Three novel dental monomers containing phosphonic acid groups (1a and 2a, based on diethyl amino(phenyl)methylphosphonate and 3a based on diethyl 1-aminoheptylphosphonate) were synthesized in two steps: the reaction of a-aminophosphonates with acryloyl chloride (for monomers 1a and 3a) or methacryloyl chloride (for 2a) to give monomers with phosphonate groups, and the hydrolysis of phosphonate groups by using trimethyl silylbromide. Their (and the intermediates') structures were confirmed by FTIR, 1 H, 13 C, and 31 P NMR spectroscopy. All the monomers dissolve well in water (1
The synthesis and polymerizations of four novel bisphosphonate-containing monomers are reported. The monomers were synthesized from reaction of ethyl and tert-butyl α-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 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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.