Protecting-group-free synthesis of functional Poly(ester amide)s by the polyaddition of Bis(aziridine)s

Abstract

The protecting-group-free synthesis of reactive functional group containing poly(ester amide)s (PEAs) is reported. The synthesis of the PEAs is based on the nucleophilic ring-opening polyaddition of terephthalaziridine (TP-Az) with comonomers baring carboxylic acid and phenols as nucleophiles. The comonomers also contained the reactive functional groups aldehyde, ketone, ester, alcohol, furan, disulfide and siloxane, which were incorporated into the resulting PEAs without any detectable side reactions. A multicomponent polymerization was conducted to further demonstrate the versatility of this method. These PEAs are amorphous with high thermal stability (Td,5 %: 231–324 °C) and a have wide range of glass transition temperatures (Tg) (32–142 °C). The disulfide and siloxane-containing copolymers PEAs selectively degrade in the presence of dithiothreitol and fluoride respectively. The PEAs also underwent alkaline hydrolysis to yield a potential TP-Az, potentially facilitating chemical recycling of these PEAs.