葡萄糖酰胺季铵盐表面活性剂的合成与性能  

Synthesis and performance of glucosamide quaternary ammonium salt surfactants

作　　者：智丽飞 石秀芳 张二壮 李泽鑫 冯政民 潘瑞丽[1] 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)

机构地区：[1]太原科技大学化学与生物工程学院,山西太原030024

出　　处：《精细化工》2022年第9期1834-1844,1865,共12页Fine Chemicals

基　　金：国家自然科学基金(22002105);山西省高等学校科技创新项目(2020L0355)。

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、^(1)HNMR和^(13)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47°,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。A series of glucosamide quaternary ammonium salt surfactants(C_(n)DGMAPB,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) HNMR and ^(13) CNMR,followed by investigations on the surface activity,wettability,emulsifying and foaming properties,and toxicity of the products.The results showed that C_(n)DGMAPB 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_(12)DGMAPB/C_(16)DGMAPB 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_(n)DGMAPB surfactants also exhibited low toxicity.The C_(12)DGMAPB 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.

关 键 词：糖基酰胺 季铵盐 表面活性 泡沫 毒性 

分 类 号：O647.2[理学—物理化学]