CN107597080A - A kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent - Google Patents
A kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent Download PDFInfo
- Publication number
- CN107597080A CN107597080A CN201711033751.3A CN201711033751A CN107597080A CN 107597080 A CN107597080 A CN 107597080A CN 201711033751 A CN201711033751 A CN 201711033751A CN 107597080 A CN107597080 A CN 107597080A
- Authority
- CN
- China
- Prior art keywords
- crosslinking agent
- imprinted polymer
- exempting
- function monomer
- molecularly imprinted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The present invention relates to a kind of novel preparation method for the molecularly imprinted polymer for exempting from function monomer and crosslinking agent.This method is：It is transferred to after tea seed shell powder stock and phloroglucin auxiliary agent and template molecule are sufficiently mixed in water in stainless steel cauldron, irregular hole trace is formed in microballoon by low-temperature hydrothermal reaction simultaneously in generation carbosphere.This preparation method technique is tight, simple and easy, and product impurity content is low, pattern is good, is the roughish spheric granules in regular and surface, and particle diameter is about 1.5 μm, is a kind of very good method for preparing molecularly imprinted polymer.It is wide material sources, cheap and this method raw material is biomass castoff；Preparation process need not use the function monomer and crosslinking agent of poisonous organic solvent and costliness；Obtained imprinted polymer uniform particle sizes, biocompatibility is high, environment-friendly, and its product is expected to be used widely in biology, pharmacy and a variety of industrial circles.
Description
Technical field
The invention belongs to molecularly imprinted polymer functional material preparing technical field, and in particular to one kind exempt from function monomer and
The novel preparation method of the biomass molecule imprinted carbon microspheres of crosslinking agent.
Background technology
The preparation principle of molecularly imprinted polymer is in solvent environment, passes through being total between function monomer and template molecule
Valence link or non-covalent bond be self-assembly of the compound or derivative of template molecule, add appropriate crosslinking agent, pore
Agent and initiator, the initiated polymerization under low temperature and irradiance or heating condition, high molecular polymer of the generation with high-crosslinking-degree,
So that function monomer and template molecule are fixed in the tridimensional network of polymer, so that the functional group tool on monomer
Have specific space arrangement and space conformation, through extraction or the methods of sour water solution by template molecule elution after, gather in molecular engram
, binding site complementary imprinted sites close with the spatial configuration of molecules of template and size have been left with compound, this
Site selectively can be combined with template molecule, so that it possesses the function to template molecule specific recognition.Molecule prints
Mark polymer, which prepares primary raw material used, includes function monomer, crosslinking agent, template molecule, initiator, organic solvent etc..
Problems, such as work(be present in traditional molecular imprinting technology such as polymerisation in bulk, precipitation polymerization, surface imprinted polymerization etc.
The selection limitation of energy monomer, crosslinking agent and polymerization is larger；Function monomer and crosslinking agent etc. are to synthesize compound, price
It is expensive；Most immunoblot methods are mainly carried out in nonpolar organic media, are using the same of a large amount of poisonous and harmful organic reagents
When, also the use of molecularly imprinted polymer in aqueous is limited, and generally biocompatibility and biological degradability are poor.
In addition, traditional molecular imprinting technology usually requires the steps such as modification and the prepolymerization to carrier, course of reaction very complicated.
Use natural polysaccharide to prepare natural polymer quasi-molecule imprinted polymer for base stock, there are many advantages.
Such as, many having on polysaccharide macro-molecular chain is available for the functional groups of reaction（Such as-OH ,-NH2Deng）Can directly and crosslinking agent
Cross-linked polymeric；Prepared imprinted polymer has excellent biocompatibility and biological degradability；Raw material sources extensively, can be again
Raw and advantage of lower cost.Use natural polysaccharide biomass to be directly crosslinked, the synthesis such as graft copolymerization and sol-gel technique
Molecularly imprinted polymer has been studied, but the polysaccharide biomass used at present is pure material, such as cyclodextrin, chitosan, fiber
Element, starch, agarose, alginic acid etc. [Wang Hongfei, Zhang Liming, polysaccharide-based function of molecular engram material, chemical progress, 2010,22
（11）：2165-2172], economic benefit is not notable.And the preparation technology being related to is both needed to the crosslinking agent thing of additional synthesis mostly
Matter, biocompatibility are limited.
