CN109316986B - Acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane and preparation method thereof - Google Patents
Acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane and preparation method thereof Download PDFInfo
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Abstract
An acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane and a preparation method thereof. Firstly, grafting Acrylic Acid (AA) on the surface of a polysulfone membrane (PSF membrane) through ultraviolet grafting to obtain an acrylic acid modified polysulfone membrane (AA-PSF membrane); and grafting sulfonated dihydroxypropyl chitosan (SDHPCS) on the surface of the AA-PSF membrane by utilizing the condensation reaction of carboxyl and amino to obtain the acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane (SDHPCS-AA-PSF membrane). The invention is characterized in that the polysulfone membrane is taken as a base membrane, acrylic acid is grafted on the surface of the membrane, and then sulfonated dihydroxypropyl chitosan is grafted, so that the obtained acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane has good hydrophilicity and anticoagulation; and the preparation process is simple, and the conditions are mild and easy to control.
Description
Technical Field
The invention belongs to the field of biomedical materials, and particularly relates to an acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane and a preparation method thereof.
Background
Polysulfone is used as a blood contact material with great application potential, and the anticoagulation performance of polysulfone is continuously improved. Polysulfone membranes are free of hydrophilic groups and anticoagulant molecules, so polysulfone itself is poorly hemocompatible, proteins are rapidly adsorbed onto the surface of the membrane upon contact with blood, and the adsorbed protein layer may further cause platelet adhesion, aggregation, coagulation, and the like. The invention aims to solve the problems of protein adsorption, blood coagulation and the like generated when a polysulfone material is used, and provides a modified polysulfone membrane with good blood compatibility and a preparation method thereof.
At present, the polysulfone membrane is modified mainly by surface modification to improve the blood compatibility of the material, so that the blood compatibility of the material can be improved, and the inherent good mechanical property of the polysulfone membrane material can be maintained. The polysulfone membrane is subjected to a surface modification strategy to improve the hydrophilic property of the surface, the surface is charged with negative charges, the surface is grafted with a zwitterionic polymer, a microphase separation structure is designed, endothelial cells are planted, the surface is heparinized, and biomacromolecules such as urokinase and the like are fixed on the surface. Yang MC (Journal of Polymer Research,2002,9(2):135-140.) firstly carries out ozone treatment on a polysulfone membrane, then acrylic acid is utilized to react on the surface of the membrane, and finally chitosan molecules are grafted on the surface of the polysulfone membrane, so that the chitosan modified polysulfone with better hydrophilicity and biocompatibility is obtained. TM Liu et al (Materials Science & Engineering C Materials for Biological Applications,2017,79:570) grafted sulfonated hydroxypropyl chitosan on the surface of polysulfone membrane, the modified material hydrophilicity and blood compatibility are obviously improved. Tumei et al (journal of Chinese medical physics, 2003,20(4):297-298.) found that carboxyl and sulfonic acid groups have a synergistic effect on anticoagulant properties, and the degree of blood compatibility mainly depends on the ratio of the carboxyl and the sulfonic acid groups; for sulfonated O-carboxymethyl chitosan, the anticoagulant property is best when the degree of substitution of N-carboxymethyl is 0.585 and the degree of substitution of O-sulfonic group is 0.593; for sulfonated N-carboxymethyl chitosan, the anticoagulant effect is best when the degree of substitution of N-sulfonic acid group is 0.689 and the degree of substitution of O-carboxymethyl is 0.593. The invention patent CN 108043251A blends Wolpasha microsphere particles with polysulfone or polyethersulfone to obtain a modified membrane with good antiplatelet and antithrombotic properties. The invention patent CN 104841285A discloses a biocompatible polyurethane modified by citric acid and chitosan and a preparation method thereof. The invention patent CN 106943901A discloses a sulfonated hydroxypropyl chitosan modified biocompatible polysulfone film.
