Levoglucosenone to 3D-printed green materials: synthesizing sustainable and tunable monomers for eco-friendly photo-curing

Abstract

3D-printing technologies for polymer formulations are experiencing huge development due to the complex and specific geometries that can be created employing additive manufacturing. However, to ensure sustainable growth, it is essential to replace the currently used fossil-based resins with new bio-sourced alternatives. In this study, tunable bis-allylated compounds were efficiently synthesized from cellulose-derived levoglucosenone via a chemo-enzymatic pathway whose greenness has been assessed by E-factor and Eco-Scale. Subsequently, photocuring was employed as an eco-friendly process to polymerize these compounds with a trifunctional thiol using thiol–ene click chemistry. Real-time techniques such as FT-IR, photo-DSC, and photo-rheology were employed to extensively characterize the UV process. The resulting thermosets were also subjected to a thorough analysis, covering their thermo-mechanical properties and degradation. Owing to the exceptional reactivity of this thiol–ene system, 3-D printed materials were achieved with remarkable precision.