Synthesis of 4-hydroxy coumarin dyes and their applications

2016 ◽  
Vol 45 (5) ◽  
pp. 320-329 ◽  
Author(s):  
Hatem Gaffer ◽  
Mounir Salem ◽  
Magda Marzouk
Keyword(s):  
Azo Dyes ◽  
Antioxidant Activities ◽  
Fastness Properties ◽  
Transfer Printing ◽  
Polyester Fabrics ◽  
Content Type ◽  
Colour Strength ◽  
Textile Dyeing ◽  
Hydroxy Coumarin ◽  
Decisive Evidence

Purpose The present study aims to focus on the possibility of developing new eco-friendly azo dyes with good colouristic application properties, exhibiting biological and pharmacological activities. Design/methodology/approach Coupling of 4-hydroxycoumarin with a variety of aromatic diazonium salts of 2-aminothiazole, 2-aminobenzothiazole, 4-aminoantipyrine, 4-aminoacetophenone, adenine sulphate, a-naphthylamine and sulphadimidine to produce novel azo dyes. The compounds were fully characterised using spectroscopic and analytical methods. All of the compounds were tested for their antimicrobial, anticancer and antioxidant activities. The prepared dyestuffs were dyed on polyester fabrics and subsequently their dyeing properties, light, washing, perspiration, rubbing and sublimation fastness were determined. Findings The spectroscopic data of the synthesised compounds have provided decisive evidence that such compounds exist in the solid state as the azo-dike to form C and in solution in equilibrium tautomer forms A, B and D. The prepared dyestuffs are suitable for either heat transfer printing or traditional printing on polyester and nylon 6 fabrics. The prints obtained from the dyes possess high colour strength, as well as good overall fastness properties. Also the synthesised compounds exhibit good biological and pharmacology activity. Research limitations/implications Synthesis of these seven azo dyes for textile dyeing had never been reported previously. Practical implications The dyestuffs derived from 4-hydroxycoumarin are reasonable azo disperse dyestuffs giving good all round fastness properties on polyester fabrics. Social implications Production of less expensive and new eco-friendly dyes exhibit antimicrobial and anticancer activity. Originality/value It provided a potentially simple way to synthesize novel coumarin azo-dyes exhibit good biological and pharmacology activity and also exhibit good overall fastness properties.

Synthesis of novel biologically active thiazole dyes and their applications

2019 ◽  
Vol 48 (5) ◽  
pp. 375-382
Author(s):  
Sraa Abu-Melha
Keyword(s):  
Azo Dyes ◽  
Antioxidant Activities ◽  
Biologically Active ◽  
Disperse Dyes ◽  
Fastness Properties ◽  
Thiazole Derivatives ◽  
Polyester Fabrics ◽  
Content Type ◽  
Colour Strength ◽  
Textile Dyeing

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.

Synthesis of novel tetrasubstituted thiophenes based dye using sodium a-cyanoketene dithiolates as starting materials

2015 ◽  
Vol 44 (6) ◽  
pp. 339-346 ◽  
Author(s):  
G.H. Elgemeie ◽  
K.A. Ahmed ◽  
E.A. Ahmed ◽  
M.H. Helal ◽  
D.M. Masoud
Keyword(s):  
Screen Printing ◽  
Diazonium Salt ◽  
Phenacyl Bromide ◽  
Fastness Properties ◽  
Reaction Products ◽  
Polyester Fabrics ◽  
Content Type ◽  
Colour Strength ◽  
Starting Point ◽  
Diazo Coupling

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.

