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Novel glucose-derived gemini surfactants with a 1,1′-ethylenebisurea spacer: Preparation, thermotropic behavior, and biological properties

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Journal of Surfactants and Detergents

Abstract

In the search for environmentally safe surfactants made from inexpensive and renewable sources, the interest has mainly been focused on new saccharide derivatives. This report describes the synthesis of newly designed nonionic gemini compounds comprising two reduced sugar headgroups, two alkyl tails, and a 1,1′-ethylenebisurea entity as the spacer linking two amphiphilic glucose-derived moieties. Thus, the series of N,N′-bis[(3-alkyl-3-deoxy-d-glucitol)ureido]ethylenediamines (bis(CnGT), with Cn=n-C9H9, n-C6-H13, n-C8H17, n-C10H21, or n-C12H25), were prepared using a convenient procedure starting from easily accessible reagents such as d-glucose, n-alkylamines, urea, and ethylenediamine. Their structure and purity were confirmed by means of elemental analysis, electrospray ionization mass spectrometry, and 1H and 13C nuclear magnetic resonance spectroscopy. Additionally, the present contribution introduces selected properties of these surfactants, including their thermotropic behavior and biological properties. The presence of two phase transition points, determined using the differential scanning calorimetry method, indicates liquid-crystalline mesophase formation upon heating. Furthermore, using the closed-bottle test (OECD Guideline 301D) as well as the biological oxygen demand test for insoluble substances for biodegradability measurements, it has been concluded that the tested glucose-derived gemini structures achieve more than 60% biodegradation after 64–75 test days. All tested surfactants were practically nontoxic to bacteria, yeast, and molds. Owing to their fitting aggregation ability as well as their nontoxicity, they constitute an interesting group of surfactants for various applications.

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Abbreviations

bis(CnCT):

N,N′-bis[3-alkyl-3-deoxy-D-glucitol) ureido]ethylenediamines

BOD:

biological oxygen demand

BODIS:

biological oxygen demand test for insoluble substances

cfu:

colony forming units

DSC:

differential scanning calorimetry

ESI-MS:

electrospray ionization mass spectrometry

MIC:

minimal inhibitory concentration

NMR:

nuclear magnetic resonance

PCM:

Polish Collection of Microorganisms

TOD:

theoretical oxygen demand

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Authors and Affiliations

  1. Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, Wroclaw, Poland

    Irena Maliszewska & Ludwik Syper

  2. Institute of Organic and Polymer Technology, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370, Wroclaw, Poland

    Urszula Laska & A. Wilk

Authors
  1. Urszula Laska
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  2. A. Wilk
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  3. Irena Maliszewska
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  4. Ludwik Syper
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Correspondence to A. Wilk.

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Laska, U., Wilk, A., Maliszewska, I. et al. Novel glucose-derived gemini surfactants with a 1,1′-ethylenebisurea spacer: Preparation, thermotropic behavior, and biological properties. J Surfact Deterg 9, 115–124 (2006). https://doi.org/10.1007/s11743-006-0380-0

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  • DOI: https://doi.org/10.1007/s11743-006-0380-0

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