p-Phenylenediamine

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna. p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna. PPD is produced via three routes. Most commonly, 4-nitrochlorobenzene is treated with ammonia and the resulting 4-nitroaniline is then hydrogenated: In the DuPont route, aniline is converted to diphenyltriazine, which is converted by acid-catalysis to 4-aminoazobenzene. Hydrogenation of the latter affords PPD. PPD is a precursor to aramid plastics and fibers such as Kevlar and Twaron. These applications exploit PPD's difunctionality, i.e. the presence of two amines which allow the molecules to be strung together. This polymer arises from the reaction of PPD and terephthaloyl chloride. The reaction of PPD with phosgene gives the diisocyanate, a precursor to urethane polymers. This compound is a common hair dye. Its use is being supplanted by other aniline analogues and derivatives such as 2,5-diamino(hydroxyethylbenzene and 2,5-diaminotoluene). Other popular derivatives include tetraaminopyrimidine and indoanilines and indophenols. Derivatives of diaminopyrazole give red and violet colours. In these applications, the nearly colourless dye precursor oxidizes to the dye. PPD is easily oxidized, and for this reason derivatives of PPD are used as antiozonants in production of rubber products (e.g. IPPD). The substituents, naphthyl, isopropyl etc. affect the effectiveness of their antioxidant roles as well as their properties as skin irritants. A substituted form of PPD sold under the name CD-4 is also used as a developing agent in the C-41 color photographic film development process, reacting with the silver grains in the film and creating the colored dyes that form the image. PPD is also used as a Henna surrogate for temporary tattoos. Its usage can lead to severe contact dermatitis. PPD is also used as a histological stain for lipids such as myelin.