全氟己基季铵盐型表面活性剂的制备及其表面活性

Synthesis and Properties of Ammonium Salts of Perfluorohexylsulfonamides

摘要:

以全氟己基磺酰氟和N,N-二甲基-1,3-丙二胺为原料，经酰胺化和季铵化反应，制备了N,N,N-三甲基-N-(N’-全氟己基磺酰胺基)丙基碘化铵。用IR、1H NMR、MS（ESI）等方法对其结构进行了表征，并测试了表面张力等性能。结果显示：N,N-二甲基-N’-全氟己基磺酰基丙二胺合成的较佳工艺条件为：乙酸乙酯为溶剂，三乙胺为缚酸剂，n(C6F13SO2F)：n[H2NC3H6N(CH3)2]＝1:1.2, 室温反应3 h，收率为90.9 %。季铵化反应的较优合成条件：四氯化碳为溶剂，n[C6F13SO2NHC3H6N(CH3)2]：n(CH3I)＝1:1.7，室温下反应2 h，收率为97.6%。所得季铵盐临界胶束浓度（CMC）为3.50 mmol/L，在CMC时表面张力为17.8 mN/m，具有良好的表面活性。

Abstract:

N-[3-perfluorohexylsuflonamido)propyl] -N,N,N-trimethyl ammoniuim iodide [I] was prepared by amidation from perfluorohexylsulphonyl fluoride [II] and N,N-dimethyl-1,3-propane diamine [III], then quaternization with methyl iodide [IV], and was characterized by IR, 1H NMR, and MS. The surface tension (γ) and critical micelle concentration (CMC) of aqueous solutions of I were investigated. The optimal process conditions of amidation: n(II)：n[III]＝1:1.2, the reactants agitated at room temperature for 3h in EtOAc and in the presence of N(Et)3. the reaction temperature to give C6F13SO2NHC3H6N(CH3)2 [V] in the yield of 90.9%. The optimal process conditions of quaternization: n[V] : n(IV)＝1:1.7, V and IV reacted at room temperature for 2h in CCl4 to give I in the yield of 97.6 %. The CMC of aqueous solution of I is 3.50 mmol/L and its γCMC is 17.8 mN/m which show excellent performance of surface activity of I.