CN104316628B - Molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post - Google Patents
Molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post Download PDFInfo
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Abstract
The present invention relates to a kind of molecule crowding agent and ionic liquid is the method that pore-foaming agent prepares trace integral post, the method is by special pore-foaming agent formula Design, template molecule ursolic acid or oleanolic acid add in the pore-foaming agent be made up of macromolecular crowding reagent, ionic liquid and dimethyl sulfoxide (DMSO), add function monomer, crosslinking chemical and initiating agent again, ultrasonic degas, logical nitrogen deoxygenation, obtains ursolic acid or oleanolic acid molecular engram integral column; The method of the invention makes macromolecular agent and green solvent ionic liquid physical efficiency form the molecular engram integral column with good perviousness and obvious imprinting effect.Obtaining ursolic acid or oleanolic acid molecular engram integral column ratio, to be used alone imprinting effect when macromolecular agent and ionic liquid are pore-foaming agent better.The present invention have preparation simple, avoid the features such as loaded down with trivial details preparation process, molecular recognition performance are good, obtained molecular engram integral column has good perviousness and obvious imprinting effect, provides a kind of new method for obtaining imprinting effect better trace integral post.
Description
Technical field
Invention belongs to Pharmaceutical Analysis field, relates to the preparation of molecular engram integral column, particularly a kind of with macromolecular crowding reagent and ionic liquid for pore-foaming agent prepares the method for molecular engram integral column.
Background technology
Molecular imprinting is the technology that the synthesis developed on the basis of enzyme-substrate and receptor-antibody effect in simulating nature circle has preselected property Stationary liquid.Imprinted polymer prepared by this technology has compatibility and selectivity is good, and the advantages such as anti-adverse environment ability is strong, good stability, long service life and applied range, have been widely used in chemical catalysis, Solid-Phase Extraction, chromatographic resolution, slowly released and controlled-drug delivery system, the fields such as chemical sensor.
In-situ polymerization a kind ofly prepolymerization mixed solution is injected into empty chromatographic column, capillary column or solid surface, by can directly apply after wash-out removing template molecule, preparation synthesis integral post has good penetrability, mass transfer velocity is fast, separation efficiency is high and be easy to the advantage of modification.In addition it also has the feature of perfusion chromatography, not only in chromatographic column existing mobile phase opening (close to 1 μm) but also have and be convenient to the mesopore (tens nanometers) that solute carries out mass transfer, and the stability of chromatographic column is fine, therefore integral post is also described as continue polysaccharide, is cross-linked and is coated with the forth generation chromatograph packing material after stain, single dispersing.Molecular engram integral column is the integration technology of high performance liquid chromatography and molecular engram integral column, it had both had the advantage of high performance liquid chromatography Gao Zhuxiao, also there is the advantage of the high selectivity of MIP, therefore there is the efficiency that the MIP for preparing than conventional bulk polymerization method is higher.In the process of molecular engram integral column development, the optimization of polymeric reaction condition plays conclusive effect, once polymeric reaction condition optimization is selected, the chromatographic column success ratio of preparation can reach 100%, and the pore-foaming agent therefore succeeded in developing is most important to the molecular engram integral column that processability is good.
Ionic liquid refers in room temperature or close to presenting salt that is liquid, that be made up of zwitterion completely under room temperature, also referred to as low temperature molten salt, because its vapour pressure is extremely low, good solubility property is all had to organic and mineral compound, and can operating temperature wide (-40-300 DEG C), there is good thermal stability and chemical stability, make it be widely used in the every field of chemical research.In recent years, experiment proves when preparing imprinted polymer, serves as solvent or pore-foaming agent with ionic liquid, and can play the effect accelerated polymerization speed and strengthen imprinting effect, be prepare a kind of new developing direction of imprinted polymer.
Macromolecular crowding is the very important feature of biological cell Middle molecule environment one, namely all there is the various biomacromolecules such as a large amount of protein, nucleic acid, polysaccharide in all cells, therefore the large molecule of any one is all in one and is full of in other macromolecular crowded environment, therefore will strengthen the concentrated tendency of solute, thus reduce the free energy of solution.Similarly, add in organic trace system a large amount of not with the inert polymer of template action, also can cause molecule crowded environment.Existing evidence proves that the existence of macromolecular crowding reagent can stablize the interaction between template molecule and function monomer when preparing MIPs, and impels balance to move to the direction forming trace compound.The binding ability of imprinted polymer to microsphere of preparation improves greatly, and recognition performance have also been obtained enhancing, and the retention of template on MIP even can exceed the MIP order of magnitude prepared with commonsense method.
