CN115581817A - Biomedical coating material with antibacterial and lubricating functions and preparation method thereof - Google Patents
Biomedical coating material with antibacterial and lubricating functions and preparation method thereof Download PDFInfo
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- 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
- A61L31/16—Biologically active materials, e.g. therapeutic substances
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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
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular 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
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
- A61L2300/208—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
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- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
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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
- A61L2400/10—Materials for lubricating medical devices
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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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/04—Coatings containing a composite material such as inorganic/organic, i.e. material comprising different phases
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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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/06—Coatings containing a mixture of two or more compounds
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Abstract
The invention provides a biomedical coating material with antibacterial and lubricating functions and a preparation method thereof, belonging to the field of medical materials. The preparation method of the biomedical coating material comprises the steps of oxidizing, drying, coupling and drying a substrate material, soaking the substrate material in a sodium hyaluronate solution, physically crosslinking an organosilicon quaternary ammonium salt and polyvinyl alcohol into a positive charge film, and adsorbing the positive charge film with a negatively charged sodium hyaluronate layer to form the biomedical coating with antibacterial and lubricating functions.
Description
Technical Field
The invention belongs to the technical field of medical materials, and particularly relates to a biomedical coating material with an antibacterial lubricating function and a preparation method thereof.
Background
When the medical implant material enters a human body, the surface of the material and the tissue of the human body can cause pain and difficulty in entering, the pain of a patient is increased, and the friction can cause inflammation and increase the infection risk of the patient. The microorganisms are easy to proliferate and form a biomembrane on the surface of the implanted medical material, so that the limit of the microorganisms on the surface of the material exceeds the standard, the infection risk of a patient is increased, and the treatment difficulty is increased.
Disclosure of Invention
In order to solve the problems, the application provides an antibacterial lubricating coating which can reduce the surface energy of a medical implant material, improve the lubricating property of the medical implant material, reduce the toxicity of the medical implant material without coating, and improve the biocompatibility of the medical implant material.
Specifically, the application provides an antibacterial ultra-smooth coating material and a preparation method thereof, and in order to achieve the purpose, the technical scheme adopted by the invention for solving the technical problems is as follows:
a preparation method of a biomedical coating material with antibacterial and lubricating functions comprises the following steps:
(1) Carrying out oxidation reaction on the substrate material under the action of an oxidant, and drying after the reaction is finished to obtain an oxidized substrate material; under the condition that the pH value is 9-10, reacting the oxidized substrate material with a silane coupling agent, and washing and drying the substrate material and the silane coupling agent in sequence after the reaction is finished to obtain an intermediate product 1;
(2) Adding the intermediate product 1 into a sodium hyaluronate solution, adding a coupling agent, reacting at room temperature for 2-4h, and washing and drying after the reaction is finished to obtain an intermediate product 2;
(3) Dissolving polyvinyl alcohol and organosilicon quaternary ammonium salt in a DMSO aqueous solution, and heating to 80-120 ℃ to obtain a transparent organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution;
(4) Adding the intermediate product 2 in the step (2) into a transparent organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution, soaking for 2-4h at 80-120 ℃, taking out, placing in water at 80-100 ℃ for ultrasonic cleaning, placing in water at-30-10 ℃ for freezing for 20-24 h, taking out, recovering the room temperature, and repeating for three times to obtain the product.
The preparation method comprises the following steps: the oxidant used in the step (1) is 30% hydrogen peroxide, and the silane coupling agent is KH791.
The preparation method comprises the following steps: the mass ratio of the substrate material to the oxidant to the silane coupling agent is 5-15: 45-55: 5 to 30.
The preparation method comprises the following steps: the mass ratio of the substrate material to the oxidizing agent to the silane coupling agent is 8-12: 48 to 52:8 to 24.
The preparation method comprises the following steps: the substrate material in the step (1) is any one of silica gel, latex and titanium alloy.
The preparation method comprises the following steps: the coupling agent in the step (2) is EDCI.
The preparation method comprises the following steps: the mass ratio of the intermediate product 1, the sodium hyaluronate solution and the coupling agent in the step (2) is 1:0.3 to 0.7:0.01 to 1; further preferably: the mass ratio of the intermediate sodium hyaluronate solution to the coupling agent is 1:0.5:0.05; wherein the mass percent of the sodium hyaluronate solution is 0.5-1.5%.
