54(4), 2007, pp.1021-1028

Synthesis and Characterization of Novel Monoazo N-ester-1,8-naphthalimide Disperse Dyestuffs

Kamaladin Gharanjig, Mokhtar Arami,* Shohre Rouhani, Hajir Bahrami, Barahman Movassagh, Niyaz Mohammad Mahmoodi

Amirkabir University of Technology, Faculty of Textile Engineering, P.O. Box 15875-4413, Tehran-Iran

Abstract.     Five novel monoazo disperse dyestuffs based on N-ester-1,8-naphthalimide were synthesized. Acenaphthene was nitrated, then oxidized to 4-nitro-1,8-naphthalic anhydride. 4-Nitro-1,8-naphthalic anhydride was reacted with methyl and ethyl glycinate in alcoholic media, followed with reduction. 4-Amino-N-methyl and ethyl glycinate-1,8-naphthalimide were obtained. These products were diazotized and coupled with appropriate aromatic amines to give bluish-red or violet dyestuffs. All intermediates and dyestuffs were purified and characterized by 1H-NMR, FTIR, DSC, UV-VIS and Elemental Analysis. Dispersion of dyestuffs was prepared in water and applied to polyester fabrics. The dyed fabrics showed that four of the synthesized dyestuffs were suitable for coloring polyester fibers, producing deep bluish red with very good build up properties.

Keyword:  Disperse dyestuffs; 4-Amino-N-alkylglycinate-1,8-naphthalimide; Azo dyestuffs; Dyeing; Diazotization; Coupling.