CN116392630A - Injectable hydrogel for repairing diabetic wound surface and preparation method thereof - Google Patents
Injectable hydrogel for repairing diabetic wound surface and preparation method thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title abstract description 8
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- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0028—Polypeptides; Proteins; Degradation products thereof
- A61L26/0047—Specific proteins or polypeptides not covered by groups A61L26/0033 - A61L26/0042
-
- 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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0019—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0028—Polypeptides; Proteins; Degradation products thereof
- A61L26/0033—Collagen
-
- 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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0028—Polypeptides; Proteins; Degradation products thereof
- A61L26/0038—Gelatin
-
- 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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/0066—Medicaments; Biocides
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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
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/008—Hydrogels or hydrocolloids
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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
- A61L2400/06—Flowable or injectable implant compositions
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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
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Abstract
The invention belongs to the technical field of functional materials, and particularly relates to an injectable hydrogel for repairing diabetic wounds and a preparation method thereof. The injectable hydrogel for repairing the diabetic wound surface comprises the following active components in percentage by mass: 30% -75% of protein source compound and 30% -80% of aldehyde polymer. The injectable hydrogel provided by the invention has pH responsiveness, can be cured in situ, can cover a wound in a gapless fit manner, and provides a closed barrier for the wound. The hydrogel of the invention has strong adhesiveness to skin after solidification, has self-healing property, can not cause the falling of the hydrogel due to movement, has good moisturizing effect, good biocompatibility, no cytotoxicity, can exchange with tissue fluid, can better promote the growth and proliferation of cells, and has the effect of accelerating wound healing.
Description
Technical Field
The invention belongs to the technical field of functional materials, and particularly relates to an injectable hydrogel for repairing diabetic wounds and a preparation method thereof.
Background
Wound healing is a coordinated and orderly cascade of reactions, and improper intervention may cause delayed wound healing. The diabetic wound surface is difficult to heal by itself due to the reasons of metabolic disorder, impaired immune function, nerve reaction retardation and the like of a diabetic patient, the course of the disease is long, various complications are easily caused by acute or chronic wound surface caused by diabetes, such as slow healing, and the occurrence and treatment of the diabetic wound surface are increasingly serious social problems due to heavy burden on patients, medical systems and socioeconomic. On the basis of surgical debridement and local medication, the external dressing is developed to relieve the pain of patients and shorten the course of disease, thus having important clinical significance and application prospect.
At present, a dressing for healing a diabetic wound surface is proposed in the prior art, and most traditional dressings are dry patches in order to fully absorb liquid garbage generated by the wound surface, but the local environment which is too dry is not beneficial to the growth recovery of subsequent tissue cells. In addition, the traditional dressing is generally sewn for convenient fixation, which undoubtedly increases secondary injury and is unfavorable for wound repair. In addition, conventional dressings do not completely cover the wound site, with the risk of infection from the exposed wound. The traditional dressing has unsatisfactory treatment effect, and diabetes wound infection has an increasing trend every year, so that a novel functional dressing which has no toxicity to healthy tissue cells and is easy to use is necessary to be developed, and the accelerated healing of the diabetes wound is realized.
Disclosure of Invention
The first object of the present invention is to provide an injectable hydrogel for repairing diabetic wound, and the second object of the present invention is to provide a method for preparing the injectable hydrogel.
According to a first aspect of the present invention, there is provided an injectable hydrogel for diabetic wound repair, comprising, in mass percent, active ingredients: 30% -75% of protein source compound and 30% -80% of aldehyde polymer.
In some embodiments, the active ingredients comprise, in mass percent: 40% -60% of protein source compound and 40% -70% of aldehyde polymer.
