Synthesis and characterization of new poly(aryl ether ketone)s bearing (4-phenoxyphenyl)triphenylmethane moieties

Abstract

1,1-Bis(4-hydroxyphenyl)-1-(4-phenoxyphenyl)-1-phenylmethane (BHPPPPM), a new bisphenol monomer, was synthesized with 65% yield from 4-benzoyl diphenyl ether in a one-pot, two-step synthetic procedure. Four new poly(aryl ether ketone)s (PAEKs) bearing (4-phenoxyphenyl)triphenylmethane moieties were prepared from BHPPPPM with four difluorinated aromatic ketones via a nucleophilic substitution reaction. The polycondensation proceeded in tetramethylene sulfone in the presence of anhydrous potassium carbonate and afforded the new PAEKs in nearly quantitative yields with inherent viscosities of 0.60–0.78 dL g−1. The resulting PAEKs having number-average molecular weights in the range of 29,500–34,200 g mol−1 with the polydispersity index ranged from 1.94 to 2.01 are all amorphous and show high glass transition temperatures ranging from 174°C to 196°C, excellent thermal stability, and the temperatures at the 5% weight loss are over 500°C with char yields above 60% at 700°C under nitrogen atmosphere. These new PAEKs are all soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone and N,N′-dimethylacetamide and could also be dissolved in chloroform and tetrahydrofuran. All the polymers formed transparent, strong, and flexible films with tensile strengths of 78–85 MPa, tensile moduli of 1.9–2.4 GPa, and elongations at break of 7–10%.