CN106432603B - A kind of preparation method and its usage of pollen pini perficial helical mycin molecularly imprinted polymer - Google Patents
A kind of preparation method and its usage of pollen pini perficial helical mycin molecularly imprinted polymer Download PDFInfo
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- CN106432603B CN106432603B CN201610876960.3A CN201610876960A CN106432603B CN 106432603 B CN106432603 B CN 106432603B CN 201610876960 A CN201610876960 A CN 201610876960A CN 106432603 B CN106432603 B CN 106432603B
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- pollen pini
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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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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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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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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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
- 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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- 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
- C08J2335/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J2335/02—Characterised by the use of homopolymers or copolymers of esters
Abstract
The present invention provides a kind of preparation method and its usages of pollen pini perficial helical mycin molecularly imprinted polymer, carry out as steps described below：Spiramvcin and MAA are added in acetonitrile by step 1, and magnetic agitation, obtains mixed liquor A at room temperature；Pollen pini, AIBN and EGDMA are added in acetonitrile by step 2, and mixing obtains mixed liquid B；Mixed liquid B is added in mixed liquor A, mixed liquor C is obtained, N is passed through into mixed liquor C2, magnetic agitation completes polymerisation at 65 DEG C, obtains solid polymer；Step 3 centrifuges the solid polymer in step 2, and after cleaning up, drying obtains pollen pini perficial helical mycin molecularly imprinted polymer, is denoted as PP MIPs.Pollen pini abundance, Hua Yuan used in the present invention be single, stable components, non agricultural chemical residuum, the features such as being free of zoohormone.
Description
Technical field
The present invention relates to a kind of preparation method and its usages of pollen pini perficial helical mycin molecularly imprinted polymer, belong to ring
Border functional material preparing technical field.
Background technology
Spiramvcin (spiramycin, SAY) has powerful vivo bacteria corrosion action, can enhance the phagocytosis of phagocyte
Effect.SAY is macrolide antibiotics, and antibacterial action is poor compared with erythromycin, but it is with longer post antibiotic effect
(PAE), can be used for treating by gram positive bacteria and the microbial ear of certain Grain-negatives, nose, larynx and respiratory tract infection, therefore quilt
It is largely used in animal feeding.Due to as this kind of macrolide antibiotics with antibacterial action of spiramvcin is in aquaculture
In abuse, human body is entered by the enrichment of food chain, individual human body can be caused allergic reaction and drug resistance occur.From 1999
Come, European Union has forbidden spiramvcin as growth accelerator addition in animal feed [71], and China is cultivating spiramvcin
Application in industry has also had specific usage and dosage, but spiramvcin still has residual, moment to endanger in the environment
The health of the mankind.
Pollen pini (pollen pini, PP) is the spermatid of pine tree pistil, is typically manually acquired to it, because
This has flower, and source is single, stable components, non agricultural chemical residuum, the features such as being free of zoohormone.Pollen pini is very early in motherland's medicine
There is record in ancient books, and was the pollen kind uniquely in motherland's medical treasure-house with food, medicine dual-purpose.Pollen pini contains more than 200 kinds
The substances such as active nutritional composition, such as protein, amino acid, minerals and polysaccharide needed for life entity, the diameter of pollen pini
Less than human body cell, it may not be necessary to directly be absorbed by the body by digestive system, and the vital organs of the human body can be sent to, there is supplement
Nutrition improves the healthcare functions such as immunity and face nourishing antidebilitation.Since pollen pini is natural micro materials, derive from a wealth of sources, shape
Looks, which also compare, feature, also contains gas chromatography matter, carries out trace relative in surface of inorganic particles, has by matrix of pollen
Lot of advantages does not have to not only be surface modified, and can trace polymerization reaction directly occur on its surface, simplify experimentation,
Cost is reduced, but also the special imprinted polymer of pattern can be formed
The present invention makes full use of the natural resources, and spiramvcin molecularly imprinted polymer is synthesized on pollen pini surface, to spiral
Mycin has adsorption effect, is that a kind of easy test method prepares imprinted polymer and can carry out the absorption to spiramvcin.
