CN107383277A - Preparation using poly ion liquid as the sulfonylurea molecular engram material of function monomer - Google Patents
Preparation using poly ion liquid as the sulfonylurea molecular engram material of function monomer Download PDFInfo
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- CN107383277A CN107383277A CN201710628730.XA CN201710628730A CN107383277A CN 107383277 A CN107383277 A CN 107383277A CN 201710628730 A CN201710628730 A CN 201710628730A CN 107383277 A CN107383277 A CN 107383277A
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- 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
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- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/042—Elimination of an organic solid phase
- C08J2201/0424—Elimination of an organic solid phase containing halogen, nitrogen, sulphur or phosphorus atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2335/00—Characterised by the use of homopolymers or 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, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J2335/02—Characterised by the use of homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2343/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Derivatives of such polymers
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Abstract
Preparation using poly ion liquid as the sulfonylurea molecular engram material of function monomer, is related to sulfonylurea molecular engram material.The octylimidazole tetrafluoroborate of 1 vinyl 3 is function monomer, and ethylene glycol dimethacrylate is crosslinking agent, and dimethyl sulfoxide (DMSO) is pore-foaming agent, obtained molecularly imprinted polymer material.The octylimidazole tetrafluoroborate of 1 vinyl 3 is effectively combined with template molecule triflusulfuronmethyl by hydrogen bond action, add crosslinking agent and pore-foaming agent, polymerisation generates three-dimensional network polymer, then eluted template molecule, utilize the binding site selection on molecular engram material, identification, memory target molecule, so as to improve the selectivity of material, effective extraction to sulfonylurea herbicide is realized.Prepared molecular engram material, which has, simultaneously prepares simple, reproducible, inexpensive and advantages of environment protection, and the prepared sulfonylurea weedicide molecularly imprinted material using poly ion liquid as function monomer has application value.
Description
Technical field
The present invention relates to sulfonylurea molecular engram material, more particularly, to the sulphonyl using poly ion liquid as function monomer
The preparation of ureas molecular engram material.
Background technology
Sulfonylurea herbicide (Sulfonylurea herbicides, SUHs) is sent out from nineteen eighty-two by du pont company
Since existing[1-2], because having the advantages that efficient, low volatility, thermal instability are widely used in preventing and kill off the weeds in agricultural product[3]。
Constantly increase with the usage amount and use range of such herbicide, and SUHs is unstable in the environment, is easily degraded, content
Low, harm of the residual to human health in crops has been to be concerned by more and more people[4-6].Therefore, establish quick, efficient
Sulfonylurea herbicide residual quantity detection method is food-safe, foreign trade development etc. has important meaning
Justice[7].Because actual sample substrate is complicated and SUHs contents are extremely low, therefore, effective sample must be carried out before analysis detection is carried out
Product pre-treatment.1949, Dickey proposed the concept of " molecular engram " earliest[8].What Wulff manually synthesized in 1972
Molecularly imprinted polymer has been made in method first[9], molecular engram is just known to everybody.Molecular engram material has good sky
Between three-dimensional configuration, and prepare the advantages that simple, cost is cheap, selectivity is high, stability is good.
Referring to document：
[1]Z.He,D.Liu,R.Li,Z.Zhou,P.Wang,Anal.Chim.Acta 747(2012)29.
[2]M.Bouri,M.Gurau,R.Salghi,I.Cretescu,M.Cretescu,A.Rios,
Anal.Bioanal.Chem.397(2012)1529.
[3]M.H.Russell,J.L.Saladini,F.Lichtner,Pestic.Outlook 13(2002)166.
[4]A.K.Sarmah,A.J.Sabadie,J.Agri.Food Chem.50(2002)6253.
[5]J.L.Tadeo,C.Sánchez-Brunete,R.A.Pérez,M.D.Fernández,J.Chromatogr.A
882(2000)175.
[6]P.Degelmann,J.Wenger,R.Niessner,D.Knopp,Environ.Sci.Technol.38
(2004)6795.
[7]T.Cserhati,E.Forgacs,Z.Deyl,I.Miksik,A.Eckhardt,
Biomed.Chromatogr.A 18(2004)350.
