CN107413317B - Chitosan modified GMA/MAA polymer adsorbent and method and application thereof - Google Patents
Chitosan modified GMA/MAA polymer adsorbent and method and application thereof Download PDFInfo
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- 239000003463 adsorbent Substances 0.000 title claims abstract description 46
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 45
- 229920000642 polymer Polymers 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 52
- ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229960002422 lomefloxacin Drugs 0.000 claims abstract description 27
- 239000006228 supernatant Substances 0.000 claims abstract description 21
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 21
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims abstract description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000012153 distilled water Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 8
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 7
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 229960000583 acetic acid Drugs 0.000 claims abstract description 5
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 238000002835 absorbance Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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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
- 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
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
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- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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- 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
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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Abstract
The invention relates to a chitosan modified GMA/MAA polymer adsorbent and a method and application thereof, wherein the method comprises the following steps: (1) GMA/MAA polymeric adsorbent: mixing methacrylic acid and glycidyl methacrylate with ethylene glycol dimethacrylate, dodecanol, cyclohexanol and azobisisobutyronitrile in a volume ratio of 4:14-15, ultrasonically mixing, reacting a polymerization solution at 50-60 ℃, washing with methanol, and drying to obtain a GMA/MAA polymer adsorbent; (2) chitosan modified GMA/MAA polymeric adsorbent: adding GMA/MAA polymer adsorbent, glacial acetic acid and chitosan into distilled water, performing ultrasonic treatment, reacting at 60-70 ℃, adding methanol for washing after the reaction is finished, centrifuging, removing supernatant, and drying to obtain the chitosan modified GMA/MAA polymer adsorbent. The prepared chitosan modified poly GMA/MAA can be used for detecting lomefloxacin by solid-phase extraction.
Description
Technical Field
The invention belongs to the technical field of polymer microspheres, and particularly relates to a chitosan modified GMA/MAA polymer adsorbent and a method and application thereof.
Background
Solid Phase Extraction (SPE) is a sample pretreatment technology developed in the eighties of the last century. SPE uses solid adsorbent to adsorb target compound in liquid sample, separates from sample matrix and interfering compound, and then uses eluent to elute, thus achieving the purpose of separating target compound. The method has the advantages of simplicity, rapidness, simplification of the operation steps of sample pretreatment and shortening of the pretreatment time; and different types of adsorbents and organic solvents can be selected to treat a variety of different types of organic contaminants. In addition, SPE is easy to be used with other instruments, and has been widely used to realize the advantages of automatic on-line analysis, etc.
Chitosan is a natural cationic high molecular polysaccharide, has rich sources, no toxicity, no pollution, good biocompatibility and strong degradability, and is widely applied to various fields of food, environmental protection and the like. Because of the free amino group in the molecule, the high molecular polymer with cationic charge can form a complex with the anionic high molecular polymer under the acidic condition. Amino and hydroxyl in chitosan molecules have lone pair electrons and empty orbitals, so that the chitosan has good adsorption capacity. In addition, cations formed by protonation of amino groups can be electrostatically bound with anions, so that the chitosan can adsorb and bind a plurality of inorganic acids, acidic compounds and organic acids, and can even adsorb and bind amphoteric compounds. The chitosan has the characteristics of hydrophilicity, biocompatibility, degradability and the like, and in addition, free amino and hydroxyl exist on molecular chains of the chitosan and derivatives thereof, so that the chitosan can be used for adsorbing and detecting substances such as metal ions, organic small molecules and the like in food and human tissue fluid, and has wide application prospect.
Disclosure of Invention
The invention mainly provides a chitosan modified GMA/MAA polymer adsorbent, and a method and application thereof. The technical scheme is as follows:
a method for modifying GMA/MAA polymer adsorbent by chitosan comprises the following steps:
(1) preparation of GMA/MAA polymeric adsorbent
Mixing methacrylic acid and glycidyl methacrylate with ethylene glycol dimethacrylate, dodecanol, cyclohexanol and azobisisobutyronitrile in a volume ratio of 4:14-15, ultrasonically mixing, reacting a polymerization solution at 50-60 ℃, washing with methanol, and drying to obtain a GMA/MAA polymer adsorbent;
(2) chitosan modified GMA/MAA polymer adsorbent
Adding GMA/MAA polymer adsorbent, glacial acetic acid and chitosan into distilled water, performing ultrasonic treatment, reacting at 60-70 ℃, adding methanol for washing after the reaction is finished, centrifuging, removing supernatant, and drying to obtain the chitosan modified GMA/MAA polymer adsorbent.
Preferably, the volume ratio of ethylene glycol dimethacrylate to methacrylic acid is 3-3.2:1, the volume ratio of dodecanol to methacrylic acid is 2.9-3.2:1, and the volume ratio of cyclohexanol to methacrylic acid is 24-26: 1.
A chitosan modified GMA/MAA polymer adsorbent is prepared by the method.
The prepared chitosan modified GMA/MAA polymer adsorbent can be used for extracting lomefloxacin.
A method for extracting and detecting lomefloxacin by using a chitosan modified GMA/MAA polymer adsorbent comprises the following steps:
(1) weighing chitosan modified GMA/MAA polymer adsorbent in a container, adding methanol for ultrasonic treatment, and centrifuging to remove supernatant;
(2) adding a lomefloxacin solution to be detected into a container, carrying out ultrasonic treatment, and then centrifuging to remove a supernatant;
(3) adding distilled water into the container, carrying out ultrasonic treatment, and then centrifuging to remove supernatant;
(4) an aqueous methanol solution was added to the vessel, sonicated, centrifuged to take the supernatant and the absorbance measured at a wavelength of 276 nm.
Preferably, the volume content of methanol in the methanol aqueous solution is 20%.
Preferably, before detecting the absorbance of the solution to be detected, different standard concentrations of lomefloxacin are prepared, a standard curve of the concentration of lomefloxacin and the absorbance is established, and the corresponding concentration is found on the standard curve according to the absorbance of the solution to be detected.
By adopting the scheme, the invention has the following advantages:
the chitosan has the characteristics of hydrophilicity, biocompatibility, degradability and the like, in addition, free amino and hydroxyl exist on the molecular chain of the chitosan and the derivatives thereof, so that the chitosan and the derivatives thereof can be used for adsorbing and detecting substances such as metal ions, organic micromolecules and the like in food and human tissue fluid, the chitosan modified poly-GMA/MAA is used for detecting lomefloxacin through solid-phase extraction, the solid-phase extraction method is used as a pretreatment method, and the content of the lomefloxacin is measured at the wavelength of 276 nm. The method has simple preparation process and simple operation. In addition, the surface of the composite material contains characteristic groups beneficial to the adsorption of lomefloxacin, so that the enrichment capacity of a target object can be improved.
Drawings
FIG. 1 is a scanning electron micrograph of GMA/MAA polymeric adsorbent;
FIG. 2 is an infrared spectrum of a GMA/MAA polymeric adsorbent wherein: (a) chitosan modified GMA/MAA polymer adsorbent; (b) poly GMA/MAA polymers;
FIG. 3 is a lomefloxacin UV spectrum;
FIG. 4 is a graph of lomefloxacin concentration versus absorbance standard;
Detailed Description
The experimental methods in the following examples are conventional methods unless otherwise specified, and the experimental reagents and materials involved are conventional biochemical reagents and materials unless otherwise specified.
Example 1
Preparation of GMA/MAA polymer adsorbent
The preparation steps of the GMA/MAA polymer adsorbent are as follows: putting 40 mu L of methacrylic acid (MAA), 145 mu L of Glycidyl Methacrylate (GMA), 125 mu L of ethylene glycol dimethacrylate, 123 mu L of dodecanol, 1mL of cyclohexanol and 0.004g of azobisisobutyronitrile into a centrifuge tube, and carrying out ultrasonic treatment for 30min to uniformly mix. The polymerization solution was then left to react at 55 ℃ for 24 hours. After the reaction, the reaction mixture was washed with methanol to remove unreacted monomers and the crosslinking agent. And finally, drying the compound for later use.
The scanning image of the prepared GMA/MAA polymer adsorbent under an electron microscope is shown in figure 1, and the infrared spectrogram is shown in figure 2, wherein the poly GMA/MAA polymer is shown as b, and the chitosan modified GMA/MAA polymer adsorbent is shown as a.
Preparation of chitosan modified GMA/MAA polymer
Taking a certain amount of polyGMA/MAA polymer, adding 1mL of distilled water, 10 mu L of glacial acetic acid and 0.01g of chitosan, carrying out ultrasonic treatment for 60min, and reacting for 4h at 65 ℃; after the reaction is finished, adding methanol for repeated washing and centrifugation, removing supernatant, and drying at 55 ℃ for later use.
Extraction and detection of lomefloxacin
(1) A lomefloxacin ultraviolet spectrogram is shown in fig. 3, different standard concentrations of lomefloxacin are prepared, and a standard curve of the concentration of lomefloxacin and the absorbance is established, as shown in fig. 4;
(2) weighing 0.02g of chitosan modified GMA/MAA polymer adsorbent, putting into a centrifuge tube, adding 1mL of methanol, performing ultrasonic treatment for 3min, and centrifuging to remove supernatant;
(3) adding a lomefloxacin solution to be detected into a container, carrying out ultrasonic treatment for 20min, and centrifuging to remove a supernatant;
(4) adding 1mL of distilled water into the container, performing ultrasonic treatment for 3min, and centrifuging to remove supernatant;
(5) adding 20% methanol water solution, performing ultrasonic treatment for 10min, centrifuging to obtain supernatant, and measuring absorbance at 276 nm.
Example 2
Preparation of GMA/MAA polymer adsorbent
The preparation steps of the GMA/MAA polymer adsorbent are as follows: putting 40 mu L of methacrylic acid (MAA), 150 mu L of Glycidyl Methacrylate (GMA), 128 mu L of ethylene glycol dimethacrylate, 128 mu L of dodecanol, 1mL of cyclohexanol and 0.004g of azobisisobutyronitrile into a centrifuge tube, and carrying out ultrasonic treatment for 30min to uniformly mix. The polymerization solution was then left to react at 60 ℃ for 24 hours. After the reaction, the reaction mixture was washed with methanol to remove unreacted monomers and the crosslinking agent. And finally, drying the compound for later use.
Preparation of chitosan modified GMA/MAA polymer
Taking a certain amount of polyGMA/MAA polymer, adding 1mL of distilled water, 10 mu L of glacial acetic acid and 0.01g of chitosan, carrying out ultrasonic treatment for 60min, and reacting for 4h at 70 ℃; after the reaction is finished, adding methanol for repeated washing and centrifugation, removing supernatant, and drying at 55 ℃ for later use.
Extraction and detection of lomefloxacin
(1) Preparing different standard concentrations of lomefloxacin, and establishing a standard curve of the concentration of the lomefloxacin and the absorbance;
(2) weighing 0.02g of chitosan modified GMA/MAA polymer adsorbent, putting into a centrifuge tube, adding 1mL of methanol, performing ultrasonic treatment for 3min, and centrifuging to remove supernatant;
(3) adding a lomefloxacin solution to be detected into a container, carrying out ultrasonic treatment for 20min, and centrifuging to remove a supernatant;
(4) adding 1mL of distilled water into the container, performing ultrasonic treatment for 3min, and centrifuging to remove supernatant;
(5) adding 20% methanol water solution, performing ultrasonic treatment for 10min, centrifuging to obtain supernatant, and measuring absorbance at 276 nm.
Various other modifications and changes may be made by those skilled in the art based on the above-described technical solutions and concepts, and all such modifications and changes should fall within the scope of the claims of the present invention.
Claims (7)
1. A preparation method of a chitosan modified GMA/MAA polymer adsorbent is characterized by comprising the following steps: the method comprises the following steps:
(1) preparation of GMA/MAA polymeric adsorbent
Mixing methacrylic acid (MAA) and Glycidyl Methacrylate (GMA) with ethylene glycol dimethacrylate, dodecanol, cyclohexanol and azobisisobutyronitrile in a volume ratio of 4:14-15, ultrasonically mixing, reacting the polymerization solution at 50-60 ℃, washing with methanol, and drying to obtain a GMA/MAA polymer adsorbent;
(2) chitosan modified GMA/MAA polymer adsorbent
Adding GMA/MAA polymer adsorbent, glacial acetic acid and chitosan into distilled water, performing ultrasonic treatment, reacting at 60-70 ℃, adding methanol for washing after the reaction is finished, centrifuging, removing supernatant, and drying to obtain the chitosan modified GMA/MAA polymer adsorbent.
2. The method of preparing a chitosan-modified GMA/MAA polymeric adsorbent as claimed in claim 1, wherein: the volume ratio of ethylene glycol dimethacrylate to methacrylic acid is 3-3.2:1, the volume ratio of dodecanol to methacrylic acid is 2.9-3.2:1, and the volume ratio of cyclohexanol to methacrylic acid is 24-26: 1.
3. A chitosan-modified GMA/MAA polymer adsorbent prepared by the method of claim 1.
4. Use of the chitosan modified GMA/MAA polymeric adsorbent of claim 3 for the extraction of lomefloxacin.
5. A method for detecting lomefloxacin by extraction with chitosan modified GMA/MAA polymeric adsorbent as claimed in claim 3, wherein: the method comprises the following steps:
(1) weighing chitosan modified GMA/MAA polymer adsorbent in a container, adding methanol for ultrasonic treatment, and centrifuging to remove supernatant;
(2) adding a lomefloxacin solution to be detected into a container, carrying out ultrasonic treatment, and then centrifuging to remove a supernatant;
(3) adding distilled water into the container, carrying out ultrasonic treatment, and then centrifuging to remove supernatant;
(4) an aqueous methanol solution was added to the vessel, sonicated, centrifuged to take the supernatant and the absorbance measured at a wavelength of 276 nm.
6. The method for extracting and detecting lomefloxacin according to the chitosan modified GMA/MAA polymer adsorbent of claim 5, wherein: the volume content of methanol in the methanol water solution is 20%.
7. The method for extracting and detecting lomefloxacin according to the chitosan modified GMA/MAA polymer adsorbent of claim 5, wherein: before detecting the absorbance of the solution to be detected, different standard concentrations of lomefloxacin are prepared, a standard curve of the concentration of the lomefloxacin and the absorbance is established, and the corresponding concentration is found on the standard curve according to the absorbance of the solution to be detected.
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| CN103374143A (en) * | 2012-04-28 | 2013-10-30 | 中国科学院过程工程研究所 | Super macroporous polymer microspheres and preparation method thereof |
| CN103599759A (en) * | 2013-10-29 | 2014-02-26 | 江苏大学 | Preparation method of novel adsorbent for selectively separating ciprofloxacin in water environment |
| CN103949227A (en) * | 2014-05-09 | 2014-07-30 | 河北大学 | Preparation method of hybrid composite solid-phase extraction adsorbent with hydrophilic outer surface |
| CN104587970A (en) * | 2014-11-24 | 2015-05-06 | 江苏大学 | Magnetic chitosan composite microsphere surface imprinted adsorbent and preparation method thereof |
| CN106422415A (en) * | 2016-09-12 | 2017-02-22 | 福州大学 | Mucopolysaccharide functionalized hydrophilic solid-phase microextraction monolithic column |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101992068A (en) * | 2009-08-09 | 2011-03-30 | 中国科学院兰州化学物理研究所 | Nitrogen and phosphorus absorbing agent |
| CN103374143A (en) * | 2012-04-28 | 2013-10-30 | 中国科学院过程工程研究所 | Super macroporous polymer microspheres and preparation method thereof |
| CN103599759A (en) * | 2013-10-29 | 2014-02-26 | 江苏大学 | Preparation method of novel adsorbent for selectively separating ciprofloxacin in water environment |
| CN103949227A (en) * | 2014-05-09 | 2014-07-30 | 河北大学 | Preparation method of hybrid composite solid-phase extraction adsorbent with hydrophilic outer surface |
| CN104587970A (en) * | 2014-11-24 | 2015-05-06 | 江苏大学 | Magnetic chitosan composite microsphere surface imprinted adsorbent and preparation method thereof |
| CN106422415A (en) * | 2016-09-12 | 2017-02-22 | 福州大学 | Mucopolysaccharide functionalized hydrophilic solid-phase microextraction monolithic column |
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