Synthesis, characterization, and properties of novel aromatic polyamides containing phthalazinone moiety

Abstract

A unsymmetrical and kink non-coplanar heterocyclic dicarboxylic acid monomer, 4-[4-(4-carboxy phenoxy)-naphthyl]-2-(4-carboxyphenyl)phthalazin-1-one (3) was successfully synthesized with high purity and high yields. A series of novel polyamides containing phthalazinone were prepared from the newly synthesized dicarboxylic acid with various aromatic diamines by means of the phosphorylation polycondensation reaction. Molecular weights of the obtained polyamides were evaluated viscometrically, and the inherent viscosities (ηinh) measured were in the range 0.54–0.69 dL/g. These polyamides were amorphous and readily soluble in many organic solvents, such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimetheylformamide, dimethyl sulfoxide, pyridine, and m-cresol etc., and they could easily be solution-cast into transparent, flexible films with good mechanical properties, with tensile strength ranging from 63.9 to 81.6 MPa and elongation at break from 7.2 to 11.4%. These polymers still kept good thermal stability with high-glass transition temperatures in the range of 283–338 °C, and the decomposition temperature in nitrogen for a 10% weight-loss temperatures in excess of 490 °C, and char yield at 800 °C in nitrogen ranged from 56 to 63%. Furthermore, the polyamides films were essentially colorless; their cut-off wavelengths were between 365 and 379 nm.