The content of the invention
It is an object of the invention to provide it is a kind of without function monomer, crosslinking agent and harmful organic solvent using biomass as
The molecularly imprinted polymer novel preparation method of raw material.Using natural biomass tea seed shell powder as base stock, with deionization
Water is solvent, with perfluorooctane sulfonate potassium（PFOS）It is auxiliary agent in phloroglucin or perfluorooctane sulfonate (PFOA) is template molecule
Under the conditions of, by low-temperature hydrothermal carburizing reagent, irregular hole trace is formed in microballoon while carbosphere is prepared.
The present invention is realized by the following technical scheme, a kind of to exempt from function monomer and the molecular engram of crosslinking agent gathers
Compound novel preparation method, its feature include following process：
（1）It is 2 ~ 74 μm of tea seed shell powder stocks, phloroglucin auxiliary agent and template molecule to weigh a certain amount of particle diameter first, with
Deionized water is well mixed with certain proportion, is added in reactor, and reactor is put into 200-240 DEG C of air dry oven constant temperature
Certain time is reacted, naturally cools to room temperature；
（2）By step（1）Middle gained solid product cleaned repeatedly with solvent supersonic it is colourless to cleaning solution, then using solvent super
Cleaned in sound-microwave synergistic extraction instrument, solid sample after cleaning is dried in vacuum drying chamber；
（3）Take a certain amount of step（2）Sample is placed in Soxhlet extraction device in filter paper bag after middle drying, is existed using certain solvent
The template molecule in 72h removing imprinted carbon microspheres is heated under water bath condition.Sample after eluted template is 60 in vacuum drying chamber
DEG C dry 12h, obtain imprinted carbon microspheres.
Used raw material is tea seed shell powder, and auxiliary agent is phloroglucin, and solvent is deionized water.
The mass ratio of used tea seed shell powder stock and phloroglucin is 3.5:1~4.5:1 （w/w, g/g）.
Used tea seed shell powder stock and phloroglucin gross mass and the solid-liquid ratio of water are 1:40~1:25（w/
v, g/ml）.
Used template molecule is perfluorooctane sulfonate potassium or perfluorooctane sulfonate.
The mass ratio of used tea seed shell powder stock and template molecule is：10:1~12.5:1 （w/w, g/g）.
The isothermal reaction time is 10 ~ 14 h.
The solvent for being cleaned by ultrasonic the solid product taken out from reactor is deionized water and absolute ethyl alcohol.
Ultrasound-microwave cooperating cleaning solvent is 50% ethanol-water solution, and ultrasound-microwave cooperating cleaning temperature is 55 ~ 65
DEG C, ultrasound-microwave cooperating scavenging period is 25 ~ 40min, at least 3 times.
Surname extraction solvent is 50% Ethanol-Acetic Acid solution, and the surname extraction time is 72h.
General steps are：（1）For the tea seed shell powder for being 2-74 μm using particle diameter as primary raw material, phloroglucin is auxiliary agent,
Perfluorooctane sulfonate potassium or perfluorooctane sulfonate are template molecule；By raw material, auxiliary agent, template molecule and deionized water with solid-to-liquid ratio 1:40
~1:25（w/v, g/ml）Ratio mixes.Wherein the mass ratio of tea seed shell powder and phloroglucin is 3.5:1~4.5:1 （w/
w, g/g）, the mass ratio of tea seed shell powder and template molecule is 10:1~12.5:1 （w/w, g/g）.After being sufficiently mixed uniformly
It is added in reactor, room temperature is cooled to after reactor is put into 200-240 DEG C of 11 ~ 16h of air dry oven isothermal reaction.
