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Preparation of a Novel Class of Cationic Gemini Imidazolium Surfactants Containing Amide Groups as the Spacer: Their Surface Properties and Antimicrobial Activity

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Journal of Surfactants and Detergents

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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Authors and Affiliations

  1. Chemistry and Chemical Engineering Institute, Qiqihar University, 161006, Qiqihar, People’s Republic of China

    Liyan Wang, Honglei Qin, Shichao Huo, Qigang Deng, Bing Zhao & Lingwei Meng

  2. Key Laboratory of Enhanced Oil and Gas Recovery, Ministry of Education, Northeast Petroleum University, 163318, Daqing, People’s Republic of China

    Liyan Wang & Tie Yan

  3. Cadre Ward, Qiqihar First Hospital, 161005, Qiqihar, People’s Republic of China

    Limin Ding

Authors
  1. Liyan Wang
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  2. Honglei Qin
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  3. Limin Ding
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  4. Shichao Huo
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  5. Qigang Deng
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  6. Bing Zhao
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  7. Lingwei Meng
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  8. Tie Yan
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Correspondence to Qigang Deng or Tie Yan.

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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

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