Premium
Substituted 1‐[(phosphiny1)methyll‐2,4‐ and ‐2,6‐dinitrobenzenes, 1‐[(phosphinyl) methyl]‐2,4‐ and ‐2,6‐diaminobenzenes: New starting materials for preparation of fire‐resistant polymers
Author(s) -
Mikroyannidis John A.
Publication year - 1984
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1984.070290225
Subject(s) - nitration , sulfuric acid , chemistry , nitric acid , infrared spectroscopy , curing (chemistry) , polymer chemistry , polymer , benzene , hydrolysis , catalysis , organic chemistry , steric effects , nuclear chemistry , medicinal chemistry
The nitration of the substituted [(phosphinyl)methyl]benzenes by fuming nitric and sulfuric acid gave the substituted l‐[(phosphinyl)methy1]‐2,4‐ and ‐2,6‐dinitrobenzenes (1). The formation of the two dinitro isomers was demonstrated by proton nuclear magnetic ('H‐NMR) and infrared (IR) spectroscopy. The nitration of [di(isopropoxy)phosphinylmethyl]benzene gave mainly the p‐nitro derivative due to steric hindrance. The phosphinyl ester groups of 1 were hydrolyzed by acids. The substituted l‐[(phosphinyl)methyl]‐2,4‐ and ‐2,6‐diaminobenzenes (2) were synthesized by catalytic hydrogenation of 1. In addition, the corresponding di(benzoy1amino) derivatives of 2 were prepared. Some of the synthesized compounds were investigated by gas chromatography‐mass spectroscopy (GC‐MS). Compounds 2 can be used as starting materials for preparation of phosphorus‐containing polymers such as polyamides, polyimides, polyureas, and bismaleimides and as curing agents for epoxy resins.