CN114292395A - Purification method for preparing PECH by cationic polymerization - Google Patents
Purification method for preparing PECH by cationic polymerization Download PDFInfo
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- CN114292395A CN114292395A CN202111580212.8A CN202111580212A CN114292395A CN 114292395 A CN114292395 A CN 114292395A CN 202111580212 A CN202111580212 A CN 202111580212A CN 114292395 A CN114292395 A CN 114292395A
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- 238000000034 method Methods 0.000 title claims abstract description 38
- 229920002755 poly(epichlorohydrin) Polymers 0.000 title claims abstract description 26
- 238000010538 cationic polymerization reaction Methods 0.000 title claims abstract description 7
- 238000000746 purification Methods 0.000 title claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 43
- 239000002904 solvent Substances 0.000 claims abstract description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000047 product Substances 0.000 claims abstract description 30
- 238000003756 stirring Methods 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- 239000003208 petroleum Substances 0.000 claims abstract description 15
- 238000010992 reflux Methods 0.000 claims abstract description 14
- 238000001914 filtration Methods 0.000 claims abstract description 13
- 239000006227 byproduct Substances 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 12
- -1 cyclic crown ether Chemical class 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 13
- 239000002274 desiccant Substances 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003384 small molecules Chemical class 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 6
- 238000005406 washing Methods 0.000 description 18
- 238000000605 extraction Methods 0.000 description 10
- 238000003760 magnetic stirring Methods 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000004449 solid propellant Substances 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012656 cationic ring opening polymerization Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a purification method for preparing PECH by cationic polymerization, which comprises the following steps: a) mixing the crude product with a methanol aqueous solution, stirring, standing for layering to obtain a lower oil phase, and removing the solvent to obtain a first crude product; b) adding petroleum ether into the first crude product, stirring and heating to T1Refluxing at a preset temperature, and cooling to T2Standing and layering, wherein the upper layer is a byproduct of cyclic crown ether and micromolecular oligomer, and the lower layer is a second crude product; c) drying the second crude product, and filtering to obtain a third crude product; d) and removing the solvent in the third crude product system by using rotary evaporation equipment to obtain a main product PECH. The main and side products of the invention are separated thoroughly, the product PECH with high purity and narrow molecular weight distribution can be obtained, and the separation process is safe and controllable.
Description
Technical Field
The application relates to the technical field of chemical industry, in particular to a purification method for preparing PECH by cationic polymerization.
Background
The hydroxyl-terminated Polyepichlorohydrin (PECH) is an important raw material of polyazide glycidyl ether (GAP) which is a solid propellant adhesive component, and in the process of preparing the PECH by cationic ring-opening polymerization, as the reaction is complex and the side reaction is more, except the generation of cyclic crown ether with zero functionality, the generation of oligomers with small molecules is often accompanied. The presence of these cyclic crown ethers and small molecular oligomers will seriously affect the number average relative molecular mass of the polyether and its distribution, average functionality, etc., and deteriorate the polyether quality. The polyurethane prepared by the polyether slowly volatilizes oligomers with low relative molecular mass when the temperature is increased, and the capability of dissolving organic solvent is continuously improved, so that when the polyurethane product is exposed to high temperature or contacts organic solvent, the quality reduction and the size change of the product are caused. Especially in solid propellants, the oligomer content should be more strictly controlled. To prepare a narrow distribution of PECH, the polymerization conditions can be controlled, for example, by terminating the polymerization reaction before the equilibrium of the polymerization reaction is reached; on the other hand, low molecular weight oligomers can be removed through post-treatment, common methods include solvent extraction, reduced pressure distillation and the like, the reduced pressure distillation method is high in energy consumption and difficult to remove cyclic crown ether and oligomers, a byproduct separation method generated in the PECH synthesis process is reported at home and abroad currently, the separation of crown ether byproducts extracted by organic solvents introduced by related documents is not thorough, and even a large amount of main products are dissolved in a separation liquid, so that the yield of the main products is low, the production of products is influenced, and the environmental protection pressure of enterprises is increased.
Disclosure of Invention
The embodiment of the application aims to provide a purification method for preparing PECH by cationic polymerization, which has good separation effect of main and side products and small solvent consumption.
According to an embodiment of the present application, there is provided a purification method for producing PECH by cationic polymerization, including:
a) mixing the crude product with a methanol aqueous solution, stirring, standing for layering to obtain a lower oil phase, and removing the solvent to obtain a first crude product;
b) adding petroleum ether into the first crude product, stirring and heating to T1Cooling to T after reflux number for preset time2Standing and layering, wherein the upper layer is a byproduct of cyclic crown ether and micromolecular oligomer, and the lower layer is a second crude product; according to the step, the cyclic crown ether can be extracted for 3-4 times to obtain more byproducts. The by-product cyclic crown ether has the following molecular structural formula:
c) drying the second crude product, and filtering to obtain a third crude product;
d) and removing the solvent in the third crude product system by using rotary evaporation equipment to obtain a main product PECH.
