CN107325231B - A kind of preparation and its application of porous organic polymer - Google Patents
A kind of preparation and its application of porous organic polymer Download PDFInfo
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- CN107325231B CN107325231B CN201710556809.6A CN201710556809A CN107325231B CN 107325231 B CN107325231 B CN 107325231B CN 201710556809 A CN201710556809 A CN 201710556809A CN 107325231 B CN107325231 B CN 107325231B
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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
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
- C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
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- Polymers & Plastics (AREA)
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Abstract
The invention discloses a kind of preparation method and application of poly-dopamine modified lithium polystyrene-ethylene glycol dimethacrylate porous organic polymer, including polystyrene-ethylene glycol dimethacrylate and the preparation of poly-dopamine modified lithium polystyrene-ethylene glycol dimethacrylate porous organic polymer.Polystyrene-ethylene glycol dimethacrylate is prepared using reverse micelle swelling method, using styrene as monomer, ethylene glycol dimethacrylate is crosslinking agent, and pore-foaming agent is that polyvinyl alcohol synthesizes porous organic polymer particle.It applies and is modified by poly-dopamine, be prepared poly-dopamine modified lithium polystyrene-ethylene glycol dimethacrylate porous organic polymer, hydrophilicity and all obviously increases the absorption property of the large biological molecules such as polypeptide, protein, polysaccharide mechanical performance.
Description
Technical field
The invention belongs to the preparations of organic high molecular polymer and bio-molecular separation field, and in particular to a kind of poly- DOPA
Modified polystyrene-ethylene glycol dimethacrylate porous organic polymer the preparation of amine and in bio-molecular separation field
Application.
Technical background
Porous organic polymer (Porous Organic Polymers, POPs) is a kind of nonionic, highly cross-linked, tool
There is the general name of the organic high molecular polymer of a large amount of pore structures, is by polymerized monomer, crosslinking agent, pore-foaming agent, dispersing agent etc. in spy
Aggregated reaction is prepared under fixed condition.After Macroscopic single crystal, pore-foaming agent is removed, it is each just to will form aperture multiplicity, shape
Hole that is different, interpenetrating, shows as porous three-dimensional reticular structure, in the dry state its internal porosity with higher,
And aperture is larger.Therefore, it is specific applied to adsorbing from solution to can be used as a kind of organic high molecular polymer adsorbent by POPs
The compound of structure, this is a kind of important development in separation analysis field.Since with good absorption property, POPs is
It is widely used in the fields such as industrial decoloration, environmental protection, biological medicine, and increasingly attracts the concern of people.
In order to improve the absorption property of POPs, it is typically employed in POPs and shows modified method.Currently, commonly to high score
Sub- polymer particle surface method of modifying has 2 kinds: physical absorption and chemical bonding.Physical absorption is applied in polymer particle surface
One or more layers is applied simultaneously containing the polymer of hydrophilic radical, and stable hydrophilic granules are obtained by a series of post-crosslinking；
Chemical bonding then often needs first to be bonded active group in polymer particle surface, then recycles its group activity and hydrophily
Polymer reacts, hydrophobic to achieve the purpose that eliminate.The common macromolecule that can be used to be bonded has polyvinyl alcohol, poly- second two
Alcohol and cyclodextrin etc..
But for biomolecule, especially large biological molecules such as polypeptide, protein, polysaccharide, molecular weight is big, point
Sub- size is big, action site is more, currently used POPs, including modified POPs, opposite to the absorption property of biomolecule
It is poor.Wherein, most popular is polystyrene-divinylbenzene POPs, but its surface there are a large amount of phenyl ring and hangs
Double bond is hung, has hydrophobicity compared with the defects of strong, aperture is small, seriously affects its answering in separation fields such as polypeptide, protein, polysaccharide
With.
