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Synthesis, Characterization and Properties of New Lauryl Amidopropyl Trimethyl Ammoniums

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Journal of Surfactants and Detergents

Abstract

A new lauryl amidopropyl trimethyl ammonium methyl carbonate with the formula CH3(CH2)10CONH(CH2)3N+(CH3)3CH3CO3 − was synthesized via a high pressure process with tertiary amines and dimethyl carbonate, and its chemical structure was confirmed using 1H-NMR spectra, mass spectral fragmentation, and FTIR spectroscopic analysis. In addition, several quaternary ammonium salts with new counterions X− (X−=HCO3 −, HCOO−, CH3COO−, CH3CH(OH)COO−) were also synthesized by the ion exchange reaction of methyl carbonate quaternary ammoniums with corresponding acids. The surface activities of these compounds were measured, including surface tension (γ), critical micelle concentration and minimum surface area (A min) at 25 °C. Adsorption and micellization free energies of these quaternary ammonium salts in their solutions showed a good tendency towards adsorption at interfaces. The antimicrobial activities are reported for the first time against representative bacteria and fungi for lauryl amidopropyl trimethyl ammoniums. It was found that the antimicrobial potency was Gram-positive bacteria > fungi > Gram-negative bacteria.

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Acknowledgments

We gratefully acknowledge the financial support of the National Natural Science Foundation of China (20976003, 21176004) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of the Beijing Municipality (PHR200906109).

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Authors and Affiliations

  1. Beijing Key Laboratory of Flavor Chemistry, School of Food and Chemical Engineering, Beijing Higher Institution Engineering Research Center of Food Additives and Ingredients, Beijing Technology and Business University, No. 11 Fucheng Road, Beijing, 100048, People’s Republic of China

    Hongqin Liu, Fei Li, Baocai Xu, Guiju Zhang, Fu Han, Yawen Zhou & Xiulan Xin

  2. College of Engineering, University of Illinois at Urbana-Champaign, Urbana-Champaign, IL, 61801-3636, USA

    Bo Xu

Authors
  1. Hongqin Liu
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  2. Fei Li
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  3. Baocai Xu
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  4. Guiju Zhang
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  5. Fu Han
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  6. Yawen Zhou
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  7. Xiulan Xin
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  8. Bo Xu
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Corresponding author

Correspondence to Baocai Xu.

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Liu, H., Li, F., Xu, B. et al. Synthesis, Characterization and Properties of New Lauryl Amidopropyl Trimethyl Ammoniums. J Surfact Deterg 15, 709–713 (2012). https://doi.org/10.1007/s11743-012-1350-3

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  • DOI: https://doi.org/10.1007/s11743-012-1350-3

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