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Synthesis and surface properties of N-dodecyl-N,N-bis[3-(aldonamido)propyl]amine-N-oxides

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Journal of Surfactants and Detergents

Abstract

A new group of saccharide surfactants, N-dodecyl-N,N-bis[3-(aldonamido)propyl]amine-N-oxides (derivatives of d-gluconic, d-glucoheptonic, and lactobionic acids), were synthesized with high yields by one-step oxidation reaction of an appropriate N-dodecyl-N,N-bis[3-(aldonamido)-propyl]amine with an excess of 30 wt% of an aqueous solution of hydrogen peroxide. Their structures and purity were confirmed by means of elemental analysis, electrospray ionization mass spectrometry, and 1H and 13C nuclear magnetic resonance spectroscopy. In comparison to an appropriate N-dodecyl-N,N-bis[3-(aldonamido)propyl]amine, the investigated N-oxides are more soluble in water with similar critical micelle concentration values and show higher surface effectiveness. They are low-foamable but in mixtures with sodium dodecyl sulfate form high-volume and stable foams in a wide range of mixture compositions.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, 50-370, Wrocław, Poland

    Ludwik Syper

  2. Institute of Organic and Polymer Technology, Wrocław University of Technology, Wybrzeże Stanisława Wyspiańskiego 27, 50-370, Wrocław, Poland

    Andrzej Piasecki & Sławomir Karczewski

Authors
  1. Andrzej Piasecki
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  2. Sławomir Karczewski
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  3. Ludwik Syper
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Correspondence to Andrzej Piasecki.

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Piasecki, A., Karczewski, S. & Syper, L. Synthesis and surface properties of N-dodecyl-N,N-bis[3-(aldonamido)propyl]amine-N-oxides. J Surfact Deterg 4, 349–353 (2001). https://doi.org/10.1007/s11743-001-0186-0

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  • DOI: https://doi.org/10.1007/s11743-001-0186-0

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