Current, ionic liquid and macromolecular crowding reagent all for the preparation of trace integral post, and show good imprinting effect, but both are combined prepare trace integral post with utilize both advantage could not realize.Main cause is common ionic liquid and macromolecular crowding reagent is immiscible, therefore both are difficult to form the system of a homogeneous phase to complete polymerization process, therefore need to develop the mutual solubility that new pore-foaming agent system solves ionic liquid and macromolecular crowding reagent, and obtain good imprinting effect.
Summary of the invention
A kind of molecule crowding agent of the present invention and ionic liquid are the method that pore-foaming agent prepares trace integral post, the method is by special pore-foaming agent formula Design, template molecule ursolic acid or oleanolic acid add in the pore-foaming agent be made up of macromolecular crowding reagent, ionic liquid and dimethyl sulfoxide (DMSO), add function monomer, crosslinking chemical and initiating agent again, ultrasonic degas, logical nitrogen deoxygenation, obtains ursolic acid or oleanolic acid molecular engram integral column; The method of the invention makes macromolecular agent and green solvent ionic liquid physical efficiency form the molecular engram integral column with good perviousness and obvious imprinting effect.Obtaining ursolic acid or oleanolic acid molecular engram integral column ratio, to be used alone imprinting effect when macromolecular agent and ionic liquid are pore-foaming agent better.The present invention have preparation simple, avoid the features such as loaded down with trivial details preparation process, molecular recognition performance are good, obtained molecular engram integral column has good perviousness and obvious imprinting effect, provides a kind of new method for obtaining imprinting effect better trace integral post.
A kind of molecule crowding agent of the present invention and ionic liquid are the method that pore-foaming agent prepares trace integral post, follow these steps to carry out:
A, template molecule ursolic acid or oleanolic acid added by macromolecular crowding reagent be the chloroformic solution of polymethylmethacrylate, ionic liquid be 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
Function monomer 4-vinylpridine, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile is added in the compound formed in b, step a, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, after mixed liquor being injected stainless steel gc column tube good seal again, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column;
C, the molecular engram integral column fech connection that obtained by step b are on high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses and template molecule is removed completely, obtains ursolic acid or oleanolic acid molecular engram integral column.
The mol ratio of the template molecule in step a and the function monomer in step b and crosslinking chemical is 1: 8: 32.
The concentration of the chloroformic solution of the polymethylmethacrylate used in step a is 150mg/mL.
In step a, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column.
In step b, initiating agent azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column.
A kind of molecule crowding agent of the present invention and ionic liquid are the method that pore-foaming agent prepares trace integral post, by a kind of special pore-foaming agent formula Design, macromolecular crowding reagent and ionic liquid is made to have good ability of dissolving each other between the two, and the obtained molecular engram integral column with excellent permeability and molecular recognition effect, the molecular engram integral column even structure using this system to synthesize, permeability are good, and with ursolic acid and oleanolic acid for the molecular engram integral column that template is synthesized under this system has good recognition performance, imprinting effect is obvious.
Accompanying drawing explanation
To be the present invention retain figure with the chromatogram of polymethylmethacrylate and the ionic liquid ursolic acid trace post (MIP-1) that is pore-foaming agent and blank post (NIP-1) to Fig. 1;
Fig. 2 is that the chromatogram of the ursolic acid trace post (MIP-2) and blank post (NIP-2) that the present invention does not add polymethylmethacrylate retains figure;
Fig. 3 is that the present invention retains figure with the chromatogram of the ursolic acid trace post (MIP-3) of isooctane substitutional ion liquid and blank post (NIP-3);
To be the present invention retain figure with the chromatogram of polymethylmethacrylate and the ionic liquid oleanolic acid trace post (MIP-4) that is pore-foaming agent and blank post (NIP-4) to Fig. 4;
Fig. 5 is that the chromatogram of the oleanolic acid trace post (MIP-5) and blank post (NIP-5) that the present invention does not add polymethylmethacrylate retains figure;
Fig. 6 is that the present invention retains figure with the chromatogram of the oleanolic acid trace post (MIP-6) of isooctane substitutional ion liquid and blank post (NIP-6).
Embodiment
Below in conjunction with specific embodiment, elaborate the present invention further.
