CN1390859A - Magnetic compound microsphere of blot gel for biological macromolecular template and its reverse-phase suspension polymerization process for preparing it - Google Patents
Magnetic compound microsphere of blot gel for biological macromolecular template and its reverse-phase suspension polymerization process for preparing it Download PDFInfo
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- CN1390859A CN1390859A CN 02121485 CN02121485A CN1390859A CN 1390859 A CN1390859 A CN 1390859A CN 02121485 CN02121485 CN 02121485 CN 02121485 A CN02121485 A CN 02121485A CN 1390859 A CN1390859 A CN 1390859A
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Abstract
A composite magnetic gel microsphere for biological macromolecualr template blot, based on the template blot (molecular blot) technique, is prepared from different biological macromolaculate as template molecule and different metals (or their oxides) as magentic component through reversed-phase suspension polymerization. It can be used for separating biological macromoleculae with high precision and simple process.
Description
Technical field
The invention belongs to Materials Science and Engineering and bioseparation engineering field, more precisely relate to a kind of magnetic compound microsphere of blot gel for biological macromolecular template and reverse-phase suspension polymerization for preparing its thereof.
Background technology
Molecular recognition and recognition specificity are whole biology ubiquity and distinctive characteristics, and it is special and important to play a part in organic evolution.Template imprinting just is based on biological bionical, adopts the manual method preparation that specific molecular (template molecule or microsphere) is had the technology of the polymkeric substance of recognition specificity.Recently, demonstrate application prospects at aspects such as separating purification, immunoassay, analogue enztme and biosensor, become one of novel material of tool potentiality of new millennium with the molecularly imprinted polymer (MIPs) of this technology preparation.
At present, although the template imprinting technology in a lot of fields, obtained extensive and deep research such as a lot of aspects such as the separation of analogue compounds, antibodies simulation, enzyme simulation, biosimulation transmitter, but the selection of template molecule concentrates on the small molecules mainly.The volatility owing to the big also biologically active of molecular weight of biomacromolecule, therefore, its trace all is very difficult with identification, the breadth and depth of research also can not show a candle to small molecules.
At present, biological macromolecular template trace method mainly contains entrapping method (Hjerten SJ, Liao JL, Nakazato K, Wang Y, Zamaratskaia G, Zhang H-X.Gels mimicking antibodiesin their selective recognition of protein, Chromatography, 1997,44:227-234), microsphere surface blotting (Glad M, Narrlow O, Sellergren B, Siegbahn N, Mosbach K.Use of silane monomers for molecular imprinting and enzymeentrapment in polysiloxane-coated porous silica, J Chromatogr, 1985,347:11-23), planar surface blotting (Shi H, Tsai W-B, Ferrari S, Ratner BD.Template imprinted nanostructural surfaces for protein, Narure, 1999,398:593-597.) and antigenic determinant method (Rachkov A, Minoura N.Towards molecularlyimprinted polymers selective to peptides and protein.The epitopeapproach, Biochimica et Biophysica Acta, 2001,1544:255-266) etc.The entrapping method preparation process is simple, but last handling process is loaded down with trivial details, must just can finish through processes such as the wash-out of template molecule, grinding, screenings; The microsphere surface blotting is a kind of more promising trace method, but because it does not contain magnetic component can't carry out simply and separate easily with magnetic field, only is fit to be used as the stratographic stationary phase and carries out static separation; The planar surface blotting can only obtain sheet material (or film material), can only be used for medically diagnosis and monitoring; The antigenic determinant method does not contain magnetic component equally can't carry out simply and separate easily with magnetic field, and only is applicable to the separation of the diverse biomacromolecule of segment structure of the trace of the biomacromolecule that the segment structure of exposure is perfectly clear and exposure.In addition, more than the imprinted polymer that obtains of several existing methods be all the inflexible polymkeric substance, for non-rigid, bulky template biomacromolecule from imprinted polymer wash-out and the recognition process template biomacromolecule to reenter " in conjunction with the hole " obviously be unfavorable and difficult.
