Hydroperoxidation of EPDM rubber using singlet oxygen: Synthesis and grafting studies



Chemically generated singlet oxygen hydroperoxidizes the ethylidene double bond in terpolymers of ethylene, propylene, and ethylidene norbornene (EPDM rubber). The EPDM–hydroperoxide was reduced exclusively to 2-(1-hydroxylethyl)-norborene-EPDM rubber using either triphenylphosphine or sodium sulfite. Thermal decomposition of EPDM–hydroperoxide in the presence of either methyl methacrylate or 2- or 4-vinyl pyridine free radically grafted these monomers to the rubber. In the absence of graftable monomer, however, thermal decomposition of EPDM-hydroperoxide generated an intractable polyether.