CN111437738A - Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane - Google Patents
Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane Download PDFInfo
- Publication number
- CN111437738A CN111437738A CN202010123581.3A CN202010123581A CN111437738A CN 111437738 A CN111437738 A CN 111437738A CN 202010123581 A CN202010123581 A CN 202010123581A CN 111437738 A CN111437738 A CN 111437738A
- Authority
- CN
- China
- Prior art keywords
- polyimide
- click
- separation membrane
- amino
- dissolving
- 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.)
- Granted
Links
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/50—Carbon oxides
- B01D2257/504—Carbon dioxide
-
- 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
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Polyimide CO grafted with amino through click chemistry2A preparation method of a separation membrane belongs to the technical field of membrane separation, and aims to provide polyimide with amino or amino and hydroxyl mixed functional groups modified on the polyimide by a click chemistry method. The invention prepares the polyimide grafted with amino or amino and hydroxyl mixed functional groups by adopting commercial monomers to synthesize the polyimide, then brominating, azidizing and carrying out click chemical cyclization reaction with one or two alkynyl compounds with functional groups, so as to obtain higher gas separation performance, and the polyimide can be potentially applied to CO2Separating and trapping.
Description
Technical Field
The invention belongs to the technical field of membrane separation, and particularly relates to polyimide CO grafted with amino through click chemistry2A method for preparing a separation membrane.
Background
CO2Is a main greenhouse gas and is one of the main causes of global warming and extreme weather, therefore, CO is separated, removed and effectively captured2Has become a hot spot of worldwide interest in recent years. At present, CO2The main sources of the CO are tail gases of power plants, steel plants, cement plants and the like, and CO in the gas sources2The emission is almost the entire CO260% of the discharge; in addition, natural gas, biogas and shift synthesis gas also contain a large amount of CO2Which needs to be removed during the purification process. CO 22On the one hand greenhouse gases and on the other hand CO2The composite material is also an important resource and industrial gas, and has wide application in the fields of chemical industry, oil exploitation, food, agriculture, tobacco, fire fighting and the like. Thus, CO is separated and trapped2Realization of CO2The separation, recovery and comprehensive utilization are beneficial measures with two functions.
At present, CO2The separation and collection method mainly includes an adsorption method, a solution absorption method, a low-temperature separation method and a membrane separation method. Compared with other methods, the membrane separation technology has the advantages of economy, high efficiency, energy conservation, no secondary pollution, small occupied area and the like, and becomes the method for separating and capturing CO2The important technology of gas.
The core of the membrane technology is membrane material, and the preparation of the membrane material with high performance (high permeability and high separation selectivity) is realized by utilizing the membrane technology to carry out CO separation2Gas effectiveKey to separation and capture. Polyimide is a glassy polymer, the main chain of the molecule of the glassy polymer contains a nitrogen aromatic heterocyclic ring structure, the heat resistance is excellent, the glass transition temperature is high, and therefore chain segment motion of a polyimide molecular chain is limited under the common use temperature, and the glassy polymer has high rigidity. The polyimide has the characteristic that the molecular chain of the polyimide has high free volume and moderate chain spacing, so that a higher gas separation factor and better gas permeability can be obtained. However, the permeability of polyimide still has a certain gap with the requirement of industrial application, so that the large-scale application of polyimide in gas separation is restricted. However, the difficulty in synthesizing the polyimide with a new structure is very great, and the preparation of the polyimide by using commercial monomers and then the graft modification on the basis of the polyimide is a simple and effective way for obtaining the polyimide with high performance.
The click chemistry method is a simple and effective organic chemistry synthesis method, is a new combinatorial chemistry method based on carbon-heteroatom bond (C-X-C) synthesis, and can simply and efficiently carry out functional grafting modification on macromolecules by means of click reaction. Therefore, it is expected that the functional polyimide can be efficiently prepared by synthesizing polyimide by using commercial monomers, and then carrying out click chemical cyclization reaction by bromination, azidation and then carrying out reaction with alkynyl compounds with amino groups, so as to prepare the high-performance gas separation membrane material.
