Oxidation by singlet oxygen of arylazonaphthols exhibiting azo–hydrazone tautomerism

Griffiths, J.; Hawkins, Christopher M.

doi:10.1039/p29770000747

Cited by 103 publications

(44 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This is consistent with the literature. [29][30][31] In addition to this, the PCA plots reveal that there is a strong positive contribution at 1434 cm -1 instead of a band at 1445 cm -1 present in the spectra of the printed samples, and a small negative contribution at 1473 cm -1 . This might indicate that the chemical group causing the Raman band at 1434 cm -1 would take part in the photo-degradation reaction of the colorant, whereas the contribution at 1473 cm -1 for one might originate from some photo-degradation reaction product of the DY86 colorant.…”

Section: Resultsmentioning

confidence: 99%

“…The literature suggests that photo-oxidation of azo dyes is affected by the azohydrazone tautomeric equilibrium, the latter being more prone to the oxidative fading. [29][30][31][32] . An earlier study 33 gave indications that on cationic PVA-poly-DADMAC coatings, the pigment ratio of the coating did not seem to influence on the attachment of the anionic DY86 colorant to the coating, possibly owing to the strong interactions between the colorant and poly-DADMAC.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Kerr gated resonance Raman spectroscopy in light fastness studies of ink jet prints

Vikman

Iitti

Matousek

et al. 2005

Vibrational Spectroscopy

View full text Add to dashboard Cite

Resonance Raman spectroscopy offers several advantages in the studies of ink jet prints stemming from its inherent selectivity and sensitivity. These include the possibility to obtain direct information on the chemical interactions between the paper and ink that play a major role in long-term print fastness. However, resonance Raman techniques can suffer from obtrusive fluorescence from colorants or printing substrate and this severely complicates the Raman measurements.The aim of this investigation was to evaluate the applicability of resonance Raman spectroscopy combined with a Kerr gate fluorescence rejection system to gain information on the light fastness of ink jet prints. This was studied using a set of experimental coatings and inks with known compositions. The results indicate that Kerr gated resonance Raman spectroscopy is applicable to the light fastness studies of ink jet prints owing to the effective suppression of the sample-related fluorescence. Moreover, detailed molecular information can be obtained by tuning the laser to get selective resonance enhancement. This enables specific analyses of chemical paper-ink interactions, which generally contribute decisively to the light fastness of ink jet prints.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Kerr gated resonance Raman spectroscopy in light fastness studies of ink jet prints

Vikman

Iitti

Matousek

et al. 2005

Vibrational Spectroscopy

View full text Add to dashboard Cite

show abstract

“…According to their opinion, this photofading is caused by oxidative attack on the ground state hydrazo form by a singlet oxygen. Griffith and Hawkins [7] have also reported that the photochemical oxidation of 4-arylazo-l-naphthol is caused by the singlet oxygen. The singlet oxygen lifetime, however, is too short for the color of dye to fade in aqueous solutions: for example, it is 2/~sec in water [25].…”

Section: Fading Phenomena Of 4-oh In Aqueous Solutions Of Mixed Surfamentioning

confidence: 98%

“…However, only a few studies have been performed on fading phenomena of dyes [7][8][9]. These include the photofading of azo oil dye in an organic solvent, such as methanol, acetone, dichloromethane, or benzene.…”

Section: Introductionmentioning

confidence: 99%

Fading phenomena of azo oil dye in anionic-nonionic surfactant solutions II. Effects of alkyl and/or oxyethylene groups in nonionic surfactant on the fading rate

Ogino

Uchiyama

Abe

1987

Colloid & Polymer Sci

View full text Add to dashboard Cite

Abstract:The effects of alkyl and/or oxyethylene groups in a nonionic surfactant on the fading phenomena of 4-phenylazo-l-naphthol (4-OH), which occur in aqueous solutions of anionic-nonionic surfactant systems, are described; these systems are sodium dodecyl sulfate (SDS) -alkyl poly(oxyethylene) ethers (CmPOEn, m = 12,14,16, and 18 at n = 20; n = 10, 20, 30, and 40 at m = 16). The fading phenomenon is observed when 4-OH is added to the anionic-nonionic mixed surfactant solutions at a molar ratio of i : 1. A singlet oxygen, which is caused by the hydrophilic-hydrophilic interaction between two surfactants, is thought to attack the tautomer of 4-OH. The fading rate of 4-OH accelerates with increasing alkyl chain length or with decreasing oxyethylene chain length in the nonionic surfactant molecule. The effect on the fading behavior of 4-OH would be larger for a system which can easily form a mixed micelle than for a system in which two kinds of micelles coexist.

show abstract

“…Recently, much study has been devoted to photofading of azo oil dyes [1][2][3][4][5]. Griffith and Hawkins [1,2] investigated the photochemical oxidation of arylazonaphthols in methanol; Kuramoto and Kitao [3] studied the photofading of some dyes in organic solvents, such as methanol, acetone, dichloromethane or benzene; Shah andJain [4] reported the light fading of azo dye on poly(vinyl chloride) and poly(ethylene terephthalate); Mustroph and co-workers [5] carried out the photofading of 1-phenylazo-2-naphthol in cellulose acetate.…”

Section: Introductionmentioning

confidence: 99%

Fading phenomena of azo oil dye in anionic-nonionic surfactant solutions III. The effect of solubilizates on the fading behavior of azo oil dye in mixed surfactant systems

Uchiyama

Abe

Oginö

1987

Colloid & Polymer Sci

View full text Add to dashboard Cite

Abstract:The effects of solubilizates on the fading behavior of 4-phenylazo-l-naphthol O-OH) in aqueous solutions of anionic-nonionic mixed surfactant systems are described; the systems studied are sodium dodecyl sulfate (SDS) -octadecyl poly(oxyethylene) ethers (C18POE20). The fading rate of 4-OH in the mixed solution was independent of the addition of octane. By adding octanoic acid, the rate became faster. On the other hand, the 1-octanol slowed the rate. The fading speed of 4-OH decreased as the concentration of the alcohol and the number of carbon atoms in the alcohol molecule, used as a solubilizate, increased. The sizes of mixed micelles penetrated by the solubilizate were dependent on the kind of oily materials and on the alkyl chain lengths in the molecules of normal higher alcohols. Relative viscosities and effective specific volumes in the mixed micellar solutions increased with the increase in the concentration of 1-octanol and octanoic acid, and with increasing the number of alkyl groups in the alcohol molecule. The effect of solubilizates on the fading behavior of 4-OH was found to be dependent on the differences in their solubilization sites in mixed micelles. A solubilizate with a strong polar group supported a hydrophilic-hydrophilic interaction, whereas one including a weak polar group did not.

show abstract

Oxidation by singlet oxygen of arylazonaphthols exhibiting azo–hydrazone tautomerism

Cited by 103 publications

References 0 publications

Kerr gated resonance Raman spectroscopy in light fastness studies of ink jet prints

Kerr gated resonance Raman spectroscopy in light fastness studies of ink jet prints

Fading phenomena of azo oil dye in anionic-nonionic surfactant solutions II. Effects of alkyl and/or oxyethylene groups in nonionic surfactant on the fading rate

Fading phenomena of azo oil dye in anionic-nonionic surfactant solutions III. The effect of solubilizates on the fading behavior of azo oil dye in mixed surfactant systems

Contact Info

Product

Resources

About