The preparation method comprises the following steps: in the step (3), the mass ratio of the polyvinyl alcohol to the organosilicon quaternary ammonium salt to the DMSO aqueous solution is 1-3: 1 to 3:100, the DMSO content in the DMSO aqueous solution is 15-25 wt%.
The preparation method comprises the following steps: in the step (3), the organosilicon quaternary ammonium salt is 2-triethoxysilylpropylalkoxy-1, 3-didodecyldimethylammonium propane dichloride (CAS: 27668-53-7).
The preparation method comprises the following steps: the mass volume ratio of the intermediate product 2 to the organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution is (1-1.1) g: (4-10) mL.
A biomedical coating material with antibacterial and lubricating functions is prepared by the method.
Drawings
FIG. 1 is a scanning electron micrograph of the product obtained in example 1.
FIG. 2 is a scanning electron micrograph of the product obtained in example 2.
FIG. 3 is a scanning electron micrograph of the product obtained in example 3.
Detailed description of the preferred embodiments
The invention is further illustrated by the following examples, without limiting the scope of the invention:
example 1
10g of silica gel block is placed in 50ml of 30% hydrogen peroxide solution, the silica gel block is soaked for 48 hours at room temperature, taken out and placed in a forced air drying oven for drying at 50-55 ℃, silane coupling agent KH-791 24g is dissolved in 8ml of absolute ethyl alcohol, the silica gel block after oxidation modification is added, ammonia water is dripped to adjust the pH value to 9-10, the silica gel block is continuously soaked for 1-2 hours, taken out and ultrasonically cleaned for 20 minutes by using medicinal purified water, and the grafted silica gel is placed at 50-55 ℃ for drying, so that an intermediate product 1 can be obtained.
Putting 84g of the intermediate product 1 into 50ml of 1% sodium hyaluronate aqueous solution, adding 0.5g of EDCI, stirring at room temperature for 3h, taking out, and washing with deionized water to obtain sodium hyaluronate grafted silica gel, namely the intermediate product 2.
Placing 1.5g of polyvinyl alcohol into 100ml of 20% DMSO aqueous solution, heating to 100 ℃, stirring until the solution is clear, adding 1.5g of organic silicon quaternary ammonium salt (2-triethoxysilylpropylalkoxy-1, 3-didodecyldimethylammonium propane dichloride (CAS: 27668-53-7)), stirring completely, mixing, standing and defoaming to obtain an organic silicon quaternary ammonium salt polyvinyl alcohol crosslinking solution;
adding 100g of the intermediate product 2 into 1000ml of organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution, soaking for 2 hours, taking out, placing in 100 ℃ water, ultrasonically cleaning for 2 minutes, freezing for 24 hours at-20 ℃, taking out, recovering to room temperature, and repeating for three times to obtain the product.
Example 2
10g of latex block is placed in 50ml of 30 percent hydrogen peroxide solution, the latex block is soaked for 48 hours at room temperature, the latex block is taken out and is placed in a forced air drying oven for drying at the temperature of 50-55 ℃, silane coupling agent KH-791 g is dissolved in 8ml of absolute ethyl alcohol, the latex block modified by oxidation is added, ammonia water is dripped to adjust the pH value to 9-10, the latex block is continuously soaked for 1-2 hours, the latex block is taken out and is ultrasonically cleaned for 20 minutes by using medicinal purified water, and the grafted latex block is placed at the temperature of 50-55 ℃ for drying, so that an intermediate product 1 can be obtained.
Putting 68g of the intermediate product 1 into 50ml of 1% sodium hyaluronate aqueous solution, adding EDCI 0.5g, stirring at room temperature for 3 hours, taking out, and washing with deionized water to obtain sodium hyaluronate grafted latex, namely the intermediate product 2.
Placing 1.5g of polyvinyl alcohol into 100ml of 20% DMSO aqueous solution, heating to 100 ℃, stirring until the polyvinyl alcohol is dissolved clearly, adding 1.5g of organic silicon quaternary ammonium salt (2-triethoxysilylpropylalkoxy-1, 3-didodecyldimethylammonium propane dichloride (CAS: 27668-53-7)), stirring completely, and standing for defoaming to obtain a transparent organic silicon quaternary ammonium salt polyvinyl alcohol crosslinking solution;
adding 100g of the intermediate product 2 into 500ml of organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution, soaking for 2 hours, taking out, placing in 100 ℃ water, ultrasonically cleaning for 2 minutes, freezing for 24 hours at-20 ℃, taking out, recovering to room temperature, and repeating for three times to obtain the product.
Example 3
10g of titanium alloy sheet is placed in 50ml of 30% hydrogen peroxide solution, the titanium alloy sheet is soaked for 48h at room temperature, the titanium alloy sheet is taken out and placed in a forced air drying oven for drying at 50-55 ℃, silane coupling agent KH-791 g is dissolved in 8ml of absolute ethyl alcohol, the titanium alloy sheet after oxidation modification is added, ammonia water is dripped to adjust the pH value to 9-10, the titanium alloy sheet is continuously soaked for 1-2 h, the titanium alloy sheet is taken out and ultrasonically cleaned for 20min by using medicinal purified water, and the grafted titanium alloy sheet is placed at 50-55 ℃ for drying, so that an intermediate product 1 can be obtained.
And (3) putting 68g of the intermediate product 1 into 50ml of 1% sodium hyaluronate aqueous solution, adding 0.5g of EDCI, stirring at room temperature for 3h, taking out, and washing with deionized water to obtain a sodium hyaluronate grafted titanium alloy sheet, namely the intermediate product 2.
Placing 1.5g of polyvinyl alcohol into 100ml of 20% DMSO aqueous solution, heating to 100 ℃, stirring until the solution is clear, adding 1.5g of organosilicon quaternary ammonium salt (2-triethoxysilylpropanoxy-1, 3-didodecyldimethylammonium propane dichloride (CAS: 27668-53-7)), stirring completely, and standing for defoaming to obtain organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution;
adding 100g of the intermediate product 2 into 400ml of organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution, soaking for 2 hours, taking out, placing in 100 ℃ water, ultrasonically cleaning for 2 minutes, freezing for 24 hours at-20 ℃, taking out, recovering to room temperature, and repeating for three times to obtain the product.
Effects of the embodiment
In order to verify the performance of the antibacterial lubricating coating prepared by the application, the application provides an effect example.
Antibacterial property:
the antibacterial performance test was performed on examples 1-3 according to GB/T15979 appendix C test method, the test results are shown in Table 1:
table 1 examples 1-3 antimicrobial lubricating coating antimicrobial performance testing
As can be seen from Table 1, the coating can effectively reduce the growth of microorganisms on the surface of the material, so that the coating has good antibacterial performance.
Contact angle test:
contact angle tests were carried out according to GB/T30447 for examples 1-3, the results of which are given in Table 2.
Table 2 examples 1-3 contact Angle Performance test
| Experimental group | Static contact angle of water | Dynamic contact angle of water |
| Example 1 | 109° | 9° |
| Silica gel | 80° | 2° |
| Example 2 | 110° | 8° |
| Latex emulsion | 89° | 3° |
| Example 3 | 120° | 10° |
| Titanium alloy sheet | 93° | 2° |
As can be seen from Table 2, the antibacterial lubricating coatings prepared in the embodiments 1-3 of the present application have a large contact angle, and can effectively reduce the adhesion of pollutants such as moisture, microorganisms, blood stains and the like on the surface of the material, thereby inhibiting the bacterial growth on the surface of the material.
Biological evaluation
Examples 1-3 were evaluated biologically according to GB/T16886 and the results are shown in Table 3.
Table 3 examples 1-3 biological evaluation
As can be seen from Table 3, the antibacterial lubricating coatings prepared in examples 1-3 of the present application can significantly reduce cytotoxicity caused by the materials themselves and reduce the release of harmful components to human bodies. Reduce the toxicity of the medical material and improve the clinical safety of the medical material.
Claims (10)
1. A preparation method of a biomedical coating material with antibacterial and lubricating functions is characterized by comprising the following steps:
(1) Carrying out oxidation reaction on the substrate material under the action of an oxidant, and drying after the reaction is finished to obtain an oxidized substrate material; under the condition that the pH value is 9-10, reacting the oxidized substrate material with a silane coupling agent, and washing and drying the substrate material and the silane coupling agent in sequence after the reaction is finished to obtain an intermediate product 1;
(2) Firstly, adding the intermediate product 1 into a sodium hyaluronate solution, then adding a coupling agent, reacting at room temperature for 2-4h, and washing and drying after the reaction is finished to obtain an intermediate product 2;
(3) Dissolving polyvinyl alcohol and organosilicon quaternary ammonium salt in a DMSO (dimethyl sulfoxide) aqueous solution, and heating to 80-120 ℃ to obtain a transparent organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution;
(4) Adding the intermediate product 2 obtained in the step (2) into a transparent organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution, soaking for 2-4h at 80-120 ℃, taking out, placing in water at 80-100 ℃ for ultrasonic cleaning, placing in water at-30-10 ℃ for freezing for 20-24 h after cleaning, taking out, recovering the room temperature, and repeating for three times to obtain the target product.
2. The method of claim 1, wherein: the oxidant used in the step (1) is 30% hydrogen peroxide, and the silane coupling agent KH-791 is used; wherein the mass ratio of the substrate material to the oxidant to the silane coupling agent is 5-15: 45 to 55:5 to 30.
3. The method of claim 2, wherein: the mass ratio of the substrate material to the oxidant to the silane coupling agent is 8-12: 48 to 52:8 to 24.
4. The method of claim 1, wherein: the substrate material in the step (1) is any one of silica gel, latex and titanium alloy.
5. The production method according to claim 1, characterized in that: the coupling agent in the step (2) is EDCI.
6. The production method according to claim 1 or 5, characterized in that: the mass ratio of the intermediate product 1, the sodium hyaluronate solution and the coupling agent in the step (2) is 0.5-1: 0.3 to 0.7:0.01 to 1;
preferably, the following components: the mass ratio of the intermediate product 1 to the sodium hyaluronate solution to the coupling agent is 0.5-1: 0.5:0.05; wherein the mass percent of the sodium hyaluronate solution is 0.5-1.5%.
7. The method of claim 1, wherein: in the step (3), the mass ratio of the polyvinyl alcohol to the organosilicon quaternary ammonium salt to the DMSO aqueous solution is 1-3: 1 to 3:100, the DMSO content in the DMSO aqueous solution is 15-25 wt%.
8. The production method according to claim 1 or 7, characterized in that: in the step (3), the organosilicon quaternary ammonium salt is 2-triethoxysilylpropanoxy-1, 3-didodecyldimethylammonium propane dichloride.
9. The production method according to claim 1, characterized in that: the mass volume ratio of the intermediate product 2 to the organosilicon quaternary ammonium salt polyvinyl alcohol crosslinking solution is (1-1.1) g: (4-10) mL.
10. A biomedical coating material with antibacterial and lubricating functions is characterized in that: the material is prepared by the method of any one of claims 1 to 9.
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Citations (5)
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|---|---|---|---|---|
| US20120196953A1 (en) * | 2009-08-15 | 2012-08-02 | Nicoias Ziolkowski | Antimicrobial Quaternary Ammonium Organosilane Compositions |
| CN109825835A (en) * | 2019-04-11 | 2019-05-31 | 重庆大学 | Surface has silane/magnesium of Sodium Hyaluronate composite coating and the preparation method of magnesium alloy |
| CN110064070A (en) * | 2019-06-17 | 2019-07-30 | 董英 | Containing organic quaternary ammonium salt or with silane end organic quaternary ammonium salt anti-bacterial hydrogel and preparation method thereof |
| CN114015265A (en) * | 2021-10-29 | 2022-02-08 | 厦门赋源高科技有限公司 | Long-acting antibacterial coating material and preparation method thereof |
| CN114316350A (en) * | 2021-12-31 | 2022-04-12 | 南京神奇科技开发有限公司 | Organosilicon quaternary ammonium salt blood-sucking sponge with antibacterial function and preparation method thereof |
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- 2022-09-16 CN CN202211133793.5A patent/CN115581817A/en active Pending
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|---|---|---|---|---|
| US20120196953A1 (en) * | 2009-08-15 | 2012-08-02 | Nicoias Ziolkowski | Antimicrobial Quaternary Ammonium Organosilane Compositions |
| CN109825835A (en) * | 2019-04-11 | 2019-05-31 | 重庆大学 | Surface has silane/magnesium of Sodium Hyaluronate composite coating and the preparation method of magnesium alloy |
| CN110064070A (en) * | 2019-06-17 | 2019-07-30 | 董英 | Containing organic quaternary ammonium salt or with silane end organic quaternary ammonium salt anti-bacterial hydrogel and preparation method thereof |
| CN114015265A (en) * | 2021-10-29 | 2022-02-08 | 厦门赋源高科技有限公司 | Long-acting antibacterial coating material and preparation method thereof |
| CN114316350A (en) * | 2021-12-31 | 2022-04-12 | 南京神奇科技开发有限公司 | Organosilicon quaternary ammonium salt blood-sucking sponge with antibacterial function and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| 关志宇主编: "药物制剂辅料与包装材料", 中国医药科技出版社, pages: 97 * |
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