Invention content
The object of the present invention is to provide a kind of preparation methods of pollen pini perficial helical mycin molecularly imprinted polymer, first
First, a certain amount of spiramvcin and methacrylic acid (MAA) are dissolved in acetonitrile, at room temperature magnetic agitation；Next adds pine
The acetonitrile solution of pollen, azodiisobutyronitrile (AIBN) and ethylene glycol dimethacrylate (EGDMA), is passed through N2, and magnetic force stirs
It mixes and completes polymerisation；Step 3 centrifuges solid polymer, after cleaning up, drying.And it by a variety of characterization methods, discloses
The pattern of pollen pini perficial helical mycin molecularly imprinted polymer studies it to spiramvcin in water environment using adsorption experiment
Removal capacity.
The technical solution adopted by the present invention is：
A kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer, carries out as steps described below：
Spiramvcin and MAA are added in acetonitrile by step 1, and magnetic agitation, obtains mixed liquor A at room temperature；
Pollen pini, AIBN and EGDMA are added in acetonitrile by step 2, and mixing obtains mixed liquid B；Mixed liquid B is added
Into mixed liquor A, mixed liquor C is obtained, N is passed through into mixed liquor C2, magnetic agitation completes polymerisation at 65 DEG C, obtains solid
Polymer；
Step 3 centrifuges the solid polymer in step 2, and after cleaning up, it is mould to obtain pollen pini perficial helical for drying
Plain molecularly imprinted polymer, is denoted as PP-MIPs；
Step 4 washes the solid polymer of the obtained drying in step 3 using absolute methanol/glacial acetic acid mixed solution
De- spiramvcin, obtains the non-imprinted polymer in pollen pini surface, is denoted as PP-NIPs.
In step 1, when preparing mixed liquor A, the amount ratio of used spiramvcin, MAA and acetonitrile is 0.084~
8.4g：0.04~4mL：20~2000mL, magnetic agitation time are 4.0~8.0h.
In step 2, when preparing mixed liquid B, the amount ratio of used pollen pini, AIBN, EGDMA and acetonitrile is 0.2~
20g：20~2000mg：0.3~30mL：30~3000mL, when preparing mixed liquor C, acetonitrile in used mixed liquor A with it is mixed
The volume ratio for closing the acetonitrile in liquid B is 20~2000：30~3000；The magnetic agitation time is 4.0~24.0h.
In step 3, the cleaning solution is absolute ethyl alcohol or industrial alcohol, and the drying temperature is 30~70 DEG C.
In step 4, in the absolute methanol/glacial acetic acid mixed solution, the volume ratio of absolute methanol and glacial acetic acid is 9:1
~1:9.
Prepared pollen pini perficial helical mycin molecularly imprinted polymer is for adsorbing spiramvcin.
Advantageous effect：
(1) the pollen pini abundance used in the present invention, Hua Yuan is single, stable components, non agricultural chemical residuum, swash without animal
The features such as plain.
(2) pollen pini perficial helical mycin molecularly imprinted polymer made from have selection recognition capability, thermal stability and
The performances such as recycling rate of waterused height.
(3) preparation method is simple, flow is shorter, easy controlled operation by the present invention, suitable for promoting the use of.
