ES2424983T3 - Un nuevo catalizador a base de titanio que muestra actividad y selectividad excelentes en reacciones de policondensación - Google Patents
Un nuevo catalizador a base de titanio que muestra actividad y selectividad excelentes en reacciones de policondensación Download PDFInfo
- Publication number
- ES2424983T3 ES2424983T3 ES09724960T ES09724960T ES2424983T3 ES 2424983 T3 ES2424983 T3 ES 2424983T3 ES 09724960 T ES09724960 T ES 09724960T ES 09724960 T ES09724960 T ES 09724960T ES 2424983 T3 ES2424983 T3 ES 2424983T3
- Authority
- ES
- Spain
- Prior art keywords
- titanium
- catalyst
- solvent
- aryl
- polycondensation
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 68
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229910052719 titanium Inorganic materials 0.000 title claims abstract description 45
- 239000010936 titanium Substances 0.000 title claims abstract description 43
- 238000006068 polycondensation reaction Methods 0.000 title claims abstract description 29
- 230000000694 effects Effects 0.000 title description 5
- -1 methyl- Chemical group 0.000 claims abstract description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000005667 attractant Substances 0.000 claims abstract description 4
- 230000031902 chemoattractant activity Effects 0.000 claims abstract description 4
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000003138 primary alcohols Chemical group 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
- 238000005886 esterification reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
- 230000032050 esterification Effects 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- 229910052787 antimony Inorganic materials 0.000 description 11
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005469 ethylenyl group Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UHPJWJRERDJHOJ-UHFFFAOYSA-N ethene;naphthalene-1-carboxylic acid Chemical group C=C.C1=CC=C2C(C(=O)O)=CC=CC2=C1 UHPJWJRERDJHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7223008P | 2008-03-28 | 2008-03-28 | |
| US72230P | 2008-03-28 | ||
| PCT/IB2009/000574 WO2009118600A2 (en) | 2008-03-28 | 2009-03-23 | A new titanium-based catalyst showing excellent activity and selectivity in polycondensation reactions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2424983T3 true ES2424983T3 (es) | 2013-10-10 |
Family
ID=40677789
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12164529.5T Active ES2531884T3 (es) | 2008-03-28 | 2009-03-23 | Método para producir un poliéster usando un catalizador que contiene atrano |
| ES09724960T Active ES2424983T3 (es) | 2008-03-28 | 2009-03-23 | Un nuevo catalizador a base de titanio que muestra actividad y selectividad excelentes en reacciones de policondensación |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12164529.5T Active ES2531884T3 (es) | 2008-03-28 | 2009-03-23 | Método para producir un poliéster usando un catalizador que contiene atrano |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US20110077379A1 (enExample) |
| EP (2) | EP2479205B1 (enExample) |
| JP (2) | JP5739322B2 (enExample) |
| CN (1) | CN101981083B (enExample) |
| BR (1) | BRPI0907076A2 (enExample) |
| CY (2) | CY1114093T1 (enExample) |
| DK (2) | DK2262846T3 (enExample) |
| ES (2) | ES2531884T3 (enExample) |
| HR (2) | HRP20130735T1 (enExample) |
| HU (1) | HUE024110T2 (enExample) |
| PL (2) | PL2262846T3 (enExample) |
| PT (2) | PT2479205E (enExample) |
| SI (1) | SI2479205T1 (enExample) |
| TW (2) | TWI495659B (enExample) |
| WO (1) | WO2009118600A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875786A (zh) * | 2011-07-12 | 2013-01-16 | 常州化学研究所 | 聚酯制备用多齿配体螯合钛系催化剂的合成方法与应用 |
| EP2725048B1 (de) * | 2012-10-29 | 2016-07-20 | Uhde Inventa-Fischer GmbH | Verfahren zur Herstellung eines hochmolekularen Polyesters oder Copolyesters sowie diese enthaltende Polymerblends |
| FR3054551B1 (fr) * | 2016-07-29 | 2019-08-02 | Roquette Freres | Composition polymere comprenant un polyester thermoplastique |
| CN106866712A (zh) * | 2017-01-11 | 2017-06-20 | 江苏科技大学 | 用于耐高温水性涂料的金属离子交联剂及制备方法 |
| CN114075238B (zh) * | 2020-08-19 | 2023-11-17 | 中国石油化工股份有限公司 | 一种钛酸四丁二醇酯的制备方法 |
| EP4101817A1 (en) | 2021-06-11 | 2022-12-14 | Clariant International Ltd | New titanium catalyst for the polyester manufacturing process |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5946258B2 (ja) | 1976-10-05 | 1984-11-12 | 帝人株式会社 | ポリエステルの製造方法 |
| US4260735A (en) * | 1980-02-12 | 1981-04-07 | Allied Chemical Corporation | Catalytic process for preparation of polyesters |
| DE3300315A1 (de) | 1983-01-07 | 1984-07-12 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von hellfarbigen polyestern unter verwendung von titankatalysatoren |
| ATE159959T1 (de) | 1991-06-03 | 1997-11-15 | Polyplastics Co | Verfahren zur herstellung von polyester, und dessen zusammensetzung |
| IT1271309B (it) * | 1994-12-21 | 1997-05-27 | Enichem Spa | Catalizzatori di policondensazione per la sintesi di polietilene tereftalato |
| TW354305B (en) * | 1994-12-22 | 1999-03-11 | Eastman Chem Co | Production of particular polyesters using a novel catalyst system |
| GB9610939D0 (en) | 1996-05-24 | 1996-07-31 | Ici Plc | Process for preparing a copolyester |
| IT1304797B1 (it) * | 1998-12-23 | 2001-03-29 | Sinco Ricerche Spa | Procedimento per la preparazione di resine poliestere (mg33). |
| JP4806855B2 (ja) * | 2001-03-27 | 2011-11-02 | 東レ株式会社 | ポリブチレンテレフタレートの製造法 |
| US20050009687A1 (en) * | 2003-05-02 | 2005-01-13 | Verkade John G. | Titanium alkoxide catalysts for polymerization of cyclic esters and methods of polymerization |
| US20050215425A1 (en) | 2004-03-26 | 2005-09-29 | Clair Jerry D S | Esterification catalyst and process therewith |
-
2009
- 2009-03-23 PL PL09724960T patent/PL2262846T3/pl unknown
- 2009-03-23 CN CN200980111155XA patent/CN101981083B/zh not_active Expired - Fee Related
- 2009-03-23 SI SI200931143T patent/SI2479205T1/sl unknown
- 2009-03-23 PT PT12164529T patent/PT2479205E/pt unknown
- 2009-03-23 DK DK09724960.1T patent/DK2262846T3/da active
- 2009-03-23 DK DK12164529T patent/DK2479205T3/en active
- 2009-03-23 PT PT97249601T patent/PT2262846E/pt unknown
- 2009-03-23 EP EP20120164529 patent/EP2479205B1/en not_active Not-in-force
- 2009-03-23 WO PCT/IB2009/000574 patent/WO2009118600A2/en not_active Ceased
- 2009-03-23 PL PL12164529T patent/PL2479205T3/pl unknown
- 2009-03-23 ES ES12164529.5T patent/ES2531884T3/es active Active
- 2009-03-23 JP JP2011501310A patent/JP5739322B2/ja not_active Expired - Fee Related
- 2009-03-23 US US12/933,950 patent/US20110077379A1/en not_active Abandoned
- 2009-03-23 HU HUE12164529A patent/HUE024110T2/en unknown
- 2009-03-23 ES ES09724960T patent/ES2424983T3/es active Active
- 2009-03-23 EP EP09724960.1A patent/EP2262846B9/en not_active Not-in-force
- 2009-03-23 HR HRP20130735AT patent/HRP20130735T1/hr unknown
- 2009-03-23 BR BRPI0907076A patent/BRPI0907076A2/pt not_active IP Right Cessation
- 2009-03-27 TW TW102147503A patent/TWI495659B/zh not_active IP Right Cessation
- 2009-03-27 TW TW098110181A patent/TWI487728B/zh not_active IP Right Cessation
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2012
- 2012-08-23 US US13/592,924 patent/US8440782B2/en not_active Expired - Fee Related
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2013
- 2013-06-26 JP JP2013134332A patent/JP5739481B2/ja not_active Expired - Fee Related
- 2013-07-01 CY CY20131100528T patent/CY1114093T1/el unknown
- 2013-07-26 US US13/952,438 patent/US20140024798A1/en not_active Abandoned
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2015
- 2015-01-15 HR HRP20150054AT patent/HRP20150054T1/hr unknown
- 2015-03-12 CY CY20151100247T patent/CY1117278T1/el unknown
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