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Article
Publication date: 3 May 2022

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.

Details

Pigment & Resin Technology, vol. 52 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 8 September 2022

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.

Details

Pigment & Resin Technology, vol. 53 no. 2
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 1 August 2001

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…

1179

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.

Details

Pigment & Resin Technology, vol. 30 no. 4
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 29 June 2012

M.S. Yen

The purpose of this paper is to investigate some novel bis‐hetaryl dyes containing both azo and azo methine chromophores on their molecular structures: two series of different…

Abstract

Purpose

The purpose of this paper is to investigate some novel bis‐hetaryl dyes containing both azo and azo methine chromophores on their molecular structures: two series of different molecular structures of these dyes were synthesised. The spectral characteristics and the relationships between colour and constitution of these dyes in solvents with different polarities were systematically investigated and discussed.

Design/methodology/approach

A series of novel bichromophoric dyes containing azo and azomethine chromophores were synthesized using two kinds of reaction routes. 2‐amino‐4‐(p‐substituted) phenyl‐thiazole derivatives, which are coupling components, were subjected to diazotisation with aniline derivatives and then to condensation with benzaldehyde derivatives. By exchanging the synthesis route, two series of bichromophoric dyes could be obtained.

Findings

The maximum absorption wavelengths of the obtained dyes would be attributed to the higher bathochromic shift in basic organic solvent with high polarity, such as dimethylformamide, as compared with the solvent with low polarity, such as chloroform.

Research limitations/implications

In the present study, a series of novel bichromophoric dyes were synthesized by means of two‐step pathway. In addition, the effects of substituent on the primary aromatic amine and on benzaldehyde moieties will also be discussed.

Practical implications

This novel synthesis method of the thiazole ring would lead to the formation of 2‐amino‐4‐(p‐substituted)phenyl‐thiazole with heteroaromatic coupling component position at C‐5, and consequently would produce the heteroaromatic diazo component at C‐2 for the preparation of the heteroaryl diazo dyes.

Originality/value

In this paper, the bichromophoric dyes obtained by different synthesis routes would indicate that the effect of solvent polarity should be responsible for the bathochromic shifts of the dyes.

Details

Pigment & Resin Technology, vol. 41 no. 4
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 8 February 2021

Siddhesh Umesh Mestry, Umesh Ratan Mahajan, Aswathy M. and Shashank T. Mhaske

The purpose of this paper is to use the bio-based resource as the starting material for the synthesis of azo dye. Cardanol is one of the most used bio-based resources for carrying…

Abstract

Purpose

The purpose of this paper is to use the bio-based resource as the starting material for the synthesis of azo dye. Cardanol is one of the most used bio-based resources for carrying out the synthesis of various compounds having numerous end applications. The study presents an attempt to develop an azo dye from Cardanol having end applications in pH-responsive dyes.

Design/methodology/approach

The cardanol was sulfonated to block the para position by which ortho positioned hydroxyl group after diazotization and coupling will provide necessary pH-sensitivity. The diazotization of two naphthalene derivatives, i.e. 1-naphthol-8-amino-3,6-disulfonic acid (H-acid) and 7-amino-4-hydroxy-2-naphthalene sulfonic acid (J-acid) was carried out using the standard practice, and the diazotized compounds were coupled with the sulfonated cardanol. The obtained dyes were characterized by Fourier transform infrared, nuclear magnetic resonance, carbon-hydrogen-nitrogen-sulfur analysis and hydroxyl value. The colour properties were checked using UV-vis spectrophotometry and density functional theory, while thermogravimetric analysis was used for the thermal degradation studies of both the dyes.

Findings

Water-soluble cardanol-based azo dyes were prepared successfully having good thermal stability, and the obtained results are being presented in this paper.

Originality/value

The originality lies between the use of cardanol as a bio-based resource for the synthesis of azo-dye and the obtained azo-dye has the pH-sensitivity.

Details

Pigment & Resin Technology, vol. 50 no. 3
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 20 October 2021

Nidhi Goyal, Deepali Rastogi, Manjeet Jassal and Ashwini K. Agrawal

Dyeing and printing are important steps in textile manufacturing. After the process completion, these dyes are released in the effluent. These dyes impart an unacceptable…

Abstract

Purpose

Dyeing and printing are important steps in textile manufacturing. After the process completion, these dyes are released in the effluent. These dyes impart an unacceptable appearance but are also toxic to the soil and water bodies. The present research has been carried out to study the rate of photocatalytic degradation of an azo dye, namely, CI Direct Green 26, using titania nanoparticles under ultra violet (UV) irradiation as a function of temperature and time. Azo dyes account for the majority of all dyestuffs are produced and extensively used in the textile, paper, food, leather, cosmetics and pharmaceutical industries. Titania nanoparticles have been found to successfully degrade these dyes in the presence of UV light. The purpose of the present paper was to study the photodegradation of azo dyes using titania nanoparticles at different temperatures and time periods.

