CN105170112B - A kind of preparation method of magnetic carbon microsphere surface cefalexin molecular engram sorbing material - Google Patents
A kind of preparation method of magnetic carbon microsphere surface cefalexin molecular engram sorbing material Download PDFInfo
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Abstract
The present invention relates to a kind of preparation methods of magnetic carbon microsphere surface cefalexin molecular engram sorbing material, the present invention prepares magnetic carbosphere by carbon source of walnut shell, it is used in combination 3 (methacryloxypropyl) propyl trimethoxy silicanes to carry out ethylene functional modification to magnetic carbon microsphere surface, cefalexin (CFX) is used as template molecule, methacrylic acid (MAA) is function monomer, ethylene glycol dimethacrylate (EGDMA) and N, N methylene-bisacrylamides (BIS) are used as crosslinking agent, hexadecane is as perforating agent and organic solvent, it is prepared into magnetic carbon microsphere surface trace adsorbent.Magnetic carbon microsphere surface molecular engram sorbing material prepared by the present invention is at low cost, it is simple to prepare, have to target molecule high identification, highly selective and high score from accumulation ability and adsorption rate it is fast.
Description
Technical field
The present invention relates to a kind of preparation methods of magnetic carbon microsphere surface cefalexin molecular engram sorbing material, belong to ring
Border functional material preparing technical field.
Background technology
Cefalexin antibiotic belongs to Beta-lactam medicine, has strong, penicillin resistant enzyme of has a broad antifungal spectrum, antibacterial action etc.
Advantage.It is usually used in treating septicemia, meningitis endocarditis etc. in livestock-raising.Unreasonable use causes these drugs to exist
It is accumulated in animal derived tissue.After people eats these animal derived foods, there is allergic reaction, or even shock, to human health
It constitutes and seriously threatens.The abuse of high amount of drug also results in the generation of antibody-resistant bacterium, destroys ecological environment.How this is detached
A little medicament residues especially research and develop a kind of quick, sensitive, easy to operate isolation technics and product at urgent problem to be solved
It is very important.
Molecularly imprinted polymer is that have specificity to target molecule (template molecule) by what molecular imprinting technology synthesized
The polymer of identification and selective absorption.Surface molecule print technology is by establishing molecular recognition site in the table in host material
Face, solve well conventional bulk polymerization it is highly cross-linked caused by template molecule cannot completely remove, binding ability is small and matter
The shortcomings of amount transfer is slow, active site embedding is too deep, and the dynamic performance of adsorption-desorption is bad.
In recent years, magnetic field, temperature, light source and pH value can be generated the intelligence of respective action by being prepared using intelligent trace system
Energy material becomes the hot spot of research.Temperature sensitive type trace is prepared with n-isopropyl acrylamide (NIPAm) for temperature sensitive structures alone to gather
It is a kind of typical intelligent trace system to close object material, and the introducing of temperature-sensing property makes Temperature-sensitive Molecular Imprinted Polymers to template point
Son Selective recognition ability can variation with temperature and change.In addition ferriferrous oxide nano-particle is due to stronger superparamagnetic
Property, have been used for the magnetic surface imprinted polymeric materials for preparing nucleocapsid, utilizes the super of ferriferrous oxide nano-particle matrix
Paramagnetism and the effect of the specific adsorption of clad imprinted polymeric materials, magnetic surface imprinted polymeric materials may be implemented in external magnetic field
Target contaminant and mother liquor are rapidly separated by the lower selectivity of auxiliary.However, in preparation process, due to ferriferrous oxide nano
Particle can reunite and the magnetic blotting polymeric material formed can have leakage field.
This method prepares magnetic carbosphere by carbon source of walnut shell, using solvent thermal reaction by ferriferrous oxide nano-particle
It is immobilized on the carbosphere surface of pomelo peel preparation, then trace polymerization process is carried out in its composite material surface, solves well
The problem of leakage field and ferriferrous oxide nano-particle of magnetic blotting polymeric material are reunited.There has been no reports at present for the preparation method
Road.
Invention content
Present invention offer one kind is at low cost, preparation method is simple, there is height to identify to target molecule, highly selective and high score
From accumulation ability and the fast magnetic carbon microsphere surface molecular engram sorbing material and preparation method thereof of adsorption rate, target molecule
For cefalexin molecule.
