B. E. Ezema et al /Int.J. ChemTech Res. 2016,9(1),pp 169-173.
(i) aq. NaHCO3
+
HOOC N NClHOOC NH2 (ii) aq.NaNO2
(iii) conc. HCl
13
(i) aq. NaHCO3
+
HOOC NH2
HOOC N NCl
(ii) aq. NaNO2 H O (iii) conc. HCl
HO 2
4
The diazonium salt 3 was then coupled respectively with 8-hydroxyquinoline 5, 5-nitroso-8hydroxyquinoline 6, 5-nitro-8-hydroxyquinoline 7 and 5-chloro-8-hydroxyquinoline 8 in alkaline medium of 10% KOH to produce excellent micro crystalline azo dyes: 4-(8-hydroxyquinolin-5-ylazo)benzoic acid 9, 4-(8hydroxy-5-nitrosoquinolin-7-azo)benzoic acid 10, 4-(8-hydroxy-5-nitroquinolin-7-azo)benzoic acid 11 and 4(5-chloro-8-hydroxyquinolin-7-azo)benzoic acid 12 (scheme 2);
Again the diazonium salt 4 was also coupled with 8-hydroxyquinoline 5, 5-nitroso-8-hydroxyquinoline 6, 5-nitro-8-hydroxyquinoline 7 and 5-chloro-8-hydroxyquinoline 8 in alkaline medium of 10% KOH to produce another four derivatives of excellent micro crystalline azo dyes: 4-(8-hydroxyquinolin-5-azo)-2hydroxybenzoic acid 13, 4-(8-hydroxy-5-nitrosoquinolin-7-azo)-2-hydroxybenzoic acid 14, 4-(8-hydroxy-5nitroquinolin-7-azo)-2-hydroxybenzoic acid 15 and 4-(5-chloro-8-hydroxyquinolin-7-azo)-2-hydroxybenzoic acid 16 respectively (scheme 3);
Scheme 3
B. E. Ezema et al /Int.J. ChemTech Res. 2016,9(1),pp 169-173.
The structures of the dyes were ascertained based on their spectral data: in the FT-IR spectrum, all the dyes showed very broad band between 3590-2700 cm-1 assigned to the O-H groups, 1700-1670 for the C=O groups, 1610-1550 assigned for the –N=N- of the azo groups. The elemental analysis of the compounds was in agreement with the molecular formulas: (9, C16H11N3O3), (10, C16H10N4O4), (11, C16H10N4O5), (12, C16H10ClN3O3), (13, C16H11N3O4), (14, C16H10N4O5), (15, C16H10N4O6) and (16, C16H10ClN3O4). The 1H-NMR also gave further support of the structures.
Dyeing of silk and wool fabrics with the synthesized azo dyes:
Dyeing was carried out in aqueous solution of DMF/Acetone/acetic acid. They gave very good to excellent shades on the silk and wool fabrics and showed excellent wash fastness and good sublimation fastness base on the international geometric gray standard (1 and 5 for poor and excellent respectively) as presented in the table.
Table : fastness properties of synthesized heterocyclic azo dyes
Dye no | Wash fastness (1-5) Silk, wool | Stain on undyed fabric after washing (1-5) Silk/cotton wool/cotton | Sublimation fastness (1-5) Silk, wool | Stain on undyed fabric after sublimation (1-5) Polyester, cotton |
---|---|---|---|---|
9 | 4-5, 4.0 | 4.0 4-5 | 4-5, 4.5 | 4-5 5 |
10 | 4-5, 4.5 | 5.0 4-5 | 5.0, 4,5 | 5 4-5 |
11 | 4-5, 4.5 | 4-5 5.0 | 4-5, 4.0 | 4 4 |
12 | 4-5, 4.0 | 4-5 4.0 | 4-5, 4.5 | 4-5 4 |
13 | 5.0 4.5 | 4-5 4.0 | 4.0, 4.5 | 4-5 5 |
14 | 5.0, 4.0 | 4-5 5.0 | 4-5, 4.0 | 4-5 5 |
15 | 5.0, 4,5 | 4-5 5.0 | 4-5. 4.5 | 4-5 5 |
16 | 5.0, 5.0 | 4-5 5.0 | 4-5, 4.0 | 4-5 5 |
The prepared dyes showed good to excellent fastness properties and therefore can be used as industrial colourants both in the textile and plastic industries.
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B. E. Ezema et al /Int.J. ChemTech Res. 2016,9(1),pp 169-173.
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