CN103585903A - Chiral-separation solid membrane grafted by chiral identification body through dopamine pretreatment, and making method thereof - Google Patents
Chiral-separation solid membrane grafted by chiral identification body through dopamine pretreatment, and making method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of polymer membrane materials, and discloses a chiral-separation solid membrane grafted by a chiral identification body through dopamine pretreatment, and a making method and an application thereof. The method includes the following concrete steps: 1, immersing a solid membrane in a dopamine solution, stirring for reacting, and flushing with clear water; and 2, immersing the flushed solid membrane in a solution of the chiral identification body, heating for reacting, washing, and carrying out vacuum drying to obtain the chiral-separation solid membrane grafted by the chiral identification body through dopamine pretreatment. Firm and stable fctive function groups comprising -NH2, -OH and -C=O are introduced to the surface of the solid membrane through the above immersion technology; and chiral recognition sites are introduced to the surface of the solid membrane through the above immersion technology without influencing the structure or performances of the membrane, so the chiral-separation solid membrane grafted by the chiral identification body through dopamine pretreatment can be used for the effective separation of racemes The making method has the advantages of realization of the implementation of above reactions in an aqueous solution for a whole course, and mild and unharsh reaction conditions, development of the modification selectivity of the solid membrane, simple process, and easy realization of the industrialized batch production.
Description
Technical field
The invention belongs to macromolecule member material technical field, particularly chiral separation solid film of a kind of dopamine pretreatment grafting chiral Recognition body and its preparation method and application.
Background technology
In modern pharmaceutical industry, chirality more and more obtains everybody attention.This is mainly to have different pharmacologically actives, different pharmacokinetics and drug effect because people understand enantiomer in racemic modification medicine gradually.Human body is selected particularly responsive to chirality, after the different enantiomer in racemic drug and the interaction of human organ, separately carried out separately metabolism, thereby obtain different pharmacologically actives by different approach.Therefore, the result for the treatment of that perhaps a kind of enantiomer can obtain wanting, yet another kind be perhaps not only of no curative effect, worse, may obtain not wanting the result of seeing.Just there is such tragedy in nineteen sixty, n-phthalyl-glutamic acid acid imide is pushed to the market as a kind of tranquillizer, and finding afterwards only has R-enantiomer to have result for the treatment of, and S-enantiomer does not only have result for the treatment of, also causes fetal anomaly.Within 1992, U.S. food drug safety office has just promulgated the regulations about chiral drug, has the enantiomer of result for the treatment of just can render to market, and every kind of enantiomer of drugs should carry out respectively the research of pharmacology and metabolic pathway.Now, optical voidness pharmaceutical requirements grows with each passing day, so the chirality of medicine is synthetic with separated, and the mankind are had to formidable important meaning.
Embrane method resolving chiral enantiomer has low cost, low energy consumption, successive operation mode and is easy to the advantages such as scale, is generally considered and carries out one of very potential method of extensive chiral resolution, has a good application prospect.Therefore, chiral resolution membrane technology has caused domestic and international research worker's extensive concern, and becomes the new focus of hymenology circle research.
At present film being carried out the research of chirality modification, is mainly by blend, compound, chemical modification, initiation grafting, light radiation grafting, low-temperature plasma grafting, enzyme initiation grafting etc.The method such as blend and chemical modification may change the physical property of original membrane matrix; After composite modified, coating potentially unstable is along with the carrying out of using, and composite bed departs from film base material gradually; And initiation grafting, higher according to costs such as radiation grafting, low-temperature plasma grafting, enzyme initiation graftings, treating capacity is little, unsuitable industrialization operation.
Summary of the invention
In order to overcome the shortcoming and deficiency of above-mentioned prior art, primary and foremost purpose of the present invention is to provide a kind of chiral separation solid film of dopamine pretreatment grafting chiral Recognition body, has accurately fixing chiral Recognition point on this chiral separation solid film.
Another object of the present invention is to provide the preparation method of the chiral separation solid film of above-mentioned dopamine pretreatment grafting chiral Recognition body.Preparation method of the present invention is by using the solid film of dopamine pretreatment, utilize dopamine under oxygen from polycondensation, firmly stick in the surface and fenestra of film, improve the hydrophily of film and also introduce reaction active groups; By schiff base reaction, allow chiral Recognition body react with the dopamine of polycondensation again, obtain the chiral separation solid film that chiral Recognition point is accurately fixed on film surface and fenestra.
