KR101384445B1 - 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 방법 - Google Patents
폴리(트리메틸렌 테레프탈레이트)의 연속 제조 방법 Download PDFInfo
- Publication number
- KR101384445B1 KR101384445B1 KR1020087017521A KR20087017521A KR101384445B1 KR 101384445 B1 KR101384445 B1 KR 101384445B1 KR 1020087017521 A KR1020087017521 A KR 1020087017521A KR 20087017521 A KR20087017521 A KR 20087017521A KR 101384445 B1 KR101384445 B1 KR 101384445B1
- Authority
- KR
- South Korea
- Prior art keywords
- propanediol
- condensed
- trimethylene terephthalate
- poly
- product
- 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.)
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- 229920002215 polytrimethylene terephthalate Polymers 0.000 title claims abstract description 65
- 238000010924 continuous production Methods 0.000 title abstract description 12
- -1 poly(trimethylene terephthalate) Polymers 0.000 title description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims abstract description 164
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims abstract description 160
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims abstract description 160
- 239000006227 byproduct Substances 0.000 claims abstract description 142
- 238000000034 method Methods 0.000 claims abstract description 71
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 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
- 238000005886 esterification reaction Methods 0.000 claims description 41
- 238000005809 transesterification reaction Methods 0.000 claims description 37
- 239000007787 solid Substances 0.000 claims description 31
- 230000032050 esterification Effects 0.000 claims description 26
- 239000007921 spray Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000012643 polycondensation polymerization Methods 0.000 description 16
- 238000001556 precipitation Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 238000004064 recycling Methods 0.000 description 14
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000746 purification Methods 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 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
- 239000000047 product Substances 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
- 125000004122 cyclic group Chemical group 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
- 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
- 238000001816 cooling Methods 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000008901 benefit Effects 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
- 150000002009 diols Chemical class 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
- 238000002156 mixing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 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
- 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
- NMYFVWYGKGVPIW-UHFFFAOYSA-N 3,7-dioxabicyclo[7.2.2]trideca-1(11),9,12-triene-2,8-dione Chemical compound O=C1OCCCOC(=O)C2=CC=C1C=C2 NMYFVWYGKGVPIW-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
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002148 esters 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
- 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
- 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 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
- 238000005086 pumping Methods 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
- 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
- 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/22—Testing for sterility conditions
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/569—Immunoassay; Biospecific binding assay; Materials therefor for microorganisms, e.g. protozoa, bacteria, viruses
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Urology & Nephrology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Cell Biology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75247905P | 2005-12-21 | 2005-12-21 | |
| US60/752,479 | 2005-12-21 | ||
| PCT/US2006/048585 WO2007075774A2 (en) | 2005-12-21 | 2006-12-20 | Continuous process for producing poly(trimethylene terephthalate) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20080079687A KR20080079687A (ko) | 2008-09-01 |
| KR101384445B1 true KR101384445B1 (ko) | 2014-04-11 |
Family
ID=38123861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087017521A Active KR101384445B1 (ko) | 2005-12-21 | 2006-12-20 | 폴리(트리메틸렌 테레프탈레이트)의 연속 제조 방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7531617B2 (enExample) |
| EP (1) | EP1976999B1 (enExample) |
| JP (1) | JP5608326B2 (enExample) |
| KR (1) | KR101384445B1 (enExample) |
| CN (1) | CN101636428B (enExample) |
| BR (1) | BRPI0621118B1 (enExample) |
| CA (1) | CA2632573A1 (enExample) |
| DK (1) | DK1976999T3 (enExample) |
| ES (1) | ES2557327T3 (enExample) |
| WO (1) | WO2007075774A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524921B2 (en) * | 2005-12-21 | 2009-04-28 | E. I. Du Pont De Nemours And Company | Continuous manufacture of poly(trimethylene terephthalate) |
| 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 |
| US20090043016A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043019A1 (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 |
| JP2012505953A (ja) * | 2008-10-16 | 2012-03-08 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 難燃性ポリ（トリメチレンテレフタレート）組成物 |
| BRPI1006518A2 (pt) * | 2009-03-03 | 2016-02-10 | Du Pont | processo para a redução de teor de oligômero de péletes de polímero de poli (trimetileno tereftalato), processo para medir da redução de teor de oligômero de polímero de poli(trimetileno tereftalato), péletes, artigo produzido por péletes moldados e fibra produzida por péletes de fiação derretida |
| US8389604B2 (en) * | 2009-11-02 | 2013-03-05 | E I Du Pont De Nemours And Company | Method for providing toughened poly(trimethylene terephthalate) molding resins |
| US20110105644A1 (en) * | 2009-11-02 | 2011-05-05 | E. I. Du Pont De Nemours And Company | Toughened poly(trimethylene terephthalate) molding resins and molded articles therefrom |
| KR102191438B1 (ko) * | 2014-08-26 | 2020-12-15 | 에스케이케미칼 주식회사 | 부산물의 함량이 낮은 폴리(트리메틸렌 테레프탈레이트)의 제조 방법 |
| CN112639183A (zh) | 2018-06-28 | 2021-04-09 | 杜邦工业生物科学美国有限责任公司 | 包含聚酯短纤维的纺纱以及包含所述纺纱的织物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002105185A (ja) * | 2000-10-04 | 2002-04-10 | Mitsui Chemicals Inc | ポリエステルの製造方法 |
Family Cites Families (14)
| 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) |
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2006
- 2006-12-14 US US11/638,919 patent/US7531617B2/en active Active
- 2006-12-20 KR KR1020087017521A patent/KR101384445B1/ko active Active
- 2006-12-20 BR BRPI0621118-6A patent/BRPI0621118B1/pt not_active IP Right Cessation
- 2006-12-20 EP EP06848971.5A patent/EP1976999B1/en active Active
- 2006-12-20 DK DK06848971.5T patent/DK1976999T3/en active
- 2006-12-20 ES ES06848971.5T patent/ES2557327T3/es active Active
- 2006-12-20 CN CN2006800484696A patent/CN101636428B/zh active Active
- 2006-12-20 JP JP2008547484A patent/JP5608326B2/ja not_active Expired - Fee Related
- 2006-12-20 CA CA002632573A patent/CA2632573A1/en not_active Abandoned
- 2006-12-20 WO PCT/US2006/048585 patent/WO2007075774A2/en not_active Ceased
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|---|---|---|---|---|
| JP2002105185A (ja) * | 2000-10-04 | 2002-04-10 | Mitsui Chemicals Inc | ポリエステルの製造方法 |
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|---|---|
| DK1976999T3 (en) | 2016-02-01 |
| WO2007075774A2 (en) | 2007-07-05 |
| CN101636428A (zh) | 2010-01-27 |
| CN101636428B (zh) | 2012-03-14 |
| BRPI0621118B1 (pt) | 2018-01-30 |
| JP2009521567A (ja) | 2009-06-04 |
| WO2007075774A3 (en) | 2009-09-03 |
| US7531617B2 (en) | 2009-05-12 |
| EP1976999A2 (en) | 2008-10-08 |
| ES2557327T3 (es) | 2016-01-25 |
| BRPI0621118A2 (pt) | 2011-11-29 |
| KR20080079687A (ko) | 2008-09-01 |
| JP5608326B2 (ja) | 2014-10-15 |
| CA2632573A1 (en) | 2007-07-05 |
| EP1976999B1 (en) | 2015-10-28 |
| US20070191580A1 (en) | 2007-08-16 |
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