CN115784849B - Synthesis method of high-melting-point alcohol propoxylate - Google Patents
Synthesis method of high-melting-point alcohol propoxylate Download PDFInfo
- Publication number
- CN115784849B CN115784849B CN202211546113.2A CN202211546113A CN115784849B CN 115784849 B CN115784849 B CN 115784849B CN 202211546113 A CN202211546113 A CN 202211546113A CN 115784849 B CN115784849 B CN 115784849B
- Authority
- CN
- China
- Prior art keywords
- reaction
- melting
- synthesizing
- initiator
- propylene oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000001308 synthesis method Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 71
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims abstract description 39
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 27
- 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 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 18
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003999 initiator Substances 0.000 claims abstract description 14
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 11
- 238000002844 melting Methods 0.000 claims abstract description 11
- 230000008018 melting Effects 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000006227 byproduct Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- -1 propylene alcohol Chemical compound 0.000 description 6
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010146 3D printing Methods 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical group [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing a high-melting-point alcohol propoxylate, belonging to the technical field of organic compound synthesis. The invention discloses a method for synthesizing a high-melting-point alcohol propoxylate, which comprises the following steps: bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol with high melting point is used as an initiator raw material, an N, N-diisopropylethylamine catalyst is added, and propylene carbonate and propylene oxide are used as reaction monomers to synthesize the propoxylate. The invention provides a synthesis method for synthesizing a propoxylate by using an N, N-diisopropylethylamine catalyst and alcohol and propylene carbonate and propylene oxide with high melting point.
Description
Technical Field
The invention relates to a method for synthesizing a high-melting-point alcohol propoxylate, belonging to the technical field of organic compound synthesis.
Background
A method for synthesizing high-melting-point alcohol propoxylate is mainly used for synthesizing propoxylated pentaerythritol ether, propoxylated bisphenol F ether, propoxylated bisphenol fluorene ether, propoxylated bisphenol A ether, propoxylated neopentyl glycol ether and the like. The carbon-oxygen chain and the aromatic ring or branched chain structure in the product molecule can endow the material with certain toughness and rigidity, so as to improve the structure and the property of the polymer. Can synthesize various functional polymer substances such as polyester, polyurethane, polycarbonate and the like, and can be widely applied to polyurethane glue, UV light-cured coating, polyurethane elastomer and the like. Can be applied to various fields such as chemical coating, 3D printing, automobile manufacturing, electronics, aerospace and the like.
The melting point of raw materials such as pentaerythritol, bisphenol F, bisphenol fluorene, bisphenol A, neopentyl glycol and the like is higher. In the case of the propoxylation reaction, a solvent method or a melting method is often used for synthesizing the product. The solvent method can bring a series of problems of energy consumption, application times, complex device and the like caused by solvent recovery, and the synthetic method can cause high production cost. When the melting method is adopted to synthesize the propoxylate product from the high-melting-point pentaerythritol, bisphenol F, bisphenol fluorene and bisphenol A raw materials, the problems of raw material decomposition, color deepening and the like can be caused to influence the product quality, and the synthesis method is only suitable for synthesizing products with lower product quality.
In addition, products such as propoxylated pentaerythritol ether, propoxylated bisphenol F ether, propoxylated bisphenol fluorene ether, propoxylated bisphenol a ether, propoxylated neopentyl glycol ether and the like are synthesized, and the publications report that the products are mostly prepared by adopting alkali metal hydroxides such as KOH, naOH and the like as catalysts, but the method needs to refine the products to obtain finished products, and the production cost of the products is increased.
The existing method has the problems of high production cost or high product quality of the synthesized product, and the like, and reduces the added value and market competitiveness of the product.
Disclosure of Invention
Aiming at the defects of the existing production method, the invention provides a synthesis method for synthesizing a propoxylate by using an N, N-diisopropylethylamine catalyst and using high-melting alcohol, propylene carbonate and propylene oxide.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a method for synthesizing a high-melting-point alcohol propoxylate comprises the following steps: bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol with high melting point (the melting point temperature is higher than 120 ℃) is taken as a starting material, N-diisopropylethylamine catalyst is added, propylene carbonate and propylene oxide are taken as reaction monomers, and a propoxylate is synthesized.
