Synthesis and microbial studies of N-phenyl-2-(4-phenyl-thiazol-2-ylamino)-acetamide based disperse dyes and their dyeing performance on polyester fiber

Azo disperse dyes (D₁-D₁₃) were prepared by various diazotized aryl amines coupled with N-(phenyl)-2-[(4-phenyl-1,3-thiazol-2-yl)amino] acetamide. All the azo disperse dyes have been characterized by their percentage yield, UV-VIS spectroscopy, elemental analysis, IR spectroscopy, ¹H-NMR spectroscopy, and dyeing performance on polyester fiber. These dyes were applied to polyester fabric by HTHP method and their fastness properties were evaluated. All the dyes gave moderate to excellent fastness properties on polyester fiber. The main focus was to synthesize azo disperse dyes that give good dyeing property along with pharmacological activity. Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.     

Synthesis, characterization and application of quinazolinone based reactive dyes for various fibers

Seven hot brand heterocyclic mono azo reactive dyes (7a–g) have been synthesized by coupling diazotized 2-phenyl-3{4′-[(4″-aminophenyl)sulphonyl]phenyl}-quinazoline-4(3H)-one-6-sulphonic acid (4) with various 2-chloro-4-nitro anilino cyanurated coupling components (6a–g) and their dyeing performance on silk, wool, and cotton has been assessed. The purity of dyes was checked by thin layer chromatography. These dyes were identified by recording IR and ¹H-NMR spectra. The λ _max, R _f value, %exhaustion, %fixation, light fastness, wash fastness, rubbing fastness, reflectance (%R) value, and K/S value have also been studied.     

Synthesis and evaluation of a series of novel monoazo disperse dyes derived from N-carboxylic acid-1,8-naphthalimide on poly(ethylene terphthalate)

A series of novel monoazo disperse dyes based on N-carboxylic acid-1,8-naphthalimides have been synthesized via 4-(4-amino-1,8-naphthalimido) butanoic acid as diazo components and various couplers. The synthesized dyes were characterized with elemental analysis, differential scanning colorimetry, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, and UV-visible spectroscopic techniques. The molar extinction coefficient, wavelength maxima, and solvatochromism effect were obtained using chloroform, acetone, and N,N-dimethyl formamide as solvent. The results showed that the synthesized dyes had molar extinction coefficient of 20908 to 38939 l mol⁻¹ cm⁻¹, wavelength maxima of 409–549 nm, and positive solvatochromism by changing solvent from chloroform to N,N-dimethyl formamide. The synthesized dyes were applied on poly(ethylene terephthalate) using high temperature method. Dyes 1 and 2 showed high build-up properties on poly(ethylene terephthalate), whereas dyes 3 and 4 offered medium build-up. All the dyes offered excellent heat fastness, good wash and rubbing fastnesses on poly(ethylene terephthalate) fabrics. The hydrolysis of the synthesized dyes in alkali media indicated that the presence of a carboxylic acid group within the dye molecules provides alkali-clearable potential.     

Azo Acid Dyes Based on 2H-Pyrido[1,2-a]Pyrimidine-2,4(3H)-Dione with Good Tinctorial Power and Wetfastness - Synthesis,Photophysical Properties,and Dyeing Studies

A series of five azo acid dyes were synthesized using different diazotized aromatic amine sulfonic and carboxylic acids followed by coupling with 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione. The dyes were characterized by ¹H-NMR, ¹³CNMR, FTIR, and elemental analysis. They were applied on nylon, silk, and wool. Their fastness properties were evaluated and color on the fabric was assessed. Yellow, brown, and crimson dyeings with good fastness properties were obtained. The dyes are water soluble and showed absorption from 380 nm to 550 nm. Acid dyes from diazo component 4- aminonaphthalene-1-sulfonic acid (naphthionic acid) and 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid (H-Acid) were found to be more red shifted as compared to the other dyes. More red shifted absorption maximum was observed in acidic pH than in alkaline pH. The trends in vertical excitations obtained from Time Dependent Density Functional Theory calculations are in good agreement with the experimental absorptions.     

Dispersant-free dyeing of poly(lactic acid) knitted fabric with temporarily solubilized azo disperse dyes

Poly(lactic acid) (PLA) is known for environmentally friendly material as it is derived from annually renewable crops and biodegradable. Dispersant-free dyeing of PLA fabric with three temporarily solubilized azo disperse dyes which contain β-sulfatoethylsulfonyl group was investigated and their dyeing and fastness properties were compared with those of commercial disperse dyes. The temporarily solubilized azo disperse dyes were successfully applied to PLA fabric without the use of dispersant. The color yield on PLA fabric was dependent on dyebath pH and dyeing temperature as well. The optimum results were obtained at pH 7-8 and 110 °C. The dyes showed markedly higher color yield on PLA fabric when compared to commercial disperse dyes. Wash fastness was very poor to poor but light fastness was good. The COD levels of the dyeing effluent from the temporarily solubilized disperse dyes were considerably lower than those from commercial disperse dyes.     

