PT2115032E - Processo para o fabrico de polióis de poliétercarbonato - Google Patents
Processo para o fabrico de polióis de poliétercarbonato Download PDFInfo
- Publication number
- PT2115032E PT2115032E PT08708045T PT08708045T PT2115032E PT 2115032 E PT2115032 E PT 2115032E PT 08708045 T PT08708045 T PT 08708045T PT 08708045 T PT08708045 T PT 08708045T PT 2115032 E PT2115032 E PT 2115032E
- Authority
- PT
- Portugal
- Prior art keywords
- reaction
- weight
- carbon dioxide
- reactor
- polyols
- Prior art date
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 235000011037 adipic acid Nutrition 0.000 description 1
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
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- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
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- 150000004985 diamines Chemical class 0.000 description 1
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- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
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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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- 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
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
-
- 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
-
- 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
-
- 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)
- Polyesters Or Polycarbonates (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07101407 | 2007-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT2115032E true PT2115032E (pt) | 2011-02-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT08708045T PT2115032E (pt) | 2007-01-30 | 2008-01-21 | Processo para o fabrico de polióis de poliétercarbonato |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8324419B2 (https=) |
| EP (1) | EP2115032B2 (https=) |
| JP (1) | JP5512283B2 (https=) |
| KR (1) | KR101460381B1 (https=) |
| CN (1) | CN101611074B (https=) |
| AT (1) | ATE493457T1 (https=) |
| DE (1) | DE502008002134D1 (https=) |
| ES (1) | ES2358861T5 (https=) |
| MX (1) | MX2009007771A (https=) |
| PT (1) | PT2115032E (https=) |
| WO (1) | WO2008092767A1 (https=) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103333330A (zh) | 2008-09-08 | 2013-10-02 | 诺沃梅尔公司 | 聚碳酸酯多元醇组合物和方法 |
| JP5543114B2 (ja) * | 2009-01-21 | 2014-07-09 | 花王株式会社 | 毛髪化粧料 |
| WO2010084993A1 (en) * | 2009-01-21 | 2010-07-29 | Kao Corporation | Hair cosmetic composition |
| JP5543115B2 (ja) * | 2009-01-21 | 2014-07-09 | 花王株式会社 | 毛髪化粧料 |
| DE102010008410A1 (de) * | 2010-02-18 | 2011-08-18 | Bayer MaterialScience AG, 51373 | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| MX2012011003A (es) * | 2010-03-24 | 2012-10-15 | Bayer Ip Gmbh | Procedimiento para la preparacion de polioletercarbonatos. |
| EP2591036B1 (de) | 2010-07-05 | 2014-03-26 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von polyolgemischen |
| EP2441788A1 (de) * | 2010-10-14 | 2012-04-18 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
| EP3584265B1 (en) * | 2010-11-23 | 2023-03-15 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions |
| EP2465890A1 (de) * | 2010-12-17 | 2012-06-20 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen mit primären Hydroxyl-Endgruppen und daraus hergestellte Polyurethanpolymere |
| KR101404702B1 (ko) * | 2011-03-08 | 2014-06-17 | 에스케이이노베이션 주식회사 | 에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 |
| CN103547368B (zh) * | 2011-04-04 | 2017-10-27 | 汉高股份有限及两合公司 | 用于环氧化物聚合以及用于环氧化物与二氧化碳的共聚合的催化剂 |
| US9492957B2 (en) | 2011-04-27 | 2016-11-15 | Basf Se | Extruded plastics profiles comprising continuously introduced insulation elements |
| EP2530101A1 (de) | 2011-06-01 | 2012-12-05 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
