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Synthesis of main chain polymeric benzophenone photoinitiator via thiol-ene click chemistry and Its use in free radical polymerization

Authors

  • Gokhan Temel,

    Corresponding author
    1. Department of Polymer Engineering, Faculty of Engineering, Yalova University, Yalova 77100, Turkey
    2. Department of Chemistry, Yildiz Technical University, 34210 Davutpasa, Istanbul, Turkey
    • Department of Polymer Engineering, Faculty of Engineering, Yalova University, Yalova 77100, Turkey
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  • Nurcan Karaca,

    1. Department of Chemistry, Yildiz Technical University, 34210 Davutpasa, Istanbul, Turkey
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  • Nergis Arsu

    Corresponding author
    1. Department of Chemistry, Yildiz Technical University, 34210 Davutpasa, Istanbul, Turkey
    • Department of Chemistry, Yildiz Technical University, 34210 Davutpasa, Istanbul, Turkey
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Abstract

Main chain polymeric benzophenone photoinitiator (PBP) was synthesized by using “Thiol-ene Click Chemistry” and characterized with 1H NMR, FTIR, UV, and phosphorescence spectroscopies. PBP as a polymeric photoinitiator presented excellent absorption properties (ε294 = 28,300 mol−1L−1cm−1) compared to the molecular initiator BP (ε252 = 16,600 mol−1L−1cm−1). The triplet energy of PBP was obtained from the phosphorescence measurement in 2-methyl tetrahydrofurane at 77 K as 298.3 kJ/mol and according to phosphorescence lifetime, the lowest triplet state of PBP has an n-π* nature. Triplet–triplet absorption spectrum of PBP at 550 nm following laser excitation (355 nm) were recorded and triplet lifetime of PBP was found as 250 ns. The photoinitiation efficiency of PBP was determined for the polymerization of Hexanedioldiacrylate (HDDA) with PBP and BP in the presence of a coinitiator namely, N-methyldiethanolamine (MDEA) by Photo-DSC. The initiation efficiency of PBP for polymerization of HDDA is much higher than for the formulation consisting of BP. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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