Adsorption of 4-Methacryloxyethyl Trimellitate Anhydride (4-META) on Hydroxyapatite and its Role in Composite Bonding

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Abstract
The adsorption of 4-methacryloxyethyl trimellitate anhydride (4-META) was studied from ethanol and dichloromethane onto synthetic hydroxyapatite (containing about 1.5 monolayers of physisorbed water) in order to study its role in restorative composite bonding to teeth. The adsorption lsotherm of 4-META was S-shaped and reversible from ethanol, and followed the Langmuir plot at lower concentrations. The isotherm was irreversible from dichloromethane, and a constant amount of adsorbate was removed from the solutions above a certain concentration. The irreversibly adsorbed compound was completely removed by washing with ethanol. Therefore, the bonding between teeth and the restorative resin containing 4-META as a coupling agent is micromechanical and not chemical in nature. An analysis of isotherms showed that the benzene rings of the adsorbate molecules lie flat on the surface for both solvents. The molecules adsorbed from ethanol rotate about the solvent-modified (esterified) or unmodified carboxylic anhydride moieties with methacrylate hydrocarbon groups which are folded upward. However, the molecules adsorbed from dichloromethane remain fixed to the surface without rotation, and their methacryloxyethyl groups are folded over the rings. The diametral tensile strength of a BIS-GMA polymer with adsorbate-covered apatite was approximately equal to that of the composite filled with untreated apatite.