Novel eugenol-based allyl-terminated precursors and their bio-based polymer networks through thiol-ene click reaction

Abstract

The design of biobased allyl-terminated precursors with high renewable carbon content for the construction of the thiol-ene polymer networks is essential for sustainable development and green society. In this work, a series of allyl-terminated precursors were synthesized from renewable eugenol and aliphatic diols through a two-step procedure. Then, the alternating aliphatic-aromatic thiol-ene polymer networks with tunable flexibility, thermal and mechanical properties were constructed via solvent-free thiol-ene click photopolymerization. The results showed that the thermal-physical and mechanical properties of the resulting polymers improved with the decrease of the carbon length of the aliphatic diols and the increase of thiol functionality. The thiol-ene polymers exhibited high tensile strength of 22.12 MPa and elongation at break of 126 %. All the polymer networks are thermally stable without obvious weight loss (T5%) up to 270 °C. All the polymers exhibited excellent solvent resistance in alkaline solution, acid solution natural solution brine, water and ethanol solvent. This work successfully provided a facile and simple method to develop biobased ally compounds from eugenol and high-performance polymer networks with tunable performance.