Sulfonium salt cationic polymer with antibacterial property, preparation method and application

A cationic polymer and salt technology, applied in the directions of botanical equipment and methods, applications, fungicides, etc., can solve the problems of acute toxicity and skin irritation, poor broad-spectrum, low antibacterial activity, etc., and achieve good industrial application prospects , the effect of simple reaction route

Active Publication Date: 2021-09-21
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Researchers began to try to synthesize sulfonium salt polymers as antibacterial products, such as the synthesis of 4-vinylbenzyl tetramethylene sulfonium tetrafluoroborate polymers by Kanazaw et al. The results showed that this type of polymers was only effective against aureus Gram-positive bacteria including cocci have higher antibacterial activity, while Gram-negative bacteria including Escherichia coli have lower antibacterial activity and poor broad-spectrum
Although the tris(n-alkylphenyl)sulfonium salts (TAPSs) synthesized by Hirayama have high antibacterial activity, their acute toxicity and skin irritation are relatively strong.

Method used

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  • Sulfonium salt cationic polymer with antibacterial property, preparation method and application
  • Sulfonium salt cationic polymer with antibacterial property, preparation method and application
  • Sulfonium salt cationic polymer with antibacterial property, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] This example provides the preparation method of the sulfonium salt cationic polymer of the repeating unit shown in formula I-1, the specific operation is as follows:

[0072]

[0073] a. Weigh 1,6-hexanediol (10mmol) in a reaction flask, add epichlorohydrin (60mmol), then add tetrabutylammonium bromide (0.5mmol), sodium hydroxide (30mmol) and 0.2 mL of deionized water, the mixed solution was reacted at 40°C for 4 hours, after the reaction was completed, it was filtered, washed and dried to obtain 1,6-hexanediol diglycidyl ether;

[0074] b. Weigh 1,6-hexanediol diglycidyl ether (2.61mmol) and 1,8-octanedithiol (2.61mmol), dissolve in tetrahydrofuran / deionized water (9:1, 2.925mL) and mix solution, followed by adding triethylamine (3.91mmol), allowing it to react with stirring at room temperature for 24h to obtain an alternating copolymer containing repeating units shown in formula I-1-a;

[0075]

[0076] c. Weigh the alternating copolymer (1.58mmol) of the repea...

Embodiment 2

[0078] This example provides the preparation method of the sulfonium salt cationic polymer of the repeating unit shown in formula I-2, and the specific operation steps are as follows:

[0079]

[0080] a. Weigh 1,6-hexanediol (10mmol) in a reaction flask, add epichlorohydrin (60mmol), then add tetrabutylammonium bromide (0.5mmol), sodium hydroxide (30mmol) and 0.2 mL of deionized water, the mixed solution was reacted at 40°C for 4 hours, after the reaction was completed, it was filtered, washed and dried to obtain 1,6-hexanediol diglycidyl ether;

[0081] b. Weigh 1,6-hexanediol diglycidyl ether (2.61mmol) and 1,6-hexanedithiol (2.61mmol), dissolve in tetrahydrofuran / deionized water (9:1, 2.687mL) and mix solution, followed by adding triethylamine (3.91mmol), allowing it to react with stirring at room temperature for 24h to obtain an alternating copolymer containing repeating units shown in formula I-2-a;

[0082]

[0083] c. Weigh the alternating copolymer (1.582mmol) ...

Embodiment 3

[0085] This embodiment provides the preparation method of the sulfonium salt cationic polymer of the repeating unit shown in formula I-3, the specific operation is as follows:

[0086]

[0087] a. Weigh 1,8-octanediol (10mmol) in a reaction flask, add epichlorohydrin (60mmol), then add tetrabutylammonium bromide (0.5mmol), sodium hydroxide (30mmol) and 0.2 mL of deionized water, and place the mixed solution at 40°C for 4 hours. After the reaction, filter, wash and dry to obtain 1,8-octanediol diglycidyl ether;

[0088] b. Weigh 1,8-octanediol diglycidyl ether (0.776mmol) and 1,4-butanedithiol (0.776mmol), dissolve in tetrahydrofuran / deionized water (9:1, 0.961mL) and mix solution, followed by adding triethylamine (1.163mmol), allowing it to react with stirring at room temperature for 24h to obtain an alternating copolymer containing repeating units shown in formula I-3-a;

[0089]

[0090] c. Weigh the alternating copolymer (0.350 mmol) of the repeating unit shown in fo...

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Abstract

The invention provides a sulfonium salt cationic polymer with antibacterial performance, a preparation method and application. The sulfonium salt cationic polymer comprises sulfonium salt cationic repeating units. Compared with the prior art, the sulfonium salt cationic polymer with antibacterial performance has the following beneficial effects that the sulfonium salt cationic polymer containing a sulfonium salt structure in a main chain is designed, sulfonium salt cations in a molecular structure interact with an electronegative structure on the surface of a bacterial cell membrane, and other hydrophilic and hydrophobic groups in the molecular structure are matched to act on the bacterial cell membrane; bacterial cell membranes are disintegrated, so that bacteria are killed; the polymer has the advantages of high sterilization speed, excellent antibacterial effect, high sterilization activity and broad-spectrum antibacterial performance, and has the sterilization rate of 99.9% on gram-positive bacteria and gram-negative bacteria when the polymer concentration is 100 mug / mL. Besides, the sulfonium salt cationic polymer prepared according to the invention has excellent biocompatibility and low toxicity, and when the polymer concentration is greater than or equal to 5300 mug / mL, the red blood cell hemolysis rate can still be less than or equal to 50%.

Description

technical field [0001] The invention belongs to the field of antibacterial polymers, and in particular relates to a sulfonium salt cationic polymer with antibacterial properties, a preparation method and an application. Background technique [0002] Bacteria are common pathogens in infectious diseases and foodborne diseases, especially in areas where medical resources are scarce and public health is relatively poor. Bacterial infection has become one of the main health threats in recent years. Currently, the main treatment for the problem of bacterial infections is the use of antibiotics. However, due to the abuse of antibiotics in recent years, drug-resistant bacterial infections have been increasing worldwide. Therefore, it is imperative to develop new and efficient broad-spectrum antibacterial materials. [0003] Antibacterial materials refer to the general term for materials that can kill or inhibit the growth of microorganisms. Generally, they can be divided into the ...

Claims

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Application Information

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IPC IPC(8): C08G75/04A01N31/02A01P1/00A01P3/00
CPCC08G75/045C08G75/04A01N31/02
Inventor 饶静一赵靖华胡勇进王潇
Owner HUAZHONG UNIV OF SCI & TECH
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