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This study aims to focus on the possibility of developing new thiazole azo dyes with good colouristic application properties, biological and pharmacological activities.
Abstract
Purpose
This study aims to focus on the possibility of developing new thiazole azo dyes with good colouristic application properties, biological and pharmacological activities.
Design/methodology/approach
Coupling of curcumin with different aromatic diazonium salts of 2-amino thiazole derivatives, such as 2-aminobenzothiazole, 2-amino-5-phenylthiazole, 2-amino-5-methylthiazole and 2-amino-5-nitrothiazole-produced novel azo dyes. Structures of all synthesised dyes were fully confirmed via spectroscopic and analytical methods. Those compounds were examined for their antimicrobial, anticancer and antioxidant activities. They were applied on polyester fabrics and, subsequently, their dyeing properties, light, washing, perspiration, rubbing and sublimation fastness were determined.
Findings
Prepared dyestuffs were suitable for dyeing polyester fabrics. It was found that all prepared dyes possess high colour strength, as well as good overall fastness properties. Meanwhile, the synthesised compounds exhibited good biological and pharmacology activity.
Research limitations/implications
Synthesis of these four azo dyes for textile dyeing was not conveyed earlier.
Practical implications
Thaizolyl disperse dyes were responsible for giving better colour assessment and fastness properties on polyester fabrics.
Social implications
Although, most of synthesis eco-friendly dyes are expensive, they are showing a good antimicrobial and anticancer activity.
Originality/value
It gave straightforward approach to synthesise novel thiazolyl azo dyes with good biological, pharmacology activities, good colour assessment, and fastness properties.
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E. Abdel‐Latif, F.A. Amer, M.A. Metwally and M.E. Khalifa
The purpose of this paper is to synthesise some new 5‐arylazothiazole disperse dyes and study their application in dyeing polyester fibres.
Abstract
Purpose
The purpose of this paper is to synthesise some new 5‐arylazothiazole disperse dyes and study their application in dyeing polyester fibres.
Design/methodology/approach
A series of 5‐arylazo‐2‐(arylidenehydrazino)‐4‐substituted‐thiazole dyes were prepared by cyclocondensation of hydrazonoyl bromides with various thiosemicarbazone derivatives.
Findings
The dyed fibres exhibit very good washing, perspiration, sublimation and light fastness properties with little variation in the moderate to good rubbing fastness. The ease of preparation and the acceptable fastness properties makes these dyes particularly valuable.
Research limitations/implications
In the present paper, the synthesis of 5‐arylazo‐2‐(arylidenehydrazino)‐thiazole disperse dyes was achieved by one step pathway. In addition, the variations in substituents on the aryl and thiazole moieties could also be studied.
Practical implications
The new arylazo‐thiazole disperse dyes are superior in terms of yield, purity, colour strength, and having fastness properties of an order acceptable for commercial utilisation.
Originality/value
The synthesised disperse azo dyes are superior in terms of preparation, yield, purity, and fastness properties.
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Mozhgan Hosseinnezhad and Hanieh Shaki
The purpose of this paper is to study the substituent effect in dye-sensitized solar cells’ (DSSCs) performance. For this end, three new metal organic dyes with DPA structure were…
Abstract
Purpose
The purpose of this paper is to study the substituent effect in dye-sensitized solar cells’ (DSSCs) performance. For this end, three new metal organic dyes with DPA structure were synthesized. For investigation of the substituent effect, two different anchoring groups, namely, 1,3-dioxo-1Hbenz[de]isoquinolin-2(3H)-yl)benzenesulfonamides and 1,8-naphthalimide, were used.
Design/methodology/approach
Three organic dyes based on azo were selected, which contain various electron donor groups. Absorption properties of purified dyes were studied in solution and on photoelectrode (TiO2 and ZnO) substrate. DSSCs were prepared to determine the photovoltaic performance of each photosensitizer.
Findings
The results showed that all organic dyes form J-aggregation on the photoanode substrate. Cyclic voltammetry results for all organic dyes ensured an energetically permissible and thermodynamically favorable charge transfer throughout the continuous cycle of photo-electric conversion. The results illustrate conversion efficiencies of cells based on solution Dyes 1, 2 and 3 and TiO2 as 3.44, 4.71 and 4.82 per cent, respectively. The conversion efficiencies of cells based on solution Dye 1, 2 and 3 and ZnO are 3.21, 4.09 and 4.14 per cent, respectively.