In summary, the general method for preparing the anticoagulant polysulfone membrane is to prepare a matrix material or a basement membrane, and then to make the material have an anticoagulant molecular structure by the methods of surface modification, bulk modification, blending and the like, thereby improving the blood compatibility of the material. The invention patent CN 106943901A discloses para-chitosan C6The introduction of hydroxypropyl group on-OH position is sulfonated, then the sulfonated hydroxypropyl chitosan is grafted on the surface of polysulfone membrane, although the blood compatibility can be improved, the sulfonated hydroxypropyl chitosan can improve the blood compatibility of the polysulfone membrane6After dihydroxypropyl group is introduced to-OH position, hydrophilicity and protein contamination resistance can be further improved, and carboxyl group and sulfonic group have synergistic effect on anticoagulation performance. The acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane is obtained by sulfonating dihydroxypropyl chitosan and grafting the sulfonated dihydroxypropyl chitosan on the surface of the acrylic acid modified polysulfone membrane, and the blood compatibility of the acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane can be further improved.
The invention aims to design a blood compatible polysulfone membrane modified by acrylic acid and sulfonated dihydroxypropyl chitosan; the modified polysulfone membrane has the structural characteristics that the polysulfone membrane is used as a base membrane, and the surface of the membrane is grafted with acrylic acid and then sulfonated dihydroxypropyl chitosan; the introduction of acrylic acid and sulfonated dihydroxypropyl chitosan improves the hydrophilicity and anticoagulation performance of the membrane surface; by modifying the surface of the polysulfone membrane, the whole membrane material has good physicochemical stability; the preparation method provided by the invention has the characteristics of simple process, mild and easily-controlled reaction conditions and the like.
Disclosure of Invention
The invention aims to design an acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane, wherein a polysulfone membrane (PSF membrane) is used as a base membrane, Acrylic Acid (AA) is grafted on the surface of the base membrane, and then sulfonated dihydroxypropyl chitosan (SDHPCS) is grafted, namely the surface of the membrane contains acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone (SDHPCS-AA-PSF), and the chemical structural formula is as follows:
in the structure, n is 20-80, and m is 1-50; r is OH or sulfonated dihydroxypropyl chitosan.
The invention also aims to provide a preparation method of the acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane, which mainly comprises the following steps:
(1) acrylic modification of PSF film surface
Adding a polysulfone membrane (PSF membrane) into an Acrylic Acid (AA) aqueous solution with the mass concentration of 1-5% for 20-40 min; taking out the polysulfone membrane or leaving the polysulfone membrane in the original solution, and using a 150-300W ultraviolet lamp (with the wavelength of 220-380 nm and the intensity of 20-30 mW/cm)2) Irradiating for 2-10 min, taking out, washing with absolute ethyl alcohol and deionized water, and then drying in vacuum at 40-50 ℃ to obtain an AA-PSF film;
(2) SDHPCS modification of AA-PSF membrane surfaces
Adding the AA-PSF film into an acetic acid buffer solution with the temperature of 4 ℃ and the concentration of carbodiimide (EDC) of 2-4 mmoL/L for 3-5 h to activate carboxyl on the surface of the film; then, washing the membrane by using a phosphate buffer solution and deionized water in sequence, adding the activated membrane into an acetic acid solution of SDHPCS (sodium dehydrobutyrate succinate) at the temperature of 4 ℃ and at the concentration of 0.1-0.5 mg/mL, and stirring for reacting for 20-24 hours; and soaking the obtained membrane in 1-2 mmoL/L glutaraldehyde solution at 20-40 ℃ for 50-60 min, washing with phosphate buffer solution and deionized water, soaking in deionized water for 10-12 h, and drying in vacuum at normal temperature to obtain the SDHPCS-AA-PSF membrane.
The reactions occurring during the modification are:
AA-PSF+SDHPCS→SDHPCS-AA-PSF (2)
AA-PSF represents acrylic acid modified polysulfone with a chemical structural formula:
SDHPCS-AA-PSF represents acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone, and the chemical structural formula of the polysulfone is as follows:
in the structure, n is 20-80, and m is 1-50; r represents OH or SDHPCS; SDHPCS represents sulfonated dihydroxypropyl chitosan, the chemical structural formula of which is:
or
Or
In the structure, r is 300-500.
