Synthesis and characterization of reactive dyes based on 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid

A series of new quinazolinone based mono azo reactive dyes (D_1–10) have been prepared by subsequent diazotization of 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid (C) and coupling with various 4-chloro anilino cyanurated coupling components. These dyes give purple, red, orange and yellow color shades. All the reactive dyes were characterized by their percentage yield, UV–Vis spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy and dyeing performance on silk, wool and cotton fibres. The percentage dye bath exhaustion on different fibres has been found to be reasonably good and acceptable. The dyed fibres show moderate to very good light fastness and good to excellent washing and rubbing fastness.     

Synthesis and dyeing properties of some new monoazo disperse dyes derived from 2-amino-4-(2′,4′-dichlorophenyl)-1,3 thiazole

Ten new monoazo disperse dyes (4a–j) have been synthesized by coupling of diazotized 2-amino-4-(2′,4′-dichlorophenyl)-1,3 thiazole (2) with various N-alkyl derivatives of substituted aniline (3a–j) and their dyeing performance on polyester fiber has been assessed. These dyes are characterized by elemental analysis, UV–vis spectra, IR and NMR spectroscopy. The absorption maxima (λ_max) were recorded in DMF and were found to be in the range of 530–600 nm. The dyed polyester fabric showed fair to very good light fastness and very good to excellent washing and rubbing fastness properties with superior depth and levelness.     

Synthesis and spectral characterization of azo dyes derived from calix[4]arene and their application in dyeing of fibers

In this study, the synthesis and characterization of two new upper rim functionalized azocalix[4]arene dyes have been obtained by coupling calix[4]arene with different diazo compounds of 3,5-dicarboxyaniline and 4-aminobenzene sulphon amide. The characterization of these dyes has been carried out by elemental analysis, FT-IR and ¹H NMR spectra. The effect of varying dielectric constants of solvents on the absorption spectra of azocalix[4]arenes (1, 2, 3, 4) and commercial Isolan Gelb SGL (T) have been examined by UV–Vis spectrophotometer. These azocalix[4]arene dyes have also been used for dyeing textile fibers like cotton, wool, acetate, polyester and polyamide fibers. Their dyeing and fastness properties have also been discussed.     

Synthesis and dyeing properties of new disazo disperse dyes for polyester and nylon fabrics

Diazotized aryl amines were coupled with two stenhouse salt namely, N-(5-phenylamino-penta-4-ol-2,4-diene-1-ylidene)anilines hydrochloride [S₁ (RH) or S₂ (ROH)] to furnish two series of disazo disperse dyes (S₁D_1–10 and S₂D_1–10). The structure of all the dyes was established by estimating number of azo groups, elemental analysis and spectral studies (IR, ¹H-NMR, UV/Visible). The structure–property relationship was discussed by using electronic absorption spectra of the dyes. These dyes were applied to polyester and nylon fabrics as disperse dyes by using temperature exhaust dyeing method. The relevant dyeing characteristics, such as dyeability on fabrics, wash-fastness and light-fastness were evaluated. Fabrics dyed with these dyes furnished generally deep and bright intense hues ranging from light yellow to orange to reddish brown. The color fastness of the dyed fabric was assessed by determining wash-fastness and light-fastness properties.     

Synthesis,characterization and dyeing performance of new bisazo–bisazomethine disperse dyes

New bisazo–bisazomethine disperse dyes were prepared by the coupling of diazotized solutions of various aromatic amines with 2,2′-{methylenebis[4,1-phenylenenitrilomethylylidene]}diphenol (Schiff base). Schiff base (SB) was prepared by the condensation of 2-hydroxybenzaldehyde with 4,4′-diaminodiphenylmethane (DDM). The resultant dyes were characterized by elemental analysis, IR and ¹H NMR spectral studies. The UV–visible absorption spectral data were investigated in dimethylformamide (DMF) and are discussed in terms of structure property relationship. The dyes when applied on polyester fabric, gave golden yellow to reddish brown shades having fairly good to good light fastness, very good to excellent washing, perspiration and sublimation fastness and good to very good rubbing fastness properties.     

