CN114891242A - Developable hydrogel and preparation method thereof - Google Patents
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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
- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/145—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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/18—Materials at least partially X-ray or laser opaque
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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
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/02—Polyalkylene oxides
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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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Abstract
The invention relates to a developable hydrogel, wherein iodine-containing polyethylene glycol in a first phase solution is 4-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 4-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, and an amino compound in a second phase solution is trilysine, polyethyleneimine, four-arm aminopolyethylene glycol or eight-arm aminopolyethylene glycol. The invention also relates to a preparation method of the developable hydrogel. The developable hydrogel is prepared by mixing two different liquids, namely a first phase solution and a second phase solution, and polymerizing the two liquids to form the hydrogel after being used, can be closely attached to tissues and can be developed under X rays.
Description
Technical Field
The present invention relates to biomaterials, and more particularly to a developable hydrogel and a method for preparing the same.
Background
Hydrogels are a class of polymers having a three-dimensional network structure of hydrophilic groups, which can be swollen but are insoluble in water and can maintain a certain shape due to the physical and chemical crosslinking between the polymers. Meanwhile, the hydrogel has excellent physical and chemical properties and biological characteristics, such as biocompatibility, high elasticity, swelling property and the like, and is widely applied to the fields of medicines, tissue engineering and medical instruments.
The materials used for preparing the hydrogel include chitosan, alginate, polyethylene glycol and the like. Polyethylene glycol is a high molecular polymer, has good biocompatibility and safety, can be used as a medicinal auxiliary material, modifies the end group of polyethylene glycol, not only increases the performance of the polyethylene glycol into hydrogel, but also retains the original safety characteristic of polyethylene glycol, and is an ideal hydrogel material.
There are reported a method of using polyethylene glycol succinimidyl ester, polylysine and polyethyleneimine to form hydrogel, and a method of using aldehyde-terminated polyethylene glycol and aminopolyethylene glycol to polymerize hydrogel, but none of the above hydrogels has a function and characteristics of being developable under X-rays. The implantation position of the hydrogel cannot be observed in real time when the hydrogel is used by a doctor, so that the operation level of the doctor is high, and the patient also bears greater risk of ectopic implantation.
Disclosure of Invention
In order to solve the problems that the hydrogel in the prior art is not developed under X-rays and the like, the invention provides a developable hydrogel and a preparation method thereof.
The developable hydrogel is formed by polymerizing a first phase solution and a second phase solution, wherein the first phase solution is formed by dissolving iodine-containing polyethylene glycol (PEG-TIBSG) in a first buffer solution, the iodine-containing polyethylene glycol (PEG-TIBSG) is four-arm iodine-containing polyethylene glycol (4-arm-PEG-TIBSG) or eight-arm iodine-containing polyethylene glycol (8-arm-PEG-TIBSG), the four-arm iodine-containing polyethylene glycol (4-arm-PEG-TIBSG) is 4-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 4-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, the eight-arm iodine-containing polyethylene glycol (8-arm-PEG-TIBSG) is 8-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, the second phase solution being formed by dissolving an amino compound in a second buffer solution, the amino compound being trilysine, polyethyleneimine or aminopolyethylene glycol (PEG-NH2), the aminopolyethylene glycol (PEG-NH2) being tetra-arm aminopolyethylene glycol (4-arm-PEG-NH 2) or eight-arm aminopolyethylene glycol (8-arm-PEG-NH 2).
The inventors of the present application finally selected to polymerize from 4-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 4-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate in the first phase solution and from trilysine, polyethyleneimine, four-arm aminopolyethylene glycol (4-arm-PEG-NH 2) or eight-arm aminopolyethylene glycol (8-arm-PEG-NH 2) in the second phase solution by a great amount of creative work, can satisfy the effect of forming hydrogel which can be developed under X-ray by polymerization.
Preferably, the ratio of the molar amount of iodine-containing groups in the iodine-containing polyethylene glycol and amino groups in the amino compound is between 1: 1-3.
Preferably, 1-2 arms of the four-arm iodine-containing polyethylene glycol (4-arm-PEG-TIBSG) are grafted with iodine-containing groups, and 1-4 arms of the eight-arm iodine-containing polyethylene glycol (8-arm-PEG-TIBSG) are grafted with iodine-containing groups.
Preferably, the mass percentage concentration of the first phase solution is between 1.0% and 20%.
Preferably, the PH of the first buffer solution is 5.0 to 7.0.
Preferably, the concentration of the second phase solution is between 1.0 and 20 percent by mass.