Design/methodology/approach

Titania nanoparticle concentration of 0.1% (w/v) was dispersed in distilled water by sonication for 1 h in sonication bath. The of rate of degradation of Direct Green 26 dye in the titania nanoparticle dispersion, under UV-A exposure was studied at different temperatures ranging from 25°C to 65 °C for time periods ranging from 1 h to 6 h. Photocatalytic degradation tests were performed in a specially designed UV reactor chamber. Raman spectroscopy of Titania nanoparticles, dye and titania/dye mixture before and after UV exposure was carried out using Confocal Laser Dispersion Raman Microscope (Renishaw, UK) with 785 nm excitation laser.

Findings

Titanium dioxide is an efficient photocatalyst for decolourisation of direct dye. The photodegradation of the direct Green dye was found to follow the pseudo first-order reaction. The Arrhenius activation energy was found to be 24.8 kJ/mol with A value of 0.0013 for the photocatalytic degradation of the dye. Raman spectroscopy also confirmed the adsorption of dye on titania nanoparticle and its complete degradation on exposure to UV light.

Practical implications

This research highlights the application of titania nanoparticles for the effective degradation of dye in the effluent from textiles, clothing, paper and any kind of dyeing process. Azo dyes account for the majority of all dyestuffs are produced and extensively used in the textile, paper, food, leather, cosmetics and pharmaceutical industries. Titania nanoparticles have been found to successfully degrade these dyes in the presence of UV light which can be very beneficial for the effluent treatment plants in textile and other industries.

Originality/value

Azo dyes are one of the harmful pollutants released in textile waste water. The degradation and removal of the coloured waste in the textile effluent is an important environmental concern and needs to be investigated. The research is one of the first to investigate and understand the mechanism of the degradation of an azo dye in the presence of titania nanoparticles by Raman spectroscopy.

Details

Research Journal of Textile and Apparel, vol. 26 no. 4
Type: Research Article
ISSN: 1560-6074

Keywords

Article
Publication date: 30 September 2022

Hamada Abdelwahab, Fatimah A.M. Al-Zahrani, Ali A. Ali, Ammar Mahmoud and Long Lin

This paper aims to synthesize new screen-printing ink formula based on new derivatives of azo thiadiazol disperse dyes and evaluate their characteristics after being printed on…

Abstract

Purpose

This paper aims to synthesize new screen-printing ink formula based on new derivatives of azo thiadiazol disperse dyes and evaluate their characteristics after being printed on polyester fabric substrates.

Design/methodology/approach

New dispersed dyes based on 1, 3, 4-Thiadiazole derivatives (dyes 1 and 2) were prepared and confirmed by different analyses, infrared (IR), mass and nuclear magnetic resonance (NMR) spectroscopy, and then formulated as colored materials in the screen-printing ink formulations. Printing pastes containing the prepared dyestuffs and other ingredients were used for printing polyester using screen-printing or traditional printing. The characteristics of printed polyester fabric substrates were measured by color measurements such as a*, b*, L*, C*, E, Ho, R% and color strength, as well as light, washing, crock and alkali perspiration fastness, and finally, the depth of penetration was evaluated.

Findings

The prepared 1, 3, 4-Thiadiazole derivatives (dyes 1 and 2) were obtained from the reaction of 5,5’-(1,4-phenylene)bis(1,3,4-Thiadiazole-2-amine) with resorcinol and m-toluidine as a coupling component. The suitability of the prepared dyestuffs for silk screen-printing on polyester fabrics has been investigated. The prints obtained from a formulation containing dye 1 possess high color strength as well as good overall fastness properties if compared to those obtained using dye 2.

Practical implications

The method of synthesis of the new dyestuffs and screen-printing ink provides a simple and practical solution to prepare some new heterocyclic disperse azo dyes, and they are formulated in the screen-printing inks for printing on a polyester fabric substrate.

Originality/value

The prepared disperse dyes based on 1,3,4-Thiadiazole derivatives (dyes 1 and 2) could be used in textile printing of polyester on an industrial scale.

Details

Pigment & Resin Technology, vol. 53 no. 3
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 4 September 2017

A. Shams-Nateri, E. Dehnavi and E. Zahedi

This work aims to explain the effect of common salt on absorbance spectra and solubility of textile direct dyes, which is important in analysing and reusing wastewater of dyeing…

Abstract

Purpose

This work aims to explain the effect of common salt on absorbance spectra and solubility of textile direct dyes, which is important in analysing and reusing wastewater of dyeing process.

Design/methodology/approach

Several textile dyes such as Direct red 243, Direct yellow 86 and Direct blue 201 solutions with and without NaCl salt were used to study the effect of common salt on solubility of textile direct dyes. Several methods such as derivative spectrophotometry, principal component analysis and colorimetric techniques were used to analyse the absorbance spectra of dye solution.

Findings

The obtained results indicate that the effect of common salt on absorbance spectra and solubility of textile direct dye depends on the chemical structure of dyes. The NaCl salt significantly affects the solubility of Direct red 243 (red dye) and Direct yellow 86 (yellow dye) which have Azo compounds containing four SO3 functional groups. But the NaCl salt does not change the solubility of Direct blue 201 (Blue dye) which has Azo compound containing two SO3 functional groups. Also, the NaCl salt decreases the accuracy of dye concentration prediction.