（2）By step（1）Middle reactor liquid pouring at the middle and upper levels, solid is taken out, successively with deionized water and absolute ethyl alcohol
Be cleaned by ultrasonic it is colourless to cleaning solution, then using 50% ethanol solution in microwave and ultrasonic wave synergic extraction instrument at 55 ~ 65 DEG C it is clear
It is washed till 3 times less, at least 30min, solid sample after cleaning is dried in 60 DEG C of vacuum drying chambers every time.
（3）Take a certain amount of step（2）Sample is placed in Soxhlet extraction device in filter paper bag after middle drying, using methanol/
Acetic acid（v/v, 70/30）Solution removes the template molecule in imprinted carbon microspheres in 60 DEG C of heating water bath 72h.After eluted template
Sample 60 DEG C of dry 12h in vacuum drying chamber, obtain molecular engram carbosphere.Template molecule preparation is not added under similarity condition
Non- imprinted carbon microspheres, carry out control experiment.
（4）Adsorption dynamics adsorption kinetics evaluation method of the imprinted carbon microspheres to template molecule.
（5）Adsorption isotherm preparation method of the imprinted carbon microspheres to template molecule.
The present invention has the following advantages：Technique is tight, simple and easy；Preparing raw material is peculiar from a kind of south China
And the substantial amounts of oil crops-oil tea process of plantation accessory substance, i.e. tea seed shell, it is a kind of wide material sources, price
Cheap green renewable resource；Product impurity content is low, pattern is good；And preparation process need not use toxic organic solvents and
Expensive function monomer and crosslinking agent；Obtained imprinted polymer uniform particle sizes, biocompatibility is high, environment-friendly.
Brief description of the drawings
The accompanying drawing for forming the present invention is for providing a further understanding of the present invention, embodiments of the invention and its explanation
For explaining the present invention, inappropriate limitation of the present invention is not formed.In the accompanying drawings：
Fig. 1 is the SEM figures of non-imprinted carbon microspheres and the molecular engram carbosphere described in the embodiment of the present invention.
Wherein non-imprinted carbon microspheres（a）And imprinted carbon microspheres（b）SEM.
Fig. 2 is adsorption dynamics adsorption kinetics of non-imprinted carbon microspheres and the molecular engram carbosphere described in the embodiment of the present invention to PFOS
Curve.
Fig. 3 is pH value to absorption of non-imprinted carbon microspheres and the molecular engram carbosphere to PFOS described in the embodiment of the present invention
Influence curve.
Fig. 4 is adsorption isotherm of non-imprinted carbon microspheres and the molecular engram carbosphere described in the embodiment of the present invention to PFOS
Line.
Embodiment
Example below is merely to illustrate the embodiment of the present invention, but the invention is not restricted to above-mentioned embodiment,
In the field those of ordinary skill possessed knowledge, that is made within the spirit and principles in the present invention any repaiies
Change, equivalent substitute and improvement etc., it all should cover within the scope of the claimed technical scheme of the present invention.
In the following embodiments, the process and method not being described in detail are conventional method well known in the art, are used
Reagent be that commercially available analysis is pure or more.Following embodiments realize the goal of the invention of the present invention.
Embodiment 1
The present embodiment is related to perfluorooctane sulfonate imprinted polymer carbosphere and its preparation.
0.8g tea seed shells powder, 0.2g phloroglucins and 0.08g potassium perfluoroctane sulfonates are taken in beaker, is added
30mL deionized waters, it is fully dissolved using magnetic agitation 6h scattered, then beaker is placed in large power supersonic instrument and disperseed
0.5h, it is transferred to afterwards in the stainless steel cauldron of polytetrafluoroethyllining lining, the hydro-thermal reaction 12h in 230 DEG C of air dry ovens,
Reaction naturally cools to room temperature after terminating.The solid obtained after separation reaction, using deionized water, absolute ethyl alcohol, alternately ultrasound is clear
Wash, to its ultrasound after cleaning solution close to colourless.Ethanol water is used afterwards（V/V=50/50）Cooperateed with for solvent in ultrasonic-microwave
Cleaned in abstraction instrument, the sample after cleaning dries 12h in 60 DEG C of vacuum drying chambers.
