含全氟壬烯基的阳离子氟表面活性剂的合成

以p-全氟壬烯氧基苯甲酸为原料,经酰氯化、酰胺化和季铵化三步反应,制备了N-3-(p-全氟壬烯氧基苯甲酰氨基)丙基]-N,N,N-三甲基碘化铵(Ⅰ),用IR、1HNMR、19FNMR对其结构进行了表征,并测试了其水溶液的表面张力。p-C9F17OC6H4COOH(Ⅱ)与过量SOCl2在40℃反应3 h后,与N,N-二甲基丙二胺反应,n(Ⅱ)∶n(N,N-二甲基丙二胺)=1∶2,乙腈作溶剂,70℃反应1 h,N-3-(p-全氟壬烯氧基苯甲酰氨基)丙基]-N,N-二甲基胺(Ⅲ)收率89.3%。Ⅰ的较佳合成工艺条件为:n(Ⅲ)∶n(碘甲烷)=1∶1.2,乙腈作溶剂,回流1.5 h,收率88.3%。Ⅰ的水溶液CMC为9.67×10-4mol/L,γ为20.4 mN/m。

Synthesis of N-[3-(p-Perfluorononenyloxybenzamido)-propyl]-N,N,N-trimethyl Ammonium Iodide

p-Perfluorononenyloxybenzoic acid(Ⅱ) was reacted with SOCl2,then condensed with N,N-dimethyl propylene diamine,and finally quaternized with methyl iodide to produce N-3-(p-perfluorononenyloxybenzamido)-propyl]-N,N,N-trimethyl ammonium iodide(Ⅰ).This product was characterized by IR,1HNMR and 19FNMR.The surface tension(γ) and the critical micelle concentration(CMC) of aqueous solutions of Ⅰ were investigated.Ⅱ reacted with the overdosage SOCl2 at 40 ℃ for 3 h,then condensed with N,N-dimethyl propylene diamine in CH3CN,n(Ⅱ)∶n(N,N-dimethyl propylene diamine)=1∶2,and agitated at 70 ℃ for 1 h to give N-3-(p-perfluorononenyloxy benzamido)-propyl]-N,N-dimethylamine(Ⅲ) in the yield of 89.3%.Ⅲ reacted with CH3I in CH3CN,n(Ⅲ)∶n(CH3I)=1∶1.2,and refluxed for 1.5 h to give Ⅰ in the yield of 88.3%.The CMC and γCMC of Ⅰ were 9.67×10-4 mol/L and 20.4 mN/m respectively.