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
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N-磺基烷基靛酚衍生物：设计、合成及其对羊毛、丝绸和尼龙织物的染色性能
DOI：
10.1111/cote.12518
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发表时间：
2020-12-14
影响因子：
1.8
通讯作者：
Chen, Weiguo
中科院分区：
文献类型：
--
作者：
Cai, Jinfang;Jiang, Hua;Chen, Weiguo
通过一系列新的n -磺化烷基取代吲哚酚衍生物，研究了喹啉平面性对提高酸性染料湿牢度的重要性。这些衍生物是通过isatins与烷磺酸钠或溴烷磺酸钠的磺化反应合成的，然后是吲哚酚反应。系统考察了磺酸基位置、烷基链长度、供/吸电子基团对染料几何结构、电子结构、溶解度和吸收性能的影响，并与染料在羊毛、丝绸和尼龙织物上的性能进行了对比。N-磺酰基吲哚酚染料在N，N-二甲基甲酰胺（DMF）和丝绸或尼龙织物上呈现蓝色，但在水和羊毛织物上呈现紫色。甲氧基对摩尔消光系数和染料耗竭有负面影响，导致染色性能相对较差。相比之下，氟原子或氯原子的影响较小。硝基的引入会使染色织物在360 ~ 420 nm处吸收增强而产生黄色，并使染色织物的染色速率和湿牢度降低。总的来说，n -磺酰基吲哚酚染料具有令人满意的洗涤和摩擦牢度，特别是对染色尼龙织物。该研究揭示了吲哚酚染料的结构-性能关系，并证明了基于醌类杂环结构的磺化烷基化是设计高性能纺织染料的有效方法。
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.