Fruit shells of Camellia oleifera Abel as natural colourants for pigment printing of cotton fabric

2017 ◽  
Vol 46 (1) ◽  
pp. 56-63 ◽  
Author(s):  
Monthon Nakpathom ◽  
Buppha Somboon ◽  
Nootsara Narumol ◽  
Rattanaphol Mongkholrattanasit
Keyword(s):  
Cotton Fabric ◽  
Textile Industry ◽  
Camellia Oleifera ◽  
Fastness Properties ◽  
Light Fastness ◽  
Content Type ◽  
Colour Fastness ◽  
Colour Strength ◽  
Screen Printing Technique ◽  
First Time

Purpose The present study aims to focus on the feasibility of using an aqueous extract from the fruit shell of Camellia oleifera Abel as a source of natural colourant in printing-paste preparation for pigment printing of cotton fabric. The effects of pre- and post-mordanting with three common metallic mordants, that is AlK(SO4)2, CuSO4 and FeSO4 on colour yield and colour fastness properties are also investigated. Design/methodology/approach The printing paste was prepared by mixing the concentrated Camellia oleifera Abel fruit shell extract solution with commercially available synthetic thickener and binder. The fabric sample was printed with the prepared printing paste using a flat-screen printing technique. To determine the effects of pre- and post-mordanting, AlK(SO4)2, CuSO4 and FeSO4 mordant aqueous solutions with various concentrations were applied using the pad-dry technique. Comparisons between printing with and without mordants were evaluated in terms of colour strength (K/S values) and colour fastness to washing, light, crocking and perspiration. Findings Without the mordants, the printed fabric had a yellowish brown shade with acceptable colour fastness properties, that is fair to good wash fastness, moderate light fastness, good to very good crocking fastness and fair to good perspiration fastness. The use of mordants, especially CuSO4 and FeSO4, not only enhanced colour strength but also imparted different colours to the fabric. Compared to the unmordanted fabrics, colour fastness properties were mostly comparable or improved in the mordanted fabrics depending on the type and concentration of mordants. Research limitations/implications Although in the case of CuSO4 the light fastness was increased to a good to very good level, it is recommended that the final print be produced with a concentration of less than 0.125 gL−1 to yield the print with the residual amount of Cu metal under the limit, that is less than 50 ppm as regulated by the Oeko-Tex® standard. Practical implications The obtained prints from Camellia oleifera Abel fruit shell extract provided shades with satisfactory colour fastness to washing, light, crocking and perspiration. The extract from Camellia oleifera Abel fruit shell has the potential to be used as an alternative to synthetic dye in the textile industry. Originality/value The use of Camellia oleifera Abel fruit shells, which are considered as abundant byproducts of tea seed oil production, as natural colouring agents for pigment printing of cotton fabric has been reported for the first time. It will minimise the environmental impact of this waste and create more valuable textile products.

A simple approach for the synthesis of coumarin fluorescent dyes under microwave irradiation and their application in textile printing

2016 ◽  
Vol 45 (4) ◽  
pp. 217-224 ◽  
Author(s):  
G.H. Elgemeie ◽  
K.A. Ahmed ◽  
E.A. Ahmed ◽  
M.H. Helal ◽  
D.M. Masoud
Keyword(s):  
Optical Properties ◽  
Microwave Irradiation ◽  
Fluorescent Dyes ◽  
Fastness Properties ◽  
Reaction Products ◽  
Light Fastness ◽  
Content Type ◽  
Colour Strength ◽  
Silk Screen ◽  
New Generation

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.

scholarly journals Diphenyl (4′-(Aryldiazenyl)biphenyl-4-ylamino)(pyridin-3-yl)methylphosphonates as Azo Disperse Dyes for Dyeing Polyester Fabrics

2013 ◽  
Vol 2013 ◽  
pp. 1-5
Author(s):  
Mohamed F. Abdel-Megeed ◽  
Mohamed M. Azaam ◽  
Gamal A. El-Hiti
Keyword(s):  
Azo Dyes ◽  
Titanium Tetrachloride ◽  
Diazonium Salt ◽  
Disperse Dyes ◽  
Fastness Properties ◽  
Polyester Fabrics ◽  
Amino Compounds ◽  
Azo Disperse Dyes

Diphenyl (4′-aminobiphenyl-4-ylamino)(pyridin-3-yl)methylphosphonate(1)was synthesized in 88% yield from reaction of pyridine-3-carboxaldehyde with benzidine and triphenylphosphite in the presence of titanium tetrachloride as a catalyst. Diazotization of1gave the corresponding diazonium salt2which was coupled with several hydroxyl or amino compounds to give the corresponding azo dyes3–8in 82–88% yields after crystallization. The dyes produced were applied to polyesters as disperse dyes and their fastness properties were elevated.

