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Facile Synthesis of New Aromatic Polyamides Based on 1,2‐Dihydro‐2‐(4‐carboxylphenyl)‐4‐[4‐(4‐carboxylphenoxy)‐3‐methylphenyl]phthalazin‐1‐one
Author(s) -
Lin Cheng,
Lei Ying,
XiaoLing Yang,
XiGao Jian
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590200
Subject(s) - chemistry , pyridine , dimethylacetamide , monomer , amide , polymer chemistry , ether , potassium carbonate , nucleophilic aromatic substitution , nucleophilic substitution , triphenyl phosphite , alkaline hydrolysis , dimethylformamide , polyamide , organic chemistry , hydrolysis , polymer , solvent
A new monomer diacid, 1,2‐dihydro‐2‐(4‐carboxylphenyl)‐4‐[4‐(4‐carboxylphenoxy)‐3‐methylphenyl]phthalazin‐1‐one ( 3 ), was synthesized through the aromatic nucleophilic substitution reaction of a readily available unsymmetrical phthalazinone 1 bisphenol‐like with p ‐chlorobenzonitrile in the presence of potassium carbonate in N , N ‐dimethylacetamide and alkaline hydrolysis. The diacid could be directly polymerized with various aromatic diamines 4a–4e using triphenyl phosphite and pyridine as condensing agents to give five new aromatic poly(ether amide)s 5a–5e containing the kink non‐coplanar heterocyclic units with inherent viscosities of 1.30–1.54 dL/g. The polymers were readily soluble in a variety of solvents such as N , N ‐dimethylformamide (DMF), N , N ‐dimethylacetamide (DMA), dimethylsulfoxide (DMSO), N ‐methyl‐2‐pyrrolidinone (NMP), and even in m ‐cresol and pyridine (Py). The transparent, flexible and tough films could be formed by solution casting. The glass transition temperatures T g were in the range of 286–317 °C.