Synthesis of disperse dyes derived from 4-amino-N-decyl-1, 8-naphthalimide and their dyeing properties on polyester fabrics

Novel series of amphiphilic monoazo dyes were synthesized using 4-amino-N-decyl-1, 8-naphthalimide by coupling with different substituted anilines and naphthalenes in appropriate reaction condition. The intermediates and the dyes were purified by recrystallization methods. The structures of the newly synthesized intermediates and the dyes were confirmed from elemental analysis (CHN), FT-IR, H-1 and C-13 NMR, MS and UV spectroscopic techniques. Spectrophotometric investigations of the synthesized dyes in different solvents were carried out in order to obtain their absorption maxima, molar extinction coefficients and solvatochromic effects. These dyes were applied on polyester fabrics as disperse dyes using high temperature exhaust dyeing method. The relevant dyeing characteristics, such as buildup on fabrics, wash, perspiration and light fastness were evaluated. Fabrics dyed with these dyes furnished generally deep and bright intense hues ranging from light yellow to orange to light red. The colour fastness of the dyed fabrics to washing and perspiration was assessed to be very good, however, the light fastness was found to be poor, moderate to very good.