CN109316983A - A kind of sulfonation dihydroxypropylchitosan modified polysulfone film and preparation method thereof - Google Patents
A kind of sulfonation dihydroxypropylchitosan modified polysulfone film and preparation method thereof Download PDFInfo
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- CN109316983A CN109316983A CN201811316205.5A CN201811316205A CN109316983A CN 109316983 A CN109316983 A CN 109316983A CN 201811316205 A CN201811316205 A CN 201811316205A CN 109316983 A CN109316983 A CN 109316983A
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- polysulfones
- sulfonation
- dihydroxypropylchitosan
- basement membrane
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
Abstract
A kind of sulfonation dihydroxypropylchitosan modified polysulfone film and preparation method thereof.2,4-DihydroxyBenzophenone (2,4-DHBP) is anchored on polysulfones membrane surface using PS membrane (PSF film) as basement membrane, by uv photo initiated grafting by the present invention, obtains hydroxylating polysulfones basement membrane；Vinyl glycidyl ether is grafted on by hydroxylating polysulfones membrane surface by etherification reaction again, obtains vinylated polysulfones basement membrane；Sulfonation dihydroxypropylchitosan (SDHPCS) is finally grafted on vinylated polysulfones membrane surface using Michael addition reaction, obtains the chitin modified PS membrane of two hydroxypropyl of sulfonation (SDHPCS-PSF film).It is characteristic of the invention that polysulfones film surface contains sulfonation dihydroxypropylchitosan modified polysulfone, the hydrophily and anticoagulant property of film surface are improved；And simple process, reaction condition are mildly controllable.
Description
Technical field
The invention belongs to biomedical materials field, in particular to a kind of sulfonation dihydroxypropylchitosan modified polysulfone film and
Preparation method.
Background technique
As the variation of spectrum of disease and aging of population process accelerate, in world wide, the disease incidence of chronic kidney disease is year by year
Rise.Renal replacement therapy patients number is with annual 11% or more speed increase.Haemodialysis is ESRD patient's primary treatment
One of method.How core of the dialysis membrane as hemodialysis effectively avoids film surface in dialysis procedure from blood coagulation occur
It is always the most important problem that haemodialyser clinical use faces with thrombus is formed.Polysulfones because have high temperature resistant,
The advantages that good mechanical property, strong corrosion resistance and the preparation for being widely used in dialysis membrane.Again because of aperture and hole in film-forming process
Diameter distribution can readily control, to the middle molecule harmful substance β in blood2Microglobulin and endotoxin can effectively remove, thus
The dialysis membrane that domestic market uses is based on PS membrane.However, without hydrophilic radical and anticoagulant property molecule in polysulfones membrane structure,
So polysulfones blood compatibility itself is poor, when with contacting blood, protein will be adsorbed onto rapidly on the surface of film, and adsorb
Protein layer can further result in platelet adhesion reaction, aggregation and blood coagulation etc..Present invention seek to address that polysulfone material produces when in use
It the problems such as raw protein absorption and blood coagulation, provides a kind of with the modified polysulfone film of good blood compatibility and its preparation side
Method.
The modification of PS membrane at present mainly uses the modified blood compatibility to improve material in surface, not only can be improved in this way
The blood compatibility of material, the excellent mechanical performances that also polysulfone membrane material can be kept intrinsic.The modified plan in surface is carried out to PS membrane
Slightly improve the hydrophilicity on surface, make negatively charged surface, surface grafting amphoteric ion polymer, design microphase-separated knot
The methods of large biological molecules such as structure, plantation endothelial cell, surface heparinization, the fixed urokinase of surface heparan and surface.
PS membrane is carried out ozone first by Yang MC etc. (Journal of Polymer Research, 2002,9 (2): 135-140.)
Then processing is reacted in film surface using acrylic acid, chitosan molecule is finally grafted on polysulfones film surface, has obtained hydrophily
With the preferably chitin modified polysulfones of biocompatibility.Mayes etc. (Biomaterials, 2006,27 (6): 856-865) first will
Polysulfones ontology is modified to chloromethyl polysulphone, recycles Williamson etherification reaction that will seal the polyethylene glycol bulk graft of one end
On chloromethyl polysulphone, to obtain using polyethylene glycol being hydrophilic side chain and polysulfones as the new polymers material of hydrophobic framework
Material.The hydrophily of this poly ethyldiol modified polysulfones bulk material has obtained very big improvement, thus anti-protein absorption and pollution
Ability greatly enhance.However interaction, egg between the length of hydrophilic graft chain, grafting chain density, chain and protein
The factors such as white size can all influence the effects of repulsion of the chain to protein.Liu P S etc. (Biomacromolecules,
2009,10 (10): 2809-16.) it is write articles from molecular engineering design viewpoint and points out that interior salt form amphoteric ion should have excellent resist
Coagulant property, zwitterionic materials have excellent blood compatibility, reason be amphoteric ion structure not only with protein
Active force is small between equal organisms macromolecular and its self-assembly, and its hydratability is strong, not can enter native protein conformation
Inside, to be conducive to original conformation of Protein requirement.Bioactive process and negative electrical charge design process on the surface of the material
In, physiological activator fixation can be formed bioactivity surface on the surface of the material, to weaken blood and material surface
Interaction, improve anticoagulation function.Wherein surface heparinization is to be most widely used, and is handled by test tube of hepari, can be activated
The activity of antithrombase plays blood coagulation resisting function, anticoagulative formation.However heparin molecule poor specificity, be easy to and its
He combines protein, especially platelet factor, thus induces thrombopenia, in addition, there is also induce haemorrhage for heparin
With the side effects such as hyperkalemia, while heparin is more expensive, limits the clinical application on heparin grafting polysulfones surface.Liu Tianming etc.
(Materials Science&Engineering C Materials for Biological Applications,2017,
Sulfonation hydroxypropyl chitosan 79:570) is grafted to polysulfones film surface, the hydrophily and blood compatibility of modified material obtain
It is apparent to improve.It is former that Zhao Changsheng etc. (Journal of Membrane Science, 2017,528:251-263) is dedicated to research
The gel particles of heparan structure and heparan structure are constructed polyether sulfone bio-compatible by the process for modifying surface such as position crosslinking/copolymerization
Property film, and the blood compatibility for improving polysulfones (PSF) and polyether sulfone (PES) film is had studied using aromatic polyamide nanofiber
Property.To the hot spot for being designed to current research on polysulfone membrane material surface and heparan molecule.Patent of invention CN104841285A
It discloses a kind of by citric acid and the chitin modified polyurethane of biocompatibility and preparation method thereof.Patent of invention CN
106943901A discloses the modified biocompatibility PS membrane of sulfonation hydroxypropyl chitosan.
In conclusion the conventional method for preparing anticoagulation PS membrane is first to prepare host material or basement membrane, then pass through
It is modified to make material that there is anticoagulation molecule structure and improve its blood compatibility.Patent of invention CN106943901A is disclosed to shell
Glycan C6Introducing hydroxypropyl on-OH carries out sulfonation, then sulfonation hydroxypropyl chitosan is grafted on polysulfones film surface, though it can change
It is apt to its blood compatibility, but to chitosan C6After introducing dihydroxypropyl on-OH, it can further improve hydrophily and anti-albumen be dirty
Metachromia.By being grafted on polysulfones film surface to dihydroxypropylchitosan progress sulfonation, then sulfonation dihydroxypropylchitosan, obtain
Sulfonation dihydroxypropylchitosan modified polysulfone film, blood compatibility can be further increased.
