KR100610285B1 - 고함량의 1차 oh기를 갖는 장쇄 폴리에테르 폴리올 - Google Patents
고함량의 1차 oh기를 갖는 장쇄 폴리에테르 폴리올 Download PDFInfo
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- KR100610285B1 KR100610285B1 KR1020017013535A KR20017013535A KR100610285B1 KR 100610285 B1 KR100610285 B1 KR 100610285B1 KR 1020017013535 A KR1020017013535 A KR 1020017013535A KR 20017013535 A KR20017013535 A KR 20017013535A KR 100610285 B1 KR100610285 B1 KR 100610285B1
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- KR
- South Korea
- Prior art keywords
- dmc
- mol
- primary
- polyether polyols
- propylene oxide
- Prior art date
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- 229920005862 polyol Polymers 0.000 title claims abstract description 57
- 150000003077 polyols Chemical class 0.000 title claims abstract description 57
- 229920000570 polyether Polymers 0.000 title claims abstract description 45
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 32
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 41
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000007858 starting material Substances 0.000 claims abstract description 20
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims 1
- 229920003226 polyurethane urea Polymers 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- -1 poly (oxypropylene) Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 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 description 1
- 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 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 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
- 239000003513 alkali Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- SZAVHWMCBDFDCM-KTTJZPQESA-N cobalt-60(3+);hexacyanide Chemical compound [60Co+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SZAVHWMCBDFDCM-KTTJZPQESA-N 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
- 230000000536 complexating effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
-
- 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
-
- 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
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
- 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
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- 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)
- Polyurethanes Or Polyureas (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Description
Claims (11)
- 이중-금속 시아나이드 (DMC) 촉매의 존재 하에 제조된 폴리(옥시에틸렌/옥시프로필렌) 말단 블록을 갖는, 1차 OH기 함량이 50 내지 95 몰%이며, 옥시에틸렌 단위의 전체 함량이 25 중량% 초과인 폴리에테르 폴리올.
- 제1항에 있어서, 수평균 분자량이 1,000 내지 100,000 g/몰인 폴리에테르 폴리올.
- 활성 수소원자를 갖는 출발 화합물을 에틸렌 옥시드 (EO)/프로필렌 옥시드 (PO)의 혼합물 (EO:PO의 중량비=40:60 내지 95:5)과 DMC-촉매된 중부가반응에 의해 반응시키는, 제1항 또는 제2항에 따른 폴리올의 제조 방법.
- 제3항에 있어서, 1 내지 8개의 히드록실기 및 18 내지 2,000 g/몰의 분자량을 갖는 출발 화합물을 사용하는 방법.
- 제3항에 있어서, 1 내지 8개의 히드록실기 및 200 내지 2,000 g/몰의 수평균 분자량을 갖는 올리고머 프로폭실화 출발 화합물을 활성 수소원자를 갖는 출발 화합물로서 사용하는 방법.
- 제3항에 있어서, 우선 활성 수소원자를 갖는 출발 화합물을 DMC-촉매된 프로폭실화에 의해 신장시키며, 이어서 이 신장된 프로폭실화 중간체로부터, 말단 블록으로서 에틸렌 옥시드(EO)/프로필렌 옥시드(PO)의 혼합물 (EO:PO의 중량비=40:60 내지 95:5)에의 DMC-촉매된 중부가반응에 의해 50 내지 95 몰%의 1차 OH기 함량 및 25 중량% 초과의 옥시에틸렌 단위 전체 함량을 갖는 장쇄 폴리에테르 폴리올을 제조하는 방법.
- 제3항에 있어서, 활성 수소원자를 갖는 출발 화합물에 대한, 말단 블록으로서 에틸렌 옥시드/프로필렌 옥시드 혼합물의 DMC-촉매된 중부가반응을 20 ℃ 내지 200 ℃의 온도 및 0.001 내지 20 바아의 전체 압력에서, 임의로 불활성 유기 용매의 존재하에 수행하는 방법.
- 제3항에 있어서, DMC-촉매를 제조되는 폴리에테르 폴리올의 양 기준으로 0.001 중량% 내지 0.1 중량%의 농도로 사용하는 방법.
- 제1항 또는 제2항에 따른 폴리에테르 폴리올을 사용하여 제조된 폴리우레탄.
- 제1항 또는 제2항에 따른 폴리에테르 폴리올을 사용하여 제조된 폴리우레탄 우레아.
