title: 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.
authors.affiliation: Dept. of Polymer Engineering and Color Technology, Amirkabir University of Technology, Tehran, Iran.
authors.forename: Hanieh
authors.initials: H
authors.lastname: Shaki
authors.affiliation: Dept. of Organic Colorants, Inst. for Color Science and Technology, Tehran, Iran.|Center of Excellence for Color Science and Technology, Tehran, Iran.
authors.forename: Kamaladin
authors.initials: K
authors.lastname: Gharanjig
authors.affiliation: Dept. of Polymer Engineering and Color Technology, Amirkabir University of Technology, Tehran, Iran.
authors.forename: Alireza
authors.initials: A
authors.lastname: Khosravi
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001391:Azo Compounds / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004396:Coloring Agents / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D053644:Naphthalimides / Q000737:chemistry* / Q000494:pharmacology; D013053:Spectrophotometry; D013784:Textiles
chemical_list: D000900:Anti-Bacterial Agents; D001391:Azo Compounds; D004396:Coloring Agents; D053644:Naphthalimides
keywords: antimicrobial activity; azo disperse dyes; characterization; dyeing properties; spectrophotometric properties; synthesis