scholarly journals Synthesis of Novel Biologically Active Thiazole Dyes and Their Applications

2018 ◽  
Author(s):  
Sarra Abu-Melha
Keyword(s):  
Azo Dyes ◽  
Biologically Active ◽  
Diazonium Salts ◽  
Spectroscopic Techniques ◽  
Fastness Properties ◽  
Thiazole Derivatives ◽  
Pharmacological Activities ◽  
Polyester Fabrics ◽  
Dyeing Properties

This work is aiming to motivation on the prospect of evolving new thiazole dyes with respectable application properties, expected pharmacological activities. Curcumin Coupling with diverse diazonium salts of 2-amino thiazole derivatives as 2-aminobenzothiazole, 2- amino-5-phenylthiazole, 2 amino-5-methylthiazole and 2 amino-5-nitrothiazole to produce novel azo dyes. All synthesised dyes were completely confirmed their structures via elemental and spectroscopic techniques. The synthesised thiazole derivatives were examined for their “antimicrobial, anticancer and antioxidant” activities. All of the synthesized dyes were applied on synthetic fabrics as polyester and successively their dyeing properties, “light, washing, perspiration, rubbing and sublimation” fastness were evaluated. Prepared dyestuffs are suitable for dyeing polyester fabrics. It was initiate that all of prepared dyes own extraordinary colour hue, along with respectable fastness properties. Also the synthesised thiazole derivatives display moral pharmacology activity.

Synthesis of novel dyes based on thiophene analogues with antibacterial activity for dyeing polyester fabrics

2019 ◽  
Vol 48 (4) ◽  
pp. 337-347 ◽  
Author(s):  
Hanna Abomelha
Keyword(s):  
Polyester Fabric ◽  
Gram Negative Bacteria ◽  
Antibacterial Efficacy ◽  
Fastness Properties ◽  
Gram Positive ◽  
Standard Drug ◽  
Gram Negative ◽  
Polyester Fabrics ◽  
Content Type ◽  
Diazo Coupling

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.

Synthesis of some new symmetrical diselenide dyestuffs for dyeing polyester fabrics

2016 ◽  
Vol 45 (6) ◽  
pp. 431-438 ◽  
Author(s):  
H.E. Gaffer ◽  
S. Shaaban ◽  
N.A. Abed ◽  
E. Abdel-latif
Keyword(s):  
Ethyl Cyanoacetate ◽  
Proton Nuclear Magnetic Resonance ◽  
Disperse Dyes ◽  
Coupling Reactions ◽  
Fastness Properties ◽  
Phenyl Hydrazine ◽  
Polyester Fabrics ◽  
Content Type ◽  
Diazo Coupling ◽  
Active Methylene

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.

scholarly journals A Caleosin-Like Protein with Peroxygenase Activity Mediates Aspergillus flavus Development, Aflatoxin Accumulation, and Seed Infection

2015 ◽  
Vol 81 (18) ◽  
pp. 6129-6144 ◽  
Author(s):  
Abdulsamie Hanano ◽  
Ibrahem Almousally ◽  
Mouhnad Shaban ◽  
Elizabeth Blee
Keyword(s):  
Fatty Acid ◽  
Aspergillus Flavus ◽  
Polyunsaturated Fatty Acid ◽  
Calcium Binding ◽  
Antioxidant Activities ◽  
Fungal Growth ◽  
Oxidation Reactions ◽  
Content Type ◽  
Fatty Acid Hydroperoxides