Disclosure of Invention
The invention aims to provide polyimide with amino or a mixture of amino and hydroxyl functional groups modified on the polyimide by a click chemistry method. The polyimide grafted with amino or amino and hydroxyl mixed functional groups is prepared by synthesizing polyimide by adopting commercial monomers, then carrying out bromination and azide, and carrying out click chemical cyclization reaction with one or two alkynyl compounds with functional groups, so that the polyimide with higher gas separation performance can be obtained, and can be potentially applied to CO2Separating and trapping.
The invention adopts the following technical scheme:
polyimide CO grafted with amino through click chemistry2Method for producing separation membrane, and bagThe method comprises the following steps:
step one, preparing polyimide:
4,4' - (hexafluoroisopropylidene) diphthalic anhydride is placed in a sublimation furnace to be treated for 12 hours at the temperature of 130-200 ℃, and 2, 5-dimethyl-1, 4-phenylenediamine is placed in a vacuum drying box to be dried for 12 hours in vacuum; adding 2, 5-dimethyl-1, 4-phenylenediamine into an experimental device which is filled with protective gas at one time, adding N, N-dimethylacetamide for dissolving for the first time, keeping the temperature of an ice water bath less than 5 ℃ in the dissolving process, adding 4,4' - (hexafluoroisopropylidene) diphthalic anhydride in batches and adding N, N-dimethylacetamide for the second time after the 2, 5-dimethyl-1, 4-phenylenediamine is completely dissolved, reacting for 48 hours, adding 3-methylpyridine and 95, continuing to react for 48 hours, after the reaction is finished, precipitating and washing a reaction product by using methanol, and drying the reaction product in a vacuum drying oven for later use to obtain polyimide;
step two, preparing brominated polyimide:
adding the polyimide prepared in the first step into a three-neck flask, adding 1, 2-dichloroethane for dissolving, after the dissolving is finished, adding N-bromosuccinimide and azobisisobutyronitrile, reacting at 50-100 ℃ for 3-6 h, precipitating and washing with methanol, and drying the product in a vacuum drying oven to obtain bromopolyimide;
step three, nitridizing the polyimide:
adding the brominated polyimide prepared in the second step into a three-neck flask, adding N-methyl pyrrolidone for dissolution, and adding NaN3Heating to 50-100 ℃ for reaction for 24h, precipitating the reaction product by using a methanol-water mixed solution, washing the precipitate for 2-3 times by using distilled water, and drying in a vacuum drying oven for later use to obtain the azide polyimide;
fourthly, preparing click functional polyimide:
weighing the product obtained in the third step, adding the product into a Schlenk bottle, dissolving the product with N-methyl pyrrolidone to prepare a solution, placing the Schlenk bottle into liquid nitrogen for cooling, degassing, filling high-purity nitrogen, adding cuprous bromide, pentamethyl diethylenetriamine and an alkynyl compound in proportion, heating the Schlenk bottle to 50-100 ℃, stirring for reaction for 24 hours, precipitating the reaction product with diethyl ether, washing the precipitate with distilled water for 2-3 times, and then placing the precipitate in a vacuum drying oven for drying to obtain the click functionalized polyimide;
fifthly, preparing a gas separation membrane:
adding the click functional polyimide into a sample bottle, adding N-methyl pyrrolidone for dissolving, filtering, uniformly coating the solution on a glass plate, and drying the glass plate at 80 ℃ to form a film.
The ratio of the 2, 5-dimethyl-1, 4-phenylenediamine to the first addition of N, N-dimethylacetamide in the first step was 13.6205 g: 140m L and the ratio of 4,4' - (hexafluoroisopropylene) diphthalic anhydride to the second addition of N, N-dimethylacetamide was 44.424 g: 92m L.
In the second step, the ratio of the polyimide, 1, 2-dichloroethane, N-bromosuccinimide and azobisisobutyronitrile was 10g to 200m L to 6.5466g to 0.1745 g.
In the third step, the ratio of the brominated polyimide to the N-methylpyrrolidone is 5g to 50m L, and NaN3And the molar ratio of the brominated polyimide to the brominated polyimide is 2-3.