Synthesis of some new thermally stable reactive dyes having 4(3<Emphasis Type="Italic">H</Emphasis>)-quinazolinone molecule for the dyeing of silk,wool, and cotton fibers

Diazotized 3-{4-[2-chloro-4-amino-5-carboxybenzyl]-5-chloro-2-carboxyphenyl}-6-iodo-2-phenylquinazolin-4(3H)-one (4) was coupled with various p-nitro anilino cyanurated coupling components (6a-j) to give the corresponding quinazolinone based reactive dyes (7a-j) in reasonable yields. All the reactive dyes (7a-j) were characterized by spectroscopic technique and elemental analysis. These dyes were applied to silk, wool, and cotton fibers as reactive dyes and their spectroscopic data, colorimetric data, antimicrobial activity, thermal stability, and fastness properties were evaluated.     

Dyeing, color fastness and antimicrobial properties of some mono and disazo disperse dyes derived from thiazole moiety

Three series of mono and disazo disperse dyes were synthesized from 2-amino-4-(pyridin-3-yl) thiazole. The structure of the synthesized dyes was confirmed by elemental analysis, ultraviolet-visible, infrared, proton and carbon nuclear magnetic resonance and mass spectroscopy. The dyeing parameters, perspiration, wash and light fastness of eighteen azo disperse dyes on polyester have been investigated. Application of these dyes on polyester fabric gave yellow to reddish hues for mono azo derivatives and reddish to dark brown hues for disazo derivatives with fair to moderate light fastness and moderate to good wash and perspiration fastness grade. In addition, the synthesized dyes were screened for their antimicrobial activities against some gram positive, gram negative bacteria and fungi. Some of the prepared dyes gave excellent results against most of the tested organisms.     

Fabrication of novel multifunctional hybrid materials for PET/PA6 nonwoven fabrics finishing

A series of some novel hybrid materials prepared via a sol-gel process have been synthesized from methyltrimethoxysilane and titanium n-butoxide with heterocyclic thiazole azo dyes. Silica/titania/thiazole azo dyes hybrid materials were synthesized via a sol-gel process with a precursor system. Alternatively, the heterocyclic thiazole azo dyes were catalytically processed by means of hydrolysis-condensation reactions with appropriate amounts of a mixture of vinyltriethoxysilane, methyltrimethoxysilane, and titanium n-butoxide at a fixed molar ratio. The structure of these hybrid silica/titania/thiazole dye materials was characterized by Fourier transform infrared (FT-IR) analysis. The surface morphology of processed PET/PA6 nonwoven fabrics was evaluated by scanning electron microscopy (SEM). SEM images showed uniform dyeing, thereby confirming the reaction of the hybrid materials with the PET/PA6 nonwoven fabrics. The water contact angle, washing fastness, color evenness, air permeability, and weatherability characteristics of the as-prepared dyed PET/PA6 nonwoven fabrics were subsequently evaluated. Results revealed improved weatherability and good water repellency. Further, it was also revealed that dyeing and finishing could be achieved in a single bath, which is advantageous to reduce processing costs.     

Dyeing performance of disperse dyes based on 2-aminothiazole for cellulose triacetate and nylon fibers

A series of monoazo disperse dyes based on 2-amino-4-phenylthiazole was prepared using variousN,N-dialkylaniline derivatives as the coupling component. The dyes were characterized by IR spectral studies, visible absorption spectroscopy and elemental analysis. The dyeing performance of these dyes was assessed on cellulose triacetate and nylon fibers. These dyes were found to give a wide range of colour shades varying from bright red to royal blue with very good depth, brightness and levelness on fibers. The dyed fibers showed good to very good light fastness and very good to excellent fastness to washing, perspiration, rubbing and sublimation. The dyebath exhaustion and fixation on the fibers were found to be very good.     

Eco-friendly dyeing of poly(trimethylene terephthalate) with temporarily solubilized azo disperse dyes based on pyridone derivatives

Dispersant-free PTT dyeing of temporarily solubilized azo disperse dyes based on pyridone moiety which contain β-sulfatoethylsulfonyl group was investigated. The dyes were successfully applied to PTT without the use of dispersants. The color yields of the dyes on PTT fabric were dependent on dyeing pH as well as dyeing temperature. The optimum results were obtained at pH 5–6 and 110 °C. The dyes showed alkali-clearing property and exhibited good to excellent fastness on the PTT fabric. The COD levels of the dyeing effluent from the temporarily solubilized disperse dyes were much smaller than those from commercial disperse dye.     