Practical implications

During reusing wastewater of dyeing process, the amount of dyes has been evaluated via absorbance spectra of dye solution.

Originality/value

This work explains the effect of common salt on solubility of textile direct dyes and the accuracy of dyes concentration prediction.

Details

Pigment & Resin Technology, vol. 46 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 30 July 2021

Mohamed Ezzat Khalifa, Adil Abdullah Gobouri, Mohamed Hesham Hassan Mahmoud, Abdulraheem Safar Almalki and Fahad Mustafa Kabli

This paper aims to synthesize new benzimidazole dyes aiming to study the solvent effects on their absorption in Ultraviolet-visible spectra.

Abstract

Purpose

This paper aims to synthesize new benzimidazole dyes aiming to study the solvent effects on their absorption in Ultraviolet-visible spectra.

Design/methodology/approach

Ureido/thioureido hydrazonamide benzimidazoles (U/THB) are prepared by condensation of N-aryl-1H-benzo[d]imidazole-2-carbohydrazonoyl bromides with ureido and/ or thioureido reagents. The target products are fully characterized for structural elucidation by means of their spectral and elemental methods. Solvatochromic behavior of U/THB dyes has been studied in different polar protic solvents at room temperature.

Findings

The absorption spectra distinguish two main bands at (350 nm–442 nm) and (308 nm–382 nm) referring to n-π* and π- π* transitions of the azo groups. Dimethyl formamide induces an extremely bathochromic transition comparing to the other protic solvents. The observed bathochromic shifts indicate strong interaction with solvents in the excited state. Most dyes show one absorbance in all solvents used, so they may exist in a single tautomeric form (hydrazo form).

Research limitations/implications

In the present paper, the synthesis of U/THB dyes was achieved by a simple and convenient pathway. In addition, the variations in substituents attached to the chromophoric moiety could also be studied.

Practical implications

The new U/THB dyes are accountable for providing good knowledge about their solvation and spectral properties of an order acceptable for industrial utilization.

Social implications

Synthesis of these new benzimidazole derivatives and study of their solvation and spectral properties provides good knowledge, which is very useful in many industrial applications (e.g. dye-sensitized solar cell, etc.).

Originality/value

The synthesized mono azo U/THB dyes are novel members in the benzimidazole family, where no details regarding the synthesis of such dyes are reported before in the literature. They are superior in terms of preparation, multiple applications and spectral properties.

Details

Pigment & Resin Technology, vol. 51 no. 3
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 27 February 2023

Ali A. Ali, H. Abd El-Wahab, Moustafa S. Abusaif, Ahmed Ragab, Omar A. Abdel-Jaid, E.A. Eldeeb and Yousry A. Ammar

The paper aims to the preparation of novel disperse dye based on azo salicylaldehyde derivatives TF-A [2-hydroxy-5-((3-(trifluoromethyl)phenyl)diazenyl)benzaldehyde] and full…

Abstract

Purpose

The paper aims to the preparation of novel disperse dye based on azo salicylaldehyde derivatives TF-A [2-hydroxy-5-((3-(trifluoromethyl)phenyl)diazenyl)benzaldehyde] and full evaluation of their use as disperse dye TF-ASC [bis 2-hydroxy-5-((3-(trifluoromethyl)phenyl)diazenyl)benzaldehyde Schiff base with 4,4'-methylenedianiline] for dyeing polyester fabric at various conditions.

Design/methodology/approach

The dispersed dye was synthesized via Schiff base condensation in the presence of ceric ammonium nitrate cerium ammonium nitrate 10 mmole% as an eco-friendly catalyst at room temperature. The chemical structure of the prepared dye was characterized via elemental analysis, Fourier-transform infrared spectroscopy, 1H- and 13 C-NMR spectroscopic analysis tools. This study thoroughly examined the dyeing of disperse dye TF-ASC on polyester at various conditions. The characteristics of dyed polyester fabric were measured by colour measurements, as well as light, washing, crock fastness and finally, colour strength. The discrete fourier transform (DFT) theoretical studies, including EHOMO, ELUMO and optimized geometrical structure, were assumed and discussed in detail.

Findings

The results showed that the synthesized organic dye TF-ASC was highly functional and appropriate for this kind of dyeing method. The dyeing fabrics obtained from disperse dye TF-ASC, properties possess high colour strength as well as good overall fastness properties. These dyes had a high affinity for polyester fabric, with just a tiny change in dye affinity when the pH was changed, even under alkaline circumstances. The dye levelness and shade depth of the colour results were good, and there were a variety of hues from light brownish yellow to deep brownish yellow. The results obtained from DFT computational studies such as EHOMO, ELUMO, optimized structure, diploe moment µ and electrophilicity index deduced that prepared organic dye TF-ASC is more applicable as a dispersed dye.

Originality/value

This research is significant because it provides a new dye for dyeing polyethylene terephthalate fibres with exceptional brightness and levelness; the method of preparation is a useful pathway due to its being known as a green chemistry method.

Details

Pigment & Resin Technology, vol. 53 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

1 – 10 of 282