1. Department of Chemistry, Bogazici University, , 34342, Istanbul, Turkey;2. Faculty of Dentistry, Marmara University, , 34365 Nisantasi, Istanbul, Turkey
Abstract:
Five novel methacrylates containing either bisphosphonate ( 1 and 2 ), bisphosphonic acid (3), carboxylic acid (4) , or both bisphosphonic and carboxylic acid together (5) , are synthesized. The monomers 1 and 2 are synthesized by the reactions of tetraethyl 1‐hydroxyethane‐1,1‐diyldiphosphonate with ethyl α‐bromomethacrylate and tert‐butyl α‐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.