Description of the drawings
Fig. 1 is the SEM figures of PP in embodiment 1 (figure a) and PP-MIPs (figure b~d)；
Fig. 2 is PP (curve a) and the PP-MIPs (hot weight curve of curve b) in embodiment 1；
Fig. 3 is the curve of adsorption kinetics of PP-MIPs and PP-NIPs in embodiment 1；
Fig. 4 is the adsorption isotherm of PP-MIPs and PP-NIPs in embodiment 1；
Fig. 5 is the selective absorption of PP-MIPs and PP-NIPs in embodiment 1；
Specific implementation mode
The invention will be further described With reference to embodiment：
Embodiment 1：
Spiramvcin 0.084g, MAA 0.04mL, is dissolved in 20mL acetonitriles, at room temperature magnetic agitation 4h；It adds later
0.2g pollen pinis, 20mg AIBN, 0.3mL EGDMA, 30mL acetonitriles, are passed through N2, magnetic agitation is for 24 hours at 65 DEG C；Reaction is completed
Afterwards, solid polymer is centrifuged, is used in combination washes of absolute alcohol clean, 50 DEG C dry, is spare.Pollen pini perficial helical mycin molecule
Imprinted polymer (PP-MIPs).Partial polymer is wrapped with filter paper and is put into Soxhlet extractor, with absolute methanol/glacial acetic acid
(V/V)=9:1-1:9 mixed solution washes off spiramvcin molecule, until can't detect spiramvcin molecule in the extracting solution of lower section
Until, 50 DEG C of drying obtain the non-imprinted polymer in pollen pini surface (PP-NIPs).
Table 1 is the specific surface area and average pore diameter of PP, PP-MIPs and PP-NIPs in embodiment 1.It, can be with by comparison
Find out that the specific surface area of PP-MIPs is maximum, the specific surface area of MS-NIPs is minimum.It can be seen that PP, PP-MIPs and PP- in table
NIPs average pore diameters are respectively 28.69nm, 29.34nm and 46.85nm, and illustrate that on pollen pini surface MIPs formed is one
Kind mesoporous polymer, and what NIPs was formed is some random macroporous polymers.
Table 1
In Fig. 1, a is pollen pini original appearance, and each pollen pini is embraced by three spheroid-likes and constituted together, and surface has
Point is coarse.B, c, d are the pattern of pollen pini after trace, it can be seen that have one layer of polymeric package on pollen pini surface.
In Fig. 2, PP and PP-MIPs have certain dehydration at 100 DEG C, and 200-500 DEG C or so has apparent weightlessness.PP
More weightless than PP-MIPs is fast, and the pollen surface after trace has one layer of polymeric package, Nature comparison to stablize, and temperature capability has
Certain raising causes thermal decomposition rate slower.
In Fig. 3, PP-MIPs and PP-NIPs increase the adsorbance of SAY as time increases, finally reach balance.
Maximal absorptive capacities of the PP-MIPs when reaching balance is 21.64mg/g, and maximal absorptive capacities of the MS-NIPs when reaching balance
For 9.83mg/g.
In Fig. 4, a is Thermodynamic Adsorption curves of the PP-MIPs under three kinds of condition of different temperatures, and b, c, d are PP- respectively
Thermodynamic Adsorption matched curves of the MIPs and PP-NIPs at 15 DEG C, 25 DEG C and 35 DEG C.It can be seen that temperature is higher in a, concentration is got over
Greatly, PP-MIPs is bigger to the adsorbance of SAY.B, it can be seen that under three different temperatures in c, d, absorption of the PP-MIPs to SAY
Amount is more than PP-NIPs.
In Fig. 5, the conduct pair of azithromycin (azithromycin, AZM) and erythromycin (erythrocin, EY) solution is chosen
Than allowing PP-MIPs and PP-NIPs under the same conditions respectively to carrying out absorption 12h in the single solution of SAY, AZM and EY, then
Measure the initial concentration of three kinds of antibiotic and the concentration after absorption in mixed solution.Therefrom it can be seen that PP-MIPs and PP-NIPs
Adsorbance to SAY is 19.12mg/g, hence it is evident that is more than the adsorbance to AZM and EY, and selections of the PP-MIPs to AZM and EY
Coefficient is respectively 2.31 and 2.98.
Table 2 is the recycling rate of waterused of PP-MIPs in embodiment 1., by 5 cycling and reutilizations, the repetition profit of PP-MIPs
It is 87.81% with rate, can repeatedly recycle that there is good regenerability.
