Functionalized poly(ether ether ketone) analogs via reactivity ratio controlled polycondensation. (18th August 2015)

• Record Type: Journal Article
• Authors: Boakye, Godfred; Stuck, Rachel; Geremia, Kara; Wehrle, Robert J.; Cooke, R. Hunter; Raghavapuram, Shravanthi; Fossum, Eric
• Is Part Of: Polymer. Volume 72(2015)
• Page Start: 264
• Page End: 270
• Publication Date: 2015-08-18
• Subjects: Reactivity ratios -- Nucleophilic aromatic substitution -- Meta activation; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2015.03.016
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: A route for the introduction of functional groups to poly(ether ether ketone) analogs, via a reactivity ratio controlled polycondensation process, has been developed. The reactivity differences, toward nucleophilic aromatic substitution reactions, of the three electrophilic sites in 3, 4′, 5-trifluorobenzophenone, 1, affords the opportunity to prepare functionalized B2 -type monomers in situ, followed by polycondensation with the appropriate bisphenol to prepare the corresponding linear polymer. The reactivity differences in1 were probed via a combination of 13 C and 19 F NMR spectroscopy along with model reactions using m -cresol as the nucleophile. Reaction of1 with 1.03 molar equivalents of a series of phenols provided the desired B2 -type monomers in high selectivity. The B2 -type monomers were then converted to the linear polymers by reaction with Bisphenol-A and their structures were confirmed via NMR spectroscopy. The thermal properties were evaluated by a combination of thermogravimetric analysis and differential scanning calorimetry. Graphical abstract: Highlights: The reactive sites in 3, 4′, 5-trifluorobenzophenone were evaluated by NMR spectroscopy. Reaction temperature was controlled to prepare functional B2 -monomers in situ . Functional groups were introduced to poly(arylene ether)s via a "one-pot" process. The polymer structures were characterized by NMR spectroscopy and SEC analysis. The development of Reactivity Ratio Controlled Polycondensation, RRCP, was achieved.