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.     

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.     

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.     

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.     

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.     

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.     

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.     

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.     

Coloration of poly(lactic acid) with disperse dyes. 1. Comparison to poly(ethylene terephthalate) of dyeability, shade and fastness

The dyeability of poly(lactic acid) [PLA] with a range of commercial disperse dye was examined and compared to that of poly(ethylene terephthalate) [PET] in addition to the colour and fastness of the resultant dyeings. A screening exercise in which twenty dyes of differing energy types and chemical classes were applied to PLA revealed a substantial variation between the dyes in terms of dye uptake (12–88 % at 4 %o.w.f.). Nine dyes exhausted above 70 % and were selected for further study, which involved comparison of shade and fastness of PLA dyeings with those of the corresponding PET dyeings. Differences in shade depended on hue while wet fastness of each of the PLA dyeings was either the same or 0.5–1.0 point lower than its PET counterpart. In all but one case, dye photostability in PLA was found to be very similar to that in PET. Dye build-up profiles on PLA were also investigated and from these results mixtures of compatible dyes identified.     

Salt free reactive dyeing of cationized cotton

In this study 3-chloro-2-hydroxypropyltrimethylammonium chloride was used as a cationic agent to cationize cotton fabric by a pad-batch process. The cationized cotton samples were dyed with different reactive dyes containing various reactive groups. The dyeability of the cationized cotton samples with reactive dyes without salt was significantly improved due to an increase in the ionic attraction between the dye and cationized cotton. The results showed that the wash and dry rubbing fastness of the cationized cotton dyed with different reactive dyes are similar to those of the untreated cotton. However, the light fastness of some of the cationized fabric samples was improved.     

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.     

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.     

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.     

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.     

Dyeing and fastness properties of vat dyes on meta-aramid woven fabric

meta-Aramid fibers have an excellent heat-resistant property and are widely used for protective clothings such as fire-fighter suit and racing suit. They can also be used as military uniforms such as flight suit or army uniform. Vat dyes are specially used for military uniforms owing to outstanding fastness properties, earth tone shade, and near infrared (NIR) camouflage. In this study, 100 % meta-aramid woven fabric was dyed with three vat dyes using an exhaustion method and their dyeing and fastness properties were investigated. Color yields of the vat dyes on the meta-aramid fabric were found to be dependent upon dyeing temperature, liquor ratio, amount of reducing agent, and amount of salt. Dyeing behavior of the vat dye on the meta-aramid fiber was very similar to that on cellulose fibers. It was found that the meta-aramid fabric dyed with 1% owf of C.I. Vat Green 1 satisfied the tolerance of the reflectance spectrum of forest green color in the Korean military standard. Thermal stability and mechanical property of the meta-aramid fabric did not significantly affected by the vat dyeing process. Wash and perspiration fastness was generally good but rubbing and light fastness was unsatisfied.     

UV-induced coloration of cotton fabrics by photografting of acrylamido dyes using acrylamide as a comonomer

Formulations of acrylamido dyes containing comonomers can be photografted onto cotton fabric upon UV irradiation at room temperature without neutral salts, which makes it a novel coloration process of excellent environmental friendliness. The photografting of the dyes can be assisted by the copolymerization of the acrylamide comonomer which may reduce the steric hindrance of the bulky dyes. About 90 % of the dyes and 94 % of the acrylamide are photopolymerized in the solution and the degree of polymerization is estimated to be 13.2 according to ¹H-NMR and MALDI-TOF mass analyses. The optimal K/S values of the grafted cotton fabrics showed 13.3 and 12.3 for red and yellow 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 a formulation of 0.65 mole ratio of acrylamide to the dyes, 7 wt% acetophenone photoinitiator (Irgacure 2959) based on the dye weight under pH 6. Furthermore, the color fastness properties of the grafted fabric were superior to those of conventional reactive dyeing of the dyes due to higher molecular weight of the polymerized dyes.     

UV protective properties of cotton fabric treated with plasma,UV absorber,and reactive dye

The influence of water vapor plasma on the adsorption of UV absorber during the reactive dyeing of bleached and mercerized cotton fabric was examined. Exhaust dyeing of untreated and plasma-treated cotton was performed using a reactive dye Cibarcon Deep Red S-B and a commercial UV absorber Tinofast CEL. Blank dyeing was performed as a control experiment. Fourier transform infrared spectroscopy (FTIR) was used to identify the presence of the UV absorber on the cotton fabric, whereas scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS) were used to analyze surface changes of untreated and plasma-treated dyed samples. The CIELAB color values and ultraviolet protection factor (UPF) of the samples were determined spectrophotometrically. Wash and light fastness of samples was performed also. The results reveal that the UPF of cotton increases after UV absorber treatment and that plasma treatment increases the adsorption of UV absorber during dyeing process, especially at higher dye concentrations. The enhanced adsorption of UV absorber onto plasma-treated cotton is the result of the increased concentration of oxygen containing functional groups on the cotton surface after plasma treatment, confirmed by XPS. The UPF of plasma-treated cotton samples is decreased after washing and increased after exposure to xenon light.     

The effect of carbon black nanoparticles on some properties of air plasma printed cotton/polyamide 6 fabrics

In this study, cotton/nylon blended fabrics were treated with atmospheric air plasma at various times (30–60 s) and were subsequently printed with pastes containing carbon black nanoparticles. Properties of plasma treated fabrics such as visible-near infrared (Vis-NIR) reflectance, water contact angle, air permeability, and color fastness were measured. It was shown that increasing plasma treatment time decreases reflection level of treated fabrics in Vis-NIR region. Plasma treatment also enhanced the hydrophobicity of cotton/nylon fabrics observed by an increase in water contact angle. Plasma treated samples for 60 s demonstrated lower air permeability than those treated for 30 s. Furthermore, printed samples possessed acceptable levels of fastness against washing, light and crocking.     

Synthesis of hydrophobic anthraquinoid magenta dyes having linear alkyl substituents

A new series of magenta dyes having different length of alkyl substituents was synthesized to dye unmodified polypropylene (PP) and ultra-high molecular weight polyethylene (UHMWPE) fiber. It could be concluded that the affinity of the dyes onto unmodified PP and UHMWPE fibers was increased with the increase of the length of alkyl substituents. The optimum length of alkyl group was determined as the longest dodecyl-substituted dye in this study. Their absorption spectra appeared almost the same at visible range, which meant that the length of alkyl substituents did not affect the color appearance of the dyes. The color fastness properties of the dyeings to washing, rubbing and light were good enough for commercialization.     

A novel approach for estimating the relation betweenK/S value and dye uptake in reactive dyeing of cotton fabrics

This paper focuses on the application of a novel mathematical limit approach derived forK/S values in reactive dyeing of cotton fabrics. The relation obtained from Kubelka-Munk equation is used because the Kubelka-Munk equation is the basic relationship among fabric reflectance, fabric dye content and dyestuff characteristics. The limit approach derived in a former paper is applied to the laboratory dyeings and the dyeing behavior of some reactive dyes on cotton knitted fabric has been obtained. The results of the laboratory experiments are discussed using the new mathematical approach. When the actualK/S values obtained from the dyeings and the calculatedK/S values derived by the limit approach are considered independently, it is observed that the limit relation is valid for low dye concentration applications. When theK/S values are calculated taking theK/S value of the initial dyeing concentration (0.1 % owf) as the starting concentration by applying the result of the derived limit approach, the calculatedK/S values fit with the ones obtained in actual dyeings. It is concluded that the novel approach presented in the paper can be used in calculating theK/S values when the initial dyeings at low dye concentrations are carefully carried out.