Preferably, in step a), the mass ratio of methanol to water in the methanol aqueous solution is 1: (1-9).
Preferably, in a), the mass ratio of the crude product to the methanol aqueous solution is 1 (1-2), preferably 1: 1.
Preferably, in b), the mass ratio of the petroleum ether to the first crude product is (10-30): (5-10).
Preferably, in b), T1Is (64-70 ℃), preferably 65 ℃, T2Is (30-50 ℃), preferably 45 ℃.
Preferably, in b), the reflux time is (0.2-1 h), and preferably 0.5 h.
Preferably, in b), the cyclic crown ether has a functionality of 0, which is typically an n-mer, where n is 2 to 4.
Preferably, in b), the structural general formula of the small molecule oligomer is:
wherein n is an integer less than 10.
Preferably, in step c), the drying agent used for drying is one or more of anhydrous magnesium sulfate, calcium carbonate and calcium chloride, and anhydrous magnesium sulfate is preferred.
Preferably, in the step d), the rotary evaporation temperature is (60-75 ℃), preferably 70 ℃, and the rotary evaporation time is (0.5-2 h), preferably 1 h.
The technical scheme provided by the embodiment of the application can have the following beneficial effects:
according to the embodiment, the method that the methanol aqueous solution is firstly washed and then the petroleum ether solution is used for extraction is adopted, the problem that the byproducts such as low-molecular-mass oligomers and cyclic crown ether in the crude polymer product are difficult to separate simultaneously is solved, the main and side products are thoroughly separated, and the product PECH with high purity and narrow molecular weight distribution can be obtained. The separation process has the advantages of safety, controllability, less solvent consumption and the like, and the production cost can be further reduced while the product purity is improved.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.
Detailed Description
Exemplary embodiments will be described in detail herein. The embodiments described in the following exemplary embodiments do not represent all embodiments consistent with the present application. Rather, they are merely examples of apparatus and methods consistent with certain aspects of the present application, as detailed in the appended claims.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used in this application and the appended claims, the singular forms "a", "an", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It should also be understood that the term "and/or" as used herein refers to and encompasses any and all possible combinations of one or more of the associated listed items.
Example 1
a) Washing: putting the crude product and a 10% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 10:5, heating the interior of the flask to 64 ℃ under the condition of magneton stirring, refluxing for 1h, cooling to 45 ℃, standing for layering, extracting for 3-4 times according to the method, wherein the upper layer is a byproduct of cyclic crown ether, and the lower layer is a second crude product;
c) drying and filtering: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 59%.
Example 2
a) Washing: putting the crude product and a 10% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 30:5, heating the interior of the flask to 65 ℃ under the condition of magneton stirring, refluxing for 0.5h, cooling to 50 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. And removing the solvent in the third crude product system by rotary evaporation to obtain the main product PECH with extremely high purity, wherein the product yield is 40%.
Example 3
a) Washing: putting the crude product and a 10 mass percent methanol aqueous solution into a single-neck flask with magnetic stirring according to the mass ratio of 1:2, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent through rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 30:10, heating the interior of the flask to 68 ℃ under the condition of stirring by a magnet, refluxing for 0.8h, cooling to 35 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 53%.
Example 4
a) Washing: putting the crude product and 15% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 10:10, heating the interior of the flask to 65 ℃ under the condition of stirring by a magnet, refluxing for 0.5h, cooling to 45 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 67%.
Example 5
a) Washing: putting the crude product and a methanol aqueous solution with the mass concentration of 20% into a single-neck flask with magnetic stirring according to the mass ratio of 1:1, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent through rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 20:5, heating the interior of the flask to 65 ℃ under the condition of magneton stirring, refluxing for 0.5h, cooling to 45 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. And removing the solvent in the third crude product system by rotary evaporation to obtain the main product PECH with extremely high purity and 50% of product yield.
Example 6
a) Washing: putting the crude product and 30% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 25:9, heating the interior of the flask to 70 ℃ under the condition of magneton stirring, refluxing for 0.3h, cooling to 30 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 53%.
Example 7
a) Washing: putting the crude product and 40% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 15:7, heating the interior of the flask to 65 ℃ under the condition of magneton stirring, refluxing for 0.5h, cooling to 45 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 59%.
Example 8
a) Washing: putting the crude product and 50% methanol aqueous solution in a mass ratio of 1:1 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 25:10, heating the interior of the flask to 65 ℃ under the condition of stirring by a magnet, refluxing for 0.5h, cooling to 50 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 58%.
