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Dihydroxyl quaternary ammonium salt with antimicrobial activity as well as preparation method and application thereof

A technology of dihydroxyquaternary ammonium salt and antibacterial activity, which is applied in the field of antibacterial materials and its preparation, bishydroxyquaternary ammonium salt and its preparation, can solve the problems of antibacterial power decline, etc., and achieve fast reaction time, high yield and low cost Effect

Inactive Publication Date: 2014-04-09
BINZHOU MEDICAL COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The length of the alkyl chain has a great influence on the antibacterial ability. With the increase of the alkyl chain, the antibacterial ability is enhanced; but after a certain length, the antibacterial ability will decrease [7,8]

Method used

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  • Dihydroxyl quaternary ammonium salt with antimicrobial activity as well as preparation method and application thereof
  • Dihydroxyl quaternary ammonium salt with antimicrobial activity as well as preparation method and application thereof
  • Dihydroxyl quaternary ammonium salt with antimicrobial activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of BNQAS

[0027] Dissolve N-methyldiethanolamine (1.19g, 10mmol) in 4mL N,N-dimethylformamide, slowly add benzyl chloride (1.71g, 10mmol) dropwise, and control the reaction temperature at 60°C for 6 hours. Determine the reaction end point by layer analysis (TLC), cool down, add 10ml of anhydrous ether as a precipitant, place in a -20°C refrigerator for 4 hours to obtain a white solid, filter it with suction, and recrystallize the crude product twice with 4ml of absolute ethanol and 30ml of ether 2.7 g of N-methyl-N-benzyl-N,N-dihydroxyethylammonium chloride (BNQAS) was obtained, with a yield of 93%. IR(KBr pellet cm -1 ):3346(br),3045(m),2985(s),2889(m),1618(br),1498(m),1471(s),1384(s),1076(s),906(s ), 760(s), 711(s). 1 H NMR(400MHz,DMSO)δ3.02(s,3H,N-CH 3 ),3.34-3.40(m,2H,N-CH 2 ),3.51-3.56(m, 2H,N-CH 2 ),3.91-3.92(d,4H,2O-CH 2 ),4.71(s,2H,CH 2 ),5.53-5.51(s,2H,2OH),7.51-7.65(m,5H,C 6 h 5 ).Anal.Calcd.for C 12 h 20 NO 2 Br: C49....

Embodiment 2

[0028] Example 2: Synthesis of C12QAS

[0029] Dissolve N-methyldiethanolamine (1.19g, 10mmol) in 4mL N,N-dimethylacetamide, slowly add dodecyl bromide (2.49g, 10mmol) dropwise, and control the reaction temperature at 80°C for 6 hours , determined the end point of the reaction by thin layer analysis (TLC), cooled, added 10ml of anhydrous acetone as a precipitant, and placed it in a -20°C refrigerator for 4 hours to obtain a white solid, filtered it with suction, and weighed the crude product with 5ml of absolute ethanol and 30ml of acetone. Crystallize twice to obtain 3.4 g of N-methyl-N-dodecyl-N,N-dihydroxyethylammonium bromide (C12QAS), with a yield of 92%. IR(KBr pellet cm -1 ):3293(s), 2921(s), 2852(s), 2856(m), 1618(br), 1467(s), 1380(m), 1057(s), 722(s). 1 H NMR (400MHz, DMSO) δ0.84-0.87 (m, 3H, C-CH 3 ),1.25(m,18H,9CH 2 ),1.64-1.71(m,2H,CH 2 ),3.07(s,3H,N-CH 3 ),3.33-3.37(m,2H,N-CH2 ),3.39-3.47(m,4H,2N-CH 2 ),3.81-3.82(m,4H,2O-CH 2 ),5.23-5.26(m,2H,2OH).Anal.Ca...

Embodiment 3

[0030] Example 3: Synthesis of C14QAS

[0031] Dissolve N-acetyldiethanolamine (1.19g, 10mmol) in 5mL of ethanol, slowly add dodecyl bromide (2.77g, 10mmol) dropwise, and control the reaction temperature at 80°C for 8 hours. Through thin layer analysis (TLC ) to determine the end point of the reaction, cool down, add 10ml of anhydrous petroleum ether as a precipitant, place it in a -20°C refrigerator for 4 hours to obtain a white solid, filter it with suction, recrystallize the crude product twice with 5ml of absolute ethanol and 30ml of petroleum ether to obtain N -Acetyl-N-tetradecyl-N,N-dihydroxyethylammonium bromide (C14QAS) product 3.2g, yield 82%. IR(KBr pellet cm -1 ):3289(s), 2920(s), 2847(s), 1618(br), 1467(s), 1377(s), 1047(s), 723(s). 1 H NMR(400MHz,DMSO):δ0.84-0.87(m,3H,C-CH 3 ),1.24-1.27(m,22H,11CH 2 ),1.66-1.67(m,2H,CH 2 ),3.09(s,3H,N-CH 3 ),3.35-3.41(m,2H,N-CH 2 ),3.44-3.45(m,4H,2N-CH 2 ),3.81-3.82(m,4H,2O-CH 2 ),5.23-5.26(m,2H,2OH).Anal.Calcd.for C 19...

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Abstract

The invention relates to dihydroxyl quaternary ammonium salt with antimicrobial activity as well as a preparation method and application of the dihydroxyl quaternary ammonium salt, belonging to the field of antibacterial materials and preparation methods. The preparation method comprises steps of carrying out reaction on N-R1-diethanol amine and halogenated hydrocarbon (R2-X) in an organic solvent, after precipitation of the precipitator, recrystallizing repeatedly so as to obtain the dihydroxyl quaternary ammonium salt (N-R1-N-R2-N,N-diethoxy ammonium halide). The quaternary ammonium salt is simple to synthesize, has high yield and low cost, has high reaction speed and simple and convenient purification method. The dihydroxyl quaternary ammonium salt has good capacity in resisting both various bacteria such as escherichia coli and various funguses such as physalospora piricala, and has good application prospect.

Description

technical field [0001] The invention relates to a class of dihydroxy quaternary ammonium salts with antibacterial activity and a preparation method and application thereof, belonging to the technical field of antibacterial materials and preparation methods thereof. Background technique [0002] Quaternary ammonium salt (QAS, also known as quaternary ammonium salt) refers to a type of organic ammonium salt compound formed by replacing four hydrogen atoms in ammonium ions with hydrocarbon groups. The general formula R 4 N + x - , where the four hydrocarbon groups R can be the same or different, and X is mostly a halogen anion (F-, Cl - 、Br - , I - ), can also be the acid radical (HSO 4 - 、RCOO - Wait) [1] . The properties of quaternary ammonium salts are similar to those of inorganic ammonium salts. They are easily soluble in water, the aqueous solution is conductive, and have the characteristics of high efficiency, low toxicity, strong bactericidal ability, strong sl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/40C07C213/02C07C233/89C07C231/08C07C323/25C07C319/20A01P1/00A01P3/00
Inventor 王春华侯桂革孙居锋刘文帅
Owner BINZHOU MEDICAL COLLEGE
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