含有机反离子的双子季铵盐的合成与性能

Preparation and properties of Gemini quaternary ammonium salts with organic counterions

摘要:

以十二烷基二甲基叔胺、环氧氯丙烷和对甲基苯磺酸为原料，合成了一种反离子含有机酸根的异丙醇基双子季铵盐GC-S。通过正交实验优化合成工艺，得到合成的最佳反应时间、反应温度与物质的量比。利用FTIR、1HNMR和ESI-MS对产物结构进行鉴定，证明了预期结构的合成。GC-S具有较高的表面活性，cmc为24.06 mN/m，CMC为2.09×10-4 mol/L。与以氯为反离子的传统双子季铵盐GC-Cl和单链季铵盐1231相比，GC-S展现出更好的润湿性（其棉片下沉时间较短，平均为175.2 s）；展现出更好的起泡和稳泡性能（其起始泡沫体积较大，为390 mL；5 min时消泡体积较小，为20 mL）；展现出更好的乳化性能（其分出定量水层的时间较长，为317 s）；对大肠杆菌和金黄色葡萄球菌均表现出极高的抑菌活性。

Abstract:

An isopropanol-based Gemini quaternary salt (GC-S) with organic counterion was synthesized from dodecyl dimethyl tertiary amine, epichlorohydrin and p-toluenesulfonic acid. The synthesis process was optimized by orthogonal experimental. The products were characterized by FTIR , 1HNMR and ESI-MS, which demonstrated the successful synthesis of the expected structures. GC-S had a high surface activity with a cmc of 24.06 mN/m and a CMC of 2.09×10-4 mol/L. GC-S was compared with conventional Gemini quaternary ammonium salt with chloride as counterions (GC-Cl) and single-chain quaternary ammonium salt (1231). The results indicated that GC-S had better wettability because of the shortest sink time (175.2 s) for canvas swabs in aqueous solution. GC-S showed better foaming and foam stabilization performance due to larger starting foam volume (390 mL) and smaller defoaming volume (20 mL). GC-S displayed better emulsification performance because the partition out the quantitative aqueous layer from the emulsification system of aqueous solutions with liquid paraffin needed a larger time (317 s). GC-S (10 mg/kg) showed very high antibacterial activity against both E. coli and Staphylococcus aureus.