CN102504223A - Polyether ester polyhydric alcohol and using method thereof - Google Patents
Polyether ester polyhydric alcohol and using method thereof Download PDFInfo
- Publication number
- CN102504223A CN102504223A CN201110330803XA CN201110330803A CN102504223A CN 102504223 A CN102504223 A CN 102504223A CN 201110330803X A CN201110330803X A CN 201110330803XA CN 201110330803 A CN201110330803 A CN 201110330803A CN 102504223 A CN102504223 A CN 102504223A
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- CN
- China
- Prior art keywords
- polyester ether
- ether polylol
- acid
- polyhydric alcohol
- 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
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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)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention belongs to the technical field of chemical synthesis, and in particular relates to polyether ester polyhydric alcohol and a using method thereof. Epoxypropane polyether polyhydric alcohol with the molecular weight of 400-1,000, diacid and small molecular dihydric alcohol are subjected to condensation under certain conditions to form the polyether ester polyhydric alcohol with the molecular weight of 1,000-2,000. The new polyether ester polyhydric alcohol prepared by the method contains ester keys and ether keys, is blocked by primary hydroxyl groups, and has high reaction activity. Polyurethane elastomer products synthesized by using the polyether ester polyhydric alcohol have the characteristic of excellent mechanical properties of polyester polyurethane products, and also have the characteristic of excellent hydrolysis resistance of polyether polyurethane products.
Description
Technical field
The invention belongs to technical field of chemical synthesis, be specifically related to a kind of polyester ether polylol and method of use thereof.
Background technology
Polyurethane elastomer is a kind of high molecular synthetic material between plastics and rubber, has performances such as good wear resistance, good mechanical intensity and oil resistant, low temperature resistant, anti-ozone ageing, thereby is widely used in fields such as rubber roll, oil sealing, doughnut.Polyurethane elastomer is divided into polyester type and polyether-type by the difference of used polyvalent alcohol raw material; Two types The PU products respectively has relative merits; The PAUR elastomerics has excellent mechanical property like tensile strength, tear strength and oil resistance etc.; But because the high influence of ester bond in its structure, the anti-hydrolytic performance of goods is poor; The polyether(poly)urethane elastomerics has the characteristic of ehter bond in the molecule, and anti-hydrolytic performance is good, but mechanical property is poor.Therefore people urgently hope that the polyvalent alcohol that obtains a kind of both advantages prepares polyurethane elastomer.
Summary of the invention
The preparation method and the method for use that the purpose of this invention is to provide a kind of polyester ether polylol; Can prepare a kind of polyester ether polylol and obtain base polyurethane prepolymer for use as and be used for the polyurethane elastomer making with this; Its polyurethane elastomer mechanical property is excellent, and anti-hydrolytic performance obviously improves.
Polyester ether polylol of the present invention is obtained by following preparation method: by weight percentage, and diprotic acid 22.4～53.6%, polyether glycol 20～66.6% and small molecules divalent alcohol 11～26.4%, extra catalyst tetrabutyl titanate 50ppm; Add in the reaction kettle and heat, and logical nitrogen protection, reaction water outlet when temperature rises to 140 ℃; Control reflux tower tower top temperature slowly rises to 160～180 ℃ with the still temperature then at 100～102 ℃, is incubated 2～3 hours; Again temperature is risen to 220～230 ℃, after water outlet finishes, be incubated 2 hours; Adopt nitrogen bubble technology to deviate from the moisture that polycondensation produces then, the acid number of material is less than 0.6mgKOH/g in still, and moisture content is 0.05% when following; Be qualified products, begin the blowing of lowering the temperature, obtain polyester ether polylol.
Wherein, diprotic acid is preferably hexanodioic acid, Succinic Acid, terephthalic acid or phthalic anhydride, is preferably hexanodioic acid or Succinic Acid again, more preferably hexanodioic acid.
The small molecules divalent alcohol is preferably one or more in terepthaloyl moietie, butyleneglycol, Ucar 35 or the glycol ether.
Polyether glycol is preferably functionality 2～3, and number-average molecular weight is at 400～1000 polypropyleneoxide ethoxylated polyhydric alcohol.
The number-average molecular weight of synthetic polyester ether polylol of the present invention is between 1000～2000.This polyester ether polylol not only contains ester bond but also have ehter bond, and the polyester ether polylol that is obtained by this method simultaneously all is to have primary hydroxyl end capped, has high reactive behavior.