| EP2548905A1 (de) * | 2011-07-18 | 2013-01-23 | Bayer MaterialScience AG | Verfahren zur Aktivierung von Doppelmetallcyanidkatalysatoren zur Herstellung von Polyetherpolyolen |
| EP2548907A1 (de) * | 2011-07-18 | 2013-01-23 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
| EP2548906A1 (de) * | 2011-07-18 | 2013-01-23 | Bayer MaterialScience AG | Verfahren zur Aktivierung von Doppelmetallcyanidkatalysatoren zur Herstellung von Polyetherpolyolen |
| EP2548908A1 (de) * | 2011-07-18 | 2013-01-23 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
| IN2014CN01299A (https=) | 2011-07-25 | 2015-04-24 | Novomer Inc | |
| US8797966B2 (en) | 2011-09-23 | 2014-08-05 | Ofinno Technologies, Llc | Channel state information transmission |
| MY184782A (en) * | 2011-11-03 | 2021-04-21 | Malaysian Palm Oil Board | A method to produce copolymers of tetrahydrofuran and epoxidized natural oils |
| US8885569B2 (en) | 2011-12-19 | 2014-11-11 | Ofinno Technologies, Llc | Beamforming signaling in a wireless network |
| EP2630950A1 (en) | 2012-02-21 | 2013-08-28 | Kao Germany GmbH | Hair treatment method |
| EP2703425A1 (de) * | 2012-08-27 | 2014-03-05 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| EP2703426A1 (de) * | 2012-08-27 | 2014-03-05 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| DE102012218846A1 (de) * | 2012-10-16 | 2014-04-17 | Bayer Materialscience Ag | Herstellung und Verwendung neuer thermoplastischer Polyurethan-Elastomere auf Basis von Polyethercarbonatpolyolen |
| DE102012218848A1 (de) | 2012-10-16 | 2014-04-17 | Bayer Materialscience Ag | Herstellung und Verwendung neuer thermoplastischer Polyurethan-Elastomere auf Basis von Polyethercarbonatpolyolen |
| EP2725044B1 (de) * | 2012-10-24 | 2017-06-21 | Covestro Deutschland AG | Alkoxysilanterminiertes Präpolymer auf Basis von Polyethercarbonatpolyolen für Sprühschäume |
| CN105229047B (zh) | 2012-11-07 | 2018-07-20 | 沙特阿美技术公司 | 高强度聚氨酯泡沫组合物及方法 |
| CN104277194B (zh) | 2013-07-05 | 2018-11-30 | 科思创德国股份有限公司 | 聚氨酯树脂组合物以及由其制备的聚氨酯复合物 |
| EP2845872A1 (de) * | 2013-09-05 | 2015-03-11 | Bayer MaterialScience AG | Niederviskose Polyethercarbonatpolyole mit Seitenketten |
| WO2015032720A1 (de) * | 2013-09-05 | 2015-03-12 | Bayer Materialscience Ag | Höherfunktionelle polyethercarbonatpolyole erhalten unter einsatz von verzweigermolekülen |
| EP2845873A1 (de) * | 2013-09-05 | 2015-03-11 | Bayer MaterialScience AG | Radikalische Vernetzung von Polyethercarbonatpolyolen enthaltend elektronenarme und elektronenreiche Doppelbindungen |
| KR101535569B1 (ko) | 2013-09-09 | 2015-07-09 | 주식회사 엘지화학 | 폴리알킬렌카보네이트 수지 및 이의 제조방법 |
| EP2851384A1 (de) | 2013-09-20 | 2015-03-25 | Bayer MaterialScience AG | Verzweigte Polyethercarbonatpolyole und Verfahren zu deren Herstellung |
| EP2865700A1 (de) | 2013-10-23 | 2015-04-29 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| JP2016539231A (ja) | 2013-11-27 | 2016-12-15 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ポリウレタンソフト発泡体を製造するためのポリエーテルカーボネートポリオールとポリエーテルポリオールとの混合物 |
| DE102013224708A1 (de) * | 2013-12-03 | 2015-06-03 | Evonik Industries Ag | Alkoxysilylhaltige Klebdichtstoffe mit intrinsisch reduzierter Viskosität |
| EP2886572A1 (de) | 2013-12-17 | 2015-06-24 | Bayer MaterialScience AG | Einsatz von Urethan-Alkoholen zur Herstellung von Polyethercarbonatpolyolen |
| EP2894180A1 (en) * | 2014-01-08 | 2015-07-15 | Bayer MaterialScience AG | Polymer Polyols comprising a Polyether Carbonate Polyol as the Base Polyol |
| EP2910585B1 (de) | 2014-02-21 | 2018-07-04 | Covestro Deutschland AG | Schotterkörper sowie Verfahren zur Herstellung von Schotterkörpern |
| US9657135B2 (en) | 2014-02-26 | 2017-05-23 | Covestro Deutschland Ag | Method for producing polyether ester carbonate polyols |
