CN106146716A - A kind of OPC B2molecularly imprinted polymer and its preparation method and application - Google Patents
A kind of OPC B2molecularly imprinted polymer and its preparation method and application Download PDFInfo
- Publication number
- CN106146716A CN106146716A CN201610377672.3A CN201610377672A CN106146716A CN 106146716 A CN106146716 A CN 106146716A CN 201610377672 A CN201610377672 A CN 201610377672A CN 106146716 A CN106146716 A CN 106146716A
- Authority
- CN
- China
- Prior art keywords
- opc
- molecularly imprinted
- imprinted polymer
- polymer
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention belongs to molecularly imprinted polymer technical field, be specifically related to a kind of OPC B2Metal-complexing molecularly imprinted polymer and its preparation method and application.The present invention is by by OPC B2, metallic compound mix in a solvent with function monomer, add crosslinking agent and initiator, protective gas carry out polymerisation, after then carrying out to polymer eluting, being dried, it is thus achieved that OPC B2Metal-complexing molecularly imprinted polymer.And pass through SPE, it using prepared polymer as filler, is used for OPC B2Isolated and purified fast and efficiently.The preparation method of the present invention is simple, reliable, and the molecularly imprinted polymer of gained has stronger specific selectivity and the higher rate of recovery, has a extensive future in the isolated and purified field of OPC.
Description
Technical field
The invention belongs to molecularly imprinted polymer technical field, be specifically related to a kind of OPC B2Metal-complexing molecule prints
Mark polymer and its preparation method and application.
Background technology
OPC is to be passed through C by catechin, epicatechin and gallate thereof4-C6Or C4-C8Covalency is connected composition
Condensate, it can remove superfluous free radical in human body, improve body immunity, can as anti-cancer, anti-sudden change, prevent and treat cardiovascular
The principle active component of disease medicament and the novel antioxidant being used as safety non-toxic.OPC B2It is by two epicatechins
The dimer (molecular structural formula is shown in Fig. 1) being polymerized, there are some researches show, it is the list that in OPC, antioxidation activity is the strongest
Body, can be as the significant composition weighing OPC quality.Due to OPC B2In condensate, content is relatively low, Er Qieyu
Other polymeric structures and character are close, and this causes great difficulty to its separation.Therefore, at present both at home and abroad with regard to former flower
Blue or green element B2The preparative separation technique of the related maturation such as monomer is also few.
Molecularly imprinted polymer is that function monomer carries out under template molecule existence condition cross-linked polymeric, and then wash-out removes
Removing the polymer that template molecule prepares, it has the sky with target molecule complementary structure on space structure and function base are arranged
Cave, has " memory " function, thus has selectivity that can be predetermined to target molecule to template molecule.Due to molecular engram polymerization
Thing has selective strong, stable chemical nature, to advantages such as the better tolerance of environment, preparation are simple, in being applied at present
The fields such as the separation of medicine active component, SPE, biomimetic sensor, mimetic enzyme catalysis.
Content of the invention
In order to solve the problems referred to above, an object of the present invention is that offer one can be isolated and purified fast and efficiently
OPC B2Metal-complexing molecularly imprinted polymer.
The two of the purpose of the present invention there is provided described OPC B2The preparation side of metal-complexing molecularly imprinted polymer
Method.
The three of the purpose of the present invention there is provided described OPC B2The application of metal-complexing molecularly imprinted polymer.
The present invention is achieved through the following technical solutions:
A kind of OPC B2Metal-complexing molecularly imprinted polymer, including template molecule, metallic compound, tetrahydrochysene furan
Mutter/methyl alcohol, function monomer, crosslinking agent and initiator；Calculating in molar ratio, the mol ratio of template molecule and metallic compound is 1:
1～1:3, template molecule is 1:3～1:8 with the mol ratio of function monomer, and function monomer is 1:4～1 with the mol ratio of crosslinking agent:
6, initiator is 1:50～1:20 with the mol ratio of function monomer；Calculate by mole volume basis, template molecule and oxolane/first
The ratio of alcohol is 1:10～1:15 (mmol/ml).
It is preferred that described metallic compound is copper chloride, zinc acetate or aluminum nitrate.
It is preferred that described function monomer be α-methacrylic acid, to vinyl benzoic acid or 2-vinylpyridine.
