CN108939949B - Polyimide affinity membrane with high adsorption performance on bilirubin and preparation method thereof - Google Patents
Polyimide affinity membrane with high adsorption performance on bilirubin and preparation method thereof Download PDFInfo
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- CN108939949B CN108939949B CN201810780596.XA CN201810780596A CN108939949B CN 108939949 B CN108939949 B CN 108939949B CN 201810780596 A CN201810780596 A CN 201810780596A CN 108939949 B CN108939949 B CN 108939949B
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- polyimide
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- 239000012528 membrane Substances 0.000 title claims abstract description 57
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 title claims abstract description 36
- 239000004642 Polyimide Substances 0.000 title claims abstract description 31
- 229920001721 polyimide Polymers 0.000 title claims abstract description 31
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 25
- 238000000614 phase inversion technique Methods 0.000 claims abstract description 9
- 239000002131 composite material Substances 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 239000011148 porous material Substances 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- 239000004745 nonwoven fabric Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- -1 polypropylene Polymers 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- 229910021389 graphene Inorganic materials 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- OYCWBLFDGYRWSR-UHFFFAOYSA-N [Co][Fe][Sr][La] Chemical compound [Co][Fe][Sr][La] OYCWBLFDGYRWSR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 2
- 238000007654 immersion Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 239000005543 nano-size silicon particle Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims 1
- 238000004132 cross linking Methods 0.000 abstract description 7
- 230000004907 flux Effects 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- 229920001108 Polyimide P84 Polymers 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001042 affinity chromatography Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- External Artificial Organs (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention belongs to the technical field of preparation of affinity membranes, and relates to a polyimide affinity membrane with high adsorption performance to bilirubin and a preparation method thereof. The invention adopts polyimide with a large amount of active carboxyl as a main membrane material, adopts a phase inversion method to prepare the polyimide membrane with a porous structure, and obtains the affinity membrane with a large amount of amino or hydroxyl through high-temperature crosslinking treatment. The invention is helpful to greatly simplify the preparation steps of the affinity membrane, simultaneously remarkably improve the density of active groups, keep higher permeation flux, and realize high-efficiency adsorption and separation of bilirubin, thereby realizing large-scale application. The method has simple process flow, and the prepared affinity membrane contains a large amount of amino or hydroxyl, so that the prepared polyimide affinity membrane has good bilirubin adsorption capacity, mechanical stability and chemical stability, and uniform membrane pore size, and the composite affinity membrane can be widely applied to the removal of bilirubin in blood.
Description
Technical Field
The invention belongs to the technical field of preparation of affinity membranes, and particularly relates to a preparation method of a high-flux porous affinity membrane with high adsorption performance on bilirubin.
Background
The separation process generally occupies 30-60% of the cost of biological separation, and biological macromolecules generally have biological activity, are sensitive to separation media, have poor thermal stability and low concentration and are difficult to purify. The affinity membrane technology is a novel separation technology combining membrane separation and affinity chromatography, feed liquid flows through membrane pores in a convection mode, and internal diffusion resistance is avoided, so that the operation speed can be improved to the maximum extent on the premise of not influencing adsorption binding action. Due to the outstanding advantages of affinity membrane separation technology, the application of the affinity membrane separation technology in the fields of biology, medicine, beverages and the like is deeply researched recently. Adsorption and flux of affinity membranes are key factors affecting membrane performance, and how to improve separation selectivity and permeation flux of the membranes becomes a hot point of research.
The processes of ultrafiltration, nanofiltration and reverse osmosis membrane preparation often use polyimide materials because of their high heat resistance, solvent resistance and chemical stability. Polyimide (P84) contains a large number of carboxyl groups in the molecule, has high reactivity, and can react with small molecules or single molecules containing amino or hydroxyl groups, so that high molecules with more affinity groups are obtained. At present, no affinity membrane for bilirubin separation is reported, which is prepared from a polyimide material and subjected to membrane modification by using a crosslinking agent.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a polyimide affinity membrane which is easy to prepare. The invention adopts polyimide (P84) with a large amount of active carboxyl as a main membrane material, adopts a phase inversion method to prepare the polyimide membrane with a porous structure, and carries out high-temperature crosslinking treatment on commercial polyethylene glycol, polyethylene imine, 2, 4, 6-triaminopyrimidine, hexamethylenetetramine, Congo red and the like to obtain the affinity membrane with a large amount of amino or hydroxyl. The invention is helpful to greatly simplify the preparation steps of the affinity membrane, simultaneously remarkably improve the density of active groups, keep higher permeation flux, and realize high-efficiency adsorption and separation of bilirubin, thereby realizing large-scale application.