When imbedding the magnetic responsiveness material in polymer microballoon inside, during as iron, cobalt, nickel or its oxide compound, complex microsphere then has and is adding easy under the action of a magnetic field, magnetic stalling characteristic (C Bor Fuh fast, S Y Chen.Magnetic split-flow thin fractionation:new technique for separation ofmagnetically susceptible particles, Journal of Chromatography A, 1998,813:313-324).After in the template imprinting polymkeric substance, imbedding the magnetic responsiveness material, just can be easy to it is separated with back the adding under the action of a magnetic field of identification in its " initiatively " absorption of finishing template molecule.
Adopt inverse suspension polymerization can directly prepare gel micro-ball.But the gel micro-ball of prior art for preparing is owing to can't separate accurately without trace, and owing to do not contain magnetic component and can't carry out simple and dynamic separation easily with magnetic field, can only carry out static separation (D Wistuba, V Schurig.Enantiomerseparation of chiral pharmaceuticals by capillary electrochromatography, Journal of Chromatography A, 2000,875:255-276); If carry out dynamic separation, then need to separate the template imprinting polymer microballoon through process such as centrifugal, operating process is loaded down with trivial details, complicated.
Summary of the invention
The present invention is intended to by the inverse suspension polymerization method template imprinting technology be combined with magnetic susceptibility, prepare nonrigid magnetic compound microsphere of blot gel for biological macromolecular template (being called for short template imprinting gel complex microsphere), and give its certain magnetic responsiveness, make the template imprinting gel complex microsphere that makes finish " initiatively " absorption to the template biomacromolecule and adding under the action of a magnetic field with specificity identification back and be easy to it is separated, reach initiatively identification and convenient isolating purpose at it.
The present invention need solve the compatibility problem of metal (or its oxide compound) powder and polymkeric substance, realize the embedding of polymer gel to inorganics, thereby give the gel complex microsphere certain magnetic responsiveness, and finish trace process simultaneously to the template biomacromolecule, make template imprinting gel complex microsphere have singleness identity, reach the purpose of particular separation the template biomacromolecule.
The present invention need solve the limited swelling problem of template imprinting gel complex microsphere, and is relatively stable with shape and the size of guaranteeing trace hole in the trace of biomacromolecule and recognition process.
The present invention need guarantee that the biological activity of biomacromolecule in the template imprinting process does not change.
The present invention need select to be suitable for the dispersion agent of inverse suspension polymerization, with kind ball and the formation of himself and stable of guaranteeing the surface blot gel complex microsphere.
The present invention is according to the principle of template imprinting technology, with different biomacromolecules as template molecule, different metal (or its oxide compound) is as magnetic component, different macromolecule stabilizers is a dispersion agent, adopts the inverse suspension polymerization method to make the mesh structural porous magnetic compound microsphere of blot gel for biological macromolecular template that the template biomacromolecule is had singleness identity and has " dynamically " characteristic.
Prepared magnetic compound microsphere of blot gel for biological macromolecular template is to be compounded with the magnetic response material in the blot gel for biological macromolecular template microballoon, is mesh structural porous on gel magnetic composite microsphere surface.
Concrete grammar of the present invention may further comprise the steps:
1) preparation of template imprinting gel complex microsphere
The non-polar organic solvent adding is had in the reactor of agitator, ventpipe, add dispersion agent, stir and make it dissolving.With acrylamide (AM), N, N '-methylene-bisacrylamide (Bis) and template biomacromolecule add in the entry, and the dissolving back adds the magnetic powder through grinding, and dispersed with stirring evenly back adds in the reactor, continues to stir; Oxidizing and Reducing Agents is added drop-wise in the reactor after soluble in water.Logical nitrogen deoxygenation, normal-temperature reaction 0.5～4h.After reaction finished, filtering organic solvent part obtained template imprinting gel complex microsphere;
2) wash-out of biomacromolecule
With prepared template imprinting gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.
Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind 2～24h, and wash repeatedly to neutrality, be dried to constant weight in 40～90 ℃ with vacuum drying oven then with distilled water.
Wherein:
Non-polar organic solvent is: benzene, toluene, kerosene, gasoline, hexanaphthene, solvent oil;
Dispersion agent is: methylcellulose gum, ethyl cellulose;
The template biomacromolecule is: protein, polypeptide, nucleic acid, cell;
Magneticsubstance is: Fe, Co, Ni or its oxide compound, alloy;
Oxygenant is: Potassium Persulphate, Sodium Persulfate, ammonium persulphate;
Reductive agent is: S-WAT, sodium bisulfite;
Innovative point of the present invention is:
1. magnetic susceptibility (magnetic responsiveness) is combined with the template imprinting technology and prepare magnetic compound microsphere of blot gel for biological macromolecular template, can realize biomacromolecule is separated purpose accurately and rapidly.
2. acrylamide and N, N '-methylene-bisacrylamide multipolymer and metal (or its oxide compound) powder has good consistency, has the characteristics such as easy, easy to prepare that coat.
3. acrylamide and N, the copolymerization conditions gentleness of N '-methylene-bisacrylamide can keep the biological activity of biomacromolecule and unchangeability.
4. prepared template imprinting gel complex microsphere because of the main master plate biomacromolecule of its identification and " combining the hole " to biomacromolecule size and coincideing mutually in shape, the different biomacromolecule of shape (space structure) so this blot gel complex microsphere separable molecular weight is identical, also separable shape identical (or close) but the different biomacromolecule of molecular weight.
5. prepared template imprinting gel complex microsphere because of its " in conjunction with hole " can change according to the change of environment, promptly has stimulating responsive, makes that template biomacromolecule wash-out is more or less freely.
Template imprinting gel complex microsphere of the present invention combines the accurate specificity evident characteristics of template imprinting polymkeric substance and magnetic composite microsphere foreign field stalling characteristic dual-use function easily, will be in the bioseparation field, biomacromolecule particularly, aspects such as separation as protein, polypeptide, cell have broad application prospects, and loaded down with trivial details in the past sepn process (as high speed centrifugation etc.) is simplified greatly.Existing be used for the template imprinting polymer microballoon in bioseparation engineering field owing to do not contain magnetic component and can't carry out simply and separate easily with magnetic field, and be all rigid polymer, for non-rigid, bulky template biomacromolecule from imprinted polymer wash-out and recognition process the template biomacromolecule to reenter " in conjunction with the hole " all be unfavorable and difficult; And existing magnetic composite microsphere can not be realized accurate separation owing to do not have the bio-identification specificity without the biomolecules trace.
Selected acrylamide of the present invention and N, N '-methylene-bisacrylamide multipolymer and metal (or its oxide compound) powder has good consistency, have and coat characteristics such as easy, easy to prepare, and the preparation condition gentleness, can keep the biological activity of biomacromolecule and unchangeability.
Identical but the different biomacromolecule of shape (space structure) of the prepared separable molecular weight of template imprinting gel complex microsphere of the present invention, also separable shape identical (or close) but the different biomacromolecule of molecular weight, the scope of application is wider.
The template imprinting gel complex microsphere that the present invention is prepared because of its " in conjunction with hole " can change according to the change of environment, promptly has stimulating responsive, makes that template biomacromolecule wash-out is more or less freely.
The prepared template imprinting gel complex microsphere surface in the aqueous solution of the present invention has regular netted hole, has increased microballoon specific surface area and loading capacity, has increased the rate of mass transfer of biomacromolecule in microballoon.
The list of description of drawings Fig. 1: embodiment 1 prepared mesh structural porous magnetic compound microsphere of blot gel for biological macromolecular template
The SEM photo of the ESEM photo of individual particle (hygrometric state, the about 300 μ m of median size) Fig. 2: embodiment 1 prepared template imprinting gel magnetic composite microsphere (dry state, average
The about 240 μ m of particle diameter, Fe
3O
4Content 1.86%)
Embodiment
Embodiment 1.
