Synthesis of new disperse azo dyes based on oxopyridine core

Abstract

Purpose

The purpose of this paper is to evaluate the dyeing performance of newly designed and synthesised azo dye systems based on polyfunctionally substituted oxopyridine core for improved dyeing when applied to synthetic fibres.

Design/methodology/approach

For improved dyeing qualities, various azo dye systems were synthesised based on polyfunctionally substituted oxopyridine core as the coupling component. The heterocyclic moiety was coupled with diazotized aromatic amines or diazotized tetrahydrobenzothiophenes to afford the respective azo or hydrazono systems. Other counterparts were obtained via treatment with different reagents. The structure of the novel systems was elucidated based on elemental analysis and spectral data. Dyeing performance, electronic spectra and optical properties were characterised based on UV and K/S measurements. Fastness properties were also evaluated.

Findings

The novel systems were designed so that the functionalities located on the heterocyclic core afforded structure modification that led not only to good dispersion but also to improved adherence on the fibre. The sites of location led to construction of a resonating system with higher electron mobility and higher absorption maxima.

Research limitations/implications

The azo dyes, used in the present context were synthesised via a step‐wise pathway leading to different systems of dyes. In addition, the variations in substituents and sites of location on the heterocyclic core could also be studied.

Practical implications

The novel azo dye systems based on polyfunctionally substituted oxopyridine core provide a simple practical access to a series of azo dyes with improved dyeing properties. The availability of starting materials, the simplicity and efficiency for production in good yields and high‐purity can lead to valuable achievements for commercial production.

Originality/value

The designed and synthesised azo dye systems could find numerous applications as disperse dyes in the fields of dyeing, printing and surface coating. Moreover, the systems could find applications as reactive dyes for wool, silk and cellulosic fibres.

Citation

Shams, H.Z., Helal, M.H., Samir, I.M. and Mohareb, R.M. (2008), "Synthesis of new disperse azo dyes based on oxopyridine core", Pigment & Resin Technology, Vol. 37 No. 5, pp. 299-307. https://doi.org/10.1108/03699420810901972