Formula |
CAS |
C6H8N2 |
106-50-3 |
Background
4-Phenylenediamine
base (PPD) is the
primary intermediate in permanent hair dyes and fur dyes. It is an organic compound,
a derivative of
aniline. It
is used as a component of engineering polymers and composites, and an ingredient in hair dyes.
4-Phenylenediamine is a precursor to aramid plastics and fibers such as Kevlar and
Twaron.
4-Phenylenediamine is a common hair dye. The nearly colourless dye precursor
oxidizes to the dye. Also other aniline analogues and derivatives are used
such as 2,5-diaminohydroxyethylbenzene, 2,5-diaminotoluene,
tetraaminopyrimidine, indoanilines and indophenols.
4-Phenylenediamine is easily oxidized, and for this reason derivatives of
PPD are used as antiozonants in production of rubber products. A derivative
called CD-4 is used as a developing agent in color photographic film
development. PPD is also used as a Henna surrogate for temporary tattoos.
Synonyms1,4-Phenylenediamine, 4-Phenylenediamine, p-Phenylenediamine,
p-Phenyldiamine, Paraphenylenediamine, PPD, Phenylenediamine base
2-Methyl-p-phenylenediamine,
2-Methyl-para-phenylenediamine
C.I. 76076, C.I. 76042, C.I. 76060
Orsin, Rodol D, Ursol D,
Benzofur D, Pelagol D, Peltol D, Fouramine D, Fourrine D, Furro D, Futramine
D, Renal PF, Santoflex LC, Tertral D
BRN 0774521, CCRIS 7693, CCRIS 509,
EINECS 202-442-1, EINECS 203-404-7, HSDB 6251, USAF EK-394, AI3-00710
Oxidation Base 10, Developer
13, Developer PF
Related compoundsToluene-2,5-diamine, p,m-Tolylenediamine, p-Toluenediamine,
p-Toluylendiamine, para-Toluenediamine, para-Toluylenediamine,
para-Tolylenediamine, 2,5-Diaminotoluene, 2-Methyl-1,4-benzenediamine, 4-Amino-2-methylaniline, p-Aminoaniline,
4-Aminoaniline, p-Diaminobenzene, 1,4-Diaminobenzene, 1,4-Benzenediamine,
p-Benzenediamine.
UsesCosmetics (permanent hair colors, some
dark-colored cosmetics)
Lithography (printing inks)
Oils, greases,
gasoline
Photocopying
Photographic developers
Primary intermediate
in the production of azo dyes
Rarely, fur and leather dyes
Rubber and
plastic industry (antioxidants and accelerators)
Cross-Reactions
4-Aminobenzoic acid (PABA)
Para compounds
Parabens
Unusual Reactions
Airborne contact dermatitis
Contact urticaria
Erythema multiforme-like
reactions
Photoallergic reactions
References
1. |
Temesvari E. Contact urticaria from
paraphenylenediamine. Contact Dermatitis 1984;11(2):125. |
2. |
Storrs FJ. et al. Prevalence and
relevance of allergic reactions in patients patch tested in North
America - 1984 to 1985. Journal of the American Academy of
Dermatology 1989;20(6):1038-1045. |
3. |
Zug KA, Warshaw EM, Fowler JF
Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS,
Mathias CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North
American Contact Dermatitis Group 2005-2006. Dermatitis 2009;20(3):149-160. |
Auteur(s):
dr. Jan R. Mekkes. Dermatoloog, Amsterdam UMC.