含全氟壬烯基的阳离子氟表面活性剂的合成

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

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。

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 CH3 CN, 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.