Sample is placed in Soxhlet extraction device in filter paper bag after taking a certain amount of drying, uses methanol/acetic acid solution（V/V=
70/30）Heating water bath 72h removes the template molecule PFOS in imprinted carbon microspheres.Sample after eluted template is in vacuum drying chamber
In 60 DEG C of dry 12h, obtain PFOS trace tea seed shell carbospheres.
For non-trace tea seed shell carbosphere in addition to template molecule PFOS is not added in preparation process, remaining preparation method is equal
It is same as described above.
Fig. 1 is the SEM figures of the imprinted carbon microspheres and non-trace obtained by the method for embodiment 1.As seen from the figure, non-trace
Carbosphere is in Soxhlet extraction device after methanol/acetic acid solution cleaning, and its pattern does not produce significant change, and impurity contains in sample
Measure low, spheroid is regular, and surface is smooth, no significant defect, and its particle diameter is about 1.5 μm.With the pattern phase of non-imprinted polymer
Than imprinted polymer still keeps micro-sphere structure, and microsphere surface is slightly coarse, and has a small amount of cotton-shaped projection, and spheroid occurs slight glutinous
Even, particle diameter is about 1.5 μm.The imprinted sites that showing imprinted polymer surface has template molecule are formed.
Embodiment 2
The present embodiment is related to dynamic absorption performance evaluation of the molecular engram carbosphere of the present invention to template molecule.
Using prepared trace in embodiment 1 and non-imprinted carbon microspheres as adsorbent, PFOS is investigated in the aqueous solution thereon
Adsorption dynamics adsorption kinetics performance.Pipette 50mL concentration be 5 mg L-1 the PFOS aqueous solution in two 150 ml conical flasks, point
Non- trace and imprinted carbon microspheres are not added thereto as adsorbent, quality is 25 mg.Conical flask is positioned over to 20 DEG C of constant temperature
In oscillator, adsorbed with 150 r/min speed oscillation, 1 ml is sampled in default adsorption time, after centrifuging out supernatant
Wherein PFOS concentration, and adsorbance corresponding to calculating are determined using LC-MS.
Fig. 2 is the curve of adsorption kinetics of imprinted carbon microspheres and non-imprinted carbon microspheres to PFOS in the aqueous solution.By being tied in figure
Fruit understands that non-imprinted carbon microspheres about reach adsorption equilibrium in 90min, shorter the time required to reaching time of equilibrium adsorption, and it is adsorbed
During resistance to mass tranfer it is smaller, mass transfer rate faster, carbosphere table is occurred mainly in when the aqueous solution to PFOS absorption behavior
Face.Absorption of the imprinted carbon microspheres to PFOS about reaches balance in 180min, and compared to non-imprinted carbon microspheres, its rate of adsorption is slower,
Show that its mass transfer rate is slower, this be probably due in imprinted carbon microspheres have template molecule elution after leave microcellular structure,
These imprinted sites are distributed widely in carbosphere surface or inside, increase to the resistance to mass tranfer in PFOS adsorption processes, cause
Its time of equilibrium adsorption is longer.When reaching adsorption equilibrium, the equilibrium adsorption capacity of imprinted carbon microspheres has relative to non-imprinted carbon microspheres
Significantly improve, show that imprinting effect is more obvious.
Embodiment 3
The present embodiment is related to Adsorption Effect of the solution ph to molecular engram carbosphere of the present invention to template molecule.