Light fast monoazo dyes with an inbuilt photostabilizing unit: Synthesis and computational studies

A series of monoazo disperse dyes with a photostablilizing o-hydroxycarbonyl moiety was incorporated resulted in the enhancement of the light fastness properties on polyester and nylon substrates as compared to the dyes that do not possess the photostablilizing moiety. The geometries of the azo and the hydrazone tautomeric forms of all dyes were optimized at B3LYP/6-311+G(d) and electrophilicity index was calculated for propensity of the moiety to absorb electrons. The values of absorption and stability trend of the dyes were in good agreement with the trend of experimental light fastness values. These disperse dyes possess excellent wash fastness and moderate to good sublimation fastness on hydrophobic substrates.     

Colorimetric studies of benzoquinoline based hot brand monoazo reactive dyes and their dyeing performance on various fibers

A series of hot brand monoazo reactive dyes (9a-l) were obtained by the coupling of diazotized 1Hbenzo[ g]pyrazolo[3,4-b]quinoline-3-ylamine (5) with various cyanurated coupling components (8a-l) in good yield. Synthesized dyes were characterized by various spectroscopic techniques. Their dyeing performances as reactive dyes have been assessed on silk, wool, and cotton fabrics. The percentage dye bath exhaustion and fixation on different fibers were found to be very good. The dyed fabric showed moderate to very good light fastness and good to excellent washing and rubbing fastness properties. Spectral properties and colorimetric data of synthesized dyes have also been studied in detail.     

Dyeing of synthetic fabrics in water using azoic dyes based on boronic acid derivatives

Development of water-soluble dyes for the dyeing of different textile fabrics is essential for the textile industry due to ecological and economical reasons. In this study, a series of new azoic dyes were prepared by diazotization reaction between the phenyl boronic acid and different aniline derivatives, and their dyeing capacity in aqueous solution was evaluated. The synthesized boronic azo dyes present good water solubility and can dye polyamide (nylon), wool, silk, and cellulose acetate fabrics. The effect of factors such as concentration of dye, dyeing temperature, and pH on the level of color strength (K/S) was studied. The dyeing results showed that higher color strength K/S (about 16) and fastness properties (about 4/5) with boronic acid dyes were achieved at higher temperatures avoiding the use of surface agents, mordants, and other polluting chemical additives.     

Coloration of ultra high molecular weight polyethylene fibers using alkyl-substituted monoazo yellow and red dyes

UHMWPE fibers were dyed with yellow and red dyes having different length of alkyl substituents on monoazo chromophores. The dyeability was investigated at various conditions and fastness of the dyeings was examined. As the length of alkyl substituents increased, the dyeability toward UHMWPE fibers tends to be improved gradually up to propyl or butyl groups and then decreased for the longer alkyl substituents. Color strength of the fabrics was increased with the increase of dyeing temperature from 100 to 130 °C. From the dyeing rate, equilibrium dyeing at 130 °C was achieved at 2～3 h. The color fastnesses to washing, rubbing, and light of the dyeings were good showing higher than 4 ratings except for light fastness of the red dye.     

Polymeric dyes based on thiadiazole derivatives

A series of polymeric dyes were synthesized by free radical addition polymerization of monomeric dyes. The 2-amino-5-mercapto-1,3,4-thiadiazole was diazotized and coupled with various N-arylmaleimides to give monomeric dyes. All the polymeric dyes were characterized by elemental analysis, infrared spectroscopy, visible absorption spectroscopy, viscometry, and thermogravimetric analysis. Color and dyeing properties of the polymeric dyes were discussed by comparing them with those of the corresponding monomeric dyes. The dyeing performance of these dyes was assessed on nylon fiber. These dyes were found to give various color shades with good to very good depth and levelness on the fiber. The dyeing of the monomeric dyes showed moderate fastness to light and good to excellent fastness to washing, perspiration and sublimation and their corresponding polymeric dyes showed excellent fastness properties. The dyebath exhaustion and fixation on nylon fiber has been found to be good.     

Algal decolorization and degradation of monoazo and diazo dyes

This study is to inspect how the variation of molecular structures and functional groups present in our models, monoazo dye (Tartrazine) and diazo dye (Ponceau), affects decolorization capabilities of green algae, cyanobacteria and diatoms. The results revealed that the removal of azo dyes was rapid at the initial period of study (3 days) and became slowly with the time (6 days). The maximum decolorization was observed at 5 ppm Tartrazine with S. bijugatus (68%) and N. muscourm after 6 days incubation. The reduction of color removal appears to be related to the molecular structure of the dyes and species of algae used. The culture of the diatom Nitzschia perminuta was completely died after 2 days of incubation. Azo reductase of algae, which is responsible for degradation of azo dyes into aromatic amine by breaking the azo linkage, was estimated. IR spectra represented a new peak at 3300 cm(-1) and a reduction in the azo band at 1642-1631 cm(-1). In order to investigate the sorption behavior of algae, Langmuir equilibrium model was tested.     

