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There is no doubt that nature offers an abundance of opportunities to polymer chemists for shaping structural and functional polymers in its wide variety of raw materials. Nowadays, plant oils and derivatives are in the spotlight of polyurethane technology and the design of novel biobased polyols derived from them is an active area of research. The contribution of this technology to sustainable development must go further than simply exploit renewable feedstock, and therefore must be aware of efficient click-chemistry transformations exemplified by thiol-ene/yne couplings. Within this contribution, these biobased materials, together with thiol-ene/yne couplings are presented as a perfect ecofriendly combination to prepare hydroxyl building blocks for polyurethane technology.

A family of supramolecular side-chain ionic polyurethanes (PUs) is synthesized by a simple method using polyurethanes with tertiary amines as pendant groups, and carboxylic acids. The resulting polyurethanes contain diethyl ammonium and carboxylate moieties that are bonded by a combination of ionic and hydrogen bonds. The self-assembling process is observed by Fourier-transform infrared spectroscopy-attenuated total reflection (FTIR-ATR) and nuclear magnetic resonance (NMR) spectroscopy. The synthesized polyurethanes are characterized by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Rheological, dielectric, and mechanical properties are investigated, and it is found that the tunability of the properties depends on the acid functionality and the chain length. Dynamic viscoelastic tests reveal a rapid and complete thermal reversibility, which opens the door to studying the recyclability of the samples.