CN119236151A - A tissue adhesive patch and a preparation method thereof - Google Patents
A tissue adhesive patch and a preparation method thereof Download PDFInfo
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- CN119236151A CN119236151A CN202411764148.2A CN202411764148A CN119236151A CN 119236151 A CN119236151 A CN 119236151A CN 202411764148 A CN202411764148 A CN 202411764148A CN 119236151 A CN119236151 A CN 119236151A
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Abstract
The invention discloses a tissue adhesive patch and a preparation method thereof, relates to the technical field of medical materials, and solves the technical problems of insufficient adhesive force and poor mechanical property of the existing tissue adhesive; the adhesive patch comprises an adhesive layer and a reinforcing layer, wherein the adhesive layer is coated on the surface of the reinforcing layer and is photo-cured to form the tissue adhesive patch, the raw material of the reinforcing layer is a degradable polyester material, the raw material of the adhesive layer comprises a component A, a component B, a component C and a component D, the component A is a degradable high polymer material, the component B is acrylic esters or N-isopropyl acrylamide, the component C is catechol-containing substances, and the component D is a quaternary ammonium salt cationic monomer containing unsaturated double bonds.
Description
Technical Field
The invention relates to the technical field of medical materials, in particular to a tissue adhesive patch and a preparation method thereof.
Background
Methods commonly used clinically for repair of wounds or fistulae on visceral tissue surfaces include gluing with tissue glue or anastomosis of fistulae with a stapler. Commonly used tissue adhesives include alpha-cyanoacrylate, fibrin glue and the like, and the alpha-cyanoacrylate has strong adhesive force, but has large hardness after adhesion, poor toughness, poor matching with tissue mechanics, poor biocompatibility and easy generation of toxic and side effects. The fibrin glue adhesive is an adhesive extracted from human plasma and mainly comprises fibrinogen, thrombin and the like, the curing reaction of the fibrin glue adhesive directly utilizes the coagulation mechanism of the human body, and finally a fibrin network with strong adhesive force is generated, but the adhesive has the risks of poor wet surface adhesive force, immunogenicity and virus infection.
In the prior art, hydrogel is partially used as an adhesive to carry out adhesion repair on tissues, the biocompatibility is good, the form is various and the adhesive can be suitable for complex tissues, but the problems that the hydrogel adhesive has insufficient wet surface adhesive force and the mechanical property can not meet the use requirement are found in practice.
Disclosure of Invention
The invention aims to solve the technical problems of insufficient wet surface adhesion and poor mechanical property of the existing tissue adhesive, and provides a tissue adhesive patch and a preparation method thereof.
The invention is realized by the following technical scheme.
A first object of the present invention is to provide a tissue adhesive patch comprising an adhesive layer and a reinforcing layer;
the adhesive layer is coated on the surface of the reinforcing layer and is photo-cured to form a tissue adhesive patch;
the raw material of the reinforcing layer is degradable polyester material;
The raw materials of the adhesive layer comprise a component A, a component B, a component C and a component D;
The component A is a degradable high polymer material;
The component B is acrylic esters or N-isopropyl acrylamide;
The component C is a catechol-containing substance;
The component D is a quaternary ammonium salt cationic monomer containing unsaturated double bonds.
Further, the component A is selected from any one or more of polyvinylpyrrolidone, polyvinyl alcohol, carboxymethyl cellulose, hydroxypropyl methyl cellulose, sodium alginate, gelatin, acacia and tragacanth.
Preferably, the component A is selected from any one or more of polyvinyl alcohol and polyvinylpyrrolidone.
Further, the acrylic ester is selected from any one or a combination of a plurality of hydroxyethyl methacrylate, hydroxyethyl acrylate and hydroxybutyl acrylate.
Preferably, the acrylic acid esters are selected from hydroxyethyl acrylate.
Further, the component C is selected from any one or more of dopamine hydrochloride, dopamine derivatives, tannic acid, gallic acid and catechin.
