CN106279698A - A kind of 2,4 dinitrophenol,DNP molecular imprinted polymer on surface and its preparation method and application - Google Patents
A kind of 2,4 dinitrophenol,DNP molecular imprinted polymer on surface and its preparation method and application Download PDFInfo
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- CN106279698A CN106279698A CN201610725212.5A CN201610725212A CN106279698A CN 106279698 A CN106279698 A CN 106279698A CN 201610725212 A CN201610725212 A CN 201610725212A CN 106279698 A CN106279698 A CN 106279698A
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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Abstract
The invention discloses a kind of 2,4 dinitrophenol,DNP molecular imprinted polymer on surface and its preparation method and application.Technical scheme main points are: with activated silica gel as carrier, dehydrated alcohol is solvent, 2,4 dinitrophenol,DNP are template molecule, and 3 aminopropyl triethoxysilanes are function monomer, tetraethyl orthosilicate is cross-linking agent, glacial acetic acid is initiator, and in 30 DEG C of water-baths, vibration causes polymerization 9 30h, eluted template molecule or carry out surname extraction, again with methanol obtains target product 2,4 dinitrophenol,DNP molecular imprinted polymer on surface in 60 DEG C of vacuum drying after cleaning.The present invention prepare 2,4 dinitrophenol,DNP molecular imprinted polymer on surface uniform particle sizes, good mechanical performance, selective absorption sexuality is strong, and adsorption capacity is big, it is easy to regeneration cycle uses, can be used in complex environment sample solution 2,4 dinitrophenol,DNP and 2, the high selective separation enrichment pre-treatment of 4,6 trinitrophenols.
Description
Technical field
The invention belongs to for the technical field of absorbent of 2,4-DNP in environment, be specifically related to a kind of 2,4-bis-
Nitrophenol molecular imprinted polymer on surface and its preparation method and application.
Background technology
Nitrophenol is the industrial chemicals that a class is important and conventional, and it is widely used as a kind of raw material or intermediate
In explosive, medicine, insecticide, dyestuff, timber preservative and rubber etc. produce, thus cause the industrial wastewater of nitrobenzene-containing phenol
A large amount of discharges.Phenol compound is that one has Cytotoxic material, is not only difficult to biodegradation, it is also possible to former with cell
Protein generation chemical reaction in slurry forms denatured protein so that cell loses activity, and causes very toxic.Although it is low dense
The phenol type substances of degree is inconspicuous to local lesion within a short period of time, but its penetration is strong, can be by deep tissues
Infiltration accumulation, brings more serious harm.Therefore, the phenol polluter in water environment is effectively removed purification there is weight
Want meaning.
At present, although in water body there being the minimizing technology of the phenol type substances such as method such as chemical oxidation, ozone oxidation and photodissociation
Effect, but implementation process expense is too high, it is difficult to it is applied to the purified treatment engineering field of extensive waste water；And to be adsorbed as master's
Physical method mainly uses activated carbon granule, and it is difficult to regeneration while high-efficient purification phenols in water polluter and follows
Ring utilizes, and easily causes new environmental pollution.Therefore, phenol pollutant efficient, cheap, green and that can be recycled are developed
Matter scavenging material is the key effectively purifying phenol type substances.
Molecularly imprinted polymer is that the one that latest developments are got up has high-selectivity adsorption ability to specific objective material
Material, it has, and identification ability is strong, good stability, anti-adverse environment and the advantage such as can be recycled, thus has as one
The sorbent material of effect, in complex system, the isolation of purified pre-treatment field of pollutant quickly grows.Current molecular engram
Polymer is prepared mostly in high toxicity organic solvent, and not only preparation process is complicated, and reaction time is longer, and resulting polymers
Post processing is the most relatively cumbersome, constrains the application at environmental area of the molecularly imprinted polymer material to a certain extent.
