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

Abstract

The 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 S(N)2 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 degrees C to generate furan-terminated polybutadiene (FTPB) and bismaleimide that were identified by H-1 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 degrees C will help widen the scope of the use of such materials.