The application of the chiral separation solid film that still a further object of the present invention is to provide above-mentioned dopamine pretreatment grafting chiral Recognition body in separation of racemic body.
Object of the present invention realizes by following proposal:
A preparation method for the chiral separation solid film of pretreatment grafting chiral Recognition body, comprises following concrete steps:
(1) will consolidate film and be soaked in dopamine solution, stirring reaction, clear water rinses;
(2) by after flushing admittedly film be soaked in chiral Recognition liquid solution, add thermal response, washing, vacuum drying, obtains the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body.
The described dopamine solution of step (1) refers to that dopamine concentration is the Tris buffer solution of pH8～9 of 1～5g/L.
The described chiral Recognition liquid solution of step (2) refers to that chiral Recognition bulk concentration is the Tris buffer solution of pH8～9 of 1～5g/L.
Preferably, described chiral Recognition body refers to containing amino chiral Recognition body.
More preferably, described chiral Recognition body refers to beta-amino-cyclodextrin (β-CD-NH
2) and bovine serum albumin (BSA) at least one.
The described stirring reaction of step (1) refers under room temperature exposure air, stirring reaction 12～48h.
Preferably, the described solid film of step (1) refers at least one in flat, doughnut formula and the solid film of tubulose.
More preferably, described solid film refers at least one in PS membrane, polyvinylidene fluoride film, poly tetrafluoroethylene, polypropylene screen, cellulose membrane, polyacrylonitrile film, poly (ether sulfone) film and polyester film.
The thermal response that adds that step (2) is described refers to be heated to 20～70 ℃ of reaction 1～4h.
In order to realize better the object of the invention, preferably, before the described solid film of step (1) is used, be soaked in 60～240min in solvent and fully soak.Before use, utilize solvent that solid film is fully soaked, be conducive to reaction and obtain gathering uniformly dopamine layer.
Preferably, described solvent refers at least one in ethanol, isopropyl alcohol and isobutanol.
Preferably, the described washing of step (2) refers to repeatedly rinse with clear water.
Concrete reaction equation is as shown in the formula (one)～(two):
The chiral separation solid film of the dopamine pretreatment grafting chiral Recognition body that said method prepares.
The application of the chiral separation solid film of above-mentioned dopamine pretreatment grafting chiral Recognition body in separation of racemic body.
Mechanism of the present invention is:
The present invention uses the solid film of dopamine pretreatment, and dopamine tightly sticks to surface and the fenestra position of solid film under oxygen effect from polycondensation, on the surface of film, introduces active function groups " NH
2,-OH ,-C=O ", then with containing amino chiral Recognition body as β-CD-NH
2or " C=O " on BSA and film surface carry out schiff base reaction, introduce chiral Recognition site, thereby make chiral separation solid film.
The present invention, with respect to prior art, has following advantage and beneficial effect:
(1) the present invention, by simple soaking technology, can introduce on the surface of solid film the active function groups " NH of firm stable
2,-OH ,-C=O ", not only improved the hydrophily on solid film surface, be convenient to the further chemical modification of film simultaneously.
(2) by simple soaking technology, do not affect structure and the performance of film, can carry out on the surface of solid film chemical modification and introduce chiral Recognition site.
(3) preparation method's reaction of the present invention can omnidistance be carried out in the aqueous solution, and reaction condition is gentle, not harsh, expanded the selective of solid film modification, and technique is simple, is easy to realize industrialization volume production.
The specific embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1
(1) β-CD-NH
2preparation: 12.0g β-CD is joined in the distilled water of 100mL, 1.32g NaOH is dissolved in 4mL water, be added drop-wise in β-CD solution, the homogeneous that becomes gradually of suspension originally.Again 2.24g paratoluensulfonyl chloride is dissolved in the acetonitrile of 8mL, is added drop-wise in the solution of β-CD, occur white precipitate, at 25 ℃, react after 2h, be positioned at 4 ℃ and spend the night.Filtration obtains white solid, after soaking, filters with hot wash twice with ether, dry under vacuum, obtains intermediate 6-OTs-β-CD.Get again the reacting ethylenediamine of 1.0g 6-OTs-β-CD and 6g, back flow reaction 4h at 70 ℃, the solution obtaining is deposited in acetonitrile solution after slightly diluting with a certain amount of methyl alcohol, obtains white solid, and dried overnight under vacuum, obtains β-CD-NH
2.Get the dopamine Tris-buffer solution that (pH8.0) in the Tris-buffer solution that 1g dopamine (Aladdin reagent Co., Ltd) is dissolved in 1L prepares 1g/L.Get 1g β-CD-NH
2be dissolved in β-CD-NH that (pH8.0) in the Tris-buffer solution of 1L prepares 1g/L
2tris-buffer solution.
