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Article
Publication date: 30 May 2019

Hanna Abomelha

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.

Details

Pigment & Resin Technology, vol. 48 no. 4
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 4 September 2017

Mozhgan Hosseinnezhad and Kamaladin Gharanjig

The purpose of this paper is to study assembling parameters in dye-sensitised solar cells (DSSCs) performance. For this end, 3a,7a-dihydroxy-5ß-cholanic acid (cheno) are selected…

Abstract

Purpose

The purpose of this paper is to study assembling parameters in dye-sensitised solar cells (DSSCs) performance. For this end, 3a,7a-dihydroxy-5ß-cholanic acid (cheno) are selected as anti-aggregation agent and two solutions, namely, tetrabutyl ammonium iodide and (PMII)IL used as electrolyte.

Design/methodology/approach

A series of organic dyes were selected using N-substituents carbazole as electron donor group and acrylic acid and cyanoacrylic acid as electron acceptor groups. Absorption properties of purified dyes were studied in solution and on photoelectrode substrate. DSSCs were prepared in the presence of anti-aggregation agent and different electrolyte to determine the photovoltaic performance of each dyes.

Findings

The results showed that all organic dyes form J-aggregation on the photoanode substrate in the absence of anti-aggregation agent and the amounts of aggregation were reduced in the presence of anti-aggregation agent. DSSCs were fabricated in the presence of anti-aggregation agent. The photovoltaic properties were improved using tetrabutyl ammonium iodide as electrolyte. The maximum power conversion efficiency was achieved for D12 in the presence of cheno and tetrabutyl ammonium iodide as anti-aggregation agent and electrolyte, respectively.

Social implications

Organic dye attracts more and more attention due to low cost, facile route synthesis and less hazardous.

Originality/value

The effect of anti-aggregation agent and electrolyte on DSSCs performance was investigated for the first time.

Details

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

Keywords

Article
Publication date: 2 January 2018

Leighton Jones, Xujun Luo, Algy Kazlauciunas and Long Lin

This paper aims to synthesise and evaluate the properties of a novel smart material consisting of a metal-free organic black pigment with a unique chromophore for bifunctional…

Abstract

Purpose

This paper aims to synthesise and evaluate the properties of a novel smart material consisting of a metal-free organic black pigment with a unique chromophore for bifunctional applications in optoelectronics.

Design/methodology/approach

A robust and highly efficient organic reaction, namely, a double [2 + 2] cycloaddition, was deployed to transform a rod-like structure for charge-transfer applications to a strongly conjugated light-absorbing molecule for both optical and electronic applications.

Findings

The synthesis and characterisation of an air-stable metal-free black pigment is reported, which contains an unconventional donor–acceptor panchromatic chromophore with an absorption window spanning 600 nm; the compound was synthetically converted from an organic semiconducting molecular rod and retains strong charge-transfer properties. The chromophore comprises tetracyanoquinodimethane adduct on either side of a dithienothiophenyl core, capped with hexyl thiophenes that ensure solubility in common organic solvents. Its propensity to form excellent thin films on different substrates such as glass and paper, with a total opacity in organic solvent, gives it the potential for wide-ranging applications in organic optoelectronics.

Research limitations/implications

The synthetic chemistry and fundamental properties are investigated in the present study, with more detailed treatments and analysis to be soon developed. One leading smart material is presented, with further derivatives under investigation.

Practical implications

The work presented shows the possibility of converting structures from one application to another with relative ease, but how they retain properties for both, using well-known and facile conditions.

Originality/value

The structures are novel and an enhanced air-stable organic panchromatic chromophore is reported for processing in common organic solvents.

Details

Pigment & Resin Technology, vol. 47 no. 1
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: 4 July 2016

Mozhgan Hosseinnezhad

Dye-sensitised solar cells (DSSCs) have attracted a great deal of interest. Dye molecules are key materials in DSSCs that produce electrons. This study reports on synthesis of the…

Abstract

Purpose

Dye-sensitised solar cells (DSSCs) have attracted a great deal of interest. Dye molecules are key materials in DSSCs that produce electrons. This study reports on synthesis of the organic dyes and investigation their performance in DSSCs.

Design/methodology/approach

A series of new organic dyes were prepared using double rhodanine as the fundamental electron-acceptor group and aldehydes with varying substituents as the electron-donor groups. These dyes were first purified and then characterised by analytical techniques. DSSCs were fabricated to determine the photovoltaic behaviour and conversion efficiency of each individual dye.

Findings

Results demonstrated that all the dyes form j-type aggregates on the nano TiO2. All dyes in DSSC structure show suitable power conversion efficiency, and Dye 5 due to presence of OCH3 and OiPr presents maximum conversion efficiency.

Practical implications

In the search for high-efficiency organic dyes for DSSCs, development of new materials offering optimised photochemical stabilities as well as suitable optical and electrical properties is importance.