The purpose of the present invention is design one kind by sulfonation dihydroxypropylchitosan modified polysulfone film.It is characteristic of the invention that changing
Property polysulfones film surface contain sulfonation dihydroxypropylchitosan modified polysulfone, have good blood compatibility.First using PS membrane as base
Film is covalently connected the ketone group of 2,4-DihydroxyBenzophenone and the C-H of polysulfones membrane surface under conditions of ultraviolet irradiation
It connects, to introduce the activity functional groups hydroxyl for being easy to graft modification, obtains hydroxylating polysulfones basement membrane；And vinyl glycidyl then
Vinyl is introduced into hydroxylating polysulfones membrane surface by glycerin ether reaction, obtains vinylated polysulfones basement membrane；Finally in persulfuric acid
Mike is occurred into for the vinyl of amino and vinylated polysulfones membrane surface on sulfonation dihydroxypropylchitosan under the initiation of potassium
That addition reaction, obtains sulfonation dihydroxypropylchitosan modified polysulfone film.From hemoglutination mechanism and heparin anti-coagulating, antithrombotic
The mechanism of action is set out, and anticoagulant effect is reached, and improves the blood compatibility of polysulfones film surface.
Summary of the invention
The purpose of the present invention is designing a kind of sulfonation dihydroxypropylchitosan modified polysulfone film, which contains
There is sulfonation dihydroxypropylchitosan modified polysulfone, chemical structural formula indicates are as follows:
Indicate polysulfones basement membrane, chemical structural formula are as follows:
N=20~80 in structure；SDHPCS indicates sulfonation dihydroxypropylchitosan.
It is a further object to provide the preparation method of the sulfonation dihydroxypropylchitosan modified polysulfone film,
It mainly comprises the steps that
(1) hydroxylating of polysulfones membrane surface
Polysulfones basement membrane is impregnated in 0.5~1h in the 2,4-DihydroxyBenzophenone methanol solution of 0.1~0.5moL/L,
Middle hydroxylating polysulfones basement membrane and the mass ratio of vinyl glycidyl ether are 1:100~200,；Then polysulfones basement membrane taken out or
It stays in original solution, with 150~300W ultraviolet lamp, ultraviolet lamp wavelength is 220~380nm, and intensity is 20~30mW/cm2, irradiation
2~10min obtains hydroxylating polysulfones basement membrane；
(2) hydroxylating polysulfones membrane surface is vinylated
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, wherein vinylated polysulfones basement membrane and deionization
The mass ratio of water is 1:100~200, controls 40~60 DEG C of temperature, is stirred to react 1~2h；After taking-up with dehydrated alcohol and go from
Sub- water washing is clean, then at 40~50 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
(3) vinylated polysulfones membrane surface graft sulfonation dihydroxypropylchitosan
Sulfonation dihydroxypropylchitosan and deionized water are made into the sulfonation dihydroxypropyl shell that mass fraction is 1~10% to gather
Sugar aqueous solution；Then the potassium persulfate solution that mass fraction is 5% is added, adds vinylated polysulfones basement membrane, is protected in nitrogen
It protects lower stirring at normal temperature and reacts 10~20h, wherein the mass ratio of potassium persulfate solution and sulfonation dihydroxypropylchitosan aqueous solution is
1:10~20；After reaction, film washes clean is obtained sulfonation dihydroxypropylchitosan and changed with deionized water and dehydrated alcohol
Property PS membrane (SDHPCS-PSF film).
The chemical reaction that preparation process occurs are as follows:
Wherein, SDHPCS indicates sulfonation dihydroxypropylchitosan, chemical structural formula are as follows:
N=300~500 in structure.
Indicate polysulfones basement membrane, chemical structural formula are as follows:
N=20~80 in structure.
HO-PSF indicates hydroxylating polysulfones, chemical structural formula are as follows:
Indicate vinylated polysulfones, chemical structural formula are as follows:
SDHPCS-PSF indicates sulfonation dihydroxypropylchitosan modified polysulfone, chemical structural formula are as follows:
The present invention prepares sulfonation dihydroxypropylchitosan modified polysulfone film, surface hydrophilicity, anticoagulation using three steps
Property and blood compatibility be improved significantly.Compared with unmodified PS membrane, the hydrophily and anti-protein of modified polysulfone film
Pollutant performance is greatly improved, and water contact angle is reduced to 35 ° by 76 °, and the adsorbance of bovine serum albumin is by 380 μ g/cm2It reduces
To 56 μ g/cm2, the introducing of sulfonation dihydroxypropylchitosan is greatly improved water contact angle, reduces the absorption of protein, molten
Blood rate drops to 0.9% by 2.8%, and adsorbance, aggregation extent and the deformation extent of blood platelet also significantly reduce, and are not formed
Thrombus, result above all show that polysulfones film surface contains sulfonation dihydroxypropylchitosan and significantly improves the blood compatibility of film surface
Property.