The technical scheme of the invention is as follows:
a polyimide affinity membrane with high adsorption performance to bilirubin has an asymmetric structure and comprises a separation and adsorption functional layer and a supporting layer, wherein the supporting layer is positioned below the separation and adsorption functional layer;
the separation and adsorption function layer is an ultrathin porous membrane formed by a phase inversion method, and the thickness of the separation and adsorption function layer is within 200 nm; the components of the ultrathin porous membrane comprise polyimide (p84), an additive, a cross-linking agent and a solvent;
the additive is one or more of nano silicon oxide, aluminum oxide, titanium oxide, ferroferric oxide, lanthanum strontium cobalt iron, a molecular sieve, graphene, polyethylene glycol, polyvinylpyrrolidone, graphene, inorganic salt such as lithium chloride, sodium chloride and sodium sulfate;
the cross-linking agent is one or a mixture of more than two of polyethylene glycol, polyethyleneimine, 2, 4, 6-triaminopyrimidine, hexamethylenetetramine and Congo red, and the mass percentage concentration of the cross-linking agent in the system is 0.2-5%;
the solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide;
the supporting layer is a polyester or polypropylene non-woven fabric, the thickness of the supporting layer is 50-500 mu m, and the pore diameter is 0.1-10 mu m.
A preparation method of a polyimide affinity membrane with high adsorption performance to bilirubin comprises the following steps:
(1) separation and adsorption functional layer for preparing porous affinity membrane
Adopting polyester or polypropylene non-woven fabric with nominal aperture of 0.1-10 microns as a base film; dissolving polyimide (p84) with the mass percent of 5-15% in a strong polar solvent to prepare a casting solution; then adding an additive with the total mass fraction of 0-8% to form a porous structure; stirring uniformly to obtain uniform polymer solution or dispersion, standing for defoaming, preparing a composite film on the non-woven fabric by adopting an immersion precipitation phase inversion method, and storing in deionized water;
(2) preparation of polyimide affinity membrane with adsorption and separation functions
Soaking the prepared composite membrane in 0.2-5% cross-linking agent water solution at 25-80 deg.C for 10-30 min to obtain polyimide affinity membrane with adsorption and separation functions, washing with deionized water, and storing.
The invention has the beneficial effects that: the method has simple process flow, and the prepared affinity membrane contains a large amount of amino or hydroxyl, so that the prepared polyimide affinity membrane has good bilirubin adsorption capacity, mechanical stability and chemical stability, the membrane aperture is uniform, and the composite affinity membrane can be widely applied to the removal of bilirubin in blood.
Detailed Description
The following further describes the specific embodiments of the present invention in combination with the technical solutions.
Example 1
5g of P84 is dissolved in 45g of N, N-dimethylformamide solution to prepare polyimide solution with the mass percent of 10%, membrane formation is carried out by adopting a phase inversion method, then deionized water is used for soaking, the polyimide solution is added into polyethylene glycol solution with the mass percent of 0.5% for crosslinking, and crosslinking is carried out for 30 minutes at the temperature of 50 ℃. The adsorption capacity of the prepared affinity membrane on 100mg/L bilirubin is 23mg/g, inFlux at 0.1MPa is 687L/m2h。
Example 2
6g P84 is dissolved in 49gN, N-dimethylformamide solution, 1g of lithium chloride is added to prepare polyimide solution with the mass percent of 12%, the polyimide solution is soaked in deionized water after film formation by a phase inversion method, the deionized water is added into 2, 4, 6-triaminopyrimidine solution with the mass percent of 0.5% to carry out crosslinking, and the crosslinking is carried out for 30 minutes at the temperature of 40 ℃. The prepared affinity membrane has an adsorption capacity of 42mg/g for 100mg/L bilirubin and a flux of 573L/m under 0.1MPa2h。
Example 3
6g P84 is dissolved in 49gN, N-dimethylformamide solution, and 1g of polyvinylpyrrolidone is added to prepare polyimide solution with the mass percent of 12%, the polyimide solution is soaked in deionized water after film formation by a phase inversion method, and then the polyimide solution is added into Congo red solution with the mass percent of 0.1% to be crosslinked, and the crosslinking is carried out for 30 minutes at the temperature of 50 ℃. The prepared affinity membrane has an adsorption capacity of 40mg/g for 50mL of 100mg/L bilirubin and a flux of 406L/m under 0.1MPa2h。
Claims (1)
1. A preparation method of a polyimide affinity membrane with high adsorption performance to bilirubin is characterized in that the polyimide affinity membrane with high adsorption performance to bilirubin has an asymmetric structure and comprises a separation and adsorption functional layer and a supporting layer, wherein the supporting layer is positioned below the separation and adsorption functional layer;
