CN107983172A - Flat mixed-matrix forward osmosis membrane and preparation method based on metal organic framework MIL-100 (Fe) - Google Patents
Flat mixed-matrix forward osmosis membrane and preparation method based on metal organic framework MIL-100 (Fe) Download PDFInfo
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- CN107983172A CN107983172A CN201711330619.9A CN201711330619A CN107983172A CN 107983172 A CN107983172 A CN 107983172A CN 201711330619 A CN201711330619 A CN 201711330619A CN 107983172 A CN107983172 A CN 107983172A
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- 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
- B01D69/06—Flat membranes
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- 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
- B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
- B01D67/0011—Casting solutions therefor
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- 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
- B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
- B01D67/0013—Casting processes
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- 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
- B01D69/10—Supported membranes; Membrane supports
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- 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
- B01D71/08—Polysaccharides
- B01D71/12—Cellulose derivatives
- B01D71/14—Esters of organic acids
- B01D71/16—Cellulose acetate
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
- C02F1/445—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by forward osmosis
Abstract
The invention discloses a kind of flat mixed-matrix forward osmosis membrane and preparation method for being based on metal organic framework MIL 100 (Fe), belong to technical field of membrane separation.By 0.1%~2.0%（w/w）MIL 100 (Fe) be dispersed in 66.0%~90.9% by ultrasound（w/w）In the mixed solvent, then with 8.0%~20.0%（w/w）Cellulose acetate together, be added in a certain order in three neck round bottom flask, stirring be completely dissolved cellulose acetate after, add 1.0%~12.0%（w/w）Polyvinylpyrrolidone or polyethylene glycol 400 2~16h of stirring and dissolving is to being completely dissolved at a temperature of 25~90 DEG C, 3~16h of standing and defoaming, prepares forward osmosis membrane casting solution；Formed a film on backing material using phase inversion striking and 5~60mins is heat-treated in 30~90 DEG C of deionized waters, that is, the flat mixed-matrix forward osmosis membrane based on MIL 100 (Fe) is made.The made forward osmosis membrane of the present invention is by the use of 1M NaCl as driving liquid, deionized water as material liquid, and in the testing time of 1h, its pure water flux reaches 37.0L/m2More than h, reverse flux salt are less than 1.5g/m2•h。
Description
Technical field
The present invention relates to flat forward osmosis membrane of a kind of macromolecule and preparation method thereof, and metal is based on more particularly to one kind
The flat mixed-matrix forward osmosis membrane and preparation method of organic backbone MIL-100 (Fe).
Background technology
The scarcity of water resource and the water pollution of getting worse become the bottleneck for restricting social progress and economic development, new water
Source is developed and effluent sewage recycling also becomes global question of common concern.Since seawater resources are extremely abundant on the earth,
And substantial amounts of effluent sewage is produced, sea water desalination and sewage recycling become the strategic choice for solving water resources crisis.Many
Sea water desalination and sewage recycling technology in, membrane separation technique is one of best selection.As this key issue of solution
And be born low energy consumption, the positive infiltration technology of high Water Sproading rate into sea water desalination and sewage recycling field research emphasis and
Hot spot, to solving the problems, such as that shortage of water resources has important strategic importance.
Positive infiltration (forward osmosis, FO) is a kind of membrane separation technique driven by film both sides osmotic pressure, just
It is paid more and more attention, relevant theoretical and application study achieves larger progress, and is successfully applied to sea water desalination, at waste water
The field such as reason, food medicine, the energy.At present, common forward osmosis membrane mainly has cellulose acetate film, polybenzimidazole membrane, gathers
Acid amides composite membrane etc., degree of commercialization is not high to be mainly a lack of forward osmosis membrane of good performance and suitable driving liquid, and just oozes
Permeable membrane is the key point of whole positive process of osmosis.The close phase of structure of high performance forward osmosis membrane and its material character and film
Close, it is seen that it is particularly important that the membrane material and forward osmosis membrane preparation method of function admirable.Common forward osmosis membrane preparation method bounded
Three kinds of face polymerization, double selection tunic the preparation methods and nanofiltration membrane modifying.Concentration difference in positive osmosis composite membrane prepared by interfacial polymerization
Polarize more serious；Double selection tunics effectively reduce interior concentration polarization, but preparation process is complex；NF membrane Modified Membrane is to list
The rejection and water flux of valency salt are relatively low；Therefore, it is necessary to develop new forward osmosis membrane preparation process to improve forward osmosis membrane
Separating property and the feasibility of industrialization.
