CA2434864C - Activated starter mixtures and the processes related thereto - Google Patents
Activated starter mixtures and the processes related thereto Download PDFInfo
- Publication number
- CA2434864C CA2434864C CA2434864A CA2434864A CA2434864C CA 2434864 C CA2434864 C CA 2434864C CA 2434864 A CA2434864 A CA 2434864A CA 2434864 A CA2434864 A CA 2434864A CA 2434864 C CA2434864 C CA 2434864C
- Authority
- CA
- Canada
- Prior art keywords
- starter compound
- starter
- mixture
- glycol
- activated
- 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.)
- Expired - Fee Related
Links
- 239000007858 starting material Substances 0.000 title claims abstract description 152
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 229920005862 polyol Polymers 0.000 claims abstract description 57
- 150000003077 polyols Chemical class 0.000 claims abstract description 57
- 238000010923 batch production Methods 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims description 51
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- -1 polyoxypropylene Polymers 0.000 claims description 22
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 18
- 235000011187 glycerol Nutrition 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 229920001451 polypropylene glycol Polymers 0.000 claims description 10
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 4
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 abstract description 8
- 238000006116 polymerization reaction Methods 0.000 abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- 239000004594 Masterbatch (MB) Substances 0.000 description 19
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 15
- 150000002924 oxiranes Chemical class 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 230000000536 complexating effect Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 230000004913 activation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004808 allyl alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229920005628 alkoxylated polyol Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- 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
- C08G65/2696—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 process or apparatus used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
-
- 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
- C08G65/2603—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 the other compounds containing oxygen
- C08G65/2606—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 the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—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 the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- 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
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Polyethers (AREA)
- Carbon And Carbon Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/199,916 US6835801B2 (en) | 2002-07-19 | 2002-07-19 | Activated starter mixtures and the processes related thereto |
| US10/199,916 | 2002-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2434864A1 CA2434864A1 (en) | 2004-01-19 |
| CA2434864C true CA2434864C (en) | 2010-09-14 |
Family
ID=29780237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2434864A Expired - Fee Related CA2434864C (en) | 2002-07-19 | 2003-07-03 | Activated starter mixtures and the processes related thereto |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6835801B2 (enExample) |
| EP (1) | EP1382629B1 (enExample) |
| JP (1) | JP4574964B2 (enExample) |
| KR (1) | KR100961362B1 (enExample) |
| CN (1) | CN100418993C (enExample) |
| AT (1) | ATE415437T1 (enExample) |
| BR (1) | BR0302450A (enExample) |
| CA (1) | CA2434864C (enExample) |
| DE (1) | DE60324864D1 (enExample) |