The method of use of polyester ether polylol of the present invention; By weight percentage, polyester ether polylol 77.2～83.4% and vulcabond 16.6～22.8% are mixed, reaction is 3 hours under 75～85 ℃ of conditions; The vacuum removal bubble; The isocyano-content that detects performed polymer with Di-n-Butyl Amine and hydrochloric acid soln volumetry obtains base polyurethane prepolymer for use as 4.5%, and base polyurethane prepolymer for use as and aromatic diamines solidifying agent prepare the polyurethane elastomer goods.Wherein, base polyurethane prepolymer for use as and aromatic diamines solidifying agent are to adopt known technology to prepare the polyurethane elastomer goods.Vulcabond is preferably used one or more among TDI-80, TDI-100, MDI-50 or the MDI-100.
The polyurethane elastomer goods that the present invention uses polyester ether polylol to make can be used to make polyurethane rubber roller, urethane castor, polyurethane sieve plate and polyurethane cyclone.
The invention has the advantages that: the polyester ether polylol for preparing not only contains ester bond but also have ehter bond, and the primary hydroxyl end-blocking is arranged again, has high reactive behavior.Both had the excellent characteristic of PAUR product mechanical property by this polyester ether polylol synthetic The PU products, also had the characteristic of polyether(poly)urethane elastomer product excellent hydrolysis resistance.
Embodiment
Below in conjunction with embodiment the present invention is further specified.
The embodiment material therefor is following:
DL-1000: the polypropyleneoxide ether divalent alcohol of number-average molecular weight 1000
DL-400: the polypropyleneoxide ether divalent alcohol of number-average molecular weight 400
MN-500: the polypropyleneoxide ether trivalent alcohol of average molecular weight 500
ODX-150: the polyester diol of number-average molecular weight 1500
AA: hexanodioic acid
DEG: glycol ether
EG: terepthaloyl moietie
TDI-80: contain 2 of 80% 2,4 toluene diisocyanate and 20%, the 6-tolylene diisocyanate
TDI-100:2, the 4-toluene diisocyanate content is greater than 97.5%
MDI-100:4,4 '-diphenylmethanediisocyanate
MDI-50:2,4 '-diphenylmethanediisocyanate 50% and 4,4 '-diphenylmethanediisocyanate 50%
MOCA:3,3 '-two chloro-4,4 '-diaminodiphenyl-methane.
Embodiment 1:
The preparation of polyester ether polylol: according to the weight percentage meter, be 1000 polyether glycol (DL-1000) 66.6%, terepthaloyl moietie (EG) 11%, hexanodioic acid (AA) 22.4% with molecular weight, extra catalyst tetrabutyl titanate 50ppm; Add in the reaction kettle and heat, and logical nitrogen protection, reaction water outlet when temperature rises to 140 ℃; Control reflux tower tower top temperature slowly rises to 160 ℃ with the still temperature then at 100 ℃, is incubated 3 hours; Temperature is risen to 230 ℃, after water outlet finishes, be incubated 2 hours; Adopt nitrogen bubble technology to deviate from the moisture that polycondensation produces then, when the acid number of polyester ether polylol less than 0.6mgKOH/g, moisture content is 0.05% when following; Qualified products begins the blowing of lowering the temperature, and obtains the polyester ether polylol of number-average molecular weight 1500.
The use of polyester ether polylol: according to the weight percentage meter; Get the polyester ether polylol 81.2% of above preparation, add vulcabond (TDI-100) 18.8%, 80 ℃ of reactions 3 hours; The vacuum removal bubble; Sampling detects isocyanate content, and detection-NCO content obtains base polyurethane prepolymer for use as 4.5%.By it can and MOCA, adopt the known technology of the public, produce the The PU products of hardness at Shao Shi 90A.
Embodiment 2:
The preparation of polyester ether polylol: according to the weight percentage meter, be 400 polyether glycol (DL-400) 26.7%, terepthaloyl moietie (EG) 24.2%, hexanodioic acid (AA) 49.1% with molecular weight, extra catalyst tetrabutyl titanate 50ppm; Add in the reaction kettle and heat, and logical nitrogen protection, reaction water outlet when temperature rises to 140 ℃; Control reflux tower tower top temperature slowly rises to 180 ℃ with the still temperature then at 102 ℃, is incubated 2 hours; Temperature is risen to 220 ℃ ℃, after water outlet finishes, be incubated 2 hours; Adopt nitrogen bubble technology to deviate from the moisture that polycondensation produces then, when the acid number of polyester ether polylol less than 0.6mgKOH/g, moisture content is 0.05% when following; Qualified products begins the blowing of lowering the temperature, and obtains the polyester ether polylol of number-average molecular weight 1000.
The use of polyester ether polylol: according to the weight percentage meter; Get the polyester ether polylol 77.2% of above preparation, add vulcabond (TDI-100) 22.8%, 80 ℃ of reactions 3 hours; The vacuum removal bubble; Sampling detects isocyanate content, and detection-NCO content obtains base polyurethane prepolymer for use as 4.5%.By it can and MOCA, adopt the known technology of the public, produce the The PU products of hardness at Shao Shi 92A.
