Partially bio‐based furyl‐functionalized organosoluble poly(ether ether ketone)s

Abstract

A new series of partially bio‐based (co)poly(ether ether ketone)s bearing pendent furyl groups was synthesized by nucleophilic aromatic substitution polycondensation of varying molar proportions of 4,4′‐(furan‐2‐ylmethylene)bis(2‐methoxyphenol) and bisphenol‐A with 4,4′‐difluorobenzophenone. The chemical structures, compositions and random nature of (co)poly(ether ether ketone)s were confirmed by NMR spectroscopy. Inherent viscosities and number‐average molecular weights of the (co)poly(ether ether ketone)s were in the range 0.74–2.90 dL g−1 and 33 500–46 300 g mol−1, respectively, indicating the formation of reasonably high molecular weight polymers. (Co)poly(ether ether ketone)s were readily soluble in common organic solvents and could be cast into tough, transparent and flexible films from chloroform solutions. (Co)poly(ether ether ketone)s exhibited 10% weight loss and glass transition temperatures in the range 429–464 and 152–156 °C, respectively. A representative copoly(ether ether ketone) was crosslinked with 1,1′‐(methylenedi‐1,4‐phenylene)bismaleimide via Diels–Alder reaction to form a crosslinked polymer which showed improved mechanical properties and was recycled twice without significant loss of mechanical properties. Diels–Alder/retro Diels–Alder reaction was demonstrated by studies of sol–gel transformation, solubility tests, DSC and stress–strain measurements. © 2020 Society of Chemical Industry

Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass

“…Condensation of guaiacol with furfural results in the bisphenolic monomer, which was copolymerized with widely used in the resin industry bisphenol A (BPA) and either difluorinated benzophenone 178 or biphenyl sulfone. 179 Both copolymers have random structures and good thermal stability and are suitable for the construction of tough transparent and flexible films.…”

Renewable and safer bisphenol A substitutes enabled by selective zeolite alkylation

“…Polyesters were synthesized on a mg scale via interfacial polymerization with terephthaloyl chloride, according to methods reported previously with slight modi cations. 23,65,66 In a two-neck round bottom ask (25 mL), under continuous stirring 1.7 mL of 1 M NaOH aq was added to 0.8 mmol of the bisphenol or bisguaiacol (> 99.5%) at 10°C. Once dissolved, 9.3 mg of benzyl triethyl ammonium chloride (BTEACl) was added, and the polymerization was initiated through the addition of a stoichiometric amount of terephthaloyl chloride (TPC) dissolved in DCM (4.6 mL) and the mixture was vigorously stirred for 1 hour at 10°C.…”

Special issue: PAEKing ahead into the 21st century

“…Kuhire et al . report a thought‐provoking reversible cross‐linking of PAEK networks through the inclusion of pendent furyl species into the backbone during synthesis 1 . The furyl units were subsequently exploited through an orthogonal and reversible cross‐linking mechanism resulting in tough three‐dimensional networks.…”