Synthesis and properties of disazo acid dyes

Blus, K.

doi:10.1016/s0143-7208(99)00058-3

Cited by 8 publications

(8 citation statements)

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“…Acid dyestuffs are a structurally simple but important dye category mainly used for dyeing wool, silk and nylon fabrics under acidic conditions 1–6 . The main binding force between the acid dye and fibre is the ionic bond which is easily dissociated by water ionisation, resulting in low wet fastness 7,8 .…”

Section: Introductionmentioning

confidence: 99%

N‐Sulphonatoalkyl indophenine derivatives: Design, synthesis and dyeing properties on wool, silk and nylon fabrics

Cai

Jiang

Cui

et al. 2020

Coloration Technology

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The importance of quinonoidal planarity in improving the wet fastness of acid dyes was studied in a new series of N‐sulphonatoalkyl‐substituted indophenine derivatives. These derivatives were synthesised via the sulphonatoalkylation reaction of isatins with alkanesultone or sodium bromoalkanesulphonate followed by the indophenine reaction. The effects of the position of sulphonic acid groups, length of the alkyl chain, and electron‐donating/withdrawing groups on geometry, electronic structure, solubility, and absorption properties were systematically examined and correlated with the performances of the dyes on wool, silk and nylon fabrics. The N‐sulphonatoalkyl indophenine dyes could exhibit a blue colour in N,N‐dimethylformamide (DMF) and on silk or nylon fabric but a purplish colour in water and on wool fabric. Methoxy groups had a negative impact on the molar extinction coefficient and dye exhaustion, leading to relatively poor dyeing performance. In comparison, fluorine or chlorine atoms were less influential. The introduction of nitro groups could induce a yellowness to the dyed fabrics caused by the strengthened absorption at the region of 360 to 420 nm and reduce the dyeing rate and wet fastness level due to the low dye–fibre affinity. In general, the N‐sulphonatoalkyl indophenine dyes exhibited satisfactory washing and rubbing fastness, especially on dyed nylon fabric. This study provides insight into the structure–property relationship of indophenine dyes and demonstrates that sulphonatoalkylation is an efficient methodology for designing high‐performance textile dyestuffs based on quinonoidal heterocyclic structures.

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Section: Introductionmentioning

confidence: 99%

N‐Sulphonatoalkyl indophenine derivatives: Design, synthesis and dyeing properties on wool, silk and nylon fabrics

Cai

Jiang

Cui

et al. 2020

Coloration Technology

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“…In contrast, intermediates containing a benzene sulphonamide linker group have been recognised to be a substitute of benzidine, and the resultant dyes based on them have been manufactured. [7–17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of branched azo dyes based on benzene sulphonamide intermediates and their spectral properties

Wang

Cai

et al. 2012

Coloration Technology

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Benzene sulphonamide intermediates and two series of branched azo dyes (one series with H‐Acid as the coupling component, and the other, with a pyrazolone derivative as the coupling component) derived from them were synthesised. The molecular structures, spectroscopic properties and dyeing properties of the dyes obtained have been investigated. The results indicated that these dyes showed one dominant hue, despite each separate branch of chromophore, and, in the first series, four chromophoric groups led to only a threefold increase in the extinction coefficient, while the same comparison in the second series produced a fully additive effect, i.e. a fourfold increase. Compared with the mono‐branch dye of each series, the dyeing properties of the H‐Acid series were improved, whereas the pyrazolone series that were run diversely for the two series were synthesised from different coupling components. In addition, the crystallographic structure of the tri‐branch intermediate showed a non‐coplanar structure, which indicated that the derived dye would perform as the sum of three similar chromophoric units.

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“…However, some azo dyes have toxicological properties and therefore require sensitive and selective methods to determine their physicochemical characteristics . Therefore, the solvent used as a medium for chemical and physical processes plays an important role on the ionization, and the widespread application of azo compounds as dyes; as acid−base, redox, metallochrome indicators; or as histological stains has attracted many studies of their acid−base properties. , On the other hand, diazo acid dyes containing one sulfonic group have been widely used for dying polyamide fibers …”

Section: Introductionmentioning

confidence: 99%

“…9 Therefore, the solvent used as a medium for chemical and physical processes plays an important role on the ionization, and the widespread application of azo compounds as dyes; as acid-base, redox, metallochrome indicators; or as histological stains has attracted many studies of their acid-base properties. 6,10 On the other hand, diazo acid dyes containing one sulfonic group have been widely used for dying polyamide fibers. 10 These findings drew our attention to continue our work in this respect, especially determination of pK a .…”

Section: Introductionmentioning

confidence: 99%

“…6,10 On the other hand, diazo acid dyes containing one sulfonic group have been widely used for dying polyamide fibers. 10 These findings drew our attention to continue our work in this respect, especially determination of pK a . 11 In the present article we use some novel azothienopyridine compounds to study the effect of medium on their ionization constants.…”

Section: Introductionmentioning

confidence: 99%

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Spectrophotometric Investigation of the Role of Organic Solvents in the Ionization of Azo Dyes Derived from Thienopyridine

Rageh

Abdallah

2003

J. Chem. Eng. Data

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The effects of different organic solvent + water mixtures on the acidity constants of some azothienopyridine derivatives were studied. The organic solvents used are methanol, ethanol, acetone, and dimethylformamide. The results obtained are discussed in terms of the solvent characteristics. The pK a values of the dyes studied were determined and found to depend largely on both the amount and nature of the organic cosolvent. Hydrogen-bonding interactions of the conjugate base with solvent molecules as well as the solvent basicity contribute the major effect on the ionization process. The effect of the molecular structure of the azo compound on the pK a value is discussed.

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Synthesis and properties of disazo acid dyes

Cited by 8 publications

References 0 publications

N‐Sulphonatoalkyl indophenine derivatives: Design, synthesis and dyeing properties on wool, silk and nylon fabrics

N‐Sulphonatoalkyl indophenine derivatives: Design, synthesis and dyeing properties on wool, silk and nylon fabrics

Synthesis of branched azo dyes based on benzene sulphonamide intermediates and their spectral properties

Spectrophotometric Investigation of the Role of Organic Solvents in the Ionization of Azo Dyes Derived from Thienopyridine

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