Synthesis and Properties of Aromatic Poly(Ether Sulfone)s and Poly(Ether Ketone)s Containing Naphthalene or Quinoline Units, and Methyl-Substituted Biphenyl-4-4’-Diols

A series of poly(ether sulfone)s and poly(ether ketone)s were synthesized from combinations of 1,5- and 2,6-bis(4-fluorosulfonylNaph-thalene, 2,6-bis(4-fluorobenzoyl)naphthalene, and 2,6-bis(4-fluorobenzoyl)quinoline with 3,3’,5,5’-tetramethylbiphenyl-4,4’-dioI and 2,2’,3,3’, 5,5‘-hexamethylbiphenyl-4,4’-diol. The polycondensations proceeded quantitatively in diphenylsulfone in the presence of anhydrous potassium carbonate to afford polymers with inherent viscosities between 0.40 and 1.28 dL/g measured in TV-methyl-2-pyrrolidone or concentrated sulfuric acid. The tetramethyl- and hexamethyl-substituted aromatic polyethers exhibited good thermal stability, did not decompose below 330°C in both air and nitrogen atmospheres, and had higher glass transition temperatures than the corresponding unsubstituted polymers. The methyl-substituted poly(ether sulfone)s and poly(ether ketone)s showed good solubility in such common organic solvents as TV-methyl-2-pyrrolidone, [formula omitted]-dimethylacetamide, tetrahydrofuran, chloroform, and 1,4-dioxane.