The invention has the following advantages that
1. modified polysulfone film surface contains sulfonation dihydroxypropylchitosan modified polysulfone, improve PS membrane hydrophily,
Anti-protein-contamination and anticoagulation function.
2. being modified in terms of surface is modified with uv photo initiated grafting two to PSF film, it is poly- to realize sulfonation dihydroxypropyl shell
Sugar is modified polysulfones membrane surface.
3. the present invention is modified polysulfones membrane surface, the mechanical strength and structural stability of original film are maintained.
4. present invention process is simple, reaction condition is mildly easily-controllable.
Detailed description of the invention
Fig. 1 sulfonation dihydroxypropylchitosan modified polysulfone film preparation process flow of the present invention.
Specific embodiment
With reference to the accompanying drawing and example is described further the present invention.
Embodiment 1
Polysulfones basement membrane is impregnated in 1h in the 2,4 dihydroxyl benzophenone methanol solution of 0.4moL/L；Polysulfones basement membrane is taken
It out or stays in original solution, with the ultraviolet light irradiation 5min of 160W, obtains hydroxylating polysulfones basement membrane；
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, temperature 50 C is controlled, is stirred to react 2h；It takes out
Afterwards use dehydrated alcohol and deionized water washes clean, then at 45 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
1g SDHPCS obtained above is added in the deionized water of 45mL, is stirred evenly, SDHPCS aqueous solution is made into；
Then the potassium persulfate solution that 5mL mass fraction is 5% is added, vinylated polysulfones basement membrane obtained above is added, in nitrogen
Under gas shielded, stirring at normal temperature reacts 20h；After reaction, film washes clean is obtained into sulfonation with deionized water and dehydrated alcohol
Dihydroxypropylchitosan modified polysulfone film.
Embodiment 2
Polysulfones basement membrane is impregnated in 40min in the 2,4 dihydroxyl benzophenone methanol solution of 0.4moL/L；By polysulfones base
Film takes out or stays in original solution, with the ultraviolet light irradiation 5min of 180W, obtains hydroxylating polysulfones basement membrane；
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, temperature 50 C is controlled, is stirred to react 2h；It takes out
Afterwards use dehydrated alcohol and deionized water washes clean, then at 45 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
2g SDHPCS obtained above is added in the deionized water of 45mL, is stirred evenly, SDHPCS aqueous solution is made into；
Then the potassium persulfate solution that 5mL mass fraction is 5% is added, vinylated polysulfones basement membrane obtained above is added, in nitrogen
Under gas shielded, stirring at normal temperature reacts 20h；After reaction, film washes clean is obtained into sulfonation with deionized water and dehydrated alcohol
Dihydroxypropylchitosan modified polysulfone film.
Embodiment 3
Polysulfones basement membrane is impregnated in 1h in the 2,4 dihydroxyl benzophenone methanol solution of 0.4moL/L；Polysulfones basement membrane is taken
It out or stays in original solution, with the ultraviolet light irradiation 10min of 200W, obtains hydroxylating polysulfones basement membrane；
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, temperature 50 C is controlled, is stirred to react 2h；It takes out
Afterwards use dehydrated alcohol and deionized water washes clean, then at 45 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
2g SDHPCS obtained above is added in the deionized water of 45mL, is stirred evenly, SDHPCS aqueous solution is made into；
Then the potassium persulfate solution that 5mL mass fraction is 5% is added, vinylated polysulfones basement membrane obtained above is added, in nitrogen
Under gas shielded, stirring at normal temperature reacts 20h；After reaction, film washes clean is obtained into sulfonation with deionized water and dehydrated alcohol
Dihydroxypropylchitosan modified polysulfone film.
