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Classifications, properties, recent synthesis and applications of azo dyes
Said Benkhaya, Souad M'rabet, Ahmed El Harfi Heliyon Volume 6, Issue 1, (January 2020) DOI: /j.heliyon.2020.e03271 Copyright © 2020 The Author(s) Terms and Conditions
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Figure 1 Structure of the azo reactive dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 2 Structure of chrysoidine.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 3 Yellow basic dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 4 Structure of the orange dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 5 Orange IV. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 6 Structure of the yellow dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 7 Illustrates the red dye with their mordant (a), the blue dye (b) and the blue dye (c). Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 8 Mordant black 17. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 9 Brown dye structure.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 10 Structure blue direct dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 11 Exemple se synthèse du colorant asymétrique.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 12 Structure of the orange direct dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 13 Structure of the direct red dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 14 Synthesis route of an example of monochlorotriazine dyes.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 15 Mording red procion M-2B.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 16 Structure of the Cibacron shiny red dye B.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 17 Mechanism of fixing and hydrolysis of the mono and dichloro triazine dye. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 18 C.I.Reactive red 17. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 19 Dye type 5-chloro-2, 4-difluoropyrimidine.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 20 Azo red dye réactif Levafix E.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 21 Reaction of the active part of the vinyl sulfone-type.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 22 Fastening mechanism with cellulose fiber.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 23 Structure of the reactive blue dye 19.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 24 Structure of the dye C.I. Reactive Blue 171.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 25 Structure of the dye C.I Reactive Red 221.
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Figure 26 Structure of the C.I. Reactive Red dye 194.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 27 Structure of the mono fluoro triazine-sulphatoethylsulfone dye. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 28 Addition reactions on the azo group.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 29 Chemical structures of (c), (d), (e) and (f).
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 30 Diagram of the substantivity of azo dyes according to their reactive part. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 31 Form Z and E of the azobenzene molecule.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 32 Trans and Cis conjugated acids.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 33 Ammonium-azonium tautomerism.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 34 Azophenol-quinone hydrazone tautomerism.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 35 Form of tautomerism.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 36 Azophenol dye. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 37 Strucure of azo-acétoacétanilide, azo-pyrazolone and azo-pyridone. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 38 Imino and azo form.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 39 Protonated tautomerism.
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Figure 40 Azo dyes 26. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 41 5-azo-thieno [2, 3-d] oxazoles dyes 27.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 42 Dispersed diazo dyes 38.
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Figure 43 Disazo disperse dyes 39.
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Figure 44 Azothiophene dyes 42.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 45 Synthesis of azo dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 46 Represents the preparation of symmetrical azo compounds.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 47 Azo compound. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 48 Simple reaction of the synthesis of azo dyes.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 49 Synthesis of nitrosated derivatives.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 50 Electrophilic aromatic substitution mechanism.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 51 Compound 1 coupling reaction with benzene diazonium chloride and forms A, B, and C. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 52 Coupling reaction of 1 with diazotized 4-methylaniline.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 53 Coupling reaction of 1 with diazotized 4-chloroaniline.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 54 Synthesis of arylazo pyridone dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 55 New azo– hydrazone tautomerism in azo dyes.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 56 Shows different possibilities of the structure of 1a-1e.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 57 Possible tautomeric structures of dye 1a.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 58 Possible tautomeric forms of prepared dyes 1b–1e.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 59 Synthesis of azo-chromene.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 60 Different structure of compound A.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 61 Synthesis of reactive azo dyes from 2-amino-7-Hydroxy-4-phenyl-4H-chromene-3-carbonitrile through various alternative routes. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 62 Synthetic routes to some azo dyes from 2-amino- thiophenes and 2-aminothiazole. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 63 Different structure of compound IV.
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Figure 64 Different structure of compound V.
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Figure 65 Diagram of the preparation of polymeric dyes by copolymerization of colored monomers. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 66 Synthesis of an azo dye bearing N-aryl maleimides and their free radicals of polymerization. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 67 Synthesis of a derivative of polymerizable azo dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 68 Fixing molecule of the dye on polymer.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 69 Step-wise fixing of an azo dye to poly (vinylamine).
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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Figure 70 Diagram of a noncovalent dye-polymer bond.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions
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