Practical implications
In this study, the development of effect of assembling materials, offering improved photovoltaic properties.
Social implications
Organic dye attracts more and more attention because of its low-cost, facile route synthesis and less-hazardous properties.
Originality/value
To the best of the authors’ knowledge, the effect of anchoring agent and nanostructure on DSSCs performance was investigated for the first time.
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This paper aims to synthesise some novel diazobenzene dyestuffs clubbed with sulphonamide moiety and their application for polyester fabrics in addition to evaluating their…
Abstract
Purpose
This paper aims to synthesise some novel diazobenzene dyestuffs clubbed with sulphonamide moiety and their application for polyester fabrics in addition to evaluating their biological activities.
Design/methodology/approach
New diazobenzene disperse dyes with improved chemical construction via sulphonamides were designed. This amendment of diazobenzene dyes was completed by introducing sulphonamide derivatives through Japp–kilingman reaction. All new synthesised dyes were elucidated by elemental analyses and spectral data (IR and 1 H-NMR). Biological activities of the synthesised diazobenzene sulphonamide derivatives were evaluated.
Findings
The synthesised diazobenzene dyestuffs clubbed with sulphonamides were applied on polyester fabrics. The synthesised dyes showed that good fastness properties and their biological evaluation exhibited good efficacy towards antibacterial, antioxidant and anticancer.
Originality/value
Sulphonamide derivatives have numerous uses, such as being used in dyestuff and providing antimicrobial, antioxidant, and anticancer properties. Sulphonamide derivatives with diazobenzene coupler components exhibited an interesting colorant for polyester and provided better biological efficacy for other non-textile applications. This work afforded new disperse dyes beside their medical applications.
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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.
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Keywords
Min Li, Kaili Song, Kongliang Xie and Aiqin Hou
The purpose of this paper is to synthesise a disperse dye based on benzisothiazole and to characterise its crystal morphology, dispersing stability, to study the relationship…
Abstract
Purpose
The purpose of this paper is to synthesise a disperse dye based on benzisothiazole and to characterise its crystal morphology, dispersing stability, to study the relationship between the chemical structure and the dyeing property of the dye.
Design/methodology/approach
The disperse dye based on benzisothiazole, 3-(3-methyl-4-N-ethyl-N-benzyl-phenyldiazenyl)-5-nitro-2,1-benzisothiazoles, was synthesized. The disperse dye based on benzisothiazole, 3-(3-methyl-4-N-ethyl-N-benzyl-phenyldiazenyl)-5-nitro-2,1-benzisothiazoles, was synthesised. The chemical structure of the dye obtained was characterised by infrared spectrum Fourier transform infrared spectroscopy and nuclear magnetic resonance (1HNMR), and the crystal morphology was observed by Field Emission Scanning Electron Microscopy. Sodium salt of polycondensated naphthalenesulphonic acid (dispersing agent sodium salt of polycondensated naphthalenesulphonic acid [MF]) and a sulphonated amino polyether (anionic surfactant B600) were employed to grind and disperse the dye crystals. The dispersion property of the dye particles was characterised. Dyeing property of the dispersion system was also studied.
Findings
The dye formed spherical crystals that were made up of a large number of acicular crystals similar to spherical chrysanthemum. The crystals had warping crystal centres inside the spheres. The particle sizes of the dispersion with the mixture of B600 and MF had an uniform distribution and were smaller than that of the dispersion with only single dispersing agent MF. Dyeing with the dispersion system had an excellent reproducibility under alkalinic condition.
Practical implications
An alkalinic dyeing method for poly(ethylene terephthalate) (PET) with disperse dyes as a cleaner wet process had been developed. Such a process combined pretreatment and dyeing process using the alkali-stable disperse dyes and reduced the consumption of water and energy and improved production efficiency.
Originality/value
The crystal morphology, dispersion and dyeing properties of the synthesised disperse dye for dyeing PET fabric under alkalinic condition were discussed. This disperse dye has an important potential application in alkalinic dyeing method.