- 제1항 또는 제2항에 따른 폴리에테르 폴리올을 사용하여 제조된 폴리우레아.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19918727A DE19918727A1 (de) | 1999-04-24 | 1999-04-24 | Langkettige Polyetherpolyole mit hohem Anteil primärer OH-Gruppen |
DE19918727.4 | 1999-04-24 | ||
PCT/EP2000/003217 WO2000064963A1 (de) | 1999-04-24 | 2000-04-11 | Langkettige polyetherpolyole mit hohem anteil primärer oh-gruppen |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20010110796A KR20010110796A (ko) | 2001-12-13 |
KR100610285B1 true KR100610285B1 (ko) | 2006-08-09 |
Family
ID=7905780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020017013535A KR100610285B1 (ko) | 1999-04-24 | 2000-04-11 | 고함량의 1차 oh기를 갖는 장쇄 폴리에테르 폴리올 |
Country Status (20)
Country | Link |
---|---|
US (1) | US6617419B1 (ko) |
EP (1) | EP1173498B1 (ko) |
JP (1) | JP2002543228A (ko) |
KR (1) | KR100610285B1 (ko) |
CN (1) | CN1183180C (ko) |
AT (1) | ATE273339T1 (ko) |
AU (1) | AU3819600A (ko) |
BR (1) | BR0010002B1 (ko) |
CA (1) | CA2367670C (ko) |
CZ (1) | CZ296406B6 (ko) |
DE (2) | DE19918727A1 (ko) |
ES (1) | ES2226804T3 (ko) |
HK (1) | HK1046147B (ko) |
HU (1) | HU228388B1 (ko) |
ID (1) | ID30542A (ko) |
MX (1) | MXPA01010737A (ko) |
PL (1) | PL199860B1 (ko) |
PT (1) | PT1173498E (ko) |
RU (1) | RU2242485C2 (ko) |
WO (1) | WO2000064963A1 (ko) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19928156A1 (de) * | 1999-06-19 | 2000-12-28 | Bayer Ag | Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume |
JP4277686B2 (ja) | 2002-01-22 | 2009-06-10 | 旭硝子株式会社 | ポリエーテル類の連続製造方法 |
JP4273876B2 (ja) * | 2003-08-25 | 2009-06-03 | 旭硝子株式会社 | ポリエーテルモノオールまたはポリエーテルポリオールおよびその製造方法 |
JP2007508406A (ja) * | 2003-10-10 | 2007-04-05 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ポリエーテルポリオールの製造方法 |
JP4899508B2 (ja) * | 2006-02-03 | 2012-03-21 | 旭硝子株式会社 | ポリエーテルポリオールの製造方法 |
CN100588669C (zh) * | 2006-11-28 | 2010-02-10 | 王伟松 | 烯丙醇无规聚醚的制备方法 |
DE102007002555A1 (de) * | 2007-01-17 | 2008-07-24 | Bayer Materialscience Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
DE102007057147A1 (de) | 2007-11-28 | 2009-06-04 | Evonik Goldschmidt Gmbh | Verfahren zur Alkoxylierung mit DMC-Katalysatoren im Schlaufenreaktor mit Strahlsauger |
CN101925631B (zh) * | 2008-01-25 | 2013-01-16 | 株式会社钟化 | 聚环氧烷烃的制造方法 |
EP2471832B1 (en) * | 2009-10-05 | 2017-06-14 | Asahi Glass Company, Limited | Method for producing soft polyurethane foam and seat |
US20110230581A1 (en) * | 2010-03-17 | 2011-09-22 | Bayer Materialscience Llc | Process for the production of polyether polyols with a high ethylene oxide content |
WO2011136367A1 (ja) * | 2010-04-30 | 2011-11-03 | 旭硝子株式会社 | ポリオキシアルキレンポリオール、ポリマー分散ポリオール、および軟質ポリウレタンフォーム、ならびにこれらの製造方法 |
JP5648797B2 (ja) * | 2010-11-22 | 2015-01-07 | 旭硝子株式会社 | ポリエーテルヒドロキシ化合物の製造方法 |
EP2530101A1 (de) * | 2011-06-01 | 2012-12-05 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
CN102417594A (zh) * | 2011-10-14 | 2012-04-18 | 滨州市华茂工贸有限公司 | 缩合醇无规聚醚的配方、生产工艺及应用 |
WO2013092501A1 (de) | 2011-12-20 | 2013-06-27 | Bayer Intellectual Property Gmbh | Hydroxy-aminopolymere und verfahren zu deren herstellung |
WO2013157486A1 (ja) * | 2012-04-18 | 2013-10-24 | 旭硝子株式会社 | ポリエーテル類の製造方法 |
US9051412B2 (en) * | 2013-03-14 | 2015-06-09 | Bayer Materialscience Llc | Base-catalyzed, long chain, active polyethers from short chain DMC-catalyzed starters |