The technical solution adopted by the present invention is：The present invention prepares magnetic carbosphere by carbon source of walnut shell, and 3- (methyl is used in combination
Acryloyl-oxy) propyl trimethoxy silicane to magnetic carbon microsphere surface carry out ethylene functional modification.It refers in particular to vinyl function
Stabilizer of the magnetic carbosphere of change as Pickering lotions, cefalexin (CFX) are used as template molecule, methacrylic acid
(MAA) it is function monomer, ethylene glycol dimethacrylate (EGDMA) and N, N- methylene-bisacrylamide (BIS), which are used as, to be handed over
Join agent, hexadecane is used as oil phase as perforating agent and organic solvent, mixing.The magnetic carbosphere of vinyl functionalization and 2,2- are even
Nitrogen two (2- methyl-propyls miaow) dihydrochloride (APPH) is added to the water, and water phase is used as after dispersion.Water phase is mixed with oil phase, is surpassed
Sound is prepared into stable Pickering lotions.Then Pickering emulsion polymerizations are carried out, magnetic carbon microsphere surface print is prepared into
Mark adsorbent.Then, template molecule, 50-60 DEG C of vacuum drying are washed away for the mixed liquor of 9: 1 (V/V) with methanol and acetic acid.Most
Afterwards, magnetic carbon microsphere surface trace adsorbent for cefalexin in water environment Selective recognition with detach.
The method that emulsion polymerization prepares magnetic carbon microsphere surface trace adsorbent, carries out as steps described below：
(1) preparation of magnetic carbosphere
It chooses walnut shell and dries 18h at a temperature of 115 DEG C, the walnut shell powder of above-mentioned drying is broken to grain size in 2.0-
4.0mm or so obtains feed particles.By above-mentioned walnut shell particle by the hydrochloric acid of 3.0mol/L, flow back 10- at 60-70 DEG C
15h is washed with distilled water multiple value neutrality, is placed at 50-60 DEG C that drying to constant weight, obtains acid activation walnut shell particle.
By the acid activation walnut shell particle and FeCl of above-mentioned preparation3.6H2O, sodium acetate is according to acid activation walnut capsomere:
FeCl3.6H2O: sodium acetate is (0.6-1.0): (0.3-0.5): the ratio of (1.5-2.0) (g/g/g) is dissolved in ethylene glycol, second two
The addition of alcohol is according to acid activation walnut capsomere: ethylene glycol=1.0: 30-60min, mixing is stirred by ultrasonic in (90-100) (g/ml)
Uniformly, then to polyethylene glycol is added in above-mentioned mixed liquor, the addition of polyethylene glycol is according to acid activation walnut capsomere: poly- second two
Alcohol=1.0: (1.5-1.8) (g/g), magnetic agitation 30-60min, after stirring, mixed liquor is transferred to water-bath kettle Program
Heating, 3-5h rise to 150-200 DEG C, this thermotonus 8.0-10h, dry after product ethyl alcohol and distillation water washing are multiple
To constant weight, magnetic carbosphere is obtained.
(2) prepared by functional magnetic carbosphere
According to magnetic carbosphere: 3- (methacryloxypropyl) propyl trimethoxy silicane: toluene amount ratio is 1.0: (3.0-
4.0): (90-100) (g/g/g) is added in three-necked flask, the 300-400rpm mechanical agitations 20-24h at 70-90 DEG C, largely
Toluene washing to remove 3- (methacryloxypropyl) propyl trimethoxy silicane for not participating in reaction, 60 DEG C of vacuum drying to get
To the magnetic carbosphere of vinyl functionalization.