Embodiment 1
The preparation of the ursolic acid molecular engram integral column being pore-foaming agent with polymethylmethacrylate and ionic liquid and imprinting effect evaluation:
A, template molecule ursolic acid added by macromolecular crowding reagent be the chloroformic solution of polymethylmethacrylate, ionic liquid be 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses 150mL makes template molecule remove completely, obtains ursolic acid molecular engram integral column;
Carry out stratographic analysis by high performance liquid chromatography to it, determined wavelength is set to 214nm, connects the chromatographic column of synthesis with on high performance liquid chromatograph, makes system stability to baseline values, sample introduction, measures the retention time t of ursolic acid
rwith the retention time t of acetone
0, the retention factors formula k '=(t of ursolic acid
r-t
0)/t
0calculate, measured the retention factors of ursolic acid on the blank post not adding template by same method, the imprinting factor formula IF=k ' of ursolic acid
mIP/ k '
nIPcalculate;
Result shows, be acetonitrile/acetate buffer (70/30 in mobile phase condition, v/v) (wherein salinity is 50mmol/L, pH4.2), during flow velocity 0.5mL/min, column temperature is 30 DEG C, and have best imprinting effect with the ursolic acid molecular engram integral column that polymethylmethacrylate and ionic liquid are pore-foaming agent, template molecule ursolic acid IF is 2.33.
Embodiment 2 (contrast)
For investigating polymethylmethacrylate to the impact of this synthetic method, synthesized the ursolic acid molecular engram integral column not adding polymethylmethacrylate, its concrete steps are as follows:
A, template molecule ursolic acid added ionic liquid is 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in the pore-foaming agents of 8: 5 compositions by volume, ultrasonic until template is dissolved completely, forms compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses 150mL makes template molecule remove completely, obtains ursolic acid molecular engram integral column;
Chromatographic evaluation with in embodiment 1 to the investigation of trace post;
Result shows, the ursolic acid molecular engram integral column imprinting effect not adding polymethylmethacrylate obviously declines, and template molecule ursolic acid IF is only 1.13.
Embodiment 3 (contrast)
For investigating ionic liquid to the impact of this synthetic method, synthesized with the ursolic acid molecular engram integral column of isooctane substitutional ion liquid, its concrete steps are as follows:
A, template molecule ursolic acid added by macromolecular crowding reagent be the chloroformic solution of polymethylmethacrylate, ionic liquid be isooctane and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses 150mL makes template molecule remove completely, obtains ursolic acid molecular engram integral column;
Chromatographic evaluation with in embodiment 1 to the investigation of trace post.
Result shows, obviously decline with the ursolic acid molecular engram integral column imprinting effect of isooctane substitutional ion liquid, template molecule ursolic acid IF is only 1.01.
Embodiment 4
The preparation of the oleanolic acid molecular engram integral column being pore-foaming agent with polymethylmethacrylate and ionic liquid and imprinting effect evaluation:
A, template molecule oleanolic acid added by macromolecular crowding reagent be the chloroformic solution of polymethylmethacrylate, ionic liquid be 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution 150mL rinses and template molecule is removed completely, obtains oleanolic acid molecular engram integral column.
Carry out stratographic analysis by high performance liquid chromatography to it, determined wavelength is set to 214nm, is connected on high performance liquid chromatograph by the chromatographic column of synthesis, makes system stability to baseline values, sample introduction, measures the retention time t of oleanolic acid
rwith the retention time t of acetone
0, the retention factors formula k '=(t of oleanolic acid
r-t
0)/t
0calculate, measured the retention factors of oleanolic acid on the blank post not adding template by same method, the imprinting factor formula IF=k ' of oleanolic acid
mIP/ k '
nIPcalculate;
Result shows, be acetonitrile/acetate buffer (70/30 in mobile phase condition, v/v) (wherein salinity is 50mmol/L, pH4.2), during flow velocity 0.5mL/min, column temperature is 30 DEG C, and have best imprinting effect with the oleanolic acid molecular engram integral column that polymethylmethacrylate and ionic liquid are pore-foaming agent, template molecule oleanolic acid IF is 2.97.
Embodiment 5 (contrast)
For investigating polymethylmethacrylate to the impact of this synthetic method, synthesized the oleanolic acid molecular engram integral column not adding polymethylmethacrylate, its concrete steps are as follows:
A, to add by ionic liquid by template molecule oleanolic acid be 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, forms compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses 150mL makes template molecule remove completely, obtains oleanolic acid molecular engram integral column.
Chromatographic evaluation is to the investigation of trace post;
Result shows, the oleanolic acid molecular engram integral column imprinting effect not adding polymethylmethacrylate obviously declines, and template molecule oleanolic acid IF is only 1.12.
Embodiment 6 (contrast)
For investigating ionic liquid to the impact of this synthetic method, synthesized with the oleanolic acid molecular engram integral column of isooctane substitutional ion liquid, its concrete steps are as follows:
A, template molecule oleanolic acid added by macromolecular crowding reagent be the chloroformic solution of polymethylmethacrylate, ionic liquid be isooctane and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
B, function monomer 4-vinylpridine is added in the compound formed in step a, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, mixed liquor being injected stainless steel gc column tube specification is column length 100mm again, after internal diameter 4.6mm good seal, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column, function monomer wherein in template molecule and step b and the mol ratio of crosslinking chemical are 1: 8: 32, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column, azoisobutyronitrile consumption accounts for 0.4% of the gross mass of the raw material gross mass of molecular engram integral column,
C, the molecular engram integral column fech connection that obtained by step b are on HPLC high pressure pump, first rinse with acetonitrile, to remove pore-foaming agent residual in integral post, and then be the methyl alcohol of 90:10 by volume ratio: acetic acid mixed solution rinses 150mL makes template molecule remove completely, obtains oleanolic acid molecular engram integral column.
