AU2012327771B2 - Polyether-ester polyol and usage thereof - Google Patents
Polyether-ester polyol and usage thereof Download PDFInfo
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- AU2012327771B2 AU2012327771B2 AU2012327771A AU2012327771A AU2012327771B2 AU 2012327771 B2 AU2012327771 B2 AU 2012327771B2 AU 2012327771 A AU2012327771 A AU 2012327771A AU 2012327771 A AU2012327771 A AU 2012327771A AU 2012327771 B2 AU2012327771 B2 AU 2012327771B2
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- Australia
- Prior art keywords
- polyether
- temperature
- ester polyol
- mixture
- polyurethane
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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
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
Abstract
Disclosed are a polyether-ester polyol and usage thereof. The polyether-ester polyol having a molecular-weight of 1000-2000is prepared by a condensation reaction of a polypropylene-oxide polyether polyol having a molecular-weight of 400-1000, a dibasic acid and a low-molecular diol under a certain reaction condition. The polyether-ester polyol thus prepared is mixed with a diisocyanate and reacted under a temperature range of from 75 to 85℃ for three hours, then the air bubbles are removed from the mixture under vacuum to obtain a polyurethane prepolymer. A polyurethane elastomeric article is produce by the reaction of the polyurethane prepolymer and an aromatic diamine curing agent. The polyether-ester polyol thus produced has ester bonds and also ether bonds and is terminated by primary hydroxyl group, so has a high reactivity. The polyurethane elastomeric article made from the polyether-ester polyol has both the excellent mechanical properties of polyester polyurethane product and the excellent hydrolysis-resistance properties of polyether polyurethane product.
Description
1 SPECIFICAON Title- Polyether-ester Polyol and Usage Thereof TECHNICAL FIELD The present invention is under the catalog of chemical synthesis technology. It 5 involves a Polyether-ester polyol and usage thereof. BACKGROUND ART Polyurethane elastomer is a polymer composite material between plastic and rubber. It has excellent abrasion resistance, good mechanical strength, oil resistance, low temperature resistance, resistance to ozone aging and other properties, and thus is 10 widely used in rubber rollers, oil seals, automobile tires and other fields. The polyurethane elastomer is divided into two types: the Polyester type and polyether type, as a result of different polyol raw material used. Both types of polyurethane elastomer products have their own advantages and disadvantages. The polyester--based polyurethane elastomer has excellent mechanical properties, such as: tensile strength, 15 tear strength and oil resistance, etc. But due to the impact of high ester bond in its structure, its hydrolysis resistance is relatively low. The polyether type polyuiethane elastomer has an ether bond in the molecule and thus has a good hydrolysis resistance. But the mechanical properties are relatively poor. Therefore, people are eager to get a polyol with both types of advantages to prepare polyurethane elastomers. 20 SUMMARY OF THE INVENTION The present invention provides a polyether ester polyol preparation method and a use method. The aim of the present invention is to prepare and obtain a polyether ester polyol and further obtain the polyurethane prepolymers used to prepare the polyurethane elastomer. The polyurethane elastomer can have excellent mechanical 25 properties and its hydrolysis resistance can also be significantly improved. Accordingly, the present invention provides a polyether-ester polyol, obtained by performing the following steps: in weight percent, preparing a mixture containing from 22.4 to 536% dibasic acid, from 20 to 66.6% polyether polyol, from I1 to 264.4% smallnolecule diol, and 30 50 ppm tetrabutyl titanate catalyst; heating the mixture under nitrogen atmosphere to 140'C to separate moisture, the heating being performed using a reaction vessel provided with a reflux column; adjusting the temperature at a top portion of the reflux colurm to a temperature of from 100 to 102cC; 35 increasing the temperature in the reaction vessel to a temperature of from 160 to 1804C and maintaining said temperature for 2 to 3 hours; further increasing the temperature in the reaction vessel to a temperature of from 2 220 to 230'C to further separate moisture, and maintaining said temperature for 2 to 3 hours to obtain a polycondensation mixture; and dehydrating the polycondensation mixture by bubbling nitrogen through the mixture until the acid value of the polycondensation mixture is less than 0.6 5 mgKOH/g and the moisture