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 and properties of alkali-clearable azo disperse dyes containing a carboxylic ethyl ester group

Three alkali-clearable azo disperse dyes containing a carboxylic ethyl ester group (D1-D3) were readily synthesized using three different synthetic strategies. D1 was prepared from a carboxylic acid-containing dye by esterification with ethanol. D2 was prepared from a carboxylic ester-containing dye by transesterification with ethanol. D3 was prepared from a cyano group-containing dye by alcoholysis with ethanol and water. The molecular structures of the dyes were characterized by FTIR, mass spectrometry, ¹H NMR, ¹³C NMR, and elemental analysis. The synthesized dyes and the control dyes were used to dye poly(ethylene terephthalate) fabric, and their washing and rubbing fastness properties following different after-treatment methods (reduction clearing and alkali clearing) were examined and compared. The carboxylic ethyl ester-containing disperse dyes show good alkali clearing ability on poly(ethylene terephthalate) fabric and cause fewer environmental issues due to the absence of reductants, no production of aromatic amines with high toxicity and carcinogenicity, as well as the low toxicity of the dye hydrolysate ethanol.     

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.     

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.     

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.     

High Light-Fastness Acid Dyes Synthesized from Corresponding Anthraquinone Chromophore Utilizing a Sulfonation Reaction. I. Dye Synthesis and Characterization

As the diameter of polyamide fibers decreased to finer denier, the dyeing fastness tends to be deteriorated due to the increase of their surface area, particularly both light fastness and wash fastness. In this study, three acid dyes were synthesized utilizing a sulfonation reaction starting from corresponding hydrophobic dye (for yellow and red dye) and dye intermediate containing a sulfonic acid group (for blue dye), those featured by high light fastness property. A Gaussian structural prediction model was used to determine the structure of the acid dyes prior to dye synthesis, and the optimal structures of three acid dyes were analyzed. Dye structures prepared were confirmed by ¹H-NMR, mass spectroscopy, and elemental analysis. By using a UV-vis spectrophotometer, the absorption maxima and molar extinction coefficient were also measured for three acid dyes comparing to that of the corresponding disperse dye or blue dye intermediate. Judging from spectroscopic data, the introduction of sulfonyl groups led to increase of molar extinction coefficient and a bathochromic shift.     

Synthesis and application of alkyl-substituted high chroma yellow dyes for unmodified polypropylene fiber

A series of new monoazo yellow dyes having different alkyl substituents was synthesized to dye unmodified polypropylene fiber. Color hue of the dyes exhibited light yellow with very high chroma enough to use as yellow primary color dyes. The affinity of the dyes onto unmodified polypropylene was increased with the increase of the length of alkyl substituents. Therefore, the hexyl-substituted dye having the longest alkyl group in this experiment showed very high color strength of dyeings with K/S value of over 26 at maximum absorption wavelength. The color fastnesses to washing, rubbing and light were also improved significantly for the longer alkyl substituted dyes, so that the hexyl-substituted dye exhibited a rating higher than 4∼5 for all kinds of fastnesses.     

Copper oxide-carbon nanotube (CuO/CNT) nanocomposite: Synthesis and photocatalytic dye degradation from colored textile wastewater

In this paper, CuO/CNT nanocomposite was synthesized and its photocatalytic dye degradation ability for colored textile wastewater was studied. The characteristics of the nanocomposite were investigated by XRD, SEM and FTIR. The photodegradation of Direct Red 31 (DR31) and Reactive Red 120 (RR120) by CuO/CNT in presence of H₂O₂ was investigated. Photocatalytic dye degradation was determined by UV-vis spectrophotometer. Effects of catalyst dosage, initial dye concentration and salt on photodegradation performance were studied. The photocatalytic dye degradation ability of pure CuO and CuO/CNT nanocomposite is 78 % and 89 % for DR31 and 70 % and 87 % for RR120, respectively. The results showed that CNT increased the photocatalytic activity of CuO. The presence of salt decreases dye degradation efficiency. The dye degradation kinetics by nanocomposite followed first-order kinetic model. The reaction rate at 0.005 g catalyst was 0.0137 and 0.0105 min^-1 for DR31 and RR120, respectively. It was found that the CuO/CNT nanocomposite as a photocatalyst could be used to degrade dyes from colored wastewater.     

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 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: Synthesis and characterization

Two novel cationic softener containing mono-s-chloro triazinyl reactive dyes together with their analogues were designed. The dyes were synthesized via reacting an N,N-dimethyldodecylamine with p-nitrobenzyl bromide. The resultant was reduced using stannous chloride and hydrochloric acid to produce the primary amine. The quaternary ammonium salt containing primary amine was then diazotized to produce diazonium salt part of azo dye. The diazonium salt was then coupled to H-acid/J-acid reacted with cyanuric chloride and sulfanilic acid. The analogue dyes were prepared via the same route without quaternary ammonium salt making stage. The chemical structures of the novel dyes were characterized by FTIR, ¹H-NMR, and elemental analysis. The spectroscopic properties of the dyes were determined in terms of λ _max and ? _max in aqueous solution.     

Binary catalyst system dye degradation using photocatalysis

In this paper, soy meal hull activated carbon (SMHAC) and titania nanoparticle (TiO₂) were used as catalysts to degrade dyes. Activated carbon was prepared using soy meal hull. Degradation of dyes using single and binary catalyst systems was studied. Textile dyes were used as model pollutants. Photocatalytic dye degradation and mineralization were studied using UV-Vis spectrophotometer and ion chromatography (IC). The effects of pH, initial dye concentration, and salt on dye degradation were investigated. Dye solutions were decolorized completely (100 %). The presence of salts decreased dye degradation rate. Degradation of dyes followed first order kinetics model. Formate, acetate, and oxalate were detected as dominant aliphatic intermediates during dye degradation process. Nitrate, sulfate, and chloride anions were detected as dye mineralization products.     

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.     

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.     

Acrylamide assisted photoinitiator-free photografting of acrylamido dyes onto wool

Upon UV irradiation wool fabrics can be photografted with photoactive acrylamido dyes at room temperature without photoinitiaors, which is eco-friendly coloration process compared with conventional adsorption-based dyeing. Acrylamide addition as a comonomer can improve the photografting probably by reducing the steric hindrance between the bulky dyes during the photocopolymerization. Even without photointiators and neutral salts, the optimal K/S values of the photografted wool reached upto 18.7 and 18.5 for Reactive Red 84 and Yellow 39 dyes respectively. The optimal UV-grafting coloration can be achieved when a UV energy of 25 J/cm² was irradiated on the padded fabrics with 6.3 %owf dye containing 0.65 mole ratio of acrylamide to the dyes. Furthermore, the color fastness of the grafted fabrics was as good as those of conventionally dyed fabrics due to the copolymerization of dyes and comonomers.     

Application of liquid organic salt to cotton dyeing process with reactive dyes

Reactive dyes are used widely in cotton dyeing process. Reactive dyeing uses high amounts of inorganic salts to accelerate dye exhaustion. These salts are then discharged to the effluent, leading to serious environmental problems. Biodegradable organic salts can alternatively be used in the dyeing process. In this paper, a new liquid organic salt was synthesized by acid-base neutralization, which was used to replace inorganic salts in reactive dyeing. Dye exhaustion in organic salt dyeing was similar to the values in conventional dyeing. However, dye fixations were slightly lower in organic salt dyeing than in conventional dyeing. The washing fastness of dyed fabrics with organic salt was excellent. Experimental results showed that dye exhaustion reached the maximum value when the concentration range of organic salt was from 20 g/l to 40 g/l. In addition, the optimal alkali concentration in organic salt dyeing was found to be about 30 g/l. These parameters suggested organic salt could replace inorganic salt in reactive dyeing process.     

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.     

Dispersant-free dyeing of polyester with temporarily solubilized azo disperse dyes from indole derivatives

Temporarily solubilized azo disperse dyes based on 1,2-substituted indoles were synthesized and characterized. Dispersant-free dyeing of polyester by using the synthesized dyes has been investigated. The colour yields of the dyes on the polyester fabric were found to be highly dependent on the dyeing pH, optimum results being obtained at pH 5. The dyes exhibited good to excellent fastness properties on polyester while lightfastness was moderate.     

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.     

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.