Multifunctional deoxybenzoins: Preparation of low heat release polymer networks by orthogonal crosslinking

Abstract

Multifunctional epoxide monomers present opportunities to design cross-linked networks with conveniently tunable thermal and mechanical properties. This paper describes the synthesis of a novel, multifunctional deoxybenzoin monomer containing both epoxide and allyl groups, and its use in the preparation of epoxide networks. The orthogonal reactivity of these functional groups, operating via epoxide-amine and thiol-ene chemistry, facilitated the formation of networks with tunable glass transition temperatures and crosslink densities. Thermogravimetric analysis (TGA) and microscale combustion calorimetry (MCC) characterization revealed these networks to possess impressively low heat release properties (∼50% lower than conventional bisphenol A (BPA)-based networks) and very high char residues that reached ∼60%. Overall, introducing functional deoxybenzoin epoxide monomers into these types of network architectures imparts a method for combining low heat release structures with the advantageously tunable physical and mechanical properties of polymer networks.