[8]F.H.Dickey,P.Natl.Acad.Sci.35(1949)227.
[9]G.Wulff,A.Sarhan,Angew.Chem.84(1972)364.
The content of the invention
It is an object of the invention to provide using poly ion liquid as function monomer, to the sulfonylurea herbicide in environmental sample
The preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer that agent is efficiently extracted.
The present invention's comprises the following steps that：
Function monomer and template molecule are mixed, after carrying out prepolymerization, add crosslinking agent and pore-foaming agent, ultrasound into
Solution, then after inflated with nitrogen, solution is poured into container, carries out constant temperature polymerisation after closed, then post-process, that is, be able to gather from
Sub- liquid is the sulfonylurea molecular engram material of function monomer.
The mass ratio of the function monomer and template molecule is (3~12) ︰ 1, function monomer is 30% by mass percentage
~50%, initiator is 0.5%~2.0%, and surplus is crosslinking agent；The function monomer, initiator and crosslinking agent mixing composition
Reaction monomers intermixture, the mass ratio of the reaction monomers Hun He Ji ︰ pore-foaming agents can be 1 ︰ (0.5~1.5)；The function monomer
Can be 1- vinyl -3- octylimidazole tetrafluoroborates, the initiator may be selected from azodiisobutyronitrile or benzoyl peroxide,
The crosslinking agent can use ethylene glycol dimethacrylate；The template molecule can be triflusulfuronmethyl etc., and the pore-foaming agent can
For dimethyl sulfoxide (DMSO) etc..
The time of the prepolymerization can be 10~60min, and the time of the inflated with nitrogen can be 3~20min；The perseverance
Warm polymerisation can be placed in 6~24h of constant temperature polymerisation in 60~80 DEG C of baking ovens；The equation of the polymerisation can be：
The specific method of the post processing can be：The molecular engram material of acquisition is placed in apparatus,Soxhlet's, uses solvent
Extraction, or the molecular engram material of acquisition is placed in solvent, it is dipped in liquid without template molecule and impurity detection；It is described molten
Agent may be selected from one kind in methanol, acetonitrile, ethanol etc..
The present invention is using triflusulfuronmethyl as template molecule, and 1- vinyl -3- octylimidazoles tetrafluoroborates are function monomer, second
Diol dimethacrylate is crosslinking agent, and azodiisobutyronitrile is initiator, and dimethyl sulfoxide (DMSO) is pore-foaming agent.By above-mentioned chemical combination
After thing mixes by a certain percentage, using in-situ polymerization technology, trigger polymerization certain time at a certain temperature, after treatment may be used
Obtain molecular engram material.
Molecular engram material preparation of the present invention is simple, extraction selectivity is good, inexpensive, reproducible；The material
It is effective by hydrogen bond action and template molecule triflusulfuronmethyl using 1- vinyl -3- octylimidazoles tetrafluoroborates as function monomer
With reference to rear eluted template molecule, using the binding site selection on molecular engram material, identification, memory target molecule, so as to carry
The selectivity of high material, realize effective extraction to sulfonylurea herbicide.
The present invention has synthesized sulfonylurea weedicide molecularly imprinted material, the trace using poly ion liquid as function monomer
Material can carry out efficient selective extraction to SUHs compounds, have wide actual application prospect.
The present invention is prepared using 1- vinyl -3- octylimidazoles tetrafluoroborates as function monomer first, utilizes " original position " poly-
Compound technology prepares poly- (1- vinyl -3- octylimidazoles tetrafluoroborate-ethylene glycol dimethacrylate) molecular engram material
Material.1- vinyl -3- octylimidazoles tetrafluoroborate is effectively combined with template molecule triflusulfuronmethyl by hydrogen bond action, is added
Crosslinking agent and pore-foaming agent, polymerisation generation three-dimensional network polymer, rear eluted template molecule, using on molecular engram material
Binding site selection, identification, memory target molecule, so as to improve the selectivity of material, realize has to sulfonylurea herbicide
Effect extraction.Simultaneously prepared molecular engram material, which has, prepares that simple, permeability is good, low cost and advantages of environment protection,
Therefore the sulfonylurea weedicide molecularly imprinted material prepared by the present invention has expected actual application value.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of molecular engram material in the embodiment of the present invention 2.In Fig. 1, main suction from left to right
The wave number for receiving peak is respectively 2957cm-1、2930cm-1、1734cm-1、1388cm-1、1262cm-1、1162cm-1、761cm-1。
Fig. 2 is the scanning electron microscope (SEM) photograph of molecular engram material in inventive embodiments 2.
Fig. 3 is the separation chromatography figure of 6 kinds of sulfonylurea herbicides of mark-on 100ppb in the embodiment of the present invention 6.In figure 3,
Curve a is direct injected before ultra-pure water extraction, and curve b is sample introduction after the extraction of non-molecular engram material, and curve c is molecular engram material
After material extraction.
Fig. 4 is that molecular engram material selectively assesses figure to object in the embodiment of the present invention 7.In Fig. 4, it is front-seat to represent
Non- molecular engram material, heel row represent molecular engram material.
Embodiment
Below by embodiment, the present invention is further illustrated.
Embodiment 1
1) preparation of mix reagent is reacted：The composition of the reaction monomers intermixture by mass percentage for 1- vinyl-
3- octylimidazoles tetrafluoroborate 30%, initiator azodiisobutyronitrile 0.5%, crosslinking agent ethylene glycol dimethacrylate
69.5%；In mass ratio, the ︰ 3 of Mo plates Fen ︰ function monomers=1；The ︰ 0.5 of reaction monomers Hun He Ji ︰ pore-foaming agents=1.
2) polymerisation：Function monomer is weighed according to the above ratio and prepolymerization 10min occurs for template molecule mixing, then
Crosslinking agent and pore-foaming agent are added, it is ultrasonic into uniform solution.Then inflated with nitrogen 3min, by above-mentioned solution implantation glass capillary,
Constant temperature polymerisation 24h in 60 DEG C of baking ovens is placed in after sealing.
3) post processing of molecular engram material：The molecular engram material obtained in step 2 is immersed under liquid level, with first
Alcohol is solvent, is dipped to template molecule and free from admixture detection in liquid.Or using apparatus,Soxhlet's, using methanol as solvent extraction
4h。
Embodiment 2
1) preparation of mix reagent is reacted：The composition of the reaction monomers intermixture by mass percentage for 1- vinyl-
3- octylimidazoles tetrafluoroborate 40%, initiator azodiisobutyronitrile 1%, crosslinking agent ethylene glycol dimethacrylate
59%；In mass ratio, the ︰ 6 of Mo plates Fen ︰ function monomers=1；The ︰ 1 of reaction monomers Hun He Ji ︰ pore-foaming agents=1.
2) polymerisation：Function monomer is weighed according to the above ratio and prepolymerization 20min occurs for template molecule mixing, then
Adding crosslinking agent and pore-foaming agent, ultrasound is into uniform solution, then inflated with nitrogen 5min, by above-mentioned solution implantation glass capillary,
Constant temperature polymerisation 12h in 70 DEG C of baking ovens is placed in after sealing.
3) post processing of molecular engram material：The molecular engram fiber front end (2cm) obtained in step 2 is immersed in liquid
Under face, using acetonitrile as solvent, it is dipped in liquid without template molecule and impurity detection.Or using apparatus,Soxhlet's, using acetonitrile as
Solvent extraction 12h.
Fig. 1 is the infrared spectrogram of prepared molecular engram material, and Fig. 2 is the scanning electron microscope (SEM) photograph of the molecular engram material.
Embodiment 3
1) preparation of mix reagent is reacted：The composition of the reaction monomers intermixture by mass percentage for 1- vinyl-
3- octylimidazoles tetrafluoroborate 50%, initiator benzoyl peroxide 2%, remaining is crosslinking agent ethylene glycol dimethacrylate
48%；In mass ratio, the ︰ 12 of Mo plates Fen ︰ function monomers=1；The ︰ 1.5 of reaction monomers Hun He Ji ︰ pore-foaming agents=1.
2) polymerisation：Function monomer is weighed according to the above ratio and prepolymerization 60min occurs for template molecule mixing, then
Add crosslinking agent and pore-foaming agent, ultrasound is into uniform solution, then inflated with nitrogen 20min, and above-mentioned solution is poured into the appearance of certain internal diameter
Constant temperature polymerisation 6h in 80 DEG C of baking ovens is placed in device, after sealing.
3) post processing of molecular engram material：The molecular engram material that step 2 obtains is placed in surname extraction wherein, with
Ethanol is solvent, extracts 24h, or molecular engram material is placed in above-mentioned solvent, is dipped in liquid without template molecule and miscellaneous
Quality inspection goes out.
Embodiment 4
Reaction solution is prepared by embodiment 2, is then injected into capillary glass tube (100 × 0.5mm i.d.), sealing is rearmounted
The constant temperature polymerisation 24h in 70 DEG C of baking ovens, remaining operation can obtain molecular engram fiber by embodiment 2, by four molecules
Molecular engram fibre bundle is prepared in the binding of trace fiber together.
Embodiment 5
1) composition of the reaction monomers intermixture is 1- vinyl -3- octylimidazole tetrafluoroborates by mass percentage
40%, initiator azodiisobutyronitrile 1%, crosslinking agent ethylene glycol dimethacrylate 59%；In mass ratio, reaction monomers are mixed
The ︰ 1 of He Ji ︰ pore-foaming agents=1.
2) polymerisation：Reaction monomers intermixture and pore-foaming agent mixing are weighed according to the above ratio, and ultrasound is into uniform solution, so
Inflated with nitrogen 5min afterwards, constant temperature polymerisation 12h in 70 DEG C of baking ovens in above-mentioned solution implantation glass capillary, will be placed in after sealing.
3) post processing of non-molecular engram extraction：The non-molecular engram fiber front end (2cm) obtained in step 2 is submerged
Under liquid level, using acetonitrile as solvent, it is dipped to free from admixture in liquid and detects, then bundle same four non-molecular engram fibers
Non- molecular engram fibre bundle is obtained together.
Embodiment 6
Containing 6 kinds of sulfonylurea herbicides, (triflusulfuronmethyl, thifensulfuronmethyl, metsulfuron-methyl, chlorine sulphur are grand, prosulfuron, chloropyridine for preparation
Sulphur is grand) water sample, mark-on solubility is 100 μ g/L aqueous solution 20mL, is respectively implanted the molecular engram fiber prepared by embodiment 4
Beam and the non-molecular engram fibre bundle prepared by embodiment 5, the stirring extraction 40min under 300r/min, takes out fiber at room temperature
Beam desorbs 25min with 400 μ L acetonitriles/formic acid solution (99.5%/0.5%, V/V) under same rotating speed.Detect instrument
For Shimadzu high performance liquid chromatographs (Shimadzu, Kyoto, Japan)：CBA-20A controllers, LC20AD type binary pumps,
SPD-M20A DAD detectors, SIL-20A automatic samplers.Chromatographic test strip part：(5 μm of Kromasil C18 chromatographic columns
Particle size, 250mm × 4.6mm i.d.)；Overall flow rate is 1.0mL/min；Sample size is 20 μ L；Mobile phase is acetonitrile
(B) -0.4% phosphate aqueous solution (A)；Gradient elution program is：0~5min, 30%B；5~10min, 30%~55%B；10~
13min, 55%~60%B；13~15min, 60%B；15~18min, 60%~90%B；18~25min, 90%~30%
B；25~28min, 30%B.
Fig. 3 is the separation chromatography figure of 6 kinds of sulfonylurea herbicides of mark-on 100ppb in the embodiment of the present invention 6.
Embodiment 7
Prepare containing 6 kinds of sulfonylureas (triflusulfuronmethyl, thifensulfuronmethyl, metsulfuron-methyl, chlorine sulphur are grand, prosulfuron, chloropyridine sulphur are grand)
Water sample and 5 kinds of reference compound (prometryn, Simanex, atrazine, Garagard, benzene) water samples, the spiked levels of above-claimed cpd
It is 100 μ g/L.Embodiment 6 is pressed in remaining operation, investigates molecular engram material and non-molecular engram material to above-claimed cpd
Extraction ability.
Fig. 4 is molecular engram in the embodiment of the present invention 7 and non-molecular engram material to object selectivity comparison diagram.
Claims (8)
1. using poly ion liquid as the preparation method of the sulfonylurea molecular engram material of function monomer, it is characterised in that its is specific
Step is as follows：Function monomer and template molecule are mixed, after carrying out prepolymerization, add crosslinking agent and pore-foaming agent, ultrasound
Into solution, then after inflated with nitrogen, solution is poured into container, constant temperature polymerisation is carried out after closed, then is post-processed, that is, is gathered
Ionic liquid is the sulfonylurea molecular engram material of function monomer.
2. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the mass ratio of the function monomer and template molecule for (3~12) ︰ 1, by mass percentage function monomer be
30%~50%, initiator is 0.5%~2.0%, and surplus is crosslinking agent；The function monomer, initiator and crosslinking agent mixing
Anabolic reaction monomer intermixture, the mass ratio of the reaction monomers Hun He Ji ︰ pore-foaming agents is 1 ︰ (0.5~1.5)；The function list
Body is 1- vinyl -3- octylimidazole tetrafluoroborates, and the initiator is selected from azodiisobutyronitrile or benzoyl peroxide, institute
State crosslinking agent and use ethylene glycol dimethacrylate；The template molecule is triflusulfuronmethyl, and the pore-foaming agent is that dimethyl is sub-
Sulfone.
3. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the time of the prepolymerization is 10~60min.
4. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the time of the inflated with nitrogen is 3~20min.
5. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the equation of the polymerisation is：
6. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the constant temperature polymerisation is placed in 6~24h of constant temperature polymerisation in 60~80 DEG C of baking ovens.
7. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 1,
It is characterized in that the specific method of the post processing is：The molecular engram material of acquisition is placed in apparatus,Soxhlet's, uses solvent
Extraction, or the molecular engram material of acquisition is placed in solvent, it is dipped in liquid without template molecule and impurity detection.
8. the preparation method using poly ion liquid as the sulfonylurea molecular engram material of function monomer as claimed in claim 7,
It is characterized in that the one kind of the solvent in methanol, acetonitrile, ethanol.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110470758A (en) * | 2019-08-14 | 2019-11-19 | 厦门大学 | Sulfonylurea agriculture residual device and analysis method in a kind of on-line checking environmental water sample |
| CN110903433A (en) * | 2019-12-16 | 2020-03-24 | 中国农业科学院农业质量标准与检测技术研究所 | Preparation method of sulfonamide based on aminopropyl-3-methylimidazole and synergist molecularly imprinted polymer thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101716495A (en) * | 2009-12-17 | 2010-06-02 | 南开大学 | Sulfonylurea weedicide molecularly imprinted polymer microballoon and preparation method thereof |
| CN102382248A (en) * | 2010-09-06 | 2012-03-21 | 天津科技大学 | Preparation method of chlorsulfuron molecular imprinting polymer |
-
2017
- 2017-07-28 CN CN201710628730.XA patent/CN107383277B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101716495A (en) * | 2009-12-17 | 2010-06-02 | 南开大学 | Sulfonylurea weedicide molecularly imprinted polymer microballoon and preparation method thereof |
| CN102382248A (en) * | 2010-09-06 | 2012-03-21 | 天津科技大学 | Preparation method of chlorsulfuron molecular imprinting polymer |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110470758A (en) * | 2019-08-14 | 2019-11-19 | 厦门大学 | Sulfonylurea agriculture residual device and analysis method in a kind of on-line checking environmental water sample |
| CN110903433A (en) * | 2019-12-16 | 2020-03-24 | 中国农业科学院农业质量标准与检测技术研究所 | Preparation method of sulfonamide based on aminopropyl-3-methylimidazole and synergist molecularly imprinted polymer thereof |
| CN110903433B (en) * | 2019-12-16 | 2021-07-13 | 中国农业科学院农业质量标准与检测技术研究所 | Preparation method of sulfonamide based on aminopropyl-3-methylimidazole and synergist molecularly imprinted polymer thereof |
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