Pipette 10 mL initial concentrations be 5 mg L-1 two parts of the PFOS aqueous solution in 25 mL conical flasks, each sample
Parallel 9 parts.Using the 0.1 mol L-1 NaOH aqueous solution and 0.1 mol L-1 HCl/water solution adjust its pH value for 2 ~
10, the non-mg of imprinted carbon microspheres and imprinted carbon microspheres 5 obtained by the method for embodiment 1 is separately added into two parts of samples as suction
Attached dose.Conical flask is positioned in 20 DEG C of constant temperature oscillator, 24h is adsorbed with 150 r/min speed oscillation.After sampling centrifugation
PFOS concentration in its supernatant measure solution, and adsorbance corresponding to calculating.
Fig. 3 is non-imprinted carbon microspheres and imprinted carbon microspheres under different solutions pH to PFOS Adsorption Effects.As seen from the figure,
PH value of solution is more similar to the effect tendency of the two adsorbance.Under the conditions of relatively low pH, adsorbance is as pH increase is presented
Obvious downward trend；After pH increases to 5, adsorbance changes and changed little with pH.
Embodiment 4
The present embodiment is related to adsorption isotherm of the molecular engram carbosphere of the present invention to template molecule.
It is 10 mL to pipette a series of volumes respectively, and concentration range is 0.1 ~ 10 mg L-1 PFOS aqueous solution in 25
In mL conical flasks, it is 3 to adjust its pH value using the 0.1 mol L-1 NaOH aqueous solution and mol L-1 HCl/water solution,
Sample is parallel two parts.Non- imprinted carbon microspheres and imprinted carbon microspheres obtained by the method for embodiment 1 are separately added into two parts of samples
5 mg.Conical flask is positioned in 20 DEG C of constant temperature oscillator, 24h is adsorbed with 150 r/min speed oscillation.After sampling centrifugation
PFOS concentration in its supernatant measure solution, and adsorbance corresponding to calculating.
Fig. 4 is the adsorption isotherm of imprinted carbon microspheres and non-imprinted carbon microspheres to PFOS in the aqueous solution.Use Langmuir
Adsorption Model and Freundlich Adsorption Models are inhaled to non-imprinted carbon microspheres and imprinted carbon microspheres to the isothermal of PFOS in the aqueous solution
After attached data fitting, it is respectively 293 μ gg-1 and 538 μ gg-1 to find its maximal absorptive capacity.Compared to non-imprinted carbon microspheres,
The maximal absorptive capacity of imprinted carbon microspheres has obvious increase, shows that imprinted carbon microspheres surface has the trace position of template molecule
Point, its adsorbance to PFOS is caused substantially to increase.
Claims (10)
1. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent, it is characterised in that method and step is such as
Under：
（1）It is 2 ~ 74 μm of tea seed shell powder stocks, phloroglucin auxiliary agent and template molecule to weigh a certain amount of particle diameter first, with
Deionized water is well mixed with certain proportion, is added in reactor, and reactor is put into 200-240 DEG C of air dry oven constant temperature
Certain time is reacted, naturally cools to room temperature；
（2）By step（1）Middle gained solid product cleaned repeatedly with solvent supersonic it is colourless to cleaning solution, then using solvent super
Cleaned in sound-microwave synergistic extraction instrument, solid sample after cleaning is dried in vacuum drying chamber；
（3）Take a certain amount of step（2）Sample is placed in Soxhlet extraction device in filter paper bag after middle drying, is existed using certain solvent
The template molecule in 72h removing imprinted carbon microspheres is heated under water bath condition；Sample after eluted template is 60 in vacuum drying chamber
DEG C dry 12h, obtain imprinted carbon microspheres.
2. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, used raw material is tea seed shell powder, and auxiliary agent is phloroglucin, and solvent is deionized water.
3. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, the mass ratio of used tea seed shell powder stock and phloroglucin is 3.5:1~4.5:1 （w/w, g/g）.
4. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, used tea seed shell powder stock and phloroglucin gross mass and the solid-liquid ratio of water are 1:40~1:25（w/
v, g/ml）.
5. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, used template molecule is perfluorooctane sulfonate potassium or perfluorooctane sulfonate.
6. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, the mass ratio of used tea seed shell powder stock and template molecule is：10:1~12.5:1 （w/w, g/g）.
7. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, the isothermal reaction time is 10 ~ 14 h.
8. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, the solvent for being cleaned by ultrasonic the solid product taken out from reactor is deionized water and absolute ethyl alcohol.
9. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, ultrasound-microwave cooperating cleaning solvent is 50% ethanol-water solution, and ultrasound-microwave cooperating cleaning temperature is 55 ~ 65
DEG C, ultrasound-microwave cooperating scavenging period is 25 ~ 40min, at least 3 times.
10. a kind of molecularly imprinted polymer novel preparation method for exempting from function monomer and crosslinking agent according to claim 1, its
It is characterised by, surname extraction solvent is 50% Ethanol-Acetic Acid solution, and the surname extraction time is 72h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711033751.3A CN107597080B (en) | 2017-10-30 | 2017-10-30 | A kind of perfluorooctane sulfonate molecularly imprinted polymer preparation method for exempting from function monomer and crosslinking agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711033751.3A CN107597080B (en) | 2017-10-30 | 2017-10-30 | A kind of perfluorooctane sulfonate molecularly imprinted polymer preparation method for exempting from function monomer and crosslinking agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107597080A true CN107597080A (en) | 2018-01-19 |
| CN107597080B CN107597080B (en) | 2019-10-11 |
Family
ID=61083884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711033751.3A Active CN107597080B (en) | 2017-10-30 | 2017-10-30 | A kind of perfluorooctane sulfonate molecularly imprinted polymer preparation method for exempting from function monomer and crosslinking agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107597080B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116253831A (en) * | 2023-03-23 | 2023-06-13 | 中国科学院青岛生物能源与过程研究所 | Molecular imprinting material for adsorbing phloroglucinol as well as preparation method and application thereof |
| CN116371376A (en) * | 2023-03-22 | 2023-07-04 | 中国科学院青岛生物能源与过程研究所 | Bifunctional phloroglucinol adsorption material and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104671229A (en) * | 2015-01-24 | 2015-06-03 | 南昌航空大学 | Method for preparing carbon microspheres through hydrothermal carbonization of biomass |
| CN105170112A (en) * | 2015-07-27 | 2015-12-23 | 河南城建学院 | Preparation method for magnetic carbon microsphere surface cephalexin molecular imprinted adsorbent material |
| CN105664847A (en) * | 2016-01-13 | 2016-06-15 | 南昌航空大学 | Method for preparing high-specific surface area porous carbon material based on oil tea seed husk and application thereof |
| CN105883805A (en) * | 2016-04-20 | 2016-08-24 | 南昌航空大学 | Preparation method of camellia seed shell based carbon microspheres with high specific surface area |
-
2017
- 2017-10-30 CN CN201711033751.3A patent/CN107597080B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104671229A (en) * | 2015-01-24 | 2015-06-03 | 南昌航空大学 | Method for preparing carbon microspheres through hydrothermal carbonization of biomass |
| CN105170112A (en) * | 2015-07-27 | 2015-12-23 | 河南城建学院 | Preparation method for magnetic carbon microsphere surface cephalexin molecular imprinted adsorbent material |
| CN105664847A (en) * | 2016-01-13 | 2016-06-15 | 南昌航空大学 | Method for preparing high-specific surface area porous carbon material based on oil tea seed husk and application thereof |
| CN105883805A (en) * | 2016-04-20 | 2016-08-24 | 南昌航空大学 | Preparation method of camellia seed shell based carbon microspheres with high specific surface area |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116371376A (en) * | 2023-03-22 | 2023-07-04 | 中国科学院青岛生物能源与过程研究所 | Bifunctional phloroglucinol adsorption material and preparation method and application thereof |
| CN116371376B (en) * | 2023-03-22 | 2024-05-24 | 中国科学院青岛生物能源与过程研究所 | Bifunctional phloroglucinol adsorption material and preparation method and application thereof |
