CN107383277B - Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer - Google Patents
Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer Download PDFInfo
- Publication number
- CN107383277B CN107383277B CN201710628730.XA CN201710628730A CN107383277B CN 107383277 B CN107383277 B CN 107383277B CN 201710628730 A CN201710628730 A CN 201710628730A CN 107383277 B CN107383277 B CN 107383277B
- Authority
- CN
- China
- Prior art keywords
- molecular engram
- function monomer
- sulfonylurea
- engram material
- preparation
- 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.)
- Expired - Fee Related
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
- 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
-
- 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
-
- 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
- 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
-
- 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
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer, it is related to sulfonylurea molecular engram material.1- vinyl -3- octylimidazole tetrafluoroborate is function monomer, and ethylene glycol dimethacrylate is crosslinking agent, and dimethyl sulfoxide is pore-foaming agent, obtained molecularly imprinted polymer material.1- vinyl -3- octylimidazole tetrafluoroborate is effectively combined with template molecule triflusulfuronmethyl by hydrogen bond action, add crosslinking agent and pore-foaming agent, polymerization reaction generates three-dimensional network polymer, then eluted template molecule, utilize the binding site selection on molecular engram material, identification, memory target molecule, 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, prepared to have application value by the sulfonylurea weedicide molecularly imprinted material of function monomer of poly ion liquid.
Description
Technical field
The present invention relates to sulfonylurea molecular engram materials, more particularly, to using poly ion liquid as the sulphonyl of function monomer
The preparation of ureas molecular engram material.
Background technique
Sulfonylurea herbicide (Sulfonylurea herbicides, SUHs) is sent out from nineteen eighty-two by DuPont Corporation
Since existing[1-2], because having many advantages, such as that efficient, low volatility, thermal instability are widely used in preventing and kill off the weeds in agricultural product[3]。
As the usage amount and use scope of such herbicide constantly increase, and SUHs is unstable in the environment, is easily degraded, content
Low, the residual in crops has been to be concerned by more and more people the harm of human health[4-6].Therefore, it establishes quickly, efficiently
Sulfonylurea herbicide residual quantity detection method is food-safe, foreign trade development etc. has important meaning
Justice[7].Since actual sample substrate is complicated and SUHs content is extremely low, effective sample must be carried out before carrying out analysis detection
Product pre-treatment.1949, Dickey proposed the concept of " molecular engram " earliest[8].What Wulff was manually synthesized in 1972
Molecularly imprinted polymer has been made in method for the first time[9], molecular engram is just known to everybody.Molecular engram material has good sky
Between three-dimensional configuration, and prepare the advantages that simple, low in cost, 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.
Summary of the invention
The purpose of the present invention is to provide using poly ion liquid as function monomer, to the sulfonylurea herbicide in environmental sample
Agent efficiently extracted using poly ion liquid as the preparation method of the sulfonylurea molecular engram material of function monomer.
The specific steps of the present invention are as follows:
Function monomer and template molecule are mixed, after carrying out prepolymerization, add crosslinking agent and pore-foaming agent, ultrasound at
Solution pours solution in container into then after inflated with nitrogen, it is closed after carry out constant temperature polymerization reaction, then post-process to get with gather from
Sub- liquid is the sulfonylurea molecular engram material of function monomer.
The mass ratio of the function monomer and template molecule is that (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 agent can be 1 ︰ (0.5~1.5)；The function monomer
It can be 1- vinyl -3- octylimidazole tetrafluoroborate, the initiator can be selected from azodiisobutyronitrile or benzoyl peroxide,
Ethylene glycol dimethacrylate can be used in the crosslinking agent；The template molecule can be triflusulfuronmethyl etc., and the pore-foaming agent can
For dimethyl sulfoxide 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 polymerization reaction can be placed in constant temperature polymerization reaction 6 in 60~80 DEG C of baking ovens~for 24 hours；The equation of the polymerization reaction can are as follows:
The specific method of the post-processing can are as follows: the molecular engram material that will acquire is placed in Soxhlet extractor, uses solvent
It extracts, or the molecular engram material that will acquire is placed in solvent, is dipped in liquid without template molecule and impurity detection；It is described molten
Agent can be selected from one of methanol, acetonitrile, ethyl alcohol etc..
For the present invention using triflusulfuronmethyl as template molecule, 1- vinyl -3- octylimidazole tetrafluoroborate is function monomer, second
Diol dimethacrylate is crosslinking agent, and azodiisobutyronitrile is initiator, and dimethyl sulfoxide is pore-foaming agent.By above-mentioned chemical combination
After object mixes by a certain percentage, using in-situ polymerization technology, causes 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- octylimidazole tetrafluoroborate as function monomer
In conjunction with rear eluted template molecule, using the binding site selection on molecular engram material, identification, memory target molecule, to mention
The selectivity of high material realizes effective extraction to sulfonylurea herbicide.
The present invention has synthesized sulfonylurea weedicide molecularly imprinted material using poly ion liquid as function monomer, the trace
Material can carry out efficient selective extraction to SUHs compound, have wide actual application prospect.
The present invention is prepared for the first time using 1- vinyl -3- octylimidazole tetrafluoroborate as function monomer, utilizes " original position " poly-
It closes object technology and prepares poly- (1- vinyl -3- octylimidazole tetrafluoroborate-ethylene glycol dimethacrylate) molecular engram material
Material.1- vinyl -3- octylimidazole tetrafluoroborate is effectively combined with template molecule triflusulfuronmethyl by hydrogen bond action, is added
Crosslinking agent and pore-foaming agent, polymerization reaction generate three-dimensional network polymer, rear eluted template molecule, using on molecular engram material
Binding site selection, identification, memory target molecule, to improve the selectivity of material, realization has sulfonylurea herbicide
Effect extraction.Prepared molecular engram material is simple with preparation simultaneously, permeability is good, low cost and advantages of environment protection,
Therefore sulfonylurea weedicide molecularly imprinted material prepared by the present invention has expected practical application value.
Detailed description of the invention
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 chromatogram of 6 kinds of sulfonylurea herbicides of mark-on 100ppb in the embodiment of the present invention 6.In Fig. 3,
Curve a is direct injected before ultrapure water extracts, 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 schemes object selectively assessment in the embodiment of the present invention 7.In Fig. 4, front row is represented
Non- molecular engram material, heel row represent molecular engram material.
Specific embodiment
Below by embodiment, the present invention is further illustrated.
Embodiment 1
1) react the preparation of mix reagent: the composition of the reaction monomers intermixture is 1- vinyl-by mass percentage
3- octylimidazole tetrafluoroborate 30%, initiator azodiisobutyronitrile 0.5%, crosslinking agent ethylene glycol dimethacrylate
69.5%；In mass ratio, Mo plate Fen ︰ function monomer=1 ︰ 3；Reaction monomers Hun He Ji ︰ pore-foaming agent=1 ︰ 0.5.
2) polymerization reaction: weighing function monomer according to the above ratio and prepolymerization 10min occurs for template molecule mixing, then
Crosslinking agent and pore-foaming agent is added, ultrasound is at uniform solution.Then inflated with nitrogen 3min, by above-mentioned solution implantation glass capillary,
Sealing is placed in 60 DEG C of baking ovens constant temperature polymerization reaction for 24 hours.
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 Soxhlet extractor is utilized, using methanol as solvent extraction
4h。
Embodiment 2
1) react the preparation of mix reagent: the composition of the reaction monomers intermixture is 1- vinyl-by mass percentage
3- octylimidazole tetrafluoroborate 40%, initiator azodiisobutyronitrile 1%, crosslinking agent ethylene glycol dimethacrylate
59%；In mass ratio, Mo plate Fen ︰ function monomer=1 ︰ 6；Reaction monomers Hun He Ji ︰ pore-foaming agent=1 ︰ 1.
2) polymerization reaction: weighing function monomer according to the above ratio and prepolymerization 20min occurs for template molecule mixing, then
It is added crosslinking agent and pore-foaming agent, ultrasound is at uniform solution, then inflated with nitrogen 5min, by above-mentioned solution implantation glass capillary,
Sealing is placed on constant temperature polymerization reaction 12h in 70 DEG C of baking ovens.
3) the molecular engram fiber front end (2cm) obtained in step 2 the post-processing of molecular engram material: is immersed in liquid
Under face, using acetonitrile as solvent, it is dipped in liquid without template molecule and impurity detection.Or Soxhlet extractor is utilized, it is with acetonitrile
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) react the preparation of mix reagent: the composition of the reaction monomers intermixture is 1- vinyl-by mass percentage
3- octylimidazole tetrafluoroborate 50%, initiator benzoyl peroxide 2%, remaining is crosslinking agent ethylene glycol dimethacrylate
48%；In mass ratio, Mo plate Fen ︰ function monomer=1 ︰ 12；Reaction monomers Hun He Ji ︰ pore-foaming agent=1 ︰ 1.5.
2) polymerization reaction: weighing function monomer according to the above ratio and prepolymerization 60min occurs for template molecule mixing, then
Crosslinking agent and pore-foaming agent is added, ultrasound is at uniform solution, and then above-mentioned solution, is poured into the appearance of certain internal diameter by inflated with nitrogen 20min
In device, sealing is placed on constant temperature polymerization reaction 6h in 80 DEG C of baking ovens.
3) post-processing of molecular engram material: being placed in Soxhlet extraction wherein for the molecular engram material that step 2 obtains, with
Ethyl alcohol is solvent, is extracted for 24 hours, 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.), postposition is sealed
For 24 hours, remaining operation can be obtained molecular engram fiber by embodiment 2 to constant temperature polymerization reaction, by four molecules in 70 DEG C of baking ovens
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 tetrafluoroborate by mass percentage
40%, initiator azodiisobutyronitrile 1%, crosslinking agent ethylene glycol dimethacrylate 59%；In mass ratio, reaction monomers are mixed
He Ji ︰ pore-foaming agent=1 ︰ 1.
2) polymerization reaction: reaction monomers intermixture and pore-foaming agent mixing are weighed according to the above ratio, ultrasound is at uniform solution, so
Inflated with nitrogen 5min afterwards, by above-mentioned solution implantation glass capillary, sealing is placed on constant temperature polymerization reaction 12h in 70 DEG C of baking ovens.
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
It prepares and contains 6 kinds of sulfonylurea herbicides (triflusulfuronmethyl, thifensulfuronmethyl, metsulfuron-methyl, chlorsulfuron, prosulfuron, chloropyridines
Sulphur is grand) water sample, mark-on solubility is the aqueous solution 20mL of 100 μ g/L, 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 at 300r/min, takes out fiber at room temperature
Beam desorbs 25min under same revolving speed with 400 μ L acetonitriles/formic acid solution (99.5%/0.5%, V/V).Detect instrument
For Shimadzu high performance liquid chromatograph (Shimadzu, Kyoto, Japan): CBA-20A controller, LC20AD type binary pump,
SPD-M20A DAD detector, SIL-20A autosampler.Chromatographic test strip part: (5 μm of Kromasil C18 chromatographic column
Particle size, 250mm × 4.6mm i.d.)；Overall flow rate is 1.0mL/min；Sample volume is 20 μ L；Mobile phase is acetonitrile
(B) -0.4% phosphate aqueous solution (A)；Gradient elution program are as follows: 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 chromatogram of 6 kinds of sulfonylurea herbicides of mark-on 100ppb in the embodiment of the present invention 6.
Embodiment 7
It prepares and contains 6 kinds of sulfonylureas (triflusulfuronmethyl, thifensulfuronmethyl, metsulfuron-methyl, chlorsulfuron, 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 compound
It is 100 μ g/L.Embodiment 6 is pressed in remaining operation, investigates molecular engram material and non-molecular engram material to above compound
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 (7)
1. using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer, it is characterised in that its specific step
It is rapid as follows: function monomer and template molecule are mixed, after carrying out prepolymerization, add crosslinking agent and pore-foaming agent, it is ultrasonic at
Solution pours solution in container into then after inflated with nitrogen, it is closed after carry out constant temperature polymerization reaction, then post-process to get with gather from
Sub- liquid is the sulfonylurea molecular engram material of function monomer；The mass ratio of the function monomer and template molecule be (3~
12) 1 ︰, function monomer is 30%~50% by mass percentage, and initiator is 0.5%~2.0%, and surplus is crosslinking agent；It is described
Function monomer, initiator and crosslinking agent mixing anabolic reaction monomer intermixture, the quality of the reaction monomers Hun He Ji ︰ pore-foaming agent
Than for 1 ︰ (0.5~1.5)；
The function monomer be 1- vinyl -3- octylimidazole tetrafluoroborate, the initiator be selected from azodiisobutyronitrile or
Benzoyl peroxide, the crosslinking agent use ethylene glycol dimethacrylate；The template molecule is triflusulfuronmethyl, the cause
Hole agent is dimethyl sulfoxide.
2. as described in claim 1 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
The time for being characterized in that the prepolymerization is 10~60min.
3. as described in claim 1 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
The time for being characterized in that the inflated with nitrogen is 3~20min.
4. as described in claim 1 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
It is characterized in that the equation of the polymerization reaction are as follows:
5. as described in claim 1 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
It is characterized in that the constant temperature polymerization reaction is placed in constant temperature polymerization reaction 6 in 60~80 DEG C of baking ovens~for 24 hours.
6. as described in claim 1 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
It is characterized in that the post-processing method particularly includes: the molecular engram material that will acquire is placed in Soxhlet extractor, is mentioned with solvent
It takes, or the molecular engram material that will acquire is placed in solvent, is dipped in liquid without template molecule and impurity detection.
7. as claimed in claim 6 using ionic liquid as the preparation method of the sulfonylurea molecular engram material of function monomer,
It is characterized in that the solvent is selected from one of methanol, acetonitrile, ethyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710628730.XA CN107383277B (en) | 2017-07-28 | 2017-07-28 | Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710628730.XA CN107383277B (en) | 2017-07-28 | 2017-07-28 | Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107383277A CN107383277A (en) | 2017-11-24 |
| CN107383277B true CN107383277B (en) | 2019-11-01 |
Family
ID=60341035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710628730.XA Expired - Fee Related CN107383277B (en) | 2017-07-28 | 2017-07-28 | Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107383277B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110470758B (en) * | 2019-08-14 | 2020-09-08 | 厦门大学 | Device and analysis method for on-line detection of sulfonylurea pesticide residues in environmental water sample |
| 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 |
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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107383277A (en) | 2017-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Olabisi | Polymer compatibility by gas-liquid chromatography | |
| CN102532390B (en) | Triazine weedicide, and metabolite molecular engram polymer microspheres, preparation method and application thereof | |
| Grandy et al. | Development of a hydrophilic lipophilic balanced thin film solid phase microextraction device for balanced determination of volatile organic compounds | |
| Liu et al. | Rheological images of dynamic covalent polymer networks and mechanisms behind mechanical and self-healing properties | |
| Lee et al. | Synthesis and swelling characteristics of pH and thermoresponsive interpenetrating polymer network hydrogel composed of poly (vinyl alcohol) and poly (acrylic acid) | |
| Djozan et al. | Evaluation of a new method for chemical coating of aluminum wire with molecularly imprinted polymer layer. Application for the fabrication of triazines selective solid-phase microextraction fiber | |
| Hashemi-Moghaddam et al. | Solid-phase microextraction of chlorpyrifos in fruit samples by synthesised monolithic molecularly imprinted polymer fibres | |
| CN107383277B (en) | Using poly ion liquid as the preparation of the sulfonylurea molecular engram material of function monomer | |
| CN102711978B (en) | Porous polymer material all in one piece, Its Preparation Method And Use | |
| Djozan et al. | Synthesis and application of high selective monolithic fibers based on molecularly imprinted polymer for SPME of trace methamphetamine | |
| KR101777105B1 (en) | Quantitative Analysis for Oligomers in Polymer using MALDI-TOF Mass analysis | |
| Asgari et al. | Super-porous semi-interpenetrating polymeric composite prepared in straw for micro solid phase extraction of antibiotics from honey, urine and wastewater | |
| Du et al. | Pipette tip-based molecularly imprinted monolith for selective micro-solid-phase extraction of methomyl in environmental water | |
| Pérez-Ramírez et al. | Effect of Temperature on the Cononsolvency of Poly (N-isopropylacrylamide)(PNIPAM) in Aqueous 1-Propanol | |
| Kulyk et al. | Microsampling with a solid-phase extraction cartridge: storage and online mass spectrometry analysis | |
| Wang et al. | α, ω-Diaminoalkanes as models for bases that dicoordinate the proton: An evaluation of the kinetic method for estimating their proton affinities | |
| Li et al. | Poly [hydroxyethyl acrylate-co-poly (ethylene glycol) diacrylate] Monolithic Column for Efficient Hydrophobic Interaction Chromatography of Proteins | |
| Weidner et al. | LC-MALDI-TOF imaging MS: a new approach in combining chromatography and mass spectrometry of copolymers | |
| Doménech et al. | On the existence of different zeolite-associated topological redox isomers. Electrochemistry of the Y zeolite-associated Mn (Salen) N3 complex | |
| CN101649021A (en) | Preparation method and application of molecular imprinting polymer microspheres for Chlorsulfuron | |
| CN103599755B (en) | Phenolethanolamine A molecular engram film and preparation method thereof and application | |
| Bogdanowicz et al. | Rapid quantification of 2, 4-dichlorophenol in river water samples using molecularly imprinted polymers coupled to ambient plasma mass spectrometry | |
| Koziol et al. | Structural and gelation characteristics of metallo-supramolecular polymer model-network hydrogels probed by static and dynamic light scattering | |
| CN102731706B (en) | Carbofuran molecularly imprinted microspheres, preparation and application thereof | |
| CN107014888A (en) | The method that trace materials in sample to be tested is analyzed using molecular engram film electrospray ionization mass spectrometry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20191101 Termination date: 20200728 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |