Page 116 - 《精细化工》2022年第9期

第 39 卷第 9 期 精 细 化 工 Vol.39, No.9
2022 年 9 月 FINE CHEMICALS Sept. 2022

表面活性剂
葡萄糖酰胺季铵盐表面活性剂的合成与性能

智丽飞，石秀芳，张二壮，李泽鑫，冯政民，潘瑞丽

（太原科技大学 化学与生物工程学院，山西 太原 030024）

摘要：以 D-葡萄糖酸-δ-内酯、N,N-二丁基-1,3-丙二胺和溴代烷为原料，采用先胺酯反应、后季铵化两步法合成
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1
了系列葡萄糖酰胺季铵盐表面活性剂（C n DGMAPB，n=8、10、12、14、16）。采用 FTIR、 HNMR 和 CNMR
对中间体和产物结构进行了鉴定，并对其表面活性、润湿性能、乳化性能、泡沫性能和产品毒性进行了研究。
结果显示，C n DGMAPB 具有较好的表面活性，随着碳链长度的增长，临界胶束浓度（cmc）和分子截面积（A min ）
逐渐减小，表面活性效率（pC 20 ）和饱和吸附量（Г max ）逐渐增大，表面张力（γ cmc ）为 28~32 mN/m。在表面活
性剂浓度为 0.01~5 mmol/L 范围内，C 12 DGMAPB 和 C 16 DGMAPB 溶液与聚四氟乙烯（PTFE）膜的接触角降低
到 47º，此类糖基酰胺季铵盐具有较好的润湿和乳化性能。5 min 时泡沫体积都很小，属于典型的低泡型产品。
此类葡萄糖酰胺季铵盐表面活性剂为低毒产品。当 C 12 DGMAPB 质量浓度在 0.2 g/L 时，对大肠杆菌和金黄色葡
萄球菌的抑菌率都能达到 100%，对皮肤无刺激，具有较好的抗静电性能。
关键词：糖基酰胺；季铵盐；表面活性；泡沫；毒性
中图分类号：O647.2 文献标识码：A 文章编号：1003-5214 (2022) 09-1834-12

Synthesis and performance of glucosamide quaternary
ammonium salt surfactants

ZHI Lifei, SHI Xiufang, ZHANG Erzhuang, LI Zexin, FENG Zhengmin, PAN Ruili
（College of Chemistry and Biological Engineering, Taiyuan University of Science and Technology, Taiyuan 030024,
Shanxi, China）

Abstract: A series of glucosamide quaternary ammonium salt surfactants (C nDGMAPB, where n represents
the carbon chain length of 8, 10, 12, 14 and 16) were successfully synthesized from D-glucose-δ-lactone,
N,N-dibutyl-1,3-diaminopropane and bromoalkane using a two-step method of amine ester reaction and
quaternary ammonium reaction. The intermediates and products obtained were then characterized by FTIR,
1 13
HNMR and CNMR, followed by investigations on the surface activity, wettability, emulsifying and
foaming properties, and toxicity of the products. The results showed that C nDGMAPB had good surface
activity. Meanwhile, the increase of carbon chain length led to the reduction of the critical micelle
concentration (cmc) and molecular cross-sectional area (A min) and the gradual increase of the surface
activity efficiency (pC 20) and saturated adsorption capacity (Г max), while the surface tension (γ cmc) was
maintained between 28~32 mN/m. The contact angle between C 12DGMAPB/C 16DGMAPB solution and
polytetrafluoroethylene (PTFE) membrane was reduced to 47° in the concentration range of 0.01~5 mmol/L.
This kind of glycosylamide quaternary ammonium salt showed good wetting and emulsifying properties.
The foam volume was very low at 5 min, which indicated that the products were typical low foam products.
In addition, the C nDGMAPB surfactants also exhibited low toxicity. The C 12DGMAPB with a mass
concentration of 0.2 g/L displayed a 100% antibacterial rate to Escherichia coli and Staphylococcus aureus
with no skin irritation and good antistatic performance.
Key words: glucosamide; quaternary ammonium salt; surface activity; foam; toxicity

收稿日期：2022-03-12; 定用日期：2022-07-19; DOI: 10.13550/j.jxhg.20220218
基金项目：国家自然科学基金（22002105）；山西省高等学校科技创新项目（2020L0355）
作者简介：智丽飞（1981—），女，副教授，E-mail：lifeizhi@yeah.net。