The last century 60's, foreign countries start the research of positive infiltration technology, using existing reverse osmosis membrane or NF membrane into
The application study that row is just permeating, as a result proves that existing reverse osmosis membrane or NF membrane are difficult to use in positive process of osmosis, but at the same time
Performance and membrane material, the membrane structure for demonstrating forward osmosis membrane are closely related；Then, all multimembrane scientific workers have started positive infiltration
The basic research of film preparation.Result of study shows, can be excellent with processability by selecting suitable membrane material, film-forming process
Forward osmosis membrane.The research of the positive infiltration technology in China is started late, and the current country aligns the research of infiltration technology, either film system
Standby or membrane process research, still in the exploratory stage.Some film researchers explore the preparation of cellulose family forward osmosis membrane
Condition, have studied influence of the various factors to forward osmosis membrane performance, but not yet prepare just oozing for commercially viable function admirable
Permeable membrane；The preparation and application study of forward osmosis membrane still shoulder heavy responsibilities.The studying enlightenments of early period we, changed using blending technology
Property membrane material, be expected to improve water flux, salt-stopping rate, mechanical performance and the anti-fouling performance of forward osmosis membrane, and be easily achieved production
Industry.Patent of invention ZL201410770001.4,201510245514.8 and ZL201410769752.4,201510245504.4
Nano-titanium dioxide and graphene is respectively adopted and prepares flat and doughnut forward osmosis membrane with acetyl cellulose blend, it is made
The separating property and permeance property of standby forward osmosis membrane have obtained raising by a relatively large margin；Patent of invention 2017100954795,
2017100954780th, 2017100954846 more excellent performance is prepared for using functionalized carbon nano-tube and acetyl cellulose blend
Forward osmosis membrane；But by selecting suitable material, the separating property and permeance property of prepared forward osmosis membrane can still be carried out
Further to improve, satisfaction is commercially produced and application demand.
It is new that metal organic framework (Metal-Organic Frameworks, MOFs) is that a kind of latest developments are got up
Material, also known as metal organic complex polymer, it is to pass through coordination group by the organic ligand and metal ion of oxygen-containing, nitrogen etc.
Fill the porous material of the infinite network structure formed.Compared to traditional inorganic porous material, MOFs materials possess zeolite, activity
The unrivaled excellent performance of the inorganic porous materials such as charcoal, carbon nanotubes, its Micropore volume are higher by several than above-mentioned porous material
Times, and have the characteristics that duct is variable, steady chemical structure.These excellent characteristics cause MOFs materials in gas storage, water
Body pollution thing adsorbing separation, gas catalysis etc. have huge application prospect.Metal organic framework is as a kind of new
Organic-inorganic hybrid material, the organic ligand in its structure help to improve the affinity between MOFs particles and polymer substrate,
It is preferable mixed substrate membrane containing nano-grade molecular sieve dispersed phase.Therefore, suitable MOFs materials and acetyl cellulose blend are such as prepared into mixed-matrix
Forward osmosis membrane, is expected to while high water flux, salt-stopping rate is obtained, also make forward osmosis membrane product have stain resistance, this is just
The research and development and application of permeable membrane material provide new thinking.