In the fourth step, the using amount of the polyimide azide is 3g, the concentration of the solution after the N-methyl pyrrolidone is dissolved is 10 percent, the proportion of the cuprous bromide to the pentamethyl diethylenetriamine is 0.206g to 600 mu L, and the alkynyl compound is 665.6 mu L diethyl propyne amine or 520.9 mu L diethyl propyne amine and 70 mu L propyne alcohol.
In the fifth step, the ratio of the click functionalized polyimide to the N-methylpyrrolidone is 1 g: 9 g.
The invention has the following beneficial effects:
the invention provides a functionalized polyimide with carboxylate radicals and hydroxyl radicals modified on polyimide by a click chemistry method. The functional polyimide is efficiently prepared by synthesizing polyimide by adopting commercial monomers, then carrying out bromination and azidation, and then carrying out click chemical cyclization reaction with alkynyl compounds with carboxylate radicals and hydroxyl radicals. The preparation method of the material is novel and efficient, the prepared polyimide film material is easy to prepare, and CO is easy to prepare2The separation performance is excellent, and the method can be potentially applied to CO in occasions such as flue gas or natural gas2Separating and trapping.
Drawings
FIG. 1 is a reaction scheme of the present invention.
FIG. 2 is a surface electron micrograph of a gas separation membrane according to example 1 of the present invention.
FIG. 3 is a sectional electron micrograph of a gas separation membrane according to example 1 of the present invention.
FIG. 4 is a surface electron micrograph of a gas separation membrane according to example 2 of the present invention.
FIG. 5 is a sectional electron micrograph of a gas separation membrane according to example 2 of the present invention.
Detailed Description
Example 1
Step 1, preparation of polyimide: 4,4' - (hexafluoroisopropylidene) diphthalic anhydride is placed in a sublimation furnace to be treated for 12 hours at the temperature of 200 ℃, and 2, 5-dimethyl-1, 4-phenylenediamine is placed in a vacuum drying oven to be dried for 12 hours in vacuum at the temperature of 50 ℃; 13.6205g of 2, 5-dimethyl-1, 4-phenylenediamine is weighed and added into a three-neck flask with nitrogen protection gas at one time, 140ml of N, N-dimethylacetamide is added for dissolution, the temperature is controlled to be less than 5 ℃ in the dissolution process, and after the 2, 5-dimethyl-1, 4-phenylenediamine is completely dissolved, 44.424g of 4,4' - (hexafluoroisopropylidene) diphthalic anhydride and 92ml of N, N-dimethylacetamide are added in five times (added once every 15 min). After 48 hours of reaction, 9.73ml of 3-methylpyridine and 95 ml of acetic anhydride were added to continue the reaction for 48 hours. And precipitating and washing a reaction product by using methanol, and finally, placing the obtained polyimide in a vacuum drying oven for drying at 60 ℃ for later use.
Step 2, preparing brominated polyimide: weighing 10g of the polyimide prepared in the step 1, adding the polyimide into a three-neck flask, adding 200ml of 1, 2-dichloroethane, and stirring for dissolving; after the dissolution is finished, 6.5466g N-bromosuccinimide and 0.1745g of azobisisobutyronitrile are added, the mixture is heated at 100 ℃ for reaction for 6 hours, methanol is precipitated and washed, and the product is dried in vacuum at 60 ℃ for standby.
Step 3, nitridizing the polyimide: weighing 5g of the brominated polyimide obtained in the step 1, adding the brominated polyimide into a three-neck flask, adding 50ml of N-methylpyrrolidone for dissolution, and adding 2.3148g of NaN3Reacting for 24 hours at 50 ℃; the reaction product was precipitated with a methanol-water mixed solution (methanol: distilled water = 1: 3), and the precipitate was washed with distilled water 3Then dried in vacuum at 60 ℃.
