葡萄糖酰胺季铵盐表面活性剂的合成与性能
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太原科技大学 化学与生物工程学院

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O647.2

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


Synthesis and performance of glucosamide quaternary ammonium salt surfactants
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College of Chemistry and Biological Engineering,Taiyuan University of Science and Technology,China,030024

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    摘要:

    以葡萄糖酸内酯、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(CnDGMAPB,n=8、10、12、14、16)。采用FTIR、1HNMR和13CNMR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等性能进行研究。结果显示,CnDGMAPB具有较好的表面活性,随着碳链的增长,临界胶束浓度(cmc)和分子截面积(Amin)逐渐减小,表面活性效率(pC20)和饱和吸附量(Гmax)逐渐增大,表面张力(γcmc)在28~32 mN/m之间。在考察浓度(0.01-5 mmol/L)范围内,C12DGMAPB和C16DGMAPB溶液与聚四氟乙烯膜(PTFE)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。细胞毒性和急性经口毒性实验均显示,此类葡萄糖酰胺季铵盐表面活性剂为低毒产品。当C12DGMAPB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。

    Abstract:

    A series of glucosamide quaternary ammonium salt surfactants (CnDGMAPB, where n represents the hydrocarbon chain length of 8, 10, 12, 14 and 16) were successfully synthesized from glucosactone, N, N-dibutyl-1, 3-diaminopropane, and bromoalkane using two-step method of amine ester reaction and quaternary ammonium reaction. The intermediates and products were characterized by FTIR, 1H-NMR and 13C-NMR. The surface activity, wettability, emulsifying, foam and toxicity of the product were studied. The results showed that CnDGMAPB has good surface activity. The critical micelle concentration (cmc) and molecular cross-sectional area (Amin) decreases, the surface activity efficiency (pC20) and saturated adsorption capacity (Гmax) gradually inceased with increasing the carbon chain length. The surface tension (γcmc) value was between 28-32 mN/m. The contact angle between C12DGMAPB/ C16DGMAPB solution and polytetrafluoroethylene membrane (PTFE) was reduced to 47o within the concentration (0.01-5 mmol/L) range. This kind of glycosylamide quaternary ammonium salt had good wetting and emulsifying properties. The foam volume was very low at 5 min, which belongs to the typical low foam product. Both cell toxicity and acute oral toxicity experiment showed that the CnDGMAPB surfactants were low-toxic products. The antibacterial rate of escherichia coli and staphylococcus aureus can reach 100% at the C12DGMAPB concentration of 0.2 g/L, no irritation to skin, and has good antistatic performance.

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智丽飞,石秀芳,张二壮,李泽鑫,冯政民,潘瑞丽.葡萄糖酰胺季铵盐表面活性剂的合成与性能[J].精细化工,2022,39(10):

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  • 收稿日期:2022-03-12
  • 最后修改日期:2022-07-09
  • 录用日期:2022-07-19
  • 在线发布日期: 2022-09-16
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