Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants

Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants
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DOI:
10.1016/j.tetlet.2021.153113
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发表时间:
2021-06-07
影响因子:
1.8
通讯作者:
Wadouachi, Anne
Wadouachi, Anne
中科院分区:
化学4区
文献类型:
--
作者:
Abdellahi, Bemba;Bois, Remy;Wadouachi, Anne

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合成了3类单糖基上带有硫酸根官能团的糖基阴离子表面活性剂,并比较了它们的理化性质。第一家族对应于可商购的八-和十二烷基β-D-葡萄糖苷和半乳糖吡喃糖苷的6-硫酸酯衍生物。第二和第三家族在硫酸化单糖(半乳糖、葡萄糖或木糖)和疏水烷基链之间含有酰胺接头。十二合成的阴离子糖脂,包括9个新的硫酸化化合物,研究了它们在空气/液体界面的表面活性和它们的自组装性能。这些糖基表面活性剂显示出与商业阴离子表面活性剂(SDS和SLES)类似的表面性质,具有良好的降低表面张力的能力。所获得的结果证实了这些新的生物基分子在各种制剂中用于阴离子表面活性剂的潜在替代的兴趣。(C)2021爱思唯尔有限公司版权所有。
Three families of anionic sugar-based surfactants bearing a sulfate functional group on the primary position of a monosaccharide were synthesized and their physicochemical properties were compared. The first family corresponds to 6-sulfate derivatives of commercially available octa- and dodecyl beta-D-gluco- and galactopyranosides. The second and the third families contain an amide linker between the sulfated monosaccharide (galactose, glucose or xylose) and the hydrophobic alkyl chain. Twelve of the as-synthesized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good ability to reduce surface tension. The obtained results confirm the interest in these new bio-based molecules for potential substitution of anionic surfactants in various formulations. (C) 2021 Elsevier Ltd. All rights reserved.