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Synthesis and Characterization of Novel Monoazo N‐Ester‐1,8‐Naphthalimide Disperse Dyestuffs
Author(s) -
Gharanjig Kamaladin,
Arami Mokhtar,
Rouhani Shohre,
Bahrami Hajir,
Movassagh Barahman,
Mahmoodi Niyaz Mohammad
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700147
Subject(s) - chemistry , polyester , acenaphthene , fourier transform infrared spectroscopy , polymer chemistry , nitro , proton nmr , copolymer , nuclear chemistry , organic chemistry , polymer , chemical engineering , alkyl , pyrene , engineering
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 1 H‐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.