CN110845754A - Antibacterial modification method of high polymer material - Google Patents
Antibacterial modification method of high polymer material Download PDFInfo
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- CN110845754A CN110845754A CN201911263595.9A CN201911263595A CN110845754A CN 110845754 A CN110845754 A CN 110845754A CN 201911263595 A CN201911263595 A CN 201911263595A CN 110845754 A CN110845754 A CN 110845754A
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- polymer material
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- diazomethane
- dichloromethane
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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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
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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
- C08J2300/00—Characterised by the use of unspecified polymers
Abstract
The invention discloses an antibacterial modification method of a high polymer material, which comprises the following steps: a step of preparing diazomethane having a hydroxyl group; carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups; and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material. According to the invention, the surface of the high polymer material is chemically modified by diazomethane with hydroxyl groups, so that the surface performance of the high polymer material is favorably improved, meanwhile, the environment-friendly isobornyl acrylate is used for modifying the high polymer material, and a good antibacterial layer is formed on the surface of the high polymer material, so that a bacterial biofilm is prevented from being formed on the surface of the high polymer material, and the condition that the implant fails or the patient is infected is prevented.
Description
Technical Field
The invention relates to the related field of antibacterial modification technology, in particular to an antibacterial modification method of a high polymer material.
Background
At present, the biggest problem of the implanted/interventional medical polymer material is that bacteria easily adhere to the surface and form a biofilm during clinical application, thereby causing infection, resulting in surgery and medical accidents. According to the preliminary statistics of the national institutes of health, 80% of bacterial diseases are related to medical materials. Bacterial biofilms are ubiquitous in artificial devices in the body and are extremely resistant and immune-evasive, and even hundreds of times the normal dose of drug cannot be effectively eliminated, often endangering the life of the patient. In the case of the cardiovascular system, the mortality rate from infection of artificial devices is close to 100%. Therefore, obtaining a medical polymer material with good antibacterial property and high safety becomes a problem to be solved in the current medicine, and is a research hotspot in the cross field of traditional subjects such as chemistry, materials science, biology and the like.
In biomedical and engineering applications, adhesion of bacteria to the surface of the material and the subsequent formation of bacterial biofilms is a very serious problem, potentially leading to implant failure or patient infection.
Therefore, an antibacterial modification method of the high polymer material is provided.
Disclosure of Invention
The present invention aims to provide an antibacterial modification method for polymer materials, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention adopts the following technical scheme:
an antibacterial modification method of a high polymer material comprises the following steps:
a step of preparing diazomethane having a hydroxyl group;
carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups;
and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material.
Preferably, the diazomethane with the group is prepared as follows:
the benzoyl chloride and alcoholic hydroxyl are taken as raw materials and are obtained by Friedel-crafts reaction, hydrazonation reaction and oxidation reaction in sequence.
Preferably, the diazomethane with the group is prepared as follows:
dissolving alcoholic hydroxyl in dichloromethane, then dropwise adding benzoyl chloride, stirring at room temperature for reaction after dropwise adding, washing after the reaction is finished, and drying, filtering and purifying a lower-layer organic phase to obtain a compound 1;
dissolving the compound 1 in absolute ethyl alcohol, adding hydrazine hydrate, then dropwise adding acetic acid, and carrying out reflux reaction; after the reaction is completed, extracting with dichloromethane, combining organic phases, washing, drying the lower organic phase, and performing rotary evaporation to obtain a compound 2;
dissolving the compound 2 in dichloromethane, sequentially adding manganese dioxide, potassium hydroxide and sodium sulfate, and reacting under the conditions of no light and at the temperature of
Stirring and reacting at room temperature, after the reaction is finished, filtering and rotary evaporating to obtain a compound 3, namely the diazomethane with the hydroxyl group.
Preferably, diazomethane with hydroxyl groups is dissolved in dichloromethane solution, and a high polymer material is added to fully soak the high polymer material; then, removing dichloromethane by evaporation to ensure that diazomethane with hydroxyl groups is uniformly adsorbed on the surface of the high polymer material; the chemical modification was completed at 120-125 ℃ for 20 minutes.
Preferably, after the chemical modification is finished, washing with dichloromethane for 20-30 minutes, and after the washing is finished, drying at 90-95 ℃ is finished.
Preferably, a step of performing an Ag — S coordination reaction using isobornyl acrylate and the chemically modified polymer material;
isobornyl acrylate was dissolved in dichloromethane and the ratio of isobornyl acrylate to dichloromethane was (5-12) g: 70ml, adding the chemically modified high polymer material, soaking and stirring for 5-7 hours at 80-120 ℃ to fully generate Ag-S coordination reaction, and washing and drying after the reaction is finished to finish the antibacterial modification of the high polymer material.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, the surface of the high polymer material is chemically modified by diazomethane with hydroxyl groups, so that the surface performance of the high polymer material is favorably improved, meanwhile, the environment-friendly isobornyl acrylate is used for modifying the high polymer material, and a good antibacterial layer is formed on the surface of the high polymer material, so that a bacterial biofilm is prevented from being formed on the surface of the high polymer material, and the condition that the implant fails or the patient is infected is prevented.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
The invention will be further illustrated with reference to specific examples, which are provided solely for the purpose of better understanding the present invention.
Example one
The invention also provides an antibacterial modification method of the high polymer material, which comprises the following steps:
a step of preparing diazomethane having a hydroxyl group;
carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups;
and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
the benzoyl chloride and alcoholic hydroxyl are taken as raw materials and are obtained by Friedel-crafts reaction, hydrazonation reaction and oxidation reaction in sequence.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
dissolving alcoholic hydroxyl in dichloromethane, then dropwise adding benzoyl chloride, stirring at room temperature for reaction after dropwise adding, washing after the reaction is finished, and drying, filtering and purifying a lower-layer organic phase to obtain a compound 1;
dissolving the compound 1 in absolute ethyl alcohol, adding hydrazine hydrate, then dropwise adding acetic acid, and carrying out reflux reaction; after the reaction is completed, extracting with dichloromethane, combining organic phases, washing, drying the lower organic phase, and performing rotary evaporation to obtain a compound 2;
dissolving the compound 2 in dichloromethane, sequentially adding manganese dioxide, potassium hydroxide and sodium sulfate, and reacting under the conditions of no light and at the temperature of
Stirring and reacting at room temperature, after the reaction is finished, filtering and rotary evaporating to obtain a compound 3, namely the diazomethane with the hydroxyl group.
Dissolving diazomethane with hydroxyl groups in a dichloromethane solution, and adding a high polymer material to fully soak the high polymer material; then, removing dichloromethane by evaporation to ensure that diazomethane with hydroxyl groups is uniformly adsorbed on the surface of the high polymer material; the chemical modification was completed at 120-125 ℃ for 20 minutes.
Wherein, after the chemical modification is finished, washing with dichloromethane for 20-30 minutes, and after the washing is finished, drying at 90-95 ℃.
Wherein, a step of performing Ag-S coordination reaction between isobornyl acrylate and a chemically modified polymer material;
isobornyl acrylate was dissolved in dichloromethane and the ratio of isobornyl acrylate to dichloromethane was 5 g: 70ml, adding the chemically modified high polymer material, soaking and stirring for 5-7 hours at 80-120 ℃ to fully generate Ag-S coordination reaction, and washing and drying after the reaction is finished to finish the antibacterial modification of the high polymer material.
Example two
The invention also provides an antibacterial modification method of the high polymer material, which comprises the following steps:
a step of preparing diazomethane having a hydroxyl group;
carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups;
and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
the benzoyl chloride and alcoholic hydroxyl are taken as raw materials and are obtained by Friedel-crafts reaction, hydrazonation reaction and oxidation reaction in sequence.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
dissolving alcoholic hydroxyl in dichloromethane, then dropwise adding benzoyl chloride, stirring at room temperature for reaction after dropwise adding, washing after the reaction is finished, and drying, filtering and purifying a lower-layer organic phase to obtain a compound 1;
dissolving the compound 1 in absolute ethyl alcohol, adding hydrazine hydrate, then dropwise adding acetic acid, and carrying out reflux reaction; after the reaction is completed, extracting with dichloromethane, combining organic phases, washing, drying the lower organic phase, and performing rotary evaporation to obtain a compound 2;
dissolving the compound 2 in dichloromethane, sequentially adding manganese dioxide, potassium hydroxide and sodium sulfate, and reacting under the conditions of no light and at the temperature of
Stirring and reacting at room temperature, after the reaction is finished, filtering and rotary evaporating to obtain a compound 3, namely the diazomethane with the hydroxyl group.
Dissolving diazomethane with hydroxyl groups in a dichloromethane solution, and adding a high polymer material to fully soak the high polymer material; then, removing dichloromethane by evaporation to ensure that diazomethane with hydroxyl groups is uniformly adsorbed on the surface of the high polymer material; the chemical modification was completed at 120-125 ℃ for 20 minutes.
Wherein, after the chemical modification is finished, washing with dichloromethane for 20-30 minutes, and after the washing is finished, drying at 90-95 ℃.
Wherein, a step of performing Ag-S coordination reaction between isobornyl acrylate and a chemically modified polymer material;
isobornyl acrylate was dissolved in dichloromethane and the ratio of isobornyl acrylate to dichloromethane was 6 g: 70ml, adding the chemically modified high polymer material, soaking and stirring for 5-7 hours at 80-120 ℃ to fully generate Ag-S coordination reaction, and washing and drying after the reaction is finished to finish the antibacterial modification of the high polymer material.
EXAMPLE III
The invention also provides an antibacterial modification method of the high polymer material, which comprises the following steps:
a step of preparing diazomethane having a hydroxyl group;
carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups;
and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
the benzoyl chloride and alcoholic hydroxyl are taken as raw materials and are obtained by Friedel-crafts reaction, hydrazonation reaction and oxidation reaction in sequence.
Wherein, the preparation steps of the diazomethane with the groups are as follows:
dissolving alcoholic hydroxyl in dichloromethane, then dropwise adding benzoyl chloride, stirring at room temperature for reaction after dropwise adding, washing after the reaction is finished, and drying, filtering and purifying a lower-layer organic phase to obtain a compound 1;
dissolving the compound 1 in absolute ethyl alcohol, adding hydrazine hydrate, then dropwise adding acetic acid, and carrying out reflux reaction; after the reaction is completed, extracting with dichloromethane, combining organic phases, washing, drying the lower organic phase, and performing rotary evaporation to obtain a compound 2;
dissolving the compound 2 in dichloromethane, sequentially adding manganese dioxide, potassium hydroxide and sodium sulfate, and reacting under the conditions of no light and at the temperature of
Stirring and reacting at room temperature, after the reaction is finished, filtering and rotary evaporating to obtain a compound 3, namely the diazomethane with the hydroxyl group.
Dissolving diazomethane with hydroxyl groups in a dichloromethane solution, and adding a high polymer material to fully soak the high polymer material; then, removing dichloromethane by evaporation to ensure that diazomethane with hydroxyl groups is uniformly adsorbed on the surface of the high polymer material; the chemical modification was completed at 120-125 ℃ for 20 minutes.
Wherein, after the chemical modification is finished, washing with dichloromethane for 20-30 minutes, and after the washing is finished, drying at 90-95 ℃.
Wherein, a step of performing Ag-S coordination reaction between isobornyl acrylate and a chemically modified polymer material;
isobornyl acrylate was dissolved in dichloromethane and the ratio of isobornyl acrylate to dichloromethane was 8 g: 70ml, adding the chemically modified high polymer material, soaking and stirring for 5-7 hours at 80-120 ℃ to fully generate Ag-S coordination reaction, and washing and drying after the reaction is finished to finish the antibacterial modification of the high polymer material.
Tests on the first, second and third examples show that the method can perform antibacterial modification on the high polymer material.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (6)
1. An antibacterial modification method of a high polymer material is characterized by comprising the following steps:
a step of preparing diazomethane having a hydroxyl group;
carrying out chemical modification on the surface of the high polymer material by using diazomethane with thioether groups;
and a step of performing an Ag-S coordination reaction using isobornyl acrylate and the chemically modified polymer material.
2. The method for antibacterial modification of a polymer material according to claim 1, wherein the diazomethane having a group is prepared by the following steps:
the benzoyl chloride and alcoholic hydroxyl are taken as raw materials and are obtained by Friedel-crafts reaction, hydrazonation reaction and oxidation reaction in sequence.
3. The method for antibacterial modification of a polymer material according to claim 1, wherein the diazomethane having a group is prepared by the following steps:
dissolving alcoholic hydroxyl in dichloromethane, then dropwise adding benzoyl chloride, stirring at room temperature for reaction after dropwise adding, washing after the reaction is finished, and drying, filtering and purifying a lower-layer organic phase to obtain a compound 1;
dissolving the compound 1 in absolute ethyl alcohol, adding hydrazine hydrate, then dropwise adding acetic acid, and carrying out reflux reaction; after the reaction is completed, extracting with dichloromethane, combining organic phases, washing, drying the lower organic phase, and performing rotary evaporation to obtain a compound 2;
dissolving the compound 2 in dichloromethane, sequentially adding manganese dioxide, potassium hydroxide and sodium sulfate, and reacting under the conditions of no light and at the temperature of
Stirring and reacting at room temperature, after the reaction is finished, filtering and rotary evaporating to obtain a compound 3, namely the diazomethane with the hydroxyl group.
4. The method of claim 1, wherein diazomethane with hydroxyl groups is dissolved in dichloromethane solution, and the polymer material is added to fully wet the polymer material; then, removing dichloromethane by evaporation to ensure that diazomethane with hydroxyl groups is uniformly adsorbed on the surface of the high polymer material; the chemical modification was completed at 120-125 ℃ for 20 minutes.
5. The method of claim 1, wherein the polymer material is washed with dichloromethane for 20-30 min after the chemical modification, and dried at 90-95 ℃.
6. The method of claim 1, wherein the polymer material is chemically modified with isobornyl acrylate to perform an Ag-S coordination reaction;
isobornyl acrylate was dissolved in dichloromethane and the ratio of isobornyl acrylate to dichloromethane was (5-12) g: 70ml, adding the chemically modified high polymer material, soaking and stirring for 5-7 hours at 80-120 ℃ to fully generate Ag-S coordination reaction, and washing and drying after the reaction is finished to finish the antibacterial modification of the high polymer material.
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Citations (4)
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|---|---|---|---|---|
| TWI277678B (en) * | 2006-06-30 | 2007-04-01 | Taiwan Textile Res Inst | Antibiotic and deodorant material and preparation method thereof |
| JP2009256345A (en) * | 2008-03-26 | 2009-11-05 | Kochi Univ | Silver cobalt complex and antibacterial or antifungal agent |
| CN102016814A (en) * | 2005-06-17 | 2011-04-13 | 北卡罗来纳大学查珀尔希尔分校 | Nanoparticle fabrication methods, systems, and materials |
| CN108755112A (en) * | 2018-06-27 | 2018-11-06 | 济南鸿湾生物技术有限公司 | A kind of antibacterial modified method of high molecular material |
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2019
- 2019-12-11 CN CN201911263595.9A patent/CN110845754A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102016814A (en) * | 2005-06-17 | 2011-04-13 | 北卡罗来纳大学查珀尔希尔分校 | Nanoparticle fabrication methods, systems, and materials |
| TWI277678B (en) * | 2006-06-30 | 2007-04-01 | Taiwan Textile Res Inst | Antibiotic and deodorant material and preparation method thereof |
| JP2009256345A (en) * | 2008-03-26 | 2009-11-05 | Kochi Univ | Silver cobalt complex and antibacterial or antifungal agent |
| CN108755112A (en) * | 2018-06-27 | 2018-11-06 | 济南鸿湾生物技术有限公司 | A kind of antibacterial modified method of high molecular material |
Non-Patent Citations (1)
| Title |
|---|
| 刘国杰: "《现代涂料工艺新技术》", 30 April 2000, 中国轻工业出版社 * |
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