Embodiment 4
Polysulfones basement membrane is impregnated in 1h in the 2,4 dihydroxyl benzophenone methanol solution of 0.4moL/L；Polysulfones basement membrane is taken
It out or stays in original solution, with the ultraviolet light irradiation 10min of 240W, obtains hydroxylating polysulfones basement membrane；
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, temperature 50 C is controlled, is stirred to react 2h；It takes out
Afterwards use dehydrated alcohol and deionized water washes clean, then at 45 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
3g SDHPCS obtained above is added in the deionized water of 45mL, is stirred evenly, SDHPCS aqueous solution is made into；
Then the potassium persulfate solution that 5mL mass fraction is 5% is added, vinylated polysulfones basement membrane obtained above is added, in nitrogen
Under gas shielded, stirring at normal temperature reacts 20h；After reaction, film washes clean is obtained into sulfonation with deionized water and dehydrated alcohol
Dihydroxypropylchitosan modified polysulfone film.
The performance of sulfonation dihydroxypropylchitosan modification biological compatibility PS membrane of the present invention is as shown in table 1.
The sulfonation dihydroxypropylchitosan modified polysulfone film of the present invention of table 1
Claims (2)
1. a kind of sulfonation dihydroxypropylchitosan modified polysulfone film, it is characterised in that: modified polysulfone film surface contains sulfonation dihydroxy
The chitin modified polysulfones of propyl, chemical structural formula indicate are as follows:
Indicate polysulfones basement membrane, chemical structural formula are as follows:
N=20~80 in structure；SDHPCS indicates sulfonation dihydroxypropylchitosan.
2. a kind of preparation method of sulfonation dihydroxypropylchitosan modified polysulfone film as described in claim 1, it is characterised in that
The following steps are included:
(1) hydroxylating of polysulfones membrane surface
Polysulfones basement membrane is impregnated in 0.5~1h in the 2,4 dihydroxyl benzophenone methanol solution of 0.1~0.5moL/L；Then will
Polysulfones basement membrane takes out or stays in original solution, and the wavelength with 150~300W ultraviolet lamp, ultraviolet lamp is 220~380nm, and intensity is
20~30mW/cm2, 2~10min is irradiated, hydroxylating polysulfones basement membrane is obtained；
(2) hydroxylating polysulfones membrane surface is vinylated
Hydroxylating polysulfones basement membrane is added in vinyl glycidyl ether, wherein hydroxylating polysulfones basement membrane and vinyl glycidyl are sweet
The mass ratio of oily ether is 1:100~200, controls 40~60 DEG C of temperature, is stirred to react 1~2h；With dehydrated alcohol and going after taking-up
Ionized water washes clean, then at 40~50 DEG C it is vacuum dried to get arrive vinylated polysulfones basement membrane；
(3) vinylated polysulfones membrane surface graft sulfonation dihydroxypropylchitosan
Sulfonation dihydroxypropylchitosan and deionized water are made into the sulfonation dihydroxypropylchitosan water that mass fraction is 1~10%
Solution；Then the potassium persulfate solution that mass fraction is 5% is added, vinylated polysulfones basement membrane is added, wherein vinylated
Polysulfones basement membrane and the mass ratio of deionized water are 1:100~200, and stirring at normal temperature reacts 10~20h under nitrogen protection, wherein mistake
The mass ratio of potassium sulfate solution and sulfonation dihydroxypropylchitosan aqueous solution is 1:10~20；After reaction, deionized water is used
With dehydrated alcohol by film washes clean, sulfonation dihydroxypropylchitosan modified polysulfone film, i.e. SDHPCS-PSF film are obtained.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113171693A (en) * | 2021-04-30 | 2021-07-27 | 河南鑫安利职业健康科技有限公司 | Chemical sewage treatment method based on polysulfone composite microfiltration membrane |
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