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Development of novel pH-sensitive azo dyes from Cardanol as a bioresource

Siddhesh Umesh Mestry (Department of Polymer and Surface Engineering, Institute of Chemical Technology (ICT) , Mumbai, India)
Umesh Ratan Mahajan (Department of Polymer and Surface Engineering, Institute of Chemical Technology (ICT) , Mumbai, India)
Aswathy M. (Department of Polymer and Surface Engineering, Institute of Chemical Technology (ICT) , Mumbai, India)
Shashank T. Mhaske (Department of Polymer and Surface Engineering, Institute of Chemical Technology (ICT) , Mumbai, India)

Pigment & Resin Technology

ISSN: 0369-9420

Article publication date: 8 February 2021

Issue publication date: 11 May 2021

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Abstract

Purpose

The purpose of this paper is to use the bio-based resource as the starting material for the synthesis of azo dye. Cardanol is one of the most used bio-based resources for carrying out the synthesis of various compounds having numerous end applications. The study presents an attempt to develop an azo dye from Cardanol having end applications in pH-responsive dyes.

Design/methodology/approach

The cardanol was sulfonated to block the para position by which ortho positioned hydroxyl group after diazotization and coupling will provide necessary pH-sensitivity. The diazotization of two naphthalene derivatives, i.e. 1-naphthol-8-amino-3,6-disulfonic acid (H-acid) and 7-amino-4-hydroxy-2-naphthalene sulfonic acid (J-acid) was carried out using the standard practice, and the diazotized compounds were coupled with the sulfonated cardanol. The obtained dyes were characterized by Fourier transform infrared, nuclear magnetic resonance, carbon-hydrogen-nitrogen-sulfur analysis and hydroxyl value. The colour properties were checked using UV-vis spectrophotometry and density functional theory, while thermogravimetric analysis was used for the thermal degradation studies of both the dyes.

Findings

Water-soluble cardanol-based azo dyes were prepared successfully having good thermal stability, and the obtained results are being presented in this paper.

Originality/value

The originality lies between the use of cardanol as a bio-based resource for the synthesis of azo-dye and the obtained azo-dye has the pH-sensitivity.

Keywords

Acknowledgements

Authors would like to show sincere gratitude to the following people for providing support for DFT studies: 1. Mr Vardhan Satalkar (Department of Chemistry and Biochemistry, University of Oklahoma), 2. Mr Shaunak Shaikh (Department of Chemistry and Macromolecules Innovation Institute, Virginia Tech University), 3. Ms Nikita Kumari (School of Molecular Sciences and The Biodesign, Arizona State University).

Citation

Mestry, S.U., Mahajan, U.R., M., A. and Mhaske, S.T. (2021), "Development of novel pH-sensitive azo dyes from Cardanol as a bioresource", Pigment & Resin Technology, Vol. 50 No. 3, pp. 231-240. https://doi.org/10.1108/PRT-03-2020-0026

Publisher

:

Emerald Publishing Limited

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