Example 9
a) Washing: putting the crude product and 50% methanol aqueous solution in a mass ratio of 1:2 into a single-neck flask with magnetic stirring, stirring for 30 minutes, standing for layering, taking down the layer, washing for 4 times according to the method, and removing the solvent by rotary evaporation to obtain a first crude product;
b) and (3) extraction: adding petroleum ether and the first crude product into a single-neck flask according to the mass ratio of 25:5, heating the interior of the flask to 70 ℃ under the condition of magneton stirring, refluxing for 0.2h, cooling to 30 ℃, standing for layering, taking the second crude product at the lower layer, and extracting for 3-4 times according to the method;
c) and (3) drying: adding anhydrous magnesium sulfate serving as a drying agent with the mass ratio of 5% into the second crude product, fully mixing, drying, and filtering through filter paper to obtain a third crude product;
d) removing the solvent: setting the rotary evaporation temperature at 70 ℃ and the rotary evaporation time at 1 h. The solvent in the third crude product system is removed by rotary evaporation, so that the main product PECH with extremely high purity is obtained, and the product yield is 45%.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the disclosure disclosed herein. This application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.
It is to be understood that the present application is not limited to what has been described above, and that various modifications and changes may be made without departing from the scope thereof. The scope of the application is limited only by the appended claims.
Claims (10)
1. A purification process for the preparation of PECH by cationic polymerization, comprising:
a) mixing the crude product with a methanol aqueous solution, stirring, standing for layering to obtain a lower oil phase, and removing the solvent to obtain a first crude product;
b) adding petroleum ether into the first crude product, stirring and heating to T1Cooling to T after reflux number for preset time2Standing and layering, wherein the upper layer is a byproduct of cyclic crown ether and micromolecular oligomer, and the lower layer is a second crude product;
c) drying the second crude product, and filtering to obtain a third crude product;
d) and removing the solvent in the third crude product system by using rotary evaporation equipment to obtain a main product PECH.
2. The method as claimed in claim 1, wherein in the step a), the mass ratio of methanol to water in the methanol aqueous solution is 1: (1-9).
3. The method as claimed in claim 1, wherein the mass ratio of the crude product to the aqueous methanol solution in a) is 1 (1-2), preferably 1: 1.
4. The method as claimed in claim 1, wherein the mass ratio of the petroleum ether to the first crude product in b) is (10-30): (5-10).
5. The method as claimed in claim 1, wherein in b), T1Is (64-70 ℃), preferably 65 ℃, T2Is (30-50 ℃), preferably 45 ℃.
6. The process of claim 1, wherein in b) the reflux time is (0.2 to 1 hour), preferably 0.5 hour.
7. The method according to claim 1, wherein the cyclic crown ether in b) has a functionality of 0 and is an n-mer, wherein n is 2 to 4.
8. The method of claim 1, wherein in b), the small molecule oligomer has the general structural formula:
wherein n is an integer less than 10.
9. The method as set forth in claim 1, wherein in the step c), the drying agent is one or more of anhydrous magnesium sulfate, calcium carbonate and calcium chloride, preferably anhydrous magnesium sulfate.
10. The process according to claim 1, wherein in step d) the rotary evaporation temperature is (60-75 ℃), preferably 70 ℃ and the rotary evaporation time is (0.5-2 h), preferably 1 h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102174185A (en) * | 2011-01-31 | 2011-09-07 | 武汉工程大学 | Synthesis technology of hydroxyl terminated polyepichlorohydrin |
| CN104448288A (en) * | 2014-10-28 | 2015-03-25 | 常州大学 | Method for synthesizing polyepichlorohydrin |
-
2021
- 2021-12-22 CN CN202111580212.8A patent/CN114292395A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102174185A (en) * | 2011-01-31 | 2011-09-07 | 武汉工程大学 | Synthesis technology of hydroxyl terminated polyepichlorohydrin |
| CN104448288A (en) * | 2014-10-28 | 2015-03-25 | 常州大学 | Method for synthesizing polyepichlorohydrin |
Non-Patent Citations (2)
| Title |
|---|
| 卢先明;甘孝贤;邢颖;张志刚;韩涛;: "端羟基聚环氧氯丙烷与叠氮聚醚的后处理研究", 含能材料, no. 06, 15 December 2008 (2008-12-15), pages 48 - 51 * |
| 宋晓庆;周集义;王文浩;王建伟;白森虎;: "端羟基聚环氧氯丙烷制备过程中齐聚物的生成与去除", 化学推进剂与高分子材料, no. 06, 25 November 2007 (2007-11-25), pages 44 - 47 * |
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| CB03 | Change of inventor or designer information | ||
| CB03 | Change of inventor or designer information |
Inventor after: Qi Yongxin Inventor after: Wang Jiansheng Inventor after: Li Bing Inventor after: Lv Debin Inventor after: Shi Zhe Inventor after: Dong Changchun Inventor before: Qi Yongxin Inventor before: Wang Jiansheng Inventor before: Hu Pan Inventor before: Li Bing Inventor before: Lv Debin Inventor before: Shi Zhe Inventor before: Dong Changchun |