Perfluoroolefine type anionic gemini surfactant and preparation method thereof

A perfluoroalkene type, gemini surface technology, used in the preparation of sulfonates, chemical instruments and methods, organic chemistry, etc., can solve problems such as insufficient surface activity, improve decontamination and washing ability, excellent dispersibility, reduce The effect of surface tension

Inactive Publication Date: 2014-03-26
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the defect of insufficient surface activity of existing hexafluoropropylene oligomer derivative surfactants, the present invention has prepared a class of gemini-type fluorosurfactants based on perfluorononene and perfluorohexene, whose general formula is

Method used

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  • Perfluoroolefine type anionic gemini surfactant and preparation method thereof
  • Perfluoroolefine type anionic gemini surfactant and preparation method thereof
  • Perfluoroolefine type anionic gemini surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Preparation of intermediate (B) by condensation of perfluorononenyloxybenzoyl chloride and 3-oxa-1,5-pentanediamine

[0017] 11.47g (20.2mmol) of perfluorononenyloxybenzoyl chloride obtained by chlorination of perfluorononenyloxybenzoic acid through thionyl chloride was dissolved in 30mL of acetonitrile, and 3-oxa-1,5-pentane was added dropwise A mixture of 1.04g (10.0mmol) of diamine, 2.07g (20.5mmol) of triethylamine and 30mL of acetonitrile was incubated at 50°C for 8h, the solvent was recovered under reduced pressure, stirred with water, filtered, washed with water, and dried in vacuo to obtain a light yellow solid 11.4 g, yield 94.5%.

Embodiment 2

[0018] Example 2 Preparation of fluorosurfactant by condensation of N,N'-bis(perfluorononenyloxybenzoyl)-3-oxa-1,5-pentanediamine and 1,3-propane sultone

[0019] Take 6.02g (5.0mmol) of the product obtained in Example 1, 1.34g (11.0mmol) of 1,3-propane sultone, 10mL of N,N-dimethylformamide and 20mL of water and mix, add potassium hydroxide to adjust the pH Reaction at 10,60°C for 22h. Cool, filter, wash, and dry in vacuo to obtain 7.1 g of an amber solid product with a yield of 93.4%.

[0020] Infrared spectrum characteristic peak (cm -1 ): 1643 (C=O), 1596 (benzene ring C=C), 1493 (benzene ring C=C), 1243 (S=O), 1235 (aryl-O), 1185 (C-F), 1134 (C-F ), 1129 (S=O), 1040 (S=O), there is no N-H peak around 3330. Elemental Analysis: C 42 h 28 f 34 K 2 N 2 o 11 S 2 Theoretical value C 33.07%, H 1.84%, F 42.39%; measured value C 32.90%, H 1.74%, F 42.18%. Mass spectrum: Molecular weight 1524.

Embodiment 3

[0021] Example 3 Preparation of intermediate (B) by condensation of perfluorohexenyloxybenzoyl chloride and 1,4-butanediamine

[0022] Add dropwise to 8.44g (20.2mmol) of perfluorohexenyloxybenzoyl chloride obtained by chlorination of perfluorohexenyloxybenzoic acid through thionyl chloride, 2.79g (20.2mmol) of anhydrous potassium carbonate and 40mL of tetrahydrofuran The mixed solution of 0.88g (10.0mmol) of 1,4-butanediamine and 30mL of tetrahydrofuran was refluxed for 8h, the solvent was recovered under reduced pressure, stirred with water, filtered, washed with water, and dried in vacuo to obtain 7.9g of light yellow solid with a yield of 88.9%.

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Abstract

The invention discloses a sulfonic acid type anionic gemini surfactant based on perfluorinated nonene and perfluorinated hexane, and a preparation method thereof. According to the preparation method, perfluorinated nonene or perfluorinated hexane is taken as a raw material; perfluorinated alkene oxyl benzoyl chloride is obtained via condensation of the raw material with p-hydroxybenzoic acid, and chlorination; perfluorinated alkene oxyl benzamide is obtained via direct condensation of perfluorinated alkene oxyl benzoyl chloride with diamine without separation; and at last the sulfonic acid type anionic gemini fluorinated surfactant is obtained via condensation of perfluorinated alkene oxyl benzamide with a sulfonated alkylation agent, wherein perfluorinated alkene oxyl phenyl groups are taken as lipophilic groups, amide bonds are taken as conjugation bridges, and sulfonates are taken as hydrophilic groups. The anionic gemini surfactant based on hexafluoropropene trimer or perfluoro(4-methylpent-2-ene) is high in surface activity, simple in synthesis, and low in cost, and possesses a promising application prospect.

Description

technical field [0001] The invention relates to a class of fluorine surfactants, in particular to a class of anionic gemini surfactants containing perfluorononenyloxy or perfluorohexenyloxy, and a preparation method thereof. Background technique [0002] Fluorosurfactants are a special class of surfactants, which have typical three-high amphiphobic (high thermal stability, high chemical stability, high surface activity, both oil-repellent and water-repellent) characteristics, so they are widely used in fire protection, oil extraction, etc. has important applications. The most widely used fluorosurfactants are perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS) and their derivatives, but PFOA and PFOS compounds have large production pollution, non-biodegradable, long-distance migration, etc. Disadvantages are being restricted and disabled. Fluorosurfactants derived from hexafluoropropylene oligomers, especially hexafluoropropylene dimer and hexafluoroprop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/22C07C309/15C07C303/32C09K23/22
Inventor 郑土才吕亮
Owner QUZHOU UNIV
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