content is below 0,05% by weight to obtain the polyether-ester polyol. The dicarboxylic acid is preferably adipic acid, succinic acid, terephthalic acid or phthalic anhydride, more preferably adipic acid or succinic acid, and even more preferably adipic acid. 10 The small molecule dihydric alcohol is preferably one or more types of the ethylene glycol, butylene glycol, propylene glycol or diethylene glycol. The polyether polyol is preferably a polypropyleneoxide polyol with a functionality of 2~3 and with a number average molecular weight of 400~ 1000. The polyether ester polyol synthesized in the present invention has a number 15 average molecular weight in the range of 1000-2000; The polyether ester polyol contains both the ester bond and the ether bond. The polyether-ester polyol obtained by this method is end-capped with primary hydroxyl, It has a high reactivity. The present invention also provides use of a polyetber-ester polyol according any one of claims I to 6 in a method of synthesizing polyurethane elastomer, the method 20 comprising: in weight percent, preparing a mixture containing from. '7.2 to 83.4% of the polyether-ester polyol and from 16.6 to 22.8% diisocyanate; reacting the mixture for 3 hours at a temperature of from 75 to 85OC; removing air bubbles from the reacted mixture under vacuum to obtain a 25 polyurethane prepolymer; and reacting the polyurethane prepolymer and an aromatic diamine curing agent to obtain the polyurethane elastomer. The diisocyanate is preferably one or more types of TDI-80, TDI-100, MD-50 or MDI- 100. The polyurethane elastomer products obtained from the polyether ester polyo! in 30 the present invention can be used to produce polyurethane rubber roller, polyurethane casters, polyurethane sieve and polyurethane swirled Also, the present provides a method of producing polyether-ester polyol, comprising the following steps: in weight percent, preparing a mixture containing from 22.4 to 53.6% dibasic 35 acid, from 20 to 66.6% polyether polyol, from II to 26.4% small molecule diol, and 50 ppm tetrabutyl, titanate catalyst; heating the mixture under nitrogen atmosphere to 140 0 C to separate moisture, the 2A heating being performed using a reaction vessel provided with a reflux column; adjusting the temperature at a top portion of the reflux column to a temperature of from 100 to 102'C; increasing the temperature in the reaction vessel to a temperature of from 160 to 5 1801C and maintaining said temperature for 2 to 3 hours; further increasing the temperature in the reaction vessel to a temperature of from 220 to 2301C to further separate moisture, and maintaining said temperature for 2 to 3 hours to obtain a polycondensation mixture; and dehydrating the polycondensation mixture by bubbling nitrogen through the 10 mixture until the acid value of the polycondensation mixture is less than 0.6 mgKOH/g and the moisture content is below 0.05% by weight to obtain the polyether-ester polyol. The beneficial effects of the present invention are in that: the polyether-ester polyol prepared contains both the ester bond and the ether bond and is primary 15 hydroxyl-capped with a high reactivity. The polyurethane elastomer synthesized from the polyether ester polyol has both the excellent mechanical properties of the polyester polyurethane products and excellent hydrolysis resistance characteristics of the polyether polyurethane products. BEST MODE FOR CARRYING OUT THE INVENTION 20 The following examples further illustrate the present invention. Materials used are as follows: DL-1000: polypropylene oxide ether diol, with a number average molecular weight of 1000 DL-400: polypropylene oxide ether diol, with a number average molecular 25 weight of 400 MN-500: polypropylene oxide ether triol, with a number average molecular weight of 500 H:\kxg\Interwoven\NRPortbl\DCC\KXG\5424878_2.doc - 19/09/13 -3 ODX-150: polyester diol, with a number average molecular weight of 1500 AA: adipic acid DEG: diethylene glycol EG: ethylene glycol 5 TDI-80: containing 80% of 2,4 - tolylene isocyanate ester and 20% of 2,6 toluene diisocyanate TDI-100: 2,4 - toluene diisocyanate content being greater than 97.5% MDI-100: 4,4 '- diphenyl methane diisocyanate MDI-50: 50% of 2, 4' - diphenylmethane diisocyanate and 50% of 4, 4 10 diphenyl methane diisocyanate ester MOCA: 3,3 '- dichloro-4, 4'- diaminodiphenyl methane Example 1: Preparation of the polyetherester polyol: in weight percent, take 66.6% of the polyether polyol with a molecular weight of 1000 (DL-1000), 11% of the ethylene 15 glycol (EG), 22.4% of the adipic acid (AA), plus the catalyst tetrabutyltitanate 50ppm. Heat the mixture in the reaction kettle with nitrogen protection. Raise the temperature to 140"C and precipitate the moisture. Control the reflux column top temperature at 100 C.Slowly increase the kettle temperature to 160'C. Maintain the temperature for 3 hours.Again increase the kettle temperature to 230 "C and 20 precipitate all moisture. Maintain the temperature for 2 hours. Dehydrate the polycondensation mixture through the nitrogen bubbling process. When the acid value of the polyether polyol is less than 0.6 mgKOH/g and the moisture content is below 0.05%, the product is qualified. Cool the discharge the product.Thus obtain the polyether ester polyol with a number average molecular weight of 1500. 