The dosage of the catalyst is 0.1-10 per mill of the sum of the mass of the starting material, propylene carbonate and propylene oxide.
The catalyst is used in an amount of 3 per mill based on the sum of the mass of the starting material, propylene carbonate and propylene oxide.
In the synthesis process, the reaction temperature is 85-140 ℃, and the reaction pressure is-0.098-0.50 mpa.
In the synthesis process, the reaction temperature was 105 ℃.
The molar ratio of the initiator to the propylene carbonate is 2:1-3.
The molar ratio of the initiator to the propylene carbonate is 1:1.
The molar ratio of the initiator to the propylene oxide is 1:100.
A method for synthesizing a high-melting-point alcohol propoxylate comprises the following specific steps:
(1) Adding an initiator, a catalyst and propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen;
(2) Stirring is started, the reaction temperature is 85-140 ℃, the pressure is controlled at-0.080-0.098 Mpa, and the reaction lasts for 2-5 h;
(3) Introducing a required amount of propylene oxide into a reaction kettle, and carrying out polymerization reaction for 2-10 h under the conditions that the reaction temperature is 85-140 ℃ and the reaction pressure is 0-0.35 MPa;
(4) After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product.
Compared with the prior art, the invention has the following outstanding advantages and positive effects:
1. propylene carbonate is not only used as a propoxylating agent, but propylene carbonate is liquid at room temperature, and can also be used as a dispersing agent in the reaction process for synthesizing the propoxylate, so that the initiator can react with propylene carbonate and propylene oxide under stirring.
2. N, N-diisopropylethylamine is used as a catalyst, and simultaneously, the steric hindrance of the N, N-diisopropylethylamine is large, so that side reactions can be inhibited. The N, N-diisopropylethylamine has excellent catalytic property, the produced propoxylate product has propylene alcohol byproducts produced by propylene oxide isomerization of less than 10ppm, lighter color and luster (Pt-Co) of less than or equal to 20.
3. The boiling point of N, N-diisopropylethylamine is 127 ℃, the N-diisopropylethylamine can be removed by vacuum after the reaction is finished, the refining step is not needed, and the production cost is saved.
Examples of the invention
The analysis method comprises the following steps:
number average molecular weight (Mn), the number average molecular weight of the product was measured by gel chromatography using Agilent 1200 liquid chromatograph G1328B.
The content of the acrylic alcohol by-product was measured by high performance liquid chromatography (RID-10 a, shimadzu corporation).
Preparation of the reaction kettle before implementation: distilled water is used for cleaning a 2.5L high-pressure glass reaction kettle for 3 times, the reaction kettle is dried, and the reaction kettle is cooled to normal temperature for standby.
Example 1
The design and synthesis of the propoxylated pentaerythritol ether product was carried out with a molecular weight of 254.
Pentaerythritol 544g, 3g of N, N-diisopropylethylamine catalyst and 408g of propylene carbonate are added into a reaction kettle, and the air in the reaction kettle is replaced by nitrogen for 3 times. Stirring is started, the reaction temperature is 105 ℃, the pressure is controlled to be-0.080-0.098 mpa, and the reaction is carried out for 4 hours. 232g of propylene oxide is introduced into the reaction kettle, and the polymerization reaction is carried out for 3 hours under the conditions that the reaction temperature is 105 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product. Product analysis: the content of the propylene alcohol by-product is 2.8ppm; the color (Pt-Co) of the product was 8 and the number average molecular weight was 252.
Example 2
The design and synthesis of the propoxylated bisphenol F ether product were carried out with a molecular weight of 548.
