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Hydroxy halogen amine compound containing quaternary ammonium salt functional group and preparation method and application thereof

A technology of quaternary ammonium salt function and hydroxyhalamine, which is applied in the synthesis and application of halamine fungicides, and the synthesis and application of quaternary ammonium salted hydroxyhalamine compounds, which can solve the problem of decreased surface hydrophilicity and insufficient antibacterial efficacy. Long-lasting, affecting material softness and wrinkle resistance, etc., to achieve the effect of broad-spectrum bactericidal effect

Inactive Publication Date: 2012-11-21
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the antibacterial materials and products with halamine functional groups prepared by the above patent methods have relatively strong ability to kill harmful microorganisms, their antibacterial efficacy cannot lasting
In addition, the surface of some materials such as cotton fibers may reduce the hydrophilicity of the surface after bonding certain heterocyclic halamine molecules, thus affecting the softness and wrinkle resistance of these materials

Method used

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  • Hydroxy halogen amine compound containing quaternary ammonium salt functional group and preparation method and application thereof
  • Hydroxy halogen amine compound containing quaternary ammonium salt functional group and preparation method and application thereof
  • Hydroxy halogen amine compound containing quaternary ammonium salt functional group and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1 Synthesis of 1-dimethylaminomethyl-5,5-dimethylhydantoin

[0084]

[0085] Add 15.80 g (0.10 mol) of 1-hydroxymethyl-5,5-dimethylhydantoin to a 500 ml round bottom flask filled with 200 ml of isopropanol, stir to dissolve, then add 16.39 g (0.12 mol) A 33% aqueous solution of dimethylamine was stirred and reacted at 30°C for 4 hours, and the solvent was distilled off from the reaction solution under reduced pressure to obtain 17.99 g of crude product, which was obtained by titration with hydrochloric acid to obtain 1-dimethylaminomethyl-5,5- The content of dimethyl hydantoin is 99.86%, and the yield of reaction can be calculated accordingly to be 97.11%. Take 2.00 grams of crude product, add an appropriate amount of anhydrous acetone until it is completely dissolved, and then pass through dry hydrogen chloride gas, there is a large amount of solids, namely 1-dimethylaminomethyl-5,5-dimethylhydantoin The hydrochloride was precipitated, centrifuged, and drie...

Embodiment 2

[0086] Example 2 Synthesis of (2,3-dihydroxypropyl)-(5,5-dimethylhydantoin-1)methyl-dimethylammonium chloride

[0087]

[0088] Add 18.50 g (0.10 mol) of 1-dimethylaminomethyl-5,5-dimethylhydantoin to a 500-ml round-bottomed flask filled with 200 ml of water, heat to dissolve at 55°C and add 9.25 grams (0.10mol) of epichlorohydrin, stirred for 4 hours, measured by silver nitrate titration (2,3-dihydroxypropyl)-(5,5-dimethylhydantoin-1)methyl- The yield of dimethylammonium chloride is about 83.47%. The solvent was distilled off under reduced pressure to obtain 28.61 g of a crude product. Dissolve the crude product in absolute ethanol, add anhydrous acetone to crystallize and purify the product, and centrifuge to separate (2,3-dihydroxypropyl)-(5,5-dimethylhydantoin-1)methyl-dimethyl ammonium chloride solid, and then dried in a vacuum oven. The molecular ion peak M of the quaternary ammonium salt positive ion was obtained by mass spectrometry + : 260.2. IR:3261cm -1 Lef...

Embodiment 3

[0089] The synthesis of embodiment 3 (3-chloro-2-hydroxypropyl)-(5,5-dimethylhydantoin-1) methyl-dimethyl ammonium chloride

[0090]

[0091] Add 18.50 g (0.10 mol) of 1-dimethylaminomethyl-5,5-dimethylhydantoin to a 500-ml round-bottomed flask filled with 200 ml of 0.50 mol / L hydrochloric acid solution and wait for it to dissolve Finally, 9.25 g (0.10 mol) of epichlorohydrin was added, stirred and reacted at room temperature for 6 hours, and the reaction ended when the solution was slightly alkaline. The solvent was distilled off from the reaction solution under reduced pressure to obtain 30.81 g of a crude product. Dissolve the crude product in absolute ethanol, add anhydrous acetone to crystallize and purify the product, and centrifuge to obtain (3-chloro-2-hydroxypropyl)-(5,5-dimethylhydantoin-1)methyl-dimethyl ammonium chloride solid, and then dried in a vacuum oven. Elemental analysis test value: C 11 h 21 0 3 N 3 Cl 2 : N,13.26; C,41.52; H,6.91 (theoretical ca...

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Abstract

The invention relates to the field of organic synthesis and discloses hydroxy halogen amine compound containing quaternary ammonium salt functional group with a structure shown in a formula (I), wherein R1 and R2 are C1-C20 alkyl or alkene groups, C1-C8 haloalkyl or alkenyl halide groups or C1-C8 hydroxy alkyl, or R1 and R2 are combined into C3-C7 naphthene base or cycloalkene group, and R is selected from hydantoins group, 2-imidazole ketone group, 4-imidazole ketone group, isocyanurates group, 1,3,8-tri-azaspiro [4.5] decane-2,4-diketones group, and piperidines group. The compound can be used for preparing an antibacterial agent and an antibacterial material.

Description

technical field [0001] The invention relates to the field of organic synthesis, and relates to the synthesis and application of a novel high-efficiency quaternized ammonium halide fungicide. It specifically relates to the synthesis and application of a class of quaternized ammonium-salted hydroxyhalamine compounds for antibacterial coating, polymerization and grafting. Background technique [0002] With the gradual improvement of people's living standards, people pay more and more attention to the environment and their own health. Clothing, sanitary products, daily necessities, food packaging, etc. with antibacterial function have attracted more and more attention because they can effectively control or eliminate the growth and reproduction of harmful microorganisms. At the same time, the proper use of antibacterial products in public places, especially hospitals, can effectively prevent the spread and infection of bacteria and viruses. Therefore, the research and developm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/72A01N43/50A01P1/00C09D5/14D06M13/463D06M101/06
Inventor 梁杰亢真真焦玉超张冰
Owner SHANGHAI NORMAL UNIVERSITY
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