In some embodiments, the protein source compound is any one of collagen, gelatin, silk fibroin, or recombinant protein. Preferably, the protein source compound is gelatin. The protein source compound can provide sufficient amino groups, can generate chemical crosslinking reaction with the aldehyde polymer to form a hydrogel network for gelling, and has good mechanical elasticity and biocompatibility, so that the prepared hydrogel has good mechanical elasticity and biocompatibility. The mechanical strength of the gelatin is better, the mechanical property and stability of the hydrogel can be improved, and the gelatin is easier to gel.
In some embodiments, the aldehyde polymer is an aldehyde polyethylene glycol. The aldehyde polyethylene glycol can promote chemical crosslinking reaction, and meanwhile, the main chain polyethylene glycol of the aldehyde polyethylene glycol has good hydrophilic performance and good swelling effect, so that the absorption of wound waste liquid can be accelerated.
In some embodiments, the aldehyde polyethylene glycol is prepared from p-aldehyde benzoic acid and polyethylene glycol by an esterification reaction.
In some embodiments, the polyethylene glycol has a weight average molecular weight of 2000-10000Da. The mechanical property and the hydrophilic property of polyethylene glycol have a great relation with the polymerization degree, the higher the molecular weight is, the higher the hydrophilic property is, the more complex the network is, the gel formation is easier, and the hydrophilic property and the mechanical property of the obtained hydrogel are also better.
According to a second aspect of the present invention, there is provided a method for preparing the injectable hydrogel for repairing diabetic wounds, comprising the steps of:
s1, respectively dissolving a protein source compound and an aldehyde polymer in water to prepare a protein source compound aqueous solution and an aldehyde polymer aqueous solution;
s2, uniformly mixing the protein source compound aqueous solution and the aldehyde polymer aqueous solution in equal volume to obtain a mixed solution;
s3, adjusting the pH value of the mixed solution to 6-8 to form hydrogel, and performing injection extrusion molding after gel formation to obtain the injectable hydrogel.
In some embodiments, in step S1, the mass percentage of the protein source compound in the aqueous solution of the protein source compound is 1% to 10%.
In some embodiments, in step S1, the mass percent of the hydroformylation polymer in the aqueous solution of the hydroformylation polymer is from 1% to 10%.
Compared with the prior art, the invention has the beneficial effects that:
(1) The injectable hydrogel for repairing the diabetic wound surface has pH responsiveness, can be cured in situ, is covered by gapless anastomosis with the wound, provides a closed barrier for the wound, and achieves the aim of minimally invasive treatment.
(2) The hydrogel has strong adhesiveness to skin after being solidified, has self-healing property, can not fall off the hydrogel due to movement, does not need to be sutured again in the use process, is more convenient to use, and avoids secondary damage caused by suture lines.
(3) The hydrogel of the invention has good moisturizing effect after solidification, good biocompatibility, no cytotoxicity, capability of exchanging with tissue fluid, better promotion of cell ingrowth and proliferation, and wound healing acceleration.
Detailed Description
The present invention will be described in further detail with reference to the following examples, which are to be construed as merely illustrative, and not a limitation of the scope of the present invention. The process steps not disclosed in the examples are prior art. Unless otherwise specified, the following materials are all commercially available.
Example 1
The preparation method of the injectable hydrogel for repairing the diabetic wound surface of the embodiment comprises the following steps:
(1) 0.5g of p-aldehyde benzoic acid, 1.6g of polyethylene glycol with a molecular weight of 4000Da and 0.025g of 4-dimethylaminopyridine are dissolved in 100mL of tetrahydrofuran and cooled to 0 ℃ to obtain a mixed solution; 0.084g of N, N' -dicyclohexylcarbodiimide is dissolved in 100mL of tetrahydrofuran, and is added into the mixed solution dropwise under the protection of nitrogen, the mixture is stirred and reacts for 20 hours at 20 ℃, the reaction product is filtered and washed by tetrahydrofuran, and then is precipitated in diethyl ether to obtain the hydroformylation polyethylene glycol.