How while hydrophilic nmature is obtained, and make forward osmosis membrane that there is resistance tocrocking and keep the stabilization of water flux
Property, this is the problem that film scientific worker is thinking and studying always in recent years.The present invention is improved mixed using MIL-100 (Fe)
Structure and permeance property, the research of separating property of matrix forward osmosis membrane are closed, both at home and abroad there is not yet document report.
The content of the invention
The object of the present invention is to provide a kind of flat mixed-matrix based on metal organic framework MIL-100 (Fe) just
Permeable membrane, it is a further object to provide the preparation method of the mixed-matrix forward osmosis membrane.
To achieve the above object, the technical solution taken of the present invention is：
One kind is based on the flat mixed-matrix forward osmosis membrane of MIL-100 (Fe), is by the material composition of following mass percent
's：Polymeric film material 8.0%~20.0%（w/w）, pore-foaming agent 1.0%~12.0%（w/w）, MIL-100 (Fe) 0.1%~2.0%
（w/w）, solvent 66.0%~90.9%（w/w）；
The polymeric film material is one or both of cellulose diacetate and Triafol T, content for 8.0%~
20.0%（w/w）；
The metal organic framework MIL-100 (Fe) is self-control metal-organic framework materials, and shape is the less octahedral of particle diameter
Body crystal morphology, content are 0.1%~2.0%（w/w）；
The pore-foaming agent is polyvinylpyrrolidone and one kind of polyethylene glycol-400, and content is 1.0%~12.0%（w/w）；
The solvent is 1-methyl-2-pyrrolidinone and the mixed solvent of acetone, its volume ratio is 1-methyl-2-pyrrolidinone:Acetone=
1:0.1~7.0, content is 66.0%~90.9%（w/w）.
The preparation method of flat mixed-matrix forward osmosis membrane of the one kind based on metal organic framework MIL-100 (Fe), bag
Include following steps：
（1）A certain amount of MIL-100 (Fe) is added in the mixed solvent, is allowed to fully uniformly divide wherein using ultrasound
Dissipate, be added to after the completion of scattered in three neck round bottom flask, and add a certain amount of polymeric film material, stir evenly；
（2）A certain amount of pore-foaming agent is added in three neck round bottom flask, when stirring and dissolving 2~16 is small at a temperature of 25~90 DEG C
To being completely dissolved, the initial casting solution of the flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) is configured to；Then, will
Obtained casting solution removes bubble remaining in casting solution when static placement 3~16 is small at a temperature of stirring and dissolving；
（3）Supporting layer is laid in and cleans and on dry glass plate, then pours into a certain amount of casting solution on glass plate, is used
The striking of plate membrane scraper forms a film；After the nascent state film formed is evaporated 1~30 second at room temperature, 15~60 DEG C of constant temperature is immersed
Solidification forming in coagulating bath water tank, film shaping automatically disengages glass plate, after taking the film out in deionized water at normal temperature immersion 12~
48 it is small when, be then heat-treated 5~60 minutes in 30~90 DEG C of deionized water, that is, obtain the tablet based on MIL-100 (Fe)
Formula mixed-matrix forward osmosis membrane.
The supporting layer is one kind of polyester screen, non-woven fabrics, cotton yarn filter cloth, filter paper and nylon cloth, its aperture is 60
~280 mesh；
Evaporation time under the nascent state film room temperature, refers to that prepared flat forward osmosis membrane is completed after sky in knifing
Residence time in gas, evaporation time are 1~30 second；
The heat treatment temperature and time, refer to the deionization water temperature being heat-treated to prepared flat forward osmosis membrane
Degree and processing time, heat treatment temperature are 30~90 DEG C, and heat treatment time is 5~60 minutes；
The coagulating bath is deionized water.
The present invention provides a kind of flat mixed-matrix forward osmosis membrane for being based on metal organic framework MIL-100 (Fe)
And preparation method, MIL-100 (Fe) is incorporated into polymer and prepares mixed-matrix forward osmosis membrane, and assigns mixed-matrix just
The good permeance property of permeable membrane, separating property and antifouling property, this is the innovation of the present invention.Test result shows,
The pure water flux of prepared forward osmosis membrane and reverse flux salt have very big improvement.