Molecular imprinted polymer on surface is to realize high molecular polymerization at carrier surface, the molecular imprinted polymer on surface obtained
Material particle size is uniform, fast to object recognition rate, and regeneration efficiency is high.Many in " sol-gel " method based on silica gel
Carry out in ethanol, it is not necessary to a large amount of volatility toxic organic solvents, and easy and simple to handle, polyphosphazene polymer can be caused at normal temperatures
Close reaction.Therefore combining by " sol-gel " and molecular imprinting, can realize the system of molecularly imprinted polymer
Standby process greenization and easy, obtained imprinted polymer material not only absorption property is superior, is greatly shortened polymer
Preparation time, and material simply regenerates, and is conducive to expanding molecularly imprinted polymer application in environmental contaminants improvement field.
Summary of the invention
Present invention solves the technical problem that there is provided a kind of 2,4-dinitrophenol,DNP molecular imprinted polymer on surface and
Preparation method, prepared 2,4-DNP molecular imprinted polymer on surface uniform particle sizes, good mechanical performance, selectivity is inhaled
Attached sexuality is strong, and adsorption capacity is big, it is easy to regeneration cycle uses, it is possible to 2,4-DNP in complex environment sample solution
High selective separation enrichment pre-treatment with 2,4,6-trinitrophenol.
The present invention solves that above-mentioned technical problem adopts the following technical scheme that, a kind of 2,4-DNP surface molecular print
The preparation method of mark polymer, it is characterised in that: with activated silica gel as carrier, dehydrated alcohol is solvent, 2,4-DNP
For template molecule, 3-aminopropyl triethoxysilane is function monomer, and tetraethyl orthosilicate is cross-linking agent, and glacial acetic acid is for causing
Agent, in 30 DEG C of water-baths, vibration causes polymerization 9-30h, the methanol/ethanol mixed solution that product volume ratio is 9/1 that will obtain
Vibration eluting or the methanol/ethanol mixed solution surname extraction that product volume ratio is 9/1 that will obtain, again with methanol is cleaned
After obtain target product 2,4-dinitrophenol,DNP molecular imprinted polymer on surface in 60 DEG C of vacuum drying.
Further preferably, described support-activated silica gel quality with the ratio of the mole of template molecule 2,4-DNP is
1g:1mmol, described template molecule 2,4-DNP, function monomer 3-aminopropyl triethoxysilane and the positive silicon of cross-linking agent
The molar ratio of acid tetra-ethyl ester is 1:2-12:10-35.
2,4-DNP molecular imprinted polymer on surface of the present invention, it is characterised in that be by said method system
For obtain, the structural formula of this 2,4-DNP molecular imprinted polymer on surface is:
2,4-dinitrophenol,DNP molecular imprinted polymer on surface of the present invention is at selective separation enrichment complex environment sample
Application in 2,4-dinitrophenol,DNP and 2,4,6-trinitrophenol in solution.
Further preferably, described 2,4-DNP molecular imprinted polymer on surface is complicated at selective separation enrichment
Application in 2,4-DNP and 2，4，6-trinitrophenol in environmental sample solution, it is characterised in that detailed process is:
2,4-DNP molecular imprinted polymer on surface is joined in complex environment sample solution, under room temperature condition, stand 3h
Complete adsorption process；2,4-DNP molecular imprinted polymer on surface solid-liquid separation after absorption being used, is separating
To solid in add volume ratio be 40/40/20 methanol/water/alcohol mixed solution, under room temperature condition, be standing and soak for 1h,
Repeat after solid-liquid separation to soak 3-5 time, after cleaning-drying, obtain the 2,4-DNP molecular imprinted polymer on surface of regeneration
Repetitive cycling uses.
Further preferably, in described complex environment sample solution, the molar concentration of 2,4-DNP is 0.5-
3mol/L, 2,4-DNP in complex environment sample solution is gone by 2,4-DNP molecular imprinted polymer on surface
Except rate reaches more than 71%.
Present invention preferably employs the method that " sol-gel " combines with " surface molecule print ", sol-gel is a kind of
Comparatively gentle method, it is only necessary to relatively low synthesis temperature (25-30 DEG C), and in collosol-gelatum system, being diffused in of component is received
In the range of meter, therefore polyreaction easily causes.2,4-DNP molecular imprinted polymer on surface in the present invention, at ice
It is prepared under acetic acid (1mol/L) initiation, 30 DEG C of water-bath oscillating conditions, the 2,4-DNP surface molecule print obtained
Polymer has that epigranular, specific surface area be big, big to the adsorbance of 2,4-dinitrophenol,DNP and selective adsorption capacity is strong etc.