Preferably, the PH of the second buffered solution is 7.5 to 10.0.
Preferably, the iodine-containing polyethylene glycol (PEG-TIBSG) has a molecular weight between 5K and 20K.
Preferably, the aminopolyethylene glycol (PEG-NH2) has a molecular weight of between 5K and 20K.
The preparation method of the developable hydrogel comprises the steps of respectively conveying the first phase solution and the second phase solution to a position to be polymerized through the double-cavity micro catheter, and polymerizing the first phase solution and the second phase solution into the hydrogel after mixing at the position.
Preferably, the polymerization time is between 3 and 20 s.
The developable hydrogel according to the present invention is useful for barrier protection in, for example, radiation therapy for prostate cancer. During radiation therapy, radiation passes through cancerous tissue and there is inevitable radiation damage to adjacent normal tissue, such as the rectum. And a hydrogel pad is formed between the prostate and the rectum, so that redundant rays can be effectively blocked, and normal tissues are prevented from being damaged by radiation. It is to be understood that the developable hydrogel according to the present invention can also be used for barrier protection in radiotherapy such as cervical cancer, and the site to be polymerized is set as a site requiring radiation barrier.
According to the developable hydrogel, two different liquids are adopted before polymerization, namely the first phase solution and the second phase solution, the two liquids are mixed and then cross-linked and polymerized to form the hydrogel during use, the polymerized hydrogel has high elasticity and can be closely attached to tissues, the polymerized hydrogel can be developed under X rays, and when the developable hydrogel is used under the X rays, doctors can observe the conditions of the implantation rate, the implantation position and the like of the hydrogel in real time, so that the risk of ectopic implantation is greatly reduced.
Detailed Description
The following provides a detailed description of the preferred embodiments of the present invention.
Example 1
Preparing a first phase solution
First, a first buffer solution having a PH of 5.0 to 7.0 was prepared using sodium dihydrogen phosphate, 10% phosphoric acid, and purified water. Then, iodine-containing polyethylene glycol (PEG-TIBSG) is weighed according to the following amount in the table 1, and dissolved by using a first buffer solution to prepare a first phase solution with the mass percentage concentration of 1.0-20%.
In examples 1-13, the iodine-containing polyethylene glycol (PEG-TIBSG) is a four-arm iodine-containing polyethylene glycol (4-arm-PEG-TIBSG) having 1-2 arms grafted with an iodine-containing group (2, 3, 5-triiodo-benzamide or 2, 4, 6-triiodo-benzamide), such as 4-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate, or 4-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, of the formula:
wherein R is 1 Is pentaerythritol, n is 1-250, m1 is 2-3, and m2 is 1-2.
In examples 14-25, the iodine-containing polyethylene glycol (PEG-TIBSG) is an eight-arm iodine-containing polyethylene glycol (8-arm-PEG-TIBSG) having 1-4 arms grafted with an iodine-containing group (2, 3, 5-triiodo-benzamide or 2, 4, 6-triiodo-benzamide), such as 8-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate, or 8-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, of the formula:
wherein R is 2 Is tripentaerythritol, n is 1-250, m3 is 4-5, and m4 is 3-4.
Preparing a second phase solution
First, a second buffer solution at PH 7.5-10.0 was prepared with sodium tetraborate with 10% phosphoric acid or 20% sodium hydroxide. Then, the amino compound is weighed according to the following amount in table 1, and dissolved by a second buffer solution to prepare a second phase solution with the mass percentage concentration of 1.0-20%.
In examples 1 to 4 and 14 to 17, the amino compound was trilysine.
In examples 5 to 8 and 18 to 21, the amino compound was polyethyleneimine.
In examples 9-13 and 22-25, the amino compound is an aminopolyethylene glycol (PEG-NH2), such as a four-arm aminopolyethylene glycol (4-arm-PEG-NH 2) or an eight-arm aminopolyethylene glycol (8-arm-PEG-NH 2).
Preparation of hydrogels
2.0ml of the first phase solution is pumped into a first syringe with the volume of 3ml, 2.0ml of the second phase solution is pumped into a second syringe with the volume of 3ml, the first syringe and the second syringe are respectively connected with the double-cavity micro-catheter, simultaneously, a syringe push rod is pushed, and the solution flows out from the far end of the double-cavity micro-catheter and then is polymerized into hydrogel. The hydrogels were separately observed under X-ray and developed, and the results are shown in table 1 below:
TABLE 1
Comparative example 1
Preparing a first phase solution
First, a first buffer solution having a PH of 5.0 to 7.0 was prepared using sodium dihydrogen phosphate, 10% phosphoric acid, and purified water. Then, polyethylene glycol succinimidyl glutarate (PEG-SG) is weighed according to the following amount in the following table 2, and is dissolved by a first buffer solution to prepare a first phase solution with the mass percentage concentration of 1.0-20%.