(3) emulsion polymerization prepares magnetic carbon microsphere surface trace adsorbent
By cefalexin, methacrylic acid (MAA) and hexadecane according to 1: (5-7): the ratio of (5: 8) (mmol/mmol/m1)
Example mixes, and is sealed after ultrasonic 10-15min, pre-assembled 10-14h.Then in above-mentioned mixed liquor according to molar ratio cephalo ammonia
Benzyl: ethylene glycol dimethacrylate (EGDMA): N, N- methylene-bisacrylamide (BIS) are 1: (20-30): (1.5-1.8)
(mmol/mmol/mmol) ethylene glycol dimethacrylate (EGDMA) and N, N- methylene-bisacrylamide is added in ratio
(BIS)；Then by the magnetic carbosphere of above-mentioned functionalization, (the 2- methyl-propyls miaow) dihydrochloride (APPH) of 2,2- azos two and water
Mixing, wherein control cefalexin and functionalization magnetic carbosphere ratio be 1: (0.8-1.2) (mmol/g), cefalexin and
The ratio of water is 1: (50-100) (mol/ml), cefalexin and 2,2- azos two (2- methyl-propyls miaow) dihydrochloride (APPH)
Than being 1: (0.05-0.07) (mol/g), ultrasonic 20-30min are uniformly dispersed, water phase is mixed with oil phase, ultrasound 5- in ice bath
10min is prepared into stable Pickering lotions.Then, after the Pickering lotions of preparation lead to nitrogen 10-20min,
18-24h is kept at 60-70 DEG C.Products therefrom absolute ethyl alcohol and distilled water repeatedly wash, and it is 9: 1 finally to use methanol and acetic acid
(V/V) mixed liquor washes away template molecule, last 50-60 DEG C of vacuum drying.The system of the non-trace adsorbent of magnetic carbon microsphere surface
Preparation Method is same as above, and is only not added with cefalexin in the process.
Description of the drawings
The isollaothermic chart of Fig. 1 magnetic carbons microsphere surface trace adsorbent and non-trace adsorbent absorption cefalexin (CFX).
It can be seen that adsorption capacity increases therewith with the raising of concentration.Trace adsorbent holds the absorption of cefalexin (CFX)
Amount, to cefalexin (CFX) adsorption capacity, shows good specific recognition performance, illustrates to print much larger than non-trace adsorbent
There is the active site to match with cefalexin (CFX) molecule in mark adsorbent.
The dynamics figure of Fig. 2 magnetic carbons microsphere surface trace adsorbent and non-trace adsorbent absorption cefalexin (CFX).
It can be seen that originally, with the increase of adsorption time, adsorption capacity increases sharply, is adsorbed after 30min and reach balance, whole
In a Longer absorption times, trace adsorbent is more than non-trace adsorbent to the adsorption capacity of cefalexin and is adsorbed to cefalexin
Capacity shows good absorption property.
Fig. 3 magnetic carbons microsphere surface trace adsorbent and non-trace adsorbent absorption cefalexin (CFX) and other three
The experiment of kind competition antibiotic, the results showed that, trace adsorbent is shown detaches richness to the preferable Selective recognition of cefalexin
Collection ability.
Specific implementation mode
With reference to specific implementation example, the invention will be further described.
Embodiment 1
(1) preparation of magnetic carbosphere
It chooses walnut shell and dries 18h at a temperature of 115 DEG C, the walnut shell powder of above-mentioned drying is broken to grain size in 2.0-
4.0mm or so obtains feed particles.By above-mentioned walnut shell particle by the hydrochloric acid of 3.0mol/L, flow back 12h at 70 DEG C, uses
Distillation water washing is repeatedly worth neutrality, is placed at 60 DEG C that drying to constant weight, obtains acid activation walnut shell particle.
By the acid activation walnut shell particle and FeCl of above-mentioned preparation3.6H2O, sodium acetate is according to acid activation walnut capsomere:
FeCl3.6H2The addition of O: the ratio of sodium acetate 1.0: 0.5: 2.0 (g/g/g) is dissolved in ethylene glycol, ethylene glycol are living according to acid
Change walnut capsomere: ethylene glycol=1.0: 100 (g/ml), 30min is stirred by ultrasonic, be uniformly mixed, adds then in above-mentioned mixed liquor
Enter polyethylene glycol, the addition of polyethylene glycol is according to acid activation walnut capsomere: polyethylene glycol=1.0: 1.6 (g/g), magnetic agitation
60min, after stirring, mixed liquor is transferred to the heating of water-bath kettle Program, and 4h rises to 200 DEG C, this thermotonus 10h,
It is dry to constant weight after product ethyl alcohol and distillation water washing are multiple, obtain magnetic carbosphere.