Summary of the invention
The present invention provides a kind of preparation method of porous organic polymer and the application technology in bio-molecular separation field,
I.e. a kind of polystyrene-ethylene glycol dimethacrylate POPs modified using poly-dopamine (PDOPA), the hydrophily of preparation
The surface POPs has a large amount of hydroxyl, its hydrophily and absorption property can be improved, while modified POPs possesses stronger machine
Tool intensity is conducive to improve the POPs to the separating property of biomolecule.
Present invention firstly provides a kind of styrene-ethylene glycol dimethacrylate copolymer, preparation method includes such as
Under step:
1) by the polyvinyl alcohol high-temperature digestion aqueous phase solution of 0.2~2 mass parts, the table of 0.01~1 mass parts is added
Face activating agent, the electrolyte of 0.01~1 mass parts, 0.01~1 mass parts hydroquinone, be mixed and made into continuous phase.
2) by the benzoyl peroxide of 0.1~1 mass parts, the hexadecane of 0.1~1 mass parts, 1~10 mass parts sapn
80, the styrene of 1~10 mass parts and the ethylene glycol dimethacrylate of 0.5~10 mass parts are mixed, at ultrasound
Dispersed phase is obtained after reason.
3) dispersed phase of continuous phase and step 2) in step 1) is mixed to join in reaction vessel, is held under oxygen-free environment
Continuous stirring is filtered after 5~20h of heating polymerization, by the solids being obtained by filtration successively use water, ethyl alcohol or methanol, acetone or
After n-hexane washing, it is dried to obtain styrene-ethylene glycol dimethacrylate copolymer.
Above-mentioned steps 1) in high temperature be 50~400 DEG C；
Above-mentioned steps 1) in surfactant be lauryl sodium sulfate, dodecyl sodium sulfate, sulfated castor oil
With the combination of any one or more of sodium glycocholate；
Above-mentioned steps 1) in electrolyte be any one of sodium sulphate and sodium carbonate or two kinds combination；
Above-mentioned steps 3) in oxygen-free environment be by be passed through any one or more of nitrogen, argon gas or carbon dioxide obtain
's；
Above-mentioned steps 3) in mixing speed be 100~400rpm；
Above-mentioned steps 3) in heating temperature be 40~200 DEG C.
Another aspect of the present invention provides a kind of porous polymer, is by styrene-ethylene glycol two of 0.01~2 mass parts
Methacrylate copolymer is added in ethanol solution or methanol solution, and the Tris-HCl for adding 20~100 mass parts is molten
Liquid, the Dopamine hydrochloride of 0.01~1 mass parts are uniformly mixed, and adjust pH value, after carrying out oscillating reactions；Reaction product is carried out
Filtering, be obtained by filtration after solids successively wash with water, ethyl alcohol or methanol, acetone or n-hexane, dry, obtain the present invention
Porous organic polymer.
Wherein Dopamine hydrochloride is 0.01~1 mass parts；
Wherein pH value is 7~14；
Wherein the reaction time is 1~20h.
Styrene prepared by the present invention-ethylene glycol dimethacrylate copolymer (abbreviation PSEP), can be used for polypeptide, egg
It is prepared by the separation of the macromolecular compounds such as white matter, polysaccharide.The a large amount of hydroxyl in poly-dopamine surface can further derivatization, be prepared into
Meet the separating medium of different demands.It can also be carried out in Solid Phase Extraction chromatography, size exclusion chromatograph and high performance liquid chromatography field
Wide application.
The porous polymer surface of poly-dopamine modified lithium polystyrene-ethylene glycol dimethacrylate prepared by the present invention
With hydroxyl abundant, fabulous hydrophily and absorption property are shown.Its storage modulus obviously rises, and then shows fabulous
Mechanical strength.Porous polymer of the invention becomes a kind of equimolecular excellent for separation and Extraction polypeptide, protein, polysaccharide
Material.Poly-dopamine modified lithium polystyrene-ethylene glycol dimethacrylate porous polymer sheet face has great amount of hydroxy group, can
Carry out amino, hydroxyl, carboxyl, sulfonic group, carbonyl etc., imidazoles, carbazole plasma liquid, polymer brush, poly ion liquid brush, poly- electricity
It solves the functional groups such as matter brush and carries out functionalization, obtain a series of porous polymeric of different specific surface areas, pore volume and average pore size
Object enriches the type of the porous material, has widened its application field, with good application prospect.
Detailed description of the invention
Fig. 1: the scanning electron microscopic picture of porous organic polymer, wherein a:PSE1；B:D1；C:D2；D:D3.
Fig. 2: the storage modulus figure of porous organic polymer.
Specific embodiment
The present invention is described in detail below with reference to embodiment.
Embodiment 1
The preparation of PSE polymer: polyvinyl alcohol 0.5g is dissolved in 70mL aqueous phase solution in 60 DEG C when, dodecane is added
Base sodium sulphate 0.02g, sodium carbonate 0.02g and hydroquinone 0.015g, mixing, obtain continuous phase, spare；By benzoyl peroxide first
Acyl 0.2g, hexadecane 0.1g, sorbester p17 2g, styrene 2.5g and ethylene glycol dimethacrylate 1g, mixing, ultrasound
10min obtains dispersed phase；Continuous phase and dispersed phase are mixed to join in reaction vessel, nitrogen environment, 120rpm is persistently stirred,
65 DEG C of heating polymerize 6h, and filtering is dry after the solids being obtained by filtration sequentially is used water, ethyl alcohol and acetone washing, obtain benzene
Ethylene-ethylene glycol dimethacrylate copolymer p SE1.Bovine serum albumin, adsorption capacity 162mg/ are adsorbed using PSE1
G (in terms of PSE1 dry weight).
Embodiment 2
The preparation of PSE polymer: polyvinyl alcohol 1.0g is dissolved in 100mL aqueous phase solution in 100 DEG C when, is added 12
Sodium alkyl sulfate 0.03g, sodium carbonate 0.04g and hydroquinone 0.02g, mixing, obtain continuous phase, spare；By benzoyl peroxide first
Acyl 0.3g, hexadecane 0.3g, sorbester p17 3g, styrene 4g and ethylene glycol dimethacrylate 3g, mixing, ultrasound
30min obtains dispersed phase；Continuous phase and dispersed phase are mixed to join in reaction vessel, ar gas environment, 200rpm is persistently stirred,
85 DEG C of heating polymerize 8h, and filtering is dry after the solids being obtained by filtration sequentially is used water, methanol and acetone washing, obtain benzene
Ethylene-ethylene glycol dimethacrylate copolymer p SE2.
PSE2 resin particle 0.2g obtained is weighed, is added 30% ethanol solution 15mL, Dopamine hydrochloride 0.01g, three
Hydroxymethyl aminomethane (abbreviation Tris) hydrochloric acid solution 20mL, mixing, adjusting pH value is 7.5, oscillating reactions 2h on shaking table, mistake
Filter, will be obtained by filtration after solids sequentially wash with water, ethyl alcohol and n-hexane, dry, obtain D1 porous organic polymer.
Adsorb bovine insulin using D1, adsorption capacity is 40mg/g (in terms of D1 dry weight).
Embodiment 3
The preparation of PSE polymer: polyvinyl alcohol 1.5g is dissolved in 200mL aqueous phase solution in 200 DEG C when, is added 12
Sodium alkyl sulfate 0.5g, sodium carbonate 0.6g and hydroquinone 0.4g, mixing, obtain continuous phase, spare；By benzoyl peroxide
0.5g, hexadecane 0.4g, sorbester p17 5g, styrene 6g and ethylene glycol dimethacrylate 5g, mixing, ultrasonic 60min,
Obtain dispersed phase；Continuous phase and dispersed phase are mixed to join in reaction vessel, carbon dioxide environment, 300rpm is persistently stirred, and 100
DEG C heating polymerization 12h, filtering, after the solids being obtained by filtration sequentially wash with water, methanol and n-hexane, dry, obtain
Styrene-ethylene glycol dimethacrylate copolymer p SE3.