| WO2015162125A1 (de) | 2014-04-24 | 2015-10-29 | Bayer Material Science Ag | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| KR102333890B1 (ko) * | 2014-07-03 | 2021-12-02 | 코베스트로 도이칠란트 아게 | 폴리에테르 카르보네이트 폴리올의 제조 방법 |
| WO2016001164A1 (de) * | 2014-07-03 | 2016-01-07 | Covestro Deutschland Ag | Verfahren zur reinigung von polycarbonatpolyolen und reinigungsvorrichtung hierfür |
| EP3023447A1 (de) * | 2014-11-18 | 2016-05-25 | Covestro Deutschland AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| EP3050907A1 (de) | 2015-01-28 | 2016-08-03 | Covestro Deutschland AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| US20180237577A1 (en) | 2015-02-27 | 2018-08-23 | Covestro Deutschland Ag | Use of polyether carbonate polyols for producing polyurethane foams with stable colour |
| EP3067376A1 (de) | 2015-03-11 | 2016-09-14 | Evonik Degussa GmbH | Herstellung von Polyurethansystemen unter Einsatz von Polyetherpolycarbonatpolyolen |
| US10662364B2 (en) | 2015-03-20 | 2020-05-26 | Resinate Materials Group, Inc. | Drilling fluids containing polyester polyols |
| WO2016174027A1 (de) | 2015-04-28 | 2016-11-03 | Covestro Deutschland Ag | Polyurethanummantelungen mit verminderter wasseraufnahme und deren verwendung |
| EP3098252A1 (de) | 2015-05-26 | 2016-11-30 | Covestro Deutschland AG | Einsatz von alkoholen, die mindestens zwei urethangruppen enthalten, zur herstellung von polyethercarbonatpolyolen |
| EP3098250A1 (de) | 2015-05-26 | 2016-11-30 | Covestro Deutschland AG | Verfahren zur herstellung von polyethercarbonatpolyolen |
| CN108473657A (zh) | 2015-11-19 | 2018-08-31 | 科思创德国股份有限公司 | 基于聚醚碳酸酯多元醇的聚氨酯泡沫材料 |
| PL3387035T3 (pl) | 2015-12-09 | 2022-08-16 | Covestro Intellectual Property Gmbh & Co. Kg | Poliuretanowe materiały piankowe na bazie polioli polieterowęglanowych |
| EP3178858A1 (de) | 2015-12-09 | 2017-06-14 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| US10119223B2 (en) * | 2016-07-15 | 2018-11-06 | Covestro Llc | Carpet and synthetic turf backings prepared from a polyether carbonate polyol |
| TWI758322B (zh) | 2016-09-09 | 2022-03-21 | 德商科思創德意志股份有限公司 | 以熱塑性聚胺甲酸酯為主之熔紡複絲、其製造及用途 |
| AU2017330346C1 (en) | 2016-09-21 | 2025-03-06 | Nextcure, Inc. | Antibodies for Siglec-15 and methods of use thereof |
| EP3538588B1 (en) * | 2016-11-11 | 2023-01-25 | Dow Global Technologies LLC | Polycarbonate based polyols |
| KR101867721B1 (ko) | 2016-12-16 | 2018-06-14 | 주식회사 포스코 | 폴리에테르 카보네이트 폴리올 제조공정에서의 프로필렌 카보네이트의 분리방법 |
| EP3336137A1 (de) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Verwendung von physikalischen treibmitteln zur erzeugung von polyethercarbonatpolyol-basierten polyurethanschaumstoffen mit reduzierter emission von cyclischem propylencarbonat |
| WO2018169833A1 (en) | 2017-03-15 | 2018-09-20 | Covestro Llc | Viscoelastic polyurethane foams with reduced temperature sensitivity |
| US10053533B1 (en) | 2017-04-13 | 2018-08-21 | Presidium Usa, Inc. | Oligomeric polyol compositions |
| EP3409704A1 (de) | 2017-06-01 | 2018-12-05 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| GB201717459D0 (en) | 2017-10-24 | 2017-12-06 | Econic Tech Limited | Methods for forming polycarbonate ether polyols and high molecular weight polyether carbonates |
| US20190119444A1 (en) | 2017-10-25 | 2019-04-25 | Covestro Llc | Process to remove dmc catalysts from polyether carbonate polyols |
| CN111936542A (zh) | 2018-03-07 | 2020-11-13 | 科思创知识产权两合公司 | 基于聚醚碳酸酯多元醇的聚氨酯泡沫材料 |
| EP3536727A1 (de) | 2018-03-07 | 2019-09-11 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| CN111954689A (zh) | 2018-03-22 | 2020-11-17 | 科思创知识产权两合公司 | 制备具有高的粗密度的聚氨酯软质泡沫材料的方法 |
| EP3543268A1 (de) | 2018-03-22 | 2019-09-25 | Covestro Deutschland AG | Verfahren zur herstellung von polyurethanweichschaumstoffen |
