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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Patch testing with a textile dye mix with and without Disperse Orange 3.

Joanna Stenton1, Jakob Dahlin1, Annarita Antelmi1

  • 1Lund University, Department of Occupational and Environmental Dermatology, Skane University Hospital, Malmö, Sweden.

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Summary

Disperse Orange 3 (DO 3) may be removable from textile dye mix (TDM) formulations. Simultaneous patch testing with TDM and p-phenylenediamine (PPD) is recommended for definitive assessment.

Keywords:
Disperse Orange 3baseline seriescontact allergydisperse dyesp-phenylenediaminepatch testingsimultaneous reactivitytextile dye mix

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Area of Science:

  • Dermatology
  • Allergology
  • Textile Chemistry

Background:

  • Textile dye mix (TDM) 6.6% contains multiple disperse dyes, with Disperse Orange 3 (DO 3) being a frequent allergen.
  • DO 3 elicits strong reactions in patients allergic to p-phenylenediamine (PPD), prompting discussion about its exclusion from TDMs.

Purpose of the Study:

  • To investigate the potential omission of DO 3 from TDM formulations.
  • To assess the clinical significance of DO 3 in TDM-induced contact dermatitis.

Main Methods:

  • Patch testing 2250 dermatitis patients with various TDM concentrations (6.6%, 5.6%, 7.0%) and p-phenylenediamine (PPD) 1.0%.
  • Further patch testing 122 patients with DO 3 1.0% to evaluate its specific contribution.

Main Results:

  • Contact allergy prevalence to TDM 6.6% was 2.4%, TDM 5.6% was 1.8%, and TDM 7.0% was 2.0%.
  • A significant proportion of TDM 6.6%-positive patients (55.6%) also reacted to PPD.
  • High cross-reactivity was observed, with 94.1% of DO 3-positive patients reacting to PPD.

Conclusions:

  • DO 3 can likely be omitted from TDM formulations.
  • Simultaneous patch testing with TDM (6.6%, 7.0%), DO 3 (1.0%), and PPD (1.0%) is necessary for a conclusive decision on DO 3's removal.