Synthesis and evaluation of new dental monomers with both phosphonic and carboxylic acid functional groups

Abstract

Novel dental monomers containing both phosphonic and carboxylic acid functional groups were prepared. The monomers were based on t‐butyl α‐bromomethacrylate (t‐BuBMA) and synthesized in three steps: The reaction of o‐hydroxyaryl phosphonates [diethyl (2‐hydroxyphenyl) phosphonate, tetraethyl (2,5‐dihydroxy‐1,4‐phenylene) diphosphonate and tetraethyl 5,5′‐(propane‐2,2‐diyl)bis(2‐hydroxy‐5,1‐ phenylene) diphosphonate] with t‐BuBMA, the hydrolysis of phosphonate groups to phosphonic acid using trimethyl silylbromide, and the hydrolysis of the t‐butyl groups to carboxylic acid with trifluoroacetic acid. The monomers were solids and soluble in water and ethanol. The structures of the monomers were determined by Fourier transform infrared (FTIR), 1H, 13C, and 31P nuclear magnetic resonance (NMR) spectroscopy. The copolymerization behaviors of the synthesized monomers with glycerol dimethacrylate were first investigated in bulk using photodifferential scanning calorimetry at 40 °C with 2,2′‐dimethoxy‐2‐phenyl acetophenone as photoinitiator. Then, the solution copolymerization of the monomers with acrylamide in ethanol and water was studied, indicating that the synthesized monomers are incorporated into the copolymers. The acidic nature of the aqueous solutions of these monomers (pH values 1.72–1.87) is expected to give them etching properties important for dental applications. The interaction of the monomers with hydroxyapatite was investigated using 13C NMR and FTIR techniques. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1953–1965, 2009

Prefabricated Composite Resin Veneers – A Clinical Review

“…The high bond strengths obtained between the Componeer intaglio surface and the respective hybrid composite may be a result of two mechanisms: – A strong adsorbed layer of polymer material forms on the intaglio surface. This adsorption is a consequence of an initial increase in the ionization rate of the carboxylic groups in One Coat Bond because of the production of acid via the photoinitiator – Residual reactive methacrylate functionalities on the intaglio surface may form a network with the bonding agent after polymerization, which, along with the wetting characteristics of 2‐hydroxyethyl methacrylate in One Coat Bond, may explain the relatively high bond strengths associated with the adhesive joint formed by the prefabricated veneer, the dentin adhesive, and the direct hybrid composite resin. …”

“…– A strong adsorbed layer of polymer material forms on the intaglio surface. This adsorption is a consequence of an initial increase in the ionization rate of the carboxylic groups in One Coat Bond because of the production of acid via the photoinitiator …”

New polymer‐chemical developments in clinical dental polymer materials: Enamel–dentin adhesives and restorative composites

“…A number of new polymerizable PA (meth)acrylates for dental application were synthesized by the group of Avci. [36][37][38][39] Examples are aryl diphosphonic acid group-containing dimethacrylates such as 2,5-bis(methacryloyloxy)-1,4-phenylenediphosphonic acid (PA-1) or 2,2-bis[3-(dihydroxyphosphoryl)-4-(2carboxyprop-2-en-oxy)phenyl]propane (PA-3, Scheme 11). Both monomers are high melting solids and their decomposition starts near 200 C. This is a drawback for dental application, because such solids generally show a relatively low solubility, and solutions of these monomers tend to crystallize during storage.…”

Patient‐reported outcome measures suitable to assessment of patient navigation

“…A number of new polymerizable PA (meth)acrylates for dental application were synthesized by the group of Avci 36–39. Examples are aryl diphosphonic acid group‐containing dimethacrylates such as 2,5‐bis(methacryloyloxy)‐1,4‐phenylenediphosphonic acid (PA‐1) or 2,2‐bis[3‐(dihydroxyphosphoryl)‐4‐(2‐carboxyprop‐2‐en‐oxy)phenyl]propane (PA‐3, Scheme ).…”