Synthesis and applications of new bifunctional dyes bis (monochlorotriazine) based on tetrahydrobenzo[b]thiophene moiety

Fatma Ali Mohamed (Dyeing, Printing and Auxiliaries Department, National Research Centre, Giza, Egypt)
Rafaat Melad Mohareb (Chemistry Department, Cairo University, Giza, Egypt)

Pigment & Resin Technology

ISSN: 0369-9420

Publication date: 28 June 2013

Abstract

Purpose

The purpose of this paper is to synthesise, characterise and find out properties of some new bifunctional dyes bis (monochlorotriazine) using tetrahydrobenzo[b]thiophene systems as the chromophoric moiety, bearing good colour strength, lightfastness, and other favourable properties.

Design/methodology/approach

The novel reactive dyes were prepared, containing bis monochlorotriazine as reactive groups. The dye is synthesised by diazotization and coupling reactions. Firstly the authors synthesised the ethyl 2‐amino 4,5,6,7‐tetrahydrobenzo[b]thiophen‐3‐carboxylate chromophoric moiety compound which in turn underwent diazotization and coupling then diazotized and coupled reaction with either 1‐amino‐8‐naphthol‐3,6‐disulphonic acid (H‐acid) and or 2‐amino‐8‐naphthol‐6‐sulphonic (γ acid) to give the monoazo dye intermediates compounds. The latter products reacted with 2,4,6‐trichloro‐1,3,5‐triazine in 1:1 molar ratio afforded, via nucleophilic displacement when subjected to condensation 2,4,6‐trichloro‐1,3,5‐triazine in 1:1 molar ratio afforded via nucleophilic displacement, which reacted with 1,4‐phenylenediamine in 2:1 molar ratio to give reaction with the 1,4‐phenylenediamine in 2:1 molar ratio, the bisazobifunctional bismonochlorotriazine reactive dyes.bisazo bifunctional bismonochlorotriazine reactive dyes thus yielding the new target reactive. The synthesised dyes were applied onto cotton fabric under the typical exhaust dyeing conditions and their dyeing properties were investigated.

Findings

The results assessed for dyeing indicate high quality dyeing properties However, the homobifunctional (bis MCT) dyes showed higher exhaustion and fixation values, colour yield and fastness properties.

Practical implications

The described method showed the synthesis of bis monochlorotriazines derived from the tetrahydrobenzo[b]thiophene derivative 3 followed by their application towards cotton fabric.

Social implications

Social implications are to prepare new reactive dyes having higher fastness and uses for dyeing cotton which is the commonest fabric use.

Originality/value

In this work, the novel reactive dyes derived from the tetrahydrobenzo[b]thiophene derivative 3 were synthesized and their structures were based on the analytical and spectral data. Such a group of compounds are considered to be excellent reactive dyes with different colour shades.

Keywords

Citation

Mohamed, F. and Melad Mohareb, R. (2013), "Synthesis and applications of new bifunctional dyes bis (monochlorotriazine) based on tetrahydrobenzo[b]thiophene moiety", Pigment & Resin Technology, Vol. 42 No. 4, pp. 264-270. https://doi.org/10.1108/PRT-10-2011-0084

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Publisher

:

Emerald Group Publishing Limited

Copyright © 2013, Emerald Group Publishing Limited

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