Novel Bisphosphonated Methacrylates: Synthesis, Polymerizations, and Interactions with Hydroxyapatite

Bilgici Z. S. , Türker Ş. B. , Avcı Semiz D.

MACROMOLECULAR CHEMISTRY AND PHYSICS, cilt.214, ss.2324-2335, 2013 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 214
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1002/macp.201300381
  • Sayfa Sayıları: ss.2324-2335


Five novel methacrylates containing either bisphosphonate (1 and 2), bisphosphonic acid (3), carboxylic acid (4), or both bisphosphonic andcarboxylic acid together (5), are synthesized. The monomers 1 and 2 are synthesized by the reactions of tetraethyl 1-hydroxyethane-1,1-diyldiphosphonate with ethyl -bromomethacrylate and tert-butyl -bromomethacrylate; the same procedure fails with tetraethyl hydroxy(phenyl)methylenediphosphonate. 1 is converted to 3 by hydrolysis with trimethylsilyl bromide (TMSBr), and 2 is converted to 4 by hydrolysis with trifluoroacetic acid (TFA). Monomer 5 is obtained by hydrolysis of 2 first with TMSBr and then with TFA. The hydrolytic stability, the properties of the copolymerizations with commercial dental monomers, and HAP interactions make these monomers promising candidates for dental adhesives.