Synthesis and post-polymerisation modification of an epoxy-functional polycarbonate

Abstract

The synthesis of an epoxide-functional polycarbonate via the selective carbonate ring-opening polymerisation (ROP) of trimethylenepropane oxirane ether carbonate (TMOC) monomer was investigated using a range of organocatalysts. The catalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) provided the best polymerisation control without reacting with the epoxide functionality and the resulting polymers presented low dispersities and molecular weights close to that predicted from the monomer-to-initiator ratio. Subsequently, the post-polymerisation functionalisation of PTMOC through thiol–epoxy reactions was investigated using a series of thiols and showed to be effective especially for thiophenols. Finally, modification of PTMOC by ring-opening the epoxide with amines proved to be challenging as the conditions applied led to a degradation of the polymer backbone and/or formation of crosslinked materials.