CN105199045A - Preparation method of molecularly imprinted polymer capable of recognizing sulfonamide antibiotics - Google Patents
Preparation method of molecularly imprinted polymer capable of recognizing sulfonamide antibiotics Download PDFInfo
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- CN105199045A CN105199045A CN201510642230.2A CN201510642230A CN105199045A CN 105199045 A CN105199045 A CN 105199045A CN 201510642230 A CN201510642230 A CN 201510642230A CN 105199045 A CN105199045 A CN 105199045A
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- 229920000344 molecularly imprinted polymer Polymers 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229940123317 Sulfonamide antibiotic Drugs 0.000 title abstract 6
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 25
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims abstract description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 8
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 52
- 229940124530 sulfonamide Drugs 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 229940088710 antibiotic agent Drugs 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 21
- 239000006228 supernatant Substances 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 16
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 238000006392 deoxygenation reaction Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000012456 homogeneous solution Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 4
- 238000001514 detection method Methods 0.000 abstract description 2
- 238000012673 precipitation polymerization Methods 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 230000002950 deficient Effects 0.000 abstract 1
- -1 trimethylol propyl Chemical group 0.000 abstract 1
- 230000000274 adsorptive effect Effects 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 5
- 238000005374 membrane filtration Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229960004306 sulfadiazine Drugs 0.000 description 4
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 4
- GPKMZACUUQFPGH-UHFFFAOYSA-N C=NS(=O)=O Chemical compound C=NS(=O)=O GPKMZACUUQFPGH-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229960002211 sulfapyridine Drugs 0.000 description 3
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 3
- LSBIUXKNVUBKRI-UHFFFAOYSA-N 4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229960002135 sulfadimidine Drugs 0.000 description 2
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010061619 Deformity Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a preparation method of molecularly imprinted polymer capable of recognizing sulfonamide antibiotics, and particularly relates to a preparation method of an antibiotic recognition material with universality. The molecularly imprinted polymer is prepared by adopting a method of precipitation polymerization, taking sulfonamide antibiotics as a template, taking acrylamide and 4-vinylpyridine jointly as a functional monomer and taking trimethylol propyl triacrylate as a crosslinking agent. The sulfonamide antibiotics can be quickly recognized by the molecularly imprinted polymer prepared by the method, status quo that the sulfonamide antibiotics are deficient is solved, and the molecularly imprinted polymer has application potential in quick detection of the sulfonamide antibiotics and sample pretreatment.
Description
Technical field
The invention belongs to pollutant monitoring, separation and purification field, relate to the preparation method of the molecularly imprinted polymer of sulfa antibiotics in a kind of environment-identification.
Background technology
Sulfa antibiotics is a kind of widely used synthesis class microbiotic, has the features such as hydrophilic and stability is strong, very easily enters in water surrounding and fishery products body.The water of mankind's long-term drinking or edible residual sulfa antibiotics or fishery products, will cause body to produce the symptoms such as anaphylaxis, cancer, deformity and resistance.At present, studies have reported that existence high density sulfa antibiotics being detected from fishery products, surface water, sewage work's Inlet and outlet water etc., therefore, be necessary the universality material developing a kind of identifiable design sulfa antibiotics.
At present, molecular imprinting is as a kind of sample pre-treatments means, be widely used in antibiotic purification art, but in the research of sulfa antibiotics, mostly for template molecule with sulfamethoxazole or sulfamethazine, preparation is for the antibiotic specific recognition material of a certain sulfanilamide (SN), not yet there is the universality molecularly imprinted polymer material for sulfa antibiotics identification, therefore, when identifying sulfa antibiotics, different kinds of molecules imprinted material must be prepared for target compound, be unfavorable for setting up easy, the recognition methods of the sulfa antibiotics of universality.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of preparation method identifying the molecularly imprinted polymer of sulfa antibiotics, specifically a kind of preparation method with the microbiotic identification material of universality.Adopt the method for precipitation polymerization, using sulfa antibiotics as template, acrylamide and 4-vinylpyridine are as function monomer, and trimethylolpropane trimethacrylate, as linking agent, prepares molecularly imprinted polymer.
Technical scheme of the present invention comprises template molecule prepolymerization, template molecule is fixed, dry four steps of template molecule elution and product:
(1) template molecule prepolymerization: sulfanilamide (SN) (template molecule), 4-vinylpyridine and acrylamide are dissolved in solvent according to the mol ratio of 1:1:1-1:2:2, form transparent and homogeneous solution after stirring at room temperature; Described solvent is the one in acetonitrile, methyl alcohol, toluene.
(2) template molecule is fixed: according to trimethylolpropane trimethacrylate: sulfanilamide (SN) mol ratio is the ratio of 10:1-20:1, trimethylolpropane trimethacrylate is added in step (1) clear solution, stirring at room temperature is to dissolving, 20-40mg Diisopropyl azodicarboxylate is added again in solution, pass into nitrogen deoxygenation, after sealing, solution is placed in 60 DEG C of-80 DEG C of water-baths and reacts 12-24h;
(3) template molecule elution: by step (2) gained solution centrifugal, collects supernatant liquor and throw out; Ultraviolet spectrophotometer is utilized to test to the absorbancy of sulfanilamide (SN) in supernatant liquor; In the throw out after centrifugal, add elutriant, 100 DEG C of-120 DEG C of stirring and refluxing 30-60min, centrifugal rear collecting precipitation and supernatant liquor respectively, repeat aforesaid operations, until can't detect sulfanilamide (SN) in supernatant liquor, namely in supernatant liquor, the absorbancy of sulfanilamide (SN) is 0; Now collecting precipitation thing, is the product after template removal, and wherein elutriant is methyl alcohol: acetic acid volume ratio is the solution of 9:1.
(4) product is dry: the product that step (3) obtains can be obtained desired molecule imprinted polymer after deionized water wash, drying.
Beneficial effect of the present invention: molecularly imprinted polymer prepared by the present invention adopts the common structural unit sulfanilamide (SN) of sulfa antibiotics as template molecule, therefore this molecularly imprinted polymer all has recognition capability to any one sulfa antibiotics, it is a kind of sulfa antibiotics identification material of universality, namely this molecularly imprinted polymer can identify sulfa antibiotics fast, solve the present situation of sulfa antibiotics identification material shortage, there are the potentiality in field application such as sulfa antibiotics rapid detection, sample pre-treatments.In addition, in preparation process, adopt 4-vinylpyridine and acrylamide as two kinds of function monomers, avoid the feature that simple function monomer reactive force is weak, promote the absorption property of material; Adopt the trimethylolpropane trimethacrylate with three C=C double bonds as linking agent simultaneously, improve the degree of crosslinking of material, thus the mechanical property of strongthener, promote the potentiality that it applies in true environment.
Accompanying drawing explanation
Fig. 1 a is the scanning electron microscope diagram sheet of the embodiment of the present invention 1 molecularly imprinted polymer.
Fig. 1 b is the scanning electron microscope diagram sheet of the embodiment of the present invention 1 molecularly imprinted polymer.
Fig. 2 is the absorption situation of molecularly imprinted polymer to sulfanilamide (SN).
Fig. 3 is the adsorptive capacity of molecularly imprinted polymer to Sulphadiazine Sodium.
Embodiment
Below in conjunction with example, the present invention is described in detail.
First, fixed by template molecule prepolymerization, template molecule, molecularly imprinted polymer that dry four steps synthesis of template molecule elution and product identifies sulfa antibiotics:
Embodiment 1
(1) template molecule prepolymerization: be dissolved in acetonitrile according to the mol ratio of 1:2:2 by sulfanilamide (SN), 4-vinylpyridine and acrylamide, forms transparent and homogeneous solution after stirring at room temperature stirring at room temperature;
(2) template molecule is fixed: according to trimethylolpropane trimethacrylate: sulfanilamide (SN) mol ratio is the ratio of 10:1, trimethylolpropane trimethacrylate is added in step (1) solution, stirring at room temperature is to dissolving, 20mg Diisopropyl azodicarboxylate is added again in solution, pass into nitrogen deoxygenation, after sealing, solution is placed in 60 DEG C of water-baths and reacts 12h;
(3) template molecule elution: collect supernatant liquor and throw out; Ultraviolet spectrophotometer is utilized to test to the absorbancy of sulfanilamide (SN) in supernatant liquor; Elutriant is added in the throw out after centrifugal, 100 DEG C of stirring and refluxing 30min, centrifugal rear collecting precipitation and supernatant liquor respectively, repeat aforesaid operations, until the absorbancy of sulfanilamide (SN) is 0 in supernatant liquor, now collecting precipitation thing, is the product after template removal, and wherein elutriant is methyl alcohol/acetic acid volume ratio is the solution of 9:1.
(4) product is dry: the product that step (3) obtains is obtained desired molecule imprinted polymer after deionized water wash, drying, and molecularly imprinted polymer pattern as shown in Figure 1a.
Embodiment 2
(1) template molecule prepolymerization: be dissolved in toluene according to the mol ratio of 1:1.5:1.5 by sulfanilamide (SN), 4-vinylpyridine and acrylamide, forms transparent and homogeneous solution after stirring at room temperature;
(2) be polymerized: according to trimethylolpropane trimethacrylate: sulfanilamide (SN) mol ratio is the ratio of 15:1, trimethylolpropane trimethacrylate is added in step (1) solution, stirring at room temperature is to dissolving, 30mg Diisopropyl azodicarboxylate is added again in solution, pass into nitrogen deoxygenation, after sealing, solution is placed in 80 DEG C of water-baths and reacts 12h;
(3) template molecule elution: solution centrifugal step (2) obtained, collects supernatant liquor and throw out; Ultraviolet spectrophotometer is utilized to test to the absorbancy of sulfanilamide (SN) in supernatant liquor; Elutriant is added in the throw out after centrifugal, 100 DEG C of stirring and refluxing 60min, centrifugal rear collecting precipitation and supernatant liquor respectively, repeat aforesaid operations, until can't detect the antibiotic existence of sulfanilamide (SN) in supernatant liquor, now collecting precipitation thing, is the product after template removal, and wherein elutriant is methyl alcohol/acetic acid volume ratio is the solution of 9:1.
(4) product is dry: the product that step (3) obtains is obtained desired molecule imprinted polymer after deionized water wash, drying, and molecularly imprinted polymer pattern as shown in Figure 1 b.
Embodiment 3
(1) template molecule prepolymerization: sulfanilamide (SN) (template molecule), 4-vinylpyridine and acrylamide are dissolved in methyl alcohol according to the mol ratio of 1:1:1, form transparent and homogeneous solution after stirring at room temperature;
(2) template molecule is fixed: according to trimethylolpropane trimethacrylate: sulfanilamide (SN) mol ratio is the ratio of 20:1, trimethylolpropane trimethacrylate is added in step (1) solution, stirring at room temperature is to dissolving, 40mg Diisopropyl azodicarboxylate is added again in solution, pass into nitrogen deoxygenation, after sealing, solution is placed in 70 DEG C of water-baths and reacts 24h;
(3) template molecule elution: solution centrifugal step (2) obtained, collects supernatant liquor and throw out; Ultraviolet spectrophotometer is utilized to test to the absorbancy of sulfanilamide (SN) in supernatant liquor; Elutriant is added in the throw out after centrifugal, 120 DEG C of stirring and refluxing 30min, centrifugal rear collecting precipitation and supernatant liquor respectively, repeat aforesaid operations, until the absorbancy of sulfanilamide (SN) is 0 in supernatant liquor, now collecting precipitation thing, is the product after template removal, and wherein elutriant is methyl alcohol/acetic acid volume ratio is the solution of 9:1.
(4) product is dry: can obtain desired molecule imprinted polymer after product deionized water wash step (3) obtained, drying.
Molecularly imprinted polymer synthesized by following discriminating is to the recognition capability of sulfa antibiotics.
Embodiment 4
1. molecularly imprinted polymer is to the recognition capability of sulfanilamide (SN)
Accurately take 10mg molecularly imprinted polymer, be added in 200mL sulfanilamide (SN) solution (10mg/L), 150rpm, 30 DEG C of cultivations, timing sampling, uses 0.22um membrane filtration, measures filtrate absorbancy, the time of equilibrium adsorption of molecularly imprinted polymer is calculated according to typical curve, and maximal absorptive capacity.Absorption result as shown in Figure 2.Adopt the obtained molecularly imprinted polymer 60min of method of the present invention to reach adsorption equilibrium, maximal absorptive capacity is up to 180mg/g.
2. molecularly imprinted polymer is to the recognition capability of sulfapyridine
Accurately take 10mg molecularly imprinted polymer, be added in 200mL sulfapyridine solution (10mg/L), 150rpm, 30 DEG C of cultivations, timing sampling, uses 0.22um membrane filtration, measure filtrate absorbancy, calculate molecularly imprinted polymer to the adsorptive capacity of sulfapyridine according to typical curve, as shown in Figure 3, adsorptive capacity is 44mg/g to data.
3. molecularly imprinted polymer is to the recognition capability of Sulphadiazine Sodium
Accurately take 10mg molecularly imprinted polymer, be added in 200mL Sulphadiazine Sodium solution (10mg/L), 150rpm, 30 DEG C of cultivations, timing sampling, uses 0.22um membrane filtration, measure filtrate absorbancy, calculate molecularly imprinted polymer to the adsorptive capacity of Sulphadiazine Sodium according to typical curve, as shown in Figure 3, adsorptive capacity is 45mg/g to data.
4. molecularly imprinted polymer is to the recognition capability of sulfamethazine
Accurately take 10mg molecularly imprinted polymer, be added in 200mL dimethyl pyrimidine solution (10mg/L), 150rpm, 30 DEG C of cultivations, timing sampling, uses 0.22um membrane filtration, measure filtrate absorbancy, calculate molecularly imprinted polymer to the adsorptive capacity of dimethyl pyrimidine according to typical curve, as shown in Figure 3, adsorptive capacity is 48mg/g to data.
5. molecularly imprinted polymer is to the recognition capability of methylene sulfonamide (different) oxazole
Accurately take 10mg molecularly imprinted polymer, be added in 200mL methylene sulfonamide (different) oxazole solution (10mg/L), 150rpm, 30 DEG C of cultivations, timing sampling, uses 0.22um membrane filtration, measure filtrate absorbancy, calculate molecularly imprinted polymer to the adsorptive capacity of methylene sulfonamide (different) oxazole according to typical curve, as shown in Figure 3, adsorptive capacity is 80mg/g to data.
Claims (4)
1. identify a preparation method for the molecularly imprinted polymer of sulfa antibiotics, it is characterized in that, comprise template molecule prepolymerization, template molecule is fixed, dry four steps of template molecule elution and product:
(1) template molecule prepolymerization: be dissolved in solvent by the mol ratio of 1:1:1-1:2:2 by sulfanilamide (SN), 4-vinylpyridine and acrylamide, forms transparent and homogeneous solution after stirring at room temperature;
(2) template molecule is fixed: according to trimethylolpropane trimethacrylate: sulfanilamide (SN) mol ratio is the ratio of 10:1-20:1, trimethylolpropane trimethacrylate is added in step (1) clear solution, stirring at room temperature is to dissolving, 20-40mg Diisopropyl azodicarboxylate is added again in solution, pass into nitrogen deoxygenation, in 60-80 DEG C of water-bath, react 12-24h;
(3) template molecule elution: by step (2) gained solution centrifugal, collects supernatant liquor and throw out; Ultraviolet spectrophotometer is utilized to test to the absorbancy of sulfanilamide (SN) in supernatant liquor; In the throw out after centrifugal, add elutriant, 100-120 DEG C of stirring and refluxing 30-60min, centrifugal collecting precipitation and supernatant liquor, repeat aforesaid operations, until sulfanilamide (SN) absorbancy is 0 in supernatant liquor; Now collecting precipitation thing, throw out is the product after template removal;
(4) product is dry: the product that step (3) obtains is obtained molecularly imprinted polymer after deionized water wash, drying.
2. a kind of preparation method identifying the molecularly imprinted polymer of sulfa antibiotics as claimed in claim 1, is characterized in that, step (1) described solvent is acetonitrile, methyl alcohol or toluene.
3. a kind of preparation method identifying the molecularly imprinted polymer of sulfa antibiotics as claimed in claim 2, is characterized in that, step (3) described elutriant is methyl alcohol: acetic acid volume ratio is the solution of 9:1.
4. a kind of preparation method identifying the molecularly imprinted polymer of sulfa antibiotics as claimed in claim 1 or 2, is characterized in that, step (3) described elutriant is methyl alcohol: acetic acid volume ratio is the solution of 9:1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110426383A (en) * | 2019-08-09 | 2019-11-08 | 国家城市供水水质监测网太原监测站 | The detection method of antibiotic in a kind of water body |
| CN112090411A (en) * | 2020-08-06 | 2020-12-18 | 河南科技学院 | Magnetic material for analyzing sulfonamide antibiotics and detection method of sulfonamide antibiotics |
| CN115197463A (en) * | 2022-07-11 | 2022-10-18 | 大连大学 | Preparation method and application of sulfadiazine molecularly imprinted one-dimensional photonic crystal sensor film |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110426383A (en) * | 2019-08-09 | 2019-11-08 | 国家城市供水水质监测网太原监测站 | The detection method of antibiotic in a kind of water body |
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| CN115197463B (en) * | 2022-07-11 | 2023-09-29 | 大连大学 | Preparation method and application of sulfadiazine molecularly imprinted one-dimensional photonic crystal sensor film |
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