A bio-based N-heterocyclic poly(aryl ether ketone) with a high biomass content and superior properties prepared from two derivatives of guaiacol and 2,5-furandicarboxylic acid

Abstract

To reduce the dependence on non-renewable resources and to address environmental issues, bio-based high-performance poly(aryl ether ketone), PGFEKK, is prepared using two bio-based monomers derived from guaiacol and 2,5-furandicarboxylic acid. With a biomass content of 64.9%, it is the highest biomass content for poly(aryl ether ketone)s reported to date. In this report, the reaction of the bio-based monomers 6-(4-hydroxy-3-methoxyphenyl) pyridazin-3(2H)-one (GSPZ) and furan-2,5-diylbis((4-fluorophenyl)methanone) (BFBF) is carried out via base-catalyzed nucleophilic substitution. The optimum conditions for the reaction are studied using orthogonal experiments and PGFEKK is obtained with a molecular weight up to 21.5 kg/mol, a glass transition temperature of 212 °C, a 10% weight loss temperature of 452 °C, and a tensile strength of 84 MPa. In addition, PGFEKK has a melt viscosity of only 207 MPa at 329 °C and dissolves in most solvents at room temperature. Such a high-performance bio-based poly(aryl ether ketone) has never been reported before. Furthermore, to study the mechanism of how two bio-based monomers affected the polymerization process and material properties, three other polymers are prepared using two petroleum-based monomers, DHPZ and BFBB, instead of GSPZ and BFBF, by analyzing the molecular simulations and the properties of the materials.