Synthesis and investigation of dyeing properties of 8-hydroxyquinoline-based azo dyes
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ORIGINAL PAPER
Synthesis and investigation of dyeing properties of 8‑hydroxyquinoline‑based azo dyes Md. Mahfuzur Rahman1 · Tarek Md. Anamul Haque2 · Nafish Sams Sourav3 · Sadia Rahman3 · Subrina Yesmin3 · Rony Mia3 · Abdullah Al Noman3 · Khadija Begum2 Received: 17 July 2020 / Accepted: 18 September 2020 © Iranian Chemical Society 2020
Abstract A facile and well-known synthetic strategy has been used to prepare two novel 8-hydroxyquinoline-based azo dyes to apply as a disperse dye to polyester fabric. In this method, 8-hydroxyquinoline possessing a “privileged structure” which is made up of two rings, a phenol ring fused with pyridine ring, has been coupled with diazonium salt obtained from 2-amino6-nitrotoluene (Dye-I) and with the diazonium salt obtained from 4-chloro-aniline (Dye-II). The structure of the dyes has been confirmed using nuclear magnetic resonance spectroscopy, Fourier-transform infrared spectroscopy, and elemental analysis. As-synthesized dyes are used as disperse to polyester fabric, and the dyed samples were characterized for color fastness to washing, light, rubbing, and perspiration. The fastness testing results indicate that the dyes have a good affinity to PET fabric as the dyed PET fabrics have moderate to excellent fastness to washing and light and very good fastness to rubbing and perspiration. The dyeing property of 8-hydroxyquinoline-based dyes is very promising and can be considered as the potential candidate to meet the actual demand of PET fabric dyeing in the textile industry. Keywords 8-Hydroxyquinoline (HQ) · Dispersed dye · Polyester fabric
Introduction Design and synthesis of a variety of high-performance disperse dyes are receiving special attention because of their rising demand in the polyester industry. Dyeing of polyester fabrics with disperse dyes is very popular due to their brilliancy, wide range of hue, and excellent fastness properties in addition to the environmental and economic reasons [1–5]. Disperse dyes are dispersed in water using surfactant Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-02070-2) contains supplementary material, which is available to authorized users. * Md. Mahfuzur Rahman [email protected] 1
Department of Industrial and Production Engineering, Jashore University of Science and Technology (JUST), Jashore, Bangladesh
2
Department of Chemistry, National Institute of Textile Engineering and Research (NITER), Nayarhat, Bangladesh
3
Department of Textile Engineering, National Institute of Textile Engineering and Research (NITER), Nayarhat, Bangladesh
due to their limited solubility before applying them to the polyester fabrics [3, 6, 7] where dyes are transferred in the molecular state to PET (Polyethylene terephthalate) fiber through a process of surface deposition, absorption, and diffusion. During these processes, disperse dye molecules may be still on the PET fiber as the surface dye resulting in poor washing and rubbing fastness [8, 9]. Although many resear
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