Preferably, the component C is selected from any one or a combination of more than one of dopamine hydrochloride and tannic acid.
Further, the raw material of the reinforcing layer is selected from any one or more of PLGA, PLA, PGA, PCL, PPDO, PHA, PHB and PHV.
Further, the component D is selected from any one or more of acryloyloxyethyl trimethyl ammonium chloride, methacryloyloxyethyl trimethyl ammonium chloride, methacrylamidopropyl trimethyl ammonium chloride and alkylallyl ammonium chloride.
Further, the adhesive layer also comprises an active ingredient capable of loading and promoting tissue healing, wherein the active ingredient comprises recombinant human epidermal growth factor, fibroblast growth factor and vascular endothelial growth factor.
A second object of the present invention is to provide a method for preparing a tissue adhesive patch, comprising the steps of:
The degradable polyester solution is coated on a template to form a layer of degradable polyester liquid film, the coated template is put into a vacuum drying oven for drying, and a reinforcing layer is formed after the drying is completed;
Dissolving degradable polymer material of raw material component A of adhesive layer, acrylic ester of component B or N-isopropyl acrylamide, catechol-containing substance of component C and quaternary ammonium salt cationic monomer of component D containing unsaturated double bond in distilled water, regulating pH to 8.0-9.0, adding water-soluble photoinitiator, stirring and dissolving to form prepolymer solution, coating the prepolymer solution on the reinforcing layer, curing in ultraviolet curing box for 0.5-3 hr, and forming the tissue adhesive patch.
Further, the dissolution concentration of the degradable polyester material is 3% -20%, the dissolution concentration of the component A is 5% -20%, the dissolution concentration of the component B is 10% -35%, the dissolution concentration of the component C is 5% -20%, and the dissolution concentration of the component D is 1% -15%.
Further, the organic solvent is selected from any one of hexafluoroisopropanol, ethyl formate, ethyl acetate, toluene and methylene dichloride.
Further, the addition amount of the water-soluble photoinitiator is 0.05-0.1% of the total mass of the solution.
Further, the water-soluble photoinitiator is selected from alpha-hydroxy ketone aqueous photoinitiators.
Compared with the prior art, the invention has the following advantages and beneficial effects.
1. According to the invention, catechol-containing substances are subjected to self-polymerization under certain conditions, and are copolymerized with acrylic esters or N-isopropyl acrylamide and quaternary ammonium salt cationic monomers to form an adhesive main body, and an interpenetrating network structure is formed with a degradable high polymer material, so that the cohesive force of the adhesive main body is enhanced. The polymerized adhesive body contains a large number of catechol groups which can form hydrogen bonds and pi-pi bonds with hydroxyl groups and amine groups on the surface of a tissue to provide strong wet adhesion, and the introduction of quaternary ammonium salt cationic monomers can form strong electrostatic force interaction with functional groups such as OH-, COOO-and the like which have negative charges on the surface of the tissue to provide non-covalent bonding adhesion, so that the wet adhesion of the adhesive is further improved. Meanwhile, polar groups in the degradable high polymer material can also form strong hydrogen bonds and van der Waals force effects with the tissue surface to provide partial adhesive force, and the tissue adhesive patch provided by the invention has stronger adhesive force through the mutual synergistic effect of multiple groups.
2. The quaternary ammonium salt introduced into the tissue adhesive patch has good broad-spectrum bactericidal property, so that the tissue adhesive patch has a certain antibacterial property while having strong adhesive force, and can effectively prevent wound infection.
3. According to the adhesive, the adhesive prepolymer solution is polymerized and cured on the reinforcing layer under the action of ultraviolet light, and radical polymerization reaction can promote the radical part in the adhesive to be grafted on the reinforcing layer, so that the adhesive layer and the reinforcing layer are firmly combined together, the adhesive layer is subjected to the action of enhancing the mechanical strength and toughness through the arrangement of the reinforcing layer, and the mechanical property of the patch is improved.
