The generation of superoxide and hydrogen peroxide by exposure of fluorescent whitening agents to UVA radiation and its relevance to the rapid photoyellowing of whitened wool

Millington, Keith R.; Maurdev, George

doi:10.1016/j.jphotochem.2004.03.017

Cited by 43 publications

(33 citation statements)

References 27 publications

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“…It was found that irradiation of aqueous solutions of FWAs with UVA (320–400 nm) wavelengths led to the formation of the superoxide radical anion (O 2 −˙ ) and hydrogen peroxide (H 2 O 2 ) (4). Experiments carried out using FWAs from each of the three major classes (stilbenes, pyrazolines and coumarins) all produced H 2 O 2 on exposure to the wavelengths present in sunlight.…”

Section: Introductionmentioning

confidence: 99%

“…Experiments carried out using FWAs from each of the three major classes (stilbenes, pyrazolines and coumarins) all produced H 2 O 2 on exposure to the wavelengths present in sunlight. A four‐fold increase in the concentration of H 2 O 2 was observed when wet FWA‐treated wool was irradiated compared with irradiated bleached wool (4). Further studies showed that irradiation of an aqueous distyrylbiphenyl FWA produced significantly higher concentrations of H 2 O 2 in the presence of certain amino acids, in particular arginine and tryptophan (5).…”

Section: Introductionmentioning

confidence: 99%

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The Photoyellowing of Stilbene‐derived Fluorescent Whitening Agents—Mass Spectrometric Characterization of Yellow Photoproducts

Dyer

Cornellison

Bringans³

et al. 2007

Photochem & Photobiology

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The application of fluorescent whitening agents (FWAs) significantly accelerates the photoyellowing of wool and silk under exposure to the ultraviolet and visible components of sunlight <500 nm. The photochemistry involved in this process is poorly understood, particularly the role of photoproducts derived directly from the FWA itself. Hydroxylation was identified as the key initial mechanism of photodegradation leading to coloration of the solution in the irradiation of the stilbene-derived FWA 4,4'-bis(2-sulfostyryl)biphenyl (DSBP) in the presence of hydrogen peroxide (H2O2). Polyhydroxylated DSBP derivatives were implicated as critical intermediates in the formation of yellow photoproducts under these conditions. The formation of trace quantities of DSBP quinone derivatives subsequent to hydroxylation was identified as the key cause of DSBP photoyellowing. These results are the first successful characterization of yellow photoproducts resulting directly from irradiation of a stilbene-based FWA. Formation of these yellow stilbene-based FWA-derived photoproducts may occur on the surface of FWA-treated wool exposed to simulated sunlight, as previous work has shown that H2O2 is photogenerated when wet FWA-treated wool is exposed to light. These results therefore suggest that yellow FWA-derived photoproducts contribute to the accelerated photoyellowing of FWA-treated wool.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Photoyellowing of Stilbene‐derived Fluorescent Whitening Agents—Mass Spectrometric Characterization of Yellow Photoproducts

Dyer

Cornellison

Bringans³

et al. 2007

Photochem & Photobiology

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“…3. It is interesting to note that a similar mechanism involving electron transfer from wool to stilbene-based fluorescent whitening agents has been proposed to explain the rapid photo-yellowing of fluorescently whitened wool [34,35]. Equation (9) is important in the rapid yellowing mechanism, since this produces superoxide radical anions and hence a route to H 2 O 2 and OH in the presence of trace metal ions.…”

Section: Photo-yellowing Of Wool Dyed With Triphenylmethane Dyes (Bwsmentioning

confidence: 95%

The effect of dyes on photo-induced chemiluminescence emission from polymers

Millington

Zhang

Jones

et al. 2010

Polymer Degradation and Stability

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“…(3)) [40][41][42][43]. It is commonly realized that in nature water, absorption of ultraviolet radiation by dissolved organic matter (DOM) generates an excited triplet state, which reacts with molecular oxygen to form superoxide radicalion [37,39].…”

Section: Formation Mechanism Of Hydrogen Peroxidementioning

confidence: 99%

Photodecomposition of 4-chlorophenol by reactive oxygen species in UV/air system

et al. 2011

Journal of Hazardous Materials

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The generation of superoxide and hydrogen peroxide by exposure of fluorescent whitening agents to UVA radiation and its relevance to the rapid photoyellowing of whitened wool

Cited by 43 publications

References 27 publications

The Photoyellowing of Stilbene‐derived Fluorescent Whitening Agents—Mass Spectrometric Characterization of Yellow Photoproducts

The Photoyellowing of Stilbene‐derived Fluorescent Whitening Agents—Mass Spectrometric Characterization of Yellow Photoproducts

The effect of dyes on photo-induced chemiluminescence emission from polymers

Photodecomposition of 4-chlorophenol by reactive oxygen species in UV/air system

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