Epoxy resin systems
(ERSs) are a class of thermosetting
resins
that become thermostable and insoluble polymers upon curing. They
are widely used as components of protective surfaces, adhesives, and
paints and in the manufacturing of composites in the plastics industry.
The diglycidyl ether of bisphenol A (DGEBA) is used in 75–90%
of ERSs and is thus by far the most used epoxy resin monomer (ERM).
Unfortunately, DGEBA is a strong skin sensitizer and it is one of
the most common causes of occupational contact dermatitis. Furthermore,
DGEBA is synthesized from bisphenol A (BPA), which is a petroleum-derived
chemical with endocrine-disruptive properties. In this work, we have
used isosorbide, a renewable and nontoxic sugar-based material, as
an alternative to BPA in the design of ERMs. Three different bis-epoxide
isosorbide derivatives were synthesized: the diglycidyl ether of isosorbide
(1) and two novel isosorbide-based bis-epoxides containing
either a benzoic ester (2) or a benzyl ether linkage
(3). Assessment of the in vivo sensitizing potency of
the isosorbide bis-epoxides in the murine local lymph node assay (LLNA)
showed that all three compounds were significantly less sensitizing
than DGEBA, especially 2 which was nonsensitizing up
to 25% w/v. The peptide reactivity showed the same order of reactivity
as the LLNA, i.e., 2 being the least reactive, followed
by 3 and then 1, which displayed similar
peptide reactivity as DGEBA. Skin permeation of 2 and 3 was compared to DGEBA using ex vivo pig skin and static
Franz cells. The preliminary investigations of the technical properties
of the polymers formed from 1–3 were
promising. Although further investigations of the technical properties
are needed, all isosorbide bis-epoxides have the potential to be less
sensitizing renewable replacements of DGEBA, especially 2 that had the lowest sensitizing potency in vivo as well as the lowest
peptide reactivity.