CN106866863A - A kind of preparation method of porous polymer microballoon anion filler - Google Patents
A kind of preparation method of porous polymer microballoon anion filler Download PDFInfo
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- CN106866863A CN106866863A CN201510924619.6A CN201510924619A CN106866863A CN 106866863 A CN106866863 A CN 106866863A CN 201510924619 A CN201510924619 A CN 201510924619A CN 106866863 A CN106866863 A CN 106866863A
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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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
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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
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- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/44—Materials comprising a mixture of organic materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
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Abstract
The invention discloses a kind of preparation method of porous polymer microballoon anion filler, chloromethyl is first introduced, ethylenediamine is then introduced in microsphere surface by surface grafting method, form anion filler.The present invention is substrate by using monodispersed polystyrene/divinylbenzene microballoon, and chloromethyl functional group is introduced by being reacted with chloromethyl ether, then forms anion filler by surface grafting method and reacting ethylenediamine.Feature of the present invention is that gained anion filler Microsphere Size is controllable, and surface functional group species is controllable, and technological operation is simple and easy to do, low raw-material cost, easy to operate, be easy to industrializing implementation.
Description
Technical field
Filled out the present invention relates to anion packing technique field, more particularly to a kind of porous polymer microballoon anion
The preparation method of material.
Background technology
With developing rapidly for economic globalization, food trade constantly expands, in order to avoid " Sanlu " milk powder,
The generation again of ditch oil and clenbuterol hydrochloride tragedy, the research for strengthening food inspection is just particularly important.With
The detection project of organic chemistry hazardous material is more and more in food, only relies on existing detection technique and detection efficiency,
The demand that hundreds of kinds of organic chemistry hazardous materials are detected simultaneously, organic chemistry material residue detection in food cannot be tackled
The main source of difficult point, step of most losing time and error all concentrate on the pretreatment stage of sample, because
This, sets up and detects that the sample-pretreating method for matching is rapid screening analysis food with quick, high-throughout
In organic chemistry hazardous material key, be also greatest problem and challenge that food analysis worker faces.It is poly-
Compound magnetic Nano microsphere because with good skin effect, particle diameter is small, specific surface area is high, toxic and side effect is small,
The properties such as superparamagnetism, have been widely used in bio-chemistry separation, food inspection, catalysis, medical science, environment
Deng field, but Nano microsphere prepared by conventional method, because particle diameter is too small, specific surface area is quite big, spherical
Functional group number is more on surface, and the property of unsaturated bond and functional group is again relatively more active, has and tends to hair
The raw phenomenon reunited, so using limited.
Experiment shows to carry out surface modification by nano-particle, and by the way that combined polymerization or surface be modified etc., means make
Its surface can reduce its surface energy with functional groups such as-COOH ,-OH ,-NH, adjust its biocompatibility
And response characteristic, so as to obtain the nanoparticle of soluble or good dispersion, such as (Du Peng flies carboxylated to document
The preparation of Fe3O4 magnetic Nano microspheres and sign material Leaders B：Research piece .2014,28 (2):42-45)
Nanometer Fe_3O_4 is prepared using chemical coprecipitation, Coated with Oleic Acid, potassium permanganate oxidation, modification obtains carboxyl
The hydrophilic magnetic nano-complex particle of functionalization, consulting literatures also found the made standby immune magnetic of existing method
Being confined to microballoon more detect food in microorganism, active material and GM food detection etc. aspect, such as
Document (the progress for preparing and its being applied to Microbiological detection of foods of Zhang Xiaoqiang immune magnetic microspheres
Work is in progress, and 2009,28 (8)：1427-1430；The such as Zhao Weidong magnetic microspheres are examined in plant-derived GM food
Application food research and developments in survey, 2012,33 (6)：128-130).
Above method has following deficiency：Particle diameter is narrow, and size controlling means are unreliable；Particle diameter distribution is uneven
One；Swelling process microballoon is broken, unstable；Cumbersome step is more.
The content of the invention
The present invention combines polymerization while swelling and prepares porous polymer microsphere, as substrate by coming to the surface
Learn modification and introduce functional group, prepare porous polymer microballoon anion filler.The present invention relates to polystyrene/
Divinylbenzene microspheres are substrate, and ethylenediamine group is re-introduced into by surface chloromethylation, and synthetic anionic is filled out
The method of material.
A kind of preparation method of porous polymer microballoon anion filler, is included in polystyrene/divinylbenzene
Chloromethyl is introduced on microballoon, functional group is then introduced in microsphere surface by surface grafting method, form cloudy
Ion filler.
Used as preferred scheme of the invention, above-mentioned chloromethyl reacts introducing by with chloromethyl ether.
Used as preferred scheme of the invention, above-mentioned functions group is ethylenediamine group.
Used as preferred scheme of the invention, the particle diameter of above-mentioned anion filler is 1 μm -20 μm.
Used as preferred scheme of the invention, the above method includes：Use polystyrene/divinylbenzene microballoon for
Substrate, chloromethylation condition is provided with methyl ether, and function of surface modification is carried out with reacting ethylenediamine, formed it is cloudy from
Sub- filler.
Used as preferred scheme of the invention, the reaction system in the above method includes oil phase and water phase, the oil
Mutually include toluene and chloroform；The water mutually includes methyl alcohol, water and acetone soln.
Used as preferred scheme of the invention, the above method includes：Chloromethylation is first carried out in toluene solution,
The ethylenediamine group in modification in chloroform soln, forms the porous polymer microballoon anion filler again.
Used as preferred scheme of the invention, the above method includes：
Polystyrene/divinylbenzene microballoon is dissolved in toluene, swelling 3h is stirred at room temperature, be cooled to room temperature,
Add chloromethyl ether and stannic chloride, continue to be stirred at room temperature reaction 3h, add deionized water terminating reaction, with hydrochloric acid,
Tetrahydrofuran, acetone cleaning, it is standby；
The chloromethylation microballoon for obtaining, adds in chloroform, adds ethylenediamine, is heated with stirring to 150 DEG C,
Reaction 6h, is down to room temperature, with acetone, water, methyl alcohol process, vacuum drying；
The ethylenediamine microballoon for obtaining adds triethylamine, acetic anhydride, DMAP in toluene,
It is stirred overnight at room temperature, is processed with methyl alcohol, water, acetone, it is micro- that vacuum drying obtains the porous polymer
Ball anion filler.
The present invention innovates formula and technique using development in laboratory, is obtained using emulsion polymerization and dispersion copolymerization method
It is polymerized while swelling and seed and then prepares monodispersed polymer microsphere, function is carried out by polymer microballoon
Modification, introduces to specific function group so that strong cation, weak cation, strong anion, weak anionic is obtained
Deng with surface functional groups density and larger adsorption capacity polymer microsphere filler higher.This structure
Porous crosslinked polystyrene microspherulite diameter is uniform and size is controllable, and adsorption capacity and sample capacity are higher, is applicable
The pH scopes of sample are wide, during as chromatographic column filler, can effectively reduce post pressure, and internal pore passage structure makes
Active area between tested substance and microballoon further increases, and increases retention time, can be more preferable
Realize that material is separated, have wide practical use in terms of the extraction, enrichment and purifying in compound.
Specifically, Binding experiment room of the present invention advantage, prepares polymer microballoon, and table is carried out by chemical reaction
Face is modified, and polystyrene/divinylbenzene microballoon reacts introducing chloromethyl functional group by with chloromethyl ether, then leads to
Cross the method for surface grafting and introduce special functional group in microsphere surface, such as formed with reacting ethylenediamine the moon from
Sub- filler, makes its uniform particle diameter and controllable, separative efficiency is improved, while relevant apparatus can be combined, makes food
There is fashionable dress post to simplify for committed step and method in organic chemistry material residue detection, and repeatability is high, and quality is steady
Fixed, post pressure is small, and target analytes are adsorbed uniformly in fixing phase, and wash-out is concentrated, and solvent load is few, sample
The series of advantages such as out time is short, makes it possible quick, high-throughout food analysis, the product
Effectively trace analysis thing can also be separated with interfering component, reduce sample pretreatment process, it is low dense processing
Degree and trace analysis thing have unique advantage.
Brief description of the drawings
Fig. 1 is the preparation reaction mechanism of porous polymer microballoon anion filler of the invention；
Fig. 2 is the process schematic representation of the preparation method of porous polymer microballoon anion filler of the invention；
Fig. 3 is the electron microscope of the polymer microballoon of various pore sizes prepared by the embodiment of the present invention 1.
Specific embodiment
Cannot be highly homogeneous present invention aim to address existing polymer microsphere anion filler microspherulite diameter,
Not easy-regulating, it is impossible to the problem of industrialized production, there is provided one kind prepare monodisperse porous polymer microsphere it is cloudy from
The method of sub- filler.
Advantages of the present invention：Porous polymer microballoon single dispersing is good, size tunable；Tested by simple regulation and control
Parameter can control microballoon aperture and pore distribution；Surface-functionalized modification is simple to operate；Low raw-material cost,
Technological operation is easy, it is easy to industrializing implementation.
It is substrate using polystyrene/divinylbenzene microballoon that the present invention is developed a kind of first, carries out chloromethyl
Change again by surface-functionalized modification introduce ethylenediamine group synthesize a kind of monodisperse porous polymer microsphere it is cloudy from
The new method of sub- filler.
Fig. 1 shows the preparation reaction mechanism of porous polymer microballoon anion filler of the invention, using poly-
Styrene/divinylbenzene microspheres are substrate, carry out chloromethylation, then introduce second by surface-functionalized modification
Diamine groups.
Fig. 2 shows the process schematic representation of the preparation method of porous polymer microballoon anion filler of the invention,
It is polymerized by while swelling, the less larger homogeneous seed of Seed Development.
Porous polymer microballoon used in the present invention has one in toluene, chloroform and dichloromethane
Fixed dispersiveness.
The present invention provide with porous polymer microballoon as substrate, after chemical reaction surface is modified chloromethylation,
The preparation method of the synthesizing porous polymer microsphere anion filler of surface grafting ethylenediamine group again.
Process conditions：How empty polymer microsphere is scattered in toluene solution, polystyrene/divinylbenzene is micro-
Ball concentration in toluene is 0.05~0.25g/mL, and swelling, addition chloromethyl ether and stannic chloride, chloromethane is stirred at room temperature
Ether is 5~15 with the volume ratio of stannic chloride:1, after continuing to react 3, stop reaction, wash drying for standby.
Chloromethylation microballoon is scattered in chloroform, the concentration of chloromethylation microballoon chloroform dispersion liquid
It is 0.025~0.1g/ml, adds ethylenediamine, agitating heating reaction 6h to wash drying for standby.
Above-mentioned microballoon is scattered in toluene, addition triethylamine, acetic anhydride, DMAP, triethylamine,
The proportioning of acetic anhydride, DMAP, by weight 4:1:10~30, it is stirred overnight, wash, very
Empty dry monodisperse porous polymer microsphere anion filler.
Embodiment 1
5g polystyrene/divinylbenzene microballoons are dissolved in 50ml toluene, swelling 3h is stirred at room temperature, it is cold
But to room temperature, 20ml chloromethyl ethers and 2ml stannic chlorides are added, continue to be stirred at room temperature reaction 3h, addition go from
Sub- water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 5.4g is taken, is added in 108ml chloroforms, add 40ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 2.4g is taken in 120ml toluene, add 6g triethylamines, 1.5g acetic anhydrides,
15g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Fig. 3 shows the electron microscope of the polymer microballoon of various pore sizes manufactured in the present embodiment.
Embodiment 2
5g polystyrene/divinylbenzene microballoons are dissolved in 100ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 20ml chloromethyl ethers and 4ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, added
Deionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 5.4g is taken, is added in 216ml chloroforms, add 40ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 2.4g is taken in 120ml toluene, add 6g triethylamines, 1.5g acetic anhydrides,
30g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Embodiment 3
5g polystyrene/divinylbenzene microballoons are dissolved in 100ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 30ml chloromethyl ethers and 2ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, addition is gone
Ionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 5.4g is taken, is added in 54ml chloroforms, add 40ml ethylenediamines, stirred
Mix and be heated to 150 DEG C, react 6h.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 2.4g is taken in 100ml toluene, add 6g triethylamines, 1.5g acetic anhydrides,
45g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Embodiment 4
10g polystyrene/divinylbenzene microballoons are dissolved in 40ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 60ml chloromethyl ethers and 4ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, addition is gone
Ionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 10.8g is taken, is added in 216ml chloroforms, add 80ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 4.8g is taken in 240ml toluene, add 12g triethylamines, 3g acetic anhydrides,
30g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Embodiment 5
10g polystyrene/divinylbenzene microballoons are dissolved in 60ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 40ml chloromethyl ethers and 4ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, addition is gone
Ionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 10.8g is taken, is added in 216ml chloroforms, add 80ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 4.8g is taken in 96ml toluene, add 12g triethylamines, 3g acetic anhydrides,
45g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Embodiment 6
10g polystyrene/divinylbenzene microballoons are dissolved in 80ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 30ml chloromethyl ethers and 4ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, addition is gone
Ionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 10.8g is taken, is added in 144ml chloroforms, add 80ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 4.8g is taken in 64ml toluene, add 12g triethylamines, 3g acetic anhydrides,
45g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Embodiment 7
10g polystyrene/divinylbenzene microballoons are dissolved in 80ml toluene, swelling 3h are stirred at room temperature,
Room temperature is cooled to, 20ml chloromethyl ethers and 4ml stannic chlorides is added, continues that reaction 3h is stirred at room temperature, addition is gone
Ionized water terminating reaction, is cleaned with hydrochloric acid, tetrahydrofuran, acetone, standby.
Above-mentioned chloromethylation microballoon 10.8g is taken, is added in 108ml chloroforms, add 80ml ethylenediamines,
150 DEG C are heated with stirring to, 6h is reacted.Room temperature is down to, with acetone, water, methyl alcohol process, vacuum drying.
Above-mentioned ethylenediamine microballoon 4.8g is taken in 48ml toluene, add 12g triethylamines, 3g acetic anhydrides,
60g4- dimethylamino naphthyridines, are stirred overnight at room temperature.Processed with methyl alcohol, water, acetone, be vacuum dried.
Above content is to combine specific embodiment further description made for the present invention, it is impossible to recognized
Fixed specific implementation of the invention is confined to these explanations.For the ordinary skill of the technical field of the invention
For personnel, without departing from the inventive concept of the premise, some simple deduction or replace can also be made,
Protection scope of the present invention should be all considered as belonging to.
Claims (8)
1. a kind of preparation method of porous polymer microballoon anion filler, it is characterized in that, methods described is included in and chloromethyl is introduced on polystyrene/divinylbenzene microballoon, then introduces functional group in microsphere surface by surface grafting method, forms anion filler.
2. preparation method according to claim 1, it is characterised in that the chloromethyl is introduced by being reacted with chloromethyl ether.
3. preparation method according to claim 1, it is characterised in that the functional group is ethylenediamine group.
4. preparation method according to claim 1, it is characterised in that the particle diameter of the anion filler is 1 μm -20 μm.
5. preparation method according to claim 1, it is characterised in that methods described includes：It is substrate to use polystyrene/divinylbenzene microballoon, and chloromethylation condition is provided with methyl ether, and function of surface modification is carried out with reacting ethylenediamine, forms anion filler.
6. the preparation method according to claim any one of 1-5, it is characterised in that the reaction system in methods described includes oil phase and water phase, the oil phase includes toluene and chloroform；The water mutually includes methyl alcohol, water and acetone soln.
7. the preparation method according to claim any one of 1-5, it is characterised in that methods described includes：Chloromethylation, then the ethylenediamine group in modification in chloroform soln are first carried out in toluene solution, the porous polymer microballoon anion filler is formed.
8. the preparation method according to claim any one of 1-5, it is characterised in that methods described includes：
Polystyrene/divinylbenzene microballoon is dissolved in toluene, swelling 3h is stirred at room temperature, be cooled to room temperature, add chloromethyl ether and stannic chloride, continue that reaction 3h is stirred at room temperature, add deionized water terminating reaction, cleaned with hydrochloric acid, tetrahydrofuran, acetone, it is standby；
The chloromethylation microballoon for obtaining, adds in chloroform, adds ethylenediamine, is heated with stirring to 150oC, reacts 6h, is down to room temperature, with acetone, water, methyl alcohol process, vacuum drying；
The ethylenediamine microballoon for obtaining adds triethylamine, acetic anhydride, DMAP in toluene, is stirred overnight at room temperature, and is processed with methyl alcohol, water, acetone, and vacuum drying obtains the porous polymer microballoon anion filler.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107200804A (en) * | 2017-06-21 | 2017-09-26 | 广州康盛生物科技有限公司 | A kind of inflammatory factor macroporous adsorbent and preparation method thereof |
| CN107674142A (en) * | 2017-10-27 | 2018-02-09 | 常州嘉众新材料科技有限公司 | A kind of preparation method of the filler of efficiently purification phosphatidyl choline |
| WO2019128838A1 (en) * | 2017-12-25 | 2019-07-04 | Smart Liquid Crystal Technologies Co., Ltd. | Porous polymer microspheres with optical anisotropy, method of manufacturing the same and application of the same |
| CN111013554A (en) * | 2019-12-30 | 2020-04-17 | 高陵蓝晓科技新材料有限公司 | Composite macroporous adsorption resin for removing perfluorinated compounds in water |
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| WO2019128838A1 (en) * | 2017-12-25 | 2019-07-04 | Smart Liquid Crystal Technologies Co., Ltd. | Porous polymer microspheres with optical anisotropy, method of manufacturing the same and application of the same |
| CN111013554A (en) * | 2019-12-30 | 2020-04-17 | 高陵蓝晓科技新材料有限公司 | Composite macroporous adsorption resin for removing perfluorinated compounds in water |
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