It is preferred that described crosslinking agent is divinylbenzene (DVB), pentaerythritol triacrylate (PETA) or ethylene glycol
Dimethylacrylate (EGDMA).
It is preferred that described initiator is azodiisobutyronitrile (AIBN), azo-bis-iso-dimethyl (AIBME) or even
Nitrogen dicyclohexyl formonitrile HCN (ACCN).
Prepare described OPC B2The method of metal-complexing molecularly imprinted polymer, particularly as follows:
(1), by template molecule OPC B2Join the oxolane/methanol solution of described amount with metallic compound
In, ultrasonic vibration 1～1.5h, make metal ion and OPC B2Fully coordination；
(2) in step (1) solution, add the function monomer of described amount, ultrasonic vibration 1～1.5h, make function monomer, gold
Belong to ion and OPC B2Fully reaction；
(3) in step (2) solution, add initiator and the crosslinking agent of described amount, ultrasonic vibration 15～20min, nitrogen charging
10min final vacuum seals, and 50～60 DEG C of water bath with thermostatic control thermal-initiated polymerization 24h obtain polymer；
(4), polymer ground 200 mesh sieves after drying, and repeatedly cleans and removed fine grained in methanol solution.Will
The polymer obtaining uses the solution extracting of acetic acid/methyl alcohol, eluted template molecule OPC B in apparatus,Soxhlet's2, until returning
Till flow liquid be can't detect at 280nm by high performance liquid chromatography；Then EDTA solution washing removes residual in the polymer
Metal ion, finally use water and methyl alcohol repeated washing pH to neutral, put in vacuum drying chamber and be dried, obtain OPC B2
Metal-complexing molecularly imprinted polymer.
It is preferred that the volume ratio of described oxolane/methyl alcohol is 1:4.
It is preferred that the volume ratio of described acetic acid/methyl alcohol is 8:2～9:1.
It is preferred that described EDTA solution concentration is 1～4mmol/L.
Described OPC B2The using method of metal-complexing molecularly imprinted polymer: prepared OPC B2Metal
Ligand molecule imprinted polymer loads solid-phase extraction column, after adding methanol solution to drench solid-phase extraction column, extracts OPC
Liquid loading (is extracted in the raw material such as tea seed episperm, grape pip), and absorption uses acetic acid/methyl alcohol (volume ratio is 8:2～9:1) after finishing
Eluant solution, concentrated, be dried after obtain highly purified OPC B2Product.
Beneficial effects of the present invention:
(1), current, OPC B2Research be mainly limited to assay and trace analysis, preparation technology is mainly led to
Cross multiple separation such as macroporous resin adsorption, gel filtration chromatography, preparative high performance liquid chromatography and analysis means, there is step numerous
The shortcomings such as trivial, with high costs, product impurity is many, the Selective Separation OPC B that the employing present invention can be single2, there is behaviour
Make simple, with low cost, good selective.
(2) OPC B prepared by the inventive method, is used2Polymer has very high strength and stability, Ke Yichong
Multiple use, industrialization prospect is wide.Observe OPC B with ESEM respectively2The configuration of surface of polymer before and after wash-out, sends out
Before and after now eluting, the structure on imprinted polymer surface has dramatically different: OPC B2It is eluted prepolymer surface relatively equal
Even, smooth；OPC B2It is eluted rear imprinted polymer porous surface, uneven, show that polymer has compared with multi-hole
With active binding site (see Fig. 4, Fig. 5).
(3), current, the preparation process of major part molecularly imprinted polymer is to carry out in weak polar solvent.From structure
Analyze, OPC B2Containing multiple hydroxyls, its polarity is relatively big and is not readily dissolved in nonpolar or weak polar solvent.And introduce metal
Ion, utilizes the coordination of metal ion, can prepare the ligand molecule trace polymerization with higher selection recognition capability
Thing, is suitable for isolated and purified OPC B in highly polar solution2, thus expand the range of application of molecular imprinting.
Brief description
Fig. 1 OPC B2Molecular structural formula.
Fig. 2 OPC B2The HPLC collection of illustrative plates of standard items.
Fig. 3 OPC B2The HPLC collection of illustrative plates of product.
Fig. 4 OPC B2The scanning electron microscopic picture of molecularly imprinted polymer before wash-out.
Fig. 5 OPC B2The scanning electron microscopic picture of molecularly imprinted polymer after wash-out.