(2) Respectively dissolving gelatin and aldehyde polyethylene glycol in water to prepare gelatin aqueous solution with the mass fraction of 10% and aldehyde polyethylene glycol aqueous solution with the mass fraction of 6%.
(3) Uniformly mixing gelatin aqueous solution and aldehyde polyethylene glycol aqueous solution in equal volume to obtain mixed solution.
(4) The pH of the mixed solution is adjusted to 7 to form hydrogel, and the hydrogel is formed by injection extrusion molding after gel formation, so as to obtain the injectable hydrogel.
Example 2
The preparation method of the injectable hydrogel for repairing the diabetic wound surface of the embodiment comprises the following steps:
(1) 0.5g of p-aldehyde benzoic acid, 1.6g of polyethylene glycol with a molecular weight of 4000Da and 0.025g of 4-dimethylaminopyridine are dissolved in 100mL of tetrahydrofuran and cooled to 0 ℃ to obtain a mixed solution; 0.084g of N, N' -dicyclohexylcarbodiimide is dissolved in 100mL of tetrahydrofuran, and is added into the mixed solution dropwise under the protection of nitrogen, the mixture is stirred and reacts for 20 hours at 20 ℃, the reaction product is filtered and washed by tetrahydrofuran, and then is precipitated in diethyl ether to obtain the hydroformylation polyethylene glycol.
(2) Respectively dissolving gelatin and aldehyde polyethylene glycol in water to prepare gelatin aqueous solution with the mass fraction of 10% and aldehyde polyethylene glycol aqueous solution with the mass fraction of 10%.
(3) Uniformly mixing gelatin aqueous solution and aldehyde polyethylene glycol aqueous solution in equal volume to obtain mixed solution.
(4) The pH of the mixed solution is adjusted to 7 to form hydrogel, and the hydrogel is formed by injection extrusion molding after gel formation, so as to obtain the injectable hydrogel.
Example 3
The preparation method of the injectable hydrogel for repairing the diabetic wound surface of the embodiment comprises the following steps:
(1) 0.5g of p-aldehyde benzoic acid, 1.6g of polyethylene glycol with a molecular weight of 4000Da and 0.025g of 4-dimethylaminopyridine are dissolved in 100mL of tetrahydrofuran and cooled to 0 ℃ to obtain a mixed solution; 0.084g of N, N' -dicyclohexylcarbodiimide is dissolved in 100mL of tetrahydrofuran, and is added into the mixed solution dropwise under the protection of nitrogen, the mixture is stirred and reacts for 20 hours at 20 ℃, the reaction product is filtered and washed by tetrahydrofuran, and then is precipitated in diethyl ether to obtain the hydroformylation polyethylene glycol.
(2) Respectively dissolving gelatin and aldehyde polyethylene glycol in water to prepare a gelatin aqueous solution with the mass fraction of 6% and an aldehyde polyethylene glycol aqueous solution with the mass fraction of 6%.
(3) Uniformly mixing gelatin aqueous solution and aldehyde polyethylene glycol aqueous solution in equal volume to obtain mixed solution.
(4) The pH of the mixed solution is adjusted to 7 to form hydrogel, and the hydrogel is formed by injection extrusion molding after gel formation, so as to obtain the injectable hydrogel.
Example 4
The preparation method of the injectable hydrogel for repairing the diabetic wound surface of the embodiment comprises the following steps:
(1) 0.5g of p-aldehyde benzoic acid, 1.6g of polyethylene glycol with molecular weight of 10000Da and 0.025g of 4-dimethylaminopyridine are dissolved in 100mL of tetrahydrofuran, and cooled to 0 ℃ to obtain a mixed solution; 0.084g of N, N' -dicyclohexylcarbodiimide is dissolved in 100mL of tetrahydrofuran, and is added into the mixed solution dropwise under the protection of nitrogen, the mixture is stirred and reacts for 20 hours at 20 ℃, the reaction product is filtered and washed by tetrahydrofuran, and then is precipitated in diethyl ether to obtain the hydroformylation polyethylene glycol.
