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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: 26 August 2014

Nilgun Kizilcan and Merve Istif

The purpose of this paper is to produce an electroactive monomer containing ketonic resins and then to investigate redox reaction between Fe+3 and bounded thiophene in comonomers…

Abstract

Purpose

The purpose of this paper is to produce an electroactive monomer containing ketonic resins and then to investigate redox reaction between Fe+3 and bounded thiophene in comonomers. First, thiophene functionalised ketonic resins (Th-CFPDMSR) were synthesised by esterification reaction of thiophene-2-carbonyl chloride (ThCCl) and hydroxyl groups of cyclohexanone formaldehyde resin (CFR). Th-CFPDMSR was then polymerised by ferric salt. Thiophene modified ketonic resins (Th-CFPDMSR) as comonomers were characterised by common techniques such as gel permeation chromatography, proton nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimeter and scanning electron microscope.

Design/methodology/approach

Th-CFPDMSR comonomers were synthesised by esterification reaction of ThCCl and hydroxyl groups of ketonic resins. Then, the in-situ chemical oxidation (ISCO) of ThC-CFR in the presence of iron (III) chloride salt (FeCl3) was accomplished in chloroform/acetonitrile mixture solutions at room temperature.

Findings

Important structural factor determined quantitatively for Th-CFPDMSR is the CFPDMS/TCCl ratio after reaction. The mole ratio effect of TCCl and ketonic resin on the solubility, molecular weight, melting temperature (Tm) and glass transition temperature (Tg) values of the comonomers (TCCl-CFPDMSR) was investigated.

Research limitations/implications

The ferric ion (Fe+3) has a standard oxidation potential. Furthermore, FeCl3 can react with thiophene to produce a cation radical. FeCl3 cannot react with hydroxyl groups of ketonic resins. When ferric is used for ISCO application at relatively low temperatures (e.g. < 20°C), the oxidation reactions are usually less aggressive.

Practical implications

This work provides technical information for the synthesis of conducting block copolymer and for the synthesis of chain-extended resins. The modified resins contain thiophene. The chemical oxidation system has been used to polymerise these thiophene groups, and resins with much higher molecular weight might be produced. The resins may also promote the adhesive strength of a coating and corrosion inhibition to metal surfaces of a coating.

Originality/value

Novel Th-CFPDMSR comonomers were synthesised. These comonomers have higher Tg and Tm values than CF-PDMSR alone. The chemical oxidation system has been used to polymerise these thiophene functionalised ketonic resins.

Details

Pigment & Resin Technology, vol. 43 no. 5
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 2 March 2015

Esin Ateş, Nilgün Kizilcan and Merve İstif

The purpose of this paper is to synthesise an electro-active monomer containing ketonic resins and then to investigate the redox reaction between Fe+3 and bound thiophene in…

Abstract

Purpose

The purpose of this paper is to synthesise an electro-active monomer containing ketonic resins and then to investigate the redox reaction between Fe+3 and bound thiophene in comonomer. First, thiophene-functionalised ketonic resins were synthesised by esterification reaction of thiophene-2-carbonyl chloride (ThCCl) and hydroxyl groups of cyclohexanone formaldehyde resin (CFR). Thiophene-containing cyclohexanone formaldehyde resin (Th-CFR) was then polymerised by ferric salt. The structures of the specimens were characterised by means of Fourier transform infrared and Proton – Nuclear Magnetic Resonanse (1H-NMR) spectroscopy. Thermal properties of the samples were determined with differential scanning calorimeter. Molecular weights of the specimens were determined by gel permeation chromatography. The obtained samples were also characterised morphologically by scanning electron microscope.

Design/methodology/approach

Synthesis of Th-CFR comonomers by a combination of condensation polymerization and chemical oxidation polymerisation processes is described. First, Th-CFR units were prepared by direct condensation reaction of thiophene-2-carbonyl chloride (ThCCl) and hydroxyl groups of CFR. Then, the chemical oxidation (CO) of Th-CFR in the presence of anhydrous iron (III) chloride salt (FeCl3) was performed in chloroform (CHCl3)/acetonitrile mixture solutions at room temperature.

Findings

The important structural factor determined quantitatively for Th-CFR is the CFR/ThCCl ratio after reaction. The effect of the mole ratio effect of ThCCl and ketonic resin on the solubility, molecular weight, Tm and Tg values of the comonomers (Th-CFRs) were investigated.

Research limitations/implications

The ferric ion (Fe+3) has a standard oxidation potential. Furthermore, FeCl3 can react with thiophene to produce a cation radical. FeCl3 cannot react with hydroxyl groups of ketonic resins. When ferric is used for in situ chemical oxidation application at relatively low temperatures (e.g. < 20°C), the oxidation reactions are usually less aggressive.

Practical implications

This work provides technical information for the synthesis of conducting block copolymer and for the synthesis of chain-extended resins. The modified resins contain electro-active monomer as thiophene. The chemical oxidation system has been used to polymerise these thiophene groups and resins with much higher molecular weight might be produced. These resins may also promote the adhesive strength of a coating and corrosion inhibition to metal surfaces of a coating.