Dyeing performance of the azo dyes containing trifluoromethyl group for polyester fabrics and its single crystal structure

The structures of disperse dyes and their intermolecular interactions have important impacts on dyeing and printing performances for polyester fabrics. The fluorine dyes show some unique molecular stability and photochemical properties. The dyeing property of the azo dye containing trifluoromethyl group for polyester fabrics, 4'-(N-acetoxyethyl-Nethyl)- amino-2-bromine-4-nitro-6-trifluoromethylazo- benzene (D1), was investigated and compared with the similar structure disperse dye. The results show that the high color yield and good exhaustion of the dyed PET fabrics could be obtained. The polyester fabrics dyed with D1 had excellent light fastness. Its single crystal was prepared and the supramolecular interactions were solved by X-ray diffraction. Dye D1 formed triclinic crystals in a trimeric packing mode. The C-F bond distances of CF3 are 1.2730 Å, 1.2240 Å and 1.2900 Å, respectively. The two benzene rings linked azo unit (-N=N-) are obviously twist. The dihedral angle of the two benzene rings is 50.23 o. There are six weak hydrogen bonds around trifluoromethyl group in the intramolecule and intermolecule. The excellent light stability of the dye should be attributed to its unique supramolecular structure.     

One-bath dyeing of PET/cotton blends with azohydroxypyridone disperse dyes containing a fluorosulfonyl group

Azohydroxypyridone disperse dyes containing a fluorosulfonyl group were dyed on PET/cotton blends and their dyeing and fastness properties were investigated. Specially, the azohydroxypyridone dyes containing a nitro group in place of the fluorosulfonyl group in the para position to azo group were synthesized in order to compare their dyeing and fastness properties on PET/cotton blends with those of fluorosulfonyl-substituted analogues. As these dyes can be alkali cleared in the same bath, a one-bath dyeing method was used and the results were compared with that of a conventional two-bath dyeing method. In particular, the cross-staining of cotton was studied in order to assess their suitability for the one-bath dyeing of PET/cotton blends.     

Synthesis,characterization, and properties of ethoxylated azo dyes

The nonionic surfactant properties of ethoxylated azo dyes, such as cloud point and surface tension have been investigated. The synthesized ethoxylated azo dyes could dye polyester fabric without any special pre-treatment. When the average number of ethylene oxide (EO) in the ethoxylated azo dye reached 6, its fixation could exceed 90% from the thermosol dyeing process. The average degree of condensation of ethylene glycol in the chain was interrelated with the dyeing results and did not affect on the maximum absorption wavelength (λmax) of the polyoxyethylene dye. When the average length of polyoxyethylene chain decreased, the molecular weight of dyes became smaller and the fixation of dyes was improved.     

Dyeing properties of the disperse dyes containing cyano group based on benzisothiazole for polyester fabrics under alkali condition

One step dyeing of polyethylene terephthalate (PET) fabrics combining pretreatment and dyeing under the alkali condition was developed for cleaner production. One step dyeing of PET fabrics required that the dye used has good acid and alkali stability. In this paper, dyeing properties of three azo disperse dyes containing cyano group based on benzisothiazole, 3- (4-N-ethoxyl-N-cyanoethyl -phenyldiazenyl)-5-nitro-2,1-benzisothiazole (D1), 3-(4-N-ethyl-N-cyanoethyl- phenyldiazenyl)- 5-nitro-2,1-benzisothiazole (D2), and 3-(N-benzyl-N-cyanoethyl- phenyldiazenyl)-5-nitro-2,1-benzisothiazole (D3), were investigated under alkali condition. The results showed that polyester fabrics could be well dyed with D1, D2 and D3 under the acid condition. However, D1 was decomposed while dyeing at the alkali solution. D2 and D3 had excellent color yields under the alkali condition. The acid-alkali stability and the structure change were analyzed by UV-vis spectrum and high pressure liquid chromatography (HPLC). Gaussian 09 program package was used to optimize geometry by B3LYP method and 6-31G (d) basis set. The solvation energy of D1 in water was higher than those of D2 and D3. The electron withdrawn effect of the hydroxyl affected the energy gap of HOMO and LUMO orbits. D2 and D3 showed excellent stability in the strong alkali medium. And the dyed polyester fabrics with D2 and D3 at the alkali condition also had good fastness properties.