CN114524952B - Preparation method of high-adhesion natural eggshell membrane chitosan hydrogel - Google Patents
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/36—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix
- A61L27/3604—Materials for grafts or prostheses or for coating grafts or prostheses containing ingredients of undetermined constitution or reaction products thereof, e.g. transplant tissue, natural bone, extracellular matrix characterised by the human or animal origin of the biological material, e.g. hair, fascia, fish scales, silk, shellac, pericardium, pleura, renal tissue, amniotic membrane, parenchymal tissue, fetal tissue, muscle tissue, fat tissue, enamel
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- A—HUMAN NECESSITIES
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/52—Hydrogels or hydrocolloids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
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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
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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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
- C08J2499/00—Characterised by the use of natural macromolecular compounds or of derivatives thereof not provided for in groups C08J2401/00 - C08J2407/00 or C08J2489/00 - C08J2497/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention belongs to medical hydrogel tissue engineering materials, and discloses a preparation method of a high-adhesion natural eggshell membrane chitosan hydrogel. According to the preparation method, 3- (3, 4-dihydroxyphenyl) propionic acid and p-carboxybenzaldehyde modified chitosan are utilized, and a natural material eggshell membrane is added to prepare the self-repairable high-adhesion hydrogel of HCA-pCBA-CS, namely the self-repairable high-adhesion natural eggshell membrane chitosan hydrogel, which also has certain mechanical strength, and the preparation method is simple and effective and is simple and convenient to operate.
Description
Technical Field
The invention belongs to medical hydrogel tissue engineering materials, and relates to a preparation method of a high-adhesion natural eggshell membrane chitosan hydrogel.
Background
The skin plays an indispensable role in protecting various organs of a human body and resisting external bad factors, and the skin is extremely easy to suffer from physical injuries such as burns, injuries, scratches and the like, so that bleeding is caused, and the human body forms a clot on a wound surface through platelets and blood coagulation factors, so that the aim of hemostasis is achieved. Common bandages, band-aids and the like in life have poor adhesiveness and expansibility, and practical application is limited. In recent years, hydrogels with unique three-dimensional structures have been widely used as wound dressings, with porous three-dimensional network structures facilitating the diffusion and penetration of liquid molecules, and moist environments facilitating wound healing. Chitosan is widely used for preparing hydrogel materials due to the characteristics of biocompatibility, biodegradability, hemostasis, antibacterial property and the like, and chitosan hydrogel has self-repairing performance and adhesiveness and is widely used as a hemostatic material. However, chitosan hydrogel synthesized by natural materials has poor mechanical properties, which limits its clinical application. While the traditional synthetic polymer hydrogel has better performances of water absorption swelling, mechanical strength and the like, but has poor biocompatibility and cytotoxicity.
Disclosure of Invention
In view of the above, the present invention aims to provide a preparation method of a high-adhesion natural eggshell membrane chitosan hydrogel, which utilizes 3- (3, 4-dihydroxyphenyl) propionic acid and p-carboxybenzaldehyde to modify chitosan, and adds a natural material eggshell membrane to prepare a high-adhesion hydrogel capable of self-repairing HCA-pCBA-CS, and has certain mechanical strength, and the preparation method is simple and effective, and is easy and convenient to operate.
The invention provides a preparation method of a high-adhesion natural eggshell membrane chitosan hydrogel, which comprises the following steps:
s1, dissolving chitosan with acetic acid to obtain a chitosan solution, dissolving p-carboxybenzaldehyde with absolute ethyl alcohol to obtain a p-carboxybenzaldehyde solution, dripping a mixed solution of EDC and NHS into the p-carboxybenzaldehyde solution, reacting for 15-30 minutes at low temperature, dripping the chitosan solution, and reacting for 30 minutes at low temperature to obtain a reaction solution;
s2, dripping a 3- (3, 4-dihydroxyphenyl) propionic acid solution into a reaction solution, dripping a mixed solution of EDC and NHS into the reaction solution, performing low-temperature reaction for half an hour, vacuumizing, performing nitrogen protection, performing reaction for 8-12 hours under the anaerobic low-temperature condition, dialyzing for 3 days, and performing freeze drying to obtain purified HCA-pCBA-CS;
s3, soaking eggshell membranes in a sodium periodate solution, performing light-shielding reaction for 8-12 hours, and grinding the eggshell membranes into powder by using liquid nitrogen to obtain oxidized eggshell membrane powder;
s4, dissolving HCA-pCBA-CS and the eggshell membrane powder in deionized water, stirring and standing to obtain the high-adhesion natural eggshell membrane chitosan hydrogel.
Further, in step S1, the concentration of the acetic acid solution is 20 mu L/mL; the concentration of the chitosan solution is 5-10mg/mL; the concentration of the p-carboxybenzaldehyde solution is 5-10mg/mL.
Further, in step S1, the dosage ratio of the chitosan solution, the p-carboxybenzaldehyde solution and the mixed solution of EDC and NHS is 100ml to 5ml to 3ml.
Further, in the mixed solution of EDC and NHS, the concentration of EDC is 172.5-345mg/mL, and the concentration of NHS is 57.5-115mg/mL.
Further, in the step S2, the concentration of the 3- (3, 4-dihydroxyphenyl) propionic acid solution is 44-88mg/mL.
Further, in step S2, the dosage ratio of the 3- (3, 4-dihydroxyphenyl) propionic acid solution to the mixed solution of EDC and NHS is 5mL to 3mL.
Further, in step S2, the dialysis specifically includes: dialysis was performed with 0.01M aqueous sodium chloride for 3 days.
Further, in step S3, the concentration of the sodium periodate solution is 35mg/mL.
Further, in the step S4, the addition amount of HCA-pCBA-CS in every 1mL of deionized water is 30-50mg, and the addition amount of the eggshell membrane powder is 1-2mg.
Compared with the prior art, the invention has the following advantages:
(1) The self-repairing, high-adhesion and stretchable functions of the hydrogel are provided by the dynamic reversible Schiff base bond between 3- (3, 4-dihydroxyphenyl) propionic acid, p-carboxybenzaldehyde and chitosan based on the self-assembly technology;
(2) The addition of the natural material eggshell membrane enhances the mechanical properties of the hydrogel;
(3) The method is simple and effective, and is simple and convenient to operate;
(4) The preparation device is simple and does not need special equipment;
(5) The self-repairable, stretchable and high-adhesion hydrogel prepared by the method has a good self-repairable effect, has high-adhesion, stretchable and hemostatic functions and the like, and has excellent application prospects in the field of tissue engineering.
Drawings
FIG. 1 is a schematic illustration of a high adhesion natural eggshell membrane chitosan hydrogel prepared in example 1;
FIG. 2 is a schematic self-repairing diagram of the high-adhesion natural eggshell membrane chitosan hydrogel prepared in example 1;
fig. 3 is a schematic illustration of the adhesion of the high adhesion natural eggshell membrane chitosan hydrogel prepared in example 1.
Detailed Description
For a further understanding of the present invention, preferred embodiments of the invention are described below in conjunction with the examples, but it should be understood that these descriptions are merely intended to illustrate further the features and advantages of the invention and are not limiting of the patent claims of the invention.
Example 1
1) Dissolving 1g of chitosan in 100mL of 20 mu L/mL of acetic acid to obtain a chitosan solution with the concentration of 10mg/mL, dissolving 100mg of p-carboxybenzaldehyde in 10mL of absolute ethyl alcohol to obtain a p-carboxybenzaldehyde solution with the concentration of 10mg/mL, dripping 3mL of a mixed solution of 345mg/mL EDC and 115mg/mL NHS into the p-carboxybenzaldehyde solution, reacting for 15-30 minutes at low temperature, dripping the chitosan solution, and reacting for 30 minutes at low temperature to obtain a reaction solution;
2) Dropwise adding 5mL of a 88mg/mL 3- (3, 4-dihydroxyphenyl) propionic acid solution into the reaction solution, adding 3mL of a mixed solution of 230mg/mL EDC and 115mg/mL NHS into the reaction solution, reacting for half an hour at low temperature, vacuumizing, protecting with nitrogen, reacting for 8-12h under the condition of anaerobic low temperature, dialyzing for 3 days with a 0.01M sodium chloride aqueous solution, and freeze-drying to obtain purified HCA-pCBA-CS;
3) Soaking eggshell membrane in 40mL of 35mg/mL sodium periodate solution, performing light-shielding reaction for 8-12h, and grinding eggshell membrane into powder by using liquid nitrogen to obtain oxidized eggshell membrane powder;
4) 30mg of HCA-pCBA-CS and 1mg of the oxidized eggshell membrane powder were dissolved in 1mL of deionized water, stirred and allowed to stand to obtain a highly adherent natural eggshell membrane chitosan hydrogel, as shown in FIG. 1.