And 4, preparing the click functional polyimide, namely weighing 3g of the polyimide azide in the step 3, adding the polyimide azide into a Schlenk bottle, adding N-methylpyrrolidone to dissolve the polyimide to prepare a solution with the mass concentration of 10%, placing the Schlenk bottle into liquid nitrogen to cool, degassing, filling high-purity nitrogen into the bottle, continuously circulating for three times, adding 665.6 mu L diethylpropynylamine, 600 mu L pentamethyldiethylenetriamine and 0.206g of cuprous bromide, stirring and reacting for 24 hours at 50 ℃, precipitating a reaction product by using diethyl ether, cleaning the precipitate by using distilled water for 2-3 times, and then drying in vacuum at 80 ℃.
Step 5, preparing a gas separation membrane and testing the performance: weighing 1g of the click functional polyimide obtained in the step 4, placing the click functional polyimide in a sample bottle, adding 9g N-methyl pyrrolidone to dissolve the click functional polyimide to prepare a solution with the mass concentration of 10%, filtering the solution, uniformly coating the solution on a glass plate, and drying the solution at 80 ℃ to obtain the functional polyimide film. The prepared gas separation membrane is tested by adopting a gas separation device, and the result shows that the prepared functionalized polyimide gas separation membrane has good CO2/N2Separation Performance, CO2The permeability coefficient can reach 1013Barrer and the separation factor can reach 47. The surface and cross section of the prepared gas separation membrane 1 are shown in fig. 2 and fig. 3, respectively.
Example 2
Step 1, preparation of polyimide: 4,4' - (hexafluoroisopropylidene) diphthalic anhydride is placed in a sublimation furnace to be treated for 12 hours at the temperature of 200 ℃, and 2, 5-dimethyl-1, 4-phenylenediamine is placed in a vacuum drying oven to be dried for 12 hours in vacuum at the temperature of 50 ℃; 13.6205g of 2, 5-dimethyl-1, 4-phenylenediamine is weighed and added into a three-neck flask with nitrogen protection gas at one time, 140ml of N, N-dimethylacetamide is added for dissolution, the temperature is controlled to be less than 5 ℃ in the dissolution process, and after the 2, 5-dimethyl-1, 4-phenylenediamine is completely dissolved, 44.424g of 4,4' - (hexafluoroisopropylidene) diphthalic anhydride and 92ml of N, N-dimethylacetamide are added in five times (added once every 15 min). After 48 hours of reaction, 9.73ml of 3-methylpyridine and 95 ml of acetic anhydride were added to continue the reaction for 48 hours. And precipitating and washing a reaction product by using methanol, and finally, placing the obtained polyimide in a vacuum drying oven for drying at 60 ℃ for later use.
Step 2, preparing brominated polyimide: weighing 10g of the polyimide prepared in the step 1, adding the polyimide into a three-neck flask, adding 200ml of 1, 2-dichloroethane, and stirring for dissolving; after the dissolution is finished, 6.5466g N-bromosuccinimide and 0.1745g of azobisisobutyronitrile are added, the mixture is heated at 100 ℃ for reaction for 6 hours, methanol is precipitated and washed, and the product is dried in vacuum at 60 ℃ for standby.
Step 3, nitridizing the polyimide: weighing 5g of the brominated polyimide obtained in the step 1, adding the brominated polyimide into a three-neck flask, adding 50ml of N-methylpyrrolidone for dissolution, and adding 2.3148g of NaN3Reacting for 24 hours at 50 ℃; the reaction product was precipitated with a methanol-water mixed solution (methanol: distilled water = 1: 3), and the precipitate was washed 3 times with distilled water and then dried under vacuum at 60 ℃.
And 4, preparing the click functional polyimide, namely weighing 3g of the polyimide azide in the step 3, adding the polyimide azide into a Schlenk bottle, adding N-methylpyrrolidone to dissolve the polyimide to prepare a solution with the mass concentration of 10%, placing the Schlenk bottle into liquid nitrogen to cool, degassing, filling high-purity nitrogen into the Schlenk bottle, continuously circulating for three times, adding 520.9 mu L diethylpropyne, 70 mu L propiolic alcohol, 600 mu L pentamethyldiethylenetriamine and 0.206g of cuprous bromide, stirring and reacting for 24 hours at 50 ℃, precipitating a reaction product by using diethyl ether, cleaning the precipitate by using distilled water for 2-3 times, and then drying in vacuum at 80 ℃.