Drawings
In order to more clearly illustrate the technical solutions of the exemplary embodiments of the present invention, the drawings that are needed in the examples will be briefly described below, it being understood that the following drawings only illustrate some examples of the present invention and therefore should not be considered as limiting the scope, and that other related drawings may be obtained from these drawings without inventive effort for a person skilled in the art. In the drawings:
FIG. 1 is a schematic structural view of a tissue adhesive patch of the present invention;
FIG. 2 is a product view of a tissue adhesive patch made in accordance with example 5 of the present invention;
FIG. 3 is a graph of lap-shear bond strength of a tissue adhesive patch prepared in example 5 of the present invention;
FIG. 4 is a graph of peel strength of a tissue adhesive patch prepared in example 5 of the present invention.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the present invention more apparent, the technical solutions in the examples of the present invention will be clearly and completely described below with reference to the examples and the accompanying drawings, and it is apparent that the exemplary embodiments of the present invention and the descriptions thereof are only for explaining the present invention and are not limiting the present invention.
Embodiments of a tissue adhesive patch and a method of manufacturing the same according to the present invention are described in detail below with appropriate reference to the accompanying drawings. However, unnecessary detailed description may be omitted. For example, detailed descriptions of well-known matters may be omitted. This is to avoid that the following description becomes unnecessarily lengthy, facilitating the understanding of those skilled in the art.
The "range" disclosed herein is defined in terms of lower and upper limits, with the given range being defined by the selection of a lower and an upper limit, the selected lower and upper limits defining the boundaries of the particular range. Ranges that are defined in this way can be inclusive or exclusive of the endpoints, and any combination can be made, i.e., any lower limit can be combined with any upper limit to form a range.
All embodiments of the application and alternative embodiments may be combined with each other to form new solutions, unless otherwise specified.
All technical features and optional technical features of the application may be combined with each other to form new technical solutions, unless specified otherwise.
The terms "comprising" and "including" as used herein mean open ended or closed ended, unless otherwise noted. For example, the terms "comprising" and "including" may mean that other materials not listed may be included or included, or that only listed materials may be included or included.
All the steps of the present application may be performed sequentially or randomly, preferably sequentially, unless otherwise specified.
In order to solve the technical problems of insufficient adhesive force and poor mechanical property of the existing tissue adhesive, the technical scheme of the invention is to provide a tissue adhesive patch, the structure of which is shown in figure 1 and comprises an adhesive layer and a reinforcing layer;
the adhesive layer is coated on the surface of the reinforcing layer and is photo-cured to form a tissue adhesive patch;
the raw material of the reinforcing layer is degradable polyester material;
The raw materials of the adhesive layer comprise a component A, a component B, a component C and a component D;
The component A is a degradable high polymer material;
The component B is acrylic esters or N-isopropyl acrylamide;
The component C is a catechol-containing substance;
The component D is a quaternary ammonium salt cationic monomer containing unsaturated double bonds.
According to the invention, catechol-containing substances are subjected to self-polymerization under a certain condition, and are copolymerized with acrylic esters or N-isopropyl acrylamide to form an adhesive main body, and an interpenetrating network structure is formed with a degradable high polymer material, so that the cohesive force of the adhesive main body is enhanced. The polymerized adhesive body contains a large amount of catechol groups, so that strong wet adhesion can be provided, and meanwhile, polar groups in degradable high polymer materials such as PVP can form strong hydrogen bonds and van der Waals force effects with the tissue surface to provide partial adhesion.
The adhesive prepolymer solution is polymerized and cured on the reinforcing layer under the action of ultraviolet light, radical polymerization reaction can promote radical partial grafting in the adhesive to the reinforcing layer, so that the adhesive layer and the reinforcing layer are firmly combined together, specifically, the acrylate or quaternary ammonium salt cationic monomer in the adhesive component reacts and connects the radical generated by the carbon-carbon double bond and the hydroxyl in the polyester of the reinforcing layer together under the action of the ultraviolet light initiator, and the adhesive layer and the reinforcing layer are firmly combined together. Therefore, the adhesive layer is subjected to the effect of enhancing the mechanical strength and toughness through the arrangement of the reinforcing layer, and the mechanical property of the patch is improved. In actual use, the mechanical strength of the patch can be adjusted by adjusting the concentration of the reinforcing layer so as to meet the requirements of different tissues on the mechanical strength, and the adhesive layer and the tissues can be attached better.