Half of the prepared high-adhesion natural eggshell membrane chitosan hydrogel is dyed with ink, and is self-repaired into a complete piece, and the complete piece can be lifted by forceps, and the specific process is shown in figure 2.
The prepared high-adhesion natural eggshell membrane chitosan hydrogel is used for adhering the lung, liver, heart, test tube cover, rubber and gauze of a mouse, the adhesion condition is shown in figure 3, the upper row of the adherends in the figure is from left to right, the lung, liver and heart of the mouse are respectively arranged in the lower row of the adherends from left to right, and the test tube cover, rubber and gauze are respectively arranged in the lower row of the adherends from left to right, so that the adhesion force is good as can be seen from figure 3.
Example 2
1) Dissolving 0.5g chitosan in 100mL of 20 mu L/mL acetic acid to obtain a chitosan solution with the concentration of 5mg/mL, dissolving 50mg of p-carboxybenzaldehyde in 10mL absolute ethyl alcohol to obtain a p-carboxybenzaldehyde solution with the concentration of 5mg/mL, dripping 3mL of a mixed solution of 172.5mg/mL EDC and 57.5mg/mL NHS into the p-carboxybenzaldehyde solution, reacting for 15-30 minutes at low temperature, dripping the chitosan solution, and reacting for 30 minutes at low temperature to obtain a reaction solution;
2) Dropwise adding 5mL of a 44mg/mL3- (3, 4-dihydroxyphenyl) propionic acid solution into the reaction solution, adding 3mL of a mixed solution of 115mg/mL EDC and 57.5mg/mL NHS into the reaction solution, carrying out low-temperature reaction for half an hour, vacuumizing, protecting by nitrogen, reacting for 8-12 hours under the condition of anaerobic low temperature, dialyzing for 3 days by using a 0.01M sodium chloride aqueous solution, and freeze-drying to obtain purified HCA-pCBA-CS;
3) Soaking eggshell membrane in 20mL of 35mg/mL sodium periodate solution, performing light-shielding reaction for 8-12h, and grinding the eggshell membrane into powder by using liquid nitrogen to obtain oxidized eggshell membrane powder;
4) 30mg of HCA-pCBA-CS and 1mg of the eggshell membrane powder were dissolved in 1mL of deionized water, stirred and allowed to stand to obtain a highly adhesive natural eggshell membrane chitosan hydrogel.
Example 3
1) Dissolving 1g of chitosan in 100mL of 20 mu L/mL of acetic acid to obtain a chitosan solution with the concentration of 10mg/mL, dissolving p-carboxybenzaldehyde in 10mL of absolute ethyl alcohol to obtain a p-carboxybenzaldehyde solution with the concentration of 10mg/mL, dripping 3mL of a mixed solution of 345mg/mL EDC and 115mg/mL NHS into the p-carboxybenzaldehyde solution, performing low-temperature reaction for 15-30 minutes, dripping the chitosan solution, and performing low-temperature reaction for 30 minutes to obtain a reaction solution;
2) Dropwise adding 5mL of a 88mg/mL 3- (3, 4-dihydroxyphenyl) propionic acid solution into the reaction solution, adding 3mL of a mixed solution of 230mg/mL EDC and 115mg/mL NHS into the reaction solution, reacting for half an hour at low temperature, vacuumizing, protecting with nitrogen, reacting for 8-12h under the condition of anaerobic low temperature, dialyzing for 3 days with a 0.01M sodium chloride aqueous solution, and freeze-drying to obtain purified HCA-pCBA-CS;
3) Soaking eggshell membrane in 20mL of 35mg/mL sodium periodate solution, performing light-shielding reaction for 8-12h, and grinding the eggshell membrane into powder by using liquid nitrogen to obtain oxidized eggshell membrane powder;
4) 50mg of HCA-pCBA-CS and 2mg of the eggshell membrane powder are dissolved in 1mL of deionized water, stirred and then stood still, and the high-adhesion natural eggshell membrane chitosan hydrogel is obtained.
The above description of the method for preparing a highly adherent natural eggshell membrane chitosan hydrogel provided by the present invention has been provided in detail, and specific examples are provided herein to illustrate the principles and embodiments of the present invention, and the above examples are provided to facilitate an understanding of the method of the present invention and its core ideas, including the best mode, and to enable any person skilled in the art to practice the present invention, including making and using any devices or systems, and to practice any incorporated methods. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the invention can be made without departing from the principles of the invention and these modifications and adaptations are intended to be within the scope of the invention as defined in the following claims. The scope of the patent protection is defined by the claims and may include other embodiments that occur to those skilled in the art. Such other embodiments are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements with insubstantial differences from the literal language of the claims.
