Rapid Colorimetric Analysis of para-Phenylenediamine in Henna-based, Non-permanent Tattoo Color Mixtures

Jul 1, 2011 | Contact Author | By: Christopher T. Krüger; Dirk W. Lachenmeier, PhD; Evamaria Kratz; and Gerd Mildau, PhD, Chemisches und Veterinäruntersuchungsamt (CVUA) Karlsruhe
Your message has been sent.
(click to close)
Contact the Author
Save
This item has been saved to your library.
View My Library
(click to close)
Save to My Library
Title: Rapid Colorimetric Analysis of para-Phenylenediamine in Henna-based, Non-permanent Tattoo Color Mixtures
para-phenylenediaminex Lawsonia plantx skinx contact dermatitisx cosmeticsx
  • Article
  • Media
  • Keywords/Abstract

Keywords: para-phenylenediamine | Lawsonia plant | skin | contact dermatitis | cosmetics

Abstract: In some henna mixtures, para-phenylenediamine (PPD) has illegally been added and it is responsible for complications such as allergic contact dermatitis. While high-performance liquid chromatography has previously been used to detect PPD, a colorimetric method that is faster and portable, described here, has been developed. For product developers, this method can be used to evaluate henna plant extracts.

View citation for this article

CT Krüger, D Lachenmeier, E Kratz and G Mildau, Rapid Colorimetric Analysis of para-Phenylenediamine in Henna-based, Non-permanent Tattoo Color Mixtures, Cosm & Toil

Excerpt Only This is a shortened version or summary of the article you requested. To view the complete article, please log in or create an account. Registration is Free!

Tattoos have been used throughout history as body decorations and they comprise an integral element of various cultures. However, many individuals are uncomfortable with the fact that tattooing is virtually irreversible since dyes are injected under the skin into the dermis. An alternative that has grown in popularity is temporary tattoos based on henna. This treatment is normally safe and does not injure the skin surface; it involves exposing the skin externally to a henna tattoo mixture that contains ground henna leaves mixed with water or oil.

The natural dye in henna leaves is 2-hydroxy-1,4-naphtoquinone (Lawsone), which reacts on the skin surface with skin proteins, leading to a temporary orange-brown coloring of the skin. Natural henna tattoo mixture—i.e., without para-phenylenediamine (PPD), is applied using semi-conical containers to make it easier to achieve elaborate designs and is left on the skin for three to six hours. The longer the exposure time, the darker the final color, which is never black as is often assumed, but a dark orange-brown. By adding PPD to the henna tattoo mixture, the application time can be significantly reduced and the results appear more like the desired black color. However, the autoxidation products of PPD including Bandrowski’s base, a trimer of PPD, are very strong potential skin sensitizers, thus the addition of PPD is responsible for most reported skin complications arising from the use of black henna, such as allergic contact dermatitis, post-inflammatory hyperpigmentation, or even worse, an allergic sensitization to PPD and the many substances that cross-react with it, including para-aminophenol, para-toluenediamine or many azoic dyes, such as disperse orange 3.

Excerpt Only This is a shortened version or summary of the article you requested. To view the complete article, please log in or create an account. Registration is Free!

 

Close

Figure 1. Mechanism of the dye formation by oxidation of PPD and coupling with resorcinol15

Figure 1. Mechanism of the dye formation by oxidation of PPD and coupling with resorcinol

A very simple and prominent representative for a coupler is resorcinol (meta-dihydroxybenzene). The possible mechanism of the dye formation is shown in Figure 1.15

Figure 2. Absorption spectra of the PPD-resorcinol reaction product at different PPD concentrations

Figure 2. Absorption spectra of the PPD-resorcinol reaction product at different  PPD concentrations

The authors finally proved there is a clear linear dependency between PPD concentration and absorption (R2 = 0.99).

Figure 3. Demonstration of the visual detection level of 0.1% w/w PPD in henna tattoo mixture

Figure 3. Demonstration of the visual detection level of 0.1% w/w PPD  in henna tattoo mixture

Figure 3 shows the reaction solution marked with “+” and the blank solution marked with “-” of a henna powder spiked with 0.1% w/w PPD after 5 min reaction time.

Footnotes (CT1107 Kruger)

a Resorcinol was obtained from Sigma-Aldrich.
b PPD, copper(II) sulfate pentahydrate, hydrochloric acid and methanol were purchased from Merck.
c Hydrogen peroxide was purchased from Fluka.
d Screw cap vials and plastic syringes were purchased from neoLab.
e The Lambda 12 dual beam spectrometer is manufactured by Perkin Elmer.
f UV WinLab software (version 2.80.03) is manufactured by Perkin Elmer.

Next image >

 
 

Close

It's Free...

Register or Log in to get full access to this content

Registration includes:

  • Access to all premium content
  • One click ingredient sample requests
  • Save articles in the My Library tool

Create an Account or Log In