Uncatalyzed polymerization of bistriazolinediones with electron-rich aromatic compounds via electrophilic aromatic substitution

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 1989-01, Vol.27 (1), p.217-235
• Main Authors: Mallakpour, Shadpour E., Butler, George B.
• Format: Article
• Language: English
• Subjects: Applied sciences; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts
• ISSN: 0887-624X; 1099-0518
• DOI: 10.1002/pola.1989.080270119

The reaction of 4‐substituted‐1,2,4‐triazoline‐3,5‐diones(4R‐TD's), i.e., MeTD(4‐methyl substituted) and PhTD(4‐Phenyl substituted) with electron rich aromatic compounds were investigated. N,N‐Dimethylaniline undergoes reaction instantaneously with MeTD and PhTD. Electrophilic aromatic substitution occurred at room temperature at the para position without use of any catalyst. N,N,N′,N′‐tetramethyl‐m‐phenylenediamine (TMPDA) undergoes reaction with 2 mol of PhTD and MeTD which lead to the formation of 2:1 adducts in high yields. These compounds were fully characterized by IR, 13C‐NMR, 1H‐NMR and elemental analysis and were used as model compounds. The reaction of bistriazolinediones with TMPDA was performed in dimethylformamid at room temperature. The reactions are exothermic, fast, and gave novel polymer structures via electrophilic aromatic substitution. Some physical properties and structural characterization of these new polymers have been studied, and will be reported.