Unveiling the Potential of Plant-Derived Diarylheptanoids and Their Derivatives in Bio-Based Polyurethane Compositions.

Abstract

The key challenge in polymer science is developing sustainable synthesis methods using renewable feedstocks. This study explores plant-derived diarylheptanoids with various structures as the building blocks for polyurethane (PU) materials. Diarylheptanoid glucosides isolated from black alder (Alnus glutinosa) bark were hydrolyzed and fractionated to remove sugar moieties. The resulting diarylheptanoids, along with unhydrolyzed analogues and curcumin, were used as biomass-based polyols to synthesize model PU films. Incorporating diarylheptanoids enhanced the mechanical strength and reduced the flexibility of PU due to increased crosslinking, with effects proportional to the OH functionality of the biomass-based polyols. Weight loss, FTIR, and Py-GC-MS/FID analyses revealed that the catechol moieties and the glucosidic bonds are biodegradable structural subunits of diarylheptanoids incorporated into PU films. Rigid polyurethane foams (PURs) incorporating high-OH-functionality diarylheptanoid glucosides such as oregonin demonstrated significantly higher compression strength and less weight loss during non-isothermal thermal analysis in air compared to those of commercial polyol-based foams. A cone calorimeter test showed that the PUR foam with diarylheptanoid derivatives had a lower degradation rate, a longer flame-burning time, 30% less heat emission, and 25% less smoke, indicating improved flame retardancy. Adding 1-2% oregonin-enriched black alder bark extracts to commercial Elastopir 1132/509/0 PUR foam significantly improved its resistance to thermal oxidative aging, outperforming the commercial antioxidant Irganox.