(2) Respectively dissolving gelatin and aldehyde polyethylene glycol in water to prepare gelatin aqueous solution with the mass fraction of 10% and aldehyde polyethylene glycol aqueous solution with the mass fraction of 6%.
(3) Uniformly mixing gelatin aqueous solution and aldehyde polyethylene glycol aqueous solution in equal volume to obtain mixed solution.
(4) The pH of the mixed solution is adjusted to 7 to form hydrogel, and the hydrogel is formed by injection extrusion molding after gel formation, so as to obtain the injectable hydrogel.
In the following, to verify the performance of the injectable hydrogels for diabetic wound repair of the present invention, the following performance tests were performed on the injectable hydrogels of examples 1 to 4.
The curing time of the hydrogel is detected by an inversion method, and specifically comprises the following steps: adding the mixed solution obtained by uniformly mixing gelatin aqueous solution and aldehyde polyethylene glycol aqueous solution in equal volume into an ep tube, regulating the pH value of the mixed solution to 7, starting timing, inverting the ep tube, ending when the solution does not flow, and obtaining the curing time according to the time difference between the ending and the starting of timing.
The adhesive strength of the hydrogel was tested by pig skin shoulder-building, specifically: removing excessive grease from two clean pigskins, dripping hydrogel on one piece of pigskin, spreading, covering the hydrogel area with another piece of pigskin, stretching the two pieces of pigskin along the 180-degree direction by a universal tensile testing machine after the hydrogel is solidified until the two pieces of pigskin are separated, recording corresponding stress-strain curves, and calculating the adhesive strength.
The elastic modulus of the hydrogel after curing is detected by a universal tensile tester, and is specifically as follows: and (3) dropwise adding the hydrogel into a mould, stretching downwards by using a universal tensile testing machine until the hydrogel breaks after solidification and molding, recording a stress-strain curve of response, and calculating the slope of the curve at the initial stage to obtain the corresponding elastic modulus.
The water absorption swelling degree of the cured hydrogel sample immersed in deionized water is measured at room temperature, and specifically comprises the following steps: the sample was dried and weighed, denoted W0, then immersed in deionized water, taken out after swelling equilibrium was reached at room temperature, the water on the surface of the sample was removed, and weighed, denoted W1, and the swelling ratio = (W1-W0)/W0 x 100%.
The test results are shown in Table 1.
TABLE 1 Performance test results of injectable hydrogels prepared in examples 1-4
| Examples | Duration/min of cure | Adhesive strength/kPa | Modulus of elasticity/kPa | Swelling ratio/% |
| Example 1 | 5 | 12 | 0.8 | 1069 |
| Example 2 | 2 | 21 | 1.3 | 857 |
| Example 3 | 10 | 6 | 0.6 | 1385 |
| Example 4 | 4 | 18 | 0.98 | 896 |
The results in table 1 show that the hydrogel prepared from the aqueous gelatin solution with a mass fraction of 10% and the aqueous hydroformylation polyethylene glycol solution with a mass fraction of 10% of example 2 has the shortest curing time, the highest curing speed, and the highest adhesive strength and elastic modulus, thereby indicating that increasing the concentration of the aqueous gelatin solution can significantly improve the elastic modulus and adhesive strength of the hydrogel and shorten the curing time of the hydrogel. In addition, it can be seen that the swelling rate of the hydrogel is increased due to the strong hydrophilicity of the hydroformylation polyethylene glycol. The concentration of the aldehyde polyethylene glycol of example 2 was highest, but the swelling ratio of the hydrogel of example 2 was lowest, because the hydrogel of example 2 had a denser crosslinked network, more crosslinking points, and limited its volume swelling.
What has been described above is merely some of the specific embodiments of the present invention. It will be apparent to those skilled in the art that various modifications and improvements can be made without departing from the inventive concept of the present invention.
