Sulfonic acid dimeric surfactant based on perfluoroolefine and preparation method thereof

A gemini surface, 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 fluorosurfactants, achieve high decontamination and washing ability, reduce surface Tension, good dispersion effect

Active Publication Date: 2013-01-16
江苏中丽新材料有限公司
View PDF8 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the defects of insufficient surface activity of existing hexafluoropropylene oligomer-derived fluorosurfactants, according to the principle and design method of gemini surfactants, the present invention has prepared a class of perfluorononene (hexafluoropropylene trimer body) and perfluorohexene (hexafluoropropylene dimer), a new type of gemini fluorosurfactant, the general formula is

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Sulfonic acid dimeric surfactant based on perfluoroolefine and preparation method thereof
  • Sulfonic acid dimeric surfactant based on perfluoroolefine and preparation method thereof
  • Sulfonic acid dimeric surfactant based on perfluoroolefine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Condensation of perfluorononenyloxybenzenesulfonyl chloride and ethylenediamine

[0028] A solution of 12.60g (20.2mmol) of perfluorononenyloxybenzenesulfonyl chloride in 20mL of N,N-dimethylformamide was slowly added dropwise to 0.60g (10.0mmol) of ethylenediamine and sodium hydroxide at 45°C In a mixture of 0.82g (20.5mmol) and 25mL of water, drop it over in about 30min, keep the reaction at 60°C for 12h, cool, filter, wash with water, and dry in vacuo to obtain 11.8g of light yellow solid with a yield of 95.8%.

Embodiment 2

[0029] Example 2 Condensation of perfluorohexenyloxybenzenesulfonyl chloride and 1,4-butanediamine

[0030] A solution of 9.55g (20.2mmol) of perfluorohexenyloxybenzenesulfonyl chloride in 20mL of acetonitrile was slowly added dropwise to 0.88g (10.0mmol) of 1,4-butanediamine, 1.45g (10.5mmol) of potassium carbonate at 45°C ) and 25mL of water, dripped in about 30min, kept at 60°C for 18h, cooled, filtered, washed with water, and dried in vacuo to obtain 9.0g of light yellow solid with a yield of 93.7%.

Embodiment 3

[0031] Example 3 Condensation of N,N'-bis(perfluorononenyloxybenzenesulfonyl)ethylenediamine and sodium chloroethylsulfonate

[0032] N,N'-bis(perfluorononenyloxybenzenesulfonyl)ethylenediamine 6.16g (5.0mmol), sodium chloroethylsulfonate 3.33g (20.0mmol) and water 25mL were mixed, and sodium carbonate was added to adjust the pH to 10, react at 60°C for 24 hours, and add sodium carbonate during the reaction to keep the pH basically unchanged. Cool, filter, wash, and dry in vacuo to obtain 6.3 g of an amber solid product with a yield of 84.4%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Surface tensionaaaaaaaaaa
Minimum surface tensionaaaaaaaaaa
Minimum surface tensionaaaaaaaaaa
Login to view more

Abstract

The invention discloses a sulfonic acid dimeric surfactant based on perfluorononylene and perfluorohexylene, and a preparation method of the surfactant. The surfactant is a compound with a general formula as described in the specification. As perfluor alkene oxygen phenyl serves as a lipophilic group, sulphonate serves as a hydrophilic group, and a lipophilic part is connected with a hydrophilic part by a sulfonamide bond, the surfactant is very high in surface activity and lower in critical micelle concentration. The preparation method takes the perfluorononylene or the perfluorohexylene as a raw material, and comprises the steps of condensing with phenol, chlorosulfonation, diamine condensing, and sulphur alkylation condensing. The preparation method has the characteristics of simple process, lower cost and the like, and has good application prospects.

Description

technical field [0001] The invention relates to a class of fluorine surfactants, in particular to a class of sulfonic acid gemini surfactants containing perfluorononenyloxy or perfluorohexenyloxy groups, 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. aspects play an extremely important role. The most widely used fluorosurfactants are perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS) and their derivatives, but due to the non-biodegradability and long-distance migration of PFOA and PFOS compounds Restricted and Prohibited. Fluorosurfactants derived from hexafluoropropylene oligomers, especially hexafluoropropylene dimers and hexafluoropropylene trimers...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): B01F17/26B01F17/42C07C303/40C07C311/29C07C303/38C09K23/26C09K23/42
Inventor 郑土才赵颖俊
Owner 江苏中丽新材料有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap