BRPI0809807B1 - "catalisador de polimerização, processo para homopolimerização ou copolimerização de um ôxido de alquileno e uso do catalisador de polimerização" - Google Patents
"catalisador de polimerização, processo para homopolimerização ou copolimerização de um ôxido de alquileno e uso do catalisador de polimerização" Download PDFInfo
- Publication number
- BRPI0809807B1 BRPI0809807B1 BRPI0809807-7A BRPI0809807A BRPI0809807B1 BR PI0809807 B1 BRPI0809807 B1 BR PI0809807B1 BR PI0809807 A BRPI0809807 A BR PI0809807A BR PI0809807 B1 BRPI0809807 B1 BR PI0809807B1
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- Brazil
- Prior art keywords
- group
- hydrogen
- carbon atoms
- catalyst
- independently
- Prior art date
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- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- 241001417527 Pempheridae Species 0.000 description 1
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- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
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- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical compound [AlH3].[AlH3] VRAIHTAYLFXSJJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 1
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- QYRVKEFNJZPMKU-UHFFFAOYSA-N diethyl(propan-2-yloxy)alumane Chemical compound CC(C)[O-].CC[Al+]CC QYRVKEFNJZPMKU-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical group CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003622 immobilized catalyst Substances 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000013365 molecular weight analysis method Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- WUWFGTDHBCXCAS-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]hept-1(6)-en-5-yl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1CCCC2=C1O2 WUWFGTDHBCXCAS-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- RRFDPGUAFDYXLS-UHFFFAOYSA-N tris(2-cyclohexylethyl)alumane Chemical compound C1CCCCC1CC[Al](CCC1CCCCC1)CCC1CCCCC1 RRFDPGUAFDYXLS-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2654—Aluminium or boron; Compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92626907P | 2007-04-26 | 2007-04-26 | |
| US60/926,269 | 2007-04-26 | ||
| PCT/US2008/055281 WO2008134118A1 (en) | 2007-04-26 | 2008-02-28 | Highly active catalysts for alkylene oxide polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0809807A2 BRPI0809807A2 (pt) | 2014-10-07 |
| BRPI0809807B1 true BRPI0809807B1 (pt) | 2018-03-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0809807-7A BRPI0809807B1 (pt) | 2007-04-26 | 2008-02-28 | "catalisador de polimerização, processo para homopolimerização ou copolimerização de um ôxido de alquileno e uso do catalisador de polimerização" |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8273678B2 (enExample) |
| EP (1) | EP2152778B1 (enExample) |
| JP (1) | JP5302298B2 (enExample) |
| CN (1) | CN101668788B (enExample) |
| AT (1) | ATE482247T1 (enExample) |
| BR (1) | BRPI0809807B1 (enExample) |
| DE (1) | DE602008002755D1 (enExample) |
| WO (1) | WO2008134118A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009029050A1 (de) * | 2009-08-31 | 2011-03-03 | Evonik Oxeno Gmbh | Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen |
| WO2013116027A1 (en) * | 2012-01-30 | 2013-08-08 | Dow Global Technologies Llc | Process for preparing high molecular weight polymers by polymerizing epoxide monomers |
| JP6786811B2 (ja) * | 2016-02-10 | 2020-11-18 | 東ソー株式会社 | 有機塩基化合物、ルイス酸及び活性水素含有化合物を含む組成物 |
| GB201717441D0 (en) * | 2017-10-24 | 2017-12-06 | Econic Tech Ltd | A polymerisation process |
| CN109096481B (zh) * | 2018-08-28 | 2020-06-19 | 浙江大学 | 一种用于制备含聚醚的聚合物的催化体系及多种含聚醚的聚合物的制备方法 |
| CN114315883B (zh) * | 2022-01-17 | 2023-10-20 | 万华化学集团股份有限公司 | 二苯并呋喃酚ivb族金属配合物及其制备方法、催化剂体系和烯烃聚合的方法 |
| CN117887062B (zh) * | 2024-03-15 | 2024-06-18 | 中国科学院过程工程研究所 | 一种可控合成低分子量窄分布聚醚多元醇的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB867452A (en) | 1958-12-12 | 1961-05-10 | Petrochemicals Ltd | Improvements in and relating to the production of alkylene oxide polymers |
| NL280229A (enExample) | 1961-06-29 | |||
| GB1032033A (en) * | 1962-06-14 | 1966-06-08 | Dunlop Rubber Co | Improvements in and relating to catalysts |
| US3457186A (en) | 1964-09-30 | 1969-07-22 | Columbian Carbon | Homogeneous iron coordination catalysts |
| DE1795466A1 (de) * | 1964-09-30 | 1970-09-17 | Columbian Carbon | Verfahren zur Herstellung von Polymerisaten |
| FR1583736A (enExample) | 1967-11-21 | 1969-12-05 | ||
| JP2575230B2 (ja) * | 1990-10-08 | 1997-01-22 | 株式会社トクヤマ | ポリエーテルの製造方法 |
| ES2174254T3 (es) * | 1996-05-02 | 2002-11-01 | Sod Conseils Rech Applic | Nuevos compuestos que poseen un elemento del grupo 13 unido a un ligando tridentado mono- o di-anionico, su procedimiento de preparacion y su aplicacion como catalizadores de polimerizacion. |
| WO2002098559A2 (en) * | 2001-05-31 | 2002-12-12 | Union Carbide Chemicals & Plastics Technology Cor Poration | Organoaluminum catalyst, its preparation and its use in a process for the polymerization of alkylene oxides |
| US7456127B2 (en) | 2002-03-06 | 2008-11-25 | Union Carbide Chemicals And Plastics Technology Corporation | Organoaluminum catalyst |
| GB0228888D0 (en) * | 2002-12-11 | 2003-01-15 | Johnson Matthey Plc | Polymerisation reaction and catalyst therefor |
| US20100190955A1 (en) * | 2006-10-13 | 2010-07-29 | Dow Global Technologies Inc. | Poly(oxirane)s and processes and catalysts for making them |
-
2008
- 2008-02-28 JP JP2010506351A patent/JP5302298B2/ja not_active Expired - Fee Related
- 2008-02-28 US US12/597,623 patent/US8273678B2/en not_active Expired - Fee Related
- 2008-02-28 EP EP08730956A patent/EP2152778B1/en not_active Not-in-force
- 2008-02-28 CN CN2008800132450A patent/CN101668788B/zh not_active Expired - Fee Related
- 2008-02-28 DE DE602008002755T patent/DE602008002755D1/de active Active
- 2008-02-28 AT AT08730956T patent/ATE482247T1/de not_active IP Right Cessation
- 2008-02-28 BR BRPI0809807-7A patent/BRPI0809807B1/pt not_active IP Right Cessation
- 2008-02-28 WO PCT/US2008/055281 patent/WO2008134118A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP5302298B2 (ja) | 2013-10-02 |
| WO2008134118A1 (en) | 2008-11-06 |
| US8273678B2 (en) | 2012-09-25 |
| CN101668788B (zh) | 2011-11-30 |
| DE602008002755D1 (de) | 2010-11-04 |
| BRPI0809807A2 (pt) | 2014-10-07 |
| JP2010525147A (ja) | 2010-07-22 |
| EP2152778A1 (en) | 2010-02-17 |
| EP2152778B1 (en) | 2010-09-22 |
| CN101668788A (zh) | 2010-03-10 |
| US20100197873A1 (en) | 2010-08-05 |
| ATE482247T1 (de) | 2010-10-15 |
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