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Calix[4]arene-tetranitrone as crosslinker in dental composite materials

Authors

  • Monir Tabatabai,

    1. Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstraße 1, 40225 Düsseldorf, Germany
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  • Bernd Garska,

    1. Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstraße 1, 40225 Düsseldorf, Germany
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  • Norbert Moszner,

    1. Ivoclar Vivadent AG, Bendererstrasse 2, 9494 Schaan, Principality of Liechtenstein
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  • Andreas Utterodt,

    1. Heraeus Kulzer GmbH, Philipp-Reis-Straße 8, 61273 Wehrheim, Germany
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  • Helmut Ritter

    Corresponding author
    1. Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstraße 1, 40225 Düsseldorf, Germany
    • Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstraße 1, 40225 Düsseldorf, Germany.
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Abstract

The synthesis of a functionalized calix[4]arene bearing 1,3-dipolaric nitrone groups (5) has been carried out. The reaction of N-methylhydroxylamine or N-propylhydroxylamine with the carbonyl group of 5,11,7,23-tetraformyl-25,26,27,28-tetraalkoxycalix[4]arene leads to calix[4]arenes bearing a nitrone function at each of the four para-positions. Via 1,3-dipolar cyclo-addition of acrylic acid methyl ester with the nitrone functions of 5, subsequently an upper rim-substituted tetraisoxalidinecalix[4]arene is quantitatively synthesized. Further, the minimization of shrinkage of a dental filling depending on the amount of calix[4]arene-tetranitrone is discussed. Copyright © 2011 Society of Chemical Industry

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