(2) ps hollow fiber uf membrane (Jia, Shenzhen City spring membrane filtration Co., Ltd) is first soaked in to 60min in absolute ethyl alcohol, allows film thoroughly soak.
(3) ps hollow fiber uf membrane of soaking into is taken out in the dopamine Tris-buffer solution that is soaked in 1g/L (pH8.0), under room temperature, be exposed in air, stir 12h, after completion of the reaction film is taken out with clear water and cleaned.
(4) by the solid film after dopamine processing, be soaked in 1g/L β-CD-NH
2tris buffer solution in (pH8.0), at 50 ℃, react 1h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, ps hollow fiber uf membrane flow is 95Lm
-2h
-1, after modification, polysulfone hollow fibre chiral resolution film flow is 215Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 26%, and to D, the fractionation efficiency (e.e%) of L-Trp is 31%.
Embodiment 2
(1) polyvinylidene fluoride flat film (Guangzhou Chao Yu membrane separation technique Co., Ltd) is first soaked in to 90min in isopropyl alcohol (98%), allows film thoroughly soak.
(2) the polyvinylidene fluoride flat film soaking into is taken out in the dopamine Tris buffer solution that is soaked in 2g/L (pH8.5), under room temperature, be exposed in air, stir 24h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 2g/L BSA-NH
2tris buffer solution in (pH8.5), at 20 ℃, react 2h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, polyvinylidene fluoride flat film flow is 90Lm
-2h
-1, after modification, polyvinylidene fluoride flat chiral resolution film flow is 245Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 29%, and to D, the fractionation efficiency (e.e%) of L-Trp is 35%.
Embodiment 3
(1) polytetrafluorethyletubular tubular film (Guangzhou auspicious ultra-clean water Science and Technology Ltd.) is first soaked in to 240min in isobutanol (98%), allows film thoroughly soak.Get the dopamine Tris-buffer solution that (pH9.0) in the Tris-buffer solution that 5g dopamine (Aladdin reagent Co., Ltd) is dissolved in 1L prepares 5g/L.Get 1g β-CD-NH
2be dissolved in β-CD-NH that (pH9.0) in the Tris-buffer solution of 5L prepares 5g/L
2tris-buffer solution.
(2) polytetrafluorethyletubular tubular film soaking into is taken out in the dopamine Tris buffer solution that is soaked in 5g/L (pH9.0), under room temperature, be exposed in air, stir 48h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 5g/L β-CD-NH
2tris buffer solution in (pH9.0), at 70 ℃, react 4h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, polytetrafluorethyletubular tubular film flow is 120Lm
-2h
-1, after modification, polytetrafluorethyletubular tubular chiral resolution film flow is 155Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 34%, and to D, the fractionation efficiency (e.e%) of L-Trp is 42%.
Embodiment 4
(1) polypropylene Flat Membrane (Jia, Shenzhen City spring membrane filtration Co., Ltd) is first soaked in to 120min in absolute ethyl alcohol, allows film thoroughly soak.
(2) the polypropylene Flat Membrane of soaking into is taken out in the dopamine Tris buffer solution that is soaked in 3g/L (pH8.5), under room temperature, in being exposed to air, stir 30h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 3g/L BSA-NH
2tris buffer solution in (pH9.0), at 25 ℃, react 3h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, polypropylene Flat Membrane flow is 90Lm
-2h
-1, after modification, the dull and stereotyped chiral resolution film of polypropylene flow is 325Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 33%, and to D, the fractionation efficiency (e.e%) of L-Trp is 45%.
Embodiment 5
(1) cellulose hollow fibrous membranes (Guangzhou Chao Yu membrane separation technique Co., Ltd) is first soaked in to 180min in isopropyl alcohol (98%), allows film thoroughly soak.
(2) cellulose hollow fibrous membranes soaking into is taken out in the dopamine Tris buffer solution that is soaked in 4g/L (pH8.0), under room temperature, in being exposed to air, stir 40h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 2g/L β-CD-NH
2tris buffer solution in (pH8.5), at 60 ℃, react 3h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, cellulose hollow fibrous membranes flow is 165Lm
-2h
-1, after modification, cellulose hollow fiber chiral resolution film flow is 280Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 37%, and to D, the fractionation efficiency (e.e%) of L-Trp is 47%.
Embodiment 6
(1) polyacrylonitrile tubular film (Guangzhou auspicious ultra-clean water Science and Technology Ltd.) is first soaked in to 240min in isobutanol (98%), allows film thoroughly soak.
(2) the polyacrylonitrile tubular film soaking into is taken out in the dopamine Tris buffer solution that is soaked in 1g/L (pH9.0), under room temperature, in being exposed to air, stir 48h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 5g/L β-CD-NH
2tris buffer solution in (pH8.0), at 50 ℃, react 1h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, polyacrylonitrile tubular film flow is 85Lm
-2h
-1, after modification, polyacrylonitrile tubulose chiral resolution film flow is 155Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 32%, and to D, the fractionation efficiency (e.e%) of L-Trp is 41%.
Embodiment 7
(1) polyether sulphone hollow fibre film (Guangzhou Chao Yu membrane separation technique Co., Ltd) is first soaked in to 80min in isopropyl alcohol (98%), allows film thoroughly soak.
(2) polyether sulphone hollow fibre film soaking into is taken out in the dopamine Tris buffer solution that is soaked in 2.5g/L (pH8.5), under room temperature, in being exposed to air, stir 25h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 2.5g/L BSA-NH
2tris buffer solution in (pH8.5), at 30 ℃, react 2.5h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Modification polyethers prior sulfone hollow-fibre membrane flow is 105Lm
-2h
-1, after modification, cellulose hollow fiber chiral resolution film flow is 175Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 34%, and to D, the fractionation efficiency (e.e%) of L-Trp is 48%.
Embodiment 8
(1) polyester flat film (Jia, Shenzhen City spring membrane filtration Co., Ltd) is first soaked in to 240min in absolute ethyl alcohol, allows film thoroughly soak.
(2) the polyester flat film soaking into is taken out in the dopamine Tris buffer solution that is soaked in 1.5g/L (pH9.0), under room temperature, in being exposed to air, stir 48h, after completion of the reaction film is taken out with clear water and cleaned.
(3) by the solid film after dopamine processing, be soaked in 3.5g/L β-CD-NH
2tris buffer solution in (pH8.0), at 65 ℃, react 3.5h.After completion of the reaction, film rinses repeatedly with clear water, is drying to obtain chiral separation solid film.
Before modification, polyester flat film flow is 145Lm
-2h
-1, after modification, polyester flat chiral resolution film flow is 275Lm
-2h
-1.To D, the fractionation efficiency (e.e%) of L-Histidine is 36%, and to D, the fractionation efficiency (e.e%) of L-Trp is 49%.
Above-described embodiment is preferably embodiment of the present invention; but embodiments of the present invention are not restricted to the described embodiments; other any do not deviate from change, the modification done under Spirit Essence of the present invention and principle, substitutes, combination, simplify; all should be equivalent substitute mode, within being included in protection scope of the present invention.
Claims (10)
1. a preparation method for the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body, is characterized in that comprising following concrete steps:
(1) will consolidate film and be soaked in dopamine solution, stirring reaction, clear water rinses;
(2) by after flushing admittedly film be soaked in chiral Recognition liquid solution, add thermal response, washing, vacuum drying, obtains the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body.
2. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: the described dopamine solution of step (1) refers to that dopamine concentration is the Tris buffer solution of pH8～9 of 1～5g/L.
3. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: the described chiral Recognition liquid solution of step (2) refers to that chiral Recognition bulk concentration is the Tris buffer solution of pH8～9 of 1～5g/L.
4. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: described chiral Recognition body refers to containing amino chiral Recognition body.
5. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: described chiral Recognition body refers at least one in beta-amino-cyclodextrin and bovine serum albumin.
6. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: the described stirring reaction of step (1) refers under room temperature exposure air, stirring reaction 12～48h; That described solid film refers to is flat, at least one in doughnut formula and the solid film of tubulose.
7. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: the thermal response that adds that step (2) is described refers to be heated to 20～70 ℃ of reaction 1～4h; Described washing refers to repeatedly rinse with clear water.
8. the preparation method of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 1, is characterized in that: the described solid film of step (1) refers at least one in PS membrane, polyvinylidene fluoride film, poly tetrafluoroethylene, polypropylene screen, cellulose membrane, polyacrylonitrile film, poly (ether sulfone) film and polyester film.