Specific embodiment
Below in conjunction with detailed description of the invention, the present invention is described in further detail, to help those skilled in the art's reason
Solve the present invention.
Embodiment 1:
A kind of OPC B2The preparation method and applications of metal-complexing molecularly imprinted polymer:
(1), by 1mmol template molecule OPC B2Join the oxolane/methyl alcohol of 10ml with 1mmol copper chloride
In (volume ratio 1:4) solution, ultrasonic vibration 1h, make metal ion and OPC B2Fully coordination.
(2), in step (1) solution add 3mmol α-methacrylic acid, ultrasonic vibration 1h, make α-methacrylic acid,
Copper ion and OPC B2Fully reaction.
(3), add the cross-linker divinylbenzene (DVB) of 12mmol and 0.1mmol azo two different in step (2) solution
Butyronitrile (AIBN) initiator, ultrasonic vibration 15min, nitrogen charging 10min final vacuum seals, 50 DEG C of water bath with thermostatic control thermal-initiated polymerization 24h,
Obtain polymer.
(4), polymer ground 200 mesh sieves after drying, and repeatedly cleans and removed fine grained in methanol solution.Will
The polymer obtaining in apparatus,Soxhlet's with the solution of acetic acid/methyl alcohol (volume ratio is 8:2) extract, the former flower of eluted template molecule
Blue or green element B2, till can't detect at 280nm with high performance liquid chromatography in phegma；Then 1mmol/L EDTA solution is used
Washing removes residual metal ion in the polymer, finally uses water and methyl alcohol repeated washing pH to neutral, puts into vacuum drying
Case is dried, obtains OPC B2Metal-complexing molecularly imprinted polymer.
(5), by prepared OPC B2Metal-complexing molecularly imprinted polymer loads solid-phase extraction column, adds methyl alcohol molten
After liquid drenches solid-phase extraction column, and by OPC extract loading (extracting in the raw material such as tea seed episperm, grape pip), absorption finishes
Rear employing acetic acid/methyl alcohol (volume ratio is 8:2) eluant solution, concentrated, be dried after obtain OPC B2Product, through HPLC
Detection purity is 95.2%.
Embodiment 2:
A kind of OPC B2The preparation method and applications of metal-complexing molecularly imprinted polymer:
(1), by 1mmol template molecule OPC B2Join the oxolane/methyl alcohol of 15ml with 2mmol zinc acetate
In (volume ratio 1:4) solution, ultrasonic vibration 1.5h, make metal ion and OPC B2Fully coordination.
(2), in step (1) solution add 5mmol to vinyl benzoic acid, ultrasonic vibration 1.5h, make to vinyl
Benzoic acid, zinc ion and OPC B2Fully reaction.
(3), in step (2) solution add 25mmol crosslinking agent pentaerythritol triacrylate (PETA) and
0.2mmol azo-bis-iso-dimethyl (AIBME) initiator, ultrasonic vibration 20min final vacuum seals, 55 DEG C of water bath with thermostatic control heat
Cause polymerization 24h, obtain polymer.
(4), polymer ground 200 mesh sieves after drying, and repeatedly cleans and removed fine grained in methanol solution.Will
The polymer obtaining in apparatus,Soxhlet's with the solution of acetic acid/methyl alcohol (volume ratio is 9:1) extract, the former flower of eluted template molecule
Blue or green element B2, till can't detect at 280nm with high performance liquid chromatography in phegma；Then 2mmol/L EDTA solution is used
Washing removes residual metal ion in the polymer, finally uses water and methyl alcohol repeated washing pH to neutral, puts into vacuum drying
Case is dried, obtains OPC B2Metal-complexing molecularly imprinted polymer.
(5), by prepared OPC B2Metal-complexing molecularly imprinted polymer loads solid-phase extraction column, adds methyl alcohol molten
After liquid drenches solid-phase extraction column, and by OPC extract loading (extracting in the raw material such as tea seed episperm, grape pip), absorption finishes
Rear employing acetic acid/methyl alcohol (volume ratio is 9:1) eluant solution, concentrated, be dried after obtain OPC B2Product, through HPLC
Detection purity is 96.1%.
Embodiment 3:
A kind of OPC B2The preparation method and applications of metal-complexing molecularly imprinted polymer:
(1), by 1mmol template molecule OPC B2Join the oxolane/methyl alcohol of 15ml with 3mmol aluminum nitrate
In (volume ratio 1:4) solution, ultrasonic vibration 2h, make metal ion and OPC B2Fully coordination.
