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Cation fluorine surfactant and preparation method thereof

A fluorosurfactant and cation technology, applied in the field of cationic fluorosurfactant and its preparation, to achieve the effects of low surface tension, simple synthesis method and high reaction yield

Inactive Publication Date: 2008-10-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no literature on cationic fluorosurfactants containing benzoyl groups

Method used

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  • Cation fluorine surfactant and preparation method thereof
  • Cation fluorine surfactant and preparation method thereof
  • Cation fluorine surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 50mL trichloroethane, 28.4g (0.05mol) p-perfluorononenyloxybenzoic acid (Lianyungang Taizhuo New Material Co., Ltd.) into a 250mL four-necked flask, stir, heat to 40℃, and slowly add 7.14 g(0.06mol) thionyl chloride, continue to stir for 3h. Raise the temperature to 76°C, keep the temperature and stir until no gas escapes. Cool to 50℃, slowly add 5.1g (0.05mol) N,N-dimethylpropanediamine in trichloroethane (10mL) solution, stir for 0.5h, add 5.3g (0.05mol) sodium carbonate powder, stir Reaction for 3h. Cool to room temperature, add 50 mL of water and stir, stand still for layering, separate to obtain an organic phase, and distill under reduced pressure to remove trichloroethane to obtain a solid. Add this solid substance and 30 mL acetonitrile to a 100 mL four-neck flask, and heat and stir until the solid is dissolved. The temperature was continued to rise to 60°C, and a solution of 7.1g (0.05mol) methyl iodide in acetonitrile (10 mL) was slowly added dropwise, and the ...

Embodiment 2

[0033] Add 50 mL of trichloroethane and 28.4 g of p-perfluorononenyloxy benzoic acid to a 250 mL four-necked flask, stir, heat to 30° C., slowly add 8.9 g (0.075 mol) thionyl chloride dropwise, and continue stirring for 4 hours. Raise the temperature to 76°C, keep the temperature and stir until no gas escapes. Cool to 60°C, slowly add 6.1g (0.06mol) N,N-dimethylpropanediamine in trichloroethane (10 mL) solution, stir for 0.5h, add 8.0g (0.075mol) sodium carbonate powder, The reaction was stirred for 4h. Cool to room temperature, add 50 mL of water and stir, stand still for layering, separate the organic phase, and distill under reduced pressure to remove the trichloroethane to obtain a solid. The solid matter and 30 mL of ethyl acetate were added to a 100 mL four-neck flask, and heated and stirred until the solid was dissolved. The temperature was continued to rise to 70°C, and a solution of 8.5g (0.06mol) methyl iodide in ethyl acetate (10 mL) was slowly added dropwise, and stirr...

Embodiment 3

[0035]Add 50mL cyclohexanone and 28.4g p-perfluorononenyloxybenzoic acid to a 250mL four-necked flask, stir, heat up to 50°C, slowly add 9.5g (0.08mol) thionyl chloride dropwise, and continue stirring for 6h. Raise the temperature to 76°C, keep the temperature and stir until no gas escapes. Cool to 70°C, slowly add 7.7g (0.075mol) N,N-dimethylpropanediamine in cyclohexanone (10mL) solution dropwise, stir for 0.5h, add 8.1g (0.08mol) triethylamine, stir to react 5h. Cool to room temperature, add 50 mL of water and stir, stand still for layering, separate to obtain an organic phase, and distill under reduced pressure to remove cyclohexanone to obtain a solid. Add the solid matter and 30 mL of N,N-dimethylformamide to a 100 mL four-neck flask, and heat and stir until the solid is dissolved. The temperature was continued to rise to 80°C, and 11.3g (0.08mol) of methyl iodide in N,N-dimethylformamide (10 mL) was slowly added dropwise, and stirred at 80°C for 5h. The solvent was distille...

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Abstract

The invention provides a cationic fluorosurfactant (I) and a preparation method thereof. The method comprises adopting perfluorobutenyloxy benzoic acid and thionyl chloride as raw materials to perform a chloroacylation reaction at -30 DEC C to 70 DEC C in polar solvent, adding N,N-dimethyl propylene diamine and base catalyst, performing an amidation reaction at -20 DEC C to 120 DEC C, separating the reactant liquor to obtain N-[3-(p-perfluorobutenyloxybenzamido)propyl]-N, N-dimethyl amine, dissolving into non-proton polar solvent, adding iodomethane, performing a quaternization reaction at 0 DEC C to 100 DEC C, and filtering the reactant liquor to obtain N-[3-(p-butenyloxybenzamido)propyl]-N,N,N-trimethyl ammonium iodide. The method has simple synthetic method and high reaction yield. Aqueous solution prepared from the N-[3-(p-butenyloxybenzamido)propyl]-N,N,N-trimethyl ammonium iodide has low surface tension.

Description

(1) Technical field [0001] The invention relates to a cationic fluorosurfactant and a preparation method thereof. (2) Background technology [0002] Fluorosurfactants are attracting more and more attention due to their special properties of "three highs and two phobias". They are currently the most active type of surfactants. They are mainly used in special occasions with higher technical requirements or general Areas where surfactants are difficult to handle and have poor application effects. Its fluorine-containing hydrocarbon group is both water-repellent and oil-repellent [New Chemical Materials, 2004, 32(8):46]. Cationic fluorocarbon surfactants are one of the important varieties of fluorosurfactants, which are mainly divided into two categories: amine salt type and quaternary ammonium salt type [Fluorosurfactant [M]. Beijing, China Light Industry Press, 1998: 7 ], and the quaternary ammonium salt type is the most widely used. [0003] The quaternary ammonium salt type catio...

Claims

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Application Information

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IPC IPC(8): C07C235/46C07C231/02B01F17/22C09K23/22
Inventor 史鸿鑫
Owner ZHEJIANG UNIV OF TECH
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