Furandiacylazide: A Biomass-Derived Versatile Polymer Platform toward Photodegradable and Nonflammable Polyurethanes

The development of a biomass-based polymer platform has become increasingly important to address environmental problems. In the present study, we present a furan-based polymer platform, furandiacylazide (FDAz), which can undergo a thermal Curtius rearrangement to produce a diisocyanate intermediate. Poly(furanyl-urethane-isocyanurate)s (PFUIs) were successfully formed via in situ polymerization of FDAz with various diols. Interestingly, by introducing an ortho-nitro group containing phenylene, a photodegradable polyurethane was easily synthesized. Tuning the polymerization conditions enabled control of the relative ratios of the urethane and isocyanurate moieties. Remarkably, a fully isocyanurate-containing polymer of isocyanates was successfully prepared through trimerization and was found to exhibit good heat resistance. FDAz is indeed a versatile polymer platform that can be applied to the synthesis of various eco-friendly functional polymers, potentially useful for the development of degradable plastics and nonflammable polymers.