Identification of early synthetic dyes in historical Chinese textiles of the late nineteenth century by high‐performance liquid chromatography coupled with diode array detection and mass spectrometry

Abstract

In the present study, five classes of synthetic dyes -nitrophenol (picric acid), azo (Orange II), diarylmethane (auramine O), triarylmethine (fuchsine, methyl violet, and malachite green), and anthraquinone (alizarin) dyes -were identified in late-nineteenth-century textiles from the China National Silk Museum by high-performance liquid chromatography coupled with diode array detection and mass spectrometry. Data-dependent acquisition of tandem mass spectra provided some information not only on the molecular mass but also on the fragment ions obtained from precursor ions. These fragmentation patterns, obtained in a single experiment, proved to be useful for identification of the synthetic dyes extracted from the textile samples. In addition, it is worth noting that two anthraquinones, which are probably anthrapurpurin and flavopurpurin, and which were detected in printed cotton, can be used as the markers for distinguishing synthetic alizarin from natural alizarin.

Investigating the fragmentation pathways of β‐naphthol pigments using liquid chromatography/electrospray ionization quadrupole time‐of‐flight mass spectrometry

“…This behavior has been already reported in the literature 51,54 The cleavage of the azo group, possibly happening to the β ‐naphthol in its hydrazone form, occurs in different ways: between two nitrogen atoms in the azo group (the produced ion is labeled as [A] − ) 38,42,59 or between one nitrogen and the neighboring carbon atom (C–N bond labeled as [C] − or N–C bond labeled as [D] − or [E] − ) 38,42,54 . In most cases, the base peak is either the [A] − ion or the [D] − ion.…”

HPLC-DAD and HPLC-ESI-Q-ToF characterisation of early 20th century lake and organic pigments from Lefranc archives

“…Interest in the characterisation of modern organic pigments has only gained momentum in the scientific literature in the last 10 years. Early synthetic dyes have been studied extensively [2,[13][14][15][16]. However, relatively little has been published on organic pigments used in paintings-several projects have revealed van Gogh's painting materials in Europe [16,17] and extensive work has been carried out at the Getty Institute for Conservation in the US [18].…”

“…Separation techniques coupled with spectrophotometric and mass spectrometric detection have shown great potential to address these issues, when sampling and dissolution of the analyte have been possible. Although a definitive charaterization of the material can only be achieved when a multi-analytical approach is applied, only in few cases has it been possible to perform organic and inorganic analyses, leading to the complete information on the samples under study [14,26].…”

It&rsquo;s Only a Part of the Story: Analytical Investigation of the Inks and Dyes Used in the <em>Privilegium maius</em>

“…After a first chromatographic run carried out with an HPLC-DAD-MS system, analyses were repeated on a UHPLC-MS/MS system, in order to verify the presence of chemical markers of synthetic alizarin, such as anthrapurpurin and flavopurpurin. In fact, according to the literature [18,19], these two compounds are known to be by-products of the synthesis of alizarin and, in addition, they do not occur in the species of the genus Rubia [20].…”