| ES (1) | ES2316672T3 (enExample) |
| MX (1) | MXPA03006392A (enExample) |
| PL (1) | PL214395B1 (enExample) |
| PT (1) | PT1382629E (enExample) |
| RU (1) | RU2346959C2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080108719A1 (en) * | 1999-10-25 | 2008-05-08 | Geiger Eric J | Phthalic Anhydride Based Polyester-Ether Polyols and Double Metal Cyanide Catalyst System for Preparing Same |
| US6696383B1 (en) * | 2002-09-20 | 2004-02-24 | Bayer Polymers Llc | Double-metal cyanide catalysts which can be used to prepare polyols and the processes related thereto |
| US20060223979A1 (en) * | 2005-04-04 | 2006-10-05 | Thomas Ostrowski | Process for preparing polyether polyols |
| DE102007057147A1 (de) | 2007-11-28 | 2009-06-04 | Evonik Goldschmidt Gmbh | Verfahren zur Alkoxylierung mit DMC-Katalysatoren im Schlaufenreaktor mit Strahlsauger |
| EP2241584B1 (en) | 2008-01-25 | 2012-03-21 | Kaneka Corporation | Process for producing polyalkylene oxide |
| US20100324340A1 (en) * | 2009-06-23 | 2010-12-23 | Bayer Materialscience Llc | Short chain polyether polyols prepared from ultra-low water-content starters via dmc catalysis |
| GB2482176A (en) * | 2010-07-23 | 2012-01-25 | Christopher Wickham Noakes | Production of polyols for use in low ball rebound polyurethane foams |
| EP3317322B1 (en) * | 2015-07-02 | 2019-04-10 | Covestro LLC | Process for preparing polyether polyol using dmc catalyst and continuous addition of starter |
| US9879114B2 (en) * | 2015-12-22 | 2018-01-30 | Covestro Llc | Process for the production of low molecular weight polyoxyalkylene polyols |
| CN107200837B (zh) | 2016-03-18 | 2019-10-18 | 淮安巴德聚氨酯科技有限公司 | 一种利用dmc催化剂循环制备聚醚多元醇的方法 |
| US10873316B2 (en) * | 2017-03-02 | 2020-12-22 | Samsung Electro-Mechanics Co., Ltd. | Acoustic resonator and method of manufacturing the same |
| CN109679085B (zh) * | 2019-01-18 | 2022-02-08 | 上海东大化学有限公司 | 一种窄分布无规聚醚及其制备方法 |
| CN113348191B (zh) | 2019-01-31 | 2023-06-30 | 陶氏环球技术有限责任公司 | 无雾聚氨酯制剂 |
| EP4279534A1 (en) | 2022-05-20 | 2023-11-22 | PCC ROKITA Spolka Akcyjna | A method for producing low unsaturation level oxyalkylates, an oxyalkylate, a use thereof and a polyurethane foam |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3278457A (en) * | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| US3427256A (en) * | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanide complex compounds |
| US3278459A (en) * | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| US3829505A (en) * | 1970-02-24 | 1974-08-13 | Gen Tire & Rubber Co | Polyethers and method for making the same |
| US3941849A (en) * | 1972-07-07 | 1976-03-02 | The General Tire & Rubber Company | Polyethers and method for making the same |
| AU551979B2 (en) * | 1982-03-31 | 1986-05-15 | Shell Internationale Research Maatschappij B.V. | Epoxy polymerisation catalysts |
| AU552988B2 (en) * | 1982-03-31 | 1986-06-26 | Shell Internationale Research Maatschappij B.V. | Polymerizing epoxides and catalyst suspensions for this |
| JP2910778B2 (ja) | 1990-06-29 | 1999-06-23 | 旭硝子株式会社 | ポリエーテル類の製造方法 |
| JP3025312B2 (ja) * | 1990-12-18 | 2000-03-27 | 旭硝子株式会社 | ポリエーテル類の製造法 |
| JPH0517569A (ja) | 1991-07-08 | 1993-01-26 | Asahi Glass Co Ltd | ポリエーテル類の製造方法 |
| JP3085740B2 (ja) | 1991-07-17 | 2000-09-11 | 旭硝子株式会社 | ポリエーテル類の製造方法 |
| US5158922A (en) * | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| JP3114481B2 (ja) * | 1993-05-25 | 2000-12-04 | トヨタ自動車株式会社 | 作業負担評価指数の算出方法とそのための装置とそれを利用した作業工程計画方法 |
| US5470813A (en) * | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
| US5482908A (en) * | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US5563221A (en) * | 1995-06-21 | 1996-10-08 | Arco Chemical Technology, L.P. | Process for making ethylene oxide-capped polyols from double metal cyanide-catalyzed polyols |