| EP3549969A1 (de) | 2018-04-06 | 2019-10-09 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| WO2020028606A1 (en) | 2018-08-02 | 2020-02-06 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| EP3617248A1 (de) | 2018-08-30 | 2020-03-04 | Covestro Deutschland AG | Verfahren zur abtrennung von gasförmigen bestandteilen |
| GB201814526D0 (en) | 2018-09-06 | 2018-10-24 | Econic Tech Ltd | Methods for forming polycarbonate ether polyols and high molecular weight polyether carbonates |
| US10793692B2 (en) | 2018-10-24 | 2020-10-06 | Covestro Llc | Viscoelastic flexible foams comprising hydroxyl-terminated prepolymers |
| ES2988729T3 (es) * | 2019-01-31 | 2024-11-21 | Dow Global Technologies Llc | Proceso de purificación de poliéteres de carbonato poliol |
| EP3763768A1 (de) * | 2019-07-12 | 2021-01-13 | Covestro Deutschland AG | Polyethercarbonatpolyole mit enger segmentlängenverteilung |
| WO2021032555A1 (de) * | 2019-08-19 | 2021-02-25 | Covestro Deutschland Ag | Verfahren zur herstellung von polyethercarbonatalkoholen |
| EP3783046A1 (de) * | 2019-08-19 | 2021-02-24 | Covestro Deutschland AG | Verfahren zur herstellung von polyethercarbonatpolyolen |
| US20240025094A1 (en) | 2019-10-09 | 2024-01-25 | Covestro Llc | Methods, systems and computer program products for producing polyurethane foam products using optical and infrared imaging |
| CN110922577B (zh) * | 2019-12-10 | 2022-08-23 | 长华化学科技股份有限公司 | 聚醚碳酸酯多元醇的制备方法 |
| EP3838964A1 (de) | 2019-12-18 | 2021-06-23 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP3892660A1 (de) | 2020-04-08 | 2021-10-13 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP3916055A1 (de) | 2020-05-26 | 2021-12-01 | Covestro Deutschland AG | Polycarbonat-zusammensetzungen enthaltend polyethercarbonatpolyole |
| EP3988600A1 (de) | 2020-10-20 | 2022-04-27 | Covestro Deutschland AG | Verfahren zur herstellung von polyethercarbonatalkoholen |
| US11572433B2 (en) | 2021-03-12 | 2023-02-07 | Covestro Llc | In-situ formed polyols, a process for their preparation, foams prepared from these in-situ formed polyols and a process for their preparation |
| EP4089127A1 (en) | 2021-05-12 | 2022-11-16 | Covestro Deutschland AG | Cast polyurethane elastomers and production thereof |
| EP4101873A1 (de) | 2021-06-11 | 2022-12-14 | Covestro Deutschland AG | Einsatz von bismut-katalysatoren zur verringerung von cyclischem propylencarbonat bei der herstellung von weichschaumstoffen basierend auf polyethercarbonatpolyolen |
| US12195576B2 (en) | 2021-06-23 | 2025-01-14 | Saudi Aramco Technologies Company | Polyol compositions and methods |
| US11718705B2 (en) | 2021-07-28 | 2023-08-08 | Covestro Llc | In-situ formed polyether polyols, a process for their preparation, and a process for the preparation of polyurethane foams |
| US20230039276A1 (en) | 2021-07-28 | 2023-02-09 | Covestro Llc | Novel polyether polyol blends, a process for their preparation, foams prepared from these polyether polyol blends and a process for their preparation |
| EP4194476A1 (de) | 2021-12-07 | 2023-06-14 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP4444778A1 (en) | 2021-12-08 | 2024-10-16 | Covestro Deutschland AG | Polyurethane elastomer with improved hydrolysis resistance |
| DE112023002007T5 (de) * | 2022-04-22 | 2025-02-20 | AGC Inc. | Haftmittelzusammensetzung, ausgehärtetes produkt der haftmittelzusammensetzung und verfahren zur herstellung der haftmittelzusammensetzung |
| CN116478391B (zh) * | 2023-01-06 | 2024-01-30 | 四川长宁天然气开发有限责任公司 | 常温破乳剂及其制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2711002A1 (de) | 1977-03-14 | 1978-09-28 | Henkel Kgaa | Verfahren zur herstellung von waessrigen ueberzugsmitteln bzw. lacken |
| US4500704A (en) | 1983-08-15 | 1985-02-19 | The Dow Chemical Company | Carbon dioxide oxirane copolymers prepared using double metal cyanide complexes |
| GB8528071D0 (en) † | 1985-11-14 | 1985-12-18 | Shell Int Research | Polycarbonates |
