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

J Biomed Mater Res. 1990 Jun;24(6):705-20. doi: 10.1002/jbm.820240606.

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 adhesion-promoting acrylated phosphonates are also discussed.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acrylates*
  • Adhesives*
  • Biocompatible Materials*
  • Dental Cements
  • Dentin
  • Humans
  • In Vitro Techniques
  • Materials Testing
  • Molecular Structure
  • Organophosphorus Compounds*

Substances

  • Acrylates
  • Adhesives
  • Biocompatible Materials
  • Dental Cements
  • Organophosphorus Compounds