P-phenylenediamine base home ICD10: L23.9

4-Phenylenediamine
Formula CAS
C6H8N2 106-50-3

Nederlands

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.

Synonyms
1,4-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 compounds
Toluene-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.

Uses
Cosmetics (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


patientenfolder


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, AMC, Amsterdam.

27-04-2018 (JRM) - www.huidziekten.nl W3C-html-4.01-valid



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