Social implications

This will be used for the preparation of AB- and ABA-type block copolymers. These block copolymers may exhibit different properties due to incorporation of monomer into the block copolymer structure.

Originality/value

Novel Th-CFR comonomers were synthesised. These comonomers have higher glass transition temperature (Tg) and melting temperature (Tm) value than CFR alone. The chemical oxidation system has been used to polymerise these thiophene-functionalised ketonic resins.

Details

Pigment & Resin Technology, vol. 44 no. 2
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 2 November 2015

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

The study aims to synthesise new thiophene-based dyes by an efficient method using sodium a-cyanoketene dithiolates as starting components for synthesis of tetra-substituted…

Abstract

Purpose

The study aims to synthesise new thiophene-based dyes by an efficient method using sodium a-cyanoketene dithiolates as starting components for synthesis of tetra-substituted thiophenes, which act as a coupler for the synthesised dye. The synthesised dyes are applied for printing polyamide and polyester fabrics using the screen printing technique.

Design/methodology/approach

Treatment of 1 with carbon disulfide in alkaline medium forming disodium salt 2, which act as starting point for heterocyclisation to prepare these dye stuff 7. Sodium a-cyanoketene dithiolates 2 react with two moles of phenacyl bromide derivatives, forming alkylsulfanylthiophenes which react with the diazonium salt, forming the target dyestuff. These prepared dyes are used to print polyamide and polyester fabrics by using a synthetic thickener in the printing paste using screen-printing techniques.

Findings

The structure of synthesised dyes were established and confirmed for the reaction products on the basis of their elemental analysis and spectral data (IR and 1H-NMR). The suitability of the prepared dyestuffs for screen printing on polyamide and polyester fabrics has been investigated. The prints obtained from dyes possess high colour strength as well as excellent overall fastness properties.

Research limitations/implications

The diazo coupling reaction of the starting tetra-substituted thiophene 5 with diazotised aromatic amines resulted in the formation of the corresponding dye. The synthesised dyes were utilised in preparing a paste for polyester and polyamide fabric printing. In addition, both of the variations of the substituents on the synthesised dyes and the fastness properties were also studied.

Practical implications

The synthesised dyes are superior in terms of yield, purity, colour strength and fastness properties, which lead to valuable achievements for commercial production.

Social implications

The synthesised dyes are superior for application in fabrics.

Originality/value

The synthesis for novel thiophene-based dye stuff for application in printing properties on polyester and polyamide fabrics and study their fastness properties.

Article
Publication date: 19 May 2022

H. Abd El-Wahab and Raafat A. El-Eisawy

This paper aims to prepare new modified alkyd resins and use it as an antimicrobial binder for surface coating applications.

Abstract

Purpose

This paper aims to prepare new modified alkyd resins and use it as an antimicrobial binder for surface coating applications.

Design/methodology/approach

Various modified alkyd resins were prepared by partial replacement of 3,6-dichloro benzo[b]thiophene-2-carbonyl bis-(2-hydroxy ethyl)-amide as a source of polyol with glycerol and confirmed by acid value, FT-IR, 1H-NMR. The modified alkyd resins were covering a wide range of oil lengths and hydroxyl content (0%, 10%, 20% and 30% excess-OH). The antimicrobial activity of the prepared alkyds was also investigated. The coatings of 60 ± 5 µm thickness were applied to the surface of glass panels and mild steel strips by means of a brush. Physico-mechanical tests, chemical resistance and antimicrobial activities were investigated.

Findings

The obtained results illustrate that the introduction of benzo[b]thiophene derivative as a modifier polyol within the resin structure improved the film performance and enhanced the physico-mechanical characteristics, chemical resistance and the antimicrobial activities.

Practical implications

The modified alkyd resins can be employed as antimicrobial binders in paint compositions for a variety of surfaces, particularly those that are susceptible to a high number of bacteria.

Originality/value

Modified alkyd resins based on antimicrobial heterocyclic compounds have the potential to be promising in the manufacturing of antimicrobial coatings and development of paints, allowing them to function to prevent the spread of microbial infection, which is exactly what the world requires at this time. Also, they can be applied in different substrates for industrial applications.

Details

Pigment & Resin Technology, vol. 52 no. 6
Type: Research Article
ISSN: 0369-9420

Keywords

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: 12 February 2020

Sang Xiong, Jia Si, Jianlin Sun, Hao Wu, Hongchen Dong and Chao Zhang

Corrosion inhibitors for copper immersed in emulsion were investigated by experiments and theoretical calculations, and this study aims to propose a new inhibition mechanism of…

Abstract

Purpose

Corrosion inhibitors for copper immersed in emulsion were investigated by experiments and theoretical calculations, and this study aims to propose a new inhibition mechanism of the inhibitors having protective effects for copper corrosion.