Embodiment 3:
The preparation of polyester ether polylol: according to the weight percentage meter, be 400 polyether glycol (DL-400) 20%, glycol ether (DEG) 26.4%, hexanodioic acid (AA) 53.6% with molecular weight, extra catalyst tetrabutyl titanate 50ppm; Add in the reaction kettle and heat, and logical nitrogen protection, reaction water outlet when temperature rises to 140 ℃; Control reflux tower tower top temperature slowly rises to 180 ℃ with the still temperature then at 100 ℃, is incubated 2 hours; Temperature is risen to 220 ℃, after water outlet finishes, be incubated 2 hours; Adopt nitrogen bubble technology to deviate from the moisture that polycondensation produces then, when the acid number of polyester ether polylol less than 0.6mgKOH/g, moisture content is 0.05% when following; Qualified products begins the blowing of lowering the temperature, and obtains the polyester ether polylol of number-average molecular weight 2000.
The use of polyester ether polylol: according to the weight percentage meter; Get the polyester ether polylol 83.4% of above preparation, add vulcabond (TDI-100) 16.6%, 80 ℃ of reactions 3 hours; The vacuum removal bubble; Sampling detects isocyanate content, and detection-NCO content obtains base polyurethane prepolymer for use as 4.5%.By it can and MOCA, adopt the known technology of the public, produce the The PU products of hardness at Shao Shi 88A.
Comparative Examples 1:
According to the weight percentage meter, the polyester diol of number-average molecular weight 1500 (ODX-150) 81.2% adds vulcabond (TDI-100) 18.8%; 80 ℃ of reactions 3 hours, the vacuum removal bubble, sampling detects isocyanate content; Detection-NCO content obtains base polyurethane prepolymer for use as 4.5%.By it can and MOCA, adopt the known technology of the public, produce the The PU products of hardness at Shao Shi 93A.
The performance test results of test piece in embodiment and the Comparative Examples, it is following specifically to detect data:
| Project | Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparison example 1 |
| Hardness (Shao 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 |
Claims (9)
1. polyester ether polylol is characterized in that being obtained by following preparation method: by weight percentage, and diprotic acid 22.4～53.6%, polyether glycol 20～66.6% and small molecules divalent alcohol 11～26.4%, extra catalyst tetrabutyl titanate 50ppm; Add in the reaction kettle and heat, and logical nitrogen protection, reaction water outlet when temperature rises to 140 ℃; Control reflux tower tower top temperature slowly rises to 160～180 ℃ with the still temperature then at 100～102 ℃, is incubated 2～3 hours; Again temperature is risen to 220～230 ℃, after water outlet finishes, be incubated 2 hours; Adopt nitrogen bubble technology to deviate from the moisture that polycondensation produces then, the acid number of material is less than 0.6mgKOH/g in still, and moisture content is 0.05% when following; Be qualified products, begin the blowing of lowering the temperature, obtain polyester ether polylol.
2. polyester ether polylol according to claim 1 is characterized in that diprotic acid is hexanodioic acid, Succinic Acid, terephthalic acid or phthalic anhydride.
3. polyester ether polylol according to claim 2 is characterized in that diprotic acid is hexanodioic acid or Succinic Acid.
4. polyester ether polylol according to claim 3 is characterized in that diprotic acid is a hexanodioic acid.
5. polyester ether polylol according to claim 1 is characterized in that the small molecules divalent alcohol is one or more in terepthaloyl moietie, butyleneglycol, Ucar 35 or the glycol ether.
6. polyester ether polylol according to claim 1 is characterized in that polyether glycol is a functionality 2～3, and number-average molecular weight is at 400～1000 polypropyleneoxide ethoxylated polyhydric alcohol.
7. the method for use of the described polyester ether polylol of claim 1; It is characterized in that by weight percentage; Polyester ether polylol 77.2～83.4% and vulcabond 16.6～22.8% are mixed, and reaction is 3 hours under 75～85 ℃ of conditions, the vacuum removal bubble; Obtain base polyurethane prepolymer for use as, base polyurethane prepolymer for use as and aromatic diamines solidifying agent prepare the polyurethane elastomer goods.
8. the method for use of polyester ether polylol according to claim 7 is characterized in that vulcabond selects one or more among TDI-80, TDI-100, MDI-50 or the MDI-100 for use.