Chromatographic evaluation is to the investigation of trace post;
Result shows, obviously decline with the oleanolic acid molecular engram integral column imprinting effect of isooctane substitutional ion liquid, template molecule oleanolic acid IF is only 1.02.
Claims (4)
1. molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post, it is characterized in that following these steps to carry out:
A, template molecule ursolic acid or oleanolic acid added by macromolecular crowding reagent concentration be the chloroformic solution of the polymethylmethacrylate of 150mg/mL, ionic liquid be 1-butyl-3-methyl-imidazoles tetrafluoroborate and dimethyl sulfoxide (DMSO) is in 25: 8: 5 pore-foaming agents formed by volume, ultrasonic until template is dissolved completely, form compound;
Function monomer 4-vinylpridine, crosslinking chemical Ethylene glycol dimethacrylate and initiating agent azoisobutyronitrile is added in the compound formed in b, step a, ultrasonic degas 10min, logical nitrogen 10min deoxygenation, after mixed liquor being injected stainless steel gc column tube good seal again, put into temperature 60 C water-bath thermal booster reaction 24h, obtain molecular engram integral column.
2. molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post according to claim 1, it is characterized in that the mol ratio of the template molecule in step a and the function monomer in step b and crosslinking chemical is 1: 8: 32.
3. molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post according to claim 1, it is characterized in that in step a, the total consumption of pore-foaming agent accounts for 80% of the raw material gross mass of molecular engram integral column.
4. molecule crowding agent and ionic liquid are the method that pore-foaming agent prepares trace integral post according to claim 1, it is characterized in that in step b, initiating agent azoisobutyronitrile consumption accounts for 0.4% of the raw material gross mass of molecular engram integral column.
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| CN106512963A (en) * | 2015-11-11 | 2017-03-22 | 大连出入境检验检疫局检验检疫技术中心 | Tetrodotoxin molecularly imprinted monolithic column preparation method, monolithic column and application of monolithic column |
| CN105399915B (en) * | 2015-12-18 | 2017-12-12 | 天津医科大学 | Aesculin delays controlled release molecular engram framework material and preparation method thereof |
| CN105771941A (en) * | 2016-03-04 | 2016-07-20 | 中国科学院新疆理化技术研究所 | Low-template-consumption punicalin imprinting method based on dual-crowding effect |
| CN106345436B (en) * | 2016-10-12 | 2018-03-09 | 中国科学院新疆理化技术研究所 | A kind of preparation method of procyanidin B 2 trace integral post |
| CN111253613B (en) * | 2020-01-18 | 2022-04-22 | 南阳师范学院 | Ursolic acid magnetic molecular imprinting nano-microsphere and extraction method of ursolic acid in dogwood |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101852791A (en) * | 2010-05-21 | 2010-10-06 | 天津出入境检验检疫局动植物与食品检测中心 | Method for preparing norfloxacin molecular imprinted monolithic column in ionic liquid |
| CN102382247A (en) * | 2010-09-03 | 2012-03-21 | 中国科学院过程工程研究所 | Preparation method of molecular imprinting polymer micro-sphere with uniform size and application |
| CN102847526A (en) * | 2012-09-28 | 2013-01-02 | 中国科学院新疆理化技术研究所 | Method for preparing punicalagin molecularly imprinted polymer monolithic column by utilizing in-situ polymerization method |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101852791A (en) * | 2010-05-21 | 2010-10-06 | 天津出入境检验检疫局动植物与食品检测中心 | Method for preparing norfloxacin molecular imprinted monolithic column in ionic liquid |
| CN102382247A (en) * | 2010-09-03 | 2012-03-21 | 中国科学院过程工程研究所 | Preparation method of molecular imprinting polymer micro-sphere with uniform size and application |
| CN102847526A (en) * | 2012-09-28 | 2013-01-02 | 中国科学院新疆理化技术研究所 | Method for preparing punicalagin molecularly imprinted polymer monolithic column by utilizing in-situ polymerization method |
Non-Patent Citations (1)
| Title |
|---|
| 活性/可控自由基聚合的分子印迹整体柱的制备及性能评价;班璐;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20140215(第2期);B016-43 * |
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