the separation and adsorption function layer is an ultrathin porous membrane formed by a phase inversion method, and the thickness of the separation and adsorption function layer is within 200 nm; the components of the ultrathin porous membrane comprise polyimide, an additive, a cross-linking agent and a solvent;
the polyimide is P84, and the molecule of the polyimide contains a large amount of reactive carboxyl groups;
the additive is one or more than two of nano silicon oxide, aluminum oxide, titanium oxide, ferroferric oxide, lanthanum strontium cobalt iron, a molecular sieve, graphene, polyethylene glycol, polyvinylpyrrolidone, lithium chloride, sodium chloride and sodium sulfate;
the cross-linking agent is one or a mixture of more than two of polyethylene glycol, polyethyleneimine, 2, 4, 6-triaminopyrimidine, hexamethylenetetramine and Congo red, and the mass percentage concentration of the cross-linking agent in the system is 0.2-5%;
the solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide;
the supporting layer is a polyester or polypropylene non-woven fabric, the thickness of the supporting layer is 50-500 mu m, and the pore diameter is 0.1-10 mu m;
the preparation method comprises the following steps:
(1) separation and adsorption functional layer for preparing porous affinity membrane
Adopting polyester or polypropylene non-woven fabric with nominal aperture of 0.1-10 microns as a base film; dissolving polyimide with the mass percent of 5-15% in a strong polar solvent to prepare a membrane casting solution; then adding an additive with the total mass fraction of 0-8% to form a porous structure; stirring uniformly to obtain a uniform polymer solution, standing for defoaming, preparing a composite membrane on the non-woven fabric by adopting an immersion precipitation phase inversion method, and storing in deionized water;
(2) preparation of polyimide affinity membrane with adsorption and separation functions
Soaking the prepared composite membrane in a cross-linking agent water solution for 10-30 minutes at an operation temperature of 25-80 ℃ to obtain the polyimide affinity membrane with the adsorption and separation functions, and finally washing the polyimide affinity membrane with deionized water for storage and use.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810780596.XA CN108939949B (en) | 2018-07-17 | 2018-07-17 | Polyimide affinity membrane with high adsorption performance on bilirubin and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810780596.XA CN108939949B (en) | 2018-07-17 | 2018-07-17 | Polyimide affinity membrane with high adsorption performance on bilirubin and preparation method thereof |
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| CN108939949A CN108939949A (en) | 2018-12-07 |
| CN108939949B true CN108939949B (en) | 2021-06-08 |
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| CN109985608A (en) * | 2019-04-17 | 2019-07-09 | 辽宁石油化工大学 | Cellulose acetate/polyethyleneimine-ciba blue F3GA film and its preparation method and application |
| CN118084761B (en) * | 2024-04-28 | 2024-07-16 | 吉林浩泰健康产业发展股份有限公司 | Method for extracting bovine bilirubin |
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|---|---|---|---|---|
| WO2014125298A1 (en) * | 2013-02-18 | 2014-08-21 | Fujifilm Manufacturing Europe Bv | Gas separation membranes |
| CN105709616A (en) * | 2016-03-09 | 2016-06-29 | 中国海洋大学 | Method for preparing organic-solvent-resistant ultrafiltration membrane, prepared ultrafiltration membrane and application of ultrafiltration membrane |
| CN106582318A (en) * | 2016-12-20 | 2017-04-26 | 南京工业大学 | Organic solvent-resistant nanofiltration membrane modified by graphene oxide, and preparation method and application thereof |
| CN107261869A (en) * | 2016-04-08 | 2017-10-20 | 财团法人纺织产业综合研究所 | Polyimide composition and method for producing separation membrane |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57177303A (en) * | 1982-01-18 | 1982-11-01 | Nitto Electric Ind Co Ltd | Selective permeable film |
| US20030126990A1 (en) * | 2001-12-20 | 2003-07-10 | Koros William J. | Crosslinked and crosslinkable hollow fiber membrane and method of making same |
| CN100593520C (en) * | 2006-05-26 | 2010-03-10 | 中国科学院化学研究所 | Polyimide copolymer infiltration vaporization separation film for treating phenols-containing waste water and preparing method thereof |
| CN106890571A (en) * | 2017-03-06 | 2017-06-27 | 江苏凯米膜科技股份有限公司 | A kind of preparation method of organic tubular nanofiltration membrane |
| CN107469637A (en) * | 2017-07-14 | 2017-12-15 | 中国海洋大学 | A kind of preparation method of high flux solvent-resistant polyimide hybrid composite membrane |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014125298A1 (en) * | 2013-02-18 | 2014-08-21 | Fujifilm Manufacturing Europe Bv | Gas separation membranes |
| CN105709616A (en) * | 2016-03-09 | 2016-06-29 | 中国海洋大学 | Method for preparing organic-solvent-resistant ultrafiltration membrane, prepared ultrafiltration membrane and application of ultrafiltration membrane |
| CN107261869A (en) * | 2016-04-08 | 2017-10-20 | 财团法人纺织产业综合研究所 | Polyimide composition and method for producing separation membrane |
| CN106582318A (en) * | 2016-12-20 | 2017-04-26 | 南京工业大学 | Organic solvent-resistant nanofiltration membrane modified by graphene oxide, and preparation method and application thereof |
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