Step 5, preparing a gas separation membrane and testing the performance: weighing 1g of the click functional polyimide obtained in the step 4, placing the click functional polyimide in a sample bottle, adding 9g N-methyl pyrrolidone to dissolve the click functional polyimide to prepare a solution with the mass concentration of 10%, filtering the solution, uniformly coating the solution on a glass plate, and drying the solution at 80 ℃ to obtain the functional polyimide film. The prepared gas separation membrane is tested by adopting a gas separation device, and the result shows that the prepared functionalized polyimide gas separation membrane has good CO2/N2Separation Performance, CO2The permeability coefficient can reach 1533 Barrer, and the separation factor can reach 43. The surface and cross section of the prepared gas separation membrane 2 are shown in fig. 4 and fig. 5, respectively.
Claims (6)
1. Polyimide CO grafted with amino through click chemistry2The preparation method of the separation membrane is characterized by comprising the following steps: the method comprises the following steps:
step one, preparing polyimide:
4,4' - (hexafluoroisopropylidene) diphthalic anhydride is placed in a sublimation furnace to be treated for 12 hours at the temperature of 130-200 ℃, and 2, 5-dimethyl-1, 4-phenylenediamine is placed in a vacuum drying box to be dried for 12 hours in vacuum; adding 2, 5-dimethyl-1, 4-phenylenediamine into an experimental device which is filled with protective gas at one time, adding N, N-dimethylacetamide for dissolving for the first time, keeping the temperature of an ice water bath less than 5 ℃ in the dissolving process, adding 4,4' - (hexafluoroisopropylidene) diphthalic anhydride in batches and adding N, N-dimethylacetamide for the second time after the 2, 5-dimethyl-1, 4-phenylenediamine is completely dissolved, reacting for 48 hours, adding 3-methylpyridine and 95, continuing to react for 48 hours, after the reaction is finished, precipitating and washing a reaction product by using methanol, and drying the reaction product in a vacuum drying oven for later use to obtain polyimide;
step two, preparing brominated polyimide:
adding the polyimide prepared in the first step into a three-neck flask, adding 1, 2-dichloroethane for dissolving, after the dissolving is finished, adding N-bromosuccinimide and azobisisobutyronitrile, reacting at 50-100 ℃ for 3-6 h, precipitating and washing with methanol, and drying the product in a vacuum drying oven to obtain bromopolyimide;
step three, nitridizing the polyimide:
adding the brominated polyimide prepared in the second step into a three-neck flask, adding N-methyl pyrrolidone for dissolution, and adding NaN3Heating to 50-100 ℃ for reaction for 24h, precipitating the reaction product by using a methanol-water mixed solution, washing the precipitate for 2-3 times by using distilled water, and drying in a vacuum drying oven for later use to obtain the azide polyimide;
fourthly, preparing click functional polyimide:
weighing the product obtained in the third step, adding the product into a Schlenk bottle, dissolving the product with N-methyl pyrrolidone to prepare a solution, placing the Schlenk bottle into liquid nitrogen for cooling, degassing, filling high-purity nitrogen, adding cuprous bromide, pentamethyl diethylenetriamine and an alkynyl compound in proportion, heating the Schlenk bottle to 50-100 ℃, stirring for reaction for 24 hours, precipitating the reaction product with diethyl ether, washing the precipitate with distilled water for 2-3 times, and then placing the precipitate in a vacuum drying oven for drying to obtain the click functionalized polyimide;
fifthly, preparing a gas separation membrane:
adding the click functional polyimide into a sample bottle, adding N-methyl pyrrolidone for dissolving, filtering, uniformly coating the solution on a glass plate, and drying the glass plate at 80 ℃ to form a film.