In examples 26 to 30, the polyethylene glycol succinimidyl glutarate (PEG-SG) was a four-arm polyethylene glycol (4-arm PEG-SG).
In examples 31-36, the polyethylene glycol succinimidyl glutarate (PEG-SG) was an eight-arm polyethylene glycol (8-arm PEG-SG).
Preparing a second phase solution
First, a second buffer solution at PH 7.5-10.0 was prepared with sodium tetraborate with 10% phosphoric acid or 20% sodium hydroxide. Then, the amino compound is weighed according to the following amount in table 2, and dissolved by using a second buffer solution to prepare a second phase solution with the mass percentage concentration of 1.0-20%.
In examples 26 and 31, the amino compound was trilysine.
In examples 27 and 32, the amino compound was polyethyleneimine.
In examples 28-30 and 33, the amino compound is an aminopolyethylene glycol (PEG-NH2), such as a four-arm aminopolyethylene glycol (4-arm-PEG-NH 2) or an eight-arm aminopolyethylene glycol (8-arm-PEG-NH 2).
Preparation of hydrogels
2.0ml of the first phase solution is pumped into a first syringe with the volume of 3ml, 2.0ml of the second phase solution is pumped into a second syringe with the volume of 3ml, the first syringe and the second syringe are respectively connected with the double-cavity micro-catheter, simultaneously, a syringe push rod is pushed, and the solution flows out from the far end of the double-cavity micro-catheter and then is polymerized into hydrogel. The hydrogels were separately observed under X-ray and developed, and the results are shown in table 2 below:
TABLE 2
Comparative example 2
Preparing a first phase solution
First, a first buffer solution having a PH of 5.0 to 7.0 was prepared using sodium dihydrogen phosphate, 10% phosphoric acid, and purified water. Then, iodine-containing polyethylene glycol (PEG-I-SG) is weighed according to the following amount in Table 3, dissolved by a first buffer solution, and prepared into a first phase solution with the mass percentage concentration of 1.0-20%.
In example 37-41, the iodine-containing polyethylene glycol (PEG-I-SG) was a four-arm iodine-containing polyethylene glycol (4-arm-PEG-I-SG), and the four-arm iodine-containing polyethylene glycol (4-arm-PEG-I-SG) was a 4-arm-polyethylene glycol-iodo-succinimide glutarate of the following formula:
wherein R is 1 Is pentaerythritol, n-1-250, m 1-2-3, m 2-1-2.
In example 42-example 47, the iodine-containing polyethylene glycol (PEG-I-SG) was an eight-arm iodine-containing polyethylene glycol (8-arm-PEG-I-SG), which was 8-arm-polyethylene glycol-iodo-succinimide glutarate of the following formula:
wherein R is 2 Is tripentaerythritol, n is 1-250, m3 is 4-5, and m4 is 3-4.
Preparing a second phase solution
First, a second buffer solution at PH 7.5-10.0 was prepared with sodium tetraborate with 10% phosphoric acid or 20% sodium hydroxide. Then, the amino compound is weighed according to the following amount in table 3, and dissolved by using a second buffer solution to prepare a second phase solution with the mass percentage concentration of 1.0-20%.
In examples 37 and 42, the amino compound was trilysine.
In examples 38 and 43, the amino compound was polyethyleneimine.
In examples 39-41 and 44-47, the amino compound is an aminopolyethylene glycol (PEG-NH2), such as a four-arm aminopolyethylene glycol (4-arm-PEG-NH 2) or an eight-arm aminopolyethylene glycol (8-arm-PEG-NH 2).
Preparation of hydrogels
2.0ml of the first phase solution is pumped into a first syringe with the volume of 3ml, 2.0ml of the second phase solution is pumped into a second syringe with the volume of 3ml, the first syringe and the second syringe are respectively connected with the double-cavity micro-catheter, simultaneously, a syringe push rod is pushed, and the solution flows out from the far end of the double-cavity micro-catheter and then is polymerized into hydrogel. The hydrogels were separately observed under X-ray and developed, and the results are shown in the following table 3:
TABLE 3
The above embodiments are merely preferred embodiments of the present invention, which are not intended to limit the scope of the present invention, and various changes may be made in the above embodiments of the present invention. All simple and equivalent changes and modifications made according to the claims and the content of the specification of the present application fall within the scope of the claims of the present patent application. The invention has not been described in detail in order to avoid obscuring the invention.