25 Use of the polyetherester polyol: in weight percent, take 81.2% of the polyether ester polyol prepared above. Add 18.8% of the diisocyanate (TDI-100). Maintain reaction for 3 hours at 80 *C. Remove the air bubbles in vacuum. Sample the product to detect the isocyanate content. The polyurethane prepolymer is obtained when the -NCO content of 4.5% is detected. The polyurethane prepolymer and MOCA, through 30 a publicly known process, can be used to prepare the polyurethane elastomer with a hardness of Shore 90A. Example 2: Preparation of the polyetherester polyol: in weight percent, take 26.7% of the polyether polyol with a molecular weight of 400 (DL-400), 24.2% of the ethylene 35 glycol (EG), 49.1% of the adipic acid (AA), plus the catalyst tetrabutyltitanate 50ppm. Heat the mixture in the reaction kettle with nitrogen protection. Raise the temperature to 140 C and precipitate the moisture. Control the reflux column top temperature at 102'C.Slowly increase the kettle temperature to 180 C. Maintain the H:\kxg\Intenvoven\NRPortbl\DCC\KXG\5424878_2.doc - 19/09/13 -4 temperature for 2 hours.Again increase the kettle temperature to 220 'C and precipitate all moisture. Maintain the temperature for 2 hours. Dehydrate the polycondensation mixture through the nitrogen bubbling process. When the acid value of the polyether polyol is less than 0.6 mgKOH/g and the moisture content is below 5 0.05%, the product is qualified. Cool the discharge the product.Thus obtain the polyether ester polyol with a number average molecular weight of 1000. Use of the polyetherester polyol: in weight percent, take 77.2% of the polyether ester polyol prepared above. Add 22.8% of the diisocyanate (TDI-100). Maintain reaction for 3 hours at 80 "C. Remove the air bubbles in vacuum. Sample the product 10 to detect the isocyanate content. The polyurethane prepolymer is obtained when the -NCO content of 4.5% is detected. The polyurethane prepolymer and MOCA, through a publicly known process, can be used to prepare the polyurethane elastomer with a hardness of Shore 92A. Example 3: 15 Preparation of the polyetherester polyol: in weight percent, take 20% of the polyether polyol with a molecular weight of 400 (DL-400), 26.4% of the diethylene glycol (DEG), 53.6% of the adipic acid (AA), plus the catalyst tetrabutyltitanate 50ppm. Heat the mixture in the reaction kettle with nitrogen protection. Raise the temperature to 140 C and precipitate the moisture. Control the reflux column top 20 temperature at 100 C.Slowly increase the kettle temperature to 180 C. Maintain the temperature for 2 hours.Again increase the kettle temperature to 220 0 C and precipitate all moisture. Maintain the temperature for 2 hours. Dehydrate the polycondensation mixture through the nitrogen bubbling process. When the acid value of the polyether polyol is less than 0.6 mgKOH/g and the moisture content is below 25 0.05%, the product is qualified. Cool the discharge the product.Thus obtain the polyether ester polyol with a number average molecular weight of 2000. Use of the polyetherester polyol: in weight percent, take 83.4% of the polyether ester polyol prepared above. Add 16.6% of the diisocyanate (TDI-100). Maintain reaction for 3 hours at 80 'C. Remove the air bubbles in vacuum. Sample the product 30 to detect the isocyanate content. The polyurethane prepolymer is obtained when the -NCO content of 4.5% is detected. The polyurethane prepolymer and MOCA, through a publicly known process, can be used to prepare the polyurethane elastomer with a hardness of Shore 88A. Comparative Example 1: 35 In weight percent, take 81.2% of the polyeaster diol (ODX-150) with a number average molecular weight of 1500. Add 18.8% of the diisocyanate (TDI-100). Maintain reaction for 3 hours at 80 'C. Remove the air bubbles in vacuum.Sample the product to detect the isocyanate content. The polyurethane prepolymer is obtained when the -NCO content of 4.5% is detected. The polyurethane prepolymer and 40 MOCA, through a publicly known process, can be used to prepare the polyurethane elastomer with a hardness of Shore 93A.
