Synthesis and application of a novel, triphendioxazine‐based, phosphorus‐containing acid dye for wool

Cui, Jinhai; Zhang, Shufen

doi:10.1111/cote.12352

Cited by 12 publications

(8 citation statements)

References 16 publications

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“…However, the affinity between the acid dye and silk fibroin is mainly via ionic bonds, which are easily affected by water ionisation, generally producing colour fastness ratings lower than 3. 8 In contrast to acid dyes, conventional reactive dyes can react with the amino group of the macromolecular segments of protein fibres and the phenolic hydroxyl group in tyrosine residues to form covalent bonds through the reactive group in conventional reactive dyes, capable of firmly bonding the dyes to the silk fibre. However, the conventional reactive dyes can be hydrolysed and lose their reactive ability during dyeing and storage processes.…”

Section: Introductionmentioning

confidence: 99%

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Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

Guo

Chen

Cui

et al. 2020

Coloration Technology

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Acid dyes are employed for commercially dyeing silk, which results in ionic bonds between the silk fibroin and the dye. This generally leads to low wet fastness properties for dyed silk fabrics. In this work, three commercial acid dyes with aromatic primary amine structures were selected to dye silk using a Mannich-type reaction, resulting in improved wet fastness of dyed silk by forming covalent bonds between silk fibroin and dye. The Mannich-type reactive dyeing was applied to silk fabrics at both 30 and 90°C in trials. Dyeing at 90°C can shorten the dyeing time compared How to cite this article: Guo Q, Chen W-G, Cui Z-H, Jiang H. Reactive dyeing of silk using commercial acid dyes based on a three-component Mannich-type reaction.

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Section: Introductionmentioning

confidence: 99%

“…Acid dyes have the characteristics of a wide colour range, bright colour and low cost. However, the affinity between the acid dye and silk fibroin is mainly via ionic bonds, which are easily affected by water ionisation, generally producing colour fastness ratings lower than 3 8 …”

Section: Introductionmentioning

confidence: 99%

Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

Guo

Chen

Cui

et al. 2020

Coloration Technology

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“…Another method to achieve better wet fastness is to enhance the van der Waals force by designing planar chromophores with large π‐conjugation systems. Typical examples include triphendioxazine, 10,11 naphthalimide, 12 and perylene 13 . However, the synthesis of planar building blocks is lengthy and complicated.…”

Section: Introductionmentioning

confidence: 99%

“…The sulphonic acid group is the most frequently used substituent to increase the solubility of the compound. Direct sulphonation with concentrated sulphuric acid (H 2 SO 4 ), fuming H 2 SO 4 , or chlorosulphonic acid (HSO 3 Cl) is an efficient method for the introduction of sulphonic acid groups 11 . However, the presence of electron‐rich moieties in dye molecules and excessive sulphonation reagents are required.…”

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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“…Aromatic compounds as basic chemical feedstocks are important fundamental skeletons for many functional compounds such as pharmaceuticals 1 , dyes, 2 and polymeric materials. 3 Traditionally obtained from fossil resources, the Friedel-Crafts reaction was one of the most important…”

Section: Introductionmentioning

confidence: 99%

Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

Lang¹,

Li²,

Zeng³

2020

Synlett

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Substituted aromatic compounds play important roles in materials, biological agents, dyes, etc. Thus, the synthesis of substituted aromatic compounds has been a hot topic throughout the history of organic chemistry. Traditionally, the Friedel–Crafts reaction was a powerful tool for synthesizing substituted aromatic compounds. In recent decades, metal-catalyzed cross-coupling reactions were well developed via carbon–heteroatom bond cleavage, however, having difficulties towards some strong bonds, such as C(Ar)–OH. To overcome such challenges, newer strategies are needed. In this review, we summarize the recent efforts in the development of dearomatization–rearomatization strategy for cross-coupling reactions via C(Ar)–O bond cleavage.1 Introduction2 Dearomatization–Rearomatization Strategy for Cross-Coupling of Phenols3 Dearomatization–Rearomatization Strategy for Cross-Coupling of Biphenols4 Dearomatization–Rearomatization Strategy for Cross-Coupling of Diphenyl Ethers5 Dearomatization–Rearomatization Strategy for Cross-Coupling of Indoles6 Summary

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Synthesis and application of a novel, triphendioxazine‐based, phosphorus‐containing acid dye for wool

Cited by 12 publications

References 16 publications

Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

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

Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

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