Preparation and evaluation of (R)-(-)-carvone-doped polymeric resins as potential antibacterial dental materials.

OBJECTIVES: This study aimed to develop and evaluate resin-based antibacterial materials incorporating carvone for restorative dentistry. The objectives included assessing antimicrobial activity, conversion degree, mechanical properties, hydrolytic and hygroscopic behavior, cytotoxicity, among others. METHODOLOGY: Carvone was incorporated into resin-based materials following established protocols. Antimicrobial activity was evaluated against S. Aureus. Conversion degree, polimerization kinetics, mechanical properties, hydrolytic and hygroscopic behavior, cytotoxicity, and other properties were assessed using standardized tests and methodologies. RESULTS: Carvone-incorporated materials demonstrated significant antimicrobial activity, minimal changes in conversion degree, comparable mechanical properties, improved hydrolytic and hygroscopic behavior, and lack of cytotoxicity. Antimicrobial resins were obtained due to the hydrophobic nature of carvone and its ability to diffuse through the cell walls of microorganisms, causing membrane damage. The polymerization process yielded successful conversion, ensuring adequate material performance. SIGNIFICANCE: This study showcases that incorporating carvone into methacrylate-based resins can confer antimicrobial properties while preserving key material attributes. Antimicrobial activity against S. aureus is achieved without cytotoxicity in human fibroblasts. While flexural properties are affected only at carvone concentrations exceeding 9%, conversion degree and polymerization kinetics remain stable, except for a specific experimental formulation. These findings highlight the balanced integration of carvone. However, further work, including assessing antimicrobial performance against specific strains like S. Mutans and/or C. Albicans, and evaluating long-term effectiveness, is essential to establish the potential of these materials for dental restorations.

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique.

This study describes the synthesis of a curing agent derived from limonene as well as its application to prepare biobased thermoset polymers via the epoxy/thiol-ene photopolymerization (ETE) method. A biobased commercial epoxy resin was used to synthesize a crosslinked polymeric matrix of polyether-polythioether type. The preparation of the curing agent required two steps. First, a diamine intermediate was prepared by means of a thiol-ene coupling reaction between limonene and cysteamine hydrochloride. Second, the primary amino groups of the intermediate compound were alkylated using allyl bromide. The obtained ditertiary amine-functionalized limonene compound was purified and characterized by FTIR and NMR spectroscopies along with GC-MS. The curing agent was formulated with a tetrafunctional thiol in stoichiometric ratio, and a photoinitiator at 1 mol % concentration, as the components of a thiol-ene system (TES). Two formulations were prepared in which molar concentrations of 30 and 40 mol % of the TES were added to the epoxy resin. The kinetics of the ETE photopolymerizations were determined by means of Real-Time FTIR spectroscopy, which demonstrated high reactivity by observing photopolymerization rates in the range of 1.50-2.25 s-1 for the epoxy, double bonds and thiol groups. The obtained polymers were analyzed by thermal and thermo-mechanical techniques finding glass transition temperatures (Tg) of 60 °C and 52 °C for the polymers derived from the formulations with 30 mol % and 40 mol % of TES, respectively. Potential applications for these materials can be foreseen in the area of coatings.