Feature.The preparation technology of this 2,4-DNP molecular imprinted polymer on surface is simple, and polymerization time is short, selective absorption energy
Power is strong, has good development prospect in terms of processing 2,4-DNP pollutant.
Accompanying drawing explanation
Fig. 1 is the technology of preparing route schematic diagram of the present invention.
Detailed description of the invention
By the following examples the foregoing of the present invention is described in further details, but this should be interpreted as this
The scope inventing above-mentioned theme is only limitted to below example, and all technology realized based on foregoing of the present invention belong to this
Bright scope.
Embodiment 1
With 20mL dehydrated alcohol as solvent, 0.2g activated silica gel is carrier, and 0.037g 2,4-DNP is template molecule,
3-aminopropyl triethoxysilane is function monomer, and tetraethyl orthosilicate is cross-linking agent (wherein 2,4-DNP, 3-ammonia third
Ethyl triethoxy silicane alkane is 1:2:10 with the molar ratio of tetraethyl orthosilicate), 0.5mL glacial acetic acid (1mol/L) is for causing
Agent, in 30 DEG C of water-baths, vibration causes polymerization 9h, by methanol/acetic acid mixed solution rope that the product volume ratio obtained is 9/1
Family name extracts 48h, and again with methanol obtains 2,4-DNP molecular imprinted polymer on surface in 60 DEG C of vacuum drying after cleaning.
Embodiment 2
With 20mL dehydrated alcohol as solvent, 0.2g activated silica gel is carrier, and 0.037g 2,4-DNP is template molecule,
3-aminopropyl triethoxysilane is function monomer, and tetraethyl orthosilicate is cross-linking agent (wherein 2,4-DNP, 3-ammonia third
Ethyl triethoxy silicane alkane is 1:6:20 with the molar ratio of tetraethyl orthosilicate), 0.5mL glacial acetic acid (1mol/L) is for causing
Agent, in 30 DEG C of water-baths, vibration causes polyase 13 0h, is shaken by methanol/acetic acid mixed solution that the product volume ratio obtained is 9/1
Swinging eluting 5 times (1h/ time), again with methanol obtains 2,4-DNP surface molecule print in 60 DEG C of vacuum drying after cleaning and gathers
Compound.
Embodiment 3
With 20mL dehydrated alcohol as solvent, 0.2g activated silica gel is carrier, and 0.037g 2,4-DNP is template molecule,
3-aminopropyl triethoxysilane is function monomer, and tetraethyl orthosilicate is cross-linking agent (wherein 2,4-DNP, 3-ammonia third
Ethyl triethoxy silicane alkane is 1:12:35 with the molar ratio of tetraethyl orthosilicate), 0.5mL glacial acetic acid (1mol/L) is for causing
Agent, in 30 DEG C of water-baths, vibration causes polymerization 16h, by methanol/acetic acid mixed solution rope that the product volume ratio obtained is 9/1
Family name extracts 48h, and again with methanol obtains 2,4-DNP molecular imprinted polymer on surface in 60 DEG C of vacuum drying after cleaning.
Embodiment 4
With 20mL dehydrated alcohol as solvent, 0.2g activated silica gel is carrier, and 0.037g 2,4-DNP is template molecule,
3-aminopropyl triethoxysilane is function monomer, and tetraethyl orthosilicate is cross-linking agent (wherein 2,4-DNP, 3-ammonia third
Ethyl triethoxy silicane alkane is 1:8:20 with the molar ratio of tetraethyl orthosilicate), 0.5mL glacial acetic acid (1mol/L) is for causing
Agent, in 30 DEG C of water-baths, vibration causes polymerization 15h, is shaken by methanol/acetic acid mixed solution that the product volume ratio obtained is 9/1
Swinging eluting 6 times (1h/ time), again with methanol obtains 2,4-DNP surface molecule print in 60 DEG C of vacuum drying after cleaning and gathers
Compound.
