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Halide amine antibacterial agent based on cyanuric acid and synthesis method and application thereof

A synthesis method and antibacterial agent technology, applied in the application field of preparing antibacterial materials, can solve the problems of increased finishing and wastewater treatment costs, potential safety hazards of flammable organic co-solvents, poor water solubility of synthetic products, etc., and achieve low production costs and excellent Antibacterial performance, high product yield effect

Active Publication Date: 2013-04-24
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the existing haloamine antibacterial agents still have the following problems in practical application: the price of synthetic raw materials is relatively expensive; the reaction conditions are harsh (such as high temperature and long reaction time), the production process is complicated, and the cost is high; the yield is low; Synthetic products have poor water solubility, and a large amount of co-solvents must be added to help dissolve them, which increases the cost of finishing and wastewater treatment, and these flammable organic co-solvents also have potential safety hazards; some chloramine antibacterial agents are based on N-hydroxymethyl As an active group, there is still the problem of formaldehyde release during use

Method used

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  • Halide amine antibacterial agent based on cyanuric acid and synthesis method and application thereof
  • Halide amine antibacterial agent based on cyanuric acid and synthesis method and application thereof
  • Halide amine antibacterial agent based on cyanuric acid and synthesis method and application thereof

Examples

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Effect test

Embodiment 1

[0043] Synthesis of Halamine Antibacterial Agent 1,3-Dichloro-5-(2,3-Dihydroxypropyl)-S-Triazinetrione

[0044] 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 5.50g (0.05 mol) 3-chloroglycerin, fully stirred and reacted at room temperature (25°C) for 8 hours, adjusted the pH to 6.0 with dilute hydrochloric acid; used a rotary evaporator to remove the water in the solution after the reaction, and dissolved the obtained solid in ethanol, according to the conventional method Filter to remove the synthetic by-product sodium chloride, and then remove the ethanol in the filtrate by a rotary evaporator to obtain the water-soluble colorless oily haloamine antibacterial agent precursor 1-(2,3-dihydroxypropyl)-S- Triazinetrione (yield: 89%); finally add this precursor to a sodium hypochlorite solut...

Embodiment 2

[0046] Synthesis of Halamine Antibacterial Agent 1,3-Dichloro-5-(3-Hydroxypropyl)-S-Triazinetrione

[0047] 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, then add 5.6g of potassium hydroxide, continue stirring until the cyanuric acid is completely dissolved, slowly add 4.73g ( 0.05mol) 1-chloropropanol, fully stirred and reacted at 10°C for 10 hours, adjusted the pH to 7.0 with dilute hydrochloric acid; removed the water in the solution after the reaction with a rotary evaporator, and dissolved the obtained solid in ethanol, followed by conventional methods Filter to remove the synthetic by-product potassium chloride, and then remove the ethanol in the filtrate by a rotary evaporator to obtain a water-soluble colorless oily haloamine antibacterial agent precursor 1-(3-hydroxypropyl)-S-triazinetrione (yield 79%); finally add the precursor to a sodium hypochlorite solution with a concentration...

Embodiment 3

[0049] Synthesis of Halamine Antibacterial Agent 1-Chloro-3-Hydroxymethyl-5-(2,3-Dihydroxypropyl)-S-Triazinetrione

[0050] 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 8g of sodium hydroxide, continue to stir until 1-hydroxymethyl-S-triazinetrione is completely dissolved, slowly add 11.0g (0.1mol) of 3-chloroglycerin dropwise, and fully stir at 40°C for 9h , adjust the pH value to 6.0 with dilute hydrochloric acid; remove the moisture in the solution after the reaction with a rotary evaporator, and dissolve the resulting solid in ethanol, filter according to conventional methods, remove the synthetic by-product sodium chloride, and then pass through the rotary evaporator Remove the ethanol in the filtrate to obtain the water-soluble colorless...

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Abstract

The invention provides a halide amine antibacterial agent based on cyanuric acid and a synthesis method and an application thereof. The antibacterial agent is a compound of the structure of formula (I) or formula (II). The synthesis method comprises the steps of taking chlorohydrins or cyanuric acid (or derivative thereof) as raw material, reacting for 8-10 hours at 10-40DEG C, removing purities through filtration, obtaining a precursor of halide amine antibacterial agent of the structure of formula (III) or formula (IV), and finally obtaining the product of halide amine antibacterial agent through halogenation reaction. The application of the halide amine antibacterial agent in the preparation of antibacterial material is as follows: working solution prepared by the precursor of the halide amine antibacterial agent and cross-linking agent is used for trimming the material to be treated, then the material is taken out for drying and treating for 3-30 minutes at a high temperature of 100-180DEG C, and the antibacterial material is processed after halogenation. The reaction condition is mild, the technology is simple, the material is cheap and easy to obtain, the halide amine antibacterial agent synthesized by the method and the precursor thereof have a good water solubility and high yield, is environment friendly, and can be used for manufacturing antibacterial material with an excellent 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 cyanuric acid-based haloamine heterocyclic antibacterial agent, 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 and mold-causing harmful microorganisms in the human living environment. They can spread through various materials and product surfaces such as fibers, plastics, rubber, and paper, threatening human health. The use of long-lasting antibacterial materials is the simplest, safest and most effective way to effectively prevent the growth, reproduction, spread and spread of harmful microorganisms, and the core of antibacterial materials is the antibacterial agent loaded on them. Common antibacterial agents currently on the market include heavy metals, benzene chlorides, quaternary ammoniu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/36A01N43/64A01P1/00D06M13/364C09D5/14
Inventor 任学宏马凯凯
Owner JIANGNAN UNIV
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