CN113457460B - Selective molecular filtering membrane material and preparation method and application thereof - Google Patents
Selective molecular filtering membrane material and preparation method and application thereof Download PDFInfo
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- CN113457460B CN113457460B CN202110740524.4A CN202110740524A CN113457460B CN 113457460 B CN113457460 B CN 113457460B CN 202110740524 A CN202110740524 A CN 202110740524A CN 113457460 B CN113457460 B CN 113457460B
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- 238000001914 filtration Methods 0.000 title claims abstract description 31
- 239000012528 membrane Substances 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 238000007731 hot pressing Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- -1 polyethylene Polymers 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 239000002033 PVDF binder Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract description 6
- 238000013329 compounding Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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
- B01D71/26—Polyalkenes
-
- 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
-
- 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
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
- B01D71/34—Polyvinylidene fluoride
-
- 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
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
- B01D71/36—Polytetrafluoroethene
-
- 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
- B01D71/48—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
Abstract
The invention discloses a selective molecular filtering membrane material, a preparation method and application thereof, and belongs to the technical field of filtering membrane materials. The invention firstly provides a compound for preparing a molecular filtering membrane material, which is prepared by reacting polyvinyl alcohol with a cyclic compound under the action of a catalyst, and then compounding the compound with a substrate to prepare the molecular filtering membrane material. The nonpolar macrocyclic compound has stable structure, can well pass through the annular hole when the radius of nonpolar molecules is smaller than the aperture of the macrocyclic compound, and molecules with the radius larger than the aperture and polar molecules cannot pass through the annular hole, so that the purpose of selectively separating the nonpolar molecules is achieved, and the nonpolar macrocyclic compound is compounded with a base material and is used as a filtering membrane material for selectively separating molecular levels, thereby having good application prospect.
Description
Technical Field
The invention belongs to the technical field of filtering membrane materials, and particularly relates to a molecular filtering membrane material, a preparation method and application thereof.
Background
At present, the membrane separation technology is mainly applied to metal ion exchange and filtration, biological cell filtration and suspended matter separation, and for molecular-level filtration, molecular-level filtration is mainly realized by chromatographic columns, and the use of a molecular filtration membrane for separating molecules with different polarities is less reported, but the membrane separation has great advantages in application compared with the chromatographic column separation, so that the development of the molecular filtration membrane has important significance.
Disclosure of Invention
The invention solves the problems in the prior art by providing a compound for preparing a selective molecular filtration membrane material, which is used as the main component of a filtration layer of the filtration membrane material and is prepared by reacting polyvinyl alcohol with a cyclic compound PBCD under the action of a catalyst, and is named as PVA-PBCD, and has the following structure
Wherein the cyclic compound PBCD has the following structure->
Wherein R is-OH, -CH 2 OH or-C 2 H 4 OH。
The invention further provides a preparation method of the compound, PVA and PBCD are used as raw materials, the reaction temperature is 70-110 ℃ and the reaction time is 60-300min under the action of a catalyst, and the preparation route is as follows:
wherein the catalyst for the reaction is benzenesulfonic acid, benzenesulfonic acid derivatives, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
Wherein, the dosage of PVA is 6:1-3:2 according to the mass ratio of-CHOH-and PBCD in PVA.
Preferably, PVA is used in the amount of PVA1799 according to 180g PVA1799 and 1.03mol PBCD.
Wherein the cyclic compound PBCD is prepared by reacting a compound HQ-R with formaldehyde under the action of a template agent and a catalyst at 50-150 ℃ for 30-240 min, and the structure of the compound HQ-R is as follows
Wherein R is-OH, -CH 2 OH or-C 2 H 4 OH, the synthetic route is as follows:
wherein, the catalyst in the preparation reaction of the cyclic compound PBCD is benzenesulfonic acid, benzenesulfonic acid derivatives, strong acid ion exchange resin, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
Wherein, the template agent in the preparation reaction of the cyclic compound PBCD is 100-200 nm calcium carbonate or football alkene.
Wherein, the molar ratio of the compound HQ-R to formaldehyde in the preparation reaction of the cyclic compound PBCD is 1:1-1:1.1.
The invention further provides a molecular filtering membrane material, which comprises a filtering layer and a base material which take the compound PVA-PBCD as a main component, wherein the base material is a polyethylene fiber membrane, a polyester PET fiber membrane, a polyvinylidene fluoride PDVF membrane or a polytetrafluoroethylene PTEF membrane.
The invention further discloses a preparation method of the molecular filtering membrane material, PVA-PBCD is dispersed in a solvent, then the PVA-PBCD is coated on the surface of a base material, and after drying, the PVA-PBCD is attached to the surface of the base material through hot-pressing and hot-melting.