Claims (10)
1. The preparation method of the high-adhesion natural eggshell membrane chitosan hydrogel is characterized by comprising the following steps of:
s1, dissolving chitosan with acetic acid to obtain a chitosan solution, dissolving p-carboxybenzaldehyde with absolute ethyl alcohol to obtain a p-carboxybenzaldehyde solution, dripping a mixed solution of EDC and NHS into the p-carboxybenzaldehyde solution, reacting for 15-30 minutes at low temperature, dripping the chitosan solution, and reacting for 30 minutes at low temperature to obtain a reaction solution;
s2, dripping a 3- (3, 4-dihydroxyphenyl) propionic acid solution into a reaction solution, dripping a mixed solution of EDC and NHS into the reaction solution, performing low-temperature reaction for half an hour, vacuumizing, performing nitrogen protection, performing reaction for 8-12 hours under the anaerobic low-temperature condition, dialyzing for 3 days, and performing freeze drying to obtain purified HCA-pCBA-CS;
s3, soaking eggshell membranes in a sodium periodate solution, performing light-shielding reaction for 8-12 hours, and grinding the eggshell membranes into powder by using liquid nitrogen to obtain oxidized eggshell membrane powder;
s4, dissolving HCA-pCBA-CS and the eggshell membrane powder in deionized water, stirring and standing to obtain the high-adhesion natural eggshell membrane chitosan hydrogel.
2. The method according to claim 1, wherein in step S1, the concentration of the acetic acid solution is 20 μl/mL; the concentration of the chitosan solution is 5-10mg/mL; the concentration of the p-carboxybenzaldehyde solution is 5-10mg/mL.
3. The method according to claim 1, wherein the chitosan solution, the p-carboxybenzaldehyde solution and the mixed solution of EDC and NHS are used in the ratio of 100ml to 5ml to 3ml in step S1.
4. The method of claim 1, wherein in step S1, the concentration of EDC in the mixed solution of EDC and NHS is 172.5-345mg/mL, and the concentration of NHS is 57.5-115mg/mL.
5. The method according to claim 1, wherein in step S2, the concentration of EDC in the mixed solution of EDC and NHS is 115-230mg/mL and the concentration of NHS is 57.5-115mg/mL.
6. The method according to claim 5, wherein the concentration of the 3- (3, 4-dihydroxyphenyl) propionic acid solution in step S2 is 44-88mg/mL.
7. The process according to claim 6, wherein in step S2, the ratio of the 3- (3, 4-dihydroxyphenyl) propionic acid solution to the mixed solution of EDC and NHS is 5 mL/3 mL.
8. The method according to claim 1, wherein in step S2, the dialysis is specifically: dialysis was performed with 0.01M aqueous sodium chloride for 3 days.
9. The method according to claim 1, wherein the concentration of the sodium periodate solution in step S3 is 35mg/mL.
10. The method of claim 1, wherein in step S4, the amount of HCA-pCBA-CS added is 30-50mg and the amount of eggshell membrane powder added is 1-2mg per 1mL deionized water.
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| CN101829545A (en) * | 2010-05-12 | 2010-09-15 | 北京航空航天大学 | Heavy metal biological adsorbent using eggshell membrane as matrix and preparation method thereof |
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| CN111228040A (en) * | 2020-01-08 | 2020-06-05 | 河南亚都实业有限公司 | Absorbable anti-adhesion dressing and preparation method thereof |
| CN113248737A (en) * | 2021-06-11 | 2021-08-13 | 南通大学 | Preparation method of self-repairing antibacterial hydrogel |
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| CN101829545A (en) * | 2010-05-12 | 2010-09-15 | 北京航空航天大学 | Heavy metal biological adsorbent using eggshell membrane as matrix and preparation method thereof |
| CN107966560A (en) * | 2017-11-22 | 2018-04-27 | 江南大学 | A kind of preparation method of the immunosensor based on chitosan-gold hybrid particle |
| CN111228040A (en) * | 2020-01-08 | 2020-06-05 | 河南亚都实业有限公司 | Absorbable anti-adhesion dressing and preparation method thereof |
| CN113248737A (en) * | 2021-06-11 | 2021-08-13 | 南通大学 | Preparation method of self-repairing antibacterial hydrogel |
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