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Synthesis and Spectral Properties of Symmetrical and Asymmetrical 3-Cyano-1,5-diarylformazan Dyestuffs for Dyeing Polyester Fabrics

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Organic chemistry

Abstract

In this study, we report on a general synthetic approach to both symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyes. The reaction of enaminonitrile with aromatic diazonium salts in slightly acidic medium affords arylhydrazonals as stable intermediate that are readily converted into asymmetrical formazans via second azo-coupling in a weak alkaline medium. Symmetrical formazan dyestuffs are synthesized directly via double azo-coupling of the key intermediate 3-piperidinylacrylonitrile with the corresponding diazonium salts in weak alkaline medium using sodium acetate as a weak base. The structures of the prepared dyestuffs and intermediates are demonstrated by elemental analysis (C, H, N), 1H and 13C NMR, FTIR and GC-MS spectroscopic techniques. The prepared formazan disperse colorants are applied to dye polyester fabric to give satisfactory fastness properties to wash, perspiration, rubbing and light.

DOI

10.21608/ejchem.2017.1479.1103

Keywords

Cyanoenamine, Hydrazonal, Formazan, Azo-coupling, dyeing, polyester

Authors

First Name

Tawfik

Last Name

Khattab

MiddleName

-

Affiliation

Dyeing, Printing and Auxiliaries Department, Textile Research Division, National Research Centre, Cairo 12622, Egypt

Email

tkhattab@kent.edu

City

Cairo

Orcid

0000-0001-7834-4952

First Name

Karima M.

Last Name

Haggag

MiddleName

-

Affiliation

Dyeing, Printing and Auxiliaries Department, Textile Research Division, National Research Centre, Cairo 12622, Egypt

Email

-

City

-

Orcid

-

Volume

60

Article Issue

Conference Issue (The 8th International Conference of The Textile Research Division (ICTRD 2017), National Research Centre, Cairo 12622, Egypt.)

Related Issue

678

Issue Date

2017-12-01

Receive Date

2017-08-13

Publish Date

2017-12-01

Page Start

33

Page End

40

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_4060.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=4060

Order

3

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Synthesis and Spectral Properties of Symmetrical and Asymmetrical 3-Cyano-1,5-diarylformazan Dyestuffs for Dyeing Polyester Fabrics

Details

Type

Article

Created At

22 Jan 2023