Chemical degradation of amine-cured DGEBA epoxy resin in supercritical 1-propanol for recycling carbon fiber from composites

Chemical degradation of diglycidyl ether of bisphenol A (DGEBA) epoxy resin cured with an aliphatic amine in supercritical 1-propanol was investigated under different reaction temperature and time. The combination of GC-MS and LC-MS proved that the epoxy resin was decomposed to five main products including phenol, 4-isopropylphenol, 4-isopropenylphenol, bisphenol A, and 4,4′-(cyclopropane-1,1-diyl)diphenol. The 13 C-NMR results verified the chemical structures of the degradation products. The change of the products’ yield with time was evaluated by an effective means of HPLC. In addition, the GPC analysis confirmed the formation of soluble low molecular weight clusters during the degradation reaction. A possible free-radical reaction mechanism was proposed for chemical depolymerization of the epoxy resin in supercritical 1-propanol. After the homolytic cleavage of the aromatic ether linkages, the resulting bisphenol A biradical either produced 4,4′-(cyclopropane-1,1-diyl)diphenol after intramolecular rearrangement or generated bisphenol A after capturing hydrogen from 1-propanol.