Claims (10)
1. A developable hydrogel is characterized in that the developable hydrogel is formed by polymerizing a first phase solution and a second phase solution, the first phase solution is formed by dissolving iodine-containing polyethylene glycol in a first buffer solution, the iodine-containing polyethylene glycol is four-arm iodine-containing polyethylene glycol or eight-arm iodine-containing polyethylene glycol, the four-arm iodine-containing polyethylene glycol is 4-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 4-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, the eight-arm iodine-containing polyethylene glycol is 8-arm-polyethylene glycol-2, 3, 5-triiodo-benzamide-succinimide glutarate or 8-arm-polyethylene glycol-2, 4, 6-triiodo-benzamide-succinimide glutarate, the second phase solution is formed by dissolving an amino compound in a second buffer solution, wherein the amino compound is trilysine, polyethyleneimine or aminopolyethylene glycol, and the aminopolyethylene glycol is four-arm aminopolyethylene glycol or eight-arm aminopolyethylene glycol.
2. The developable hydrogel according to claim 1, wherein the ratio of the molar amount of the iodine-containing group in the iodine-containing polyethylene glycol to the molar amount of the amino group in the amino compound is between 1: 1-3.
3. The developable hydrogel according to claim 1, wherein 1 to 2 arms of the four-arm iodine-containing polyethylene glycol are grafted with an iodine-containing group, and 1 to 4 arms of the eight-arm iodine-containing polyethylene glycol are grafted with an iodine-containing group.
4. The developable hydrogel according to claim 1, wherein the concentration of the first phase solution is between 1.0% and 20% by mass.
5. The developable hydrogel according to claim 1, wherein the PH of the first buffer solution is 5.0 to 7.0.
6. The developable hydrogel according to claim 1, wherein the second phase solution has a concentration of between 1.0% and 20% by weight.
7. The developable hydrogel according to claim 1, wherein the PH of the second buffer solution is 7.5 to 10.0.
8. The developable hydrogel according to claim 1, wherein the iodine-containing polyethylene glycol has a molecular weight between 5K and 20K.
9. The developable hydrogel according to claim 1, wherein the aminopolyethylene glycol has a molecular weight between 5K and 20K.
10. A method of preparing a developable hydrogel according to any one of claims 1 to 9, comprising separately delivering the first phase solution and the second phase solution to a site to be polymerized through a double lumen microcatheter, the first phase solution and the second phase solution polymerizing into the hydrogel after mixing at the site.
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| CN202210488421.8A CN114891242A (en) | 2022-05-06 | 2022-05-06 | Developable hydrogel and preparation method thereof |
| PCT/CN2022/095860 WO2023212990A1 (en) | 2022-05-06 | 2022-05-30 | Imageable hydrogel and method for preparing same |
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| CN116421744A (en) * | 2023-04-17 | 2023-07-14 | 杭州融华再生医学科技有限公司 | Absorbable medical hydrogel and preparation method thereof |
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| US20100297235A1 (en) * | 2009-05-20 | 2010-11-25 | Cpc Of America, Inc. | Vascular puncture closure systems, devices, and methods using biocompatible synthetic hydrogel compositions |
| US10111985B2 (en) * | 2011-08-10 | 2018-10-30 | Medicus Biosciences, Llc | Biocompatible hydrogel polymer formulations for the controlled delivery of biomolecules |
| CN105963792B (en) * | 2016-04-29 | 2019-03-22 | 深圳迈普再生医学科技有限公司 | Medical aquogel composition, medical aquogel and the preparation method and application thereof |
| CN110193091A (en) * | 2018-02-27 | 2019-09-03 | 华东理工大学 | Injectable albumen/polyethylene glycol groups hydrogel material and its preparation method and application |
| CN111420126B (en) * | 2020-03-24 | 2021-07-27 | 江苏地韵医疗科技有限公司 | Medical hydrogel, complete set of raw materials and application thereof |
| CN114344554A (en) * | 2022-02-11 | 2022-04-15 | 上海益思妙医疗器械有限公司 | Application of PEG compound in preparation of embolic agent |
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| CN116421744A (en) * | 2023-04-17 | 2023-07-14 | 杭州融华再生医学科技有限公司 | Absorbable medical hydrogel and preparation method thereof |
| CN116421744B (en) * | 2023-04-17 | 2024-02-09 | 杭州融华再生医学科技有限公司 | Absorbable medical hydrogel and preparation method thereof |
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