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Synthesis and surface properties of a novel perfluoroalkyl-containing quaternary ammonium salt

XU Yunhuan,ZHENG Cheng,LIN Jing,MAO Taoyan,HUANG Wuhuan,GAN Yin   

  1. Fine Chemical Research Institute,Guangzhou University,Guangzhou 510006,Guangdong,China
  • Online:2014-02-05 Published:2014-02-05

新型含氟季铵盐表面活性剂的合成与表面性能

徐运欢,郑成,林璟,毛桃嫣,黄武欢,甘茵   

  1. 广州大学 精细化工研究所,广东 广州510006

Abstract: A novel perfluoroalkyl-containing quaternary ammonium salt was synthesized from N-methyl diethanolamine (MDEA) and perfluorinated hexyl ethyl iodide. The effects of solvent,reaction temperature,reactant molar ratio,solvent volume and reaction time on reaction on conversion rate were studied. The optimal process parameters for synthesizing product were obtained by orthogonal experiment,which are 8 mL n-butyl alcohol,90℃ reaction temperature,42 h reaction time,2.5∶1 molar ratio of perfluorinated hexyl ethyl iodide and MDEA. The conversion rate of MDEA was 93.75%. The structure of product was characterized by Fourier transform infrared spectroscopy,mass spectrometry and nuclear magnetic resonance spectrum. The surface properties of the surfactant were studied by measuring the surface tension of the product aqueous solution. The results showed that the critical micellar concentration (CMC) of the above perfluoroalkyl-containing quaternary ammonium salt was 1.518 mmol/L,the γCMC was 9.3 mN/m. The single molecule saturated adsorption,single molecule average areas on the saturated adsorption layer,and the micellization standard free energy were 0.354×10?10 mol/cm2,4.69 nm2,and ?26.03 kJ/mol,respectively. Compared with similar products,the product exhibited excellent surface properties.

Key words: perfluoroalkyl-containing quaternary ammonium salt, surfactants, N-methyl diethanolamine, surface tension, critical micellar concentration

摘要: 以N-甲基二乙醇胺(MDEA)和全氟己基乙基碘为主要原料,合成了一种新型的含氟季铵盐表面活性剂。通过单因素和正交实验,考察了溶剂、反应温度、反应物摩尔比、溶剂体积和反应时间对MDEA转化率的影响,探讨优化出最佳工艺条件:溶剂为正丁醇,反应温度90 ℃,n(全氟己基乙基碘)∶n(MDEA)=2.5∶1,溶剂体积为8 mL,反应时间为42 h,转化率达到93.75%。通过傅里叶红外吸收光谱、质谱和核磁共振谱对目标产物进行表征,并通过测定其水溶液的表面张力研究了产物的表面活性。其临界胶束浓度(CMC)为1.518 mmol/L,临界胶束浓度下的表面张力(γCMC)为9.3 mN/m;单分子饱和吸附量、单分子饱和吸附面积和胶束化标准自由能分别为0.354×10?10 mol/cm2、4.69 nm2和?26.03 kJ/mol。与同类产品相比较,产物具有优异的表面性能。

关键词: 含氟季铵盐, 表面活性剂, N-甲基二乙醇胺, 表面张力, 临界胶束浓度

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