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Tri-hydroxy containing hexaquaternary phosphonium cation antibacterial agent and preparation method thereof

A technology of trihydroxyl and antibacterial agents, applied in chemical instruments and methods, disinfectants, organic chemistry, etc., can solve the problems that do not involve trihydroxyhexaquaternary phosphonium salt antibacterial agents, and achieve enhanced electrostatic interaction and high unit positive charge , to avoid the effect of loss

Active Publication Date: 2019-06-28
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above documents or patents do not relate to the research on antibacterial agents containing trihydroxy hexaquaternary phosphonium salts

Method used

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  • Tri-hydroxy containing hexaquaternary phosphonium cation antibacterial agent and preparation method thereof
  • Tri-hydroxy containing hexaquaternary phosphonium cation antibacterial agent and preparation method thereof
  • Tri-hydroxy containing hexaquaternary phosphonium cation antibacterial agent and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 8mmol of compound A and 2mmol of B were added to a 100mL three-necked flask, 30mL of methanol was added thereto, and 8mmol of NaOH was added. Reflux at 60°C and monitor the progress of the reaction by TLC spot plate. After the reaction is complete, cool to room temperature, remove solvent methanol by rotary evaporation, dissolve the crude product in dichloromethane, wash with deionized water, dry with anhydrous sodium sulfate, and remove dichloromethane by rotary evaporation. A pale yellow crude product was obtained. Further purification was carried out with a chromatographic column (petroleum ether and ethyl acetate).

[0033] Dissolve the purified product in dichloromethane, and then dropwise add 3mol L -1 HCl solution, monitor the progress of the reaction by TLC spot plate, after the reaction is complete, the organic phase is washed with deionized water, and the pH is adjusted until the solution is neutral. The dichloromethane was removed by rotary evaporation, an...

Embodiment 2

[0035] Add 8mmol of compound A and 2mmol of C to a 100mL three-necked flask, add 30mL of methanol, and then add 8mmol of NaOH. Reflux at 60°C and monitor the progress of the reaction by TLC spot plate. After the reaction is complete, cool to room temperature, remove solvent methanol by rotary evaporation, dissolve the crude product in dichloromethane, wash with deionized water, dry with anhydrous sodium sulfate, and remove dichloromethane by rotary evaporation. A pale yellow crude product was obtained. Further purification was carried out with a chromatographic column (petroleum ether and ethyl acetate).

[0036] Dissolve the purified product in dichloromethane, and then dropwise add 3mol L -1 HCl solution, monitor the progress of the reaction by TLC spot plate, after the reaction is complete, the organic phase is washed with deionized water, and the pH is adjusted until the solution is neutral. The dichloromethane was removed by rotary evaporation, and the light yellow pro...

Embodiment 3

[0038]The trihydroxy hexaquaternary phosphonium salt (1wt%) obtained in Example 1, isophorone diisocyanate (1.04g) was added in a 50mL three-necked flask, and then mechanically stirred for 30 minutes at 50°C, and then 50mg was added to the bottle The catalyst is dibutyltin dilaurate, and then polyether polyol HSH330N is added dropwise at 65°C, and the stirring reaction is continued for 1 hour, then the stirring is stopped and cooled. After the system was cooled down to 45°C, 2-hydroxyethyl acrylate (HEA) was added dropwise into the system with a constant pressure dropping funnel to block the -NCO in the system. After reacting for 3 hours, the urethane acrylate / hexaquaternary phosphonium salt-1wt% oligomer was obtained.

[0039] Prepared urethane acrylate / hexaquaternary phosphonium salt-1wt% oligomer with reactive diluent (1,6-hexanediol diacrylate trimethylolpropane triacrylate, isobornyl acrylate) and photoinitiator 2 -Hydroxy-2-methyl-1-phenyl-1-propanone was added to a bea...

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Abstract

The invention relates to a tri-hydroxy containing hexaquaternary phosphonium cation antibacterial agent and a preparation method thereof and belongs to the technical field of quaternary phosphonate compounds. The structure of the antibacterial agent is as shown as follows, wherein a is a unsubstituted C1-8 fatty group, b is a C1-10 fatty group, and X is a halogen family compound and is selected from Cl, Br and I. The antibacterial unit of the antibacterial agent has a high unit positive charge amount to enhance the electrostatic interaction with a bacterial plasma membrane, so that the excellent antibacterial performance is shown. According to the tri-hydroxy hexaquaternary phosphonium, a material is functionally modified by embedding chemical bonds into a main chain of the material aftera phenolic hydroxyl group is reacted with other compounds, so that the problem of loss of a small molecular antibacterial agent can be avoided, and the application range of the antibacterial agent isexpanded.

Description

technical field [0001] The invention discloses a hexaquaternary phosphonium cationic antibacterial agent containing trihydroxy and a preparation method thereof, belonging to the technical field of quaternary phosphonium salt compounds. Background technique [0002] In the field of organic antibacterial agents, quaternary phosphonium salts (QPS) have become a new generation of antibacterial agents due to their high-efficiency and broad-spectrum antibacterial properties against pathogenic bacteria and fungi. It is mainly because the quaternary phosphonium cations and the bacterial cell membrane destroy the bacterial cell plasma membrane through electrostatic interaction, resulting in the leakage of bacterial components, leading to bacterial lysis or death (Biomimetic antimicrobial polymers: recent advances in molecular design[J]. Polymer Chemistry, 2018, 9(18 ):2407-2427). At the same time, when the antibacterial units are the same, the charge per unit area is positively corr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54A01P1/00C08G18/66C08G18/48C08G18/32
Inventor 汪中明汪涛韩克飞朱红
Owner BEIJING UNIV OF CHEM TECH
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