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1 – 10 of 369Rahul Patil, Lina Jadhav, Nikhil Borane, Satyendra Mishra and Vikas Patil
Here, diazo coupling reaction was imparted on chemically inert lignin isolated from natural resources. Activated lignin was coupled with the diazotised aniline, m-nitroaniline…
Abstract
Purpose
Here, diazo coupling reaction was imparted on chemically inert lignin isolated from natural resources. Activated lignin was coupled with the diazotised aniline, m-nitroaniline, p-nitroaniline-, and p-anisidine gives organic pigments.
Design/methodology/approach
The continuous increase in particle size of pigments confirms addition of diazotised salt to lignin by coupling reaction. Further, the dispersing ability of these coloured pigments were exploited in polymer matrix. Epoxy-polyamine cross linking system was doped with difference percentage of pigments and coated on mild steel metal surface. The morphology of these composites was understood by SEM, particle size, differential scanning calorimeter and thermo gravimetric analysis.
Findings
The synthesised organic pigments were characterised by FT-IR, 1H NMR and UV-visible spectroscopy. It was observed that hiding power of aniline- and m-nitroaniline–based azo pigments was more than p-nitroaniline- and p-anisidine–based azo pigments. Thermal properties as well as water contact angles of coatings were improved with pigment concentration. The chemical resistivity of coating was observed to be improved with the increasing % of lignin-based azo pigment.
Originality/value
Lignin-based azo pigment has great potential to replace metal oxide pigment and provide strategy for utilisation of lingo-cellulosic biowaste material.
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Siddhesh Umesh Mestry, Vardhan B. Satalkar and S.T. Mhaske
This study aims to describe the design and synthesis of two novel azo and imine chromophores-based dyes derived from two different aldehydes with intramolecular colour matching…
Abstract
Purpose
This study aims to describe the design and synthesis of two novel azo and imine chromophores-based dyes derived from two different aldehydes with intramolecular colour matching that are pH sensitive.
Design/methodology/approach
The visible absorption wavelength (λmax) was extended when azo chromophore was included in imine-based systems. The dyed patterns created sophisticated colour-changing paper packaging sensors with pH-sensitive chromophores using alum as a mediator or mordant. Due to the tight adhesive bonding, the dyes on paper’s cellulose fibres could not be removed by ordinary water even at extremely high or low pH, which was confirmed by scanning electron microscopy analysis. The dyed patterns demonstrated an evident, sensitive and fast colour-changing mechanism with varying pH, from pale yellow to red for Dye-I and from pale yellow to brown-violet for Dye-II.
Findings
The λmax for colour changing was recorded from 400 to 490 nm for Dye-I, whereas from 400 to 520 for Dye-II. The freshness judgement of food was checked using actual experiments with cooked crab spoilage, where the cooked crab was incubated at 37 oC for 6 h to see the noticeable colour change from yellow to brown-violet with Dye-II. The colour-changing mechanism was studied with Fourier transform infrared (FTIR) spectra at different pH, and thin layer chromatography, nuclear magnetic resonance and FTIR spectroscopy studied the desired structure formation of the dyes. Potential uses for smart packaging sensors include quickly detecting food freshness during transportation or right before consumption.
Originality/value
1. Two novel azo-imine dyes have been synthesized with a pH-responsive effect. 2. The pH-responsive mechanism was studied. 3. The study was supported by computational chemistry using density functional theory. 4. The obtained dyes were used to make pH-responsive sensors for seafood packaging to judge the freshness.
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Fatemeh Ashouri Mirsadeghi, Enayatollah Moradi Rufchahi and Saeid Zarrabi
The purpose of this study, 3-aminopyridine, 8-aminoquinoline and some new synthesized 2-aminobenzothiazoles were diazotized with nitrosyl sulfuric acid and subsequently coupled…
Abstract
Purpose
The purpose of this study, 3-aminopyridine, 8-aminoquinoline and some new synthesized 2-aminobenzothiazoles were diazotized with nitrosyl sulfuric acid and subsequently coupled with 5-chloro-8-hydroxy quinoline to synthesize the corresponding heteroarylazo dyes 6–13.
