Gemini-type ampholytic surfactant based on perfluoroolefine and preparation method thereof

A surfactant, perfluoroolefin technology, applied in the preparation of sulfonic acid amides, chemical instruments and methods, organic chemistry, etc., can solve the problems of insufficient surface activity of surfactants, achieve excellent dispersibility, reduce surface tension, high The effect of surface activity

Inactive Publication Date: 2015-06-17
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the defects of insufficient surface activity of existing hexafluoropropylene oligomer derivatives surfactants, the present invention prepares a surfactant based on perfluorononene (hexafluoropropylene trimer) and perfluorohexene (hexafluoropropylene Dimer) Gemini amphoteric surfactant, the general formula is

Method used

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  • Gemini-type ampholytic surfactant based on perfluoroolefine and preparation method thereof
  • Gemini-type ampholytic surfactant based on perfluoroolefine and preparation method thereof
  • Gemini-type ampholytic surfactant based on perfluoroolefine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Preparation of N-(3-dimethylaminopropyl) perfluorononenyloxybenzenesulfonamide (A)

[0022] Add 62.3 g (0.1 mol) of perfluorononenyloxybenzenesulfonyl chloride, 10.2 g (0.1 mol) of 3-dimethylaminopropylamine and 100 mL of tetrahydrofuran into a four-necked flask, and dropwise add 20.2 g of triethylamine ( 0.2mol), about 40min to drop, react at 60°C for 5h, pour the reaction solution into water, separate the organic phase, extract three times with tetrahydrofuran, combine the organic phases, and precipitate to obtain a light yellow solid with a yield of 94.6%.

Embodiment 2

[0023] Example 2 Preparation of bis-quaternary ammonium salt intermediate (B) based on perfluorononenyloxy

[0024] Take 34.4g (0.05mol) of the product obtained in Example 1 and 80mL of toluene and heat it to reflux, add dropwise 3.2g (0.025mol) of 1,3-dichloroacetone and 20mL of toluene solution under stirring, reflux for 10 h, and cool to room temperature. Filter, wash with toluene, and dry in vacuo to obtain a white solid with a yield of 92.2%.

Embodiment 3

[0025] Example 3 Preparation of amphoteric gemini surfactant (C) based on perfluorononene

[0026] 75.2g (0.05mol) of the product obtained in Example 2 and 120mL of N,N-dimethylformamide were heated to 80°C, and 25.3g (0.12mol) of sodium bromoethanesulfonate, 4.8g (0.12mol) of sodium bromoethanesulfonate and 4.8g (0.12mol) of A solution of sodium hydroxide and 50 mL of water was incubated for 14 hours, cooled to room temperature, diluted with water, filtered, washed with water and methanol successively, and vacuum-dried to obtain an off-white solid with a yield of 94.9%.

[0027] Infrared spectrum characteristic peak (cm -1 ): 1600 (benzene ring C=C), 1495 (benzene ring C=C), 1245 (S=O), 1232 (aryl-O), 1184 (C-F), 1135 (C-F), 1130 (S=O ), 1040 (S=O), there is no N-H peak around 3330. Elemental Analysis: C 47 h 44 f 34 N 4 o 13 S 4 Theoretical value C 34.26%, H 2.67%, F 39.25%; measured value C 34.18%, H 2.55%, F 39.04%. Mass spectrum: Molecular weight 1646.

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Abstract

The invention discloses a Gemini-type ampholytic surfactant based on perfluorononene and perfluorohexene, and a preparation method thereof. The preparation method comprises the following steps: taking perfluorononene and perfluorohexene as the raw materials, carrying out phenol condensation reactions and chlorosulfonation reactions so as to obtain perfluoroolefineoxyl benzene sulfonyl chloride, then subjecting the perfluoroolefineoxyl benzene sulfonyl chloride to carry out condensation reactions with 2-dimethylamino ethylamine or 3-dimethylamino propylanmine so as to obtain perfluoroolefineoxyl benzene sulfonamide whose amine part comprises a tertiary amine group, then subjecting the perfluoroolefineoxyl benzene sulfonamide to carry out condensation reactions with 1,2-dihaloethane, 1,3-dihalopropane, 1,4-dihalobutane, 1,5-dihalopentane, 3-oxa-1,5-dihalopentane, or 1,3-dihaloacetone, wherein the halogen element is chlorine or bromine, and finally subjecting the reaction product to carry out condensation reactions with vinyl sulfonate, chloroethyl sulfonate, bromoethyl sulfonate or 1,3-propanesultone so as to obtain the Gemini-type ampholytic fluorine surfactant with excellent surface activity and low critical micelle concentration. The Gemini-type ampholytic fluorine surfactant has the prominent characteristics of simple synthetic operation, low cost, high surface activity, and low using concentration, and has a vast market prospect.

Description

technical field [0001] The invention relates to a class of fluorosurfactants, in particular to a class of perfluoroolefin-based gemini-type amphoteric surfactants, and a preparation method thereof. Background technique [0002] Surfactant is an important fine chemical product, which has multiple functions such as wetting, emulsifying, foaming, defoaming, and dispersing, and is known as industrial monosodium glutamate. Surfactants are generally classified into anionic, cationic, amphoteric and nonionic. [0003] Commonly used surfactants, whose hydrophobic groups are hydrocarbon groups, are likely to contain other elements such as oxygen, sulfur, nitrogen, chlorine, bromine, etc. in the molecule. Such commonly used surfactants are called ordinary surfactants. Surfactants containing fluorine, phosphorus, silicon, boron and other elements in the surfactant molecule are called special surfactants. [0004] Fluorosurfactant is a special kind of surfactant. It has high thermal s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/29C07C303/40B01F17/26C09K23/26
Inventor 郑土才赵颖俊郑启富吾国强
Owner QUZHOU UNIV
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