Synthesis and evaluation of a series of symmetrical hot brand bis azo reactive dyes using 4,4′-methylene-bis-metanilic acid on various fibre

4,4′-Methylene-bis-metanilic acid (A) was synthesized by the reaction between metanilic acid and formaldehyde. The compound (A) was used as a bifunctional middle component in the preparation of several symmetrical hot brand bis azo reactive dyes. The compound (A) was tetrazotized and coupled with various m-nitro anilino cyanurated coupling component to give various hot brand bis azo reactive dyes. The entired compounds have been identified by IR, ¹H NMR spectra and elemental analysis. The dyes were applied on silk, wool and cotton fabrics and their fastness properties were evaluated. All the dyes give good fastness properties. The percentage dye bath exhaustion was also been studied.     

Synthesis of some 4-arylazo-3-hydroxythiophene disperse dyes for dyeing polyester fabrics

A series of novel 4-arylazo-3-hydroxythiophene disperse dyes was synthesized by heterocyclization of ethyl 2-arylhydrazono-2-phenylthiocarbamoyl acetates with a variety of α-halogenated reagents. The structures of the synthesized dyes were confirmed by UV-Vis, IR, ¹H NMR, and MS spectroscopic techniques and elemental analysis. The dyes were applied to conventional polyester fabric by high temperature exhaust dyeing. These dyes were found to give orange to reddish-violet shades with very good depth, levelness, and brightness on polyester fabric. The dyed fabric showed moderate to good light fastness and very good fastness to washing and perspiration. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed.     

Substituted 5-Antipyrinylazo-4-phenyl-2-aminothiazoles as Disperse Dyes for Dyeing Polyester Fabrics

Summary. A series of some new substituted 5-antipyrinylazo-4-phenyl-2-aminothiazole disperse dyes was synthesized by diazocoupling of 4-antipyrinyldiazonium chloride with aminothiazole derivatives. The synthesized dyes were characterized by UV-Vis absorption, IR, ¹H NMR, and MS spectroscopy. The dyes gave orange to reddish-violet shades with very good depth and levelness when applied to polyester fabrics as disperse dyes and their fastness properties were evaluated on polyester fibers. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed.     

Substituted 5-Antipyrinylazo-4-phenyl-2-aminothiazoles as Disperse Dyes for Dyeing Polyester Fabrics

A series of some new substituted 5-antipyrinylazo-4-phenyl-2-aminothiazole disperse dyes was synthesized by diazocoupling of 4-antipyrinyldiazonium chloride with aminothiazole derivatives. The synthesized dyes were characterized by UV-Vis absorption, IR, ¹H NMR, and MS spectroscopy. The dyes gave orange to reddish-violet shades with very good depth and levelness when applied to polyester fabrics as disperse dyes and their fastness properties were evaluated on polyester fibers. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed.     

Characterization,DFT calculations and dyeing performance on polyester fabrics of some azo disperse dyes containing pyrazole ring

A number of azo pyrazole derivatives and novel Schiff bases derived from azo diamino pyrazole were synthesized. These included 4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines and N³,N⁵-dibenzylidene-4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines. The chemical structures of the novel azo dyes were determined using UV–visible, IR, ¹H NMR, and ¹³C NMR spectroscopy. Dyeing process and tautomerism of the aforementioned azo compounds were predicted using DFT calculations. The electronic absorption spectra in methanol were observed and compared to those computed using B3LYP/6-31G(d,p). The dyeing performance of the produced disperse dyes was examined on polyester. The degree of exhaustion and the fastness properties of the dyed samples in terms of washing, perspiration, scorch, and light fastness were assessed. Moreover, the reflectance and color strength of the synthesized dyes were measured and discussed.     

Synthesis of Some Novel Biologically Active Disperse Dyes Derived from 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as Coupling Component and Their Colour Assessment on Polyester Fabrics

A series of novel azo-disperse dyes containing alkylhydrazonopyridinone structures were synthesized. 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitrile (8) is synthesized by one-pot synthesis using ethyl cyanoacetate, propylamine, and ethyl acetoacetate. Compound 8 is then coupled with aromatic and heteroaromatic diazonium salts to afford the corresponding aryl- and heteroaryl-4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitriles 12a,b and 13a-c. Structural assignments to the dyes were made using NMR spectroscopic methods. A high temperature dyeing method was employed to apply these dyes to polyester fabrics. Most of the dyed fabrics tested displayed very good light fastness levels and good wash fastness. Finally, the biological activity of the prepared dyes against Gram positive bacteria and Gram negative bacteria were evaluated.     

