Synthesis and photopolymerizations of first monomers with phosphonate and bisphosphonate or phosphonic and bisphosphonic acid functionalities for potential dental applications |
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Authors: | Turkan Gencoglu Fatma Demir Duman Keziban Olcay Havva Yagci Acar Duygu Avci |
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Institution: | 1. Department of Chemistry, Bogazici University, 34342 Bebek, Istanbul, Turkey;2. Department of Chemistry, Koc University, Rumelifeneri Yolu, 34450 Sariyer, Istanbul, Turkey;3. Department of Endodontics, Istanbul Medipol University, 34083 Fatih, Istanbul, Turkey |
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Abstract: | The first monomers containing both phosphonate and bisphosphonate (M1) or phosphonic and bisphosphonic acid (M2) functionalities are synthesized, aiming to improve binding abilities of self-etching adhesive systems and composites: An amine having both phosphonate and bisphosphonate functionalities is prepared via Michael addition reaction between diethyl (6-aminohexyl)phosphonate and tetraethyl vinylidene bisphosphonate, its reaction with 2-isocyanatoethyl methacrylate gives M1 which is converted to M2 by selective dealkylation of the phosphonate/bisphosphonate ester groups. Their copolymerization with commercial dental monomers (bisphenol A glycidyl methacrylate, triethylene glycol dimethacrylate, and 2-hydroxyethyl methacrylate) investigated by photo-differential scanning calorimetry shows adequate photopolymerization rate and conversion. X-ray diffraction, Fourier transform infrared, and X-ray photoelectron spectroscopy analyses of M2-treated hydroxyapatite particles show formation of stable M2-calcium salts. These monomers are assessed to be not toxic according to MTT standards by in vitro cytotoxicity studies with NIH 3T3, U2OS, and Saos-2 cells. All these properties make these monomers potential candidates as biocompatible components for dental adhesives and composites. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 2739–2751 |
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Keywords: | bisphosphonic acid dental adhesive hydroxyapatite photopolymerization phosphonate |
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