Reaction type halamine antiseptic, preparation method, and applications thereof

An antibacterial agent and a reactive technology, which are applied in the field of reactive halamine antibacterial agents and their preparation, can solve the problems of poor water solubility of the antibacterial agent precursor, and poor washing and regeneration performance, and achieve excellent bacteriostatic and sterilizing functions. , low price, the effect of improving antibacterial activity

Inactive Publication Date: 2015-03-11
ZHANGJIAGANG HUYI DYEING & FINISHING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Cotton fibers contain many active hydroxyl groups, which can react with some reactive substances, which points out the direction for the selection and application of antibacterial agents. The patent application number 201210293286.8 "A haloamine antibacterial agent and its Preparation method and application" and the patent of application number 201310475978.9 "A reactive haloamine antibacterial agent and its synthesis method and application" by combining the haloamine antibacterial carrier 2,2,6,6-tetramethylpiperidinol with three Polycyanuric fluoride or cyanuric chloride reacts to generate dichloride and a chloro-s-triaz...

Method used

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  • Reaction type halamine antiseptic, preparation method, and applications thereof
  • Reaction type halamine antiseptic, preparation method, and applications thereof
  • Reaction type halamine antiseptic, preparation method, and applications thereof

Examples

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Effect test

Embodiment 1

[0039] Haloamine antibacterial agent precursor 2-chloro-4-(4-sulfoanilino)-6-(3-hydroxypropyl-5,5-dimethylhydantoin)-1,3,5-tri Preparation of oxazine:

[0040] Weigh 6.4g of 5,5-dimethylhydantoin and 2.8g of potassium hydroxide and reflux in water for 10min, then add 4.73g of 3-chloro-1-propanol, continue the reaction for 12h, and remove the moisture by distillation under reduced pressure after the end. After washing with acetone, remove potassium chloride by filtration, distill under reduced pressure, and dry.

[0041] Weigh 9.22g cyanuric chloride, dissolve it in 100mL carbon tetrachloride, weigh 8.66g p-aminobenzenesulfonic acid and 2.65g sodium carbonate, dissolve it in 60mL water, mix the two in a 250mL three-necked flask and placed in an ice bath, and reacted for 1 hour at a pH value of 5.0 to 6.0, then poured 50 mL of the 3-hydroxypropyl-5,5-dimethylhydantoin solution obtained above into the reaction liquid, and the pH The value is 7.0-8.0, and the temperature is 40° ...

Embodiment 2

[0043] Haloamine antibacterial agent precursor 2-chloro-4-(4-sulfoanilino)-6-(3-hydroxypropyl-5,5-dimethylhydantoin)-1,3,5-tri Preparation of oxazine:

[0044] Weigh 6.4g of 5,5-dimethylhydantoin and 2g of sodium hydroxide and reflux in ethanol for 10min, then add 4.73g of 3-chloro-1-propanol and continue the reaction for 24h. After washing with ethanol, filter sodium chloride, distill under reduced pressure, and dry.

[0045] Weigh 9.22g of cyanuric chloride, dissolve it in 100mL of chloroform, then pour 50mL of the 3-hydroxypropyl-5,5-dimethylhydantoin solution obtained above into it, at a pH of 7.0 to 8.0 React under the conditions for 3 hours, then weigh 8.66g of p-aminobenzenesulfonic acid and 2.65g of sodium carbonate and dissolve them in 50mL of water, pour them into the above reaction solution, and react for 6 hours at a pH value of 5.0-6.0 and a temperature of 30°C. After the end, filter, wash with acetone and ice water, then dry and store.

Embodiment 3

[0047] Haloamine antibacterial agent precursor 2-fluoro-4-(4-sulfoanilino)-6-(3-hydroxypropyl-5,5-dimethylhydantoin)-1,3,5-tri Preparation of oxazine:

[0048] Weigh 6.4g of 5,5-dimethylhydantoin and 2g of sodium hydroxide in N,N-dimethylformamide, stir at 95°C for 10min, then add 4.73g of 3-chloro-1-propanol , continue the reaction for 18h, after the completion of vacuum distillation to remove N,N-dimethylformamide, wash with ethanol, filter sodium chloride, vacuum distillation, and dry.

[0049] Weigh 9.22g of cyanuric fluoride, dissolve it in 100mL of acetone, weigh 8.66g of p-aminobenzenesulfonic acid and 2.65g of sodium carbonate, dissolve it in 60mL of water, mix the two in a 250mL three-necked flask and place them together In an ice bath, react for 2 hours at a pH value of 5.0 to 6.0, then pour 50 mL of the 3-hydroxypropyl-5,5-dimethylhydantoin aqueous solution obtained above into it, and pour it into the above reaction The solution was reacted at a pH value of 7.0-8....

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Abstract

The invention discloses a reaction type halamine antiseptic. The structural formula of the antiseptic is represented in the description. In the structural formula, the R represents F or Cl, and the R1 and R2 individually represent Cl or Br. The preparation method comprises the following steps: (1) in an alkaline condition, reacting 5,5-dimethylhydantoin with 3-chloro-1-propanol to generate 3-hydroxypropyl-5,5-dimethylhydantoin; (2) carrying out one-step reaction between sodium sulfanilate and 3-hydroxypropyl-5,5-dimethylhydantoin to obtain a halamine antiseptic precursor (II); (3) reacting the halamine antiseptic precursor (II) with sodium hypochlorite so as to obtain the finished product of halamine antiseptic. The chlorine content of the textile processed by the antiseptic can reach 0.35%, the sterilizing rate on staphylococcus aureus can reach 100% in 10 minutes, and the sterilizing rate on escherichia coli O157:H7 can reach 100% within one minute. The operation is simple during the whole synthesis process, no toxic byproduct is generated, and the synthesis raw materials are cheap.

Description

technical field [0001] The invention belongs to the field of antibacterial technology, and in particular relates to a reactive haloamine antibacterial agent and its preparation method and application. Background technique [0002] In recent years, with the improvement of people's living standards, antibacterial has become more and more important in many fields. In textiles, cotton fiber is widely liked by people for its good performance, but the good hygroscopicity of cotton fiber and the sugars contained in the fiber provide energy for microbial reproduction under certain conditions, and under certain conditions (including humidity, temperature, etc.) etc.), microorganisms can grow and reproduce rapidly. This not only affects the wearing performance of the fabric itself, but also endangers human health. Therefore, the antibacterial finishing of cotton fabrics is particularly important, and has received extensive attention from researchers. Many different types of antibact...

Claims

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Application Information

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IPC IPC(8): A01N43/66A01P1/00C07D403/12D06M13/358
Inventor 任学宏蒋之铭李蓉黄建军
Owner ZHANGJIAGANG HUYI DYEING & FINISHING
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