The invention adopts two steps to prepare the acrylic acid and sulfonated dipropyl propyl chitosan modified polysulfone membrane, and the hydrophilicity, the anticoagulation and the blood compatibility of the PSF modified polysulfone membrane are obviously improved by changing the chemical structure of the surface of the PSF base membrane. Compared with the unmodified polysulfone membrane, the modified polysulfone membrane has greatly improved hydrophilicity and protein pollution resistance, the water contact angle is reduced from 76 degrees to 28 degrees, and the adsorption quantity of bovine serum albumin is reduced from 380 mu g/cm2Reduced to 52. mu.g/cm2The introduction of the sulfonated dipropyl propyl chitosan greatly improves the water contact angle, reduces the adsorption of protein and reduces the hemolysis rate from 2.8 percent to 0.9 percent. The adsorption amount, aggregation degree and deformation degree of the platelets are also obviously reduced, and no thrombus is formed. The sulfonated dihydroxypropyl chitosan with a heparinoid structure and the carboxyl on the surface act on the blood coagulation factors together, so that the anticoagulation performance of the material is improved.
The invention has the following advantages:
1. the heparinoid substance sulfonated dihydroxypropyl chitosan is grafted on the surface of the acrylic acid modified polysulfone membrane, so that the hydrophilicity, the protein pollution resistance and the anticoagulation of the surface of the polysulfone membrane are further improved.
2. The modification of acrylic acid and sulfonated dihydroxypropyl chitosan on the surface of the polysulfone membrane is realized through ultraviolet grafting and condensation reaction.
3. The polysulfone membrane surface is modified, and the mechanical strength and the structural stability of the original membrane are maintained.
4. The preparation method provided by the invention is simple, and the conditions are mild and easy to control.
Drawings
FIG. 1 shows the preparation process of polysulfone membrane modified by acrylic acid and sulfonated dihydroxypropyl chitosan.
Detailed Description
The invention is further described with reference to the following figures and examples.
Example 1
Adding polysulfone membrane (PSF membrane) into 2% Acrylic Acid (AA) water solution for 30 min; taking out the polysulfone membrane or keeping the polysulfone membrane in the original solution, continuously irradiating for 5min under a 160W ultraviolet lamp, taking out, washing with absolute ethyl alcohol and deionized water, and drying under vacuum at 50 ℃ to obtain the AA-PSF membrane;
adding the AA-PSF membrane into an acetic acid buffer solution with the concentration of carbodiimide (EDC) of 3mmoL/L at 4 ℃ for 4 hours to activate carboxyl on the surface of the membrane; then washing with phosphate buffer solution and deionized water in sequence, adding the activated membrane into acetic acid solution of SDHPCS at 4 ℃ and 0.1mg/mL, and stirring for reaction for 20 h; soaking the obtained membrane in 2mmoL/L glutaraldehyde solution at 30 ℃ for 60min, then washing with phosphate buffer solution and deionized water, soaking in deionized water for 12h, and drying at normal temperature in vacuum to obtain the SDHPCS-AA-PSF membrane.
Example 2
Adding polysulfone membrane (PSF membrane) into 2% Acrylic Acid (AA) water solution for 30 min; taking out the polysulfone membrane or keeping the polysulfone membrane in the original solution, continuously irradiating for 10min under a 180W ultraviolet lamp, taking out, washing with absolute ethyl alcohol and deionized water, and drying under vacuum at 50 ℃ to obtain the AA-PSF membrane;
adding the AA-PSF membrane into an acetic acid buffer solution with the concentration of carbodiimide (EDC) of 3mmoL/L at 4 ℃ for 4 hours to activate carboxyl on the surface of the membrane; then washing with phosphate buffer solution and deionized water in sequence, adding the activated membrane into acetic acid solution of SDHPCS at 4 ℃ and 0.2mg/mL, and stirring for reaction for 20 h; soaking the obtained membrane in 2mmoL/L glutaraldehyde solution at 30 ℃ for 60min, then washing with phosphate buffer solution and deionized water, soaking in deionized water for 12h, and drying at normal temperature in vacuum to obtain the SDHPCS-AA-PSF membrane.