(2) prepared by functional magnetic carbosphere
According to magnetic carbosphere: 3- (methacryloxypropyl) propyl trimethoxy silicane: toluene amount ratio is 1.0: 3.0:
100 (g/g/g) are added in three-necked flask, and 400rpm mechanical agitations for 24 hours, with removing do not participated in by a large amount of toluene washing at 80 DEG C
3- (methacryloxypropyl) propyl trimethoxy silicane of reaction, 60 DEG C of vacuum drying are to get to the magnetism of vinyl functionalization
Carbosphere.
(3) emulsion polymerization prepares magnetic carbon microsphere surface trace adsorbent
Cefalexin, methacrylic acid (MAA) and hexadecane are mixed according to the ratio of 1: 5: 8 (mmol/mmol/m1),
It is sealed after ultrasonic 15min, pre-assembled 12h.Then in above-mentioned mixed liquor according to molar ratio cefalexin: glycol dinitrate
Base acrylate (EGDMA): N, N- methylene-bisacrylamide (BIS) are that the ratio of 1: 20: 1.5 (mmol/mmol/mmol) adds
Enter ethylene glycol dimethacrylate (EGDMA) and N, N- methylene-bisacrylamide (BIS)；Then by the magnetic of above-mentioned functionalization
Property carbosphere, (the 2- methyl-propyls miaow) dihydrochloride (APPH) of 2,2- azos two and water mixing, wherein control cefalexin and work(
The magnetic carbosphere ratio of energyization is 1: 1.0 (mmol/g), and the ratio of cefalexin and water is 1: 100 (mol/ml), cephalo ammonia
Benzyl and 2, for 2- azos two (2- methyl-propyls miaow) dihydrochloride (APPH) than being 1: 0.05 (mol/g), ultrasonic 30min dispersions are equal
It is even, water phase is mixed with oil phase, ultrasound 10min in ice bath is prepared into stable Pickering lotions.Then, preparation
After Pickering lotions lead to nitrogen 20min, kept for 24 hours at 60 DEG C.Products therefrom absolute ethyl alcohol and distilled water repeatedly wash,
Finally template molecule, last 60 DEG C of vacuum drying are washed away for the mixed liquor of 9: 1 (V/V) with methanol and acetic acid.Magnetic carbosphere table
The preparation method of the non-trace adsorbent in face is same as above, and is only not added with cefalexin in the process.
Absorption property evaluation carries out by the following method in specific embodiment in the present invention：It has been tested using Static Adsorption
At.25ml cefalexin solution is added in centrifuge tube, 10mg magnetic carbon microsphere surface trace adsorbents are added thereto respectively
It is static in water bath with thermostatic control with non-trace adsorbent, initial concentration solution, time of contact are investigated to the shadow of cefalexin adsorbance
It rings.Up to after balancing, supernatant is separated and collected with Nd-Fe-B permanent magnets for absorption, cefalexin not to be adsorbed point in solution
Sub- concentration is measured with ultraviolet-uisible spectrophotometer, calculates to obtain adsorption capacity (q)
Q=[(C0-Ce)V]/W
C0(μm ol/L) and CeConcentration when (μm ol/L) is respectively the initial concentration and balance of cefalexin, V (mL) and W
(mg) be respectively liquor capacity and adsorbent dosage.
Embodiment 2
It is respectively the cephalo ammonia of 5,10,20,30,50,60,80,100,150,200,300 μm of ol/L to take 25ml initial concentrations
Benzyl solution is added in centrifuge tube, is separately added into 10mg magnetic carbons microsphere surface trace adsorbent and non-trace adsorbent, will be surveyed
Examination solution, which is placed in 25 DEG C of water-baths, stands 24.0h, and supernatant is separated and collected with Nd-Fe-B permanent magnets, head not to be adsorbed
Cefalexin molecular concentration is measured with ultraviolet-uisible spectrophotometer, calculates adsorption capacity, shows trace adsorbent shown in Fig. 1
Saturated adsorption capacity be 52.35umol/g be higher than non-trace sorbing material 19.36umol/g, it was demonstrated that trace sorbing material is deposited
In a large amount of trace hole, good imprinting effect is shown.
