Synthesis and properties of novel aromatic poly(ester-amide)s derived from 1,5-bis(3-aminobenzoyloxy)naphthalene and aromatic dicarboxylic acids

摘要

A new naphthalene-ring-containing bis(ester-amine), 1,5-bis(3-aminobenzoyloxy)naphthalene, was prepared from the condensation of 1,5-dihydroxynaphthalene with 3-nitrobenzoyl chloride followed by catalytic hydrogenation. A series of novel naphthalene-containing polyester-amides was synthesized by direct phosphorylation polyamidation from this bis(ester-amine) with various aromatic dicarboxylic acids. The polymers were produced in high yields and had moderate inherent viscosities of 0.47-0.81 dL g(-1). The poly(ester-amide) derived from terephthalic acid was semicrystalline and showed less solubility. Other polymers derived from less rigid and symmetrical diacids were amorphous and readily soluble in most polar organic solvents and could be solution-cast into transparent, flexible and tough films with good mechanical properties. The amorphous polyester-amides displayed well-defined glass transition temperatures of between 179 and 225 C from differential scanning calorimetry and softening temperatures of between 178 and 211degreesC from thermomechanical analysis. These polyester-amides did not show significant decomposition below 400degreesC in nitrogen or air. (C) 2004 Society of Chemical Industry.