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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.
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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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This study aims to the synthesis of some novel 4-arylazo-3-hydroxythiophene analogues containing sulphapyridine and sulphathiazole dyestuffs and studying their application in…
Abstract
Purpose
This study aims to the synthesis of some novel 4-arylazo-3-hydroxythiophene analogues containing sulphapyridine and sulphathiazole dyestuffs and studying their application in dyeing polyester fabrics and rendering their antibacterial efficacy.
Design/methodology/approach
Simultaneous dyeing and antibacterial finishing for polyester fabric using a new antibacterial disperse dye having a modified chemical structure to thiophene dyes were studied. Construction of the thiophene dyes was carried out by diazo-coupling of diazotized sulphonamide-containing heterocyclic rings sulphapyridine and sulphathiazole with ethyl α-phenylthiocarbamoyl-acetoacetate followed by cyclizing the produced 2-arylazo-thioacetanilide with various α-halogenated reagents. All newly synthesized compounds were characterized by elemental analysis and extensive study of their spectral data (IR and 1H-NMR). The dyeing characteristics of these thiophene dyestuffs were evaluated at optimum conditions. Antibacterial activities of the obtained thiophene dyes were studied against some Gram-positive and Gram-negative bacteria.
Findings
The synthesized thiophene-containing sulphonamides dyes were applied on polyester fabric. The modified dyes exhibited a good fastness properties and antibacterial efficacy against some Gram-positive and Gram-negative bacteria. Synthesized dyes showed higher antibacterial potency than the reference standard drug.
Research limitations/implications
Synthesis of these disperse azo dyes for textile dyeing had never been reported previously.
Practical implications
The dyestuffs derived from thiophene are reasonable azo disperse dyestuffs giving good all-round fastness properties on polyester fabrics.
Originality/value
Thiophene dyes are used for dyeing polyester fabrics with brilliant colour and good fastness properties. The presence of sulphonamides moieties increase their fastness properties and elevate their antibacterial properties. Moreover, they can be used as antimicrobial finish due to their bactericidal properties on dyed textiles. This work afforded a new thiophene colorant that can be used in many different uses like polyester packing, thread Surgery, blends and other uses in medical textile.
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Hatem Gaffer, Hamada Mashaly, Shaymaa Hassan Abdel-Rhman and Mamdouh Hammouda
The study reported in this paper aims to synthesize some new curcumin containing sulphadiazine and sulphathiazole dyestuffs and study their application in dyeing silk fabrics…
Abstract
Purpose
The study reported in this paper aims to synthesize some new curcumin containing sulphadiazine and sulphathiazole dyestuffs and study their application in dyeing silk fabrics rendering the dyed fabric antibacterial.
Design/methodology/approach
Simultaneous dyeing and antibacterial finishing for silk fabric using a new antibacterial acid dye having a modified chemical structure to curcumin were conducted. This modification of curcumin dye was carried out by introducing sulphonamide containing heterocyclic rings sulphadiazine and sulfathiazole through coupling with curcumin. All newly synthesized dyes were characterized by elemental analyses and spectral data (IR, 1H-NMR and MS). The dyeing characteristics of these dyestuffs were evaluated at optimum conditions. Antibacterial activities of the dyed samples at different concentrations of both dyes were studied against gram-positive (Staphylococcus aureus) and gram-negative (Salmonella typhimurium) bacteria.
Findings
The synthesized curcumin-containing sulphonamide dyes were applied on silk fabrics. The modified dyes exhibited good fastness properties compared to curcumin dye at optimum conditions. It was found that synthesized dyes exhibit good fastness and antibacterial properties efficient against gram-positive and gram-negative bacteria. The dyed silk fabrics showed higher antibacterial efficacy after many times of washing.
Originality/value
Curcumin, a common natural dye used for fabric and food colouration, was used as an antimicrobial finish due to its bactericidal properties on dyed textiles. A common dyeing process could provide textiles with colour as well as antimicrobial properties. Novel antibacterial dyestuff containing curcumin moieties with sulphonamide coupler components were shown to be an interesting natural colorant for silk with high antimicrobial ability of the dyed silk fabrics. This work has afforded a new acid dye that can be used in medical textile.
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