New mild amphoteric sulfohydroxybetaine-type surfactants containing different labile spacers: Synthesis, surface properties and performance
New mild amphoteric sulfohydroxybetaine-type surfactants containing different labile spacers: Synthesis, surface properties and performance
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DOI：
10.1016/j.jcis.2019.09.100
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发表时间：
2020-01-15
影响因子：
9.9
通讯作者：
Wilk, Kazimiera A.
中科院分区：
文献类型：
--
作者：
Lamch, Lukasz;Witek, Kamila;Wilk, Kazimiera A.
假设：两性离子烷基酰胺型表面活性剂的优异性能可以通过对其结构的轻微修改来调整，特别是关于亲水和疏水部分之间的连接基团以及通过引入连接到氮上的甲基来缓和强NH氢键。研究了烷基酰胺羟基磺基甜菜碱型表面活性剂的结构对其吸附、胶束化、钙皂分散能力、在这项工作中研究了润湿性以及抗微生物和溶血活性。我们合成了一系列具有不稳定的-CO-N（Me）CH 2-或CH 2N（Me）-CO-间隔基的新型表面活性剂，这些间隔基与疏水尾部CnH 2n +1相邻，并通过C3 H 6或C2 H 4连接基与两性离子羟基磺基甜菜碱头基分开，即，[（3-烷酰甲基氨基）丙基]二甲基铵2-羟基丙磺酸盐（C（n）TMDAS）和[3-（烷基甲基氨基）-3-氧代丙基]二甲基铵2-羟基丙磺酸盐（C（n）DMPAS）。此外，C（n）TMDAS系列表现出显着更高的钙皂分散能力和较软的相互作用与生物系统比C（n）DMPAS。分子模拟计算表明，C（n）TMDAS分子的偶极矩较低，极性较低，从而导致表面活性的差异，而与油酸的二聚自由能较高，可能是形成混合胶束的原因。(C)2019爱思唯尔公司All rights reserved.
Hypothesis: The excellent performance of zwitterionic alkylamide-type surfactants may be tuned by slight modifications of their structures, especially concerning linking groups between hydrophilic and hydrophobic moieties and the moderation of strong NH hydrogen bonds via the introduction of a methyl group attached to the nitrogen.Experiments: The influence of the structure of alkylamidehydroxysulfobetaine-type surfactants on their adsorption and micellization, lime soap dispersing ability, wettability, as well as antimicrobial and hemolytic activities was studied in this work. We synthesized a series of novel surfactants with labile-CO-N (Me)CH2- or CH2N(Me)-CO- spacers that were adjacent to the hydrophobic tail CnH2n+1 and separated from the zwitterionic hydroxysulfobetaine headgroup by C3H6 or C2H4 linkers, i.e., [(3-alkanoyilomethyoa mine)propyl] dimethylammonium 2-hydroxypropanesulfonates (C(n)TMDAS) and [3-(alkylmetyloamino)-3-oxopropyl] dimethylammonium 2-hydroxypropanesulfonates (C(n)DMPAS), respectively.Findings: The C(n)TMDAS surfactants showed slightly higher surface activity and lower CMC than the respective C(n)DMPAS with the same number of carbon atoms. Moreover, the C(n)TMDAS series exhibited significantly higher lime soap dispersing abilities and softer interactions with biological systems than C(n)DMPAS. The molecular modeling computations revealed that the difference in surface activity originated from lower dipole moment of C(n)TMDAS, hence, lower polarity, whereas higher free energy of dimerization of those surfactants with oleic acid may account for the favorable formation of mixed micelles. (C) 2019 Elsevier Inc. All rights reserved.