A facile synthesis and tautomeric structure of novel 4‐arylhydrazono‐3‐(2‐hydroxyphenyl)‐2‐pyrazolin‐5‐ones and their application as disperse dyes

Metwally, M. A.; Bondock, Samir; El-Desouky, El-Sayed I.; Abdou, Moaz M.

doi:10.1111/cote.12052

Cited by 25 publications

(15 citation statements)

References 49 publications

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“…This can be attributed to the increase in polarity of the dyes as well as large molecular size (Metwally et al, 2013). Furthermore, there was no staining on the adjacent multi-fibre fabric in the case of dry crocking.…”

Section: Discussionmentioning

confidence: 92%

Synthesis and application of hetaryl disazo disperse dyes derived from 4-amino-2-chloro-6,7-dimethoxyquinazoline and 3-chloroaniline on polyester fabric

Otutu¹,

Ossai²,

Ameuru³

2015

Int. J. Bio. Chem. Sci

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In an attempt to find more environmentally friendly azo dyes, the synthesis and application of disazo disperse dye derivatives of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 3-chloroaniline on polyester fabric are reported. The disazo dyes were synthesized via diazotisation of 3-chloroaniline and coupled with 4-amino-2-chloro-6,7-dimethoxyquinazoline to afford an intermediate azo dye. This intermediate was further diazotised in concentrated sulphuric acid and followed by coupling reactions with various coupling components such as 1,3-diyhydroxybenzene, 2-amino-6-methylbenzonitrile, 3-amino-5-methyl-prazole, 1-napthol and 7-methoxy-2-naphthol to give the disazo disperse dyes. The basic fastness properties (light fastness wash fastness heat and rubbing fastness) of the dyes on polyester fibre were discussed in terms of their chemical structures. All the synthesized disazo disperse dyes were characterized on the basis of their spectral analyses, IR, 1 H NMR, 13 C NMR and UV-visible spectroscopic data. The light fastness results were observed to be good ratings (5) and very good ratings (5/6). The sublimation test results gave excellent ratings of (5). Also, it was found that the wash fastness property, which is an indicator whether a dye could have affinity for a textile fabric or not, have excellent ratings of 5. From these results, it can be concluded that the best of these disazo dye compounds could be commercially important in the textile industry.

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Section: Discussionmentioning

confidence: 92%

Synthesis and application of hetaryl disazo disperse dyes derived from 4-amino-2-chloro-6,7-dimethoxyquinazoline and 3-chloroaniline on polyester fabric

Otutu¹,

Ossai²,

Ameuru³

2015

Int. J. Bio. Chem. Sci

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“…Two selected pyrazoline derivatives Pz1 and Pz2 were prepared according to our previous protocol. 31 , 32…”

Section: Methodsmentioning

confidence: 99%

Multifunctional Aspects of the Synthesized Pyrazoline Derivatives for AP1 5L X60 Steel Protection Against MIC and Acidization: Electrochemical, In Silico, and SRB Insights

Abbas

Eid²,

Abdou

et al. 2021

ACS Omega

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The inhibitory impact of low-cost synthesized pyrazoline derivatives named Pz series ( Pz1 and Pz2 ) on the corrosion of API 5L X60 carbon steel in 5 M HCl was inspected to serve as corrosion inhibitors against such a solution for its usage in the oilfield well acidization process. Also, the same compounds were unitized as biocides for sulfate-reducing bacteria (SRBs) to inhibit the microbial-induced corrosion effect. This study was conducted via several electrochemical techniques, namely, electrochemical potentiodynamic polarization (EP) and electrochemical impedance spectroscopy (EIS), in addition to computational density functional theory (DFT). The inhibition efficiency (IE) of Pz series on the corrosion of 5L X60 carbon steel in 5 M HCl was found to increase whenever the Pz series molecule concentration was increased. EP measurements revealed that Pz1 and Pz2 have both cathodic and anodic features (mixed inhibitor) and their corrosion IEs were around 90%. The physicochemical properties of the Pz1 and Pz2 compounds were studied using Langmuir adsorption isotherms, where the equilibrium adsorption data were found to follow it accurately. EIS outputs were found to comply with the values obtained from EP. Scanning electron microscopy was used to examine the topographic anisotropy between the inhibited and uninhibited 5L X60 carbon steel samples to double-check the electrochemical findings. DFT calculations and Monte Carlo simulations were utilized to predict the behavior of inhibitors and to rationalize the experimental results. The serial dilution bioassay technique was used to assess the Pz series as potential biocides to counter the effect of SRBs in compliance with the TM0194-2014-SG standard test method, and the results showed the potency of Pz series in inhibiting such bacterial growth.

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“…All of the 3‐aryl‐ and 3‐hetaryl‐azo‐ 4‐hydroxyquinolin‐2(1 H )‐one dyes were synthesised from the reaction of the appropriate diazonium salt with 6, 8‐dichloro‐4‐hydroxyquinolin‐2(1 H )‐one 4 using classical reported procedures for the synthesis of azo compounds . The crude products were purified by recrystallisation with DMF‐H 2 O and then analysed.…”

Section: Methodsmentioning

confidence: 99%

“…All of the 3-aryl-and 3-hetaryl-azo-4-hydroxyquinolin-2(1H)-one dyes were synthesised from the reaction of the appropriate diazonium salt with 6, 8-dichloro-4-hydroxyquinolin-2(1H)-one 4 using classical reported procedures for the synthesis of azo compounds. [27][28][29][30] The crude products were purified by recrystallisation with DMF-H 2 O and then analysed. The structure of the dyes was confirmed by UV-vis, FT-IR and 1 H NMR spectroscopic techniques and elemental analysis.…”

Section: Synthesis Of the Arylazo Dyes 5-18mentioning

confidence: 99%

Aryl and heteroaryl azo dyes derived from 6, 8‐dichloro‐4‐hydroxyquinolin‐2 (1H)‐one: synthesis, characterisation, solvatochromism and spectroscopic properties

Rufchahi

Gilani

2019

Coloration Technology

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In this research study, 6, 8‐dichloro‐4‐hydroxyquinolin‐2(1H)‐one was prepared by the thermal cyclocondensation of 2‐(2, 4‐dichlorophenylcarbamoyl) acetic acid or N, Nʹ‐bis(2,4‐dichlorophenyl)malonamide at 140‐150°C in polyphosphoric acid, resulting in a yield of 48%. This compound was then coupled with a series of diazonium salts derived from aromatic and heteroaromatic amines for synthesis of the corresponding azo dyes. The structures of the compounds were confirmed using elemental analysis as well as ultraviolet‐visible, Fourier Transform‐infrared and proton nuclear magnetic resonance spectroscopy. The effects of organic solvents with different polarities, pH values and substituents of the diazotising components on the maximum absorption wavelength of the colorants were discussed and evaluated in detail. The acidity constants (pKa) of the dyes were also determined using the spectrophotometric method in an ethanol‐water mixture (80:20, v/v) at 20‐23°C.

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A facile synthesis and tautomeric structure of novel 4‐arylhydrazono‐3‐(2‐hydroxyphenyl)‐2‐pyrazolin‐5‐ones and their application as disperse dyes

Cited by 25 publications

References 49 publications

Synthesis and application of hetaryl disazo disperse dyes derived from 4-amino-2-chloro-6,7-dimethoxyquinazoline and 3-chloroaniline on polyester fabric

Synthesis and application of hetaryl disazo disperse dyes derived from 4-amino-2-chloro-6,7-dimethoxyquinazoline and 3-chloroaniline on polyester fabric

Multifunctional Aspects of the Synthesized Pyrazoline Derivatives for AP1 5L X60 Steel Protection Against MIC and Acidization: Electrochemical, In Silico, and SRB Insights

Aryl and heteroaryl azo dyes derived from 6, 8‐dichloro‐4‐hydroxyquinolin‐2 (1H)‐one: synthesis, characterisation, solvatochromism and spectroscopic properties

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