Halamine antibacterial agent and synthetic method and application thereof

A synthesis method and technology for an antibacterial agent are applied in the synthesis and antibacterial fields of halamine compounds, which can solve the problems of increasing finishing costs and wastewater treatment costs, poor water solubility of synthetic products, and large reaction energy consumption, and reduce the cost of antibacterial finishing, The effect of high product yield and low reaction energy consumption

Inactive Publication Date: 2013-01-16
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the above-mentioned haloamine antibacterial agents also have some problems in practical application: (1) the synthetic raw materials such as chloroethyltriethoxysilane are expensive; (2) the synthetic reaction requires high-temperature reaction in an anhydrous organic system , the reaction energy consumption is large, the reaction time is long, and the production cost is high; (3) Most of the synthetic products have poor water solubility, and a large amount of co-solvent must be added when preparing the working solution for antibacterial finishing of materials, which increases the processing time. Cost and waste water treatment cost, and these flammable organic solvents are still dangerous during the finishing process; (4) Some chloramine antibacterial agents still have the problem of formaldehyde release during use

Method used

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  • Halamine antibacterial agent and synthetic method and application thereof
  • Halamine antibacterial agent and synthetic method and application thereof
  • Halamine antibacterial agent and synthetic method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Synthesis of Halamine Antibacterial Agent 1,3-Dichloro-5-epoxypropyl-S-triazinetrione

[0049] Weigh 6.45g (0.05mol) of cyanuric acid into a 250mL flat-bottomed flask, add 100mL of deionized water, stir evenly with a glass rod, add 4g of sodium hydroxide, continue stirring until the cyanuric acid is completely dissolved, slowly add 4.63g (0.05 mol) epichlorohydrin, fully stirred and reacted at room temperature (25°C) for 6 hours, and adjusted the pH value of the reaction solution to 6.5 with dilute hydrochloric acid; removed the water in the reaction solution with a rotary evaporator, and dissolved the obtained solid in dimethyl Dimethyl formamide (DMF), filtered according to the conventional method to remove the synthetic by-product sodium chloride, and then remove the DMF in the filtrate by a rotary evaporator to obtain a water-soluble colorless oily haloamine antibacterial agent precursor 1-epoxy Propyl-S-triazinetrione; Finally, add the precursor to a sodium hypochl...

Embodiment 2

[0051] Synthesis of Halamine Antibacterial Agent 1-Chloro-3,5-Diepoxypropyl-S-Triazinetrione

[0052] Weigh 6.45g (0.05mol) of cyanuric acid into a 250mL flat-bottomed flask, add 100mL of deionized water, stir evenly with a glass rod, add 5.6g of potassium hydroxide, continue stirring until the cyanuric acid is completely dissolved, slowly add 9.25g ( 0.1mol) of epichlorohydrin, fully stirred and reacted at 5°C for 12 hours, and adjusted the pH value of the reaction solution to 7.0 with dilute sulfuric acid; removed the water in the reaction solution with a rotary evaporator, and dissolved the obtained solid in ethanol, according to Filtrate by conventional method to remove the synthetic by-product potassium chloride, then remove the ethanol in the filtrate by rotary evaporator to obtain the water-soluble colorless oily haloamine antibacterial agent precursor 1,3-diepoxypropyl-S-tri Azitrione; finally add the precursor to a sodium hypochlorite solution with a concentration of ...

Embodiment 3

[0054] Synthesis of Halamine Antibacterial Agent 1-Chloro-3-Hydroxymethyl-5-Epoxypropyl-S-Triazinetrione

[0055] Weigh 15.9g (0.1mol) of 1-hydroxymethyl-S-triazinetrione (that is, a compound in which one of the hydrogen atoms of cyanuric acid is replaced by a hydroxymethyl group) into a 250mL flat-bottomed flask, add 100mL of deionized water, and use After the glass rod is stirred evenly, add 30g of sodium hydroxide, continue to stir until 1-hydroxymethyl-S-triazinetrione is completely dissolved, slowly add 9.25g (0.1mol) of epichlorohydrin, and fully stir at 50°C for 9h , and adjust the pH value of the reaction solution to 7.5 with dilute sulfuric acid; remove the water in the reaction solution with a rotary evaporator, and dissolve the obtained solid in dimethylacetamide (DMAC), and filter according to the conventional method to remove the synthetic by-product Product sodium chloride, removes ethanol in the filtrate by rotary evaporator again, obtains water-soluble colorles...

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Abstract

The invention provides a halamine antibacterial agent and a synthetic method and application thereof. The halamine antibacterial agent is a compound with a structure which is shown as a formula (I) or a formula (II). The synthetic method comprises the following steps of: reacting by taking epoxy chloropropane and cyanuric acid or a derivative of the cyanuric acid as synthetic raw materials at the temperature of between 5 and 50 DEG C for 6 to 12 hours, filtering, removing impurities to obtain a halamine antibacterial agent precursor with a structure which is shown as a formula (III) or a formula (IV), and performing halogenating reaction to obtain a finished product of the halamine antibacterial agent. According to the application of the halamine antibacterial agent to the preparation of an antibacterial material, the antibacterial material is prepared by the following steps of: treating a material to be treated by a working solution prepared from the halamine antibacterial agent precursor, taking the material out, drying, treating at the temperature of between 80 and 200 DEG C for 3 to 60 minutes, and performing halogenating reaction. According to the method, reaction condition is mild, a process is simple, and raw materials are low in cost and readily available; and the halamine antibacterial agent synthesized by the method and the halamine antibacterial agent precursor are water-soluble, high in yield, safe and non-toxic, and can be prepared into antibacterial textiles with high antibacterial performance.

Description

technical field [0001] The invention belongs to the technical field of synthesis and antibacterial of haloamine compounds, and in particular relates to a haloamine heterocyclic antibacterial agent, a synthesis method thereof, and an application of the antibacterial agent in preparing antibacterial materials. Background technique [0002] In the human living environment, there are a large number of pathogenic and harmful microorganisms that cause mildew and decay of materials, especially bacteria that pollute and breed on the surfaces of various materials and products such as fibers, plastics, rubber, and paper, which pose a great threat to human health. . To effectively prevent the growth, reproduction, spread and spread of harmful microorganisms and reduce the harm caused by them, the use of long-acting antibacterial materials is the simplest, safest and most effective method, and the core of antibacterial materials is the antibacterial agent loaded on them, so , has been ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D405/14A01N43/88A01P1/00D06M13/364D06M101/06
Inventor 任学宏马凯凯
Owner JIANGNAN UNIV
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