P-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a colorless solid, but typically samples can contain yellowish impurities arising from oxidation. It is mainly used as a component of engineering polymers and composites. It is also an ingredient in hair dyes.
Uses
Precursor to polymers
PPD is a precursor to aramid plastics and fibers such as Kevlar. These applications exploit PPD's difunctionality. 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.
Dyeing
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.
Rubber antioxidant
PPD is easily oxidized, and for this reason derivatives of PPD are used asantiozonants in production of rubber products. The substituents, naphthyl, isopropyl etc affect the effectiveness of their antioxidant roles as well as their properties as skin irritants.
Other uses
PPD 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.
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