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Synthesis of methacrylate-functionalized phosphonates and phosphates with long alkyl-chain spacers and their self-aggregation in aqueous solutions

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Abstract

Polymerizable amphiphilic organophosphorous compounds were synthesized and their self-aggregation behavior was investigated. The studied molecules contain a hydrophilic phosphorus end group, an alkyl chain spacer with a variable length from 3 to 11 CH2 groups and a polymerizable methacrylic group at the other chain end. Thus, the molecules represent a class of polymerizable surfactants. Two different reaction methods were used; either unsaturated alcohols or bromine-containing alcohols were applied as starting compounds for the preparation of the organophosphorous surfactants. The self-aggregation and micelle formation of the prepared compounds were investigated in aqueous solution by dynamic light scattering measurements. The critical micelle concentration of the P-containing amphiphiles was in all cases smaller than 0.040 mol/l and strongly dependent on the polarity of the phorphorous head group and the chain length of the spacer.

Graphical abstract

The synthesis of organophosphorous amphiphiles as surface active monomers for the modification of metal oxide surfaces is presented. The spacer between the phosphorous head group and the methacrylate group was varied with regard to their length and composition. The self-aggregation behavior of these methacrylate-functionalized phosphates and phosphonates surfactants was investigated.

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Acknowledgments

We thank the Austrian Nanoinitiative (project no. N1001) for financial support of this work.

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Authors and Affiliations

  1. Institute of Materials Chemistry, Vienna University of Technology, Getreidemarkt 9-165, 1060, Vienna, Austria

    Denisa Francová & Guido Kickelbick

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  1. Denisa Francová
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  2. Guido Kickelbick
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Correspondence to Guido Kickelbick.

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Francová, D., Kickelbick, G. Synthesis of methacrylate-functionalized phosphonates and phosphates with long alkyl-chain spacers and their self-aggregation in aqueous solutions. Monatsh Chem 140, 413–422 (2009). https://doi.org/10.1007/s00706-008-0045-y

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  • DOI: https://doi.org/10.1007/s00706-008-0045-y

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