5 The performance test results of the Examples and the test piece of the Comparative Example are shown in the following table. Comparative Item Example 1 Example 2 Example 3 lExample I Hardness (Shore A) 90 92 88 93 Tensile strength (Mpa) 47.0 50.9 48,5 52,2 Elongation % 800 780 800 750 Tear strength (KN/m) 85.3 88.1 85.1 90.2 Hardness (Shore A) 90 92 88 93 Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and 5 "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as 10 an acknowledgment or admission or any forn of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.
Claims (10)
1. A polyether-ester polyol, obtained by perfonning the following steps: in weight percent, preparing a mixture containing from 22.4 to 53.6% dibasic acid, from 20 to 66.6% polyether polyol, from 11 to 26.4% small molecule diol, and 50 ppm tetrabutyl titanate catalyst; heating the mixture under nitrogen atmosphere to 140'C to separate moisture, the heating being performed using a reaction vessel provided with a reflux column; adjusting the temperature at a top portion of the reflux column to a temperature of from 100 to 102*C; increasing the temperature in the reaction vessel to a temperature of from 160 to 180'C and maintaining said temperature for 2 to 3 hours; further increasing the temperature in the reaction vessel to a temperature of from 220 to 2301C to further separate moisture, and maintaining said temperature for 2 to 3 hours to obtain a polycondensation mixture; and dehydrating the polycondensation mixture by bubbling nitrogen through the mixture until the acid value of the polycondensation mixture is less than 0.6 mgKOH/g and the moisture content is below 0.05% by weight to obtain the polyether-ester polyol.
2. The polyether-ester polyol according to claim 1, wherein the dibasic acid is selected from adipic acid, succinic acid, and terephthalic acid.
3, The polyether-ester polyol according to claim I or 2, wherein the dibasic acid is selected from adipic acid and succinic acid.
4. The polyether-ester polyol according to any one of claims I to 3, wherein the dibasic acid is adipic acid.
5 The polyether-ester polyol according to any one of clainis I to 4, wherein the small 7 molecule diol is selected from butylene glycol, propylene glycol, diethylene glycol, and combinations thereof
6. The polyether-ester polyol according to any one of claims 1 to 5, wherein the polyether polyol is polypropylene oxide ether polyol with a functionality of 2 to 3 and with a number average molecular weight of from 400 to 1000.
7. Use of a polyether-ester polyol according any one of claims 1 to 6 in a method of synthesizing polyurethane elastomer, the method comprising: in weight percent, preparing a mixture containing from 77.2 to 83.4% of the polyether-ester polyol and from 16.6 to 22.8% diisocyanate; reacting the mixture for 3 hours at a temperature of from 75 to 85 0 C; removing air bubbles from the reacted mixture under vacuum to obtain a polyurethane prepolymer; and reacting the polyurethane prepolymer and an aromatic diamine curing agent to obtain the polyurethane elastomer.
8. The use according to claim 7, wherein the diisocyanate is selected from TDI-O, TDI-100, MDI-50, MDL- 100, and combinations thereof
9. Use of the polyurethane elastomer obtained by the method defined in claim 7 or 8 to produce a polyurethane rubber roller, polyurethane casters, a polyurethane sieve or a polyurethane swirler.
10. A method of producing polyether-ester polyol, comprising the following steps: in weight percent, preparing a mixture containing from 22.4 to 53.6% dibasic acid, from 20 to 66,6% polyether polyol, from 11 to 26.4% sniall molecule diol, and 50 ppm tetrabutyl titanate catalyst; heating the mixture under nitrogen atmosphere to 140*C to separate moisture, the heating being performed using a reaction vessel provided with a reflux column; 8 adjusting the temperature at a top portion of the reflux colIumin to a temperature of from 100 to 102'C; increasing the temperature in the reaction vessel to a temperature of from 160 to 180"C and maintaining said temperature for 2 to 3 hours; further increasing the temperature in the reaction vessel to a temperature of from 220 to 230'C to further separate moisture, and maintaining said temperature for 2 to 3 hours to obtain a polycondensation mixture; and dehydrating the polycondensation mixture by bubbling nitrogen through the mixture until the acid value of the polycondensation mixture is less than 0.6 mgKOH/g and the moisture content is below 0.05% by weight to obtain the polyether-ester polyol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110330803.X | 2011-10-27 | ||
| CN201110330803XA CN102504223A (en) | 2011-10-27 | 2011-10-27 | Polyether ester polyhydric alcohol and using method thereof |
| PCT/CN2012/000342 WO2013060089A1 (en) | 2011-10-27 | 2012-03-19 | Polyether-ester polyol and usage thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2012327771A1 AU2012327771A1 (en) | 2013-09-19 |
| AU2012327771B2 true AU2012327771B2 (en) | 2015-08-20 |
Family
ID=46216362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012327771A Ceased AU2012327771B2 (en) | 2011-10-27 | 2012-03-19 | Polyether-ester polyol and usage thereof |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN102504223A (en) |
| AU (1) | AU2012327771B2 (en) |
| BR (1) | BR112013026722A2 (en) |
| MY (1) | MY165489A (en) |
| WO (1) | WO2013060089A1 (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504223A (en) * | 2011-10-27 | 2012-06-20 | 山东东大一诺威聚氨酯有限公司 | Polyether ester polyhydric alcohol and using method thereof |
| CN103642019A (en) * | 2013-11-21 | 2014-03-19 | 金发科技股份有限公司 | High resilience polyester elastomer and preparation method thereof |
| CN104945593B (en) * | 2015-05-13 | 2017-12-29 | 吕涛 | A kind of preparation method of film-grade TPU sections |
| JP2017145275A (en) * | 2016-02-15 | 2017-08-24 | 株式会社Adeka | Modifier for resin, resin composition, and film using the same |
| CN105732967A (en) * | 2016-03-07 | 2016-07-06 | 美瑞新材料股份有限公司 | Method for preparing thermoplastic copolyester elastomer by using chain extension method |
| CN106167543A (en) * | 2016-08-11 | 2016-11-30 | 安徽龙川橡塑科技有限公司 | A kind of production technology of fine mesh polyurethane screen |
| CN106750233B (en) * | 2017-01-16 | 2018-11-23 | 美瑞新材料股份有限公司 | A kind of preparation process of polycarbonate-ethoxylated polyhydric alcohol and the polyurethane elastomer of oil resistant low temperature resistant |
| CN107573475B (en) * | 2017-09-15 | 2020-11-24 | 山东一诺威聚氨酯股份有限公司 | Polyurethane composition for manufacturing solid football and preparation method and application thereof |
| CN108148536B (en) * | 2017-12-20 | 2021-03-19 | 上海康达化工新材料集团股份有限公司 | Medium-resistant polyurethane laminating adhesive and preparation method and application thereof |
| CN108285524B (en) * | 2017-12-29 | 2021-10-01 | 浙江华峰新材料有限公司 | Anti-slip polyurethane elastomer stock solution and preparation method and application thereof |
| CN108467480A (en) * | 2018-03-22 | 2018-08-31 | 上海联景高分子材料有限公司 | Polyether-modified polyester polyol and its thermoplastic polyurethane elastomer being polymerized |
| CN110387032B (en) * | 2019-07-25 | 2021-07-23 | 万华化学集团股份有限公司 | Polyether ester polyol, preparation method thereof and polyurethane elastomer prepared from polyether ester polyol |