The tissue adhesive patch provided by the invention can be adhered on the surface of wet tissues or on the surface of dry tissues after the patch is wetted by water, and has strong adhesive force. After the surface of the adhesive patch is contacted with moisture, the moisture is quickly absorbed by the water-absorbing component in the adhesive patch so that the dry adhesive layer forms adhesive gel, and meanwhile, the moisture on the surface of the tissue is removed, thereby facilitating the reaction of the adhesive groups in the adhesive and the groups on the surface of the tissue to form strong adhesion.
The tissue adhesive patch is applied to repair various tissue wounds or fistulae, such as skin surface wounds, and used as adhesive patches for various visceral tissue wounds, such as heart, liver, kidney, gastrointestinal tract, vascular and other tubular tissue cracks, and can be matched with repair tools such as intestinal anastomat to strengthen anastomoses. The patch has good mechanical flexibility, and can adapt to normal physiological peristalsis of tissues without being torn.
In one or more embodiments, the component a is selected from any one or more of polyvinylpyrrolidone, polyvinyl alcohol, carboxymethyl cellulose, hydroxypropyl methylcellulose, sodium alginate, gelatin, acacia, and tragacanth. Preferably, the component A is selected from any one or more of polyvinyl alcohol and polyvinylpyrrolidone.
In one or more embodiments, the acrylic acid esters are selected from any one or more combinations of hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxybutyl acrylate. Preferably, the acrylic acid esters are selected from hydroxyethyl acrylate.
In one or more embodiments, the component C is selected from any one or more combinations of dopamine hydrochloride, dopamine derivatives, tannic acid, gallic acid and catechin. Preferably, the component C is selected from any one or a combination of more than one of dopamine hydrochloride and tannic acid.
In one or more embodiments, the raw material of the reinforcing layer is selected from any one or more combinations of PLGA, PLA, PGA, PCL, PPDO, PHA, PHB and PHV.
In one or more embodiments, the component D is selected from any one or more of acryloyloxyethyl trimethyl ammonium chloride, methacryloyloxyethyl trimethyl ammonium chloride, methacrylamidopropyl trimethyl ammonium chloride, and alkylallyl ammonium chloride in combination.
In order to extend the functionality of the tissue adhesive patch of the present invention, active ingredients that promote tissue healing may also be loaded during the preparation of the adhesive layer, including, but not limited to, recombinant human epidermal growth factor, fibroblast growth factor, vascular endothelial growth factor, and the like.
Based on the above tissue adhesive patch, the invention also provides a preparation method of the tissue adhesive patch, comprising the following steps:
The preparation method comprises the steps of dissolving a degradable polyester material in an organic solvent to form a clear transparent solution, coating the degradable polyester solution on a polytetrafluoroethylene template by using a rotary film coater to form a layer of degradable polyester liquid film, wherein the spin coating parameters are that the rotating speed is 80-400r/min, the acceleration is 20-100m/s, the spin coating time is 10-40s, then drying the coated template in a vacuum drying oven, the drying parameters are that the time is 10-40min, the pressure is-0.5-0.01 Mpa, and the temperature is 30-80 ℃, and forming a reinforcing layer after the drying is completed;
Dissolving degradable polymer material of raw material component A of adhesive layer, acrylic ester or N-isopropyl acrylamide of component B and catechol-containing substance of component C, and quaternary ammonium salt cationic monomer of component D containing unsaturated double bond in distilled water to form clear and transparent solution, dripping organic amine solution such as sodium hydroxide solution or triethylamine to adjust pH to 8.0-9.0, adding water-soluble photoinitiator, stirring to dissolve to form prepolymer solution, coating the prepolymer solution on the reinforcing layer by using a spin coater, spin coating with parameters of rotation speed 80-400r/min, acceleration 20-100m/s, spin coating time 10-40s, curing in ultraviolet curing box (60 w,365 nm) for 0.5-3h, and removing the formed membrane from the template after curing to obtain the tissue adhesive patch.
