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

Abstract

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. [GRAPHICS] .