Synthesis of some 4-arylazo-3-hydroxythiophene disperse dyes for dyeing polyester fabrics

A series of novel 4-arylazo-3-hydroxythiophene disperse dyes was synthesized by heterocyclization of ethyl 2-arylhydrazono-2-phenylthiocarbamoyl acetates with a variety of α-halogenated reagents. The structures of the synthesized dyes were confirmed by UV-Vis, IR, ¹H NMR, and MS spectroscopic techniques and elemental analysis. The dyes were applied to conventional polyester fabric by high temperature exhaust dyeing. These dyes were found to give orange to reddish-violet shades with very good depth, levelness, and brightness on polyester fabric. The dyed fabric showed moderate to good light fastness and very good fastness to washing and perspiration. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed. Correspondence: Ehab Abdel-Latif, Department of Chemistry, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt     

Synthesis of new reactive dyes containing commercial UV-absorbers with enhanced simultaneous dyeing and anti-UV properties for cotton fabric

Two new reactive anti-UV dyes were synthesized based on two commercial UV-absorbers, ethyl 4-aminobenzoate for dye 1 and 4-aminobenzophenone for dye 2, which were incorporated in a structure modified from commercial reactive dye CI Reactive Red 198 (dye 3). Optimum exhaustion and total fixation values were achieved at 80 ​g/l sodium sulphate for dye 1 and 60 ​g/l sodium sulphate for dye 2, 20 ​g/l sodium carbonate at 70 ​°C for dye 1 and 80 ​°C for dye 2 and 60 ​min fixation time for both dyes. The two new reactive dyes exhibited higher dyeing properties and UPF values than the commercial reactive dye over all the dye concentrations studied. The new reactive dye 1 achieved the highest exhaustion, total fixation and UPF values. The fastness properties obtained for all the dyeings ranges from good to excellent.     

The synthesis and characterization of calix[4]arene based azo dyes

A series of azocalix[4]arene dyes (1–7) were prepared by linking 2,4-di-chloroaniline, 2,4,5-tri-chloroaniline, 2,4-di-nitroaniline, 2-nitro p-toluidin, 4-nitro o-toluidin, 5-nitro o-toluidin and sulfanilic acid, to calix[4]arene through a diazo-coupling reaction. These compounds were characterized by elemental analysis, FT-IR, ¹H NMR, ¹³C NMR, MALDI-TOF, UV–Vis., DSC, and DTA. The absorption properties of the synthesized dyes were studied and the application of the water soluble dye on cotton and wool was discussed. Solvent based inks were investigated and the fastness properties of formulated inks were also discussed.     

Silicone nanomicelle dyeing method on polyester fibre: Comparative evaluation of chemical properties,fastness properties,and DFT

Disperse Red 177(9a), Disperse Red 343(9b), Disperse Blue 165(9c), Disperse Blue 165.1(9d), Disperse Blue 366(9e), and Disperse Blue 148(9f) were examined in the solvent. During silicon nanomicelle dyeing, we employed 9(a–f) azo disperse dyes on polyester. On polyester fabric, dye 9(a–f) offers equal washing, light, and rubbing fastness in both the conventional and silicone nanomicelle techniques. The dye can now be transported directly into the fibre core without the use of auxiliary dyes owing to the reduction in the particle size of azo dyes, which is made possible by nanoemulsions superior dispersion. The levelling property of the dispersed dye is enhanced by the dyeing process. When both techniques are applied, the lightfastness properties of all dyes are improved. It provides a very good to outstanding protection factor for textile materials. These 9(a–f) azo disperse dyes have moderate to outstanding photostability, net electrophilicity index, and lightfastness.     

Pyrene-tethered bismoviologens for visible light-induced C(sp3)–P and C(sp2)–P bonds formation

Developing efficient photosensitizers for C–P bond construction is highly important and remains a challenge due to the urgently needed for the synthesis of modified nucleosides, nucleotides, and other phosphine-containing ligands. Herein, two pyrene-tethered bismoviologen derivatives (Py-BiV²⁺) were designed and synthesized for visible-light-induced C–P bonds formation. The photochemical and electrochemical properties of Py-BiV²⁺ were studied systemically, certifying fine-tunable opto-electronic properties through the number of pyrene groups (4, n = 1; 6, n = 2). The prepared Py-BiV²⁺ showed strong light absorption, while retaining good redox features and chromic response features that were inherent to viologens. 4 exhibited accelerated photoinduced electron transfer in the presence of the electron donor (pyrene) and the generated 4′ (radical cation) showed higher stability. Accordingly, Py-BiV²⁺ directly served as photosensitizers for the first time in the visible-light-induced C(sp³)–P and C(sp²)–P bonds formation. As expected, these novel viologen derivatives exhibited good catalytic performance and good substrate expansibility under ambient conditions.     