Among them, DMF, acetone or DMSO may be used as the solvent.
Preferably, 1 part of PVA-PBCD is dissolved in 3 to 10 parts of DMF, acetone or DMSO in parts by weight.
Preferably, the thickness of the surface coating of the substrate is controlled to be 0.1-1.2 mm.
Preferably, the drying condition is drying at 50-110 ℃ for 30-150 min.
Preferably, the hot pressing condition is that the hot pressing is carried out for 5-15 min at 120-180 ℃.
The invention further discloses application of the molecular filtering membrane material, which is used for separating nonpolar molecules and polar molecules in the mixed solution.
The invention has the beneficial effects that:
the nonpolar macrocyclic compound with stable structure can well pass through the annular ring when the radius of nonpolar molecules is smaller than the aperture of the macrocyclic compound, and molecules with the radius larger than the aperture and polar molecules cannot pass through the annular ring, so that the purpose of selectively separating nonpolar or weak polar molecules is achieved;
according to the invention, the nonpolar macrocyclic compound with a certain radius is reacted with PVA, so that the density and uniformity of the cyclic compound are increased, and the cyclic compound is compounded with a base material and then used as a filtering membrane material for selective separation of molecular level, thus the method has a good application prospect.
Drawings
FIG. 1 is a cyclic compound of example 1 1 H NMR spectrum;
FIG. 2 is a schematic diagram of a molecular filtration membrane of example 3.
Detailed Description
Example 1
By a compound HQ-R (R is-CH 2 OH) and formaldehyde are used as raw materials, the dosage of the raw materials is 1 part and 1.05 part by weight, the heating temperature is controlled to be 50-150 ℃ under the conditions of 1.1 part of template agent and 0.25 catalyst, the reaction time is controlled to be 30-120 min, the cyclic compound (1, 3,5,7,9 (1, 4) -pentabenzenazenacyclodecaphane) is prepared, the template agent adopts calcium carbonate microspheres, the catalyst adopts benzenesulfonic acid, the cyclic compound with the following structure is obtained, 1 the H NMR spectrum is shown in FIG. 1.
Example 2
The compound PVA-PBCD is produced by using polyvinyl alcohol PVA1799 (180 g) and the cyclic compound (1.03 mol) prepared in the embodiment 1 as raw materials under the catalysis of concentrated sulfuric acid, wherein the reaction temperature is controlled between 70 and 110 ℃, and the reaction time is controlled between 60 and 120 minutes.
Example 3
The PVA-PBCD prepared in example 2 is dispersed in solvent, then coated on the surface of the substrate, the thickness of the coating is 0.1-1.2 mm, and after drying for 30-150 min at 50-110 ℃, hot-pressing at 120-180 deg.c for 5-15 min to adhere the two materials tightly via hot melting to raise the mechanical performance and prolong the service life of the material.
Application test case
The molecular filtration membrane prepared in example 3 was used for the selective separation of ethyl acetate in a mixture containing ethyl acetate, acetic acid, ethanol and water, and the test results were as follows:
1. the mixture of ethyl acetate and ethanol water=90:2:5:3 was separated to give a weak polar ethyl acetate liquid having a purity of 99.26% and a polar solution.
2. The mixture of butyl acetate: acetic acid: butanol: water=84:5:8:3 was separated to obtain a weak polar ethyl acetate liquid of 98.82% purity and a polar solution.
3. The mixture of ethyl formate to formic acid to ethanol to water=88:2:6:4 was separated to give a weak polar ethyl acetate liquid having a purity of 99.11% and a polar solution.
The foregoing is a further detailed description of the invention in connection with specific/preferred embodiments, and it is not intended that the invention be limited to such description. It is also possible to make several alternatives or modifications to the described embodiments without departing from the inventive concept, which alternatives or modifications are to be considered as falling within the scope of the invention.
Claims (10)
1. A compound for use in the preparation of a selective molecular filtration membrane material, characterized in that: the compound is used as the main component of a filtering layer of a filtering membrane material, is prepared by reacting polyvinyl alcohol with a cyclic compound PBCD under the action of a catalyst, is named PVA-PBCD, and has the following structure
The cyclic compound PBCD has the following structure
Wherein R' is obtained by reacting R, which is-CH 2 OH or-C 2 H 4 OH。
2. A process for the preparation of a compound as claimed in claim 1, characterized in that: PVA and PBCD are used as raw materials, the reaction temperature is 70-110 ℃ and the reaction time is 60-300min under the action of a catalyst, and the preparation method is as follows
3. A process for the preparation of a compound according to claim 2, characterized in that: the reaction is carried out under the action of a catalyst, wherein the catalyst is benzenesulfonic acid, benzenesulfonic acid derivatives, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
4. A process for the preparation of a compound according to claim 2, characterized in that: the mass ratio of the-CHOH-to the PBCD in the PVA is 6:1-3:2.
