Synthesis and application of KM‐type reactive dyes containing 2‐ethoxy‐4‐chloro‐s‐triazine

Abstract

A new kind of hetero‐bifunctional reactive dye containing 2‐ethoxy‐4‐chloro‐s‐triazine, with better activity matching with β‐hydroxyethyl sulphone sulphate at a low fixation temperature, was successfully synthesised and characterised. An ethoxy group was designed to be introduced into triazine to increase the substantivity and the reactivity of the dyes. Thereby, the fixation of mono‐s‐chlorotriazine/hydroxyethyl sulphone sulphate (KM‐type) bifunctional reactive dyes on cotton was improved, and dyeing under mild conditions with high fixation was realised. Nineteen dyes with orange, red and blue colours were synthesised and characterised by UV‐Vis and infrared spectroscopy and mass spectrometry. Synthesised dyes were dyed at 60, 75 and 90°C, respectively. Exhaustion and reactivity for all of the ethoxy‐containing KM‐type dyes was over 90% at the optimal temperature, and fixation was over 87%, which was higher than the ethoxy‐free comparative dyes. The optimal fixation temperature of ethoxy‐containing dyes was initially reduced to 75°C, and then to 60°C. Compared with comparative dyes, the wash fastness and light fastness were basically unchanged, and the wet rub fastness of the H‐acid series was reduced by one grade.

Synthesis and properties of poly(styrene‐co‐maleic acid) macromolecular reactive dyes

“…To compare the influence of ethoxy on the dye solubility and dyeing properties with the other commonly used groups mentioned above, ethanol was also chosen as the first condensation component. When ethanol was used, sodium carbonate was added to neutralise the acid produced in the reaction according to 24 . When H ‐acid and 2,4‐diaminobenzenesulphonic acid were further reacted with the substituted chloro‐ s ‐triazine as shown in Table 1 (No.…”

“…Besides, the macromolecular reactive dyes have good colour fastness properties, because the dyes are fixed by covalent bonds through nucleophilic substitution of the reactive groups and the fibres. The K/S values of all the dyed fabric samples are listed in The fixation of the macromolecular reactive dyes was greatly improved and their light fastness was almost the same compared with that of the small molecule dyes with similar structures in the literature, 24 as shown in Table 5. This is not only because the synthesised dyes have a high chromophore ratio to improve the fixation and that each chromophore contains a reactive group, chloro-s-triazine; it is also possibly because of the electron-withdrawing induced effect of the carboxyl groups on the macromolecular chain to maintain the light fastness.…”

“…When ethanol was used, sodium carbonate was added to neutralise the acid produced in the reaction according to. 24 When H-acid and 2,4-diaminobenzenesulphonic acid were further reacted with the substituted chloro-s-triazine as shown in The condensation products of three and four were diazotised, then they were coupled with H-acid to obtain precursor c and d, respectively, as shown in Scheme 2.…”

Trends in the synthesis and application of some reactive dyes: A review

“…Where R is benzene sulfonamide derivatives. An interesting paper published in 2018 showed that 2-ethoxy-4-chloro-s-triazine, applied to cotton fabric at 70 ⁰C gives 87% fixation value (Zhang et al, 2019). Four KM-type ethoxy containg reactive dyes and 14 comparative dyes were synthesized, J-acid, H-acid and Gamma acid used a coupling component.…”

Synthesis and application of KM‐type reactive dyes containing 2‐ethoxy‐4‐chloro‐s‐triazine

“…Subsequent to the publication of this article, 1 the authors have provided additional information that should have been included in section 2.5.1 as follows:…”