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Immobilized pyridine quaternary ammonium salt halamine precursor as well as synthesis method and application thereof

A synthesis method and a salt halide technology are applied in the field of immobilizable pyridinium quaternary ammonium salt halide precursor and its synthesis and application, which can solve the toxicity of aquatic organisms and other problems, achieve enhanced water solubility, realize regeneration, and solve bacteria The effect of antimicrobial resistance problems such as

Inactive Publication Date: 2017-03-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires pre-introduction of alkyne groups on the surface of cotton fabrics, and the "click" reaction requires copper ions (Cu 2+ / sodium ascorbate) as catalyst, and Cu 2+ Toxic to aquatic organisms

Method used

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  • Immobilized pyridine quaternary ammonium salt halamine precursor as well as synthesis method and application thereof
  • Immobilized pyridine quaternary ammonium salt halamine precursor as well as synthesis method and application thereof
  • Immobilized pyridine quaternary ammonium salt halamine precursor as well as synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0031] Weigh 3-hydroxypyridine (1.52g, 16mmol) into 100mL acetonitrile, stir to dissolve. Weigh anhydrous potassium carbonate (6.63g, 48mmol) into the system and heat to reflux for 4h. After adding 5,5-dimethylhydantoin and bromopropylhydantoin (4.98g, 20mmol) into the system, after reflux reaction for 4h, anhydrous potassium carbonate was removed by filtration, and acetonitrile was distilled off under reduced pressure. Using methanol / dichloromethane as the eluent, the organic phase containing the product was collected, and the solvent was removed under reduced pressure to obtain compound 2.

[0032] 1 H NMR (500 MHz, Chloroform-d) δ8.30 (dd, J = 2.7, 1.0 Hz, 1H), 8.21 (dd, J = 4.2, 1.8 Hz, 1H), 7.26–7.13 (m, 2H), 4.06 (t,J=6.0Hz,2H),3.73(t,J=6.8Hz,2H),2.23-2.09(m,2H),1.43(s,6H). 13 C NMR (126 MHz, Chloroform-d) δ177.13, 156.00, 154.93, 142.31, 138.10, 123.83, 121.19, 66.09, 58.71, 36.05, 27.88, 25.12.HRMS calcd.forC 13 h 17 N 3 o 3 [M+H] + 264.1270, found: 264.1343. ...

Embodiment 2

[0039] The cotton fabric was immersed in acetone for 60 min to remove oily substances and other impurities on the surface of the cotton fabric, and the desized cotton fabric was immersed in a solution containing antibacterial precursor compound 4 and placed for 15 min (mass concentration 4 wt%) , 1:1 ethanol / water mixed solvent), and then cured at 105°C for 60 min. Then the cotton fabric was washed several times with distilled water, soaked in saturated sodium chloride solution for 30 minutes, then washed several times with distilled water, immersed in 100 times diluted bleach water for 40 minutes, and then washed several times with deionized water to ensure that the fabric Free halogen ions are completely removed. Finally dry at 45°C and store in dark conditions.

[0040] The preparation and application process of antibacterial cotton fabric are as follows:

[0041]

[0042] Characterization:

[0043] Analysis of infrared images: attached figure 1 , compared with the u...

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Abstract

The invention discloses an immobilized pyridine quaternary ammonium salt halamine precursor I as well as a synthesis method and application thereof. The synthesis method comprises the following steps: preparing a compound III from 5,5-dimethyl hydantoin, dibromopropane and hydroxypyridine which serve as raw materials, and then carrying out backflow reaction with gamma-chloro(bromo, iodo) propyl triethoxy silane in acetonitrile for 7 to 48 hours to obtain an antimicrobial compound precursor I. The application of an antimicrobial in an antibacterial material comprises the following steps: preparing 1 to 5 percent by weight of a halamine precursor solution, modifying the surface of the material in an immobilized manner, and performing chlorination to obtain the antibacterial material. The synthesis method disclosed by the invention is easy to operate; with the introduction of a pyridine quaternary ammonium salt unit, the water solubility of the antibacterial agent is enhanced, and the use of an organic solvent in the preparation process of the antibacterial material is reduced. An antibacterial experiment shows that the prepared antibacterial material is relatively high in bactericidal activity against Gram-negative bacteria (E.coli ATCC25922) and Gram-positive bacteria (S.aureus ATCC25923). A formula is shown in the specification, wherein R is selected from Cl, Br or I, and n is an integer from 2 to 12.

Description

technical field [0001] The invention belongs to the synthesis and application field of immobilizable haloamine antibacterial agent precursors, and specifically relates to the synthesis of a class of immobilizable pyridinium quaternary ammonium salt halide precursors and the use of such antibacterial agent precursors in the preparation of antibacterial agents. Application in cotton textiles and other antibacterial materials. Background technique [0002] At present, the types of organic antibacterial agents mainly include quaternary ammonium salts, quaternary phosphonium salts, biguanides, and halamines, among which quaternary ammonium salts and halamines are widely used. However, the long-term use of a large number of quaternary ammonium antibacterial agents has caused the problem of secondary pollution of the environment and caused the resistance of bacterial microorganisms. Halamine antibacterial agents are a class of organic compounds containing one or more N-X bonds (X ...

Claims

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Application Information

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IPC IPC(8): C07F7/18D06M13/513D06M101/06
CPCC07F7/1804C07F7/1892D06M13/5135D06M2101/06
Inventor 李令东迟晓芳赵曰彪
Owner DALIAN UNIV OF TECH
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