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Article
Publication date: 2 June 2021

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.

Details

Pigment & Resin Technology, vol. 51 no. 2
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 13 November 2007

M.A. El‐Kashouti, G.H. Elgemeie, M.M El‐Molla, H.S. El‐Sayad and K.A.E. Ahmed

To synthesize some new heterocyclic disperse azo dyes and their utilization in textile printing.

Abstract

Purpose

To synthesize some new heterocyclic disperse azo dyes and their utilization in textile printing.

Design/methodology/approach

To prepare 1‐cayno‐1‐substituted aryl azo‐2‐methyl benzothiazole by the reaction of 2‐aminothiophenol with malononitrile and the end product coupled with different diazonium salts. The prepared dyestuffs are established using element analysis, IR measurements, 1H‐NMR and Mass spectra. Printing pastes containing the prepared dyestuffs and a thickener were used for printing polyester and/or nylon 6 using either transfer printing or traditional printing.

Findings

New selected arylazo cyanomethyl benzothiazole dyes were obtained from the reaction of diazotized aniline derivatives with 2‐cyanomethyl benzothiazole as a coupling component. The suitability of the prepared dyestuffs for either heat transfer printing or traditional printing on polyester and nylon 6 fabrics has been investigated. The prints obtained from dyes containing non polar groups which have sublimation properties possess high colour strength as well as good overall fastness properties if compared to those obtained using dyes containing polar groups.

Research limitations/implications

The new heterocyclic disperse azo dyes were prepared from 2‐cyanomethylbenzothiazole and were utilized in preparing pastes for textile printing to print polyester and nylon 6 fabrics. In addition, the variation in substituents on the synthesized dyes could also be studied.

Practical implications

The method of synthesis of the new dyestuffs provides a simple and practical solution to prepare some new heterocyclic disperse azo dyes with low molecular weight, suitable for sublimation in heat transfer printing methods.

Originality/value

The methods for synthesis of the new heterocyclic disperse azo dyes are simple. These dyestuffs could be used in textile printing of polyester and nylon 6 on an industrial scale.

Details

Pigment & Resin Technology, vol. 36 no. 6
Type: Research Article
ISSN: 0369-9420

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: 12 September 2008

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.

Details

Pigment & Resin Technology, vol. 37 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 20 October 2021

Ali A. Ali, Maha Mohammed Elsawy, Salem S. Salem, Ahmed A. El-Henawy and Hamada Abd El-Wahab

Paper aims to preparation of new acid disperse dyes based on thiadiazol derivatives and evaluation of their use as antimicrobial colorants in digital transfer-printing ink…

Abstract

Purpose

Paper aims to preparation of new acid disperse dyes based on thiadiazol derivatives and evaluation of their use as antimicrobial colorants in digital transfer-printing ink formulations for printing onto polyester fabric substrates.

Design/methodology/approach

New disperse dyes based on 1,3,4 - thiadiazol derivative (dyes 1–3) were prepared and evaluated by different analysis then formulated as colored materials in the ink formulations. The viscosity, dynamic surface tension and particle size distribution of the prepared inks were measured. The printed polyester fabric substrates were tested using a variety of tests, including light fastness, washing, alkali perspiration and Crock fastness, as well as depth of penetration. Density-functional theory (DFT) calculations were carried out at the Becke3-Lee-Yang-parr (B3LYP) level using the 6–311** basis set, and the biological activity of the prepared disperse dyes was investigated.

Findings

The obtained results of the physical of the prepared ink revealed that thiadiazol disperse ink is a promising ink formulation for polyester printing and agrees with the quality of the printed polyester fabric. The optimization geometry for molecular structures agreed with the analysis of these compounds. The HOMO/LUMO and energy gap of the studied system were discussed. The molecular docking analysis showed strong interaction with DNA Gyrase and demonstrated to us the high ability of these inks to act as antimicrobial agents.

Practical implications

The prepared inks containing the prepared thiadiazol disperse dye were high-performance and suitable for this type of printing technique, according to the results. The prepared inks resist the growth of microorganisms and thus increase the ink's storage stability.

Originality/value

The prepared disperse dyes based on 1,3,4 - thiadiazol derivative (dyes 1–3) can be a promising colorant in different applications, like some types of paint formulations and as a colorant in printing of different fabric substrates.

Details

Pigment & Resin Technology, vol. 52 no. 1
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 18 September 2007

M.H. Helal, G.H. Elgemeie and D.M. Masoud

This paper aims to synthesize some new heterocyclic disperse azo dyes and their application in dyeing of polyester and polyamide fabrics.

Abstract

Purpose

This paper aims to synthesize some new heterocyclic disperse azo dyes and their application in dyeing of polyester and polyamide fabrics.

Design/methodology/approach

Pyrazolopyrimidine derivatives containing arylazo function by the reaction of 3,5‐ diaminopyrazole with ketene dithioacetals were prepared. The prepared dyestuffs are established using elemental analysis, IR measurements, 1H‐NMR and Mass spectra.

Findings

2,5‐diamino‐3‐arylazo‐N‐aryl‐6‐carboxamide‐7‐methylthio‐pyrazolo[1,5‐a]pyrimidine have been synthesized by the simple method. The dyed fabrics have a very good (4‐5) to excellent (5) results toward washing, perspiration, and rubbing fastness properties. The dyes are superior in terms of preparation and fastness properties.

Research limitations/implications

The disperse azo dyes used in this paper were synthesized via a step‐wise pathway leading to the new azo dyes. In addition, the variations in substituents and sites of location on the heterocyclic moiety could also be studied.

Practical implications

The new azo dye systems based on substituted pyrazolopyrimidine provided a series of azo dyes with improved dyeing properties. The dyes are superior in terms of yield, purity, colour strength, and fastness properties and will lead to valuable achievements for commercial production.

Originality/value

The synthesized disperse azo dyes are superior in terms of preparation, yield, purity, and fastness properties.

Details

Pigment & Resin Technology, vol. 36 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 7 November 2008

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.

Details

Pigment & Resin Technology, vol. 37 no. 6
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: 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

Article
Publication date: 1 April 1994

Y.M. ElKholy and S.A. Abd El‐Hafiz

In recent years heterocyclic azo dyes have been the subject of an intense research by dye manufacturers. Even so, little has been devoted to technical properties, so we have…

Abstract

In recent years heterocyclic azo dyes have been the subject of an intense research by dye manufacturers. Even so, little has been devoted to technical properties, so we have recently directed our research activities towards studying the ability of thiazole azo and hydrazono disperse dyes for dyeing of polyester and cellulose acetate.

Details

Pigment & Resin Technology, vol. 23 no. 4
Type: Research Article
ISSN: 0369-9420

1 – 10 of 143