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

New Mn(II), Ni(II), Co(II) and Cu(II) complexes of an azo dye ligand based on p-phenylenediamine with 5-nitro-8-hydroxyquinoline were synthesized and characterized using elemental analysis, inductive coupled plasma analysis, molar conductance, powder X-ray diffraction, thermogravimetric analysis, magnetic moment measurements, and infrared, 1 H NMR, electron ionization mass and UV-visible spectral studies. The spectral and analytical data reveal that the azo dye ligand acts as a monobasic bidentate ligand via deprotonated OH and nitrogen atom of the quinoline ring. The data support the formulation of all complexes with a 2:1 ligand-to-metal ratio, except the Mn(II) complex that has a mononuclear formula. All complexes have an octahedral structure. The molar conductance data reveal that all the metal complexes are non-electrolytic in nature. From the X-ray data, the average particle size of the ligand and its complexes is 0.32-0.64 nm. The colour fastness to light, washing, perspiration, sublimation and rubbing of the prepared ligand and its complexes on polyester fabrics and colorimetric properties were measured. The results reveal that the ligand and its complexes have a good to moderate affinity to polyester fibres.

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

Section: Methodsmentioning

confidence: 99%

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

El-Wakiel

Rizk

Ibrahim

2017

Applied Organom Chemis

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“…Owning to their wide distribution in nature and essentiality, we have published many papers in this field [15–18]. In addition to its biological activities, pyrazolone is extensively involved in the manufacture of commercial dyes, such as photographic and textile dyes [19–21].…”

Section: Introductionmentioning

confidence: 99%

Ultrasonic‐Assisted condensation of aromatic and aliphatic aldehydes with 3‐(Thiophen‐2‐yl)‐5‐Pyrazolone: Synthesis, characterization and Stereoselective application

Rizk

Noser

Ibrahim

et al. 2022

Journal of Heterocyclic Chem

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A green and efficient protocol for a one-pot condensation of 1-(2,4-dinitrophenyl)-3-(thiophen-2-yl)-1H-pyrazol-5(4H)-one (1) with aromatic and aliphatic aldehydes in different ratios to synthesize novel heterocyclic compounds containing pyrazolone and pyranopyrazole moieties. The reactions were conducted using the ultrasonic and traditional methods. The sonication ensured more efficiency in the rate and yield of the reactions. The structures of the synthesized compounds were elucidated by different spectroscopic methods. Additionally, an enantioselective synthesis of (R)-and (S)-α-alkylated acid was achieved using 1-(2,4-dinitrophenyl)-4-(hydroxymethyl)-3-(thiophen-2-yl)-1H-pyrazol-5(4H)-one (6) as chiral auxiliary, (S)-4-Methyl-5-nonanol the aggregation pheromone of red palm weevil was efficiently prepared and used for trapping the red palm weevil.

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“…Especially when they are applied to polyamide and polyester group textile materials, its preferability levels are high along with their good to excellent fastness degrees [1][2][3][4]. Pyrazole derivative groups, among the dispersed azo dyestuffs, which are the most commonly used group in the dyeing of hydrophobic fibers, have recently become very popular [5][6][7][8][9][10][11]. Pyrazole group is characterized by being the most frequently used heterocyclic compound in many application fields.…”

Section: Introductionmentioning

confidence: 99%

Application of some novel pyrazole disperse dyes to synthetic fabrics

Bakan

Karcı

2022

Usak University Journal of Engineering Sciences

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In this study, 8 novel pyrazole disperse dyes which were synthesized in our previous work [1] were applied to polyethylene terephthalate (PET), poly (lactic acid) (PLA) and polyamide 6.6 (PA 6.6) fiber fabrics and their colorimetric and fastness properties were evaluated. The measured a*, b* and hue angle (ho) values of all dyed fabrics exhibited yellow, orange and red colour shades. Quite high colour strength values (K/S) were measured particularly for dyes containing substitute groups; p-OCH3 and o-OCH3. Shade changes of all fabrics after standard washing and sublimation tests were in the commercially adequate range. All dyed PET, PLA and PA 6.6 fabrics exhibited commercially acceptable fastness staining performances with very good to excellent levels. Synthesized novel disperse dyestuffs led to moderate to high light fastness levels particularly in the case of PLA and PET fabrics.

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

Cited by 16 publications

References 23 publications

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

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

Ultrasonic‐Assisted condensation of aromatic and aliphatic aldehydes with 3‐(Thiophen‐2‐yl)‐5‐Pyrazolone: Synthesis, characterization and Stereoselective application

Application of some novel pyrazole disperse dyes to synthetic fabrics

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