(2), in step (1) solution add 8mmol 2-vinylpyridine, ultrasonic vibration 2h, make 2-vinylpyridine,
Aluminium ion and OPC B2Fully reaction.
(3), in step (2) solution add 40mmol crosslinking agent ethylene glycol dimethacrylate (EGDMA) and
0.3mmol azo dicyclohexyl formonitrile HCN (ACCN) initiator, ultrasonic vibration 20min, nitrogen charging 10min final vacuum seals, 60 DEG C of perseverances
Tepidarium thermal-initiated polymerization 24h, obtains polymer.
(4), polymer ground 200 mesh sieves after drying, and repeatedly cleans and removed fine grained in methanol solution.Will
The polymer obtaining in apparatus,Soxhlet's with the solution of acetic acid/methyl alcohol (volume ratio is 9:1) extract, the former flower of eluted template molecule
Blue or green element B2, till can't detect at 280nm with high performance liquid chromatography in phegma；Then 4mmol/L EDTA solution is used
Washing removes residual metal ion in the polymer, finally uses water and methyl alcohol repeated washing pH to neutral, puts into vacuum drying
Case is dried, obtains OPC B2Metal-complexing molecularly imprinted polymer.
(5), by prepared OPC B2Metal-complexing molecularly imprinted polymer loads solid-phase extraction column, adds methyl alcohol molten
After liquid drenches solid-phase extraction column, and by OPC extract loading (extracting in the raw material such as tea seed episperm, grape pip), absorption finishes
Rear employing acetic acid/methyl alcohol (volume ratio is 9:1) eluant solution, concentrated, be dried after obtain OPC B2Product, through HPLC
Detection purity is 95.8%.
Above-described embodiment, simply presently preferred embodiments of the present invention, not be used for limiting the scope of the present invention, therefore all with this
The equivalence that feature described in invention claim and principle are done changes or modifies, and all should include in scope of the invention as claimed
Within.
Claims (10)
1. an OPC B2Molecularly imprinted polymer, it is characterised in that include template molecule, metallic compound, tetrahydrochysene furan
Mutter/methyl alcohol, function monomer, crosslinking agent and initiator；Calculating in molar ratio, the mol ratio of template molecule and metallic compound is 1:
1～1:3, template molecule is 1:3～1:8 with the mol ratio of function monomer, and function monomer is 1:4～1 with the mol ratio of crosslinking agent:
6, initiator is 1:50～1:20 with the mol ratio of function monomer；Calculate by mole volume basis, template molecule and oxolane/first
The ratio of alcohol is 1:10～1:15 (mmol/ml).
2. OPC B as claimed in claim 12Molecularly imprinted polymer, it is characterised in that described metallic compound is chlorine
Change copper, zinc acetate or aluminum nitrate.
3. OPC B as claimed in claim 12Molecularly imprinted polymer, it is characterised in that described function monomer is α-first
Base acrylic acid, to vinyl benzoic acid or 2-vinylpyridine.
4. OPC B as claimed in claim 12Molecularly imprinted polymer, it is characterised in that described crosslinking agent is divinyl
Base benzene, pentaerythritol triacrylate or ethylene glycol dimethacrylate.
5. OPC B as claimed in claim 12Molecularly imprinted polymer, it is characterised in that described initiator is azo two
Isobutyronitrile, azo-bis-iso-dimethyl or azo dicyclohexyl formonitrile HCN.
6. prepare OPC B described in any one in claim 1-52The method of molecularly imprinted polymer, it is characterised in that
Particularly as follows:
(1), by template molecule OPC B2Join in the oxolane/methanol solution of described amount with metallic compound, ultrasonic
Concussion 1～1.5h, makes metal ion and OPC B2Fully coordination；
(2) in step (1) solution, add the function monomer of described amount, ultrasonic vibration 1～1.5h, make function monomer, metal from
Son and OPC B2Fully reaction；
(3) in step (2) solution, add initiator and the crosslinking agent of described amount, ultrasonic vibration 15～20min, nitrogen charging 10min
Final vacuum seals, and 50～60 DEG C of water bath with thermostatic control thermal-initiated polymerization 24h obtain polymer；
(4), polymer ground 200 mesh sieves after drying, and repeatedly cleans and removed fine grained in methanol solution；To obtain
Polymer in apparatus,Soxhlet's with the extracting of the solution of acetic acid/methyl alcohol, eluted template molecule OPC B2, until phegma
Till middle high performance liquid chromatography can't detect at 280nm；Then remove with the washing of EDTA solution and remain in the polymer
Metal ion, finally uses water and methyl alcohol repeated washing pH to neutral, puts in vacuum drying chamber and be dried, obtain described OPC
B2Metal-complexing molecularly imprinted polymer.