Social implications

Organic dyes as photosensitisers are interesting due to low cost, relatively facile dye synthesis and capability of easy molecular tailoring.

Originality/value

A series of new organic metal-free dyes were prepared as sensitisers for DSSCs for the first time.

Article
Publication date: 28 June 2013

Fatma Ali Mohamed and Rafaat Melad Mohareb

The purpose of this paper is to synthesise, characterise and find out properties of some new bifunctional dyes bis (monochlorotriazine) using tetrahydrobenzo[b]thiophene systems…

Abstract

Purpose

The purpose of this paper is to synthesise, characterise and find out properties of some new bifunctional dyes bis (monochlorotriazine) using tetrahydrobenzo[b]thiophene systems as the chromophoric moiety, bearing good colour strength, lightfastness, and other favourable properties.

Design/methodology/approach

The novel reactive dyes were prepared, containing bis monochlorotriazine as reactive groups. The dye is synthesised by diazotization and coupling reactions. Firstly the authors synthesised the ethyl 2‐amino 4,5,6,7‐tetrahydrobenzo[b]thiophen‐3‐carboxylate chromophoric moiety compound which in turn underwent diazotization and coupling then diazotized and coupled reaction with either 1‐amino‐8‐naphthol‐3,6‐disulphonic acid (H‐acid) and or 2‐amino‐8‐naphthol‐6‐sulphonic (γ acid) to give the monoazo dye intermediates compounds. The latter products reacted with 2,4,6‐trichloro‐1,3,5‐triazine in 1:1 molar ratio afforded, via nucleophilic displacement when subjected to condensation 2,4,6‐trichloro‐1,3,5‐triazine in 1:1 molar ratio afforded via nucleophilic displacement, which reacted with 1,4‐phenylenediamine in 2:1 molar ratio to give reaction with the 1,4‐phenylenediamine in 2:1 molar ratio, the bisazobifunctional bismonochlorotriazine reactive dyes.bisazo bifunctional bismonochlorotriazine reactive dyes thus yielding the new target reactive. The synthesised dyes were applied onto cotton fabric under the typical exhaust dyeing conditions and their dyeing properties were investigated.

Findings

The results assessed for dyeing indicate high quality dyeing properties However, the homobifunctional (bis MCT) dyes showed higher exhaustion and fixation values, colour yield and fastness properties.

Practical implications

The described method showed the synthesis of bis monochlorotriazines derived from the tetrahydrobenzo[b]thiophene derivative 3 followed by their application towards cotton fabric.

Social implications

Social implications are to prepare new reactive dyes having higher fastness and uses for dyeing cotton which is the commonest fabric use.

Originality/value

In this work, the novel reactive dyes derived from the tetrahydrobenzo[b]thiophene derivative 3 were synthesized and their structures were based on the analytical and spectral data. Such a group of compounds are considered to be excellent reactive dyes with different colour shades.

Details

Pigment & Resin Technology, vol. 42 no. 4
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 7 September 2015

Kamaladin Gharanjig and Mozhgan Hosseinnezhad

The purpose of this paper is to prepare new organic dyes and use them as sensitisers in dye-sensitised solar cells. These dyes were synthesised and purified and then characterised…

Abstract

Purpose

The purpose of this paper is to prepare new organic dyes and use them as sensitisers in dye-sensitised solar cells. These dyes were synthesised and purified and then characterised by analytical techniques. Spectrophotometric evaluations of the prepared dyes were carried out in solution and on a nano-anatase TiO2 substrate to assess the possible changes in the status of the dyes in different environments. Finally, the photovoltaic properties were investigated in dye-sensitised solar cells.

Design/methodology/approach

So as to synthesise dyes, N-substituents carbazole were utilised as the fundamental electron donor group and cyanoacrylic acid or acrylic acid as electron acceptor anchoring groups. Purified dyes were dissolved in solution and coated on TiO2 substrate. Finally, dye-sensitised solar cells were fabricated to determine the photovoltaic behaviour and conversion efficiency of each individual dye.

Findings

The results showed that the dyes form j-type aggregates on the nano TiO2. The oxidation potential of synthesised carbazole dyes is > 0.2 V vs Fc/Fc+; hence, their high performance in dye-sensitised solar cells. Dye 3 exhibited 2.11 per cent of conversion efficiency in comparison to 2.89 per cent for the identical cells with Dye 9 containing cyanoacrylic acid which acted as the best acceptor group.

Practical implications

The novel dyes look as promising as highly light fast, efficient dyes for dye-sensitised solar cells.

Social implications

Organic dye provides low cost and less hazardous materials for dye-sensitised solar cells.

Originality/value

A series of new organic dyes were synthesised as sensitisers for dye-sensitised solar cells for the first time.