1, the preparation of bovine serum albumin mold plate blot gel complex microsphere
100ml toluene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g ethyl cellulose, stir and make it dissolving.9gAM, 1g Bis and 0.0330g bovine serum albumin (BSA) are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
3O
4Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains BSA template imprinting gel complex microsphere after finishing.
2, the wash-out of bovine serum albumin
With prepared template imprinting gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind the 24h, and wash repeatedly to neutrality, be dried to constant weight in 80 ℃ with vacuum drying oven then with distilled water.
Prepared magnetic compound microsphere of blot gel for biological macromolecular template is to be compounded with Fe in bovine serum albumin mold plate blot gel complex microsphere
3O
4Magneticsubstance, Fe
3O
4Content is 1.86%, and the aperture is about 4 μ m, serves as the contrast molecule with N,O-Diacetylmuramidase and Protalbinic acid respectively, and its separation factor to bovine serum albumin is respectively 4.17 and 3.95.
Embodiment 2.
1, the preparation of N,O-Diacetylmuramidase template imprinting gel complex microsphere
100ml toluene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g ethyl cellulose, stir and make it dissolving.9gAM, 1g Bis and 0.0144g N,O-Diacetylmuramidase are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
3O
4Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains N,O-Diacetylmuramidase template imprinting gel complex microsphere after finishing.
2, the wash-out of N,O-Diacetylmuramidase
With prepared gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind the 24h, and wash repeatedly to neutrality, be dried to constant weight in 80 ℃ with vacuum drying oven then with distilled water.
Prepared magnetic compound microsphere of blot gel for biological macromolecular template is to be compounded with Fe in N,O-Diacetylmuramidase template imprinting gel complex microsphere
3O
4Magneticsubstance, Fe
3O
4Content is 1.96%, and the aperture is about 3 μ m, serves as the contrast molecule with bovine serum albumin and Protalbinic acid respectively, and the separation factor of N,O-Diacetylmuramidase is respectively 5.14 and 4.67.
Embodiment 3.
1, the preparation of Protalbinic acid template imprinting gel complex microsphere
100ml benzene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g methylcellulose gum, stir and make it dissolving.9gAM, 1g Bis and 0.0215g Protalbinic acid are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
2O
3Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains Protalbinic acid template imprinting gel complex microsphere after finishing.
2, the wash-out of Protalbinic acid
With prepared gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind the 24h, and wash repeatedly to neutrality, be dried to constant weight in 80 ℃ with vacuum drying oven then with distilled water.
Prepared magnetic compound microsphere of blot gel for biological macromolecular template is to be compounded with Fe in Protalbinic acid template imprinting gel complex microsphere
2O
3Magneticsubstance, Fe
2O
3Content is 2.85%, and u directly is about 3 μ m, serves as the contrast molecule with bovine serum albumin and N,O-Diacetylmuramidase respectively, and the separation factor of Protalbinic acid is respectively 3.86 and 3.58.
Claims (9)
1. a magnetic compound microsphere of blot gel for biological macromolecular template is characterized in that being compounded with the magnetic response material in the blot gel for biological macromolecular template microballoon, is mesh structural porous on gel magnetic composite microsphere surface.
2. a kind of magnetic compound microsphere of blot gel for biological macromolecular template as claimed in claim 1 is characterized in that being compounded with Fe in bovine serum albumin mold plate blot gel complex microsphere
3O
4Magneticsubstance, Fe
3O
4Content is 1.86%, and the aperture is about 4 μ m, serves as the contrast molecule with N,O-Diacetylmuramidase and Protalbinic acid respectively, and its separation factor to bovine serum albumin is respectively 4.17 and 3.95.
3. a kind of magnetic compound microsphere of blot gel for biological macromolecular template as claimed in claim 1 is characterized in that being compounded with Fe in N,O-Diacetylmuramidase template imprinting gel complex microsphere
3O
4Magneticsubstance, Fe
3O
4Content is 1.96%, and the aperture is about 3 μ m, serves as the contrast molecule with bovine serum albumin and Protalbinic acid respectively, and the separation factor of N,O-Diacetylmuramidase is respectively 5.14 and 4.67.
4. a kind of magnetic compound microsphere of blot gel for biological macromolecular template as claimed in claim 1 is characterized in that being compounded with Fe in Protalbinic acid template imprinting gel complex microsphere
2O
3Magneticsubstance, Fe
2O
3Content is 2.85%, and the aperture is about 3 μ m, serves as the contrast molecule with bovine serum albumin and N,O-Diacetylmuramidase respectively, and the separation factor of Protalbinic acid is respectively 3.86 and 3.58.
5. the reverse-phase suspension polymerization for preparing its of a magnetic compound microsphere of blot gel for biological macromolecular template may further comprise the steps:
1) preparation of template imprinting gel complex microsphere
The non-polar organic solvent adding is had in the reactor of agitator, ventpipe, add dispersion agent, stir and make it dissolving.With acrylamide (AM), N, N '-methylene-bisacrylamide (Bis) and template biomacromolecule add in the entry, and the dissolving back adds the magnetic powder through grinding, and dispersed with stirring evenly back adds in the reactor, continues to stir; Oxidizing and Reducing Agents is added drop-wise in the reactor after soluble in water.Logical nitrogen deoxygenation, normal-temperature reaction 0.5～4h.After reaction finished, filtering organic solvent part obtained template imprinting gel complex microsphere;
2) wash-out of biomacromolecule
With prepared template imprinting gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.
Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind 2～24h, and wash repeatedly to neutrality, be dried to constant weight in 40～90 ℃ with vacuum drying oven then with distilled water.
6. the reverse-phase suspension polymerization for preparing its of a kind of magnetic compound microsphere of blot gel for biological macromolecular template as claimed in claim 5, it is characterized by described: non-polar organic solvent is: benzene, toluene, kerosene, gasoline, hexanaphthene, solvent oil; Dispersion agent is: methylcellulose gum, ethyl cellulose; The template biomacromolecule is: protein, polypeptide, nucleic acid, cell; Magneticsubstance is: Fe, Co, Ni or its oxide compound, alloy; Oxygenant is: Potassium Persulphate, Sodium Persulfate, ammonium persulphate; Reductive agent is: S-WAT, sodium bisulfite;
7. the reverse-phase suspension polymerization for preparing its of a kind of magnetic compound microsphere of blot gel for biological macromolecular template as claimed in claim 5 may further comprise the steps:
1) preparation of template imprinting gel complex microsphere
100ml toluene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g ethyl cellulose, stir and make it dissolving.9gAM, 1g Bis and 0.0330g bovine serum albumin (BSA) are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
3O
4Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains BSA template imprinting gel complex microsphere after finishing.
2) wash-out of biomacromolecule
With prepared template imprinting gel complex microsphere with acetone rinsing after, wash repeatedly with distilled water.Use the aqueous solution soaking of acetate and sodium lauryl sulphate then, soak elimination solution behind the 24h, and wash repeatedly to neutrality, be dried to constant weight in 80 ℃ with vacuum drying oven then with distilled water.
8. the suspension polymerization preparation method of a kind of magnetic composite microsphere of molecular blot polymer as claimed in claim 7 is characterized in that described step 1) is:
100ml toluene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g ethyl cellulose, stir and make it dissolving.9gAM, 1g Bis and 0.0144g N,O-Diacetylmuramidase are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
3O
4Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains N,O-Diacetylmuramidase template imprinting gel complex microsphere after finishing.