| CN116253831A (en) * | 2023-03-23 | 2023-06-13 | 中国科学院青岛生物能源与过程研究所 | Molecular imprinting material for adsorbing phloroglucinol as well as preparation method and application thereof |
| CN116253831B (en) * | 2023-03-23 | 2024-03-08 | 中国科学院青岛生物能源与过程研究所 | Molecular imprinting material for adsorbing phloroglucinol as well as preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107597080B (en) | 2019-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Masoumi et al. | Removal of metal ions from water using nanohydrogel tragacanth gum-g-polyamidoxime: Isotherm and kinetic study | |
| Al-Aidy et al. | Green adsorbents based on polyacrylic acid-acrylamide grafted starch hydrogels: the new approach for enhanced adsorption of malachite green dye from aqueous solution | |
| Zhou et al. | Adsorption of chromium (VI) from aqueous solutions by cellulose modified with β-CD and quaternary ammonium groups | |
| Pirbazari et al. | Fe3O4–wheat straw: preparation, characterization and its application for methylene blue adsorption | |
| López et al. | Preparation, evaluation and characterization of quercetin-molecularly imprinted polymer for preconcentration and clean-up of catechins | |
| Li et al. | Selective recognition and removal of chlorophenols from aqueous solution using molecularly imprinted polymer prepared by reversible addition-fragmentation chain transfer polymerization | |
| Anirudhan et al. | Removal and recovery of phosphate ions from aqueous solutions by amine functionalized epichlorohydrin-grafted cellulose | |
| Hazer et al. | Use of amidoximated hydrogel for removal and recovery of U (VI) ion from water samples | |
| Xu et al. | Characteristics of cellulosic amine-crosslinked copolymer and its sorption properties for Cr (VI) from aqueous solutions | |
| US20190329221A1 (en) | Synthesis and application of A Nanomaterial for Removal of Patulin | |
| Liang et al. | Ordered macroporous molecularly imprinted polymers prepared by a surface imprinting method and their applications to the direct extraction of flavonoids from Gingko leaves | |
| CA2389904A1 (en) | Droplet polymerization method for synthesis of molecularly imprinted polymers | |
| CN104910313B (en) | Prepare method and the application of Modified with Polar Monomer hypercrosslinked polymeric resin | |
| Zengin et al. | Selective separation and determination of quercetin from red wine by molecularly imprinted nanoparticles coupled with HPLC and ultraviolet detection | |
| Igberase et al. | Application of diethylenetriamine grafted on glyoxal cross-linked chitosan composite for the effective removal of metal ions in batch system | |
| Guc et al. | The molecularly imprinted polymers. influence of monomers on the properties of polymers-a review | |
| Ma et al. | Imprinted β‐cyclodextrin polymers using naringin as template | |
| Wu et al. | Recognition characteristics of molecularly imprinted microspheres for triazine herbicides using hydrogen-bond array strategy and their analytical applications for corn and soil samples | |
| Li et al. | Adsorption of ponceau 4R from aqueous solutions by polyamidoamine–cyclodextrin crosslinked copolymer | |
| Coşkun | Removal of cationic dye from aqueous solution by adsorption onto crosslinked poly (4-vinylpyridine/crotonic acid) and its N-oxide derivative | |
| Anirudhan et al. | Sorptive potential of a cationic exchange resin of carboxyl banana stem for mercury (II) from aqueous solutions | |
| CN101649021B (en) | Preparation method and application of molecular imprinting polymer microspheres for Chlorsulfuron | |
| CN107118294B (en) | A kind of vinylpyridine modification suspended double bond post-crosslinking resin and its preparation method and application | |
| CN107597080B (en) | A kind of perfluorooctane sulfonate molecularly imprinted polymer preparation method for exempting from function monomer and crosslinking agent | |
| Gauthama et al. | Nitrate/Nitrite determination in water and soil samples accompanied by in situ azo dye formation and its removal by superabsorbent cellulose hydrogel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |