Synthesis and Application of Some Azo and Azomethine Dyes Containing Pyrazolone Moiety

Abstract

3-Amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one (1) was used as starting material for the synthesis of a number of azo compounds 3a-3c and azomethine derivative 4. The deblocking of 3a-3c and 4 gave rise to 5a-5c and 6 in which a free amino was revealed. The diazonium salts of 5a-5c and 6 were coupled with several phenols to produce a number of bis azo compounds 7a-7c and 8a-8c with azomethine in position 4 and azoic group in position 3. The prepared dyes were structurally confirmed by elemental analysis, spectral methods and applied to different fibers (wool, polyester and blend of wool/polyester) as disperse dyes and their fastness properties were measured.

Synthesis and characterization of metal complexes of azo dye based on 5‐nitro‐8‐hydroxyquinoline and their applications in dyeing polyester fabrics

“…Total dyeing time was 90 min. It was then cooled to 60 °C and then after washing, dyed samples were rinsed and dried …”

New class of magenta dyestuffs based on azomethine pyrazolone disperse dyes: Synthesis, characterization, and dyeing performance on polyester fabrics with ultraviolet protection and pH-dependent properties

“…In accordance with literature procedures, the compounds 1,3-disubstituted-1H-pyrazol-5(4H)-ones 1a-h, 36 1,3-disubstituted-1H-pyrazole-4,5-diones derivatives 2a-h, 37 4-benzylidene-1,3-diaryl-1H-pyrazol-5(4H)-one 3a-h 38 and 4-phenylazo-1,3-diaryl-1H-pyrazol-5(4H)-one 4a-h 39 were synthesized. To synthesize a series of novel azomethine dyes, we tried three different methods: A, B, and C. 31,40 Actually, we found that method A was simple, had a short reaction time and had a high reaction rate and excellent yields.…”

“…29,30 In recent years, research on textile materials has paid great attention to the development of new azomethine dyes for dyeing various fabrics. 31,32 Due to the above and in order to obtain a type of attractive color and safe dyes, we have synthesized azomethine disperse dyes based on pyrazolone moiety which contain iminodiethanol groups by different routes to obtain dyes used for dyeing polyester fabrics.…”

Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics

“…For example, pyrazolin-5-ones are very important class of heterocycles, due to their potential pharmacological and biological applications [1][2][3][4][5][6][7][8][9]. Moreover, such heterocycles are extensively involved in the manufacture of commercial dyes, such as photographic dyes and textile dyes [10,11]. Azomethine dyes derived from pyrazolone are commonly used in color photography; usually these dyes are magenta in hue [12][13][14][15].…”