Design/methodology/approach
The structures of dyes were characterized by mass, Fourier transform infra red, 1H proton nuclear magnetic resonance and ultra violet-visible spectroscopic techniques. Absorption spectra of the dyes were measured in acetic acid, ethanol, chloroform, acetonitrile, dimethyl formamide and dimethyl sulfoxide and correlated with the nature of the solvents and substituents. The effects of varying pH on the absorption wavelengths of the azo dyes were also studied. In addition, the acidity constants (pKa) of the dyes were determined using the spectrophotometric method in an ethanol-water mixture (80:20, v/v) at 20–23°C. Besides, density functional theory (DFT) calculations were carried out to compare the energies of proposed azo and hydrazone tautomers of the dyes.
Findings
The results showed that the withdrawing chloro groups on the diazo moiety have significant influence (red shift) on the electron absorption spectra of these dyes. In addition, introducing electron withdrawing chloro groups into the benzothiazoles moiety increased the acidic character of dyes.
Originality/value
The synthesized 7-hetroarylazo-5-chloro-8-hydroxy quinoline dyes are new members in the 8-hydroxyquinoline azo dyes family, where very few details regarding the synthesis of such dyes are reported before in the literature. They are unique in terms of synthesis, spectral properties and DFT calculations.
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H.Z. Shams, M.H. Helal, I.M. Samir and R.M. Mohareb
The purpose of this paper is to evaluate the dyeing performance of newly designed and synthesised azo dye systems based on polyfunctionally substituted oxopyridine core for…
Abstract
Purpose
The purpose of this paper is to evaluate the dyeing performance of newly designed and synthesised azo dye systems based on polyfunctionally substituted oxopyridine core for improved dyeing when applied to synthetic fibres.
Design/methodology/approach
For improved dyeing qualities, various azo dye systems were synthesised based on polyfunctionally substituted oxopyridine core as the coupling component. The heterocyclic moiety was coupled with diazotized aromatic amines or diazotized tetrahydrobenzothiophenes to afford the respective azo or hydrazono systems. Other counterparts were obtained via treatment with different reagents. The structure of the novel systems was elucidated based on elemental analysis and spectral data. Dyeing performance, electronic spectra and optical properties were characterised based on UV and K/S measurements. Fastness properties were also evaluated.
Findings
The novel systems were designed so that the functionalities located on the heterocyclic core afforded structure modification that led not only to good dispersion but also to improved adherence on the fibre. The sites of location led to construction of a resonating system with higher electron mobility and higher absorption maxima.
Research limitations/implications
The azo dyes, used in the present context were synthesised via a step‐wise pathway leading to different systems of dyes. In addition, the variations in substituents and sites of location on the heterocyclic core could also be studied.
Practical implications
The novel azo dye systems based on polyfunctionally substituted oxopyridine core provide a simple practical access to a series of azo dyes with improved dyeing properties. The availability of starting materials, the simplicity and efficiency for production in good yields and high‐purity can lead to valuable achievements for commercial production.
Originality/value
The designed and synthesised azo dye systems could find numerous applications as disperse dyes in the fields of dyeing, printing and surface coating. Moreover, the systems could find applications as reactive dyes for wool, silk and cellulosic fibres.
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Asieh Yahyazadeh, Enayatollah Moradi Rufchahi, Hessamoddin Yousefi and Seyyedeh Maryam Golzar Poursadeghi
This paper aims to synthesize 6-ethyl-4-hydroxyquinolin-2(1H)-one as a new enol-type coupling component in the preparation of some 3-arylazo-4-hydroxyquinolin-2(1H)-one dyes and…
Abstract
Purpose
This paper aims to synthesize 6-ethyl-4-hydroxyquinolin-2(1H)-one as a new enol-type coupling component in the preparation of some 3-arylazo-4-hydroxyquinolin-2(1H)-one dyes and evaluate the solvent effects on their absorption in ultraviolet-visible spectra.
Design/methodology/approach
6-Ethyl-4-hydroxyquinolin-2(1H)-one was synthesized by thermal cyclocondensation reaction of N, N′-bis(4-ethylphenyl) malonamide at 130–140°C in polyphosphoric acid. This compound was then applied in the azo-coupling reaction with some aniline-based diazonium salts, so as to prepare seven new mono-heterocyclic azo dyes. The structures of the compounds were confirmed using mass spectroscopic technique. Fourier transform infra red (FT-IR) and 1H proton nuclear magnetic resonance (1H NMR) and carbon-13 nuclear magnetic resonance (13 C NMR) studies on the structure of the azo compounds revealed that they exist as two E- and Z-isomers of hydrazone tautomer both in solid and solution state. The effects of acid and base on the visible absorption spectra of the dyes were also evaluated and discussed.
Findings
Ultra violet-visible UV-vis absorption spectra of the dyes didn’t show significant variation by changing of solvents because of intramolecular H-bonding between proposed hydrazone forms and 2- and 4-keto functions in their structures. The spectra of the dyes were not sensitive to the addition of acid but were very sensitive to base.
Originality/value
The synthesized 3-arylazo-4-hydroxyquinolin-2(1H)-one dyes are new members in the 4-hydroxyquinolin-2(1H)-one azo dyes family, where very few details regarding the synthesis of such dyes are reported before in the literature. They are unique in terms of synthesis and spectral properties.
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Galal H. Elgemeie, Maher H. Helal and Heba M. El‐Sayed
The synthesis and chemistry of nitrogen heterocyclic azo compounds have been extensively studied. Many derivatives of this type were proved to be excellent dyes. Presents a…
Abstract
The synthesis and chemistry of nitrogen heterocyclic azo compounds have been extensively studied. Many derivatives of this type were proved to be excellent dyes. Presents a systematic and comprehensive survey of all recently synthesised nitrogen heterocyclic azo dyes according to dyeing methods.
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M.H. Helal, G.H. Elgemeie and D.M. Masoud
This paper's aim is to evaluate the dyeing performance of newly designed azo dye system based on thiazole substituted for improved dyeing when applied to synthetic fibres.
Abstract
Purpose
This paper's aim is to evaluate the dyeing performance of newly designed azo dye system based on thiazole substituted for improved dyeing when applied to synthetic fibres.
Design/methodology/approach
For improved dyeing qualities, various azo dye systems were synthesised based on polyfunctionally substituted thiazole as the coupling component. The heterocyclic moiety was coupled with diazotised aromatic amines to afford the respective azo or hydrazono systems. The structure of the novel systems was elucidated based on elemental analysis and spectral data. Dyeing performance, electronic spectra and optical properties were characterised based on UV and K/S measurements. Fastness properties were evaluated.
Findings
The novel systems were designed so that the functionalities located on the heterocyclic ring afforded structure modification that led not only to good dispersion but also to improved adherence on the fibre. The location of the sites led to constructing a resonating system with higher electron mobility and higher absorption maxima.
Research limitations/implications
The azo dyes, used in the present context were synthesised via a step‐wise pathway leading to new dyes. In addition, the variations in substituents and location of sites on the heterocyclic core could also be studied.
Practical implications
The novel azo dye systems based on polyfunctionally substituted thiazole provided a simple practical access to a series of azo dyes with improved dyeing properties. The availability of starting materials, the simplicity and efficiency to production in good yields and high purity lead to valuable achievements for commercial production.
Originality/value
The designed azo dye systems could find numerous applications as disperse dyes in the fields of dyeing, printing and surface coating. Moreover, the systems can find applications as reactive dyes for wool, silk and cellulosic fibres.
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Keywords
The purpose of this paper is to find an effective route to fabricate high transparent top electrode in quantum dots light-emitting diodes (QLEDs).
Abstract
Purpose
The purpose of this paper is to find an effective route to fabricate high transparent top electrode in quantum dots light-emitting diodes (QLEDs).
Design/methodology/approach
Al-doped ZnO (AZO) top cathode with high transparency have been deposited by an atomic layer deposition (ALD) method at 140°C for 1 h. The products are studied by UV-vis spectrometer and atomic force microscopy (AFM). The electroluminescence spectra of QLED are recorded using an Ocean Optics high-resolution spectrometer (HR4000). The devices were measured under ambient conditions without encapsulation.
