Epoxy resin monomers with reduced skin sensitizing potency.
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.
Department of Chemistry and Molecular Biology, Dermatochemistry and Skin Allergy, University of Gothenburg , SE-412 96 Gothenburg, Sweden.
Niamh M
NM
O'Boyle
Ida B
IB
Niklasson
Ali R
AR
Tehrani-Bagha
Tamara
T
Delaine
Krister
K
Holmberg
Kristina
K
Luthman
Ann-Therese
AT
Karlberg
D000818:Animals; D002151:Calorimetry; D004853:Epoxy Resins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D005260:Female; D023441:Local Lymph Node Assay; D008198:Lymph Nodes / Q000187:drug effects*; D051379:Mice; D008808:Mice, Inbred CBA; D015394:Molecular Structure; D012882:Skin Tests; D013818:Thermogravimetry; D018675:Toxicity Tests
D004853:Epoxy Resins