Synthesis, Characterization and Evaluation of Urethane Derivatives of Bis-GMA

Published

September 1, 2000

Author(s)

C A. Khatri, J W. Stansbury, Carl R. Schultesiz, Joseph M. Antonucci

Abstract

The dimethacrylate monomer designated as Bis-GMA ushered in the modern era of polymeric dental restorative, sealant and adhesive materials. Because of its high viscosity, primarily due to the strong hydrogen bond interactions arising from its two hydroxyl groups, Bis-GMA is commonly used with a diluent monomer of much smaller size, e.g., triethyleneglycol dimethacrylate. The major objective of this study was to synthesize urethane derivatives of Bis-GMA by reacting these hydroxyl groups with alkyl isocyanates in an attempt to prepare by facile means less viscous analogs of Bid-GMA. Specifically, Bis-GMA was reacted with stoichiometric amounts of ethyl, propyl, butyl, hexyl and octyl isocyanates. These urethane modified Bis-GMAs exhibited significantly lower viscosities and water uptake than Bis-GMA. In addition, on polymerization these new monomers yielded highly converted thermoset polymers that had relatively low volume contraction. Support: NIST/NIDR Interagency Agreement Y1-DE-7006-0.

Proceedings Title

American Chemical Society; Division of Polymer Chemcistry, Meeting | | | American Chemical Society (ACS)

Volume

41

Issue

No. 2

Conference Dates

August 20-24, 2000

Conference Title

Polymer Preprints

Pub Type

Conferences

Download Paper

Local Download

Keywords

conversion, hydrophobicity, polymerization shrinkage, synthesis, urethane methacrylates, viscosity

Citation

Khatri, C. , Stansbury, J. , Schultesiz, C. and Antonucci, J. (2000), Synthesis, Characterization and Evaluation of Urethane Derivatives of Bis-GMA, American Chemical Society; Division of Polymer Chemcistry, Meeting | | | American Chemical Society (ACS), [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=851722 (Accessed June 1, 2024)