Synthesis and analysis of thermally degradable polybutadiene containing Diels–Alder adduct

Abstract

AbstractThe thermoreversible Diels–Alder reaction, a type of stimuli‐responsive reversible organic reaction, is attractive because its direction can be easily controlled. In this study, the cross‐linked Diels–Alder adduct‐containing polybutadiene (DAPBD) was synthesized by the SN2 reaction of bromine‐terminated polybutadiene with a furan‐bismaleimide Diels–Alder adduct, and their thermodegradable behavior was analyzed by thermogravimetric analysis. DAPBD was dissociated by the retro‐Diels–Alder reaction and dissolved in chlorobenzene at 132 °C to generate furan‐terminated polybutadiene (FTPB) and bismaleimide that were identified by 1H NMR spectroscopy. This synthetic method using premade Diels–Alder adducts is expected to enhance the thermoreversibility of the materials by significantly increasing the concentration of the Diels–Alder adduct moieties in the final DAPBD. The polymerization performed at 35 °C will help widen the scope of the use of such materials.