In one or more embodiments, the degradable polyester material has a concentration in the organic solvent of 3% to 20%, preferably 5% to 10%, the component a has a dissolved concentration of 5% to 20%, the component B has a dissolved concentration of 10% to 35%, the component C has a dissolved concentration of 5% to 20%, and the component D has a dissolved concentration of 1% to 15%.
In one or more embodiments, the organic solvent is selected from any one of hexafluoroisopropanol, ethyl formate, ethyl acetate, toluene, and dichloromethane.
In one or more embodiments, the water-soluble photoinitiator is added in an amount of 0.05 to 0.1% by weight of the total solution. In particular, the water-soluble photoinitiator is selected from alpha-hydroxy ketone aqueous photoinitiators, such as Irgacure2959, irgacure651, etc., preferably Irgacure2959.
The technical scheme of the present invention is described in further detail below with reference to examples.
The experimental methods used in the examples were conventional methods unless otherwise specified. The materials, reagents, methods and apparatus used, without any particular description, are those conventional in the art and are commercially available to those skilled in the art.
Example 1
Preparation of the reinforcing layer:
PLGA was dissolved in hexafluoroisopropanol to form a clear solution at a concentration of 10%. And (3) coating the PLGA solution on a polytetrafluoroethylene die by using a spin coater to form a layer of PLGA liquid film, wherein the spin speed is 100r/min, and the spin time is 15s. And (5) placing the spin-coated die into a vacuum drying oven, drying for 30min, and removing hexafluoroisopropanol solvent to obtain the patch reinforcing layer with the thickness of 250um.
Example 2
Preparation of the reinforcing layer:
PLGA was dissolved in hexafluoroisopropanol to form a clear solution at a concentration of 15%. And (3) coating the PLGA solution on a polytetrafluoroethylene die by using a spin coater to form a layer of PLGA liquid film, wherein the spin speed is 100r/min, and the spin time is 15s. And (5) placing the spin-coated die into a vacuum drying oven, drying for 30min, and removing hexafluoroisopropanol solvent to obtain the patch reinforcing layer with the thickness of 200um.
Example 3
Preparation of the reinforcing layer:
PLGA was dissolved in hexafluoroisopropanol to a clear solution at a concentration of 5%. And (3) coating the PLGA solution on a polytetrafluoroethylene die by using a spin coater to form a layer of PLGA liquid film, wherein the spin speed is 100r/min, and the spin time is 15s. And (5) placing the spin-coated die into a vacuum drying oven, drying for 40min, and removing hexafluoroisopropanol solvent to obtain the patch reinforcing layer with the thickness of 150um.
Example 4
Preparation of the reinforcing layer:
PCL was dissolved in toluene to form a clear solution at a concentration of 15%. And (3) coating the PLGA solution on a polytetrafluoroethylene die by using a spin coater to form a layer of PLGA liquid film, wherein the spin speed is 100r/min, and the spin time is 15s. And (5) placing the spin-coated die into a vacuum drying oven, drying for 35min, and removing hexafluoroisopropanol solvent to obtain the patch reinforcing layer with the thickness of 200um.
Example 5
Preparation of tissue adhesive patches the product prepared in example 1 was used as a patch reinforcement layer:
The raw materials of each component are dissolved in distilled water to form homogeneous prepolymer solution, the concentrations of the prepolymer solution are respectively 8 percent of polyvinylpyrrolidone, 12 percent of hydroxyethyl acrylate, 8 percent of dopamine hydrochloride, 5 percent of methacryloxyethyl trimethyl ammonium chloride and 0.5 percent of Irgacure2959 initiator, and the pH value of the prepolymer solution is adjusted to 8.5 by 2mol/L of NaOH solution. The prepolymer solution was spin coated onto the PLGA reinforcement layer mold. The reinforcing layer was subjected to light curing under an ultraviolet lamp of 365nm for 1 hour to obtain a tissue adhesive patch with a thickness of 580um, and the product prepared in this example is shown in fig. 2.
