Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides

Abstract

A series of novel disperse dyes containing azo group were synthesized through a diazotization and coupling process. The 4-amino-N-2-aminomethylpyridine-1,8-naphthalimide was diazotized by nitrosylsulphuric acid and coupled with various aromatic amines such as N,N-diethylaniline, N,N-dihydroxyethylaniline, 8-hydroxyquinoline, and 2-methylindole. Chemical structures of the synthesized dyes were characterized by Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), proton nuclear magnetic resonance ((1) H NMR), carbon nuclear magnetic resonance ((13) C NMR), elemental analysis, and ultraviolet-visible (UV-visible) spectroscopy. The spectrophotometric data of all dyes were evaluated in various solvents with different polarity. Eventually, the dyes were applied on polyamide fabrics in order to investigate their dyeing properties. The fastness properties of the dyed fabrics such as wash, light, and rubbing fastness degrees were measured by standard methods. Moreover, the color gamut of the synthesized dyes was measured on polyamide fabrics. Results indicated that some of the synthesized dyes were able to dye polyamide fabrics with deep shades. They had very good wash and rubbing fastness degrees and moderate-to-good light fastness on polyamide fabrics. The antibacterial and antifungal activities of the synthesized dyes were evaluated in soluble state and on the dyed fabrics. The results indicated that dye 2 containing N,N-dihydroxyethylaniline as coupler had the highest activity against all the bacteria and fungi used.

A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes

“…The presence of a stable chromophore azo group ( -N = N -) conjugated with an aromatic ring creates a molecule with intense and highly stable color in different solvents throughout the visible region of light [35][36][37][38] . Although numerous papers have described the synthesis and properties of azo-8-hydroxyquinoline [39][40][41][42] , there is no report on the synthesis of similar 5-hydroxyquinoline (5HQ) azo analogous ( Fig. 1 B).…”

Synthesis and characterization of azobenzene derived from 8-aminoquinoline in aqueous media

“…Azobenzenes are an important class of organic compounds that are widely used as organic dyes (1, 2), protein probes (3,4), chemosensors (5,6), cosmetics (7)(8)(9), nanotubes (10,11) and polymers (12)(13)(14). Due to the presence of N-N linkages, they have been used for pharmacological applications such as antiviral, anti-inflammatory, antimicrobial, antitumor, antidiabetics, and antituberculotic (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25). Beyond their potential in these application areas, azo-compounds are mostly used as dyes.…”

Application of some novel pyrazole disperse dyes to synthetic fabrics

“…in the medical field [12][13][14][15][16][17][18][19][20][21]. Besides, it is widely used for dyeing synthetic based fabrics for textile industry due to their wide and different color choices [22][23][24][25]. Color and color fastness characteristics of synthetic fibers dyed with these dyes displayed satisfying results [26][27][28][29][30][31].…”