Eugenol derivatives immobilized in auto-polymerizing formulations as an approach to avoid inhibition interferences and improve biofunctionality in dental and orthopedic cements

Auto-polymerizing formulations based on poly(ethyl methacrylate) (PEMA) and eugenol derivatives are reported for dental and orthopedic applications. Spherical beads of PEMA were used as the pre-polymer powder and mixed with combinations of ethyl methacrylate and eugenyl methacrylate (EgMA) or ethoxyeugenyl methacrylate (EEgMA). A range of concentrations from 10 to 30 wt.% of EgMA or EEgMA were used to impart bioactivity properties to the cements. Increasing concentrations of the eugenol derivatives decreased the maximum polymerization temperatures from 69 to 37 °C without altering the working or setting time. At concentrations of 10 and 15 wt.% of EgMA or EEgMA a noticeable increase in the compressive (8%), flexural (40%) and tensile (24%) strengths were recorded in comparison to the control cements containing PEMA/ethyl methacrylate only. In addition to the improvement in mechanical properties the cements yielded a slightly crosslinked network due to the participation of the allylic group present in the eugenol derivatives, the presence of which has an intrinsically bactericidal effect against Escherichia coli and Streptococcus mutans strains, as reported in a previous study, thus enhancing the properties of the cements.