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Degradable gemini quaternary ammonium salt bactericide and preparation method thereof

A technology of geminiquaternary ammonium salts and fungicides, which is applied in the field of preparation of geminiquaternary ammonium salt fungicides, can solve the problems of no literature reports on geminiquaternary ammonium salts, no ability to kill fungi, and slow degradation of quaternary ammonium salts. High yield, strong bactericidal effect, strong adsorption and bactericidal effect

Inactive Publication Date: 2016-04-20
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are some problems in long-term use of traditional quaternary ammonium salt fungicides: (1) drug resistance; (2) unbalanced sterilization, the ability of traditional single-chain quaternary ammonium salts represented by benzalkonium chloride to kill Gram-positive bacteria Stronger than Gram-negative bacteria, it has almost no ability to kill fungi; (3) Secondary pollution, due to drug resistance, the amount of quaternary ammonium fungicides is increasing, and traditional quaternary ammonium salts degrade slowly in the environment , making it pollute the environment to a certain extent
The preparation method of the degradable gemini quaternary ammonium salt applied for by the present invention has no bibliographical information at present

Method used

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  • Degradable gemini quaternary ammonium salt bactericide and preparation method thereof
  • Degradable gemini quaternary ammonium salt bactericide and preparation method thereof
  • Degradable gemini quaternary ammonium salt bactericide and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 1. Preparation of benzyl N,N-dimethylglycine: Weigh 10.12g (100mmol) of N,N-dimethylglycine, 12.98g benzyl alcohol (120mmol), 23.01g EDCI (120mmol) and 1.22g DMAP (10mmol) Place in 250mL containing 50mL, and react at room temperature for 24h. After the reaction, add an appropriate amount of saturated saline, extract with CH2Cl2, combine the organic phases, remove the solvent by rotary evaporation and then distill to obtain 13.53g of N,N-dimethylglycine benzyl ester ( 70%). Its NMR spectrum is attached figure 1 ;

[0024] 2. Preparation of N,N-dimethylglycine benzyl ester hydrochloride: Dissolve 6.76g (35mmol) N,N-dimethylglycine benzyl ester in 30mL ethanol solution, and add dry hydrogen chloride gas under stirring , until the precipitate was completely separated out, cooled, vacuum filtered, and dried to obtain 10.17g of N,N-dimethylglycine benzyl ester hydrochloride;

[0025] 3. Preparation of Gemini quaternary ammonium salt: 6.76g N,N-dimethylglycine benzyl ester,...

Embodiment 2

[0027] 1. Preparation of N,N-dimethylglycine octyl ester: Weigh 10.12g (100mmol) of N,N-dimethylglycine, 15.63g n-octanol (120mmol), 24.74gDCC (120mmol) and 1.22gDMAP (10mmol) ) was placed in 250mL containing 50mL, and reacted at room temperature for 24h. After the reaction, the insoluble matter was removed by filtration, washed with CH2Cl2, the organic phase was combined, the solvent was removed by rotary evaporation and then distilled to obtain 15.50g N,N-dimethylglycine n-octyl ester (72%);

[0028] 2. Preparation of N,N-dimethylglycine n-octyl hydrochloride: take 7.75g (36mmol) N,N-dimethylglycine n-octyl ester and dissolve it in 30mL ethanol solution, and pass it into the dry Hydrogen chloride gas until the precipitate is completely separated out, cooled, vacuum filtered, and dried to obtain 11.35g N,N-dimethylglycine n-octyl hydrochloride;

[0029] 3. the preparation of gemini quaternary ammonium salt: with above-mentioned prepared 7.75gN, N-dimethylglycine n-octyl este...

Embodiment 3

[0031] 1. Preparation of N,N-dimethylglycine decyl ester: Weigh 10.12g (100mmol) of N,N-dimethylglycine, 18.99g of n-decyl alcohol (120mmol), 23.01g of EDCI (120mmol) and 16.28g of HOBT (120mmol) ) was placed in 250mL containing 50mL, and reacted at room temperature for 24h. After the reaction was completed, it was washed with saturated brine, then extracted with CH2Cl2, the organic phases were combined, the solvent was removed by rotary evaporation and then distilled to obtain 16.55g of N,N-dimethylglycine decyl ester ( 68%);

[0032] 2. Preparation of N,N-dimethylglycine n-decyl ester hydrochloride: Dissolve 8.28g (39mmol) N,N-dimethylglycine n-decyl ester in 30mL ethanol solution, and pass it into dry Hydrogen chloride gas, until the precipitate is completely separated out, cooled, vacuum filtered, and dried to obtain 12.18g N,N-dimethylglycine n-decyl ester hydrochloride;

[0033]3. Preparation of Gemini quaternary ammonium salt: 8.28g N, N-dimethylglycine n-decyl ester, ...

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Abstract

The invention discloses a degradable gemini quaternary ammonium salt bactericide and a preparation method thereof. The method comprises steps as follows: Step one, N,N-dimethyl glycine, long-chain fatty alcohol (carbon atom numbers are 8, 10, 12, 14, 16 and 18) and benzyl alcohol have an esterification reaction in the presence of a coupling reagent to produce corresponding N,N-dimethyl glycine ester; Step two, the obtained N,N-dimethyl glycine ester and hydrogen chloride, hydrogen bromide or hydrogen iodide react to produce corresponding salt; Step three, products obtained in previous two steps and epichlorohydrin are subjected to quaternization, and degradable gemini quaternary ammonium salt is obtained. The gemini quaternary ammonium salt is more beneficial to adsorption of bacterium surfaces by bactericide molecules due to the electrostatic interaction of two quaternary nitrogen ions contained in molecules and the induction of carbonyl groups in ester groups, so that bacteria are broken through change of permeability of cell walls; hydrophilic groups and hydrophobic groups extend into lipoid layers and protein layers of bacterium cells more conveniently to cause protein denaturation and enzyme deactivation. The bactericide has higher bactericidal ability under the synergistic effect. The gemini quaternary ammonium salt bactericide is efficient, low in toxicity, easily degradable and environment-friendly.

Description

technical field [0001] The invention relates to the field of environment-friendly bactericidal disinfectants, in particular to the preparation of a degradable gemini quaternary ammonium salt bactericide. Background technique [0002] Quaternary ammonium salt is not only a commonly used cationic surfactant, but also a good bactericide and disinfectant. It not only has strong bactericidal ability, quick effect, but also has little irritation to skin and is non-corrosive to metal and rubber. Therefore, it is widely used in (agricultural fungicides, sterilization and disinfection of public places (hospitals, swimming pools), circulating water sterilization and algicides, aquaculture sterilization and disinfection agents, sterilization and disinfection agents for medical equipment, livestock and poultry house disinfectants, red tide killing agent, blue-green algae killer, etc.) and other fields of sterilization and disinfection. There are some problems in long-term use of tradit...

Claims

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Application Information

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IPC IPC(8): C07C229/16C07C227/18A01N37/44A01P3/00
CPCA01N37/44C07C227/18C07C229/16C07C229/12
Inventor 林炜张卫辉王春华穆畅道
Owner SICHUAN UNIV
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