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Dihydroxy-containing tetra quaternary phosphonium cation antibacterial agent and preparation method thereof

A phosphonium cation, dihydroxyl technology is applied in the field of four-season phosphonium cation antibacterial agent and its preparation, which can solve the problems of limited use range, no research on four-season phosphonium salt, and reduced quaternary phosphonium salt grafting rate, etc., and achieves high-efficiency and broad-spectrum antibacterial properties , long-lasting antibacterial effect

Active Publication Date: 2017-11-17
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of quaternary phosphonium salt has a double bond in its molecule, so it can only rely on the double bond to polymerize and graft in the material. This method is easy to reduce the grafting rate of the quaternary phosphonium salt. In addition, the double bond is easy to polymerize under high temperature conditions, so this type of Antibacterial agents cannot participate in high-temperature reactions, which limits the scope of use
[0006] The above documents or patents all graft quaternary phosphonium salts into the material through chemical bonds at one end, and do not involve research on quaternary phosphonium salts that can be embedded at both ends, and there is no research on quaternary phosphonium salts

Method used

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  • Dihydroxy-containing tetra quaternary phosphonium cation antibacterial agent and preparation method thereof
  • Dihydroxy-containing tetra quaternary phosphonium cation antibacterial agent and preparation method thereof
  • Dihydroxy-containing tetra quaternary phosphonium cation antibacterial agent and preparation method thereof

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Embodiment 1

[0036] First synthesize compound B1: Take 1,6-bis(diphenylphosphine)hexane (1.14g, 2.5mmol), p-bromophenol (2.16g, 12.5mmol), 5mL of ethylene glycol and 50mg of nickel bromide into 50mL In a three-neck flask, nitrogen gas was introduced, and the temperature was raised to 180° C. under reflux. After 4 hours of magnetic stirring reaction, the system was left to stand, and after cooling, all the reactants were dissolved in 20 mL of dichloromethane, and the organic layer was washed three times with deionized water. anhydrous Na 2 SO 4 The solution was dried and filtered, and the organic phase was washed with a large amount of diethyl ether and a large amount of tetrahydrofuran, respectively, to obtain compound B1.

[0037] Take compound A1 (0.4g, 1.64mmol), and compound B1 (2.3g, 3.61mmol), potassium carbonate (1.0g, 7.24mmol), DMF 20mL were added to a 100mL single-necked flask, magnetically stirred at reflux at 50°C 8h. Cool to room temperature after the reaction is complete....

Embodiment 2

[0039]Take compound A2 (0.5g, 1.64mmol), add compound B1 (2.3g, 3.61mmol), sodium carbonate (0.7g, 7.24mmol), and DMF 20mL into a 100mL single-necked flask, and magnetically stir and reflux at 50°C 8h. Cool to room temperature after the reaction is complete. All reactants were then dissolved in 20 mL of dichloromethane. The organic layer was washed three times with deionized water, followed by anhydrous Na 2 SO 4 The solution was dried and filtered, and the organic phase was washed with a large amount of tetrahydrofuran to obtain the target compound as a white powder.

Embodiment 3

[0041] Take compound A3 (0.35g, 1.64mmol), add compound B1 (2.3g, 3.61mmol), potassium carbonate (1.0g, 7.24mmol), and dichloromethane 20mL into a 100mL single-necked flask, and magnetically Stir for 24h. Cool to room temperature after the reaction is complete. All reactants were then dissolved in 20 mL of dichloromethane. The organic layer was washed three times with deionized water, followed by anhydrous Na 2 SO 4 The solution was dried and filtered, and the organic phase was washed with a large amount of tetrahydrofuran to obtain the target product in the form of white powder.

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Abstract

The invention relates to a dihydroxy-containing tetra quaternary phosphonium cation antibacterial agent and a preparation method thereof, and belongs to the technical field of quaternary phosphonium salt compounds. The structure of the antibacterial agent is [HO-R-P<+>(Ph)2-(CH2)x-P<+>(Ph)2-R-O-Q-O-R'-P<+>(Ph)2-(CH2)y-P<+>(Ph)2-R'-OH].4X<->, wherein R and R' are selected from C4-C10 alkoxyphenyl and phenyl, x and y are respectively an integer of 4-10, Q is -(CH2)z- or -C2H4-(O-C2H4)m-, z is an integer of 4-10, m is an integer of 1-5, and X is a halogen compound. According to the present invention, the hydroxy can be embedded in the material main chain through the reaction of the hydroxy and other compounds so as to achieve the modification on the material, such that the application range of the antibacterial agent is expanded while the potential overflow possibility is solved, the antibacterial lasting time is long, and the antibacterial effect cannot be affected by the temperature during the reaction process.

Description

technical field [0001] The invention discloses a tetraquaternary phosphonium cationic antibacterial agent containing dihydroxyl groups and a preparation method thereof, belonging to the technical field of quaternary phosphonium salt compounds. Background technique [0002] In the field of antibacterial agents, quaternary phosphonium salts (QPS), as a new generation of antibacterial agents, exhibit high efficiency and broad-spectrum activity against pathogenic bacteria and fungi, and even their killing activity extends to enveloped viruses and parasites, In addition, quaternary phosphonium salts also have the advantages of higher thermal stability and pH stability (Materials Science and Engineering C 2016,61:79-84). [0003] CN200810023393.2 discloses a water-insoluble quaternary phosphonium salt fungicide, which is prepared by using silica gel-based inorganic materials as carriers and grafting aliphatic or aromatic monoquaternary phosphonium salt functional groups on the sur...

Claims

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Application Information

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IPC IPC(8): A01N57/34C07F9/54C08G18/38C09D175/08A01P1/00A01P3/00
CPCA01N57/34C07F9/5442C08G18/388C09D175/08
Inventor 汪中明杨茜韩克飞朱红
Owner BEIJING UNIV OF CHEM TECH
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