Epoxy resin monomers with reduced skin sensitizing potency

Chem Res Toxicol. 2014 Jun 16;27(6):1002-10. doi: 10.1021/tx5000624. Epub 2014 Jun 2.

Abstract

Epoxy resin monomers (ERMs), especially diglycidyl ethers of bisphenol A and F (DGEBA and DGEBF), are extensively used as building blocks for thermosetting polymers. However, they are known to commonly cause skin allergy. This research describes a number of alternative ERMs, designed with the aim of reducing the skin sensitizing potency while maintaining the ability to form thermosetting polymers. The compounds were designed, synthesized, and assessed for sensitizing potency using the in vivo murine local lymph node assay (LLNA). All six epoxy resin monomers had decreased sensitizing potencies compared to those of DGEBA and DGEBF. With respect to the LLNA EC3 value, the best of the alternative monomers had a value approximately 2.5 times higher than those of DGEBA and DGEBF. The diepoxides were reacted with triethylenetetramine, and the polymers formed were tested for technical applicability using thermogravimetric analysis and differential scanning calorimetry. Four out of the six alternative ERMs gave polymers with a thermal stability comparable to that obtained with DGEBA and DGEBF. The use of improved epoxy resin monomers with less skin sensitizing effects is a direct way to tackle the problem of contact allergy to epoxy resin systems, particularly in occupational settings, resulting in a reduction in the incidence of allergic contact dermatitis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Calorimetry
  • Epoxy Resins / chemical synthesis
  • Epoxy Resins / chemistry
  • Epoxy Resins / pharmacology*
  • Epoxy Resins / toxicity
  • Female
  • Local Lymph Node Assay
  • Lymph Nodes / drug effects*
  • Mice
  • Mice, Inbred CBA
  • Molecular Structure
  • Skin Tests
  • Thermogravimetry
  • Toxicity Tests

Substances

  • Epoxy Resins