Embodiment 3
It is that the cefalexin solution of 150 μm of ol/L is added in centrifuge tube to take 25ml initial concentrations, and 10mg magnetic carbons are added
Microsphere surface trace adsorbent and non-trace adsorbent, test solution is placed in 25 DEG C of water-baths and stands 2 respectively, 5,10,20,
30,45,60,90,120 and 150min, after the completion of standing, supernatant is separated and collected with Nd-Fe-B permanent magnets, not to be adsorbed
Cefalexin molecular concentration is measured with ultraviolet-uisible spectrophotometer, calculates adsorption capacity, as can be known from Fig. 2, originally, with
The increase of adsorption time, adsorption capacity increase sharply, and are adsorbed after 30min and reach balance, magnetic in entire Longer absorption times
The surface imprinted adsorbent of carbosphere is more than non-trace adsorbent to the adsorption capacity of cefalexin molecule and is inhaled to cefalexin molecule
Attached capacity shows good absorption property.
Embodiment 4
Select tetracycline (TC), sulphadiazine (SD) and ampicillin (AMP) for competitive Adsorption antibiotic.It prepares respectively
Solution concentration is the above-mentioned three kinds of antibiotic of 100 μm of ol/L.It takes the solution that 25ml has been configured to be added in centrifuge tube, is separately added into 10mg
Test solution is placed in 25 DEG C of water-baths and stands 12.0h by magnetic carbon microsphere surface trace adsorbent and non-trace adsorbent.It inhales
After attached saturation, supernatant is separated and collected with Nd-Fe-B permanent magnets, and various competitive Adsorption antibiotic concentrations not to be adsorbed are purple
Outer visible spectrophotometer measures, and adsorption capacity is calculated, from figure 3, it can be seen that trace adsorbent has significant spy to CFX
Opposite sex identification, adsorption capacity are apparently higher than other antibiotic.
Claims (7)
1. a kind of preparation method of magnetic carbon microsphere surface cefalexin molecular engram sorbing material, it is characterised in that according to following
Step carries out：
(1) preparation of magnetic carbosphere
It chooses walnut shell and dries 18h at a temperature of 115 DEG C, the walnut shell powder of above-mentioned drying is broken to grain size in 2.0-4.0mm
Left and right obtains feed particles, and by above-mentioned walnut shell particle by the hydrochloric acid of 3.0mol/L, flow back 10-15h at 60-70 DEG C, uses
Water washing is distilled repeatedly to neutral, is placed at 50-60 DEG C that drying to constant weight, obtains acid activation walnut shell particle；
By the acid activation walnut shell particle and FeCl of above-mentioned preparation3·6H2O, sodium acetate is dissolved in ethylene glycol, and 30- is stirred by ultrasonic
60min is uniformly mixed, and then to polyethylene glycol is added in above-mentioned mixed liquor, magnetic agitation 30-60min after stirring, is mixed
It closes liquid and is transferred to the heating of water-bath kettle Program, 3-5h rises to 150-200 DEG C, this thermotonus 8.0-10h, product ethyl alcohol
With distillation water washing it is multiple after, it is dry to constant weight, obtain magnetic carbosphere；
(2) prepared by functional magnetic carbosphere
The mixed liquor of the magnetic carbosphere of above-mentioned preparation, 3- (methacryloxypropyl) propyl trimethoxy silicanes and toluene is in proportion
It is added in three-necked flask, the 300-400rpm mechanical agitations 20-24h at 70-90 DEG C, a large amount of toluene washing is not participated in removing
3- (methacryloxypropyl) propyl trimethoxy silicane of reaction, 60 DEG C of vacuum drying are to get to the magnetism of vinyl functionalization
Carbosphere；
(3) emulsion polymerization prepares magnetic carbon microsphere surface trace adsorbent
Cefalexin, methacrylic acid (MAA) and hexadecane mix in proportion, are sealed after ultrasonic 10-15min, pre-assembled
10-14h is added above-mentioned then by ethylene glycol dimethacrylate (EGDMA) and N, N- methylene-bisacrylamide (BIS)
In pre-polymer solution, then by the magnetic carbosphere of above-mentioned functionalization, 2,2- azos two (2- methyl-propyls miaow) dihydrochloride
(APPH) it is uniformly dispersed with water mixing, ultrasonic 20-30min, water phase is mixed with oil phase, ultrasound 5-10min, is made in ice bath
For at stable Pickering lotions, then, after the logical nitrogen 10-20min of Pickering lotions of preparation, protected at 60-70 DEG C
18-24h is held, products therefrom absolute ethyl alcohol and distilled water repeatedly wash, and finally use methanol and acetic acid for the mixing of 9: 1 (V/V)
Liquid washes away template molecule, last 50-60 DEG C of vacuum drying；Acid activation walnut capsomere in step (1): FeCl3·6H2O: sodium acetate
For (0.6-1.0): (0.3-0.5): (1.5-2.0) (g/g/g), the addition of ethylene glycol is according to acid activation walnut capsomere: second two
Alcohol=1.0: (90-100) (g/ml), the addition of polyethylene glycol is according to acid activation walnut capsomere: polyethylene glycol=1.0: (1.5-
1.8)(g/g)；Magnetic carbosphere in step (2): 3- (methacryloxypropyl) propyl trimethoxy silicane: toluene mass ratio is
1.0∶(3.0-4.0)∶(90-100)(g/g/g)；Cefalexin, methacrylic acid (MAA) described in step (3) and hexadecane
Ratio 1: (5-7): (5: 8) (mmol/mmol/ml).