PSE3 resin particle 1g obtained is weighed, 60% methanol solution 80mL is added, trishydroxymethylaminomethane is (referred to as
Tris) hydrochloric acid solution 40mL and Dopamine hydrochloride 0.2g, mixing, adjusting pH value is 9, oscillating reactions 10h on shaking table, filtering,
To be obtained by filtration after solids sequentially uses water, ethyl alcohol and acetone washing, it is dry, obtain D2 porous organic polymer.It utilizes
D2 adsorbs bradykinin, and adsorption capacity is 35mg/g (in terms of D2 dry weight).
Embodiment 4
The preparation of PSE polymer: polyvinyl alcohol 1.5g is dissolved in 300mL aqueous phase solution in 300 DEG C when, is added 12
Sodium alkyl sulfate 0.8g, sodium carbonate 0.9g and hydroquinone 0.8g, mixing, obtain continuous phase, spare；By benzoyl peroxide
0.7g, hexadecane 0.9g, sorbester p17 8g, styrene 8.5g and ethylene glycol dimethacrylate 8.9g, mixing, ultrasound
100min obtains dispersed phase；Continuous phase and dispersed phase are mixed to join in reaction vessel, nitrogen environment, 380rpm is persistently stirred,
150 DEG C of heating polymerize 18h, and filtering is dry after the solids being obtained by filtration sequentially is used water, methanol and acetone washing, obtain
Styrene-ethylene glycol dimethacrylate copolymer p SE4.
PSE4 resin particle 1.7g obtained is weighed, 90% ethanol solution 140mL, trishydroxymethylaminomethane is added
(abbreviation Tris) hydrochloric acid solution 90mL and Dopamine hydrochloride 0.95g, mixing, adjusting pH value is 10, oscillating reactions on shaking table
17h, filtering, will be obtained by filtration after solids sequentially wash with water, ethyl alcohol and n-hexane, dry, it is porous organic to obtain D3
Polymer.Adsorb glutathione using D3, adsorption capacity is 41mg/g (in terms of D3 dry weight).
Characterizing method
1. specific surface area, pore volume and average pore size
Using the porous organic polymer of BET method measurement preparation, the physical parameter of above 7 kinds of polyalcohol stephanoporate particles is as follows
Table:
The physical parameter of the 7 kinds of embodiment polyalcohol stephanoporate particles of the invention of table 1
As known from Table 1, the specific surface area of PSE series plastics, pore volume and average pore size are larger.Therefore, this porous has
Machine polymer is conducive to adsorb the biomolecule such as protein, the polysaccharide of macromolecular.With the increase of poly-dopamine modification amount, ratio
Surface area, pore volume and average pore size gradually decrease, and are suitable for separating the lesser polypeptide of molecular weight.
2. electron microscopic picture
From the scanning electron microscopic picture of Fig. 1 it is found that the average pore size of PSE1 is larger, surface is relatively rough.With poly- DOPA
The average pore size of the increase of amine-modified amount, D1, D2, D3 gradually decreases, and surface becomes gradually smooth.
3. mechanical strength
As can be seen from Figure 2, the storage modulus of D1, D2, D3 gradually increase, after this shows poly-dopamine modification, mechanical strength
Increase, and increases with the increase of poly-dopamine modification amount.Therefore, porous organic polymer surface modification poly-dopamine can
To greatly improve its mechanical strength.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention do not receive above-described embodiment
Limitation, other any made change, modification, substitution, combination, letters without departing from the spirit and principles of the present invention
Change, the displacement that should be equivalent is prevented, is included within the scope of the present invention.
Claims (7)
1. a kind of porous polymer is that the styrene of 0.01~2 mass parts-ethylene glycol dimethacrylate copolymer is added
Into ethanol solution or methanol solution, the Tris-HCl solution of 20~100 mass parts, the hydrochloric acid of 0.01~1 mass parts are added
Dopamine is uniformly mixed, and adjusts pH value, after carrying out oscillating reactions；Reaction product is filtered, be obtained by filtration solids according to
It is secondary washed with water, ethyl alcohol or methanol, acetone or n-hexane after, it is dry, porous organic polymer is made；
The styrene-ethylene glycol dimethacrylate copolymer preparation method comprises the following steps that
1) surface in the polyvinyl alcohol high-temperature digestion aqueous phase solution of 0.2~2 mass parts, adding 0.01~1 mass parts is living
Property agent, the electrolyte of 0.01~1 mass parts, 0.01~1 mass parts hydroquinone, be mixed and made into continuous phase；
2) by the benzoyl peroxide of 0.1~1 mass parts, the hexadecane of 0.1~1 mass parts, the sorbester p17 of 1~10 mass parts, 1
The styrene of~10 mass parts and the ethylene glycol dimethacrylate of 0.5~10 mass parts are mixed, after ultrasonic treatment
Obtain dispersed phase；
3) dispersed phase of continuous phase and step 2) in step 1) is mixed to join in reaction vessel, is persistently stirred under oxygen-free environment
Mix, heating polymerization 5~20h after be filtered, by the solids being obtained by filtration successively use water, ethyl alcohol or methanol, acetone or just oneself
After alkane washing, it is dried to obtain styrene-ethylene glycol dimethacrylate copolymer.
2. porous polymer as described in claim 1, wherein the high temperature in step 1) is 50~400 DEG C.
3. porous polymer as described in claim 1, wherein the surfactant in step 1) is lauryl sodium sulfate, ten
The combination of any one or more of dialkyl sulfonates, sulfated castor oil, sodium glycocholate.
4. porous polymer as described in claim 1, in step 1) electrolyte be any one of sodium sulphate and sodium carbonate or
Two kinds of combinations.
5. porous polymer as described in claim 1, wherein oxygen-free environment is by being passed through nitrogen, argon gas or two in step 3)
What any one or more of carbonoxide obtained.
6. porous polymer as described in claim 1, wherein pH value is adjusted to 7~14.
7. application of the porous polymer described in claim 1 in the separation preparation of macromolecular compound or chromatographic field.
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| CN110841602B (en) * | 2019-09-30 | 2022-08-05 | 佛山市博新生物科技有限公司 | Blood purification material based on mussel bionic chemistry and preparation method thereof |
| CN111001187B (en) * | 2019-12-13 | 2021-02-19 | 武汉大学 | Preparation method of novel cyclodextrin metal organic framework material chiral capillary electrochromatography open tubular column |
| CN113817217B (en) * | 2021-10-19 | 2023-04-28 | 肇庆学院 | Porous polymer microsphere for high selective adsorption of enrofloxacin and preparation method thereof |
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| CN104558362A (en) * | 2013-10-29 | 2015-04-29 | 中国石油天然气股份有限公司 | Terpolymer carrier and preparation method thereof |
| CN104861102A (en) * | 2015-05-27 | 2015-08-26 | 青岛大学 | Porous crosslinked polystyrene microsphere and preparation method thereof |
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| CN104558362A (en) * | 2013-10-29 | 2015-04-29 | 中国石油天然气股份有限公司 | Terpolymer carrier and preparation method thereof |
| CN104861102A (en) * | 2015-05-27 | 2015-08-26 | 青岛大学 | Porous crosslinked polystyrene microsphere and preparation method thereof |
| CN105289540A (en) * | 2015-11-11 | 2016-02-03 | 江苏大学 | Method for preparing porous difunctional adsorption material |
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