Findings
The AZO-based QLED shows excellent performance with high luminance and current efficiency.
Originality/value
The AZO obtained by ALD method is a promising cathode candidate for application in QLEDs.
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Jiaxue Yu, Jinglin Tang, Xiaoyan Wang, Jinmei Du, Changhai Xu and Shansheng Zhang
This paper aims to synthesize benzothiazole-azo disperse dyes which can be applied not only for dyeing and alkaline reduction of polyester fabric in one bath, but also for dyeing…
Abstract
Purpose
This paper aims to synthesize benzothiazole-azo disperse dyes which can be applied not only for dyeing and alkaline reduction of polyester fabric in one bath, but also for dyeing and peroxide bleaching of cotton/polyester blend fabric in one bath.
Design/methodology/approach
The synthesized benzothiazole-azo disperse dyes were confirmed by proton nuclear magnetic resonance (1H-NMR) spectroscopy, mass spectroscopy (MS) and UV–visible spectrophotometry. The performance on resistance to alkaline treatment and peroxide bleaching was tested by measuring the color strength of polyester fabric dyed with the synthesized benzothiazole-azo disperse dyes under high-temperature and high-pressure conditions.
Findings
Increasing the electron-withdrawing ability of the substituents in the diazo component and the electron-donating ability of the substituents in the coupling component resulted in a significant bathochromic shift of the maximum absorption wavelength. Except that the disperse dyes synthesized from the coupling components containing the hydroxyethyl group were unstable in alkaline solution, all others exhibited high resistance to alkaline treatment and peroxide bleaching.
Practical implications
The synthesized benzothiazole-azo disperse dyes provide the opportunities to combine dyeing and alkaline reduction of polyester fabric into one bath, and combine dyeing and peroxide bleaching of cotton/polyester blend fabric into one bath.
Originality/value
The synthesized benzothiazole-azo disperse dyes help to establish short processes of polyester and polyester/cotton blend fabrics so as to reduce energy consumption and raise production efficiency.
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Esmail Rezaei-Seresht, Aboulfazl Salimi and Behnam Mahdavi
The purpose of this paper is synthesis and evaluation of antioxidant and antibacterial activities of a series of new azo dyes derived from 4-aminostilbene.
Abstract
Purpose
The purpose of this paper is synthesis and evaluation of antioxidant and antibacterial activities of a series of new azo dyes derived from 4-aminostilbene.
Design/methodology/approach
First, the starting material 4-aminostilbene was prepared via two successive Wittig and reduction reactions from 4-nitrobenzyl bromide. The obtained 4-aminostilbene was then reacted with some phenols under the normal azo coupling reaction conditions to give five new azo products. Antioxidant activity of the azo compounds was determined by radical scavenging assay using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Also, the antimicrobial activity of the compounds against one gram-positive and eight gram-negative strains was evaluated based on the inhibition zone using disc diffusion assay.
Findings
The structures of the azo dyes were identified and characterized by fourier-transform Infrared, 1H nuclear magnetic resonance (NMR) and ultraviolet-visible (UV-V) is spectroscopic methods. All the compounds showed higher antioxidant activity than ascorbic acid (Asc) and butylated hydroxytoluene (BHT) as positive controls. Moreover, the compounds showed lower antibacterial activity than the standard antibiotic vancomycin.
Research limitations/implications
Excellent antioxidant activity, along with antibacterial activity against Streptococcus pneumoniae and Pseudomonas aeruginosa, was observed for the two synthesized azo dyes.
Originality/value
Five novel azo dyes based on 4-aminostilbene were synthesized. The dyes have a highly p-extended conjugated structure comprising the phenolic and stilbenic segments, and they indicated good antioxidant activity, so that the two dyes (2c and 2d) even showed much more scavenging activity compared to BHT which is used as an antioxidant agent in food industries. These compounds with highest antioxidant activity also inhibited the growth of S. pneumoniae and P. aeruginosa.
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