Abstract
A new monomer diacid, 1,2-dihydro-2-(4-carboxylphenyl)-4-[4-(4-carboxylphenoxy)phenyl](2H)phthalazin-1-one (3), was synthesized through the aromatic nucleophilic substitution reaction of a readily available unsymmetrical phthalazinone bisphenol-like (1) with p-chlorobenzonitrile in presence of potassium carbonate in N, N-dimethylacetamide and alkaline hydrolysis. The diacid can be direct polymerized with various aromatic diamines (4a-d) using triphenyl phosphite and pyridine as condensing agents to give a series of new aromatic poly(ether amide)s (5a-d) containing the kink non-coplanar heterocyclic units with inherent viscosities of 1.26-1.53 dl/g. The polymers were readily soluble in a variety of solvents such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAc), dimethylsulfoxide (DMSO), N-methyl-2-pyrrolidinone (NMP), even in m-cresol and pyridine (Py) and partly soluble in chloroform at room temperature and afforded transparent, flexible and tough films by solution casting. The glass transition temperatures (T g) were in the range of 291-329°C, and the temperatures for 5% weight loss in nitrogen were in the range of 445-520°C.
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