Claims (10)
1. The injectable hydrogel for repairing the diabetic wound is characterized by comprising the following active ingredients in percentage by mass: 30% -75% of protein source compound and 30% -80% of aldehyde polymer.
2. The injectable hydrogel for repairing diabetic wounds according to claim 1, wherein the active ingredients thereof comprise, in mass percent: 40% -60% of protein source compound and 40% -70% of aldehyde polymer.
3. The injectable hydrogel for diabetic wound repair of claim 1 or 2, wherein the protein source compound is any one of collagen, gelatin, silk fibroin or recombinant protein.
4. An injectable hydrogel for use in the repair of diabetic wounds according to claim 3, wherein the protein source compound is gelatin.
5. The injectable hydrogel for diabetic wound repair of claim 1 or 2, wherein the hydroformylation polymer is a hydroformylation polyethylene glycol.
6. The injectable hydrogel for repair of diabetic wounds according to claim 5, wherein the aldehyde-based polyethylene glycol is prepared from p-aldehyde benzoic acid and polyethylene glycol by esterification.
7. The injectable hydrogel for repair of diabetic wounds according to claim 6, wherein the polyethylene glycol has a weight average molecular weight of 2000-10000Da.
8. A method for preparing an injectable hydrogel for repair of diabetic wounds according to any of claims 1-7, comprising the steps of:
s1, respectively dissolving a protein source compound and an aldehyde polymer in water to prepare a protein source compound aqueous solution and an aldehyde polymer aqueous solution;
s2, uniformly mixing the protein source compound aqueous solution and the aldehyde polymer aqueous solution in equal volume to obtain a mixed solution;
s3, adjusting the pH value of the mixed solution to 6-8 to form hydrogel, and performing injection extrusion molding after gel formation to obtain the injectable hydrogel.
9. The method for preparing injectable hydrogel for diabetic wound repair according to claim 8, wherein in step S1, the mass percentage of the protein source compound in the aqueous solution of the protein source compound is 1% -10%.
10. The method for preparing an injectable hydrogel for repairing a diabetic wound according to claim 8, wherein in step S1, the mass percentage of the aldehyde-based polymer in the aqueous solution of the aldehyde-based polymer is 1% to 10%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117379362A (en) * | 2023-10-11 | 2024-01-12 | 首都医科大学附属北京潞河医院 | Angiopoietin-like protein 3 loaded hydrogel and preparation method and application thereof |
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| CN110947027A (en) * | 2019-11-27 | 2020-04-03 | 江南大学 | Bacteriostatic self-healing hydrogel dressing for promoting wound repair |
| CN111840631A (en) * | 2020-07-23 | 2020-10-30 | 青岛大学附属医院 | Injectable antibacterial hemostatic hydrogel adhesive and preparation method and application thereof |
| CN113354803A (en) * | 2021-06-10 | 2021-09-07 | 沈阳药科大学 | Polycarbonate/polyethylene glycol block copolymer containing aldehyde side group, injectable self-repairing hydrogel dressing and preparation method |
| CN115068684A (en) * | 2022-06-30 | 2022-09-20 | 华南理工大学 | Curcumin-loaded hydrogel for repairing chronic wounds of diabetes and preparation method thereof |
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| CN110947027A (en) * | 2019-11-27 | 2020-04-03 | 江南大学 | Bacteriostatic self-healing hydrogel dressing for promoting wound repair |
| CN111840631A (en) * | 2020-07-23 | 2020-10-30 | 青岛大学附属医院 | Injectable antibacterial hemostatic hydrogel adhesive and preparation method and application thereof |
| CN113354803A (en) * | 2021-06-10 | 2021-09-07 | 沈阳药科大学 | Polycarbonate/polyethylene glycol block copolymer containing aldehyde side group, injectable self-repairing hydrogel dressing and preparation method |
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