Journal of Surfactants and Detergents

, Volume 9, Issue 2, pp 115–124

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

  • Urszula Laska
  • A. Wilk
  • Irena Maliszewska
  • Ludwik Syper
Article

DOI: 10.1007/s11743-006-0380-0

Cite this article as:
Laska, U., Wilk, A., Maliszewska, I. et al. J Surfact Deterg (2006) 9: 115. doi:10.1007/s11743-006-0380-0

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.

Key Words

Antimicrobial activitybiodegradabilityDSC1,1′-ethylenebisurea derivativesnonionic glucose-derived gemini surfactantsthermotropic behavior

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

Copyright information

© AOCS Press 2006

Authors and Affiliations

  • Urszula Laska
    • 2
  • A. Wilk
    • 2
  • Irena Maliszewska
    • 1
  • Ludwik Syper
    • 1
  1. 1.Institute of Organic Chemistry, Biochemistry and BiotechnologyWroclaw University of TechnologyWroclawPoland
  2. 2.Institute of Organic and Polymer TechnologyWroclaw University of TechnologyWroclawPoland