Bisphenol F400 g, N-diisopropylethylamine catalyst with a dosage of 3g and propylene carbonate with a dosage of 204g are added into the reaction kettle, and the air in the reaction kettle is replaced by nitrogen for 3 times. Stirring is started, the reaction temperature is 120 ℃, the pressure is controlled to be-0.080-0.098 mpa, and the reaction is carried out for 2 hours. 580g of propylene oxide is introduced into the reaction kettle, and the polymerization reaction is carried out for 6 hours under the conditions that the reaction temperature is 120 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product. Product analysis: the content of the propylene alcohol by-product is 3.5ppm; the color (Pt-Co) of the product was 9 and the number average molecular weight was 546.
Example 3
The design and synthesis of the propoxylated bisphenol fluorene ether product have a molecular weight of 582.
700g of bisphenol fluorene and 306g of propylene carbonate with 8g of N, N-diisopropylethylamine catalyst are added into a reaction kettle, and the air in the reaction kettle is replaced by nitrogen for 3 times. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080-0.098 mpa, and the reaction is carried out for 3 hours. 290g of propylene oxide is introduced into the reaction kettle, and the polymerization reaction is carried out for 4 hours under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product. Product analysis: the content of the propylene alcohol by-product is 4.1ppm; the color (Pt-Co) of the product was 7 and the number average molecular weight was 580.
Example 4
The design synthesis of the propoxylated bisphenol A ether product was designed to have a molecular weight of 408.
Bisphenol A570 g, N-diisopropylethylamine catalyst in an amount of 3g and propylene carbonate in an amount of 204g were added to the reaction vessel, and the air in the reaction vessel was replaced with nitrogen for 3 times. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080-0.098 mpa, and the reaction is carried out for 3.5h. 319g of propylene oxide is introduced into the reaction kettle, and the polymerization reaction is carried out for 4 hours under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product. Product analysis: the content of the propylene alcohol by-product is 3.2ppm; the color (Pt-Co) of the product was 12 and the number average molecular weight was 406.
Example 5
The synthetic propoxylated neopentyl glycol ether product was designed to have a molecular weight of 221.
Neopentyl glycol 520g, N-diisopropylethylamine catalyst with a dosage of 3g and propylene carbonate 255g are added into a reaction kettle, air in the reaction kettle is replaced by nitrogen, and nitrogen is replaced for 3 times. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080-0.098 mpa, and the reaction is carried out for 3 hours. 435g of propylene oxide is introduced into the reaction kettle, and the polymerization reaction is carried out for 4.5h under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product. Product analysis: the content of the propylene alcohol by-product is 3.5ppm; the color (Pt-Co) of the product was 10 and the number average molecular weight was 220.
While the foregoing is directed to the preferred embodiments of the present invention, it will be appreciated by those skilled in the art that various changes and modifications in the formulation or reaction conditions may be made without departing from the principles of the present invention, and such changes and modifications are to be considered as being within the scope of the present invention.
Claims (7)
1. The synthesis method of the alcohol propoxylate with high melting point is characterized by comprising the following steps: bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol are used as an initiator, the melting point temperature of the initiator exceeds 120 ℃, an N, N-diisopropylethylamine catalyst is added, and propylene carbonate and propylene oxide are used as reaction monomers to synthesize a propoxylate; adding an initiator, a catalyst and propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen; (2) Stirring is started, the reaction temperature is 85-140 ℃, the pressure is controlled at-0.080-0.098 mpa, and the reaction lasts for 2-5 h; (3) Introducing a required amount of propylene oxide into a reaction kettle, and carrying out polymerization reaction for 2-10 h under the conditions that the reaction temperature is 85-140 ℃ and the reaction pressure is 0-0.35 MPa; (4) After the reaction is finished, the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide are removed in vacuum, and the materials are cooled to obtain the finished product.
2. The method for synthesizing a high-melting-point alcohol propoxylate according to claim 1, characterized in that: the dosage of the catalyst is 0.1-10 per mill of the sum of the mass of the initiator, the mass of the propylene carbonate and the mass of the propylene oxide.
3. A method for synthesizing a high melting point alcohol propoxylate as set forth in claim 2, wherein: the catalyst is used in an amount of 3 per mill based on the mass sum of the initiator, propylene carbonate and propylene oxide.
