Abstract
A class of novel cationic Gemini imidazolium surfactants containing amide groups as the spacer were synthesized from ethylenediamine and 1-bromoalkane(C8, C10, C12, C14, C16) by N-alkylation to get N,N′-dialkyl ethylenediamine (1a–e), 1a–e was further reacted with chloroacetyl chloride by N-acylation to get N,N′-(ethane-1,2-diyl)bis(2-chloro-N-alkylacetamide) (2a–e), which was further reacted respectively with 1-methyl imidazole by quaternized to form the surfactant molecule, N,N′-((ethane-1,2-diyl)bis(alkyl-azanediyl)bis(2-oxoethane-2,1-diyl)) bis(1-methyl-1H-imidazol-3-ium) dichloride. The structures of intermediates (1a–e) and (2a–e) were characterized by IR and 1H NMR. The structures of the surfactants (3a–e) were characterized by IR, 1H-NMR and 13C-NMR and element analysis. The critical micelle concentrations (CMC) of 3a–e were determined by the conductivity method at 25 °C. The CMC values decreased with increasing the length of the hydrophobic chain. The surfactants (3a–e) showed good foaming stability, emulsion ability and wetting ability. The surfactants (3a–e) also have good antimicrobial activity against Staphylococcus aureus, Escherichia coli and Bacillus subtilis.
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Acknowledgments
We thank the Science and Technology Fund of Heilongjiang Province of China (grant No. B201116), the Overseas Scholars Foundation of Scientific and Technical Agency of Heilongjiang province Foundation of China (No. LC2011C17), the Program for YJSCX Scientific Research in Heilongjiang province (grant No. YJSCX2013-ZD12) and the College Students’ Innovative Entrepreneurial Training Project of Heilongjiang province of China (201410221015).
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Wang, L., Qin, H., Ding, L. et al. Preparation of a Novel Class of Cationic Gemini Imidazolium Surfactants Containing Amide Groups as the Spacer: Their Surface Properties and Antimicrobial Activity. J Surfact Deterg 17, 1099–1106 (2014). https://doi.org/10.1007/s11743-014-1614-1
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DOI: https://doi.org/10.1007/s11743-014-1614-1