| 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 |
| US5856369A (en) * | 1996-07-30 | 1999-01-05 | Osi Specialties, Inc. | Polyethers and polysiloxane copolymers manufactured with double metal cyanide catalysts |
| JP3933790B2 (ja) * | 1998-05-01 | 2007-06-20 | 三井化学株式会社 | ポリオキシアルキレンポリオール及びポリマー分散ポリオール |
| US20030191274A1 (en) | 2001-10-10 | 2003-10-09 | Kurth Thomas M. | Oxylated vegetable-based polyol having increased functionality and urethane material formed using the polyol |
| 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 |
| US20030143910A1 (en) | 2002-01-31 | 2003-07-31 | Mashburn Larry E. | Carpet backings prepared from vegetable oil-based polyurethanes |
| US6762278B2 (en) | 2002-02-04 | 2004-07-13 | Basf Corporation | Process for the copolymerization of alkylene oxides and carbon dioxide using suspensions of multi-metal cyanide compounds |
| DE10219028A1 (de) | 2002-04-29 | 2003-11-06 | Bayer Ag | Herstellung und Verwendung von hochmolekularen aliphatischen Polycarbonaten |
| DE10240186A1 (de) | 2002-08-28 | 2004-03-11 | Basf Ag | Verfahren zur Herstellung von emissionsarmen Polyurethan-Weichschaumstoffen |
| DE10244283A1 (de) † | 2002-09-23 | 2004-04-01 | Basf Ag | Verfahren zur Herstellung von Polyetheralkoholen |
| US6713599B1 (en) | 2003-03-31 | 2004-03-30 | Basf Corporation | Formation of polymer polyols with a narrow polydispersity using double metal cyanide (DMC) catalysts |
| WO2004096883A1 (en) | 2003-04-25 | 2004-11-11 | Dow Global Technologies Inc. | Dow global technologies inc |
| WO2004096882A1 (en) | 2003-04-25 | 2004-11-11 | Dow Global Technologies, Inc. | Vegetable oil based polyols and polyurethanes made therefrom |
| EP1628766B1 (en) † | 2003-05-22 | 2007-01-24 | Dow Global Technologies Inc. | Nano-scale dmc catalyst particles |
| US7671228B2 (en) * | 2005-03-29 | 2010-03-02 | Basf Corporation | Method of forming a polyethercarbonate polyol using a CO2-philic compound or substituent |
| US20060223973A1 (en) * | 2005-03-29 | 2006-10-05 | Basf Corporation | Method of forming a polyethercarbonate polyol |
| US7977501B2 (en) | 2006-07-24 | 2011-07-12 | Bayer Materialscience Llc | Polyether carbonate polyols made via double metal cyanide (DMC) catalysis |
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2008
- 2008-01-21 CN CN2008800036580A patent/CN101611074B/zh not_active Expired - Fee Related
- 2008-01-21 US US12/524,005 patent/US8324419B2/en not_active Expired - Fee Related
- 2008-01-21 ES ES08708045.3T patent/ES2358861T5/es active Active
- 2008-01-21 JP JP2009547634A patent/JP5512283B2/ja not_active Expired - Fee Related
- 2008-01-21 KR KR20097017807A patent/KR101460381B1/ko not_active Expired - Fee Related
- 2008-01-21 WO PCT/EP2008/050646 patent/WO2008092767A1/de not_active Ceased
- 2008-01-21 AT AT08708045T patent/ATE493457T1/de active
- 2008-01-21 PT PT08708045T patent/PT2115032E/pt unknown
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- 2008-01-21 DE DE200850002134 patent/DE502008002134D1/de active Active
- 2008-01-21 EP EP08708045.3A patent/EP2115032B2/de not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| EP2115032A1 (de) | 2009-11-11 |
| CN101611074A (zh) | 2009-12-23 |
| ATE493457T1 (de) | 2011-01-15 |
| US8324419B2 (en) | 2012-12-04 |
| CN101611074B (zh) | 2012-07-25 |
| DE502008002134D1 (de) | 2011-02-10 |
| ES2358861T5 (es) | 2014-12-10 |
| JP2010516796A (ja) | 2010-05-20 |
| EP2115032B1 (de) | 2010-12-29 |
| EP2115032B2 (de) | 2014-10-22 |
| KR20090107555A (ko) | 2009-10-13 |
| ES2358861T3 (es) | 2011-05-16 |
| MX2009007771A (es) | 2009-07-30 |
| KR101460381B1 (ko) | 2014-11-12 |
| WO2008092767A1 (de) | 2008-08-07 |
| US20100048935A1 (en) | 2010-02-25 |
| JP5512283B2 (ja) | 2014-06-04 |
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