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 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.     

Azocalix[4]pyrrole dyes: Application in dyeing of fibers and their antimicrobial activity

The dyeing performance of the azocalix[4]pyrrole dyes on fibers like nylon, wool, acrylic, and silk have been determined. Their fastness properties towards light, water, washing, and acid-alkali perspiration have been studied. The position of color in CIELAB coordinates (L*, a*, b*, H, and C*) was assessed. The azocalix[4]pyrrole demonstrated good antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Aspergillus niger. These super molecules exhibit bright shades on fabric with very good fastness properties.     

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.     

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.     

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 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.     

Study of analytical methods for quantifying unfixed form of bifunctional reactive dyes used in dyeing cellulosic fibers (cotton)

The objective of the present study was to examine the reliability and compatibility of three methods for quantifying the unfixed form of heterobifunctional reactive dye type monochlorotriazine/β-sulfatoethylsulfone used in dyeing cellulosic fibers (cotton). The first method is based on spectrophotometric analysis by measuring the absorbance of residual dyebath (after dyeing process) and residual soaping bath (after washing-off phase), the second one is based on colorimetric analysis by measuring the reflectance of dyed fabric, and the third on high-performance liquid chromatography (HPLC) technique. The purpose of the latter is to identify and quantify the hydrolyzed and inactive forms of dye in residual soaping bath. The calculated unfixed dye rates unequivocally prove the reliability and compatibility of these methods. According to the availability of the required laboratory instruments, we can select the most suitable method in every case, though the tests proved that the HPLC technique is most efficient.     

Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics

A series of new azomethine dyes based on pyrazolone system have been synthesized via different routes. The solvatochromism for the dyes was evaluated with respect to spectroscopic properties in various solvents. The dyes were applied as disperse dyes on polyester fabrics and gave shade poor to excellent light fastness, washing, perspiration, sublimation, and rubbing fastness properties. Also the position of color in CIELAB coordinates (L*, a*, b*) and K/S value were investigated.     

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

Seven new upper rim functionalized azocalix[4]resorcinarene dyes have been synthesized by coupling calix[4]resorcinarene with different diazo compounds of p-chloroaniline, p-nitroaniline, p-toludine, p-anisidine, p-aminobenzoic acid, o-aminophenol, and aniline. The characterization of these dyes has been carried out by elemental analysis, FT-IR, ¹H- and ¹³C-NMR. Effect of solvents of varying dielectric constants on the absorption spectra of substituted and unsubstituted azocalix[4]resorcinarene dyes have been examined by UV-vis spectrophotometer. These azocalix[4]resorcinarene dyes have also been used for dyeing textile fibers like cotton, silk, and wool. Their dyeing and fastness properties have also been discussed.     

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.     

Synthesis of cationized anthraquinone dyes and their dyeing properties for meta-aramid fiber

Due to compact structure of meta-aramid fiber caused by the intermolecular hydrogen bondings of amide groups, the degree of crystallinity increased, thus its poor dyeing properties arises. Among commercial dyes used in many previous researches, the basic dyes showed comparatively higher exhaustion yields as comparing to those of disperse dyes and acid dyes. The anthraquinone moiety was adopted for good performances of light fastness on meta-aramid fiber. In this study, eight of anthraquinone dye was synthesized. The three of them were obtained from chloro-anthraquinone, by Ullmann reactions with the corresponding heterocylic residues such as morpholine and one of them was obtained from lueco quinizarine by condensation with the corresponding heterocylic residues. The others were prepared by quaternization from dyes above. The synthesized disperse and cationic dyes were dyed on meta-aramid fibers and investigated for their build-up dyeing properties and wash fastness.     

Novel cationic softener containing MCT reactive dyes for cotton: Simultaneous dyeing and functional finishing

The cationic softeners containing MCT (monochloro-s-triazinyl) reactive dyes were employed on the dyeing of cotton fabrics. The substantivity, exhaustion, and fixation of the dyes were investigated. It was found that these functional dyes could be effectively introduced to cotton fibers to achieve simultaneous coloration and functional finishing effects. All the dyed fabrics exhibited softening efficacy. The dyes offered excellent washing fastness on cotton substrate. Light fastnesses of the dyes on the substrate were poor.     

Adsorption and dyeing characteristics of reactive dyes onto cotton fiber in nonionic Triton X-100 reverse micelles

The nonionic reverse micelles used for dyeing cotton fiber were prepared with a non-ionic surfactant Triton X-100 (TX-100) by injecting small amount of reactive dye aqueous solution. The adsorption capacity of three water-soluble anionic azo dyes including Reactive Blue 222, Reactive Red 195 and Reactive Yellow 145 onto cotton fiber was investigated. The Langmuir and Freundlich isothermals were employed to model the adsorption data. In addition, the color strength and fixation rate of cotton fabrics dyed in the reverse micelles and bulk water were examined and compared. The salt and alkali as influencing factors were also discussed. The FT-IR spectra were employed to study the polarity of water added in reverse micelles. The results indicated that the adsorption of the dyes onto cotton showed better agreement with Langmuir model. The adsorption process was monolayer adsorption. Reactive Yellow 145 with lower negative charge and higher hydrophilicity exhibited the higher adsorption capacity. The fixation percentage and color strength of the cotton fiber dyed in TX-100 reverse micelles was higher than those in bulk water. The polarity of water in TX-100 reverse micelles was lower than that in bulk water.     

Study on differences of reaction behavior of phenolic hydroxyl groups with vinyl sulfone reactive dyes and monochlorotriazine reactive dyes

Using p-methylphenol as a model compound for phenolic hydroxyl groups on silk fibroin, the reaction kinetics of two typical of reactive dyes including vinyl sulfone reactive dyes and monochlorotriazine reactive dyes with phenolic hydroxyl groups were studied by reverse phase ion-pair high-performance liquid chromatography. The results showed that, the reaction rates of monochlorotriazine reactive dyes with phenolic hydroxyl groups were by far faster than those of vinyl sulfone reactive dyes, attributed to the stability of resultants from the former. The optimum reaction conditions for phenolic hydroxyl groups with vinyl sulfone reactive dyes and monochlorotriazine reactive dyes were at 50–70 °C and pH=8–9 for the former, and at 85–95 °C and pH=8–9 for the latter. The methods and results in this paper would help to deeply study the reaction mechanisms of reactive dyes with silk fibroin.     

A study of reusing vinyl sulfone based reactive dye for dyeing cotton fiber

Reactive dye is a popular dye for dyeing cotton fiber due to its very good color fastness which is explained by the formation of covalent bond between dye and fiber. In this study, practicality of reuse of reactive dye by compensating for the hydrolyzed part of the dye solution is examined. A monofunctional dye (vinyl sulfone type) was used and it was found that dyeing cotton fiber with reused dyebath is possible. Since bifunctional dye can improve the chance of dye-fiber bond formation, vinyl sulfone based bifunctional reactive dyes were also selected in this study. Three types of bifunctional dyes were used and they basically share the same vinyl sulfone group; other reactive groups are monochlorotriazine, dichlorotriazine and vinyl sulfone. Such dyes were chosen in order to compare their respective efficiencies under the effect of one common reactive group. The aim of this study was to compare the effect of hydrolyzed and unhydrolyzed proportions of mono-and bifunctional reactive dyes on cotton fiber and study the possibility and efficiency of the two different reuse dyebath systems.     

Basic study on the two-tone color dyeing of PET and PVC wig fibers by carrier dyeing method

PET or PVC wig fibers are usually colored by the dope dyeing method in which the pigment or color master batch is mixed before the spinning process. However, the colored fibers need to be dyed again to obtain a two-tone color along the longitudinal fiber direction. In this study, PET and PVC fibers were dyed by the carrier dyeing method using a disperse dye, and the dyeing behavior was investigated. The fiber was dyed at various carrier and dye concentrations. The dye uptake increased with increasing carrier concentration or dye concentration. The saturation of the dye uptake was observed in each case. No change of the glass transition temperature (T_g) was observed in the 1st run of the DSC thermogram, however, a decrease in the value of T_g was observed in the 2nd run performed after the 1st run sample was quenched and re-measured. The reduction in the value of T_g implies that the carrier acted as a plasticizer in the fiber and enhanced the segmental mobility of the polymer chains. The dyeing temperature and carrier concentration were varied and the diffusion coefficients of the dye and activation energy were measured. The activation energy was increased at a higher carrier concentration, because the carrier acted as a plasticizer and lowered the energy barrier to the penetration of the dye molecule into the polymer chains.     

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.     

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.     

Study on the dyeing properties of hemicyanine dyes. I. Acrylic fabrics

Three hemicyanine dyes were employed in dyeing acrylic fabrics following traditional cationic dyeing procedures. The influence of the substituting groups of the dye molecule on the sorption rate and sorption isotherms was analyzed. The results showed that those dyed acrylic fabrics using hemicyanine dyes had obvious fluorescent effect in the spectra range 550–750 nm. In addition, according to the EN-471 standard (2003), the chromaticity of dyed acrylic fabric was calculated to evaluate whether hemicyanine dye could meet the requirements of the fluorescent dye for high visibility warning clothing.