New disazo pyrazole disperse dyes: Synthesis, spectroscopic studies and tautomeric structures

Karcı, Fikret; Bakan, Emine

doi:10.1016/j.molliq.2015.02.032

Cited by 21 publications

(7 citation statements)

References 34 publications

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“…The absorption ability of these dyes substituted with electronwithdrawing and electron-donating groups at their o-, m-and p-positions was examined in detail. 116 These synthesized yellow-red dyes were applied to PLA, PET, and polyamide (PA) 6.6 fibers, resulting in quite high color yield on PLA and PET fabrics with high K/S values leading to medium to heavy depth of shades at only 2% dye concentration. PLA and PET fabrics presented higher color strength and darker shades than PA 6.6 fabrics, while the light fastness of PET fabric was better than PLA and PA 6.6 fabrics.…”

Section: Dyeingmentioning

confidence: 99%

Poly(lactic acid) fibers, yarns and fabrics: Manufacturing, properties and applications

Yang

Zhang

et al. 2020

Textile Research Journal

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Poly(lactic acid) (PLA) fiber was developed more than a decade ago. It has been regarded as the most promising sustainable and biodegradable fiber to replace conventional polyethylene terephthalate (PET) polyester fiber in textile products. This paper reviews recent developments in PLA polymerization, PLA filament and fiber spinning, staple yarn spinning, fabric production, dyeing and finishing and aftercare procedures. The properties of PLA fiber are broadly similar to those of PET fiber; however, the properties of PLA fiber that differ, including thermal degradation and low hydrolytic resistance to strong alkaline, significantly affect the method selection and parameter setting of production and processing of PLA fibers and fabrics. PLA filaments are mainly produced by two-step melt spinning to get fibers with stable quality, but degradation at high temperature is still a problem. PLA staple yarns are normally spun using ring spinning. Currently existing knitting or weaving techniques can be used to produce PLA fabrics. PLA fabrics can be dyed with disperse dyes at 110°C, but their color fastness and shades are different from PET fabrics when using the same dyes. The scouring and dyeing of PLA/cotton blended fabrics and the reductive clearing after dyeing remain to be improved. As a new fiber, the entry of PLA fiber into the textile market faces difficult challenges as well as great opportunities in the future.

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Section: Dyeingmentioning

confidence: 99%

Poly(lactic acid) fibers, yarns and fabrics: Manufacturing, properties and applications

Yang

Zhang

et al. 2020

Textile Research Journal

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“…The studies in which pyrazole has been used as a heterocyclic coupling component have grown in importance and are frequently encountered in the literature, especially in recent years. 16,[18][19][20][21][22][23] The fact that the various pyrazole derivatives have been used in pharmacology, agricultural chemistry and the dye industry has resulted in the improvement of new synthetic procedures for the synthesis of these compounds. Condensation of β-enaminonitriles and β-ketoesters with hydrazine is one of the most widely used methods for the synthesis of aminopyrazoles and pyrazolones, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and absorption properties of five new heterocyclic disazo dyes containing pyrazole and pyrazolone and their acute toxicities on the freshwater amphipod Gammarus roeseli

Demirçalı

Karcı

Sari

2021

Coloration Technology

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In this study, five new heterocyclic disazo dyes containing pyrazole and pyrazolone were synthesised (3a-3e). The synthesised disazo dyes were characterised by elemental analysis and Fourier Transform-infrared and proton nuclear magnetic resonance spectroscopy. The effects of two different solvents upon the absorption ability of the dyes substituted with electron-withdrawing and electron-donating groups were examined in detail. In addition, the acute toxicity of each synthesised azo dye was evaluated using a short-term bioassay with Gammarus roeseli (Crustacea: Amphipoda) for 48 hours. According to the evaluations, the dyes 3a, 3b and 3d were categorised as slightly toxic, and the dyes 3c and 3e as practically non-toxic. Considering the toxicity of the dye 3a, it was determined that the substitution of the electron-withdrawing group in the azo dye resulted in more toxicity, while the substitution of the electrondonating group resulted in less toxicity. It was also found that the presence of the strongly electron-withdrawing group resulted in the azo dye becoming more toxic in comparison with the presence of the weakly electron-withdrawing group, but that the presence of the strongly electron-donating group resulted in the azo dye becoming less toxic in comparison with the presence of the weakly electron-donating group. It is contended that this study is novel and of great importance in terms of synthesising new azo dyes, investigating their absorption properties and assessing their acute toxicities.

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“…Due to their chemical significance and spectroscopic properties, hetarylazo dyes were studied extensively by spectroscopic and theoretical methods. Their higher tinctorial strength and brighter dyeing make azo dyes based on heterocyclic amines superior than aniline based azo dyes [23][24][25][26][27][28]. Some hetarylazopyrazolone dyes have not only potential use as dye stuff, but also other potential nontextile applications such as optical materials [29].…”

Section: Introductionmentioning

confidence: 99%

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Aktan

Uyar

2017

Journal of Chemistry

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In this study, the synthesized coupling component 1-(2-benzothiazolyl)-3-methylpyrazol-5-one reacted with diazotised heterocyclic amines to afford six novel hetarylazopyrazolone dyes. These azo dyes based on benzothiazole and benzimidazole ring systems were characterized by spectral methods and elemental analyses. The solvatochromic behaviors of these dyes in various solvents were evaluated. The ground state geometries of the dyes were optimized using density functional theory (DFT). Solvent, acid-base, and substituent influences on the wavelength of the maximum absorption were examined in detail. Time-dependent density functional theory (TD-DFT) calculations were performed to obtain the absorption spectra of the dyes in various solvents and the results compared with experimental values. Besides, frontier molecular orbitals (FMO) analysis for the dyes is also described from the computational process.

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New disazo pyrazole disperse dyes: Synthesis, spectroscopic studies and tautomeric structures

Cited by 21 publications

References 34 publications

Poly(lactic acid) fibers, yarns and fabrics: Manufacturing, properties and applications

Poly(lactic acid) fibers, yarns and fabrics: Manufacturing, properties and applications

Synthesis and absorption properties of five new heterocyclic disazo dyes containing pyrazole and pyrazolone and their acute toxicities on the freshwater amphipod Gammarus roeseli

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

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