CN108675981A - The virtual template molecular compound of the mould toxin of rod method and the molecularly imprinted polymer prepared using the compound - Google Patents

The virtual template molecular compound of the mould toxin of rod method and the molecularly imprinted polymer prepared using the compound Download PDF

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CN108675981A
CN108675981A CN201810420088.0A CN201810420088A CN108675981A CN 108675981 A CN108675981 A CN 108675981A CN 201810420088 A CN201810420088 A CN 201810420088A CN 108675981 A CN108675981 A CN 108675981A
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rod method
molecular compound
compound
virtual template
mould toxin
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邓晓东
孙成均
何纬
常晓松
张薇薇
樊学军
田绿波
高国龙
刘杨
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Sichuan International Travel Sanitary Health-Care Center
Sichuan University
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Sichuan International Travel Sanitary Health-Care Center
Sichuan University
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    • 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
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses the virtual template molecular compounds of the mould toxin of rod method；And the molecularly imprinted polymer of the mould toxin of rod method prepared using the compound；Utilize bioisosterism, the principle that can get or be readily synthesized using business, design noval chemical compound simultaneously passes through commercial reagent one-step synthesis, virtual alternate template as rod method phenol (AOH), it is synthesized for molecularly imprinted polymer, this greatly reduces the cost of molecularly imprinted polymer production.

Description

It the virtual template molecular compound of the mould toxin of rod method and is prepared using the compound Molecularly imprinted polymer
Technical field
The invention belongs to the virtual template molecular compound of polymeric material field more particularly to the mould toxin of rod method and adopt The molecularly imprinted polymer prepared with the compound.
Background technology
The main object of mycotoxin pollution is grain, food and feed, these directly influence human life, also to poultry Poultry product has significant impact.In order to control and monitor the pollution of mycotoxin, other than taking certain prevention and detoxification measure, To detection technique, higher requirements are also raised.There are many detection method of mycotoxin, summed up biological detection method, chemistry Analytic approach, instrumental method and immunoassay etc., from initially based on thin-layered chromatography, develop to gas chromatography, efficiently Liquid chromatography, immunology detection technology (mainly include radioimmunoassay detection technology, immunoenzyme technics, immunofluorescence technique and Immunoelectronmicroscopy etc.) etc. a variety of methods it is commonly used.But it is relatively simple that these detection methods are generally only applicable to matrix The detection of toxin in sample, the sample various for metabolite type, matrix is complicated then interfere greatly, and false positive results are more, inspection Limit is surveyed to be difficult to meet detection needs.
The appearance of molecular imprinting technology (Molecular imprinting technique, MIT) and develop into fungi poison The rapid extraction and purification of element provide a new approach, prepare with the technology and polymerize with what mycotoxin was specifically bound Object not only makes up the expensive solid-phase extraction column with customary filler of immune affinity column if being applied in solid-phase extraction column The defects such as specificity is poor, the rate of recovery is low, and high temperature resistant, acid and alkali-resistance and reusable, also can be used as identification original paper and prepare and exist The biosensor that line is quickly detected, reused can meet all kinds of different substrates samples such as food, feed, cereal and Chinese medicine The analysis of product.
Molecular engram is just derived from molecular recognition theory and develops rapidly an emerging cross discipline, it is with oversubscription Based on sub- chemistry and polymer chemistry, multi-door such as physical chemistry, material science, analytical chemistry and biochemistry is related to Section.Molecular imprinting technology refer to for obtain in steric configuration and binding site with a certain target compound (template molecule or print Mark molecule) technology of preparing of high molecular polymer that exactly matches, it is visually likened to manufacture identification " molecule key " " artificial lock ".Then molecularly imprinted polymer is also referred to as plastics antibody, it both had similar biological antibody high-affinity and Selectivity, and overcomes the anti-adverse environment ability not available for natural molecule identification system, show stability it is good, using the longevity The advantages that life is long, manufacturing cost is low and has a wide range of application.In the latest 20 years, with supramolecular chemistry, polymer chemistry, biology The deep development of the subjects such as chemistry, quantum chemistry and computer technology, MIT method for producing polymer, print identification mechanism, point Submodule intends theoretic discussion and its all makes significant progress in the application study of the multiple fields such as medicine, environment and Food Science, Application especially in analytical chemistry.
But really realize that the type of industrialization is seldom at present, the research of most of mycotoxin-MIP is still in experiment rank Section.Its reason essentially consists in：On the one hand, from the point of view of mycotoxin nature：(1) due to the fungi as template molecule Toxin has extremely strong toxicity more, and low dose of intake can generate human body prodigious harm, and with the MIP of other substances Preparation is very different, and the price of mycotoxin sterling is very expensive, even according to the ampoule for usually preparing MIP It is also surprising that it, which spends,；(2) some fungi toxin easily occurs character change or is decomposed under ultraviolet light or heat effect, thus It is difficult to as molecular template；(3) molecular weight of most mycotoxins is larger, and comparatively molecular volume is larger, thus routine side When method carries out molecular engram, it is unapparent to easily cause trace profile, to raise non-specific adsorption ability.Mycotoxin itself Property is limited to and the research of trace system screened difficult both sides reason and constrain mycotoxin-MIP.For mycotoxin The limitation for itself being not suitable for doing template molecule mostly uses alternate template method and solves the problems, such as this at present, i.e. selection and mycotoxin knot The similar compound of structure is to prepare mycotoxin-MIP, while the method also can avoid directly using mycotoxin conduct as template The template leakage problems that template occurs.
Rod method mould (Alternaria) is a kind of fungi being distributed widely in soil and various crops, can be caused cold The corruption of the veterinary antibiotics of Tibetan is pathogenic bacteria important during one of most common fungi of contaminated food and Ci trus growth One of.Its toxic metabolic products is more complicated, up to more than 70 kinds, is referred to as the mould toxin of rod method.Wherein rod method mycin (altenuene, ALT), rod method (alternariol, AOH), tentoxin (tentoxin), rod method phenol methyl ether (alternariolmonomethyl ether, AME) is 4 kinds of main mould toxin of rod method, these toxin have cell toxicant Property, there are embryotoxicity and teratogenesis etc. to animal, it is larger to human health damage.
It is low dose of but since there is extremely strong toxicity as the rod method phenol (Alternariol, AOH) of template molecule Intake prodigious harm can be generated to human body, and be very different with the MIP of other substances preparations, AOH sterlings Price it is very expensive, even according to usually prepares MIP ampoule its spend and it is surprising.Therefore pass through commercially available examination It is very necessary for molecularly imprinted polymer synthesis that agent synthesizes virtual alternate template replacement AOH.
Invention content
It is an object of the invention to：There is extremely strong toxicity for the above-mentioned rod method phenol as template molecule, it is low dose of Intake prodigious harm, and the very expensive phenomenon of price of AOH sterlings can be generated to human body, it is caused according to usual system The ampoule of standby MIP its spend very expensive problem, the present invention to provide the virtual template molecule chemical combination of the mould toxin of rod method Object.
It is a further object to provide a kind of molecularly imprinted polymers prepared using the compound.
The technical solution adopted by the present invention is as follows：The virtual template molecular compound of the mould toxin of rod method, the virtual mould The chemical structure of general formula (III) of plate molecular compound：
Wherein R1It is less than or equal to 4 alkyl for-H or carbon atom；R2For halogen atom ,-NH2, or-CH3；R3For halogen atom ,- NH2, or-CH3。
Preferably, the R2For halogen atom；R3For halogen atom.
Preferably, the R2For-the F in halogen atom；R3Also it is-F in halogen atom.
The preparation method of the virtual template molecular compound of the mould toxin of rod method, includes the following steps：Chemical compounds I and chemical combination Object II is in NaOH and CuSO4Under conditions of, by being esterified and replacing cyclization, virtual template molecular compound III is prepared；Its Chemical equation is as follows：
The molecularly imprinted polymer of the mould toxin of rod method, the molecularly imprinted polymer of the mould toxin of rod method pass through as follows Step is made：
(1) monomer-template molecule compound is prepared：Weigh the one such virtual mould of any one of Claim 1-3 Plate molecular compound is template, is put into round-bottomed flask, is (2~5) with volume ratio:1 acetonitrile/toluene dissolves for solvent, then Function monomer methacrylic acid is added, stirs 1h at room temperature, monomer-template molecule compound is made；
(2) cross-linked polymer is prepared：Continue that dimethacrylate ethanedioic acid ester is added in the round-bottomed flask, then adds Enter azodiisobutyronitrile, mixture ultrasound deaerates 8~15min, then be placed on 0~4 DEG C of ice-water bath lead to nitrogen be bubbled deoxygenation 5~ 20min after sealing, then is stirred to react under 50~80 DEG C of reaction temperature for 24 hours, after reaction stops, then rotating speed be 8000~ 15~20min is centrifuged under 10000rpm, collection obtains the particle of cross-linked polymer；
(3) it demoulds：Using the volume ratio (6~9) of methanol/acetic acid:1 mixed solvent, supersound washing at normal temperatures 20~ Virtual template molecular compound in particles of the 40min to extract the cross-linked polymer repeats the supersound washing until upper Until clear liquid can't detect virtual template molecular compound；
(4) dry：The extremely neutral of demoulding post-crosslinking polymer finally is washed with methanol, is 45~50 in temperature after suction filtration It is dried in vacuo 20~28h at DEG C, obtains the molecularly imprinted polymer of the mould toxin of rod method.
Preferably, the virtual template molecular compound and the ratio of the amount of the substance of function monomer methacrylic acid are 1:(2 ~100), the methacrylic acid and the ratio of the amount of the substance of dimethacrylate ethanedioic acid ester are 1~(1:1000), described two The ratio of the amount of the substance of methacrylic acid ethanedioic acid ester and azodiisobutyronitrile is 40:(0.5~1.5).
Preferably, the virtual template molecular compound and the ratio of the amount of the substance of function monomer methacrylic acid are 1:(5 ~80), the methacrylic acid and the ratio of the amount of the substance of dimethacrylate ethanedioic acid ester are 1:(200~600), described two The ratio of the amount of the substance of methacrylic acid ethanedioic acid ester and azodiisobutyronitrile is 40:(0.8~1.2).
In conclusion by adopting the above-described technical solution, the beneficial effects of the invention are as follows：
1. utilizing bioisosterism, the principle that can get or be readily synthesized using business, design noval chemical compound is simultaneously It is synthesized for molecularly imprinted polymer as the virtual alternate template of rod method phenol (AOH) by commercial reagent one-step synthesis, This greatly reduces the cost of production；
2. compared with AOH, pass through the R in the virtual template molecular compound structural formula of the mould toxin of rod method2And R3It adopts at place With halogen atom ,-NH2, or-CH3- OH the bases in AOH molecular structures are substituted, the toxicity of AOH is on the one hand greatly reduced, it is another Aspect increase virtual template molecular compound stability, make its be not susceptible under ultraviolet light or heat effect shape change or Decompose, to improve the molecularly imprinted polymer and AOH that are prepared using the virtual template molecular compound combination performance；
3. the R in the structural formula of the virtual template molecular compound of the mould toxin of rod method1Place using carbon atom be less than etc. In 4 alkyl compare with for-H atom, the molecularly imprinted polymer prepared, detect use when and AOH combination Performance is more high, and chief reason improves virtual template molecular compound and improves the adsorption capacity of function monomer, To keep trace profile more apparent.
Description of the drawings
Examples of the present invention will be described by way of reference to the accompanying drawings, wherein：
Fig. 1 is DMIP-F scanning electron microscope (SEM) photographs；
Fig. 2 is DMIP-6 scanning electron microscope (SEM) photographs；
Fig. 3 is DNIP-1 scanning electron microscope (SEM) photographs.
Specific implementation mode
All features disclosed in this specification or disclosed all methods or in the process the step of, in addition to mutually exclusive Feature and/or step other than, can combine in any way.
Embodiment 1
The preparation of virtual template molecular compound DSM-1
The bromo- 4,5- difluoro-benzoic acids 7.2mmol (1.70g) of 2- are taken to be dissolved in Meta-dihydroxybenzene 16.8mmol (1.85g) In 8.5mL NaOH (16.8mmol, 0.672g) solution, 80 DEG C of reaction 30min are heated to, addition mass fraction is 5%CuSO4 2.9mL after precipitation is formed, stirs 10min, is cooled to room temperature, and with 1.8mL concentrated hydrochloric acid neutralization reaction liquid, filtering, 10mL is washed, 3mL methanol is washed, solid drying, cooling to stir 10min at 50 DEG C of 15mL methanol, and filtering obtains virtual template molecule chemical combination Object DSM-1, DSM-1 yield：68%；Its chemical equation is as follows：
1H NMR(400MHz,DMSO-d6)δ:6.69~6.70 (d, 1H, Ar-H), 6.79-6.81 (m, 1H, Ar-H), 8.00-8.05(m,2H,Ar-H),8.25-8.30(m,1H,Ar-H),10.62(s,1H,-OH)ppm；MS-ESI (negative),m/z；calculated for C13H6F2O3,[M-H]–:248.0；found:247.1.
Embodiment 2
The preparation of virtual template molecular compound DSM-5
Take the bromo- 4,5- difluoro-benzoic acids 7.2mmol (1.70g) of 2- and 3,5- dihydroxytoluenes 16.8mmol (2.085g) molten Solution (in 16.8mmol, 0.672g solution, is heated to 80 DEG C of reaction 30min, it is 5% that mass fraction, which is added, in 8.5mL NaOH CuSO42.9mL after precipitation is formed, stirs 10min, is cooled to room temperature, with 1.8mL concentrated hydrochloric acid neutralization reaction liquid, filtering, 10mL Washing, 3mL methanol washes, solid drying, and to stir 10min at 50 DEG C of 15mL methanol, cooling, virtual template molecule is made in filtering Compound DSM-5, DST-5 yield：63%；Its chemical equation is as follows：
1H NMR(400MHz,DMSO-d6)δ:2.70(s,3H,-CH3) 6.58~6.59 (d, 1H, Ar-H), 6.67-6.68 (d,1H,Ar-H),8.10-8.17(m,2H,Ar-H),10.38(s,1H,-OH)ppm；MS-ESI(negative),m/z； calculated for C14H8F2O3,[M-H]–:262.0；found:261.1.
Embodiment 3
The preparation of molecularly imprinted polymer DMIP-F
Virtual template molecular compound DSM-1 0.5mmol (124mg) are weighed in 150mL round-bottomed flasks, using 50mL Volume ratio acetonitrile/toluene=3:1 (v/v) be solvent dissolving, add 2mmol function monomers methacrylic acid (MAA, After 172.2mg), 1h is stirred at room temperature；Continue that dimethacrylate ethanedioic acid ester 1.98g is added in the round-bottomed flask, then Azodiisobutyronitrile (AIBN) 72mg, mixture ultrasound degassing 10min is added, then is placed on 0~4 DEG C of ice-water bath and leads to nitrogen bubbling Deoxygenation 10min after sealing, then is stirred to react for 24 hours under conditions of 60 DEG C；After reaction stops, then in the case where rotating speed is 10000rpm 15min is centrifuged, collection obtains the particle of cross-linked polymer；With methanol/acetic acid=9:The mixed solvent extraction template point of 1 (v/v) Son, supersound washing 30min, repeats the supersound washing until supernatant can't detect virtual template molecular compound at normal temperatures Until (HPLC methods)；Finally neutrality is washed till with methanol, after suction filtration, be dried in vacuo for 24 hours at being 50 DEG C in temperature, obtain rod method The molecularly imprinted polymer DMIP-F of mould toxin.
Embodiment 4
The preparation of molecularly imprinted polymer DMIP-6
It weighs virtual template molecular compound DSM-5 0.5mmol (145mg) to be put into 150mL round-bottomed flasks, uses 50mL Acetonitrile/toluene=3:1 (v/v) dissolves, and after adding 2mmol function monomers methacrylic acid (MAA, 172.2mg), is stirred at room temperature 1h；Continue that dimethacrylate ethanedioic acid ester 1.98g is added in the round-bottomed flask, azodiisobutyronitrile is then added (AIBN) 72mg, mixture ultrasound degassing 10min, then be placed on 0~4 DEG C of ice-water bath and lead to nitrogen bubbling deoxygenation 10min, sealing Afterwards, then under 60 DEG C of reaction temperature it is stirred to react for 24 hours；Reaction stop after, then rotating speed be 10000rpm under centrifugation 15~ 20min collects to obtain the particle of cross-linked polymer；With methanol/acetic acid=9:The mixed solvent of 1 (v/v) extracts template molecule, Virtual template molecular compound under room temperature in particles of the 20~40min of supersound washing to extract the cross-linked polymer repeats The supersound washing (HPLC methods) until supernatant can't detect virtual template molecular compound；In being finally washed till with methanol Property, it is dried in vacuo 20~28h after suction filtration, at being 45~50 DEG C in temperature, obtains the molecular engram polymerization of the mould toxin of rod method Object DMIP-6.
Embodiment 5
Non- imprinted polymer DNIP-1 synthesis
DNIP-1 is synthesized in addition to being not added with virtual template molecular compound as template molecule, remaining step and embodiment 3 Preparation method is identical.
Balance Binding experiment
It is acetonitrile to take in conjunction with solvent, adds a concentration of 25 μ g/mL rod methods phenol (AOH) of 1mL, then adds quality as 25mg points Sub- imprinted polymer, i.e. AOH pitch-based spheres are 1 μ g/mg, molecularly imprinted polymer concentration 25mg/mL；20 DEG C, 50rpm is incubated For 24 hours, it centrifuges, takes supernatant to measure and remain AOH concentration levels in supernatant, calculate molecularly imprinted polymer and polymerize with molecular engram The binding performance of object.
1 molecularly imprinted polymer of table balances Binding experiment result with rod method phenol (AOH)
The binding characteristic of DNIP-1 and object rod method phenol (AOH) are relatively low as shown in Table 1, and DMIP-F, DMIP-6 are equal It is demonstrated by the binding characteristic preferably with object rod method phenol (AOH), to show DMIP-F, DMIP-6 separation and concentration chain lattice The nano material of spore phenol (AOH) is used to analyze the potential value of AOH contents in complicated background.

Claims (7)

1. the virtual template molecular compound of the mould toxin of rod method, which is characterized in that the change of the virtual template molecular compound Learn general structure (III)：
Wherein R1It is less than or equal to 4 alkyl for-H or carbon atom；R2For halogen atom ,-NH2, or-CH3；R3For halogen atom ,- NH2, or-CH3。
2. the virtual template molecular compound of the mould toxin of rod method according to claim 1, which is characterized in that the R2For Halogen atom；R3For halogen atom.
3. the virtual template molecular compound of the mould toxin of rod method according to claim 1, which is characterized in that the R2For - F in halogen atom；R3For-the F in halogen atom.
4. the preparation method of the virtual template molecular compound of the mould toxin of rod method according to claim 1, feature exist In including the following steps：Chemical compounds I and compound ii are in NaOH and CuSO4Under the conditions of, by being esterified and replacing cyclization, prepare Obtain virtual template molecular compound III；Its chemical equation is as follows：
。
5. the molecularly imprinted polymer of the mould toxin of rod method, which is characterized in that the molecular engram of the mould toxin of rod method polymerize Object is made as follows：
(1) monomer-template molecule compound is prepared：Weigh the one such virtual template of any one of Claim 1-3 point Sub- compound is template, is put into round-bottomed flask, is (2~5) with volume ratio:1 acetonitrile/toluene dissolves for solvent, adds Function monomer methacrylic acid, stirs 1h at room temperature, and monomer-template molecule compound is made；
(2) cross-linked polymer is prepared：Continue that dimethacrylate ethanedioic acid ester is added in the round-bottomed flask, is then added even Nitrogen bis-isobutyronitrile, mixture ultrasound 8~15min of degassing, then be placed on 0~4 DEG C of ice-water bath and lead to nitrogen bubbling 5~20min of deoxygenation, After sealing, then be stirred to react under 50~80 DEG C of reaction temperature for 24 hours, after reaction stops, then rotating speed be 8000~ 15~20min is centrifuged under 10000rpm, collection obtains the particle of cross-linked polymer；
(3) it demoulds：Using the volume ratio (6~9) of methanol/acetic acid:1 mixed solvent, supersound washing at normal temperatures 20~ 40min, the virtual template molecular compound in particle to extract the cross-linked polymer repeat the supersound washing until upper Until clear liquid can't detect virtual template molecular compound；
(4) dry：The extremely neutral of demoulding post-crosslinking polymer finally is washed with methanol, after suction filtration, in the case where temperature is 45~50 DEG C It is dried in vacuo 20~28h, obtains the molecularly imprinted polymer of the mould toxin of rod method.
6. the molecularly imprinted polymer of the mould toxin of rod method according to claim 5, which is characterized in that the virtual template Molecular compound and the ratio of the amount of the substance of function monomer methacrylic acid are 1:(2~100), the methacrylic acid and diformazan The ratio of the amount of the substance of base acrylic acid ethanedioic acid ester is 1~(1:1000), the dimethacrylate ethanedioic acid ester and azo two The ratio of the amount of the substance of isobutyronitrile is 40:(0.5~1.5).
7. the molecularly imprinted polymer of the mould toxin of rod method according to claim 6, which is characterized in that the virtual template Molecular compound and the ratio of the amount of the substance of function monomer methacrylic acid are 1:(5~80), the methacrylic acid and diformazan The ratio of the amount of the substance of base acrylic acid ethanedioic acid ester is 1:(200~600), the dimethacrylate ethanedioic acid ester and azo two The ratio of the amount of the substance of isobutyronitrile is 40:(0.8~1.2).
CN201810420088.0A 2018-05-04 2018-05-04 The virtual template molecular compound of the mould toxin of rod method and the molecularly imprinted polymer prepared using the compound Pending CN108675981A (en)

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Cited By (2)

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CN109627381A (en) * 2018-12-20 2019-04-16 成都医学院 A kind of virtual template is in the preparation method for preparing application and tentoxin molecularly imprinted polymer in tentoxin molecularly imprinted polymer
CN109627381B (en) * 2018-12-20 2020-09-25 成都医学院 Application of virtual template in preparation of tenuton molecularly imprinted polymer and preparation method of tenuton molecularly imprinted polymer

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