CN107075107A (zh) * | 2014-11-07 | 2017-08-18 | 出光兴产株式会社 | 聚亚烷基二醇的制造方法、粘度指数改进剂、润滑油组合物和润滑油组合物的制造方法 |
AR104981A1 (es) * | 2015-06-20 | 2017-08-30 | Dow Global Technologies Llc | Proceso continuo para producir polioles de poliéter que tienen un elevado contenido de óxido de etileno polimerizado, mediante el uso de un complejo catalizador de cianuro de metal doble y un compuesto metálico de la serie de lantanida o metal del grupo 3 - grupo 15, magnesio |
WO2019055177A1 (en) * | 2017-09-15 | 2019-03-21 | Dow Global Technologies Llc | CONTINUOUS PROCESS FOR THE PRODUCTION OF POLYETHER POLYOLS |
PL3707192T3 (pl) | 2017-11-06 | 2023-07-31 | Shell Internationale Research Maatschappij B.V. | Sposób wytwarzania poliolu polieterowego o wysokiej zawartości tlenku etylenu |
JP7202524B2 (ja) * | 2019-01-21 | 2023-01-12 | 日油株式会社 | アルキレンオキシド誘導体、潤滑剤、消泡剤、化粧品用基材およびそれを含む化粧料 |
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CN111303403B (zh) * | 2020-04-13 | 2022-06-14 | 山东蓝星东大有限公司 | 端多羟基聚醚多元醇制备方法 |
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- 2000-04-11 CA CA002367670A patent/CA2367670C/en not_active Expired - Fee Related
- 2000-04-11 PL PL351384A patent/PL199860B1/pl unknown
- 2000-04-11 DE DE50007388T patent/DE50007388D1/de not_active Expired - Lifetime
- 2000-04-11 ID IDW00200102276A patent/ID30542A/id unknown
- 2000-04-11 MX MXPA01010737A patent/MXPA01010737A/es active IP Right Grant
- 2000-04-11 HU HU0200782A patent/HU228388B1/hu not_active IP Right Cessation
- 2000-04-11 KR KR1020017013535A patent/KR100610285B1/ko active IP Right Grant
- 2000-04-11 BR BRPI0010002-1A patent/BR0010002B1/pt not_active IP Right Cessation
- 2000-04-11 CN CNB008067120A patent/CN1183180C/zh not_active Expired - Lifetime
- 2000-04-11 PT PT00917070T patent/PT1173498E/pt unknown
- 2000-04-11 EP EP00917070A patent/EP1173498B1/de not_active Expired - Lifetime
- 2000-04-11 RU RU2001131893/04A patent/RU2242485C2/ru not_active IP Right Cessation
- 2000-04-11 CZ CZ20013761A patent/CZ296406B6/cs not_active IP Right Cessation
- 2000-04-11 WO PCT/EP2000/003217 patent/WO2000064963A1/de active IP Right Grant
- 2000-04-11 AU AU38196/00A patent/AU3819600A/en not_active Abandoned
- 2000-04-11 US US10/009,889 patent/US6617419B1/en not_active Expired - Lifetime
- 2000-04-11 ES ES00917070T patent/ES2226804T3/es not_active Expired - Lifetime
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US6617419B1 (en) | 2003-09-09 |
ATE273339T1 (de) | 2004-08-15 |
PL199860B1 (pl) | 2008-11-28 |
ID30542A (id) | 2001-12-20 |
BR0010002B1 (pt) | 2010-06-15 |
AU3819600A (en) | 2000-11-10 |
CN1183180C (zh) | 2005-01-05 |
JP2002543228A (ja) | 2002-12-17 |
CZ296406B6 (cs) | 2006-03-15 |
HU228388B1 (en) | 2013-03-28 |
ES2226804T3 (es) | 2005-04-01 |
RU2242485C2 (ru) | 2004-12-20 |
CA2367670A1 (en) | 2000-11-02 |
CA2367670C (en) | 2008-10-07 |
DE19918727A1 (de) | 2000-10-26 |
DE50007388D1 (de) | 2004-09-16 |
CN1348476A (zh) | 2002-05-08 |
HK1046147A1 (en) | 2002-12-27 |
EP1173498A1 (de) | 2002-01-23 |
MXPA01010737A (es) | 2002-06-04 |
HUP0200782A2 (en) | 2002-06-29 |
PL351384A1 (en) | 2003-04-07 |
HK1046147B (zh) | 2005-08-19 |
KR20010110796A (ko) | 2001-12-13 |
BR0010002A (pt) | 2002-01-08 |
HUP0200782A3 (en) | 2004-03-29 |
CZ20013761A3 (cs) | 2002-04-17 |
EP1173498B1 (de) | 2004-08-11 |
PT1173498E (pt) | 2005-01-31 |
WO2000064963A1 (de) | 2000-11-02 |
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