The present invention is compared with prior art, has following beneficial effect：
（1）MIL-100 (Fe) provided by the present invention solves the problems, such as caving in for conventional metals organic backbone, its blending and modifying
Prepared flat mixed-matrix forward osmosis membrane and traditional Cellulose acetate forward osmotic membrane, the blending based on carbon nanotubes are just
Permeable membrane is compared, its pure water flux and reverse flux salt are obviously improved.
（2）MIL-100 (Fe) blending and modifying provided by the present invention prepares the side of flat mixed-matrix forward osmosis membrane
Method, equipment used is simple, easily-controllable, and film preparation technique is simple, assign while film forming prepared by the good infiltration of forward osmosis membrane
Performance, separating property and antifouling property, it is easy to accomplish industrialization.
Embodiment：
With reference to embodiment, the present invention is described in further detail, but the implementation of the present invention is not limited to this.
Embodiment 1：
By 0.6%（w/w）MIL-100 (Fe) be added to 54.4%（w/w）1-methyl-2-pyrrolidinone and 25.0%（w/w）Acetone group
Into in the mixed solvent, be allowed to fully dispersed wherein using ultrasound, three neck round bottom flask be added to after the completion of scattered
In, and add 13.0%（w/w）Cellulose acetate, stir evenly.By 7.0%（w/w）Polyethylene glycol-400 pore-foaming agent add
Into three neck round bottom flask, stirring and dissolving is configured to based on MIL-100 (Fe) for 8 hours to being completely dissolved at a temperature of 65 DEG C
The initial casting solution of flat mixed-matrix forward osmosis membrane；Then, put obtained casting solution is static at a temperature of stirring and dissolving
Put 9 it is small when, remove remaining bubble in casting solution.The polyester screen of 180 mesh is laid in and is cleaned and on dry glass plate, so
A certain amount of casting solution is poured on glass plate afterwards, is formed a film with the striking of plate membrane scraper；By the nascent state film formed in room temperature
After lower evaporation 10 seconds, solidification forming in 25 DEG C of constant temperature coagulating bath water tank is immersed, film shaping automatically disengages glass plate, takes the film out
When immersion 24 is small in deionized water at normal temperature afterwards, then it is heat-treated 15 minutes, that is, is based in 65 DEG C of deionized water
The flat mixed-matrix forward osmosis membrane of MIL-100 (Fe).By the use of 1MNaCl as driving liquid, deionized water as material liquid,
In the testing time of 1h, the pure water flux of prepared forward osmosis membrane reaches 37.0L/m2More than h, reverse flux salt are less than
1.5g/m2•h。
Embodiment 2：
The content of MIL-100 (Fe), 1-methyl-2-pyrrolidinone is adjusted to 0.1% respectively（w/w）With 54.9%（w/w）, remaining
With embodiment 1.Then the performance of the obtained flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) is：Utilize
1MNaCl is as driving liquid, and deionized water is as material liquid, in the testing time of 1h, the pure water flux of prepared forward osmosis membrane
Reach 26.0L/m2More than h, reverse flux salt are less than 2.5g/m2•h。
Embodiment 3：
The content of MIL-100 (Fe), 1-methyl-2-pyrrolidinone is adjusted to 2.0% respectively（w/w）With 53.0%（w/w）, remaining
With embodiment 1.Then the performance of the obtained flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) is：Utilize
1MNaCl is as driving liquid, and deionized water is as material liquid, in the testing time of 1h, the pure water flux of prepared forward osmosis membrane
Reach 36.0L/m2More than h, reverse flux salt are less than 2.0g/m2•h。
Embodiment 4：
Polyethylene glycol-400 in pore-foaming agent is changed to polyvinylpyrrolidone, remaining is the same as embodiment 1.It is then obtained