5. The method for producing a compound according to any one of claims 2 to 4, wherein: the cyclic compound PBCD is prepared by reacting a compound HQ-R with formaldehyde under the action of a catalyst and a template agent at 50-150 ℃ for 30-240 min, wherein the structure of the compound HQ-R is as follows
Wherein R is-CH 2 OH or-C 2 H 4 OH。
6. The method for producing a compound according to claim 5, wherein: the catalyst is benzenesulfonic acid, benzenesulfonic acid derivatives, strong acid ion exchange resins, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid; the template agent is 100-200 nm calcium carbonate or football alkene.
7. The method for producing a compound according to claim 5, wherein: the molar ratio of the compound HQ-R to formaldehyde is 1:1-1:1.1.
8. A selective molecular filtration membrane material is characterized in that: a filter layer and a substrate which take the compound PVA-PBCD as a main component, wherein the substrate is a polyethylene fiber film, a polyester PET fiber film, a polyvinylidene fluoride PDVF film or a polytetrafluoroethylene PTEF film.
9. The method for preparing the molecular filtration membrane material according to claim 8, wherein: PVA-PBCD is dispersed in a solvent, then coated on the surface of a substrate, dried and then adhered on the surface of the substrate through hot-pressing and hot-melting.
10. The use of the molecular filtration membrane material of claim 8 for separating nonpolar molecules from polar molecules in a mixed solution.
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|---|---|---|---|---|
| US4846977A (en) * | 1986-10-21 | 1989-07-11 | The Dow Chemical Company | Method and device for separating polar from non-polar liquids using membranes |
| US5156740A (en) * | 1982-06-01 | 1992-10-20 | Gft Ingenieurburo Fur Industrieanlagenbau | Multi-layer membrane and the use thereof for the separation of liquid mixtures according to the pervaporation process |
| US5276088A (en) * | 1990-05-21 | 1994-01-04 | Toppan Printing Co., Ltd. | Method of synthesizing cyclodextrin polymers |
| WO2000074828A1 (en) * | 1999-06-03 | 2000-12-14 | Gkss-Forschungszentrum Geesthacht Gmbh | Hydrophilic composite membrane for dehydrating organic solutions |
| EP1468723A1 (en) * | 2003-04-16 | 2004-10-20 | Millipore Corporation | Crosslinked cellulosic membrane |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102014105085B4 (en) * | 2014-04-09 | 2022-01-27 | Buergofol GmbH | Polymer multi-layer film and its use, tubular lining structure with the polymer multi-layer film and rehabilitated sewer section with the tubular lining structure |
| CN104826506B (en) * | 2015-05-18 | 2017-02-22 | 天津工业大学 | Beta-cyclodextrin grafted polymer chiral separation membrane and preparation method thereof |
| AU2019243422A1 (en) * | 2018-03-26 | 2020-09-24 | University Of Georgia Research Foundation, Inc. | Pharmaceutical compositions containing polyrotaxanes |
| EP3860743A4 (en) * | 2018-10-02 | 2022-06-22 | The Penn State Research Foundation | Thin-film composite membrane and methods of making and using the same |
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|---|---|---|---|---|
| US5156740A (en) * | 1982-06-01 | 1992-10-20 | Gft Ingenieurburo Fur Industrieanlagenbau | Multi-layer membrane and the use thereof for the separation of liquid mixtures according to the pervaporation process |
| US4846977A (en) * | 1986-10-21 | 1989-07-11 | The Dow Chemical Company | Method and device for separating polar from non-polar liquids using membranes |
| US5276088A (en) * | 1990-05-21 | 1994-01-04 | Toppan Printing Co., Ltd. | Method of synthesizing cyclodextrin polymers |
| WO2000074828A1 (en) * | 1999-06-03 | 2000-12-14 | Gkss-Forschungszentrum Geesthacht Gmbh | Hydrophilic composite membrane for dehydrating organic solutions |
| EP1468723A1 (en) * | 2003-04-16 | 2004-10-20 | Millipore Corporation | Crosslinked cellulosic membrane |
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| Title |
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| PVA/PAN渗透汽化膜分离乙酸乙酯―乙醇―水体系的研究;郑金花;许振良;李井峰;魏永明;;膜科学与技术(01);第56-60页 * |
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