Embodiment 5
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL molar concentration is 0.5mmol/L(92mg/L) 2,4-DNP ethanol solution in, left at room temperature soak 3h.
Testing result shows, under the conditions of adsorption equilibrium, 2,4-DNP molecular imprinted polymer on surface to 2,4-dinitro benzene
The adsorption capacity of phenol reaches 89 μm ol/g(16mg/g), clearance is 89%, and corresponding non-imprinted polymer is to 2,4-dinitro
The adsorbance of phenol is 11 μm ol/g(2mg/g), clearance is only 11%.After material solid-liquid separation after absorption is used, add
1mL volume ratio is the methanol/water/acetic acid mixed solution of 40/40/20, and left at room temperature soaks 1h, repeats leaching after solid-liquid separation
Steeping 3 times, obtain the 2,4-DNP molecular imprinted polymer on surface of regeneration and non-imprinted polymer after cleaning-drying, it is right
The adsorbance of 2,4-dinitrophenol,DNP and adsorption efficiency are without significant change.
Embodiment 6
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL molar concentration is 1mmol/L(184mg/L) 2,4-DNP ethanol solution in, left at room temperature soak 3h.Inspection
Survey result shows, under the conditions of adsorption equilibrium, 2,4-DNP molecular imprinted polymer on surface is to 2,4-DNP
Adsorption capacity reach 165 μm ol/g(31mg/g), clearance is 83%, and corresponding non-imprinted polymer is to 2,4-dinitro
The adsorbance of phenol is 16 μm ol/g(8mg/g), clearance is only 8%.Material solid-liquid after absorption being used divides
From rear, adding methanol/water/acetic acid mixed solution that 1mL volume ratio is 40/40/20, left at room temperature soaks 1h, solid-liquid
Repeat immersion 3 times after separation, after cleaning-drying, obtain the 2,4-DNP molecular imprinted polymer on surface and non-of regeneration
Polymer, its to the adsorbance of 2,4-DNP and adsorption efficiency without significant change.
Embodiment 7
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL molar concentration is 3mmol/L(552mg/L) 2,4-DNP ethanol solution in, left at room temperature soak 3h.Inspection
Survey result shows, under the conditions of adsorption equilibrium, 2,4-DNP molecular imprinted polymer on surface is to 2,4-DNP
Adsorption capacity reach 424 μm ol/g(78mg/g), clearance is 71%, and corresponding non-imprinted polymer is to 2,4-dinitro
The adsorbance of phenol is 17 μm ol/g(3mg/g), clearance is only 3%.After material solid-liquid separation after absorption is used, add
1mL volume ratio is the methanol/water/acetic acid mixed solution of 40/40/20, and left at room temperature soaks 1h, repeats leaching after solid-liquid separation
Steeping 3 times, obtain 2,4-DNP molecular imprinted polymer on surface and the non-polymer material of regeneration after cleaning-drying, it is right
The adsorbance of 2,4-dinitrophenol,DNP and adsorption efficiency are without significant change.
Embodiment 8
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL molar concentration is 6mmol/L(1105mg/L) 2,4-DNP ethanol solution in, left at room temperature soak 3h.
Testing result shows, under the conditions of adsorption equilibrium, 2,4-DNP molecular imprinted polymer on surface to 2,4-dinitro benzene
The adsorption capacity of phenol reaches 625 μm ol/g(115mg/g), clearance is 45%, and corresponding non-imprinted polymer is to 2,4-dinitro
The adsorbance of base phenol is 23 μm ol/g(4mg/g), clearance is only 1%.After material solid-liquid separation after absorption is used, add
Entering methanol/water/acetic acid mixed solution that 1mL volume ratio is 40/40/20, left at room temperature soaks 1h, repeats after solid-liquid separation
Soak 3 times, after cleaning-drying, obtain 2,4-DNP molecular imprinted polymer on surface and the non-polymer material of regeneration, its
Adsorbance and adsorption efficiency to 2,4-dinitrophenol,DNP are without significant change.
Embodiment 9
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL molar concentration is the 2,4-dinitrophenol,DNP of 1mmol/L, 2-nitrophenol, 3-nitrophenol, 4-nitrophenol, 2,4,6-
Trinitrophenol, 2,4 dichloro phenol, 2,4,6-trichlorophenol, 2,4,6,-T, phenol, N-butylpyridinium Chloride, metronidazole, o-aminophenol,
The ethanol solution of 13 kinds of substrates such as sulfanilamide or bromination-1-butyl-3-vinyl imidazole, is standing and soak for 3h under room temperature condition.Detection
Result shows, under the conditions of adsorption equilibrium, 2,4-DNP molecular imprinted polymer on surface to 2,4-DNP and
The adsorbance of 2，4，6-trinitrophenol is respectively 165 μm ol/g(31mg/g) and 187 mol/g(42mg/g), clearance is respectively
It is 83% and 93%, and less to the adsorbance of other 11 kinds of substrates, and clearance is respectively less than 15%.
Embodiment 10
Take the above-mentioned prepared 2,4-DNP molecular imprinted polymer on surface of 10mg and non-imprinted polymer, be separately added into
2mL contains 2,4-dinitrophenol,DNP (0.025mmol/L), N-butylpyridinium Chloride (0.02mmol/L), 2-nitrophenols
(0.08mmol/L) and the alcohol mixed solution of phenol (0.3mmol/L), it is standing and soak for 3h under room temperature condition.Testing result shows
Show, under the conditions of adsorption equilibrium, the 2,4-DNP molecular imprinted polymer on surface adsorbance to 2,4-DNP
It is 4.5 mol/g(8mg/g), clearance reaches 91%, and to the N-butylpyridinium Chloride coexisted, 2-nitrophenols and phenol the most not
Absorption.Corresponding non-imprinted polymer 2,4-dinitrophenol,DNP, N-butylpyridinium Chloride, 2-nitrophenols and phenol to coexisting is several
Do not adsorb.
Embodiment above describes the ultimate principle of the present invention, principal character and advantage, the technical staff of the industry should
Understanding, the present invention is not restricted to the described embodiments, and the simply explanation present invention's described in above-described embodiment and description is former
Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within
In the scope of protection of the invention.
Claims (6)
1. the preparation method of a 2,4-DNP molecular imprinted polymer on surface, it is characterised in that: with activated silica gel be
Carrier, dehydrated alcohol is solvent, and 2,4-DNP is template molecule, and 3-aminopropyl triethoxysilane is function monomer,
Tetraethyl orthosilicate is cross-linking agent, and glacial acetic acid is initiator, and in 30 DEG C of water-baths, vibration causes polymerization 9-30h, the product that will obtain
Thing volume ratio is the methanol/ethanol mixed solution vibration eluting of 9/1 or is the first of 9/1 by the product volume ratio that obtains
Alcohol/alcohol mixed solution surname extraction, again with methanol obtains target product 2,4-dinitro benzene in 60 DEG C of vacuum drying after cleaning
Phenol molecular imprinted polymer on surface.
The preparation method of 2,4-DNP molecular imprinted polymer on surface the most according to claim 1, its feature exists
In: the quality of described support-activated silica gel is 1g:1mmol with the ratio of the mole of template molecule 2,4-DNP, described
Template molecule 2,4-dinitrophenol,DNP, function monomer 3-aminopropyl triethoxysilane feed intake with cross-linking agent tetraethyl orthosilicate
Mol ratio is 1:2-12:10-35.
3. a 2,4-DNP molecular imprinted polymer on surface, it is characterised in that be by the side described in claim 1 or 2
Method prepares, and the structural formula of this 2,4-DNP molecular imprinted polymer on surface is:
。
4. the 2,4-dinitrophenol,DNP molecular imprinted polymer on surface described in claim 3 is at selective separation enrichment complex environment
Application in 2,4-dinitrophenol,DNP and 2,4,6-trinitrophenol in sample solution.
