Synthesis and polymerizations of novel bisphosphonate-containing methacrylates derived from alkyl alpha-hydroxymethacrylates

The synthesis and polymerizations of four novel bisphosphonate-containing monomers are reported. The monomers were synthesized from reaction of ethyl and tert-butyl alpha-bromomethacrylates with 3,3-bis(diethoxyphosphoryl)propanoic acid or with tetraethyl 4-hydroxybutane-1,1-diyldiphosphonate. Their thermal bulk polymerizations, photopolymerizations and copolymerizations with poly(ethylene glycol) methyl ether methacrylate were investigated. The homopolymerizations resulted in polymers with (M) over bar (n) values of 25 000-83 000 g mol(-1); the copolymerizations yielded soluble polymers with 22-34% incorporation of the new monomers; the photopolymerizations gave some structure-reactivity correlation; and one of the homopolymers, upon hydrolysis of its bisphosphonate groups, could interact with hydroxyapatite. (C) 2013 Society of Chemical Industry