To be or not to be an azo pigment: Chemistry for the preservation of historical β-naphthol reds in cultural heritage

Eva Mariasole Angelin, M. Conceição Oliveira, Austin Nevin, Marcello Picollo, Maria J. Melo

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Naphthol reds are historical pigments widely found in cultural heritage, characterized by 1-arylhydrazone-2-naphthol basic skeleton. Little is known about their degradation mechanisms, and this knowledge is essential for their long-term preservation. In this research, for the first time, the photodegradation quantum yields (ΦR) were calculated for a series of pigment reds selected based on published literature, in order to evaluate the effects of the electron-withdrawing and donating groups present in C(4′), in particular the effect of sulfonate groups on the stability of these compounds. ΦR values in homogeneous media, ranging from 3 × 10−6 to 4 × 10−5, are difficult to obtain in these systems, but provide the quantification of the stability of naphthol reds. One of the main conclusions is that the sulfonate groups have a stabilizing effect and that the keto forms are generally more stable. Another important piece of information is that the solvent, and as such the medium predictably, has a major impact on stability. For Sudan I and Orange II irradiation was also carried with a xenon source (λirr ≥ 300 nm), allowing characterizing the main degradation products by HPLC-DAD-MS and UHPLC-HRMS. For the dyes characterized by higher ΦR, extensive degradation was observed with the formation of volatile compounds as phthalates.

Original languageEnglish
Article number109244
JournalDyes and Pigments
Volume190
DOIs
Publication statusPublished - Jun 2021

Keywords

  • Art conservation
  • Azo pigments
  • Photodegradation
  • Photophysics
  • β-Naphthols hydrazone pigments

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