Article
Publication date: 25 October 2018

Amira E.M. Abdallah and Rafat M. Mohareb

This work aims to synthesize a series of novel acyclic and/or heterocyclic systems, as precursors for dyes with potential antimicrobial activity that could be used for…

Abstract

Purpose

This work aims to synthesize a series of novel acyclic and/or heterocyclic systems, as precursors for dyes with potential antimicrobial activity that could be used for simultaneous dyeing and antimicrobial textile finishing. Thus, a series of novel pyridine, thiophene and pyrazolo[3,4-b]pyridine derivatives were synthesized, and their antimicrobial and textile finishing properties were studied and evaluated.

Design/methodology/approach

The synthesis, structure elucidation and antimicrobial activities of the newly synthesized compounds based on 4,4-dicyano-3-phenyl-but-3-enoic acid phenylamide (1) were demonstrated. The minimal inhibitory concentration in μg/mL of the compounds showed significant antimicrobial activity against most of the tested organisms. On the other hand, their spectral characteristics and fastness properties were measured and evaluated. Antimicrobial activities of the dyed fabrics in terms of inhibition zones (mm) were measured and evaluated.

Findings

A series of novel heterocyclic compounds (Schemes 1-3) were synthesized based on starting material (1). Compounds (1), 2, 4a, 8a and 9c exhibited comparable or even higher antibacterial activities than the selected standards (ampicillin), while compounds 2, 3c, 3d, 4a and 8b revealed higher antifungal activities than the selected standard (cycloheximide). On the other hand, some dyes showed high antimicrobial evaluation on the dyed fabrics (nylon 66, acetate and polyester) expressed as size (mm) of inhibition zones (Tables I-IV).

Practical implications

Results revealed that many hydrazo and azo derivatives were synthesized from some pyridines and thiophenes. The antimicrobial evaluation and textile finishing of the newly synthesized products revealed significant and potent values of antimicrobial activity.

Originality/value

All the synthesized compounds were novel and most of them exhibited higher antimicrobial activities than the selected standards antibiotics, thus are valuable for simultaneous dyeing and antimicrobial functional finishing of textile fabrics.

Details

Pigment & Resin Technology, vol. 48 no. 2
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 4 July 2016

G.H. Elgemeie, K.A. Ahmed, E.A. Ahmed, M.H. Helal and D.M. Masoud

The purpose of this study is to successfully implement microwave irradiation for the rapid synthesis of novel fluorescent dyes. The prepared dyes are then applied for printing of…

Abstract

Purpose

The purpose of this study is to successfully implement microwave irradiation for the rapid synthesis of novel fluorescent dyes. The prepared dyes are then applied for printing of polyester and polyamide by silk screen printing process.

Design/methodology/approach

A series of new N′-(methylene)-2-imino-2H-chromene-3-carbohydrazide derivatives 3a–r were synthesised in excellent yield and high atom economy by the Knoevenagel condensation of salicylaldehyde derivatives 1 and cyano-N′-methyleneaceto-hydrazide derivatives 2 in the presence of piperidine catalyst. The optical properties of the synthesised compounds were recorded; all of the compounds were found to be fluorescent in 1, 4-dioxane solution; they all emitted blue light (440-460 nm). This work shows that the optical properties strongly depend on the nature of the substituent, and indicate which type of substituent is favourable for a given application. It confirms that iminocoumarin derivatives could lead to a new generation of fluorescent probes, prone to easy modification of their chemical structure. These synthesised dyes are used to print polyester and polyamide fabrics using synthetic thickener in the printing paste for silk screen technique.

Findings

The structures of synthesised dyes were established and confirmed for the reaction products on the basis of their elemental analysis and spectral data (MS, IR and 1H-NMR). The suitability of the prepared dyestuffs for traditional printing on polyester and polyamide fabrics has been investigated. The prints obtained using the synthesised dyes were found to possess high colour strength and excellent overall fastness properties but relatively low light fastness.

Research limitations/implications

The synthesised fluorescent dyes were prepared by a simple reaction process in microwave. The optical properties for obtained dyes show include the fact that it will have various important applications. In addition, they were used for printing synthetic fabrics and were found to have good results.

Practical implications

The new fluorescent dyes’ system has excellent printing properties. Also they are superior in terms of yield, purity, colour strength and fastness properties which may lend them valuable commercial production.

Originality/value

The result of this work aimed to define the scope and limitation of the procedures for the synthesis of novel iminocoumarin dyes via a simple and economic way.

Details

Pigment & Resin Technology, vol. 45 no. 4
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 1 December 2004

A.M. Asiri

A range of methine dyes has been synthesised by condensation of electronegative active methylene compound, 4‐nitrophenylacetonitrile with substituted benzaldehydes. The electronic…

Abstract

A range of methine dyes has been synthesised by condensation of electronegative active methylene compound, 4‐nitrophenylacetonitrile with substituted benzaldehydes. The electronic absorption spectroscopic properties of the dyes were investigated. It was found that in general, substituents on the aromatic aldehyde moiety had a significant effect on the visible absorption maxima of the dyes.

Details

Pigment & Resin Technology, vol. 33 no. 6
Type: Research Article
ISSN: 0369-9420

Keywords

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