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Photoresponsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and synthesis method thereof

A technology of surfactant and worm-like micelle is applied to light-responsive quaternary ammonium salt cationic surfactants. The synthesis field of the surfactant can solve the problems of few reports of worm-like micelles, and achieve good light quality. Responsiveness and bactericidal properties, mild synthesis conditions, and simple product purification methods

Active Publication Date: 2018-12-07
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] For the research on light-responsive worm-like micelles at home and abroad, the system is mostly composed of two parts: the traditional surfactant part that can form worm-like micelles and the photo-responsive organic acid or salt, while for a single photo-responsive surface There are few reports on worm-like micelles composed of active agents

Method used

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  • Photoresponsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and synthesis method thereof
  • Photoresponsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and synthesis method thereof
  • Photoresponsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of light-responsive quaternary ammonium salt cationic surfactants with the following structural formula

[0039]

[0040] 1. Synthesis of p-hydroxybenzoic alcohol

[0041] Dissolve 0.450g (12mmol) of sodium borohydride in 20mL of ethanol, then add the resulting solution dropwise to 1.300g (6mmol) of p-hydroxyazobenzaldehyde, stir at room temperature until no bubbles emerge, and reflux at 40°C for 12 hours. After the reaction, add 10 mL of deionized water at room temperature, stir for 10 minutes to quench the reaction, then adjust the pH to neutral with dilute hydrochloric acid, filter and dry the filter cake after stirring for 10 minutes, and the obtained shiny brown solid is p-Hydroxyazobenzyl alcohol, its yield is 91.1%.

[0042] 2. Synthesis of 4′-bromoethoxyazobenzyl alcohol

[0043] Dissolve 0.456g (2mmol) p-hydroxyazobenzyl alcohol and 0.320g (8mmol) NaOH into 8mL distilled water, then add 20mL absolute ethanol, and add the resulting mixture dropwis...

Embodiment 2

[0048] Synthesis of light-responsive quaternary ammonium salt cationic surfactants with the following structural formula

[0049]

[0050] In Example 1, N,N-dimethyl n-octylamine was replaced with equimolar N,N-dimethyldodecylamine, other steps were the same as in Example 1, and the shiny yellow solid obtained was The photoresponsive quaternary ammonium salt cationic surfactant has a yield of 72.4%.

[0051] The resulting light-responsive quaternary ammonium salt cationic surfactant was characterized by mass spectrometer and nuclear magnetic resonance spectrometer, the results are shown in Figure 7 and Figure 8 . The relative molecular weight of the compound is 548, and its mass spectrum molecular ion peak should be M + ,Depend on Figure 7 It can be seen that the molecular isotope ion peak of the synthesized compound is 469.36, and the corresponding ion peak is M + +1; Figure 8 In , each hydrogen in the compound has a one-to-one correspondence with the chemical sh...

Embodiment 3

[0053] Synthesis of light-responsive quaternary ammonium salt cationic surfactants with the following structural formula

[0054]

[0055] In Example 1, N,N-dimethyl n-octylamine was replaced with equimolar N,N-dimethylhexadecylamine, other steps were the same as in Example 1, and the shiny yellow solid obtained was The photoresponsive quaternary ammonium salt cationic surfactant has a yield of 64.2%.

[0056] The resulting light-responsive quaternary ammonium salt cationic surfactant was characterized by mass spectrometer and nuclear magnetic resonance spectrometer, the results are shown in Figure 11 and Figure 12 . The relative molecular weight of the compound is 604, and its mass spectrum molecular ion peak should be M + ,Depend on Figure 11 It can be seen that the molecular isotope ion peak of the synthesized compound is 525.42, and the corresponding ion peak is M + +1; Figure 12 In , each hydrogen in the compound has a one-to-one correspondence with the chemi...

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Abstract

The invention discloses a light-responsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and a synthesis method thereof. Azobenzaldehyde, 1,2-dibromoethane, and N,N-dimethylalkylamine are used as raw materials, and prepared by reduction reaction, Williamson ether formation reaction, and quaternization reaction. The synthesis method of the invention is simple to operate, the raw materials are cheap and easy to obtain, the synthesized surfactant has high purity and a yield higher than 64.0%, its aqueous solution has good photoresponsiveness and low surface tension, and the critical micelle concentration is lower than 4.0 ×10‑4mol / L, and can form worm-like micelles.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and fine chemical industry, and specifically relates to a light-responsive quaternary ammonium salt cationic surfactant capable of forming worm-like micelles and containing azophenyl groups, and a method for synthesizing the surfactant. Background technique [0002] In recent years, more and more synthesis and properties of responsive surfactants have been studied and applied. In many environmental stimulation conditions, such as: light, pH value, temperature, ionic strength, electric field, magnetic field, solvent, etc., due to the advantages of light (visible light, ultraviolet light, infrared light) being easy to obtain, easy to carry and operate, etc. researchers concerned. Usually, there are many groups that are photoresponsive, such as azophenyl group, stilbene group, spiropyran group, etc., introducing specific photoresponsive groups into surfactant molecules or When a light-res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08B01F17/18C09K23/18
CPCC07C245/08C09K23/00
Inventor 陈亚芍员乐张晶张峰
Owner SHAANXI NORMAL UNIV
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