trimethylene terephthalate
- condensed
- poly
- byproduct
- 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.)
- Ceased
Links
- 229920002215 polytrimethylene terephthalate Polymers 0.000 title claims abstract description 87
- 238000002360 preparation method Methods 0.000 title description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims abstract description 210
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims abstract description 206
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims abstract description 206
- 239000006227 byproduct Substances 0.000 claims abstract description 200
- 238000000034 method Methods 0.000 claims abstract description 69
- 238000010924 continuous production Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 56
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 41
- 238000005886 esterification reaction Methods 0.000 claims description 37
- 239000007921 spray Substances 0.000 claims description 33
- 238000005809 transesterification reaction Methods 0.000 claims description 32
- 230000032050 esterification Effects 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 238000000746 purification Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 5
- NMYFVWYGKGVPIW-UHFFFAOYSA-N 3,7-dioxabicyclo[7.2.2]trideca-1(11),9,12-triene-2,8-dione Chemical group O=C1OCCCOC(=O)C2=CC=C1C=C2 NMYFVWYGKGVPIW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 description 19
- 238000009833 condensation Methods 0.000 description 15
- 230000005494 condensation Effects 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000012643 polycondensation polymerization Methods 0.000 description 14
- 238000004064 recycling Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical group OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
- 239000012808 vapor phase Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 239000011874 heated mixture Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 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 2
- 239000002994 raw material 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- XWENCHGJOCJZQO-UHFFFAOYSA-N ethane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)C(C(O)=O)C(O)=O XWENCHGJOCJZQO-UHFFFAOYSA-N 0.000 description 1
- RWLDAJMGAVDXSH-UHFFFAOYSA-N ethane-1,1,2-tricarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(O)=O RWLDAJMGAVDXSH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ROTJZTYLACIJIG-UHFFFAOYSA-N pentane-1,3,5-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)CCC(O)=O ROTJZTYLACIJIG-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WQWLQWVLHSPEAR-UHFFFAOYSA-N propane-1,3-diol;terephthalic acid Chemical compound OCCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 WQWLQWVLHSPEAR-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000013022 venting Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 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
- C08G63/78—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
- C08G63/02—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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T29/00—Metal working
- Y10T29/49—Method of mechanical manufacture
- Y10T29/49002—Electrical device making
- Y10T29/49005—Acoustic transducer
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75248105P | 2005-12-21 | 2005-12-21 | |
| US60/752,481 | 2005-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080079689A true KR20080079689A (ko) | 2008-09-01 |
Family
ID=38068904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087017523A Ceased KR20080079689A (ko) | 2005-12-21 | 2006-12-21 | 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7524921B2 (enExample) |
| EP (1) | EP1971629B1 (enExample) |
| JP (1) | JP5152866B2 (enExample) |
| KR (1) | KR20080079689A (enExample) |
| CN (1) | CN101341184B (enExample) |
| AT (1) | ATE499399T1 (enExample) |
| BR (1) | BRPI0621116B8 (enExample) |
| CA (1) | CA2632699A1 (enExample) |
| DE (1) | DE602006020345D1 (enExample) |
| WO (1) | WO2007075991A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5567977B2 (ja) * | 2010-10-21 | 2014-08-06 | 株式会社日立製作所 | ポリトリメチレンテレフタレートの製造装置及び製造方法並びにアクロレイン除去装置 |
| AU2017353995B2 (en) * | 2016-11-03 | 2021-11-11 | The Coca-Cola Company | Acrolein scavenging in PTF and other 1,3-propanediol derived polymers |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927982A (en) * | 1970-03-18 | 1975-12-23 | Du Pont | Recirculating apparatus for continuous esterification reactions |
| US4110316A (en) * | 1977-04-14 | 1978-08-29 | E. I. Du Pont De Nemours And Company | Improved process for preparing poly(ethylene terephthalate) |
| US6245879B1 (en) * | 1999-01-29 | 2001-06-12 | Shell Oil Company | Purification of 1,3-propanediol in carbonyl-containing stream |
| ATE234336T1 (de) * | 1999-04-22 | 2003-03-15 | Zimmer Ag | Verfahren zur herstellung von polytrimethylenterephthalat (ptt) |
| US6277947B1 (en) * | 2000-04-21 | 2001-08-21 | Shell Oil Company | Process of producing polytrimethylene terephthalate (PTT) |
| ATE265486T1 (de) * | 2000-02-11 | 2004-05-15 | Du Pont | Kontinuierliches verfahren zur herstellung von polytrimethylenterephthalat |
| US6353062B1 (en) * | 2000-02-11 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
| US6703478B2 (en) * | 2000-04-27 | 2004-03-09 | Teijin Limited | Polyester continuous production process |
| US6403762B1 (en) * | 2000-08-21 | 2002-06-11 | Shell Oil Company | Solid state polymerization process for poly(trimethylene terephthalate) utilizing a combined crystallization/preheating step |
| JP2002105185A (ja) * | 2000-10-04 | 2002-04-10 | Mitsui Chemicals Inc | ポリエステルの製造方法 |
| US6657044B1 (en) | 2001-10-30 | 2003-12-02 | Shell Oil Company | Process for making polytrimethylene terephthalate |
| US6887953B2 (en) * | 2002-10-11 | 2005-05-03 | E.I. Du Pont De Nemours And Company | Esterification process |
| US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| US7099572B2 (en) * | 2004-06-30 | 2006-08-29 | Synapse, Inc. | Water heating system and method for detecting a dry fire condition for a heating element |
| JP2007009150A (ja) * | 2005-07-04 | 2007-01-18 | Toyobo Co Ltd | ポリエステルの製造方法 |
| 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 |
-
2006
- 2006-12-14 US US11/638,978 patent/US7524921B2/en active Active
- 2006-12-21 AT AT06848012T patent/ATE499399T1/de not_active IP Right Cessation
- 2006-12-21 BR BRPI0621116A patent/BRPI0621116B8/pt not_active IP Right Cessation
- 2006-12-21 EP EP06848012A patent/EP1971629B1/en not_active Not-in-force
- 2006-12-21 JP JP2008547597A patent/JP5152866B2/ja not_active Expired - Fee Related
- 2006-12-21 DE DE602006020345T patent/DE602006020345D1/de active Active
- 2006-12-21 WO PCT/US2006/048980 patent/WO2007075991A2/en not_active Ceased
- 2006-12-21 CA CA002632699A patent/CA2632699A1/en not_active Abandoned
- 2006-12-21 KR KR1020087017523A patent/KR20080079689A/ko not_active Ceased
- 2006-12-21 CN CN2006800484395A patent/CN101341184B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1971629A2 (en) | 2008-09-24 |
| US20070191581A1 (en) | 2007-08-16 |
| JP5152866B2 (ja) | 2013-02-27 |
| EP1971629B1 (en) | 2011-02-23 |
| BRPI0621116A2 (pt) | 2011-11-29 |
| ATE499399T1 (de) | 2011-03-15 |
| DE602006020345D1 (de) | 2011-04-07 |
| CN101341184A (zh) | 2009-01-07 |
| CN101341184B (zh) | 2011-06-15 |
| BRPI0621116B1 (pt) | 2017-12-05 |
| JP2009521577A (ja) | 2009-06-04 |
| US7524921B2 (en) | 2009-04-28 |
| WO2007075991A2 (en) | 2007-07-05 |
| WO2007075991A3 (en) | 2007-08-23 |
| BRPI0621116B8 (pt) | 2017-12-19 |
| CA2632699A1 (en) | 2007-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1259558B1 (en) | Continuous process for producing poly(trimethylene terephthalate) | |
| KR101384445B1 (ko) | 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 방법 | |
| JP4460453B2 (ja) | トリメチレンテレフタレートオリゴマーの調製方法 | |
| KR20080079688A (ko) | 폴리(트리메틸렌 테레프탈레이트) 연속 제조 방법 | |
| KR20080079689A (ko) | 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 | |
| MX2008007926A (es) | Proceso continuo para producir tereftalato de politrimetileno | |
| MX2008007925A (es) | Proceso continuo de fabricacion de tereftalato de politrimetileno |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080718 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20111220 Comment text: Request for Examination of Application |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20130514 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20130805 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20130514 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |