Synthesis of temporarily solubilized reactive disperse dyes and their application to the polyester/cotton blend fabric

Five temporarily solubilized reactive disperse dyes were synthesized and characterized. They were applied to polyester/cotton blend fabric using one-bath dyeing method without dispersing agent. The dye that has azonaphthalene chromophore seemed to not only be exhausted on polyester but also react with cotton. But other dyes were selectively dyed on polyester and showed limited uptake on cotton. Good levelling as well as moderate to good colour fastness was obtained with the dyes on P/C blend fabric.     

Thiazole based disperse dyes for nylon and polyester fibers

Nine disperse dyes have been synthesized by diazotization of 2-amino-4-(p-nitrophenyl)-5-nitrothiazole and coupled to substituted N-alkylanilines. Spectral properties in the IR and visible range of the dyes obtained were investigated. The dyeing performance of these dyes was assessed on nylon and polyester fibers. These dyes were found to give reddish brown to bluish violet shades on dyeing with very good depth, brightness and levelness on nylon and polyester fibers. The dyed fibers showed fairly good light fastness, very good to excellent fastness to wash, rubbing, perspiration and excellent fastness to sublimation. The dyebath exhaustion and fixation on the fiber were found to be very good.     

Synthesis and application of phthalimide disperse dyes

Three azo dyes had been synthesized using N-propyl substituted, dibromo-substituted and dicyano-substituted phthalimides as diazo components. All of the synthesized intermediates and dyes have been characterized by MS, 1H-NMR and IR analyses. The dyeing behaviour and fastness properties of these dyes had been investigated. The absorption maxima of the dyes were observed in the range 360 to 700 nm. The results indicated that dyes caused hypsochromism effect after -Br substitution and dyes caused bathochromism effect after -CN substitution. IR spectra of hydrolyzed dye showed that C=O groups appeared under relatively mild alkaline conditions. Compared with electron density, steric hindrance effect is an more important influence factor than electron density in hydrolysis reaction process. Exhaustion of dyed polyester/elastane fabrics decreased obviously as the pH value increased. In order to ensure dyeing levelness, heating rate of prepared dyes will be strictly controlled. Due to alkali-clearable property and interaction energy of dye-fiber and dye-dye, the dyes have good colorfastness.     

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.     

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.     

Studies on antimicrobial activity for multidrug resistance strain by using phenyl pyrazolones substituted 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one derivatives in vitro condition and their dyeing performance

Heterocyclic monoazo quinazolinone based azo dyes derived by the diazotization of 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one with various phenyl pyrazolones based coupling components. All the heterocyclic azo dyes have been characterized by their percentage yield, UV-VIS spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy, and dyeing performance on silk, wool, nylon, and polyester fibers. All the dyes gave moderate to excellent fastness properties on each fiber. The main focus was to synthesize heterocyclic monoazo dyes that give good dyeing property along with pharmacological activity (anti bacterial and antifungal). Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.     

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.     

One-Bath Union Dyeing of Wool/Acrylic Blend Fabric with Cationic Reactive Dyes Based on Azobenzene

Three unreported cationic reactive dyes based on azobenzene were synthesized using a novel synthetic route. Synthesized dyestuffs containing three primary color dyes were characterized by FTIR, H-NMR, LC-MS, Element Analysis and UV-vis spectroscopic techniques. The absorption spectra of dyes were measured in three solvents with different polarities. The dyeing and color fastness properties of three cationic reactive dyes on wool, acrylic and wool/acrylic blend fabrics were determined. The optimum pH for wool and acrylic fabrics were 6 and 5, respectively. Effect of temperature, time on dyeing properties and color fastness properties on wool fabric showed the same tendency with acrylic fabric. The K/S value of wool fabric dyed with three dyes was similar to that of acrylic fabric when both fabrics were dyed simultaneously in the same dyebath using low dye concentration. Wool/acrylic blend fabric dyed with three cationic reactive dyes using onebath one-step method achieved good union dyeing property and excellent color fastness.     

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.     

Preparation of nano disperse dyes from nanoemulsions and their dyeing properties on ultramicrofiber polyester

Six nano disperse dyes were prepared using corresponding O/W nanoemulsions which were obtained with sodium laurylsulphate and caprylic triglyceride. The average particle size of the dyes prepared were in the range of 110–130 nm. Exhaust dyeing using nano dyes resulted in low exhaustion yields of 17–26 % on regular polyester fiber and 28–38 % on ultramicrofiber polyester. The observed low exhaustion yields of nano disperse dye can be explained by the solubilization of dye particles into surfactant micelles as well as the high stability of the nanoemulsions, these might reduce the capacity of dye uptake onto the fibers. However, higher K/S values of dyeings with nano dyes on ultramicrofiber sites compared to those on regular polyester sites suggested their potential to be more efficient dyes for finer denier microfiber polyesters.     

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.     

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.     

Effects of thermomigration on the washfastness of disperse dyes having different molecular size

Effects of chemical structure of disperse dyes applied to conventional and microdenier polyesters on the dyeing property and washfastness were studied. It was found that washfastness of dyed polyester fabric is closely related to the degree of thermomigration of disperse dye during heatsetting. The bulky disperse dye, which was synthesized by substituting two acetoxy groups of C.I. Disperse Red 82 with two benzoxy groups, showed almost the same amount of absorbed dye by the microdenier polyester as C.I. Disperse Red 82, but the degree of thermomigration was low and subsequent washfastness was excellent. The high grade of washfastness of the bulky disperse dye might be caused by the increased dye-fiber interaction and the reduced mobility.     

Dyeing properties of nylon,PET, and N/P mixture fabric with reactive-disperse dyes having a sulfatoethylsulfone group

The dyeing and color fastness properties of two reactive-disperse dyes containing a sulfatoethylsulfone group on nylon, PET and N/P mixture fabrics were examined. The rate of dyeing on nylon fabric was greatly dependent upon dye bath pH. The final dye uptakes at all pH, however, were as high as 97 %. Color strength of the dyed nylon fabric linearly increased up to 0.5 %owf and then slowed down over 1 %owf dyeing. Washing and rubbing fastness of the dyed nylon fabric were excellent, but grade of light fastness was moderate. Dyeability of the reactive-disperse dyes on PET fabric was not much affected by pH, and K/S values of PET fabric dyed at pH 5–8 were lower than those of nylon fabric at all pH examined. Buildup and color fastnesses properties on PET fabric showed the same tendency with nylon fabric. The rate of dyeing of the reactive-disperse dyes on nylon fabric was faster than on PET fabric when both fabrics were dyed simultaneously in the same dye pot, resulting in higher color strength of nylon than PET. The reactive-disperse dyes were found to be adequate to the one-bath, one-step dyeing of N/P mixture fabric when applied at pH 5 and 120 °C.     

One-bath one-dye class dyeing of PES/cotton blends after corona and chitosan treatment

In this work, the effects of corona discharge (CD) and chitosan treatment on the dyeability of polyester/cotton blends with direct and reactive dyes were studied. The surface chemical changes of polyester and cotton were analyzed using X-ray Photoelectron Spectroscopy (XPS). The correlation between chemical changes, wettability, and dyeability after CD and/or chitosan treatment has been established. Color intensity of both single components and PES/cotton blend increased proportionally with increasing chitosan concentration. The results obtained open the possibility for a new method for dyeing of polyester/cotton blends in a single bath using one dye-class that is commonly used for dyeing of textile material of cellulosic origin.     

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.     

Dyeing characteristics of Nylon,cotton and N/C mixture fabrics with reactive-disperse dyes containing a sulphatoethylsulphone group

The dyeing and color fastness properties of three reactive-disperse dyes containing a sulphatoethylsulphone group on Nylon, cotton and N/C mixture fabrics were examined. Reduction-clearing was more effective in removing the unfixed dyes than soaping since the reactive-disperse dye became hydrophobic during dyeing process. Nylon was dyed well with three reactive-disperse dyes at pH 5∼8 and difference in chemical structure between dyes did not affect the final color strength of the dyed Nylon fiber, but their build-up properties on Nylon were not so good. The color strength of the dyed cotton was not as high as that of Nylon. The color strength of cotton increased by lowering dyeing temperature when the reactive-disperse dyes having hydroxy group were used. Nylon absorbed more dye molecules than cotton in simultaneous dyeing, the color difference between Nylon and cotton could be reduced as the dyeing temperature decreased. N/C mixture fabric was dyed well at 60 °C with the reactive-disperse dyes having hydroxyl group when applied at pH 7 and 60 °C, and their build-up properties were good. It was also found that washing fastness and rubbing fastness of dyed Nylon, cotton and N/C fabrics with the reactive-disperse dyes were excellent, while light fastness was moderate.     

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.     

Acid dyeing properties of meta-aramid fiber pretreated with PEO45-MeDMA derived from [2-(methacryloyloxy)ethyl] trimethylammonium chloride

A diblock copolymer (PEO₄₅-MeDMA) derived from [2-(methacryloyloxy)ethyl]trimethylammonium chloride (MeDMA) was synthesized and applied to the dyeing of the meta-aramid fibers with some acid dyes. This copolymer created positive charges on meta-aramid fiber surface and a strong attraction with anionic groups of acid dyes. Meta-aramid fabric was pretreated using the synthesized copolymer and then dyed with two commercial acid dyes. The dyeability was found to be directly dependent on the concentration of PEO₄₅-MeDMA, pH in the dyebath as well as dye concentration. The color fastness of the copolymer pretreated dyed fabric was also evaluated.     

Relation between chemical structure of yellow disperse dyes and their lightfastness

Five yellow disperse dyes were synthesized and their dyeing, fastness and photodegradation behaviors were investigated. It was found that dyes derived from phenylindole and N-alkylaminobenzene showed dye uptake directly proportional to the dye concentration, but the build-up of dyes derived from carbazole and pyridone were not good. The wavelength at maximum absorption, molar extinction coefficient, and the tendency to the photodegradation were strongly dependent on the electron donating ability of the coupling component. The dye, whose coupling component was phenylindole, possessed the excellent dyeing properties and the high degree of lightfastness. UVA had an effect on the inhibition of the photodegradation especially for the easily photodegradable dyes.