Design/methodology/approach

Adsorption behavior of penta-heterocycles (thiophene, 1,2,5-oxadiazole, furan, 2 H-1,2,3-triazole, pyrrole and 1,2,5-thiadiazole) as corrosion inhibitors for copper immersed in oil-in-water (O/W) emulsions was investigated by weight loss, electrochemical tests, morphological characterization and theoretical calculations.

Findings

The orders of inhibition effect are furan < pyrrole < thiophene < 1,2,5-oxadiazole < 2H-1,2,3-triazole < 1,2,5-thiadiazole, and 1,2,5-thiadiazole at 0.5 mM has the best inhibition effect for copper immersed in emulsion. The results of scanning probe microscope, scanning electron microscope and electrochemical test show that a protective barrier can be formed on the surface of copper substrate with six corrosion inhibitors, thus effectively inhibiting the corrosion of copper mainly through chemisorption and following Langmuir’s adsorption isotherm.

Originality/value

Quantum chemical and molecular dynamic simulations demonstrate that all these compounds attached to Cu matrix with a flat-adsorption mode to prevent the emulsion corrode copper. Adsorbed inhibitors act as a barrier at Cu matrix to block corrosion and improve hydrophobicity.

Details

Anti-Corrosion Methods and Materials, vol. 67 no. 2
Type: Research Article
ISSN: 0003-5599

Keywords

Article
Publication date: 7 November 2016

H.E. Gaffer, S. Shaaban, N.A. Abed and E. Abdel-latif

This paper aimed to synthesise some new selenium-containing pyrazole, thiazole and thiophene dyestuffs and investigate their application in dyeing polyester fabrics.

Abstract

Purpose

This paper aimed to synthesise some new selenium-containing pyrazole, thiazole and thiophene dyestuffs and investigate their application in dyeing polyester fabrics.

Design/methodology/approach

4,4′-Diselanediyl-bis-(2-methoxyaniline) was diazotized by acetic acid/sodium nitrite and coupled with active methylene components such as malononitrile, ethyl cyanoacetate and ethyl acetoacetate, and their corresponding hydrazono products were cyclised with hydrazine or phenyl hydrazine to obtain a series of arylazo-pyrazole dyestuffs. Furthermore, diazo-coupling reactions of the diazotized 4,4′-diselanediyl-bis-(2-methoxyaniline) were developed to obtain a new series of 2-amino-5-arylazo-thiazole- and 4-aryazo-3-hydroxy-2-substituted thiophene dyestuffs.

Findings

The structure of the synthesised dyestuffs was established and confirmed based on their elemental analysis and spectral data (infrared, proton nuclear magnetic resonance and mass spectroscopies). The synthesised selenium-containing dyestuffs were applied as disperse dyes on polyester fabrics by high temperature-pressure technique. The dyeing characteristics of these dyestuffs were evaluated, and they were found to exhibit good fastness properties.

Originality/value

A series of symmetrical diselenide dyestuffs containing pyrazole, thiazole or thiophene coupler components were synthesised. The authors studied their application for dyeing polyester fabrics; they are superior in terms of preparation, yield, purity and fastness properties.

Details

Pigment & Resin Technology, vol. 45 no. 6
Type: Research Article
ISSN: 0369-9420

Keywords

Article
Publication date: 1 August 2014

F. A. Mohamed and R. M. Mohareb

Ethyl 2-diazo-4, 5, 6, 7-tetrahydrobenzo[b] thiophene-3-carboxylate is reacted with malononitrile to give a hydrazone derivative. The latter product is reacted with…

Abstract

Ethyl 2-diazo-4, 5, 6, 7-tetrahydrobenzo[b] thiophene-3-carboxylate is reacted with malononitrile to give a hydrazone derivative. The latter product is reacted with 1-diazobenzene-4-β-sulphatoethylsulphone (PABSES) to give a disperse dye. The dye is synthesised by diazotisation and coupling reactions. First, it is synthesised with the chromophoric moiety of ethyl 2-hydrazomalononitrilo-4,5,6,7-tetrahydrobenzo[b] thiopheen- 3-carboxylate and coupled with diazonium salts that have the aforementioned reactive groups, thus yielding the new target reactive. The synthesised dye is applied onto wool, polyester and wool-polyester (blend) fabrics under typical exhaust dyeing conditions and their dyeing properties are investigated. The structure of this dye is characterised and confirmed by melting point, elemental analysis, infrared, ultraviolet-visible spectroscopy (UV/VIS) and nuclear magnetic resonance (1H-NMR) data. The dyeing of polyester, wool and polyester/wool blend fabrics with a reactive disperse dye gives very good build up and fastness properties by using a nonionic vinylsulphone (VS) derivative, which increases the substantivity of the dye towards wool fabric. Maximum exhaustion as well as total fixation efficiency by using a sulfatoethylsulfone (SES)-based dye on wool fabric is achieved at a neutral pH of 7. This feature of the dye structure significantly improves the union dyeing of wool/polyester blend fabrics with very good build up and fastness properties.

Details

Research Journal of Textile and Apparel, vol. 18 no. 3
Type: Research Article
ISSN: 1560-6074

Keywords

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

1 – 10 of 93