The influence of singlet oxygen in the fading of carbonless copy paper primary dyes on clays

Caine, Michael A; McCabe, Richard W.; Wang, Liangcheng; Brown, Robert G.; Hepworth, John D.

doi:10.1016/s0143-7208(01)00021-3

Cited by 26 publications

(25 citation statements)

References 29 publications

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“…There are two possible mechanisms of degradation of this type of writing ink. The first mechanism is N-demethylation, in which the methyl group of a dye is sequentially replaced by hydrogen when exposed to light [19]. In the second mechanism the degradation occurs due to attack of a dye molecule by singlet oxygen [20,21].…”

Section: Introductionmentioning

confidence: 99%

Analysis of the Aging Processes of Writing Ink: Raman Spectroscopy versus Gas Chromatography Aspects

Grechukha¹,

Gorshkova

Panov

et al. 2017

Applied Sciences

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This work is devoted to the extremely popular but poorly developed scientific and forensic problem of the estimation of the actual dates of inscriptions placed on paper and made by ballpoint pens. It is shown that the degradation of writing inks with time may be controlled via Raman spectroscopy and gas chromatography. The time intervals for the implementation of each of these methods were determined using the ratios of the Raman peak intensities as degradation characteristics rather than their absolute values. In turn, this eliminates the effect of the concentration of a dye. The mutual influence of the volatile components and dyes of writing inks was also investigated and the time interval within which such influence is critical was found. According to the obtained results, a new methodological scheme for determining the age of documents, which were created at least 40 months ago, was proposed.

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Section: Introductionmentioning

confidence: 99%

Analysis of the Aging Processes of Writing Ink: Raman Spectroscopy versus Gas Chromatography Aspects

Grechukha¹,

Gorshkova

Panov

et al. 2017

Applied Sciences

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“…The photodegradation of a dye may occur due to several competing reactions: a) N -demethylation. The methyl group of a dye is sequentially replaced by hydrogen when exposed to light [9] (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

“…2). b) Photooxidative cleavage of the central Cephenyl bond occurs probably via singlet oxygen resulting in benzophenone and phenol formation [9,10] (Fig. 3).…”

Section: Introductionmentioning

confidence: 99%

“…3). It is known that the photolysis of triarylmethane dyes leads to formation of singlet oxygen not only in solution but even on paper [8,9,11]. As a result, in the absence of air under these conditions only leucobases are formed (colorless or weakly colored reduced forms of many organic dyes) [12].…”

Section: Introductionmentioning

confidence: 99%

“…Here, the photoreduction of the excited dye cation is achieved by the addition of an electron to dye photoexcited states or by photochemical hydrogenation of a dye [9,13].…”

Section: Introductionmentioning

confidence: 99%

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The investigation of dye aging dynamics in writing inks using Raman spectroscopy

et al. 2016

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a b s t r a c tThe durability against light and aging dynamics of heteroatomic aromatic dyes and pigments containing nitrogen atoms used in writing inks was studied using Raman spectroscopy. The mechanisms of their thermal and photo-decomposition were proposed and the rates of these processes were determined. According to Raman spectroscopy, it was found that depending on the presence of one or another colorant, there are three main types (Type A, Type B and Type C) of blue dye inks used in ballpoint, gel and capillary pens which were studied in this work. Each type is characterized by a certain set of signals in Raman spectra. Time dependencies of Raman signal intensities for each type revealed the dynamics of the processes occurred with colorants included in the studied inks from the moment when they were printed on paper. Thus, the results obtained in this study can be used for the age estimation of the paper documents up to 15 years.

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Application of LC‐MS and LC‐MS‐MS to the analysis of photo‐decomposed crystal violet in the investigation of cultural heritage materials aging

et al. 2012

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In this work, the accurate liquid chromatography-ultraviolet-visible (LC-UV-Vis), LC-mass spectrometry (MS) and LC-MS-MS analysis of the photo-degradation products of crystal violet (CV) is reported. CV is a light fugitive early synthetic dye which had a widespread diffusion into the market starting from the end of the XIX century and was used among others by V. Van Gogh and P. Gauguin in their writings, drawings or paintings. On-line photodiode array detector enabled simultaneous UV-Vis spectra acquisition. Many degradation compounds were identified through their exact mass (2 ppm accuracy) and MS-MS technique. In particular, all CV demethylated products, demethylated Michler's ketone and particularly some compounds that most likely contain oxygen, such as N-oxides, were found. Fragmentation products are all justified by the proposed fragmentation scheme, in term of precursor exact mass and isotopic profile, characteristic losses in fragmentation and rebuilt structure formula. In particular, we hypothesized the presence of N-imido oxides and hydroxylamine derivates, never reported before, together with the demethylated derivatives of the studied dyes. All these compounds, although at trace level in our samples, contribute to the discoloration and fading of works of arts made with CV. In particular, demethylation of CV by UV light leads to formation of compounds absorbing at shorter wavelengths than CV (blue shift) or no-absorbing in visible range (yellow-colourless) with an overall effect that may appear reddish-brown. This phenomenon justifies drawings appearing grey or brown on aged yellowed paper, when CV-based inks or paints were used. The final aim was to better characterize the photo-degradation of early synthetic dyes (in particular of CV) and to gain a better insight into the discoloration and fading of purple ink strokes made of CV.

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The influence of singlet oxygen in the fading of carbonless copy paper primary dyes on clays

Cited by 26 publications

References 29 publications

Analysis of the Aging Processes of Writing Ink: Raman Spectroscopy versus Gas Chromatography Aspects

Analysis of the Aging Processes of Writing Ink: Raman Spectroscopy versus Gas Chromatography Aspects

The investigation of dye aging dynamics in writing inks using Raman spectroscopy

Application of LC‐MS and LC‐MS‐MS to the analysis of photo‐decomposed crystal violet in the investigation of cultural heritage materials aging

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