Synthesis and characterization of new thermally stable copoly(ester–amide)s from diester–dicarboxylic acids

Abstract

Three new aromatic diester–dicarboxylic acids containing furan rings, namely, benzofuro[2,3- b]benzofuran-2,9-dicarboxyl-bis-phenyl ester-4,4 ′-dicarboxylic acid, benzofuro[2,3- b]benzofuran-2,9-dicarboxyl-bis-phenyl ester-3,3 ′-dicarboxylic acid and benzofuro[2,3- b]benzofuran-2,9-dicarboxyl-bis-naphthyl ester-2,2 ′-dicarboxylic acid were synthesized by the reaction of benzofuro[2,3- b]benzofuran-2,9-dicarbonyl chloride with 4-hydroxybenzoic acid, 3-hydroxybenzoic acid and 3-hydroxy-naphthalene-2-carboxylic acid, respectively. Diester–dicarboxylic acids were characterized by FT-IR and NMR spectroscopy and elemental analyses. Then, these monomers were converted to aromatic copoly(ester–amide)s by their reaction with various aromatic diamines via the direct polycondensation. These polymers were characterized by viscosity measurements, solubility tests, FT-IR, Ultraviolet and 1H-NMR spectroscopy and thermogravimetry. The polymers with inherent viscosities in the range of 0.16–0.37 dl/g in dimethyl sulfoxide at 30 °C were obtained in high yield. Most of them dissolved readily at room temperature in polar solvents. The synthesized copoly(ester–amide)s possessed glass-transition temperatures from 210–255 °C. The copoly(ester–amide)s exhibited excellent thermal stabilities and had 10% weight loss at temperature above 295 °C under nitrogen atmosphere.