Example 6
Preparation of tissue adhesive patches the product prepared in example 1 was used as a patch reinforcement layer:
the raw materials of each component are dissolved in distilled water to form homogeneous prepolymer solution, the concentration of each prepolymer solution is 10 percent of polyvinyl alcohol, 10 percent of N-isopropyl acrylamide, 10 percent of dopamine hydrochloride, 5 percent of methacryloyloxyethyl trimethyl ammonium chloride and 0.5 percent of Irgacure2959 initiator, and the pH value of each prepolymer solution is adjusted to 8.5 by 2mol/L of NaOH solution. The prepolymer solution was spin coated onto the PLGA reinforcement layer mold. And (3) placing the enhancement layer under an ultraviolet lamp at 365nm to be photo-cured for 1h, thus obtaining the tissue adhesive patch with the thickness of 600um.
Example 7
Preparation of tissue adhesive patches the product prepared in example 1 was used as a patch reinforcement layer:
The raw materials of each component are dissolved in distilled water to form homogeneous prepolymer solution, the concentration of each prepolymer solution is 3 percent sodium alginate, 10 percent hydroxyethyl acrylate, 10 percent tannic acid, 8 percent dimethyl diallyl ammonium chloride and 0.8 percent Irgacure651 initiator, and the pH value of each prepolymer solution is adjusted to 8.5 by 2mol/L NaOH solution. The prepolymer solution was spin coated onto the PLGA reinforcement layer mold. And (3) placing the enhancement layer under an ultraviolet lamp at 365nm to be photo-cured for 1h, thus obtaining the tissue adhesive patch with the thickness of 500um.
Comparative example 1
A tissue adhesive patch was prepared by the method of example 5, except that the adhesive layer had no component D in its composition.
Comparative example 2
The tissue adhesive patch was prepared by the method of example 5, except that the reinforcing layer was not included.
The performance of the tissue adhesive patches prepared in examples 5-7 of the present invention and comparative examples was tested and the test results are shown in table 1.
(1) Burst pressure test
Taking clean fresh pig small intestine, wherein the length is about 15cm, clamping one end of the small intestine by using surgical forceps, inserting a silica gel hose connected with CO 2 gas at the other end of the small intestine, and closing and fixing by using a binding belt, wherein a high-precision pressure test meter is arranged on the silica gel hose and used for testing bursting pressure. A break of about 2mmx2mm was made in the middle of the small intestine and the adhesive patch was cut into a square of 10mmx10 mm. The cut patch is adhered to the opening of the small intestine after being wetted by normal saline, a CO 2 air source is opened after the patch is pressed for 10min, ventilation is carried out in the small intestine at the speed of 2mL/s, and the maximum pressure in the whole process is recorded to be the bursting pressure of the tissue patch.
(2) Lap-shear tensile strength test
After degreasing fresh pigskin according to annex 2, the pigskin is cut into strips with length x width x thickness=60 mmx25mmx2mm and the tissue patches are cut into strips with the same length and width. The pig skin was lapped with the adhesive layer side front end of the tissue patch by 25mmx10mm, and after lapping was pressed for 30min, tested according to the method of astm f2255, data were collected, and the shear strength of the interface was calculated, wherein the lap-shear adhesive strength curve of the tissue adhesive patch prepared in example 5 is shown in fig. 3.
(3) Peel strength test, interfacial toughness
After degreasing fresh pigskin, the pigskin is cut into strips with the length x width x thickness=60 mmx25mmx2mm and the tissue patch is cut into strips with the same length and width. The pigskin was bonded to the adhesive layer of the adhesive patch, pressed for 30 minutes after bonding, tested according to astm f2256 method, data collected, and peel strength calculated for the patch, wherein the peel strength curve for the tissue adhesive patch prepared in example 5 is shown in fig. 4.
(4) Elongation at break
Cutting the tissue adhesive patch into a size of 60mmx25mm, clamping and fixing the two ends of the patch on a universal testing machine by using a clamp, stretching the patch at a speed of 5mm/min, recording the elongation of the patch during fracture, and calculating the elongation at break of the tissue patch.
(5) Antibacterial property test
The leaching solution of the adhesive layer in the physiological saline is taken, the test method refers to WS/T650-2019, and the antibacterial performance test is carried out on staphylococcus aureus.
Table 1, examples 5-7 and comparative examples the performance of the tissue adhesive patches prepared by the test results
| Sample of | Burst pressure mmHg | Adhesive strength Kpa | Interfacial toughness J/m 2 | Elongation at break% | Tensile strength Mpa | Antibacterial rate% |
| Example 5 | 388 | 168.3 | 443.0 | 38 | 3.8 | 78.5 |
| Example 6 | 370 | 150.2 | 446.5 | 25 | 3.3 | 75.8 |
| Example 7 | 375 | 158.6 | 422.5 | 32 | 3.5 | 80.3 |
| Comparative example 1 | 242 | 110.0 | 330.0 | 37 | / | 8.8 |
| Comparative example 2 | 123 | 72.5 | 230.5 | 80 | 1.1 | / |
。
As can be seen from the data of table 1, the tissue adhesive patch prepared according to the present invention has excellent adhesive strength and peel strength, effectively improves mechanical properties of the patch compared to the adhesive patch without the reinforcing layer, and remarkably improves adhesiveness and antibacterial properties after the quaternary ammonium salt is introduced into the tissue adhesive patch.
It should be noted that, the foregoing specific embodiments are merely for the purpose of describing the present invention in detail, and that the foregoing description is merely illustrative of specific embodiments of the present invention and is not intended to limit the scope of the present invention, and that, although the present invention has been described in detail with reference to the foregoing specific embodiments, those skilled in the art will recognize that modifications, equivalents, improvements, etc. of some or all of the technical features of the present invention can be made thereto, and that such modifications, equivalents, improvements do not depart from the scope of the technical scope of the embodiments of the present invention, and are intended to be encompassed by the scope of the claims and the specification.
Claims (11)
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Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040195710A1 (en) * | 1990-10-15 | 2004-10-07 | Hubbell Jeffrey A. | Gels for encapsulation of biological materials |
| US20140148846A1 (en) * | 2012-11-29 | 2014-05-29 | The Brigham And Women's Hospital, Inc. | Adhesive Articles Containing a Combination of Surface Micropatterning and Reactive Chemistry and Methods of Making and Using Thereof |
| US20210113739A1 (en) * | 2018-04-20 | 2021-04-22 | President And Fellows Of Harvard College | Topological adhesion of materials |
| CN113952500A (en) * | 2021-09-28 | 2022-01-21 | 华南理工大学 | Tissue adhesive patch with single-sided adhesion and preparation method thereof |
| WO2022094592A1 (en) * | 2020-10-29 | 2022-05-05 | University Of Florida Research Foundation | Open cell hydrogel networks and methods for making and using the same |
| CN116059434A (en) * | 2022-12-30 | 2023-05-05 | 上海卓阮医疗科技有限公司 | A biomedical tissue adhesive and its preparation method |
| CN116139338A (en) * | 2022-12-30 | 2023-05-23 | 上海卓阮医疗科技有限公司 | Preparation method and application of self-fixing repair patch |
| CN116693931A (en) * | 2023-07-25 | 2023-09-05 | 中山大学 | A superstructure porous wet adhesive hydrogel and its preparation method and application |
| CN116920159A (en) * | 2023-07-18 | 2023-10-24 | 福建师范大学 | Synthesis and preparation method of a methacrylate catechol wet tissue-adhesive hydrogel that can be removed on demand |
| CN117752850A (en) * | 2021-09-23 | 2024-03-26 | 齐鲁工业大学(山东省科学院) | Photosensitive and temperature-sensitive mixed antibacterial hydrogel |
| US20240108782A1 (en) * | 2022-10-03 | 2024-04-04 | City University Of Hong Kong | An instant underwater bio-adhesive containing catechol moieties and water-resistant cholesterol |
| CN118203690A (en) * | 2024-01-04 | 2024-06-18 | 四川大学 | Medical glue for long-term bonding of wet tissue and preparation method thereof |
-
2024
- 2024-12-04 CN CN202411764148.2A patent/CN119236151B/en active Active
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040195710A1 (en) * | 1990-10-15 | 2004-10-07 | Hubbell Jeffrey A. | Gels for encapsulation of biological materials |
| US20140148846A1 (en) * | 2012-11-29 | 2014-05-29 | The Brigham And Women's Hospital, Inc. | Adhesive Articles Containing a Combination of Surface Micropatterning and Reactive Chemistry and Methods of Making and Using Thereof |
| US20210113739A1 (en) * | 2018-04-20 | 2021-04-22 | President And Fellows Of Harvard College | Topological adhesion of materials |
| WO2022094592A1 (en) * | 2020-10-29 | 2022-05-05 | University Of Florida Research Foundation | Open cell hydrogel networks and methods for making and using the same |
| CN117752850A (en) * | 2021-09-23 | 2024-03-26 | 齐鲁工业大学(山东省科学院) | Photosensitive and temperature-sensitive mixed antibacterial hydrogel |
| CN113952500A (en) * | 2021-09-28 | 2022-01-21 | 华南理工大学 | Tissue adhesive patch with single-sided adhesion and preparation method thereof |
| US20240108782A1 (en) * | 2022-10-03 | 2024-04-04 | City University Of Hong Kong | An instant underwater bio-adhesive containing catechol moieties and water-resistant cholesterol |
| CN116059434A (en) * | 2022-12-30 | 2023-05-05 | 上海卓阮医疗科技有限公司 | A biomedical tissue adhesive and its preparation method |
| CN116139338A (en) * | 2022-12-30 | 2023-05-23 | 上海卓阮医疗科技有限公司 | Preparation method and application of self-fixing repair patch |
| CN116920159A (en) * | 2023-07-18 | 2023-10-24 | 福建师范大学 | Synthesis and preparation method of a methacrylate catechol wet tissue-adhesive hydrogel that can be removed on demand |
| CN116693931A (en) * | 2023-07-25 | 2023-09-05 | 中山大学 | A superstructure porous wet adhesive hydrogel and its preparation method and application |
| CN118203690A (en) * | 2024-01-04 | 2024-06-18 | 四川大学 | Medical glue for long-term bonding of wet tissue and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| CAI YU: "Mussel-inspired quaternary composite hydrogels with high strength and high tissue adhesion for transdermal drug delivery:Synergistic hydrogen bonding and drug release mechanism", CHEMICAL ENGINEERING JOURNAL, vol. 465, 1 June 2023 (2023-06-01), pages 142942 * |
| LA GATTA ANNALISA: "Novel poly(HEMA-co-METAC)/alginate semi-interpenetrating hydrogels for biomedical applications:Synthesis and characterization", JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, vol. 90, no. 1, 1 July 2009 (2009-07-01), pages 292 - 302 * |
| ZHANG DONGFEI: "Fabrication of Strong hydrogen-bonding induced coacervate adhesive hydrogels with antibacterial and hemostatic actvities", BIOMATERIALS SCIENCE, vol. 8, no. 5, 7 March 2020 (2020-03-07), pages 1455 - 1463 * |
| 孟新月: "一种基于儿茶酚的双交联组织粘合剂的制备及其在内脏器官止血中的应用研究", 中国优秀硕士学位论文全文数据库, no. 05, 15 May 2024 (2024-05-15), pages 080 - 38 * |
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