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Biobased isosorbide methacrylate monomer as an alternative to bisphenol A glycerolate dimethacrylate for dental restorative applications
Author(s) -
Berlanga Duarte María Lydia,
Reyna Medina Luis Alberto,
Reyes Patricia Torres,
González Pérez Sergio Emmanuel,
Herrera González Ana María
Publication year - 2017
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.44591
Subject(s) - isosorbide , methacrylate , bisphenol a , monomer , materials science , polymer chemistry , polymer science , chemical engineering , chemistry , organic chemistry , composite material , polymer , epoxy , engineering
In this study, a new biobased isosorbide urethane methacrylic monomer [isosorbide‐derived urethane dimethacrylate (Is‐UDMA)] was evaluated as a replacement for currently used bisphenol A glycerolate dimethacrylate (Bis‐GMA) based dental restorative materials. Dental composites were prepared at different Is‐UDMA and Bis‐GMA concentrations. For these composites, the photocuring kinetics, volumetric shrinkage, viscoelastic properties, water sorption, and solubility were evaluated. The photocuring kinetics, followed by real‐time IR spectroscopy, showed higher double‐bond conversion (DC) values for the formulations containing the Is‐UDMA monomer; the highest DC (82%) was achieved by the formulation prepared with only the Is‐UDMA monomer. The volumetric shrinkage was reduced to 23.7% as compared with the dental resin formulated with Bis‐GMA. The viscoelastic properties of the formulations containing both Is‐UDMA and Bis‐GMA monomers in a 50:50 composition were superior to the rest of the tested formulations, including those prepared with pure polymers. This behavior was explained in terms of a compromise between crosslinking and rigidity (or flexibility) of the resulting polymer network. A preliminary test on microleakage in a dental enamel demonstrated that the new Is‐UDMA monomer is a potential replacement for the Bis‐GMA monomer in dental restorative materials. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 44591.