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Annular halamine type polymeric antibacterial agent containing quaternary ammonium group and preparation method and application of polymeric antibacterial agent

A technology of polymer antibacterial agent and cyclic halamine, which is applied in the synthesis of polymer antibacterial agent and antibacterial field, can solve the problems of high price of synthetic raw materials, less application range, easy penetration into the skin, etc., and achieves good cell compatibility. , excellent antibacterial properties, high antibacterial efficiency effect

Active Publication Date: 2016-05-25
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing halamine antibacterial agents still have the following problems in practical application: (1) the application range of halamine antibacterial agents is less at present, mainly focusing on textile fabrics and coatings; (2) small molecule halamine antibacterial agents The performance of the agent is unstable, it is easy to penetrate into the skin, and there is a safety hazard during use; (3) there is a possibility of increasing the hydrophobicity of the material after the material containing the antibacterial precursor is halogenated, which will limit the scope of use of the material in some aspects; (4) Most of the haloamine structures in the only haloamine antibacterial agent molecules containing quaternary ammonium groups are linear, with unstable performance, easy decomposition, and decreased utilization rate; (5) N-Cl bonds in the haloamine compounds and their Itself is prone to fracture under ultraviolet irradiation, and its ultraviolet stability is poor, resulting in a shorter maintenance time of antibacterial properties of antibacterial materials under ultraviolet irradiation conditions, and a decrease in utilization rate; (6) some chloramine antibacterial agents are based on N-hydroxymethyl As an active group, there is a problem of formaldehyde release during use; (7) the price of synthetic raw materials is relatively expensive, the reaction conditions are harsh, the yield is low, and the cost is high

Method used

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  • Annular halamine type polymeric antibacterial agent containing quaternary ammonium group and preparation method and application of polymeric antibacterial agent
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  • Annular halamine type polymeric antibacterial agent containing quaternary ammonium group and preparation method and application of polymeric antibacterial agent

Examples

Experimental program
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Embodiment 1

[0058] (1) Synthesis of cyclic small molecule haloamine antibacterial agent precursor: Weigh 12.9g (0.1mol) of 5,5-dimethylhydantoin in a 250mL round bottom flask, add 100mL of ethanol to dissolve it, and then add 4g (0.1mol) sodium hydroxide, put the round bottom flask in an oil bath environment and keep stirring, heat up to 100°C for 10 minutes, then cool down to 75°C, slowly add 14.34g (0.1mol) 1-bromo-2-chloroethyl Alkanes, condensed back to 10h. After the reaction is completed, the solvent is removed by rotary evaporation, the mixture of ethyl acetate and water is separated, and the ethyl acetate part is taken, purified and dried by rotary evaporation to obtain white crystals, which are ring-shaped small molecule haloamine antibacterial agents Precursor 3-(2'-chloroethyl)-5,5-dimethylhydantoin.

[0059] (2) Synthesis of high molecular self-polymer: Weigh 8g of dimethylaminoethyl methacrylate in a 100mL three-neck flask, add 20mL of ethanol solution, then add 0.08g of azo...

Embodiment 2

[0063] (1) Synthesis of cyclic small molecule haloamine antibacterial agent precursor: Weigh 12.9g (0.1mol) of 5,5-dimethylhydantoin in a 250mL round bottom flask, add 100mL of ethanol to dissolve it, and then add 4g (0.1mol) sodium hydroxide, put the round-bottomed flask in an oil bath environment and keep stirring, heat up to 80°C and react for 30min, slowly add 14.34g (0.1mol) 1-bromo-2-chloroethane dropwise, condense and reflux 8h. After the reaction is completed, the solvent is removed by rotary evaporation, the mixture of ethyl acetate and water is separated, and the ethyl acetate part is taken, purified and dried by rotary evaporation to obtain white crystals, which are ring-shaped small molecule haloamine antibacterial agents Precursor 3-(2'-chloroethyl)-5,5-dimethylhydantoin.

[0064] (2) Synthesis of high molecular self-polymer: Weigh 10g of dimethylaminoethyl methacrylate in a 100mL three-neck flask, add 15mL of ethanol solution, then add 0.1g of azobisisobutylcyan...

Embodiment 3

[0068] (1) Synthesis of cyclic small molecule haloamine antibacterial agent precursor: Weigh 12.9g (0.1mol) of 5,5-dimethylhydantoin in a 250mL round bottom flask, add 100mL of ethanol to dissolve it, and then add 4g (0.1mol) sodium hydroxide, put the round bottom flask in an oil bath environment and keep stirring, heat up to 90°C and react for 10min, then cool down to 80°C, slowly add 14.34g (0.1mol) 1-bromo-2-chloroethyl Alkanes, condensed and refluxed for 8h. After the reaction is completed, the solvent is removed by rotary evaporation, the mixture of ethyl acetate and water is separated, and the ethyl acetate part is taken, purified and dried by rotary evaporation to obtain white crystals, which are ring-shaped small molecule haloamine antibacterial agents Precursor 3-(2'-chloroethyl)-5,5-dimethylhydantoin.

[0069] (2) Synthesis of high molecular self-polymer: Weigh 8g of dimethylaminoethyl methacrylate in a 100mL three-neck flask, add 20mL of ethanol solution, then add ...

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Abstract

The invention provides an annular halamine type polymeric antibacterial agent containing quaternary ammonium group and preparation method and application of the polymeric antibacterial agent. The preparation method includes: synthesizing an annular micromolecular halamine type polymeric antibacterial agent precursor and a polymeric autopolymer; enabling the precursor and the polymeric autopolymer to be in substitution reaction to obtain a polymeric antibacterial agent precursor; halogenating to obtain the annular halamine type polymeric antibacterial agent. The application includes: dissolving the polymeric antibacterial agent precursor in N, N-dimethyl formamide, and mixing with a base material; adopting electrostatic spinning technology or conventional casting dissolving process to obtain a membrane containing the antibacterial agent precursor; soaking the membrane in a solution containing active halogen for halogenating reaction; taking the membrane out for water washing, and drying to obtain an antibacterial material. The preparation method is mild in reaction condition, raw materials are low in cost and easy to get, production cost is low, equipment is simple and convenient, and process operation is simple; the antibacterial agent prepared by the method has excellent antibacterial performance and is stable, safe and nontoxic.

Description

technical field [0001] The invention relates to the field of synthesis and antibacterial technology of polymer antibacterial agents, in particular to a cyclic haloamine polymer antibacterial agent containing quaternary ammonium groups, a synthesis method thereof, and an application of the antibacterial agent in preparing antibacterial materials. Background technique [0002] There are a large number of pathogenic microorganisms such as bacteria and fungi in the human living environment. Once too many pathogenic microorganisms invade the human body, it will bring serious hidden dangers to human health. At the same time, microorganisms will also cause the decomposition, deterioration and corruption of various materials, bringing to serious economic losses. In the fields of biomedicine and tissue engineering, if the substances that come into contact with the human body contain a certain amount of harmful microorganisms, they will breed germs, leading to infection and disease. ...

Claims

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Application Information

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IPC IPC(8): C08F120/34C08F8/44C08F8/20A01N43/50A01P1/00A01P3/00
CPCA01N43/50C08F8/20C08F8/44C08F120/34
Inventor 任学宏范晓燕李晓林
Owner JIANGNAN UNIV
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