9. the method for use of polyester ether polylol according to claim 7 is characterized in that the polyurethane elastomer goods are used to make polyurethane rubber roller, urethane castor, polyurethane sieve plate and polyurethane cyclone.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110330803XA CN102504223A (en) | 2011-10-27 | 2011-10-27 | Polyether ester polyhydric alcohol and using method thereof |
| MYPI2013701709A MY165489A (en) | 2011-10-27 | 2012-03-19 | Polyether-ester Polyol and Usage Thereof |
| BR112013026722A BR112013026722A2 (en) | 2011-10-27 | 2012-03-19 | polyether polyether ester and its use |
| AU2012327771A AU2012327771B2 (en) | 2011-10-27 | 2012-03-19 | Polyether-ester polyol and usage thereof |
| PCT/CN2012/000342 WO2013060089A1 (en) | 2011-10-27 | 2012-03-19 | Polyether-ester polyol and usage thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110330803XA CN102504223A (en) | 2011-10-27 | 2011-10-27 | Polyether ester polyhydric alcohol and using method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102504223A true CN102504223A (en) | 2012-06-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110330803XA Pending CN102504223A (en) | 2011-10-27 | 2011-10-27 | Polyether ester polyhydric alcohol and using method 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) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013060089A1 (en) * | 2011-10-27 | 2013-05-02 | 山东东大一诺威聚氨酯有限公司 | Polyether-ester polyol and usage 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 |
| CN104945593A (en) * | 2015-05-13 | 2015-09-30 | 吕涛 | Preparation method of film-grade TPU slice |
| 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 |
| CN106750233A (en) * | 2017-01-16 | 2017-05-31 | 美瑞新材料股份有限公司 | A kind of preparation technology of makrolon ethoxylated polyhydric alcohol and the polyurethane elastomer of oil resistant low temperature resistant |
| CN107573475A (en) * | 2017-09-15 | 2018-01-12 | 山东诺威聚氨酯股份有限公司 | Urethane composition for making solid football ball and its preparation method and application |
| CN108148536A (en) * | 2017-12-20 | 2018-06-12 | 上海康达化工新材料股份有限公司 | A kind of media-resistant polyurethane laminating adhesive and its preparation method and application |
| CN108285524A (en) * | 2017-12-29 | 2018-07-17 | 浙江华峰新材料股份有限公司 | On-slip type polyurethane elastomer stoste and its preparation method and application |
| 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 |
| CN110387032A (en) * | 2019-07-25 | 2019-10-29 | 万华化学集团股份有限公司 | A kind of polyester ether polylol, preparation method and its polyurethane elastomer of preparation |
| CN110511346A (en) * | 2019-09-16 | 2019-11-29 | 嘉兴学院 | A kind of polyurethane and its preparation method and application based on polyester ether polylol |
| CN112142880A (en) * | 2020-10-14 | 2020-12-29 | 长华化学科技股份有限公司 | Continuous purification method of polymer polyol |
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| WO2024164834A1 (en) * | 2023-02-09 | 2024-08-15 | 郑州中远氨纶工程技术有限公司 | Polyether ester polyol, preparation method therefor, and method for preparing polyurethane elastomer by using polyether ester polyol |
| WO2024164835A1 (en) * | 2023-02-09 | 2024-08-15 | 郑州中远氨纶工程技术有限公司 | Polyether ester polyol, preparation method therefor, and method for using same to prepare polyurethane elastomer |
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- 2012-03-19 AU AU2012327771A patent/AU2012327771B2/en not_active Ceased
- 2012-03-19 BR BR112013026722A patent/BR112013026722A2/en not_active Application Discontinuation
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| WO2013060089A1 (en) * | 2011-10-27 | 2013-05-02 | 山东东大一诺威聚氨酯有限公司 | Polyether-ester polyol and usage 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 |
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| CN104945593B (en) * | 2015-05-13 | 2017-12-29 | 吕涛 | A kind of preparation method of film-grade TPU sections |
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| WO2023078419A1 (en) * | 2021-11-05 | 2023-05-11 | 广州黑格智造信息科技有限公司 | Polyurethane acrylate, photocurable material, preparation method and use |
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| WO2024164834A1 (en) * | 2023-02-09 | 2024-08-15 | 郑州中远氨纶工程技术有限公司 | Polyether ester polyol, preparation method therefor, and method for preparing polyurethane elastomer by using polyether ester polyol |
| WO2024164835A1 (en) * | 2023-02-09 | 2024-08-15 | 郑州中远氨纶工程技术有限公司 | Polyether ester polyol, preparation method therefor, and method for using same to prepare polyurethane elastomer |
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Also Published As
| Publication number | Publication date |
|---|---|
| BR112013026722A2 (en) | 2019-07-09 |
| AU2012327771B2 (en) | 2015-08-20 |
| WO2013060089A1 (en) | 2013-05-02 |
| MY165489A (en) | 2018-03-23 |
| AU2012327771A1 (en) | 2013-09-19 |
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