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Synthesis and Micellization Properties of New Anionic Reactive Surfactants Based on Hydrogenated Cardanol

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Journal of Surfactants and Detergents

Abstract

We report the synthesis, characterization and micellization properties of two anionic reactive surfactants based on 3-pentadecyl phenol obtainable from a renewable resource, cardanol. The synthesis is achieved through simple chemical transformations, first converting the phenol to the acrylate that is sulfonated in a second step. The products were characterized by elemental analysis and spectroscopic techniques. The surfactant properties of the sulfonated acrylates were measured and compared with the standard non-reactive anionic surfactant sodium dodecyl sulfonate. The micellization behavior of aqueous solutions was studied using conductivity, surface tension measurements, and the fluorescence probe technique based on diphenyl hexatriene. Characterization by surface tension measurements facilitated the determination of basic surfactant properties like the critical micelle concentration (CMC), the surface tension at the CMC, surface excess and area per surfactant molecule. The Gibbs free energy of micellization showed a negative value suggesting spontaneous micellization in aqueous solution. The micellization of the surfmer with an ethylene spacer between the phenyl ring and the acrylate group seems to be enhanced as indicated by the lower surface excess and lower free energy. Its CMC was also lower.

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Acknowledgments

This research was supported by a Marie Curie International Incoming Fellowship to Dr. K. I. Suresh within the 7th European Community Framework Programme (FP-7).

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Authors and Affiliations

  1. Institute for Macromolecular Chemistry, Stefan-Meier-Straße 31, 79104, Freiburg, Germany

    Suresh Kattimuttathu I & Eckhard Bartsch

  2. Department of Pharmaceutical Technology, University of Freiburg, Hermann-Herder-Straße 9, 79104, Freiburg, Germany

    Gesche Foerst & Rolf Schubert

  3. Organic Coatings and Polymers Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500 007, India

    Suresh Kattimuttathu I

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  1. Suresh Kattimuttathu I
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  2. Gesche Foerst
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  4. Eckhard Bartsch
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Correspondence to Suresh Kattimuttathu I.

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Kattimuttathu I, S., Foerst, G., Schubert, R. et al. Synthesis and Micellization Properties of New Anionic Reactive Surfactants Based on Hydrogenated Cardanol. J Surfact Deterg 15, 207–215 (2012). https://doi.org/10.1007/s11743-011-1294-z

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  • DOI: https://doi.org/10.1007/s11743-011-1294-z

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