Synthesis of new azo dyes and metal complexes from some phenolic compounds and i̇nvestigation of spectroscopic and dyeing properties

In this study, it was aimed to synthesise new environmentally compatible azo dyestuff ligands from phenolic compounds such as gallic acid, protocatechuic acid and vanillic acid which have various biological activities such as antioxidant, antifungal, antiviral and anticancer by chelating method. Then, it was aimed to synthesise metal complexes from these azo dyestuff ligands, which are important in the textile industry, especially in the defence industry, with their high fastness and to determine their dyeing properties. 4-nitroaniline and 4-aminophenol were used in the synthesis of azo dyes ligands. As a result of the reaction of 6 different azo dyes with sulfate salts of transition metals (MnII, FeII, NiII, CuII, ZnII), 30 new metal complex dyes were synthesised. The synthesised dyestuffs were characterised by elemental analysis, 1H-NMR, 13C-NMR, FT-IR, UV-VIS, mass spectrometry (MS) and their thermal properties were determined by TGA/DTG analysis. UV-VIS measurements were carried out in 4 different solvents: dimethylformamide (DMF-polar aprotic), methanol (polar protic), pH:2 methanol and pH:12 methanol. According to NMR and UV-VIS data, the presence of azo-hydrazone tautomer structures of the synthesised dyes was observed. The structural characterisations of the synthesised metal complexes were determined according to UV-VIS, FT-IR, MS spectroscopic methods and elemental analysis, TGA/DTG results and it was determined that the coordination of the azo dyestuff with the metal has a ratio of 1:2 (Metal:Ligand). Wool and polyester fabrics were coloured with 36 synthesised dyestuff compounds under suitable conditions by using 1:15 flotte ratio. The colour codes of the dyed fabrics were determined according to the 'Farben Atlas' scale. In order to determine the washing fastness of the dyed wool and polyester fabrics, TS EN ISO 105-C09 standard method, TS EN ISO 105-X12 method for rubbing fastness and daylight method for light fastness were used and the results were evaluated by comparing with staining grey scale (washing and rubbing fastness), fading grey scale (washing and daylight fastness) and standard blue wool reference fabrics (daylight fastness). According to the results obtained, it was determined that the fastness properties of wool and polyester fabrics coloured with metal complex dyes were higher than those of fabrics dyed with ligand dyes.