Colorimetric studies of heterocyclic monoazo reactive dyes and their dyeing applications on cotton,silk, and wool fibers

Heterocyclic quinazolinone-based hot brand monoazo reactive dyes were obtained by diazotization of 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one and coupling with a variety of cyanurated coupling components. All the heterocyclic hot brand monoazo reactive dyes were characterized by elemental analysis (C, H, N) and by use of spectroscopic techniques (FT-IR, UV–visible, ¹H NMR). Their performance as reactive dyes was assessed on silk, wool, and cotton fabrics. The dyes were found to give a variety of color shades with very good depth and uniformity on the fibers. The fastness of all the dyes on the fibers was moderate to excellent. Colorimetric data (L*, a*, b*, C*, H*, and K/S) of the synthesized dyes were also studied in detail.     

Synthesis,antimicrobial and cytotoxic activity of novel azetidine-2-one derivatives of 1H-benzimidazole

A series of 1-methyl-N-[(substituted-phenylmethylidene)-1H-benzimidazol-2-amines (4a–4g) were prepared via the formation of 1-methyl-1H-benzimidazol-2-amine (3), which was prepared by the cycloaddition of o-phenylenediamine (1) with cyanogen bromide in the presence of aqueous base followed by N-methylation with methyl iodide in the presence of anhydrous potassium carbonate in dry acetonitrile. Moreover, the four-membered β-lactam ring was introduced by the cycloaddition of 4a–4g and chloroacetyl chloride in the presence of triethylamine catalyst to give 3-chloro-1-(1-methyl-1H-benzimidazol-2-yl)-(4′-substituted)-phenylazetidin-2-one 5a–5g. A total of 14 compounds were synthesized and characterized by IR, ¹H NMR, ¹³C NMR and Mass spectral technique, in addition they were evaluated for anti-bacterial and cytotoxic properties. Among the chemicals tested 4a, 4b, 5a, 5b, 5g exhibited good antibacterial activity and 5f, 5g shown good cytotoxic activity in vitro.     

Novel thiosemicarbazone derivatives containing benzimidazole moiety: Green synthesis and anti-malarial activity

A series of (E)-2-[5-chloro-1-(1H-benzo[d]imidazol-2-yl)ethylidene] N-(substituted) hydrazine carbothioamide (7a–7t) and (E)-2-[1-(1H-benzo[d]imidazol-2-yl)ethylidene] N-(substituted) hydrazine carbothioamide (8a–8t) were prepared via the synthesis of 1-(substituted-1H-benzimidazol-2-yl) ethanol (3a–3b) which was synthesized by the condensation of substituted o-phenylenediamine (2a–2b) with dl-lactic acid (1) followed by oxidation with sodium hypochlorite in mild acidic condition to form the corresponding ketones 4a–4b. Final compounds were formed by condensation of 4a–4b with different thiosemicarbazides 6a–6t. A total of 40 compounds were synthesized and characterized by FT-IR, ¹H NMR, ¹³C NMR, Mass spectral technique and elemental analysis, in addition they were evaluated for anti-malarial properties. Among the compounds tested 7o, 7p, 7q, 7r, 7s, 8e and 8h exhibited good antimalarial activity in vitro.     

Incorporation of Triarylmethane Dyes into Sol–Gel Matrices Deposited on Textiles

The incorporation of triarylmethane dyes into sol–gel layers formed by modified silica was used for coating of textile materials. The coatings were performed with three triarylmethane dyes differ in electrical net charge and structure: The cationic dye Malachite Green, the anionic Guinea Green and the non-polar Reflex Blue 61. All coating procedures were performed using an acidic sol–gel process starting from a solution of tetraethoxysilane (TEOS) and the dye in a mixture of water and ethanol. Depositions were performed on polyester, polyamide and cotton textiles. Investigation of leaching and photobleaching fastness showed that the stability of the dyes was enhanced by incorporation into the silica layer. Sufficient leaching fastness was only achieved with the cationic dye due to direct attractive electrostatic interaction with the negatively charged silica matrix. Also the addition of a small amount of epoxysilane to the silica sols lead to an enhancement of leaching and bleaching fastness.