Synthesis and radical polymerization of hydrolytically stable dentin bonding agents

Acrylic groups containing phosphonic acids were synthesized by ether format ion of ethyl alpha -chloromethylacrylate with hydroxyalkyl phosphonates and subsequent hydrolysis to the corresponding phosphonic acid alpha -methylsu bstituted acrylates, Furthermore, phosphonic acids derived from acrylonitri le and acrylamide were synthesized. The monomers are hydrolytically stable in aqueous ethanol. The radical polymerization of the monofunctional phosph onic acids results in water soluble polymers, whereas in case of a phosphon ic acid diacrylate a cross-linked polymer was formed. The most radical poly merizable phosphonic acids can be used to promote the adhesion to dentin.