The performance of flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) is：Driving liquid, deionization are used as by the use of 1MNaCl
Water is as material liquid, and in the testing time of 1h, the pure water flux of prepared forward osmosis membrane reaches 32.0L/m2More than h, reversely
Flux salt is less than 1.5g/m2•h。
Embodiment 5：
Coagulation bath temperature is adjusted to 60 DEG C by 25 DEG C, remaining is the same as embodiment 1.It is then obtained based on MIL-100's (Fe)
The performance of flat mixed-matrix forward osmosis membrane is：By the use of 1MNaCl as driving liquid, deionized water is as material liquid, 1h's
In testing time, the pure water flux of prepared forward osmosis membrane reaches 41.0L/m2More than h, reverse flux salt are less than 2.5g/m2•h。
Embodiment 6：
Heat treatment temperature is adjusted to 90 DEG C by 65 DEG C, remaining is the same as embodiment 1.It is then obtained based on MIL-100's (Fe)
The performance of flat mixed-matrix forward osmosis membrane is：By the use of 1MNaCl as driving liquid, deionized water is as material liquid, 1h's
In testing time, the pure water flux of prepared forward osmosis membrane reaches 33.0L/m2More than h, reverse flux salt are less than 2.0g/m2•h。
Embodiment 7：
Heat treatment time was adjusted to 60 minutes by 15 minutes, remaining is the same as embodiment 1.It is then obtained based on MIL-100
(Fe) performance of high performance flat formula forward osmosis membrane is：By the use of 1MNaCl as driving liquid, deionized water as material liquid,
In the testing time of 1h, the pure water flux of prepared forward osmosis membrane reaches 35.0L/m2More than h, reverse flux salt are less than
1.5g/m2•h。
Comparative example 1：
By 55.0%（w/w）1-methyl-2-pyrrolidinone and 25.0%（w/w）The mixed solvent of acetone composition is added to three mouthfuls of round bottoms and burns
In bottle, 13.0% is then added（w/w）Cellulose acetate, stir evenly.By 7.0%（w/w）Polyethylene glycol-400 pore-foaming agent
It is added in three neck round bottom flask, stirring and dissolving is configured to flat acetate fiber in 8 hours to being completely dissolved at a temperature of 65 DEG C
The initial casting solution of plain mixed-matrix forward osmosis membrane；Then, by obtained casting solution, static placement 9 is small at a temperature of stirring and dissolving
When, remove bubble remaining in casting solution.The polyester screen of 180 mesh is laid in and is cleaned and on dry glass plate, then will
A certain amount of casting solution is poured on glass plate, is formed a film with the striking of plate membrane scraper；The nascent state film formed is steamed at room temperature
Hair immerses solidification forming in 25 DEG C of constant temperature coagulating bath water tank after 10 seconds, and film shaping automatically disengages glass plate, after taking the film out
When immersion 24 is small in deionized water at normal temperature, then it is heat-treated 15 minutes in 65 DEG C of deionized water, that is, obtains flat acetic acid
Cellulose mixed-matrix forward osmosis membrane.By the use of 1MNaCl as driving liquid, deionized water is as material liquid, in the testing time of 1h
In, the pure water flux of prepared forward osmosis membrane reaches 33.0L/m2More than h, reverse flux salt are less than 4.0g/m2•h。
Claims (10)
1. one kind is based on the flat mixed-matrix forward osmosis membrane of metal organic framework MIL-100 (Fe), it is characterised in that its
Contain metal organic framework MIL-100 (Fe) in casting solution, and influence the structure and performance of forward osmosis membrane；Casting solution is by following matter
Measure the material composition of percentage：Polymeric film material 8.0%~20.0%（w/w）, pore-foaming agent 1.0%~12.0%（w/w）、MIL-
100 (Fe) 0.1%~2.0%（w/w）, solvent 66.0%~90.9%（w/w）.
