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P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof

A technology of perfluorononenyloxybenzenesulfonyl chloride and nonenyloxybenzenesulfonic acid, which can be used in the preparation of sulfonic acid esters, chemical instruments and methods, transportation and packaging, etc., can solve the problems of low surface activity, etc. Application prospect, simple synthesis method, high surface activity effect

Active Publication Date: 2012-07-18
慕名信息技术(南通)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are very few reports on polyethylene glycol sulfonate-type fluorocarbon surfactants. Zeng Yuhua synthesized polyethylene glycol perfluoroalkylsulfonate with perfluoroalkylsulfonyl chloride and polyethylene glycol, but due to sulfonic acid The ester group is easily hydrolyzed by alkali, R F The carbon chain is too long, the surface activity is not high, and the surface tension of aqueous solution can reach 31mN / m [fluorocarbon surfactant [M]. Beijing: Chemical Industry Press, 2001: 93]
Polyethylene glycol p-perfluorononenyloxybenzenesulfonate (PFNPS-PEG-n) was synthesized from p-perfluorononenyloxybenzenesulfonyl chloride (PFNPSC) and polyethylene glycol (PEG-n). n) Surfactant, not yet reported

Method used

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  • P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof
  • P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof
  • P-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and preparation method as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 250mL four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, add 50mL (0.5mol) ethyl acetate, 30g (0.05mol) polyethylene glycol-600, 5.06g (0.05mol) Triethylamine, stirred, cooled to 10°C, slowly added dropwise 31.1g (0.05mol) p-perfluorononenyloxybenzenesulfonyl chloride in 50mL CCl 4 The solution was added dropwise for about 30 minutes, and the stirring reaction was continued at 10°C for 24 hours. Distilled under reduced pressure to remove the solvent to obtain a yellow viscous paste (a mixture of monoester and diester). The surface tension of the 0.5 g / L product aqueous solution measured at 20° C. was 22.6 mN / m.

[0024] Product structure characterization:

[0025] FT-IR (KBr, cm-1): 3424, 2873, 1663, 1488, 1282, 1180, 1092, 971, 838, 737.

[0026] 19 F NMR δ(CDCl 3 ): -169.8, -167.7, -72.8, -71.5, -56.3.

Embodiment 2

[0028] The reaction was carried out according to Example 1, but the solvent 50mL ethyl acetate was changed to 150mL N,N-dimethylformamide, and the amount of p-perfluorononenyloxybenzenesulfonyl chloride was changed to 155.67g (0.25mol), 5.06 The g of triethylamine was changed to 42.5 g of piperidine (0.50 mol), the reaction temperature was changed to 150° C., and the reaction time was changed to 1 h.

[0029] A yellow viscous paste (a mixture of monoester and diester) was obtained, and the surface tension of a 0.5 g / L product aqueous solution measured at 20° C. was 20.6 mN / m.

Embodiment 3

[0031] The reaction was carried out according to Example 1, but the solvent 50mL ethyl acetate was changed to 75mL N,N-dimethylformamide, and the amount of p-perfluorononenyloxybenzenesulfonyl chloride was changed to 34.2g (0.055mol), 5.06 The g of triethylamine was changed to 13.9 g of sodium bicarbonate (0.165 mol), the reaction temperature was changed to 50° C., and the reaction time was changed to 7 hours.

[0032] A yellow viscous paste (a mixture of monoester and diester) was obtained, and the surface tension of a 0.5 g / L product aqueous solution measured at 20° C. was 21.5 mN / m.

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Abstract

The invention discloses a p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester and a preparation method as well as application thereof. The structure of the p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester is shown in a formula (I) or formula (II), or the p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester is a mixture of compounds shown in the formula (I) and the formula (II). The p-perfluorous nonene oxygen group benzene sulfonic acid polyethylene glycol ester provided by the invention has high surface activity, can be used as a surface active agent and has wide application.

Description

(1) Technical field [0001] The invention relates to polyethylene glycol p-perfluorononenyloxybenzenesulfonate and its preparation method and application. (2) Background technology [0002] Compared with ordinary surfactants, fluorosurfactants have outstanding properties of "three highs and two phobias", that is, high surface activity, high heat resistance stability and chemical inertness, which are both water-repellent and oil-repellent [Chemical New Materials, 2004 , 32(8): 46]. The high surface activity of fluorosurfactants is due to the small van der Waals attraction between molecules, which leads to strong surface adsorption. Fluorosurfactants not only have a low affinity for water, but also have a low affinity for hydrocarbons, thus forming a hydrophobic and oil-repellent characteristic. In addition, due to the C-F bond energy (4.9×10 5 J·mol -1 ) is greater than the bond energy of the C-H bond (4.2×10 5 J·mol -1 ), the C-F bond is less likely to break than the C-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C07C309/75C07C303/28B01F17/42C09K23/42
Inventor 史鸿鑫赵琴琴
Owner 慕名信息技术(南通)有限公司
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