Hydrophobically modified isosorbide dimethacrylates as a bisphenol-A (BPA)-free dental filling material

Bilal Marie, Raymond Clark, Tim Gillece, Seher Ozkan, Michael Jaffe, Nuggehalli M. Ravindra

Research output: Contribution to journalArticlepeer-review

Abstract

A series of bio-based hydrophobically modified isosorbide dimethacrylates, with para-, meta-, and ortho-benzoate aromatic spacers (ISBGBMA), are synthesized, characterized, and evaluated as potential dental restorative resins. The new monomers, isosorbide 2,5-bis(4-glyceryloxybenzoate) dimethacrylate (ISB4GBMA), isosorbide 2,5-bis(3-glyceryloxybenzoate) dimethacrylate (ISB3GBMA), and isosorbide 2,5-bis(2-glyceryloxybenzoate) dimethacrylate (ISB2GBMA), are mixed with triethylene glycol dimethacrylate (TEGDMA) and photopolymerized. The resulting polymers are evaluated for the degree of monomeric conversion, polymerization shrinkage, water sorption, glass transition temperature, and flexural strength. Isosorbide glycerolate dimethacrylate (ISDGMA) is synthesized, and Bisphenol A glycerolate dimethacrylate (BisGMA) is prepared, and both are evaluated as a reference. Poly(ISBGBMA/TEGDMA) series shows lower water sorption (39–44 µg/mm3) over Poly(ISDGMA/TEGDMA) (73 µg/mm3) but higher than Poly(BisGMA/TEGDMA) (26 µg/mm3). Flexural strength is higher for Poly(ISBGBMA/TEGDMA) series (37–45 MPa) over Poly(ISDGMA/ TEGDMA) (10 MPa) and less than Poly(BisGMA/TEGDMA) (53 MPa) after immersion in phosphatebuffered saline (DPBS) for 24 h. Poly(ISB2GBMA/TEGDMA) has the highest glass transition temperature at 85C, and its monomeric mixture has the lowest viscosity at 0.62 Pa·s, among the (ISBGBMA/TEGDMA) polymers and monomer mixtures. Collectively, this data suggests that the ortho ISBGBMA monomer is a potential bio-based, BPA-free replacement for BisGMA, and could be the focus for future study.

Original languageEnglish (US)
Article number2139
JournalMaterials
Volume14
Issue number9
DOIs
StatePublished - May 1 2021

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics

Keywords

  • Bio-based
  • Bisphenol-A (BPA)
  • Dental filling material
  • Hydrophobic
  • Isosorbide dimethacrylates

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