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The aim of this work was to synthesize and investigate properties of a novel dimethacrylic monomer based on bioderived alicyclic diol—isosorbide. Its potential as a possible substitute of 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane (BISGMA), widely used in dental restorative materials and suspected for toxicity was assessed. The novel monomer was obtained in a three-step synthesis. First, isosorbide was etherified by a Williamson nucleophilic substitution and subsequently oxidized to isosorbide diglycidyl ether (ISDGE). A triphenyl phosphine catalyzed addition of methacrylic acid to ISDGE resulted in 2,5-bis(2-hydroxy-3-methacryloyloxypropoxy)- 1,4:3,6-dianhydro-sorbitol (ISDGMA). The monomer obtained was photopolymerized using camphorquinone/2-(dimethylamino)ethyl methacrylate initiating system. Next, compositions with triethylene glycol dimethacrylate (TEGDMA) were prepared and polymerized. Double bond conversion, polymerization shrinkage and water sorption of resulting polymers were determined. Selected mechanical (flexular strength and modulus, Brinell hardness) and thermomechanical (DMA analysis) properties were also investigated. BISGMA based materials were prepared as reference for comparison of particular properties.

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In this article, synthesis and properties of novel dimethacrylic resin (ISETDMA) based on human friendly, biobased isosorbide was described. Its potential as a possible diluting monomer for medical applications, mainly dental restorative systems was assessed. The resin was obtained in two-step synthesis including ethoxylation of isosorbide and subsequent methacrylation with methacryloyl chloride. 1 HNMR, FTIR, and electrospray ionization mass spectroscopy (ESI-MS) techniques were used to identify products. ISETDMA as well as composition with 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane were polymerized using UV initiator IRGACURE 651. Double bond conversion, polymerization shrinkage, water sorption, and sol fraction of resulting polymers were determined. Selected mechanical (flexural strength and modulus, Brinell hardness) and thermomechanical (dynamic mechanical analysis) properties were also investigated. Triethylene glycol dimethacrylate and 2,2-bis(4-(2-methacryloxyethyl-1-oxy)phenyl)propane based homopolymers and copolymers were prepared as reference for comparison of particular properties.