Acrylophosphonic acid reactivity with calcium ions and biological apatite.

OBJECTIVES: Acrylophosphonic acid (H(2)L) was reacted with biological apatite originating from dental enamel powder in order to identify and study the reaction products formed during the use of self-etch monomers. Nuclear magnetic resonance spectroscopy (NMR) showed the formation of brushite and a calcium salt of acrylophosphonic acid. This Ca salt was further synthesized and characterized by NMR, Fourier transform-infrared (FT-IR) and chromatography coupled with potentiometric analysis. The results reveal that calcium ions form a compound with two mono-deprotonated acrylophosphonate anions at physiological pH values. Thus, dissolution of the biological apatite by the acid-etch releases phosphate and calcium ions that combine to form brushite. The remaining dissolved Ca neutralize the acrylophosphonic acid to form an ionic salt of formula Ca(HL)(2). SIGNIFICANCE: The stoichiometry of this calcium salt allows us to conclude that, following a self-etch procedure, dissolved Ca ions participate in the formation of crosslinks in the complex photopolymerized copolymer composite network of the hybrid layer.