Synthesis and characterization of a dimethacrylates monomer with low shrinkage and water sorption for dental application

In this study, a dimethacrylates monomer 1,3‐bis[2‐(4‐(2′‐hydroxy‐3′‐methacryloyloxy‐propoxy)phenyl)‐2propyl]benzene (BMPB) was synthesized to replace 2,2‐bis[4‐(2′‐hydroxy‐3′‐methacryloyloxy‐propoxy)phenyl]propane (Bis‐GMA) as one component of dental restorative material with the aim of reducing polymerization shrinkage and water sorption. The structure of BMPB was confirmed by FTIR, 1 H‐NMR, and elemental analysis. Double bond conversion, polymerization shrinkage, contact angle, water sorption, solubility, flexural strength, and flexural modulus of BMPB/tri(ethylene glycol) dimethacrylate (TEGDMA) based resin were measured. Bis‐GMA/TEGDMA based resin was used as reference. The results illustrated that double bond conversion, polymerization shrinkage, water sorption, and solubility of BMPB/TEGDMA were lower than that of Bis‐GMA/TEGDMA ( P < 0.05). BMPB/TEGDMA had the same flexural strength with Bis‐GMA/TEGDMA ( P > 0.05), but higher flexural modulus ( P < 0.05). Therefore, BMPB could possibly replace Bis‐GMA as one component of dental restorative materials with the advantages of similar mechanical properties, being slightly more hydrophobic but presenting less shrinkage. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012