A Versatile Synthetic Route to Phosphonate-Functional Monomers, Oligomers, Silanes, and Hybrid Nanoparticles

Abstract

The highly selective single Michael addition of diethyl vinylphosphonate to alkylamines represents a very versatile synthetic route affording a large variety of novel multifunctional phosphonates including aminoalkylphosphonates, phosphonate functional silanes, and phosphonate-functionalized acrylic monomers. The hydrolysis of the phosphonate group results in a phosphonic acid functional monomer which can be used as component of dental composites exhibiting improved filler−matrix interaction. The sol−gel reaction of the phosphonate-functional silanes produced novel phosphonate-functional organic/inorganic hybrid nanoparticles with particle sizes ranging from 30 to 100 nm.