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Said Benkhaya, Souad M'rabet, Ahmed El Harfi  Heliyon 

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Presentation on theme: "Said Benkhaya, Souad M'rabet, Ahmed El Harfi  Heliyon "— Presentation transcript:

1 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

2 Figure 1 Structure of the azo reactive dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

3 Figure 2 Structure of chrysoidine.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

4 Figure 3 Yellow basic dye.
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5 Figure 4 Structure of the orange dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

6 Figure 5 Orange IV. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

7 Figure 6 Structure of the yellow dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

8 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

9 Figure 8 Mordant black 17. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

10 Figure 9 Brown dye structure.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

11 Figure 10 Structure blue direct dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

12 Figure 11 Exemple se synthèse du colorant asymétrique.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

13 Figure 12 Structure of the orange direct dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

14 Figure 13 Structure of the direct red dye.
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15 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

16 Figure 15 Mording red procion M-2B.
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17 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

18 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

19 Figure 18 C.I.Reactive red 17. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

20 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

21 Figure 20 Azo red dye réactif Levafix E.
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22 Figure 21 Reaction of the active part of the vinyl sulfone-type.
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23 Figure 22 Fastening mechanism with cellulose fiber.
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24 Figure 23 Structure of the reactive blue dye 19.
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25 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

26 Figure 25 Structure of the dye C.I Reactive Red 221.
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27 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

28 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

29 Figure 28 Addition reactions on the azo group.
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30 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

31 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

32 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

33 Figure 32 Trans and Cis conjugated acids.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

34 Figure 33 Ammonium-azonium tautomerism.
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35 Figure 34 Azophenol-quinone hydrazone tautomerism.
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36 Figure 35 Form of tautomerism.
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37 Figure 36 Azophenol dye. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

38 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

39 Figure 38 Imino and azo form.
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40 Figure 39 Protonated tautomerism.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

41 Figure 40 Azo dyes 26. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

42 Figure 41 5-azo-thieno [2, 3-d] oxazoles dyes 27.
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43 Figure 42 Dispersed diazo dyes 38.
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44 Figure 43 Disazo disperse dyes 39.
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45 Figure 44 Azothiophene dyes 42.
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46 Figure 45 Synthesis of azo dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

47 Figure 46 Represents the preparation of symmetrical azo compounds.
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48 Figure 47 Azo compound. Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

49 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

50 Figure 49 Synthesis of nitrosated derivatives.
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51 Figure 50 Electrophilic aromatic substitution mechanism.
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52 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

53 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

54 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

55 Figure 54 Synthesis of arylazo pyridone dye.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

56 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

57 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

58 Figure 57 Possible tautomeric structures of dye 1a.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

59 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

60 Figure 59 Synthesis of azo-chromene.
Heliyon 2020 6, DOI: ( /j.heliyon.2020.e03271) Copyright © 2020 The Author(s) Terms and Conditions

61 Figure 60 Different structure of compound A.
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62 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

63 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

64 Figure 63 Different structure of compound IV.
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65 Figure 64 Different structure of compound V.
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66 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

67 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

68 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

69 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

70 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

71 Figure 70 Diagram of a noncovalent dye-polymer bond.
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