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Surface and Self-Aggregation Properties of Bis-Benzimidazolones Derivatives of d-Glucose

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Journal of Surfactants and Detergents

Abstract

The surface and self-aggregation properties in water of a new series of amphiphilic homologues, bis-benzimidazolone derivatives of d-glucose, were investigated. Parameters such as the maximal surface excess concentration, minimal area per molecule at the interface, and critical micelle concentration (CMC) were found to be significantly dependent on the hydrophobic alkyl chain length. The synthesized compounds form micelles at remarkably low concentrations, and CMCs derived from surface tension measurements show a minimum as a function of the alkyl chain length; this unusual trend can be attributed to the formation of submicellar aggregates in compounds with long alkyl chains, as evidenced from fluorescence probe spectroscopy data. At high surfactant concentrations, lyotropic liquid crystalline phases with hexagonal structure are formed. Small angle X-ray scattering measurements indicate that the characteristic nanoscopic lengths increase with water swelling and alkyl chain length.

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Acknowledgments

The authors thank Consejo Superior de Investigaciones Científicas (CSIC) and Centre National pour la Recherche Scientifique et Technique (CNRST) for research support within the frame of the bilateral cooperation program (P2007MA01). The authors are also grateful to the Ministerio de Ciencia e Innovación, Spain (Project CTQ2008-01979/BQU) for funding and Ana Maria Moreno (IQAC/CSIC) for her help in the experiments.

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Authors and Affiliations

  1. Laboratoire d’Agroressources et Génie des Procédés, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Morocco

    Brahim Lakhrissi & Loubna Lakhrissi

  2. Laboratoire de Chimie Hétérocyclique, Faculté des Sciences, Université Mohamed V, Rabat, Morocco

    Loubna Lakhrissi, Mohamed Massoui & El Mokhtar Essassi

  3. Institut de Química Avançada de Catalunya, Consejo Superior de Investigaciones Científicas (IQAC/CSIC), Jordi Girona, 18-26, 08034, Barcelona, Spain

    Francesc Comelles, Jordi Esquena, Conxita Solans & Carlos Rodríguez-Abreu

  4. CIBER de Bioingeniería, Biomateriales y Nanomedicina (CIBER-BBN), Barcelona, Spain

    Jordi Esquena, Conxita Solans & Carlos Rodríguez-Abreu

Authors
  1. Brahim Lakhrissi
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  2. Loubna Lakhrissi
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  3. Mohamed Massoui
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  4. El Mokhtar Essassi
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  5. Francesc Comelles
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  8. Carlos Rodríguez-Abreu
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Correspondence to Carlos Rodríguez-Abreu.

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Lakhrissi, B., Lakhrissi, L., Massoui, M. et al. Surface and Self-Aggregation Properties of Bis-Benzimidazolones Derivatives of d-Glucose. J Surfact Deterg 13, 329–338 (2010). https://doi.org/10.1007/s11743-010-1183-x

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  • DOI: https://doi.org/10.1007/s11743-010-1183-x

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