Table 2
Embodiment 2：
Spiramvcin 0.084g, MAA 0.04mL, is dissolved in 20mL acetonitriles, at room temperature magnetic agitation 4h；It adds later
0.2g pollen pinis, 20mg AIBN, 0.3mL EGDMA, 30mL acetonitriles, are passed through N2, magnetic agitation 4h at 65 DEG C；After the completion of reaction,
Solid polymer is centrifuged, is used in combination washes of absolute alcohol clean, 50 DEG C dry, is spare.Pollen pini perficial helical mycin molecule prints
Mark polymer (PP-MIPs).Partial polymer is wrapped with filter paper and is put into Soxhlet extractor, with absolute methanol/glacial acetic acid (V/
V)=1:9 mixed solution washes off spiramvcin molecule, until it can't detect spiramvcin molecule in the extracting solution of lower section, 50
DEG C drying obtains the non-imprinted polymer in pollen pini surface (PP-NIPs).
Embodiment 3：
Spiramvcin 8.4g, MAA 4mL, is dissolved in 2000mL acetonitriles, at room temperature magnetic agitation 8h；20g is added later
Pollen pini, 2g AIBN, 30mL EGDMA, 30mL acetonitriles, is passed through N2, magnetic agitation is for 24 hours at 65 DEG C；After the completion of reaction, by solid
Polymer centrifuges, and is used in combination washes of absolute alcohol clean, and 50 DEG C dry, is spare.Pollen pini perficial helical mycin molecular engram polymerize
Object (PP-MIPs).Partial polymer is wrapped with filter paper and is put into Soxhlet extractor, with absolute methanol/glacial acetic acid (V/V)=9:
1 mixed solution washes off spiramvcin molecule, until it can't detect spiramvcin molecule in the extracting solution of lower section, 50 DEG C of drying
Obtain the non-imprinted polymer in pollen pini surface (PP-NIPs).
2, in order to clarify the technical solutions and technical objectives of the present invention, with reference to specific implementation example to the present invention do into
One step explanation：
Absorption property evaluation carries out by the following method in specific embodiment in the present invention：It is complete using Staticadsorption experiment
At；The spiramvcin solution of 10mL various concentrations is added in centrifuge tube, the polymer of synthesis, constant temperature is added thereto respectively
It is stood in water-bath, has investigated time of contact, the influence that temperature, concentration adsorb spiramvcin；After absorption reaches saturation, filter membrane mistake
Supernatant liquor is collected in filter, measures spiramvcin molecule not to be adsorbed in test solution at λ=232nm with ultraviolet-visible photometer
Adsorption capacity is calculated in concentration.
Experimental example 1：It is 1 with volume ratio：4 methanol/water solution, compound concentration is respectively 10,20,30,40,50,60,
70, the standard solution of the spiramvcin of 80,90,100mg/L.Measuring this respectively at 232nm with ultraviolet specrophotometer is
The concentration of row solution, and the standard curve of spiramvcin solution is drawn out as shown in Fig. 4-4, and obtain the line of the standard curve
Property equation.
Experimental example 2：：It is 120mg L to take 10ml initial concentrations-1Spiramvcin solution, it is rear be added polymeric material expect from
In heart pipe, test fluid is placed on after standing 12h in 15,25 and 35 DEG C of water-baths, collects supernatant liquor, spiral not to be adsorbed is mould
Plain molecular concentration is measured with ultraviolet-uisible spectrophotometer, and calculates adsorption capacity according to result.
Experimental example 3：It is different spiramvcin solution to take 10ml initial concentrations, and the rear polymeric material that is added expects centrifuge tube
In, test fluid is placed on after standing 12h in 25 DEG C of water-baths, collects supernatant liquor, spiramvcin molecular concentration not to be adsorbed is used
Ultraviolet-uisible spectrophotometer measures, and calculates adsorption capacity according to result.
Experimental example 4：To the experiment that PP-MIPs repeatedly adsorb, elute, adsorb again, and after each elution of measurement
Adsorbance.
Claims (6)
1. a kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer, which is characterized in that as steps described below
It carries out：
Spiramvcin and MAA are added in acetonitrile by step 1, and magnetic agitation, obtains mixed liquor A at room temperature；
Pollen pini, AIBN and EGDMA are added in acetonitrile by step 2, and mixing obtains mixed liquid B；Mixed liquid B is added to mixed
It closes in liquid A, obtains mixed liquor C, N is passed through into mixed liquor C2, magnetic agitation completes polymerisation at 65 DEG C, obtains solid polymerization
Object；
Step 3 centrifuges the solid polymer in step 2, after cleaning up, drying；
The solid polymer of obtained drying in step 3 is eluted spiral shell by step 4 using absolute methanol/glacial acetic acid mixed solution
Revolve mycin.
2. a kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer according to claim 1, special
Sign is, in step 1, when preparing mixed liquor A, the amount ratio of used spiramvcin, MAA and acetonitrile is 0.084~8.4g：
0.04~4mL：20~2000mL, magnetic agitation time are 4.0~8.0h.
3. a kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer according to claim 1, special
Sign is, in step 2, when preparing mixed liquid B, the amount ratio of used pollen pini, AIBN, EGDMA and acetonitrile is 0.2~
20g：20~2000mg：0.3~30mL：30~3000mL, when preparing mixed liquor C, acetonitrile in used mixed liquor A with it is mixed
The volume ratio for closing the acetonitrile in liquid B is 20~2000：30~3000；The magnetic agitation time is 4.0~24.0h.
4. a kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer according to claim 1, special
Sign is, in step 3, the cleaning is cleaned with absolute ethyl alcohol or industrial alcohol, the drying temperature be 30~
70℃。
5. a kind of preparation method of pollen pini perficial helical mycin molecularly imprinted polymer according to claim 1, special
Sign is, in step 4, in the absolute methanol/glacial acetic acid mixed solution, the volume ratio of absolute methanol and glacial acetic acid is 9:1
~1:9.
6. the pollen pini perficial helical mycin molecularly imprinted polymer prepared by the method described in Claims 1 to 5 any one
Purposes, which is characterized in that prepared pollen pini perficial helical mycin molecularly imprinted polymer is for adsorbing spiramvcin.
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Citations (3)
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|---|---|---|---|---|
| CN101507916A (en) * | 2009-02-16 | 2009-08-19 | 西北工业大学 | Preparation method of macrolide antibiotics molecular engram polymer microsphere |
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| CN104829774A (en) * | 2015-04-21 | 2015-08-12 | 华南农业大学 | Azithromycin detection molecular imprinting monolithic micro column and preparation method thereof |
-
2016
- 2016-10-08 CN CN201610876960.3A patent/CN106432603B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101507916A (en) * | 2009-02-16 | 2009-08-19 | 西北工业大学 | Preparation method of macrolide antibiotics molecular engram polymer microsphere |
| CN103816875A (en) * | 2013-10-24 | 2014-05-28 | 江苏大学 | Method for controllably preparing hollow molecularly-imprinted nanorod by using halloysite as template |
| CN104829774A (en) * | 2015-04-21 | 2015-08-12 | 华南农业大学 | Azithromycin detection molecular imprinting monolithic micro column and preparation method thereof |
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| Molecularly imprinted solid-phase extraction for the determination of ten macrolide drugs residues in animal muscles by liquid chromatography–tandem mass spectrometry;Xuqin Song,etal.;《Food Chemistry》;20160321;第208卷;第169-176页 * |
| Synthesis and Characterization of Molecularly Imprinted Poly(methacrylic acid)/Silica Hybrid Composite Materials for Selective Recognition of Lincomycin in Aqueous Media;Yun-Kai Lv,etac.;《Journal of Applied Polymer Science》;20120505;第26卷;第1631-1636页 * |
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