9. the suspension polymerization preparation method of a kind of magnetic composite microsphere of molecular blot polymer as claimed in claim 7 is characterized in that described step 1) is:
100ml benzene is added in the there-necked flask of the 250ml that has agitator, ventpipe, add the 0.2g methylcellulose gum, stir and make it dissolving.9gAM, 1g Bis and 0.0215g Protalbinic acid are added in the 20ml water, and the dissolving back adds the magnetic Fe of 0.2g through grinding
2O
3Powder, dispersed with stirring evenly back add in the there-necked flask, continue to stir; Be added drop-wise in the there-necked flask after being dissolved in 0.1g Potassium Persulphate and 0.05g sodium bisulfite in the 10ml water.Logical nitrogen deoxygenation, normal-temperature reaction 2h.Reaction with 180 eye mesh screen filtering organic solvent parts, obtains Protalbinic acid template imprinting gel complex microsphere after finishing.
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| CN100348633C (en) * | 2005-11-25 | 2007-11-14 | 天津理工大学 | DNA print thermo-sensitive high molecule material and preparation process thereof |
| CN100400557C (en) * | 2005-11-25 | 2008-07-09 | 天津理工大学 | Protein print large pore macromolecular compound and preparation process thereof |
| CN101905151A (en) * | 2010-08-12 | 2010-12-08 | 南昌航空大学 | Preparation method and applications of magnetic metal ion surface imprinted polymer |
| CN101101282B (en) * | 2007-06-11 | 2011-06-08 | 中山大学 | Microwave assisted molecular blotting magnetic microsphere preparation method and uses |
| CN102527349A (en) * | 2011-11-28 | 2012-07-04 | 江苏大学 | Magnetic composite material surface imprinting thermosensitive adsorbent, and preparation method and application thereof |
| CN102532408A (en) * | 2011-12-27 | 2012-07-04 | 南开大学 | Preparation method of temperature sensitive magnetic western-blotting nanosphere |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348633C (en) * | 2005-11-25 | 2007-11-14 | 天津理工大学 | DNA print thermo-sensitive high molecule material and preparation process thereof |
| CN100400557C (en) * | 2005-11-25 | 2008-07-09 | 天津理工大学 | Protein print large pore macromolecular compound and preparation process thereof |
| CN101101282B (en) * | 2007-06-11 | 2011-06-08 | 中山大学 | Microwave assisted molecular blotting magnetic microsphere preparation method and uses |
| CN101905151A (en) * | 2010-08-12 | 2010-12-08 | 南昌航空大学 | Preparation method and applications of magnetic metal ion surface imprinted polymer |
| CN102527349A (en) * | 2011-11-28 | 2012-07-04 | 江苏大学 | Magnetic composite material surface imprinting thermosensitive adsorbent, and preparation method and application thereof |
| CN102527349B (en) * | 2011-11-28 | 2013-11-20 | 江苏大学 | Magnetic composite material surface imprinting thermosensitive adsorbent, and preparation method and application thereof |
| CN102532408A (en) * | 2011-12-27 | 2012-07-04 | 南开大学 | Preparation method of temperature sensitive magnetic western-blotting nanosphere |
| CN102532408B (en) * | 2011-12-27 | 2014-01-15 | 南开大学 | Preparation method of temperature sensitive magnetic western-blotting nanosphere |
| CN107417935A (en) * | 2017-06-09 | 2017-12-01 | 金陵科技学院 | A kind of surface modification silicon substrate hydrogel molecules trace kaempferia galamga phenol polymer and preparation method thereof |
| CN110124533A (en) * | 2019-06-17 | 2019-08-16 | 天津工业大学 | A kind of anti-polluting oil-water separation ultra-filtration membrane and preparation method thereof that gel micro-ball is modified |
| CN110124533B (en) * | 2019-06-17 | 2021-05-28 | 天津工业大学 | Gel microsphere modified anti-pollution oil-water separation ultrafiltration membrane and preparation method thereof |
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| CN1176110C (en) | 2004-11-17 |
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