The synthesis of three novel dimethacrylate esters for use as the monomer p
hase in dental composites was studied. The monomers were prepared by the re
action of glycidyl methacrylate with phthalic, isophthalic and terephthalic
acids, respectively, and the reaction products were found to be mixtures o
f isomers. The monomers obtained from the reaction of phthalic and isophtha
lic acids were low-viscosity liquids and the relationship between viscosity
and molecular structure was studied. The low viscosity of these di-hydroxy
l containing monomers was shown to be due to intramolecular hydrogen bondin
g. This reduced monomer viscosity compared with BisGMA allowed a reduction
in the quantity of diluent monomer triethyleneglycoldimethacrylate (TEGDMA)
required to give standard viscosities of 1 and 2 Pas resulting in a modest
decrease (ca. 10%) in polymerization shrinkage compared with that exhibite
d by BisGMA/TEGDMA solutions of equivalent viscosities. A number of propert
ies relevant to the use of these as potential core monomers in dental compo
sites were determined for both monomer and polymer systems. (C) 1998 Publis
hed by Elsevier Science Ltd. All rights reserved.