The objective of the study was to synthesize imino derivatives of phenoxazines and then study their dyeing properties. 6-Chloro-10-aminobenzo[a]phenoxazine-5-one 3 was prepared by condensation of 2,4-diaminophenol 1 with 2,3-dichloro-1,4-naphthoquinone 2 in an alkaline medium. Further treatment of 3 with 4-chlororbenzaldehyde 4, 4-fluorobenzaldehyde 5, 4-amino-3,5-dimethylbenzaldehyde 6, 4-methoxybenzaldehyde 7 and 4-methylbenzaldeyde 8, respectively gave the derivatives: 6-Chloro-10-(4-chlorophenylimino)benzo[a]phenoxazin-5-one 9, 6-Chloro-10-[(4-fluorophenylimino)benzo [a]phenoxazine-5-one 10,10-{(4-amino-3,5-dimethylbenzylidine)amino}-6-chlorobenzo[a] phenoxazine-5-one 11, 6-Chloro-10-{(2-methoxybenzylidine)amino}benzo[a]phenoxazine-5-one 12, 6-Chloro-10-(4-methylphenyl-imino) benzo[a]phenoxazin-5-one 13. These derivatives were characterised using UV-visible, FT-IR, 1H-NMR spectroscopy and elemental analytical data. The results from the evaluation of the dyeing fastness properties of these compounds showed that they have moderate to good fastness properties on cotton fibres.