2. a kind of preparation side of magnetic carbon microsphere surface cefalexin molecular engram sorbing material according to claim 1
Method, it is characterised in that the cefalexin, ethylene glycol dimethacrylate (EGDMA) described in step (3) and N, N- methylene
Bisacrylamide (BIS) ratio is 1: (20-30): (1.5-1.8) (mmol/mmol/mmol).
3. a kind of preparation side of magnetic carbon microsphere surface cefalexin molecular engram sorbing material according to claim 1
Method, it is characterised in that the magnetic carbosphere ratio of cefalexin and functionalization described in step (3) is 1: (0.8-1.2)
(mmol/g)。
4. a kind of preparation side of magnetic carbon microsphere surface cefalexin molecular engram sorbing material according to claim 1
Method, it is characterised in that the ratio of cefalexin and water described in step (3) is 1: (50-100) (mol/ml).
5. a kind of preparation side of magnetic carbon microsphere surface cefalexin molecular engram sorbing material according to claim 1
Method, it is characterised in that the cefalexin and 2 described in step (3), 2- azos two (2- methyl-propyls miaow) dihydrochloride (APPH)
Than being 1: (0.05-0.07) (mol/g).
6. the magnetic carbon microsphere surface cefalexin molecular engram being prepared according to the preparation method of any one of claim 1-5
Sorbing material.
7. magnetic carbon microsphere surface cefalexin molecular engram sorbing material according to claim 6 is for cefalexin molecule
Identification and enrichment.
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| CN105879882A (en) * | 2016-03-15 | 2016-08-24 | 宁波江东波莫纳电子科技有限公司 | Method for preparing easily dispersed magnetic biomass carbon-based solid acid catalyst |
| CN107597080B (en) * | 2017-10-30 | 2019-10-11 | 南昌航空大学 | A kind of perfluorooctane sulfonate molecularly imprinted polymer preparation method for exempting from function monomer and crosslinking agent |
| CN110330590B (en) * | 2019-07-01 | 2021-07-13 | 河南城建学院 | Magnetic hierarchical pore chestnut shell carbon sphere-based surface imprinting material and preparation method and application thereof |
| CN110252263A (en) * | 2019-07-01 | 2019-09-20 | 河南城建学院 | A kind of peanut shell base magnetism multi-stage porous carbon surface imprinted material and its preparation method and application |
| CN110252262A (en) * | 2019-07-01 | 2019-09-20 | 河南城建学院 | A kind of magnetism corncob multi-stage porous carbon microsphere surface imprinted material and its preparation method and application |
| CN110339823A (en) * | 2019-07-01 | 2019-10-18 | 河南城建学院 | A kind of Eichhornia crassipes base magnetism multi-stage porous carbon surface imprinted material and its preparation method and application |
| CN110252264A (en) * | 2019-07-01 | 2019-09-20 | 河南城建学院 | A kind of cocoanut shell biomass carbon microsphere surface imprinted material and its preparation method and application |
| CN113061216A (en) * | 2021-03-10 | 2021-07-02 | 大理州质量技术监督综合检测中心 | Magnetic molecularly imprinted polymer for simultaneously extracting multiple cephalosporin antibiotics and preparation method and application thereof |
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