Synthesis and Characterization of Photocurable Difunctional Monomers for Medical Applications

Abstract

Photocurable materials offer a rapid transition from a liquid to a solid state, and have recently received great interest in the medical field. However, while dental resins are very popular, only a few materials have been developed for soft tissue repair. This study aims to synthesize a difunctional methacrylate monomer using a dibutyltin dilaurate which is suitable for the photocuring of soft materials. These soft materials were compared with PhotoBioCure® (Szczecin, Poland) material with a similar molecular weight, of Mn ~7000 g/mol on average. Infrared spectroscopy was used to monitor the two-step synthesis catalyzed with dibutyltin dilaurate, while spectroscopic and chromatographic methods were used to determine the chemical structure and molecular weight of the monomers. Photopolymerization kinetics under varying light intensities were explored in a nitrogen atmosphere for representative difunctional monomers. The mechanical testing of the resulting elastomeric films confirmed tensile strength and modulus values consistent with soft tissue parameters in the range of 3–4 MPa. The 3D printability of the macromonomers was also assessed. Additionally, cytotoxicity assessments using cultured cells showed a high cell viability (97%) for all new materials. Overall, we demonstrate that difunctional methacrylate monomers converted to flexible solids during photopolymerization show great potential for biomedical applications.