7. OPC B as claimed in claim 62The preparation method of molecularly imprinted polymer, it is characterised in that in (1), described
The volume ratio of oxolane/methyl alcohol is 1:4.
8. OPC B as claimed in claim 62The preparation method of molecularly imprinted polymer, it is characterised in that in (4), described
The volume ratio of acetic acid/methyl alcohol is 8:2～9:1.
9. OPC B as claimed in claim 62The preparation method of molecularly imprinted polymer, it is characterised in that in (4), described
EDTA solution concentration is 1～4mmol/L.
10. OPC B described in any one in claim 1-92The using method of molecularly imprinted polymer, it is characterised in that:
Prepared OPC B2Metal-complexing molecularly imprinted polymer loads solid-phase extraction column, adds methanol solution to drench solid phase extraction
After taking post, by OPC extract loading, absorption uses the eluant solution of acetic acid/methyl alcohol after finishing, concentrated, be dried after
To highly purified OPC B2Product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610377672.3A CN106146716B (en) | 2016-05-27 | 2016-05-27 | A kind of OPC B2Molecularly imprinted polymer and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610377672.3A CN106146716B (en) | 2016-05-27 | 2016-05-27 | A kind of OPC B2Molecularly imprinted polymer and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106146716A true CN106146716A (en) | 2016-11-23 |
| CN106146716B CN106146716B (en) | 2018-01-19 |
Family
ID=57353353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610377672.3A Active CN106146716B (en) | 2016-05-27 | 2016-05-27 | A kind of OPC B2Molecularly imprinted polymer and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106146716B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107102053A (en) * | 2017-05-25 | 2017-08-29 | 济南大学 | A kind of preparation method of OPC molecular engram sensor |
| CN113292763A (en) * | 2021-06-03 | 2021-08-24 | 江苏徐淮地区徐州农业科学研究所(江苏徐州甘薯研究中心) | Microwave preparation method of anthocyanin magnetic molecularly imprinted polymer |
| CN113385154A (en) * | 2021-07-15 | 2021-09-14 | 吉林化工学院 | Molecular imprinting sol-gel coating fiber tube internal solid phase micro-extraction device and preparation method thereof |
| CN113788871A (en) * | 2021-08-19 | 2021-12-14 | 南方医科大学 | Coordination compound and preparation method and application thereof |
| CN114031590A (en) * | 2021-11-17 | 2022-02-11 | 中北大学 | Method for efficiently preparing high-purity oligomeric proanthocyanidins from sea buckthorn seed meal |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101724097A (en) * | 2009-12-14 | 2010-06-09 | 武汉理工大学 | Chitosan and metal copper ion complex protein-imprinted polymer and preparation method thereof |
| CN105254692A (en) * | 2015-11-27 | 2016-01-20 | 吉首大学 | Method for extracting aucubin and geniposide from eucommia ulmoides peel at same time |
| CN105601789A (en) * | 2016-01-06 | 2016-05-25 | 成洪达 | Rutin-Cu2+ ligand molecularly imprinted polymer and preparation method and application thereof |
-
2016
- 2016-05-27 CN CN201610377672.3A patent/CN106146716B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101724097A (en) * | 2009-12-14 | 2010-06-09 | 武汉理工大学 | Chitosan and metal copper ion complex protein-imprinted polymer and preparation method thereof |
| CN105254692A (en) * | 2015-11-27 | 2016-01-20 | 吉首大学 | Method for extracting aucubin and geniposide from eucommia ulmoides peel at same time |
| CN105601789A (en) * | 2016-01-06 | 2016-05-25 | 成洪达 | Rutin-Cu2+ ligand molecularly imprinted polymer and preparation method and application thereof |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107102053A (en) * | 2017-05-25 | 2017-08-29 | 济南大学 | A kind of preparation method of OPC molecular engram sensor |
| CN107102053B (en) * | 2017-05-25 | 2019-03-05 | 济南大学 | A kind of preparation method of procyanidine molecular engram sensor |
| CN113292763A (en) * | 2021-06-03 | 2021-08-24 | 江苏徐淮地区徐州农业科学研究所(江苏徐州甘薯研究中心) | Microwave preparation method of anthocyanin magnetic molecularly imprinted polymer |
