Synthesis, Characterization, and Proton Conductivity of Muconic Acid-Based Polyamides Bearing Sulfonated Moieties

Abstract

Most commercially available polymers are synthesized from compounds derived from petroleum, a finite resource. Because of this, there is a growing interest in the synthesis of new polymeric materials using renewable monomers. Following this concept, this work reports on the use of muconic acid as a renewable source for the development of new polyamides that can be used as proton-exchange membranes. Muconic acid was used as a comonomer in polycondensation reactions with 4,4′-(hexafluoroisopropylidene)bis(p-phenyleneoxy)dianiline, 2,5-diaminobencensulfonic acid, and 4,4′-diamino-2,2′-stilbenedisulfonic acid as comonomers in the synthesis of two new series of partially renewable aromatic–aliphatic polyamides, in which the degree of sulfonation was varied. Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (1H, 13C, and 19F-NMR) techniques were used to confirm the chemical structures of the new polyamides. It was also observed that the degree of sulfonation was proportional to the molar ratio of the diamines in the feed. Subsequently, membranes were prepared by casting, and a complete characterization was conducted to determine their decomposition temperature (Td), glass transition temperature (Tg), density (ρ), and other physical properties. In addition, water uptake (Wu), ion-exchange capacity (IEC), and proton conductivity (σp) were determined for these membranes. Electrochemical impedance spectroscopy (EIS) was used to determine the conductivity of the membranes. MUFASA34 exhibited a σp value equal to 9.89 mS·cm−1, being the highest conductivity of all the membranes synthesized in this study.