| CN110511346B (en) * | 2019-09-16 | 2022-01-25 | 嘉兴学院 | Polyurethane based on polyether ester polyol and preparation method and application thereof |
| CN112142880B (en) * | 2020-10-14 | 2022-07-01 | 长华化学科技股份有限公司 | Continuous purification method of polymer polyol |
| CN115246925A (en) * | 2021-09-26 | 2022-10-28 | 佳化化学科技发展（上海）有限公司 | Polyether ester and preparation method and application thereof |
| CN113980230B (en) * | 2021-11-01 | 2023-06-02 | 山东一诺威聚氨酯股份有限公司 | Moisture-heat resistant thermoplastic polyurethane elastomer material and preparation method thereof |
| CN114057975B (en) * | 2021-11-05 | 2023-03-28 | 广州黑格智造信息科技有限公司 | Low-haze high-toughness polyurethane acrylate, photocuring material, and preparation methods and applications thereof |
| CN115010901A (en) * | 2022-06-17 | 2022-09-06 | 佳化化学科技发展（上海）有限公司 | Low-viscosity hydrolysis-resistant photocuring polyurethane resin and preparation method and application thereof |
| CN117487123A (en) * | 2023-12-29 | 2024-02-02 | 山东一诺威聚氨酯股份有限公司 | High-toughness high-strength polyurethane rock climbing fulcrum material and preparation method thereof |
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| US4605729A (en) * | 1984-10-17 | 1986-08-12 | Bayer Aktiengesellschaft | Process for the production of polyetherester polyols and the products and use thereof |
| US20040082677A1 (en) * | 2002-10-21 | 2004-04-29 | Erhard Michels | Polyurethane elastomers and processes for their preparation and use |
| US20050131137A1 (en) * | 2003-12-11 | 2005-06-16 | Hartmut Nefzger | Polymer dispersions in polyesterpolyols |
| US20070010593A1 (en) * | 2005-07-08 | 2007-01-11 | Bayer Materialscience Ag | Pur-polyester flexible foams based on polyetheresterpolyols |
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| EP0675147B1 (en) * | 1994-03-30 | 2001-08-22 | ARCO Chemical Technology, L.P. | Process for making a polyetherester |
| CN1281658C (en) * | 2002-09-04 | 2006-10-25 | 中纺投资发展股份有限公司 | Method for preparing polyether ester elastomer in blow molding grade |
| CN1480477A (en) * | 2002-09-04 | 2004-03-10 | 中纺投资发展股份有限公司 | High pertormance thermoplastic polyether ester elastomer with low degree of hardness and high melting point |
| CN101130597B (en) * | 2007-09-29 | 2011-06-01 | 山东东大一诺威聚氨酯有限公司 | Synthesis method of solvent resistant solvent type urethane elastomer |
| CN102504223A (en) * | 2011-10-27 | 2012-06-20 | 山东东大一诺威聚氨酯有限公司 | Polyether ester polyhydric alcohol and using method thereof |
-
2011
- 2011-10-27 CN CN201110330803XA patent/CN102504223A/en active Pending
-
2012
- 2012-03-19 MY MYPI2013701709A patent/MY165489A/en unknown
- 2012-03-19 BR BR112013026722A patent/BR112013026722A2/en not_active Application Discontinuation
- 2012-03-19 AU AU2012327771A patent/AU2012327771B2/en not_active Ceased
- 2012-03-19 WO PCT/CN2012/000342 patent/WO2013060089A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605729A (en) * | 1984-10-17 | 1986-08-12 | Bayer Aktiengesellschaft | Process for the production of polyetherester polyols and the products and use thereof |
| US20040082677A1 (en) * | 2002-10-21 | 2004-04-29 | Erhard Michels | Polyurethane elastomers and processes for their preparation and use |
| US20050131137A1 (en) * | 2003-12-11 | 2005-06-16 | Hartmut Nefzger | Polymer dispersions in polyesterpolyols |
| US20070010593A1 (en) * | 2005-07-08 | 2007-01-11 | Bayer Materialscience Ag | Pur-polyester flexible foams based on polyetheresterpolyols |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013026722A2 (en) | 2019-07-09 |
| MY165489A (en) | 2018-03-23 |
| AU2012327771A1 (en) | 2013-09-19 |
| WO2013060089A1 (en) | 2013-05-02 |
| CN102504223A (en) | 2012-06-20 |
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