| CN113385154A (en) * | 2021-07-15 | 2021-09-14 | 吉林化工学院 | Molecular imprinting sol-gel coating fiber tube internal solid phase micro-extraction device and preparation method thereof |
| CN113385154B (en) * | 2021-07-15 | 2022-09-27 | 吉林化工学院 | Molecular imprinting sol-gel coating fiber tube internal solid phase micro-extraction device and preparation method thereof |
| CN113788871A (en) * | 2021-08-19 | 2021-12-14 | 南方医科大学 | Coordination compound and preparation method and application thereof |
| CN113788871B (en) * | 2021-08-19 | 2023-10-03 | 南方医科大学 | Coordination compound, preparation method and application thereof |
| CN114031590A (en) * | 2021-11-17 | 2022-02-11 | 中北大学 | Method for efficiently preparing high-purity oligomeric proanthocyanidins from sea buckthorn seed meal |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106146716B (en) | 2018-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106146716A (en) | A kind of OPC B2molecularly imprinted polymer and its preparation method and application | |
| CN102898566B (en) | Preparation method of metal organic framework molecularly imprinted polymer used for enriching trace amounts of Metolcarb | |
| US10010862B2 (en) | Hydrophilic magnetic resin with high specific area, preparation method therefor and application method thereof for rapidly extracting phthalates in water body | |
| CN107118354B (en) | Preparation method and application of ochratoxin metal organic framework-molecular imprinting composite separation medium | |
| CN101177500A (en) | Method for preparing bisphenol A molecular engram polymer | |
| CN102775564B (en) | Preparation method of temperature sensitive type monolithic column with chiral molecule recognition function | |
| CN106483218B (en) | A kind of molecular engram solid phase extraction-liquid chromatogram detects metrifonate and Azodrin method simultaneously | |
| CN101246150B (en) | Tsiklomitsin molecular engram integral column preparation method | |
| CN102731706B (en) | Carbofuran molecularly imprinted microspheres, preparation and application thereof | |
| CN101337960A (en) | Process for extracting matrine form Chinese traditional medicine extract | |
| CN107189011B (en) | Hollow molecules imprinted polymer, solid-phase extraction column and its preparation method and application | |
| CN103232572A (en) | Molecular imprinting polymer for roxarsone detection, and preparation method thereof | |
| CN105130793B (en) | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome | |
| CN102617813A (en) | Preparation and application of sephadex surface apigenin molecular engram sorbing material | |
| CN103224590B (en) | Glabridin molecularly imprinted polymer, as well as preparation method and application thereof | |
| CN103396512A (en) | Hybrid template molecularly imprinted polymer as well as preparation method and application of hybrid template molecularly imprinted solid-phase extraction column | |
| CN108976466A (en) | Hydroxyl pcb molecule imprinted polymer microballoon, solid-phase extraction column and its application containing the microballoon | |
| CN104610502B (en) | The synthetic method of Tea Saponin molecularly imprinted polymer based on methacryl-POSS crosslinking agent | |
| CN101851318B (en) | Preparation method of punicalagin molecular imprinted polymer microspheres | |
| CN106279488A (en) | The preparation of the molecularly imprinted polymer that three kinds of alkaloids of Sophora moocroftiana(Wall．) Benth. Ex Bak. extract simultaneously and extracting process | |
| CN108929302B (en) | Separation method of mixed tocopherol, porous polyion liquid material and preparation method thereof | |
| CN106749903B (en) | A kind of amphiphilic Acetochlor magnetic molecularly imprinted polymer and its preparation method and application | |
| CN105085827A (en) | Preparation method of tanshinol surface molecularly-imprinted polymer | |
| CN104772127B (en) | A kind of preparation method for being directed to the carbon cloth surface molecule print passive sampling film of organic pollution in water environment | |
| CN106632809A (en) | Preparation method for hollow porous type molecularly imprinted material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |