CN105693959B - The preparation method of magnetic molecularly imprinted polymer with hydrogen bond array - Google Patents
The preparation method of magnetic molecularly imprinted polymer with hydrogen bond array Download PDFInfo
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- CN105693959B CN105693959B CN201610064335.9A CN201610064335A CN105693959B CN 105693959 B CN105693959 B CN 105693959B CN 201610064335 A CN201610064335 A CN 201610064335A CN 105693959 B CN105693959 B CN 105693959B
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- magnetic
- imprinted polymer
- molecularly imprinted
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- 229920000344 molecularly imprinted polymer Polymers 0.000 title claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 24
- 239000001257 hydrogen Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical group CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000004005 microsphere Substances 0.000 claims abstract description 33
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims abstract description 30
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical group CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229960000611 pyrimethamine Drugs 0.000 claims abstract description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 229940098184 amytal Drugs 0.000 claims abstract description 20
- 238000012986 modification Methods 0.000 claims abstract description 17
- 239000002122 magnetic nanoparticle Substances 0.000 claims abstract description 15
- 230000004048 modification Effects 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 230000000694 effects Effects 0.000 claims abstract description 9
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 229910052681 coesite Inorganic materials 0.000 claims description 18
- 229910052906 cristobalite Inorganic materials 0.000 claims description 18
- 229910052682 stishovite Inorganic materials 0.000 claims description 18
- 229910052905 tridymite Inorganic materials 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 3
- 229940125717 barbiturate Drugs 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- -1 methacryloxy Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 abstract description 5
- 230000009878 intermolecular interaction Effects 0.000 abstract description 3
- 239000011159 matrix material Substances 0.000 abstract description 3
- 238000001338 self-assembly Methods 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 15
- 238000005516 engineering process Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005389 magnetism Effects 0.000 description 4
- 201000004792 malaria Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000224016 Plasmodium Species 0.000 description 2
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000011553 magnetic fluid Substances 0.000 description 2
- 230000005415 magnetization Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 108700007696 Tetrahydrofolate Dehydrogenase Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 102000004419 dihydrofolate reductase Human genes 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- JKGITWJSGDFJKO-UHFFFAOYSA-N ethoxy(trihydroxy)silane Chemical class CCO[Si](O)(O)O JKGITWJSGDFJKO-UHFFFAOYSA-N 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002607 hemopoietic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000000505 pernicious effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28009—Magnetic properties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/46—Materials comprising a mixture of inorganic and organic materials
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- C—CHEMISTRY; METALLURGY
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/042—Elimination of an organic solid phase
- C08J2201/0424—Elimination of an organic solid phase containing halogen, nitrogen, sulphur or phosphorus atoms
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/10—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to inorganic materials
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- Polymers & Plastics (AREA)
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Abstract
The invention discloses a kind of preparation method of the magnetic molecularly imprinted polymer with hydrogen bond array, include the following steps：Synthesize Fe3O4Magnetic nanoparticle；Sol-gal process prepares the magnetic Nano microsphere of coated silica；Prepare the magnetic Nano microsphere of MPS modifications；Template molecule is with after function monomer self assembly, adding magnetic Nano microsphere, crosslinking agent, initiator and the decentralized medium of MPS modifications, uniform stirring polymerisation；After reaction, Magneto separate product, removes dry, obtained magnetic microsphere molecular imprinted polymer on surface after template molecule；The template molecule is pyrimethamine, and the function monomer is amytal.The present invention is formed intermolecular interaction matrix, increases the binding site of the two, improved affinity and Selective adsorption of the magnetic molecularly imprinted polymer to pyrimethamine using the multiple hydrogen bonding effect between amytal and pyrimethamine.
Description
Technical field
The present invention relates to molecular imprinting field, more particularly to a kind of magnetic molecularly imprinted polymerization with hydrogen bond array
The preparation method of thing.
Background technology
Pyrimethamine (PYR) is anti-malaria medicine at present extensively, is mainly used for the prevention of malaria, can inhibit dihydro in polypide
The activity of folic acid reductase, thus the folic acid eubolism of plasmodium is disturbed, before pernicious malaria and Plasmodium vivax red blood cell
Phase is effective, is commonly used for causal prophylactics.Also development of the plasmodium in mosquito body can be suppressed, therefore can blocking propagation.Clinically use
Treated in prevention of malaria and stand-down anti-recurrence.It is except AIDS and lung knot every year because of malaria 500,000,000 clinical cases of dead estimation
One of disease of most people is murdered outside core communicable disease, has caused the attention of International Health Organization.
Pyrimethamine has a wide range of applications in animal product and aquatic products body, and appropriate use can strengthen the disease-resistant of animal
Ability.But pyrimethamine has the savings of height in animal product body, beyond a certain range, people destroys people's after eating
Hemopoietic system, causes haemolytical anaemia, or even has and cause potential carcinogenic possibility, while Central nervous system has directly
Toxic action.Therefore, effective pyrimethamine detecting method is established to have very important significance.
In the prior art mainly using the medicine in high performance liquid chromatography (HPLC) analysis biological sample.HPLC is generally used
C18 columns, go to toward the preceding processing for being related to complexity being injected into chromatographic column, for example are dropped by acid adding or organic solvent deposit
Solution, and liquid-liquid extraction and offline Solid Phase Extraction.But these processes are complicated and time-consuming, medicine may also be in sample pre-treatments
Stage yield-loss, so in such cases, it is necessary to produce a kind of to the selective material of target molecule.Molecular imprinting technology is
A kind of technology of preparing that molecular recognition site is introduced to polymeric material.It is (i.e. common that molecular imprinting technology is divided into the pre-assembled process of molecule
Valence link combination) and molecular self-assembling process (i.e. non-covalently bonded shares).
Since Hyarogen-bonding is weaker, only interacted in general molecular imprinting technology with 1-2 hydrogen bond, to target
The limited sorption capacity of thing.Thus the binding site of template molecule and function monomer is less, weaker to the selectivity of template molecule,
Effective selection absorption cannot be realized to template molecule.
The content of the invention
It is an object of the invention to overcome shortcoming and defect of the prior art, there is provided a kind of magnetism with hydrogen bond array
The preparation method of molecularly imprinted polymer.
The present invention is achieved by the following technical solutions：A kind of magnetic molecularly imprinted polymer with hydrogen bond array
Preparation method, comprises the following steps：
(1) precipitation method synthesis Fe3O4Magnetic nanoparticle；
(2) sol-gal process prepares the magnetic Nano microsphere Fe of coated silica3O4@SiO2；
(3) with MPS to magnetic Nano microsphere Fe3O4@SiO2Surface modification is carried out, obtains the magnetic Nano microsphere of MPS modifications
Fe3O4@SiO2@MPS；
(4) template molecule, function monomer are sufficiently mixed in DMSO, then add MPS modification magnetic Nano microsphere,
Crosslinking agent, initiator and decentralized medium, bring it about polymerisation, obtain the molecularly imprinted polymer of surface coated die plate molecule
Magnetic microsphere；
(5) magnetic microsphere obtained in washing step (4), it is dry after removing the template molecule wherein coated, obtain magnetism
Microsphere surface molecularly imprinted polymer Fe3O4@SiO2-MIPs；
Wherein, there is multiple hydrogen bonding effect between the template molecule and function monomer.
Relative to the prior art, the preparation method of magnetic molecularly imprinted polymer of the invention, utilizes template molecule and work(
Multiple hydrogen bonding effect between energy monomer, forms intermolecular interaction matrix, increases the binding site of template molecule and function monomer,
So as to strengthen the effect between template molecule and function monomer, magnetic molecularly imprinted polymer is improved to the affine of template molecule
Power and Selective adsorption.
Further, the template molecule is pyrimethamine, and the function monomer is amytal.Using PYR as template point
Son, amytal are acted on using the multiple hydrogen bonding between amytal and PYR as function monomer, form intermolecular work
With matrix, increase the binding site of PYR and amytal, compare so as to strengthen template molecule PYR with function monomer isoamyl bar
Effect between appropriate, improves affinity and Selective adsorption of the magnetic molecularly imprinted polymer to template molecule PYR.
Further, in step (4), the molar ratio of the template molecule and function monomer is 1：1.
Further, in step (4), the crosslinking agent is divinylbenzene, and the initiator is azodiisobutyronitrile, described
Decentralized medium is water.
Further, the preparation method of the amytal is：After barbiturates is dissolved in the water, it is molten to add copper sulphate
Liquid；Allyl bromide, bromoallylene is then injected into, the sodium hydroxide solution that mass fraction is 10% is added dropwise；Stirring reaction 1-3h.
Further, by Fe in step (3)3O4@SiO2It is scattered in deionized water, first is added after adding hydrochloric acid solution stirring
Base acryloxypropyl trimethoxy silane (MPS), is stirred at room temperature 20-28h；Reaction terminates, Magneto separate, with methanol and go from
The repeatedly washing respectively of sub- water, is dried to obtain the magnetic Nano microsphere of MPS modifications.
Further, pyrimethamine and amytal are dissolved in DMSO in step (4), fully shake up mixing, room temperature is put
Put 10-14h；Fe is added thereto3O4@SiO2@MPS, crosslinking agent, initiator and decentralized medium, after uniform stirring 20-40min,
Under nitrogen protective condition, 10-14h is reacted at 60-80 DEG C.
Further, in step (4), the volume ratio of DMSO and decentralized medium is 1:8.
Further, it is 2 with volume ratio in step (5):8 acetic acid and methanol solution surname extraction removes template molecule ethamine
Pyrimidine.
In order to better understand and implement, the invention will now be described in detail with reference to the accompanying drawings.
Brief description of the drawings
Fig. 1 is the preparation process schematic diagram of the magnetic molecularly imprinted polymer of the present invention.
Fig. 2 is the transmission electron microscope photo of the magnetic molecularly imprinted polymer of the present invention.
Fig. 3 is the infrared spectrogram of (a) and (b) after elution before the magnetic molecularly imprinted polymer of the present invention elutes.
Fig. 4 is the Fe of the present invention3O4The thermogravimetric analysis figure of magnetic nanoparticle (a) and magnetic molecularly imprinted polymer (b).
Fig. 5 is the Fe of the present invention3O4Magnetic nanoparticle (a), the magnetic Nano microsphere (b) of MPS modifications and magnetic molecule print
The XRD spectrum of mark polymer (c).
Fig. 6 is magnetic nanoparticle Fe of the present invention3O4(a) and magnetic molecularly imprinted polymer (b) hysteresis curve figure.
Embodiment
The preparation method of the magnetic molecularly imprinted polymer with hydrogen bond array is described in detail in the present embodiment, with
Pyrimethamine is template molecule, exemplified by amytal is function monomer, but does not limit protection scope of the present invention with this.Institute
State template molecule and function monomer is not limited to pyrimethamine and amytal, can also be that other are acted on multiple hydrogen bonding
Template molecule and function monomer.
Referring to Fig. 1, it is the preparation process schematic diagram for the magnetic molecularly imprinted polymer that the present invention has hydrogen bond array.
The preparation method comprises the following steps：
(1)Fe3O4The synthesis of magnetic nanoparticle
Fe is prepared using the precipitation method3O4Magnetic nanoparticle：Weigh 3.975g (0.02mol) frerrous chlorides and 9.4574g
(0.035mol) iron chloride, is dissolved in 40ml distilled water respectively.Pour into there-necked flask, electric stirring.It is passed through nitrogen 30 minutes, protects
Nitrogen atmosphere is held, is heated to 60 DEG C.30ml concentrated ammonia liquors are rapidly joined, are heated to 80 DEG C, when reaction 1 is small.6ml oleic acid is added dropwise, instead
Answer 1 it is small when after be warming up to 90 DEG C, after curing 30 minutes, add 1mol/L hydrochloric acid.Wash precipitation 5 times, 40 DEG C respectively with water and ethanol
Be dried in vacuo 24 it is small when, obtain Fe3O4Magnetic nanoparticle.
(2) magnetic Nano microsphere Fe3O4@SiO2Synthesis
The magnetic Nano microsphere Fe of coated silica is prepared using sol-gal process3O4@SiO2：Weigh a certain amount of Fe3O4
Magnetic nanoparticle, is dissolved in q. s. toluene, is made into the oil-based magnetic fluids of concentration 20mg/mL.100ml magnetic fluids are taken to add there-necked flask
In, and add 40ml water and 160ml isopropanols.3ml concentrated ammonia liquors, electric stirring are then added, and is passed through nitrogen 30 minutes.Dropwise
Add 6ml ethyl orthosilicates (TEOS).React at room temperature 24 it is small when.Magneto separate after reaction, respectively with ethanol, water washing 3 times.
When 60 DEG C of vacuum drying 24 are small, magnetic Nano microsphere Fe is obtained3O4@SiO2。
(3) the magnetic Nano microsphere Fe of MPS modifications3O4@SiO2The synthesis of@MPS
Weigh obtained magnetic Nano microsphere Fe in 200mg steps (2)3O4@SiO2, ultrasonic disperse 20min in 10mL go from
In sub- water.Then the hydrochloric acid solution of the 0.01mol/L of 1mL is added, being vigorously stirred is uniformly mixed it.Then the first of 1mL is added
Base acryloxypropyl trimethoxy silane (MPS), is stirred at room temperature 20-28h.After reaction, Magneto separate, with methanol and goes
Ionized water washs 3 times respectively, and vacuum drying, obtains the magnetic Nano microsphere Fe of MPS modifications3O4@SiO2@MPS。
(4) magnetic molecularly imprinted polymer Fe3O4@SiO2The synthesis of-MIPs
1.0mmol (0.2487g) PYR (template molecule), 1.0mmol (0.208g) amytal (function monomer) is molten
Solution fully shakes up mixing in the DMSO of 10ml, and 10-14h is placed in room temperature dark.200mg is added in aforementioned mixture
The magnetic Nano microsphere Fe being prepared in step (3)3O4@SiO2@MPS, 20mmol (2.88ml) crosslinking agent, 60mg initiators
With the decentralized medium of 80ml, uniform stirring 20-40min.Under nitrogen protective condition, 60-80 DEG C of reaction 10-14h.Reaction is completed
Afterwards, Magneto separate product.It is 2 with volume ratio:8 acetic acid and methanol solution surname extraction, elution remove PYR, obtain grey powder,
Vacuum drying, is prepared magnetic molecularly imprinted polymer Fe3O4@SiO2-MIPs.In the present embodiment, the crosslinking agent is two
Vinyl benzene (DVB), the initiator are azodiisobutyronitrile (AIBN), and the decentralized medium is water.
Wherein amytal prepare it is as follows：It will be dissolved under 0.1mol (12.8g) barbiturates stirring
In the water of 60.0mL.After stirring evenly, the copper-bath that 30mL mass fractions are 5% is added, then disposably injects allyl
Bromide 0.2mol (17.3mL).The sodium hydroxide solution that 80mL mass fractions are 10%, low speed 6d/s are added dropwise into reaction solution
Left and right.After being added dropwise, continue stirring reaction 1-3h.After reaction, filtering and in 60 DEG C of dryings, obtains faint yellow thick production
Product.Activated carbon decolorizing 3h is used in boiling water, is filtered under diminished pressure while hot.It will obtain product to recrystallize at 40 DEG C, be dried to obtain after filtering
The amytal of white.
Referring to Fig. 2, it is the transmission electron microscope photo of the magnetic molecularly imprinted polymer.Can from figure
Go out, the magnetic molecularly imprinted polymer being prepared by surface modification with post-polymerization, wrapped on magnetic Nano microsphere surface
Cover one layer of molecular engram shell.
Referring to Fig. 3, magnetic molecularly imprinted polymer is before surname extraction eluted template molecule, in 3493cm-1,
3348cm-1, 3299cm-1And 1684cm-1There is sharp absworption peak, in 3500~3300cm-1In the range of N-H keys stretching vibration.
And magnetic molecularly imprinted polymer is after elution, these characteristic absorption peaks disappear, and illustrate eluting mould by surname extraction
After plate molecule, the pyrimethamine in magnetic molecularly imprinted polymer has been eluted totally.
Referring to Fig. 4, it is the Fe of the present invention3O4The heat of magnetic nanoparticle (a) and magnetic molecularly imprinted polymer (b)
Weight analysis figure.With Fe3O4Magnetic nanoparticle is different, and magnetic molecularly imprinted polymer has one soon between 290 DEG C and 443 DEG C
The fast weightless stage, and weight-loss ratio is very high, and this is derived from the molecularly imprinted polymer on magnetic microsphere surface, illustrates Fe3O4Magnetic
Property nano grain surface has successfully coated molecularly imprinted polymer.
Referring to Fig. 5, the magnetic Nano microsphere and magnetic molecularly imprinted polymer of MPS modifications are at 10~30 ° of 2 θ regions
Between there is amorphous maize, show Fe3O4Molecularly imprinted polymer has successfully been modified on magnetic nanoparticle surface.And MPS modifications
Fe is included in magnetic Nano microsphere and magnetic molecularly imprinted polymer3O4The characteristic peak of magnetic nanoparticle, illustrates Fe3O4It is magnetic
The crystalline structure of nano particle is persisted in the magnetic Nano microsphere and magnetic molecularly imprinted polymer of MPS modifications.
Understood refering to Fig. 6, the preparation method of molecularly imprinted polymer of the invention is prepared magnetic molecularly imprinted poly-
The magnetic hysteresis effect of compound is fainter, illustrates the magnetic Nano microsphere of cladding molecularly imprinted polymer at room temperature with super suitable
Magnetism, remanent magnetism will not be retained after externally-applied magnetic field by removing, thus can again rapid dispersion without reuniting.Although magnetic
The saturation magnetization of property molecularly imprinted polymer is less than uncoated Fe3O4Magnetic nanoparticle, but magnetic molecularly imprinted polymerization
The saturation magnetization of thing is enough to make it to magnetic-field-sensitive, and being capable of easily quick separating.
Relative to the prior art, the preparation method of magnetic molecularly imprinted polymer of the invention, using PYR as template molecule,
Amytal is acted on using the multiple hydrogen bonding between amytal and PYR as function monomer, forms intermolecular interaction square
Battle array, increases the binding site of PYR and amytal, thus strengthen template molecule PYR and function monomer amytal it
Between effect, improve magnetic molecularly imprinted polymer to the affinity and Selective adsorption of template molecule PYR.
The invention is not limited in the above embodiment, if the various changes or deformation to the present invention do not depart from the present invention
Spirit and scope, if these changes and deformation belong within the scope of the claim and equivalent technologies of the present invention, then this hair
It is bright to be also intended to comprising these changes and deformation.
Claims (8)
1. the preparation method of the magnetic molecularly imprinted polymer with hydrogen bond array, it is characterised in that：Comprise the following steps：
(1) precipitation method synthesis Fe3O4Magnetic nanoparticle；
(2) sol-gal process prepares the magnetic Nano microsphere Fe of coated silica3O4@SiO2；
(3) with MPS to magnetic Nano microsphere Fe3O4@SiO2Surface modification is carried out, obtains the magnetic Nano microsphere of MPS modifications
Fe3O4@SiO2@MPS；MPS is methacryloxypropyl trimethoxy silane；
(4) template molecule, function monomer are sufficiently mixed in DMSO, then add magnetic Nano microsphere, the crosslinking of MPS modifications
Agent, initiator and decentralized medium, bring it about polymerisation, obtain the molecular engram polymer magnetic of surface coated die plate molecule
Microballoon；
(5) magnetic microsphere obtained in washing step (4), it is dry after removing the template molecule wherein coated, obtain magnetic microsphere
Molecular imprinted polymer on surface Fe3O4@SiO2-MIPs；
Wherein, there is multiple hydrogen bonding effect between the template molecule and function monomer；The template molecule is pyrimethamine, institute
It is amytal to state function monomer.
2. the preparation method of the magnetic molecularly imprinted polymer according to claim 1 with hydrogen bond array, its feature exist
In：
In step (4), the molar ratio of the template molecule and function monomer is 1：1.
3. the system of the magnetic molecularly imprinted polymer with hydrogen bond array according to 1 or 2 any claim of claim
Preparation Method, it is characterised in that：In step (4), the crosslinking agent is divinylbenzene, and the initiator is azodiisobutyronitrile,
The decentralized medium is water.
4. the preparation method of the magnetic molecularly imprinted polymer according to claim 1 with hydrogen bond array, its feature exist
In：
The preparation method of the amytal is：After barbiturates is dissolved in the water, copper-bath is added；It is then injected into
Allyl bromide, bromoallylene, is added dropwise the sodium hydroxide solution that mass fraction is 10%；Stirring reaction 1-3h.
5. the preparation method of the magnetic molecularly imprinted polymer according to claim 3 with hydrogen bond array, its feature exist
In：
By Fe in step (3)3O4@SiO2It is scattered in deionized water, methacryloxy is added after adding hydrochloric acid solution stirring
Propyl trimethoxy silicane, is stirred at room temperature 20-28h；Reaction terminates, Magneto separate, is repeatedly washed respectively with methanol and deionized water,
It is dried to obtain the magnetic Nano microsphere of MPS modifications.
6. the preparation method of the magnetic molecularly imprinted polymer according to claim 3 with hydrogen bond array, its feature exist
In：
Pyrimethamine and amytal are dissolved in DMSO in step (4), fully shake up mixing, room temperature places 10-14h；
Fe is added thereto3O4@SiO2@MPS, crosslinking agent, initiator and decentralized medium, after uniform stirring 20-40min, in nitrogen
Under protective condition, 10-14h is reacted at 60-80 DEG C.
7. the preparation method of the magnetic molecularly imprinted polymer according to claim 6 with hydrogen bond array, its feature exist
In：
In step (4), the volume ratio of DMSO and decentralized medium is 1:8.
8. the preparation method of the magnetic molecularly imprinted polymer according to claim 1 with hydrogen bond array, its feature exist
In：
It is 2 that volume ratio is used in step (5):8 acetic acid and methanol solution surname extraction removes template molecule pyrimethamine.
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