| US5545601A (en) * | 1995-08-22 | 1996-08-13 | Arco Chemical Technology, L.P. | Polyether-containing double metal cyanide catalysts |
| US5767323A (en) * | 1995-12-22 | 1998-06-16 | Arco Chemical Technology, L.P. | Process for preparing polyoxyalkylene polyether polyols having low levels of transition metals through double metal cyanide complex polyoxyalkylation |
| US5639705A (en) * | 1996-01-19 | 1997-06-17 | Arco Chemical Technology, L.P. | Double metal cyanide catalysts and methods for making them |
| US5777177A (en) * | 1996-02-07 | 1998-07-07 | Arco Chemical Technology, L.P. | Preparation of double metal cyanide-catalyzed polyols by continuous addition of starter |
| US5689012A (en) * | 1996-07-18 | 1997-11-18 | Arco Chemical Technology, L.P. | Continuous preparation of low unsaturation polyoxyalkylene polyether polyols with continuous additon of starter |
| US5844070A (en) * | 1997-05-16 | 1998-12-01 | Arco Chemical Technology, L.P. | Process for rapid activation of double metal cyanide catalysts |
| US6077978A (en) * | 1997-09-17 | 2000-06-20 | Arco Chemical Technology L.P. | Direct polyoxyalkylation of glycerine with double metal cyanide catalysis |
| JP2001519468A (ja) * | 1997-10-13 | 2001-10-23 | バイエル・アクチエンゲゼルシヤフト | ポリエーテルポリオールを製造するための結晶質複金属シアン化物触媒 |
| KR20020019949A (ko) | 1999-07-09 | 2002-03-13 | 그래햄 이. 테일러 | 금속 시아나이드 촉매를 사용한 에틸렌 옥사이드의 중합 |
| US6359101B1 (en) * | 1999-12-15 | 2002-03-19 | Synuthane International, Inc. | Preparing polyether polyols with DMC catalysts |
| US6491846B1 (en) * | 2001-06-21 | 2002-12-10 | Bayer Antwerpen, N.V. | Process for the in-situ production of polyol blends, the in-situ produced polyol blends, and their use in the production of viscoelastic foam |
-
2002
- 2002-07-19 US US10/199,916 patent/US6835801B2/en not_active Expired - Lifetime
-
2003
- 2003-07-03 CA CA2434864A patent/CA2434864C/en not_active Expired - Fee Related
- 2003-07-07 DE DE60324864T patent/DE60324864D1/de not_active Expired - Lifetime
- 2003-07-07 AT AT03015254T patent/ATE415437T1/de not_active IP Right Cessation
- 2003-07-07 PT PT03015254T patent/PT1382629E/pt unknown
- 2003-07-07 ES ES03015254T patent/ES2316672T3/es not_active Expired - Lifetime
- 2003-07-07 EP EP03015254A patent/EP1382629B1/en not_active Expired - Lifetime
- 2003-07-17 PL PL361330A patent/PL214395B1/pl unknown
- 2003-07-17 MX MXPA03006392A patent/MXPA03006392A/es active IP Right Grant
- 2003-07-17 BR BR0302450-4A patent/BR0302450A/pt not_active IP Right Cessation
- 2003-07-18 KR KR1020030049013A patent/KR100961362B1/ko not_active Expired - Fee Related
- 2003-07-18 RU RU2003122077/04A patent/RU2346959C2/ru not_active IP Right Cessation
- 2003-07-18 JP JP2003276622A patent/JP4574964B2/ja not_active Expired - Fee Related
- 2003-07-18 CN CNB031550290A patent/CN100418993C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1064395A1 (en) | 2005-01-28 |
| KR100961362B1 (ko) | 2010-06-04 |
| ES2316672T3 (es) | 2009-04-16 |
| MXPA03006392A (es) | 2005-08-16 |
| EP1382629B1 (en) | 2008-11-26 |
| CN100418993C (zh) | 2008-09-17 |
| EP1382629A1 (en) | 2004-01-21 |
| PT1382629E (pt) | 2009-02-03 |
| RU2346959C2 (ru) | 2009-02-20 |
| CN1487000A (zh) | 2004-04-07 |
| KR20040010239A (ko) | 2004-01-31 |
| JP2004051996A (ja) | 2004-02-19 |
| ATE415437T1 (de) | 2008-12-15 |
| DE60324864D1 (de) | 2009-01-08 |
| US20040014908A1 (en) | 2004-01-22 |
| CA2434864A1 (en) | 2004-01-19 |
| BR0302450A (pt) | 2004-08-24 |
| RU2003122077A (ru) | 2005-02-10 |
| JP4574964B2 (ja) | 2010-11-04 |
| PL361330A1 (en) | 2004-01-26 |
| PL214395B1 (pl) | 2013-07-31 |
| US6835801B2 (en) | 2004-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170704 |