9. a chiral separation solid film for dopamine pretreatment grafting chiral Recognition body, is characterized in that: according to the preparation method of the chiral separation solid film of the dopamine pretreatment grafting chiral Recognition body described in claim 1～8 any one, prepare.
10. the application of the chiral separation solid film of dopamine pretreatment grafting chiral Recognition body according to claim 9 in separation of racemic body.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104001431A (en) * | 2014-03-20 | 2014-08-27 | 中国药科大学 | Preparing method of beta-cyclodextrin immobilized cellulose membrane used for tryptophan chiral separation |
| CN108654396A (en) * | 2018-05-25 | 2018-10-16 | 南京佳乐净膜科技有限公司 | Polymer film and preparation method with absorption heavy metal and organic pollution function |
| CN108671773A (en) * | 2018-06-07 | 2018-10-19 | 中国药科大学 | A kind of modification cellulose acetate film, preparation method and application for chiral resolution |
| CN109126477A (en) * | 2018-09-13 | 2019-01-04 | 浙江工业大学 | A kind of preparation method of chiral separation film |
| CN109985609A (en) * | 2019-04-24 | 2019-07-09 | 山东大学 | A kind of PAN film adsorbent material and preparation method thereof of succinyl-beta-cyclodextrin modification |
| CN111849015A (en) * | 2020-06-16 | 2020-10-30 | 江苏大学 | Preparation method and application of beta-cyclodextrin/polydopamine synergistic anti-fouling molecularly imprinted organic composite membrane |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010007696A1 (en) * | 2008-07-18 | 2010-01-21 | Ikuta Kazumasa | Water purifier |
| CN101745327A (en) * | 2009-12-29 | 2010-06-23 | 浙江大学 | Method for fixing biological molecules on polymer microporous membrane surface |
| CN102718713A (en) * | 2012-07-06 | 2012-10-10 | 北京化工大学 | Chiral ionic liquid magnetic nanoparticle product and preparation method and application thereof |
-
2013
- 2013-10-25 CN CN201310513655.4A patent/CN103585903B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010007696A1 (en) * | 2008-07-18 | 2010-01-21 | Ikuta Kazumasa | Water purifier |
| CN101745327A (en) * | 2009-12-29 | 2010-06-23 | 浙江大学 | Method for fixing biological molecules on polymer microporous membrane surface |
| CN102718713A (en) * | 2012-07-06 | 2012-10-10 | 北京化工大学 | Chiral ionic liquid magnetic nanoparticle product and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 戴荣继等: "膜拆分法分离制备手性药物", 《膜科学与技术》 * |
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| CN104001431A (en) * | 2014-03-20 | 2014-08-27 | 中国药科大学 | Preparing method of beta-cyclodextrin immobilized cellulose membrane used for tryptophan chiral separation |
| CN104001431B (en) * | 2014-03-20 | 2016-06-29 | 中国药科大学 | A kind of preparation method of the immobilized cellulose membrane of the beta-schardinger dextrin-for tryptophan chiral separation |
| CN108654396A (en) * | 2018-05-25 | 2018-10-16 | 南京佳乐净膜科技有限公司 | Polymer film and preparation method with absorption heavy metal and organic pollution function |
| CN108671773A (en) * | 2018-06-07 | 2018-10-19 | 中国药科大学 | A kind of modification cellulose acetate film, preparation method and application for chiral resolution |
| CN108671773B (en) * | 2018-06-07 | 2020-07-14 | 中国药科大学 | Modified cellulose acetate membrane for chiral resolution, preparation method and application |
| CN109126477A (en) * | 2018-09-13 | 2019-01-04 | 浙江工业大学 | A kind of preparation method of chiral separation film |
| CN109985609A (en) * | 2019-04-24 | 2019-07-09 | 山东大学 | A kind of PAN film adsorbent material and preparation method thereof of succinyl-beta-cyclodextrin modification |
| CN109985609B (en) * | 2019-04-24 | 2021-08-31 | 山东大学 | Succinyl-beta-cyclodextrin modified PAN membrane adsorption material and preparation method thereof |
| CN111849015A (en) * | 2020-06-16 | 2020-10-30 | 江苏大学 | Preparation method and application of beta-cyclodextrin/polydopamine synergistic anti-fouling molecularly imprinted organic composite membrane |
| CN111849015B (en) * | 2020-06-16 | 2022-04-26 | 江苏大学 | Preparation method and application of beta-cyclodextrin/polydopamine synergistic anti-fouling molecularly imprinted organic composite membrane |
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