2. The click chemistry amino grafted polyimide CO according to claim 12The preparation method of the separation membrane is characterized in that the proportion of the 2, 5-dimethyl-1, 4-phenylenediamine to the N, N-dimethylacetamide added for the first time in the first step is 13.6205 g: 140m L, and the proportion of the 4,4' - (hexafluoroisopropylidene) diphthalic anhydride to the N, N-dimethylacetamide added for the second time is 44.424 g: 92m L.
3. The click chemistry amino grafted polyimide CO according to claim 12The preparation method of the separation membrane is characterized in that in the second step, the ratio of the polyimide to the 1, 2-dichloroethane to the N-bromosuccinimide to the azobisisobutyronitrile is 10g to 200m, L to 6.5466g to 0.1745 g.
4. The click chemistry amino grafted polyimide CO according to claim 12The preparation method of the separation membrane is characterized in that in the third step, the ratio of the brominated polyimide to the N-methylpyrrolidone is 5 g: 50m L, and NaN3And the molar ratio of the brominated polyimide to the brominated polyimide is 2-3.
5. The click chemistry amino grafted polyimide CO according to claim 12The preparation method of the separation membrane is characterized in that in the fourth step, the using amount of the polyimide azide is 3g, the concentration of a solution obtained after dissolving N-methyl pyrrolidone is 10%, the proportion of cuprous bromide to pentamethyl diethylenetriamine is 0.206g to 600 mu L, and the alkynyl compound is 665.6 mu L diethyl propyne or 520.9 mu L diethyl propyne and 70 mu L propyne alcohol.
6. According toThe click chemistry amino grafted polyimide CO of claim 12The preparation method of the separation membrane is characterized by comprising the following steps: in the fifth step, the ratio of the click functionalized polyimide to the N-methylpyrrolidone is 1 g: 9 g.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010123581.3A CN111437738B (en) | 2020-02-27 | 2020-02-27 | Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010123581.3A CN111437738B (en) | 2020-02-27 | 2020-02-27 | Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111437738A true CN111437738A (en) | 2020-07-24 |
| CN111437738B CN111437738B (en) | 2021-12-03 |
Family
ID=71627071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010123581.3A Active CN111437738B (en) | 2020-02-27 | 2020-02-27 | Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111437738B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103846023A (en) * | 2012-12-05 | 2014-06-11 | 中国科学院大连化学物理研究所 | Copolymerization polyimide gas separation membrane material, preparation method and application of copolymerization polyimide gas separation membrane material |
| US9233344B1 (en) * | 2014-09-29 | 2016-01-12 | Uop Llc | High selectivity polyimide membrane for natural gas upgrading and hydrogen purification |
| CN105555838A (en) * | 2013-09-27 | 2016-05-04 | 环球油品公司 | Self cross-linkable and self cross-linked aromatic polyimide membranes for separations |
| CN107207760A (en) * | 2015-02-06 | 2017-09-26 | 东京应化工业株式会社 | Polyimides and/or polyamidoimide porous plastid and its manufacture method, the method for being separated and/or being adsorbed, separation material, sorbing material, filter medium, layered product and filter |
| CN107376672A (en) * | 2017-06-23 | 2017-11-24 | 江南大学 | A kind of environment-friendly preparation method thereof of polyimide gas separating film |
| CN108102097A (en) * | 2018-01-22 | 2018-06-01 | 吉林大学 | A kind of polyimides of base containing benzyne, preparation method and applications |
| CN110591092A (en) * | 2018-06-13 | 2019-12-20 | 北京大学 | Novel polyimide high polymer material based on 2, 5-diallyloxy p-phenylenediamine monomer and preparation method thereof |
-
2020
- 2020-02-27 CN CN202010123581.3A patent/CN111437738B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103846023A (en) * | 2012-12-05 | 2014-06-11 | 中国科学院大连化学物理研究所 | Copolymerization polyimide gas separation membrane material, preparation method and application of copolymerization polyimide gas separation membrane material |
| CN105555838A (en) * | 2013-09-27 | 2016-05-04 | 环球油品公司 | Self cross-linkable and self cross-linked aromatic polyimide membranes for separations |
| US9233344B1 (en) * | 2014-09-29 | 2016-01-12 | Uop Llc | High selectivity polyimide membrane for natural gas upgrading and hydrogen purification |