Example 3
Adding polysulfone membrane (PSF membrane) into 3% Acrylic Acid (AA) water solution for 30 min; taking out the polysulfone membrane or keeping the polysulfone membrane in the original solution, continuously irradiating for 8min under a 200W ultraviolet lamp, taking out, washing with absolute ethyl alcohol and deionized water, and drying under vacuum at 50 ℃ to obtain the AA-PSF membrane;
adding the AA-PSF membrane into an acetic acid buffer solution with the concentration of carbodiimide (EDC) of 3mmoL/L at 4 ℃ for 4 hours to activate carboxyl on the surface of the membrane; then washing with phosphate buffer solution and deionized water in sequence, adding the activated membrane into acetic acid solution of SDHPCS at 4 ℃ and 0.2mg/mL, and stirring for reaction for 20 h; soaking the obtained membrane in 2mmoL/L glutaraldehyde solution at 30 ℃ for 60min, then washing with phosphate buffer solution and deionized water, soaking in deionized water for 12h, and drying at normal temperature in vacuum to obtain the SDHPCS-AA-PSF membrane.
Example 4
Adding polysulfone membrane (PSF membrane) into 3% Acrylic Acid (AA) water solution for 30 min; taking out the polysulfone membrane or keeping the polysulfone membrane in the original solution, continuously irradiating for 6min under a 240W ultraviolet lamp, taking out, washing with absolute ethyl alcohol and deionized water, and drying under vacuum at 50 ℃ to obtain the AA-PSF membrane;
adding the AA-PSF membrane into an acetic acid buffer solution with the concentration of carbodiimide (EDC) of 3mmoL/L at 4 ℃ for 4 hours to activate carboxyl on the surface of the membrane; then washing with phosphate buffer solution and deionized water in sequence, adding the activated membrane into acetic acid solution of SDHPCS at 4 ℃ and 0.1mg/mL, and stirring for reaction for 20 h; soaking the obtained membrane in 2mmoL/L glutaraldehyde solution at 30 ℃ for 60min, then washing with phosphate buffer solution and deionized water, soaking in deionized water for 12h, and drying at normal temperature in vacuum to obtain the SDHPCS-AA-PSF membrane.
The properties of the acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membranes of the present invention are shown in table 1.
TABLE 1 modification of polysulfone membranes with acrylic acid and sulfonated dihydroxypropyl chitosan according to the present invention
Claims (1)
1. A preparation method of an acrylic acid and sulfonated dihydroxypropyl chitosan modified polysulfone membrane is characterized by comprising the following steps:
(1) acrylic modification of PSF film surface
Adding the polysulfone membrane into an acrylic acid aqueous solution with the mass concentration of 1-5% for 20-40 min; taking out the polysulfone membrane or leaving the polysulfone membrane in the original solution, and using a 150-300W ultraviolet lamp with the wavelength of 220-380 nm and the intensity of 20-30 mW/cm2Irradiating for 2-10 min, taking out, washing with absolute ethyl alcohol and deionized water, and then drying in vacuum at 40-50 ℃ to obtain an acrylic acid modified polysulfone membrane, namely an AA-PSF membrane;
(2) SDHPCS modification of AA-PSF membrane surfaces
Adding the AA-PSF film into an acetic acid buffer solution with the carbodiimide concentration of 2-4 mmoL/L at 4 ℃ for 3-5 hours to activate the carboxyl on the surface of the film; then, washing the membrane by using a phosphate buffer solution and deionized water in sequence, adding the activated membrane into an acetic acid solution of SDHPCS (sodium dehydrobutyrate succinate) at the temperature of 4 ℃ and at the concentration of 0.1-0.5 mg/mL, and stirring for reacting for 20-24 hours; soaking the obtained membrane in 1-2 mmoL/L glutaraldehyde solution at 20-40 ℃ for 50-60 min, then washing with phosphate buffer solution and deionized water, soaking in deionized water for 10-12 h, and drying in vacuum at normal temperature to obtain the SDHPCS-AA-PSF membrane, wherein the chemical structural formula is as follows:
wherein n = 20-80, m = 1-50; r is OH or sulfonated dihydroxypropyl chitosan.
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