2,4-dinitrophenol,DNP molecular imprinted polymer on surface the most according to claim 4 is complicated at selective separation enrichment
Application in 2,4-DNP and 2，4，6-trinitrophenol in environmental sample solution, it is characterised in that detailed process is:
2,4-DNP molecular imprinted polymer on surface is joined in complex environment sample solution, under room temperature condition, stand 3h
Complete adsorption process；2,4-DNP molecular imprinted polymer on surface solid-liquid separation after absorption being used, is separating
To solid in add volume ratio be 40/40/20 methanol/water/alcohol mixed solution, under room temperature condition, be standing and soak for 1h,
Repeat after solid-liquid separation to soak 3-5 time, after cleaning-drying, obtain the 2,4-DNP molecular imprinted polymer on surface of regeneration
Repetitive cycling uses.
2,4-dinitrophenol,DNP molecular imprinted polymer on surface the most according to claim 5 is complicated at selective separation enrichment
Application in 2,4-DNP and 2，4，6-trinitrophenol in environmental sample solution, it is characterised in that: described complicated ring
In the sample solution of border, the molar concentration of 2,4-DNP is 0.5-3mol/L, and 2,4-DNP surface molecule print gathers
Compound reaches more than 71% to the clearance of 2,4-dinitrophenol,DNP in complex environment sample solution.
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| CN107649101A (en) * | 2017-09-29 | 2018-02-02 | 湖南大学 | Mercapto-functionalized titania molecule trace composite and its aqueous phase preparation method and application |
| CN107837799A (en) * | 2017-11-16 | 2018-03-27 | 河南永泽环境科技有限公司 | A kind of magnetic for phenol wastewater of degrading strengthens flyash trace photochemical catalyst |
| CN108014758A (en) * | 2017-12-13 | 2018-05-11 | 太原理工大学 | Microwave radiation technology magnetism p-nitrophenol surface molecule print solid phase extraction material |
| CN111266097A (en) * | 2020-01-20 | 2020-06-12 | 中山大学 | Molecularly imprinted microextraction column for specifically adsorbing 2,6-DCBQ and preparation method and application thereof |
| CN112679747A (en) * | 2020-12-22 | 2021-04-20 | 北京工商大学 | Molecularly imprinted polymer for detecting alkylresorcinol and preparation method and application thereof |
| CN116571222A (en) * | 2023-07-06 | 2023-08-11 | 北京建工环境修复股份有限公司 | Pentachlorophenol surface imprinting magnetic microsphere and preparation method thereof |
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| CN107649101A (en) * | 2017-09-29 | 2018-02-02 | 湖南大学 | Mercapto-functionalized titania molecule trace composite and its aqueous phase preparation method and application |
| CN107649101B (en) * | 2017-09-29 | 2019-09-10 | 湖南大学 | Mercapto-functionalized titania molecule trace composite material and its aqueous phase preparation method and application |
| CN107837799A (en) * | 2017-11-16 | 2018-03-27 | 河南永泽环境科技有限公司 | A kind of magnetic for phenol wastewater of degrading strengthens flyash trace photochemical catalyst |
| CN107837799B (en) * | 2017-11-16 | 2020-06-23 | 河南永泽环境科技有限公司 | Magnetic reinforced fly ash imprinted photocatalyst for degrading phenol-containing wastewater |
| CN108014758A (en) * | 2017-12-13 | 2018-05-11 | 太原理工大学 | Microwave radiation technology magnetism p-nitrophenol surface molecule print solid phase extraction material |
| CN111266097A (en) * | 2020-01-20 | 2020-06-12 | 中山大学 | Molecularly imprinted microextraction column for specifically adsorbing 2,6-DCBQ and preparation method and application thereof |
| CN112679747A (en) * | 2020-12-22 | 2021-04-20 | 北京工商大学 | Molecularly imprinted polymer for detecting alkylresorcinol and preparation method and application thereof |
| CN116571222A (en) * | 2023-07-06 | 2023-08-11 | 北京建工环境修复股份有限公司 | Pentachlorophenol surface imprinting magnetic microsphere and preparation method thereof |
| CN116571222B (en) * | 2023-07-06 | 2023-09-26 | 北京建工环境修复股份有限公司 | Pentachlorophenol surface imprinting magnetic microsphere and preparation method thereof |
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