| CN107207760A (en) * | 2015-02-06 | 2017-09-26 | 东京应化工业株式会社 | Polyimides and/or polyamidoimide porous plastid and its manufacture method, the method for being separated and/or being adsorbed, separation material, sorbing material, filter medium, layered product and filter |
| CN107376672A (en) * | 2017-06-23 | 2017-11-24 | 江南大学 | A kind of environment-friendly preparation method thereof of polyimide gas separating film |
| CN108102097A (en) * | 2018-01-22 | 2018-06-01 | 吉林大学 | A kind of polyimides of base containing benzyne, preparation method and applications |
| CN110591092A (en) * | 2018-06-13 | 2019-12-20 | 北京大学 | Novel polyimide high polymer material based on 2, 5-diallyloxy p-phenylenediamine monomer and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111437738B (en) | 2021-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111318184B (en) | Click chemical grafting functionalized polyimide CO2Method for producing separation membrane | |
| CN112679731A (en) | Covalent organic framework material containing sulfonic acid group and preparation and application thereof | |
| CN109232781B (en) | Preparation method of nitrogen-containing porous organic polymer | |
| CN109575308A (en) | A kind of fluorine-containing covalent organic frame compound of two dimension without catalysis high efficiency preparation method | |
| CN103435620B (en) | Porous copper organic framework material for CO2 adsorption and separation and preparation method of porous copper organic framework material | |
| CN101816925B (en) | Organic-inorganic hybrid material for CO2 adsorption and preparation method thereof | |
| CN112341633A (en) | MOFs material with high gas adsorbability and preparation method and application thereof | |
| CN110746608A (en) | Nitrogen-containing cyclodextrin polymer porous material and preparation method and application thereof | |
| CN109232226B (en) | Microporous metal organic framework material and preparation method and application thereof | |
| CN114984913A (en) | Preparation method and application of novel carbon capture material | |
| CN105597705B (en) | One kind has excellent CO2Absorption and the ultramicropore covalent triazine framework material and preparation method of separating property | |
| CN108689408B (en) | Method for preparing high-nitrogen porous carbon polymer precursor by solvent-free method | |
| CN111437738B (en) | Polyimide CO grafted with amino through click chemistry2Method for producing separation membrane | |
| CN109734957B (en) | Preparation method of modified metal organic framework material and material prepared by preparation method | |
| CN109012029B (en) | Carbon dioxide adsorption recovery method | |
| CN109680494B (en) | Chelate fiber, preparation method thereof and application of chelate fiber in detection of Cu (II) in preserved eggs | |
| CN115403777B (en) | Three-dimensional carboxylic acid covalent organic framework material, preparation method and application | |
| CN114605602B (en) | Hierarchical pore covalent organic framework compound and preparation method and application thereof | |
| CN110371973A (en) | A kind of poly- p-phenylenediamine/graphene-based nitrogen-doped porous carbon material preparation method | |
| CN111389369A (en) | Synthesis method of metal organic framework mesoporous material and its application in CO2Application in adsorption | |
| CN112934201B (en) | Composite waste gas adsorption material and preparation method thereof | |
| CN113856493A (en) | Preparation and application of photoresponsive polymer-covalent organic framework blending film | |
| CN115677952A (en) | Three-dimensional covalent organic framework material and preparation method and application thereof | |
| CN105885015A (en) | Thiazole cross-linked porous organic polymer and preparation method thereof | |
| CN112717724B (en) | Preparation method and application of mixed matrix carbon molecular sieve membrane with hierarchical pore carbon |
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 | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20221010 Address after: 276000 South Innovation and Entrepreneurship Science Park, the intersection of Huashan Road and South Outer Ring Road, Jiehu Street, Yinan County, Linyi City, Shandong Province Patentee after: Shandong Huihai Membrane Material Technology Co.,Ltd. Address before: 030024 No. 79 West Main Street, Taiyuan, Shanxi, Yingze Patentee before: Taiyuan University of Technology |
|
| TR01 | Transfer of patent right |