ABSTRACTCaleosins are a small family of calcium-binding proteins endowed with peroxygenase activity in plants. Caleosin-like genes are present in fungi; however, their functions have not been reported yet. In this work, we identify a plant caleosin-like protein inAspergillus flavusthat is highly expressed during the early stages of spore germination. A recombinant purified 32-kDa caleosin-like protein supported peroxygenase activities, including co-oxidation reactions and reduction of polyunsaturated fatty acid hydroperoxides. Deletion of the caleosin gene prevented fungal development. Alternatively, silencing of the gene led to the increased accumulation of endogenous polyunsaturated fatty acid hydroperoxides and antioxidant activities but to a reduction of fungal growth and conidium formation. Two key genes of the aflatoxin biosynthesis pathway,aflRandaflD, were downregulated in the strains in whichA. flavusPXG(AfPXG) was silenced, leading to reduced aflatoxin B1 productionin vitro. Application of caleosin/peroxygenase-derived oxylipins restored the wild-type phenotype in the strains in whichAfPXGwas silenced.PXG-deficientA. flavusstrains were severely compromised in their capacity to infect maize seeds and to produce aflatoxin. Our results uncover a new branch of the fungal oxylipin pathway and may lead to the development of novel targets for controlling fungal disease.

scholarly journals Nine novel psychrotolerant species of the genus Pedobacter isolated from Arctic soil with potential antioxidant activities

2020 ◽  
Vol 70 (4) ◽  
pp. 2537-2553 ◽  
Author(s):  
Ram Hari Dahal ◽  
Dhiraj Kumar Chaudhary ◽  
Dong-Uk Kim ◽  
Jaisoo Kim
Keyword(s):  
Type Strain ◽  
Antioxidant Activities ◽  
Rrna Gene ◽  
Major Polar Lipid ◽  
Strictly Aerobic ◽  
The Novel ◽  
Content Type ◽  
Link Type ◽  
Arctic Soil ◽  
Type Strains

Fifteen isolates of the genus Pedobacter were obtained from Arctic soil samples. All isolates were Gram-stain-negative and rod-shaped. Cells were strictly aerobic, psychrotolerant and grew optimally at 15–20 °C. Phylogenetic analysis based on 16S rRNA gene sequences revealed that all the isolated strains formed a lineage within the family Sphingobacteriaceae and clustered as members of the genus Pedobacter . The sole respiratory quinone was MK-7 and the major polar lipid was phosphatidylethanolamine. The major cellular fatty acids were summed feature 3 (iso-C15 : 02-OH/C16 : 1ω7c/ω6c), iso-C15 : 0 and iso-C17 : 0 3-OH. The DNA G+C content of the novel strains was 33.9–41.8 mol%. In addition, the average nucleotide identity and in silico DNA–DNA hybridization relatedness values between the novel type strains and phylogenetically related type strains were below the threshold values used for species delineation. Based on genomic, chemotaxonomic, phenotypic, phylogenetic and phylogenomic analyses, the isolated strains represent novel species in the genus Pedobacter , for which the names Pedobacter cryotolerans sp. nov. (type strain AR-2-6T=KEMB 9005-717T=KACC 19998T=NBRC 113826T), Pedobacter cryophilus sp. nov. (type strain AR-3-17T=KEMB 9005-718T=KACC 19999T=NBRC 113827T), Pedobacter frigiditerrae sp. nov. (type strain RP-1-13T=KEMB 9005-720T=KACC 21147T=NBRC 113829T), Pedobacter psychroterrae sp. nov. (type strain RP-1-14T=KEMB 9005-721T=KACC 21148T=NBRC 113830T), Pedobacter hiemivivus sp. nov. (type strain RP-3-8T=KEMB 9005-724T=KACC 21152T=NBRC 113833T), Pedobacter frigidisoli sp. nov. (type strain RP-3-11T=KEMB 9005-725T=KACC 21153T=NBRC 113927T), Pedobacter frigoris sp. nov. (type strain RP-3-15T=KEMB 9005-726T=KACC 21154T=NBRC 113834T), Pedobacter psychrodurus sp. nov. (type strain RP-3-21T=KEMB 9005-728T=KACC 21156T=NBRC 113835T) and Pedobacter polaris sp. nov. (type strain RP-3-22T=KEMB 9005-729T=KACC 21157T=NBRC 113836T) are proposed.

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