2. the flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) according to claim 1, its feature exist
In：The forward osmosis membrane is prepared using traditional phase inversion i.e. dry-wet method.
3. the flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) according to claim 1, its feature exist
In：The MIL-100 (Fe) is self-control metal organic framework, is the less octahedral crystal of particle, and content is 0.1%~2.0%
（w/w）.
4. the flat mixed-matrix forward osmosis membrane according to claim 1 based on MIL-100 (Fe), it is characterised in that：
The cellulose acetate is one or both of cellulose diacetate and Triafol T.
5. the flat mixed-matrix forward osmosis membrane according to claim 1 based on MIL-100 (Fe), it is characterised in that：
The pore-foaming agent is polyvinylpyrrolidone and one kind of polyethylene glycol-400, and content is 1.0%~12.0%（w/w）.
6. the flat mixed-matrix forward osmosis membrane according to claim 1 based on MIL-100 (Fe), it is characterised in that：
The solvent is 1-methyl-2-pyrrolidinone and the mixed solvent of acetone, its volume ratio is 1-methyl-2-pyrrolidinone：Acetone=1:0.1
~7.0, content is 66.0%~90.9%（w/w）.
7. the preparation method of flat mixed-matrix forward osmosis membrane of the one kind based on metal organic framework MIL-100 (Fe), it is special
Sign is that it includes：
（1）A certain amount of MIL-100 (Fe) is added in the mixed solvent, is allowed to fully uniformly divide wherein using ultrasound
Dissipate, be added to after the completion of scattered in three neck round bottom flask, and add a certain amount of polymeric film material, stir evenly；
（2）A certain amount of pore-foaming agent is added in three neck round bottom flask, when stirring and dissolving 2~16 is small at a temperature of 25~90 DEG C
To being completely dissolved, the initial casting solution of the flat mixed-matrix forward osmosis membrane based on MIL-100 (Fe) is configured to；Then, will
Obtained casting solution removes bubble remaining in casting solution when static placement 3~16 is small at a temperature of stirring and dissolving；
（3）Supporting layer is laid in and cleans and on dry glass plate, then pours into a certain amount of casting solution on glass plate, is used
The striking of plate membrane scraper forms a film；After the nascent state film formed is evaporated 1~30 second at room temperature, 15~60 DEG C of constant temperature is immersed
Solidification forming in coagulating bath water tank, film shaping automatically disengages glass plate, after taking the film out in deionized water at normal temperature immersion 12~
48 it is small when, be then heat-treated 5~60 minutes in 30~90 DEG C of deionized water, that is, obtain the tablet based on MIL-100 (Fe)
Formula mixed-matrix forward osmosis membrane.
8. the preparation method of the flat mixed-matrix forward osmosis membrane according to claim 7 based on MIL-100 (Fe),
It is characterized in that：The supporting layer is one kind of polyester screen, non-woven fabrics, cotton yarn filter cloth, filter paper and nylon cloth, its aperture is
60~280 mesh；The coagulating bath is deionized water.
9. the preparation method of the flat mixed-matrix forward osmosis membrane according to claim 7 based on MIL-100 (Fe),
It is characterized in that：Evaporation time under the nascent state film room temperature is 1~30 second.
10. the preparation method of the flat mixed-matrix forward osmosis membrane according to claim 7 based on MIL-100 (Fe),
It is characterized in that：The heat treatment temperature is 30~90 DEG C, and the heat treatment time is 5~60 minutes.
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|---|---|---|---|---|
| CN110681271A (en) * | 2019-11-12 | 2020-01-14 | 东北师范大学 | NH2-MIL-125/POD-COOH ultrathin homogeneous hybrid forward osmosis membrane and preparation method thereof |
| CN113209952A (en) * | 2021-05-08 | 2021-08-06 | 中国药科大学 | Chiral covalent organic framework membrane and preparation method and application thereof |
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