4. The method for synthesizing a high-melting-point alcohol propoxylate according to claim 1, characterized in that: the reaction temperature of the steps (2) and (3) in the synthesis process is 105 ℃.
5. The method for synthesizing a high-melting-point alcohol propoxylate according to claim 1, characterized in that: the molar ratio of the initiator to the propylene carbonate is 2:1-3.
6. The method for synthesizing a high-melting-point alcohol propoxylate according to claim 5, wherein: the molar ratio of the initiator to the propylene carbonate is 1:1.
7. The method for synthesizing a high-melting-point alcohol propoxylate according to claim 1, characterized in that: the molar ratio of the initiator to the propylene oxide is 1:100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211546113.2A CN115784849B (en) | 2022-12-05 | 2022-12-05 | Synthesis method of high-melting-point alcohol propoxylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211546113.2A CN115784849B (en) | 2022-12-05 | 2022-12-05 | Synthesis method of high-melting-point alcohol propoxylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115784849A CN115784849A (en) | 2023-03-14 |
| CN115784849B true CN115784849B (en) | 2024-04-05 |
Family
ID=85445459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211546113.2A Active CN115784849B (en) | 2022-12-05 | 2022-12-05 | Synthesis method of high-melting-point alcohol propoxylate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115784849B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022044477A1 (en) * | 2019-12-25 | 2022-03-03 | サカタインクス株式会社 | Inkjet textile-printing ink composition, method for inkjet textile printing, and inkjet textile-printed material |
-
2022
- 2022-12-05 CN CN202211546113.2A patent/CN115784849B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022044477A1 (en) * | 2019-12-25 | 2022-03-03 | サカタインクス株式会社 | Inkjet textile-printing ink composition, method for inkjet textile printing, and inkjet textile-printed material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115784849A (en) | 2023-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100677809B1 (en) | Production of Polytrimethylene Ether Glycol and Copolymers thereof | |
| US6617419B1 (en) | Long-chain polyether polyols with a high proportion of primary oh groups | |
| US7528288B2 (en) | Method for production of polyether alcohols | |
| US5364973A (en) | Productive process for making conventional and low-unsaturation polyether polyols | |
| GB2589033A (en) | Vegetable oil polyol and preparation method and application thereof in polyurethane material | |
| CN115784849B (en) | Synthesis method of high-melting-point alcohol propoxylate | |
| RU2510798C2 (en) | Method of obtaining polyols basing on renewable initial raw material | |
| US7342142B2 (en) | Hydrogenation of polytrimethylene ether glycol | |
| Hall et al. | Synthesis of a series of cyclic oligo (alkylidene isophthalate) s by cyclo-depolymerisation | |
| GB2154594A (en) | Process for the continuous production of polybutylene terephthalate of high molecular weight | |
| US5625045A (en) | Process for the production of low viscosity high functionality, light colored polyethers based on sucrose | |
| CN107987268B (en) | Synthetic method for producing polycarbonate polyol by using double catalysts | |
| US4464526A (en) | Preparation of polycaprolactone | |
| US10745375B2 (en) | Adipate-type compounds and a process of preparing it | |
| JPH02232228A (en) | Production of polyalcohol | |
| CN113754876B (en) | Bisphenol A polyether polyol and preparation method thereof | |
| CA1081245A (en) | Terephthalic acid ethylene glycol esters, their production and use in the production of polyester polymers | |
| Gong et al. | Preparation and characterization of biopolyol via liquefaction of rice straw | |
| CN111087600B (en) | Polyurethane elastomer resin and preparation method thereof | |
| CN114874425B (en) | Amino polyether polyol and preparation method thereof | |
| CN117050293A (en) | Synthesis method of high molecular weight pentaerythritol polyether | |
| CN114316254B (en) | Polyether polyol and preparation method and application thereof | |
| JPS6134023A (en) | Production of novel polyhydroxyl compound | |
| EP0876418B1 (en) | Process for preparing low unsaturation polyether polyols | |
| CN116410459A (en) | Preparation method and application of macromolecular stabilizer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |