Acrylated phosphonate esters containing 1,3‐dioxane and 1,3‐dioxolane moieties as adhesion‐promoting agents for dentin and hard tissues, I

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Abstract
Novel acrylated phosphonate esters containing 1,3‐dioxane and 1,3‐dioxolane moieties derived from polyols such as glycerol, D‐mannitol, D‐sorbitol, pentaerythritol, and dipentaerythritol have been evaluated in vitro for their role as adhesion‐promoting agents in composites employed for restorative dentistry. Some of the acrylated phosphonate esters have been found to promote strong bonding to dentin; the dipentaerythritol derivative exhibits a bond strength of approximately 960 psi (7 MPa) which compares favorably to commercial dentin adhesive systems. The bonding agents appear to act in multifunctional ways: the phosphonate group of the monomer chelates the calcium ions of hydroxyapatite at the dentin surface, ethereal oxygen atoms of 1,3‐dioxolane or 1,3‐dioxane moieties interact with the proteinaceous content of collagen, and the methacrylic fragment copolymerizes concomitantly with the other comonomers of the restorative composite material. Methods of preparing radiopaque adhesionpromoting acrylated phosphonates are also discussed.