Dyeing properties of novel azo disperse dyes derived from phthalimide and color fastness on poly(lactic acid) fiber

The coloration of poly(lactic acid) (PLA) fiber with 18 carbocyclic monoazo disperse dyes bearing a hydrolyzable phthalimide ring fused to the aromatic ring of their diazo components has been investigated. The phthalimidyl nitrogen atom was substituted with either a n-butyl, sec-butyl, or isopropyl group, while the adjoining phenyl ring bore a substitution pattern typical of commercial colorants. There was a broad correlation between percentage dye exhaustion onto PLA and that onto polyester (PET) fiber, although significant differences in certain instances were apparent with no clear trends regarding dye structure. Attempts to explain the observed percentage exhaustion values by mapping them to calculated partition coefficient or solubility parameter values were unsuccessful. Wash fastness was relatively good compared to that of some conventional disperse dyes applied to PLA. As was found to be the case with PET, the wash fastness of dyes on PLA tended to be highest when their diazo ring was substituted with electron acceptors.     

Coloration of poly(lactic acid) with disperse dyes. II. Dyeing characteristics and color fastness

In Part 1 of this study, the dyeability, color shade, wash, light fastness and compatibility of homogeneous disperse dyes on PLA fabric and PET fabric were reported. The present paper (Part 2) focuses on the application of commercial disperse dyes to PLA fabric. Specific areas of investigation are the coloration properties of dyes originally intended for the production of high lightfastness polyester fabrics or for application to cellulose diacetate. The compatibility of the eight members of the dye set was investigated. In terms of lightfastness, the ratings were higher than that of conventional disperse dyes. In addition, the use of dye combinations to achieve synergistic uptake on PLA was explored leading to the pronounced synergism with a mixture of CI Disperse Blue 374 and 284.     

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.     

Dyeing and fastness properties of natural dyes extracted from eucalyptus leaves using padding techniques

A natural dye extracted from eucalyptus leaves was applied to a silk and wool fabric by the use of two padding techniques, namely the pad-batch and pad-dry techniques under different conditions. Silk and wool fabrics dyed in a solution composed of eucalyptus extract from leaves showed a shade of pale yellow to brown. The exception was when the fabric was dyed with ferrous mordant, resulting in a shade of dark grayish-brown. The fastness properties ranged from good to excellent, while light fastness was fair to good.     

Dyeing and fastness properties of vat dyes on a novel regenerated cellulosic fiber

enVix is a novel regenerated cellulosic fiber, which is prepared from cellulose diacetate fiber using environmentally friendly manufacturing process. Vat dyeing properties of the enVix were investigated and compared with those of regular viscose rayon. The enVix exhibited better dyeability than viscose rayon. The colour yields of vat dyes on the enVix were found to be dependent on dyeing temperature as well as the amount of levelling agent and salt. Good build-up and good to excellent fastness properties were obtained on the enVix fabric.     

Dyeing and fastness properties of a reactive disperse dye on PET, nylon, silk and N/P fabrics

Dyeing and color fastness properties of a reactive disperse dye containing an acetoxyethylsulphone group on PET, Nylon, silk and N/P fabrics were examined. The reactive disperse dye exhibited almost the same dyeing properties on PET fabric as a conventional disperse dye except the level of dye uptake. The most appropriate pH and dyeing temperature for the dyeing of Nylon fabric were 7 and 100°C respectively. The build-up on Nylon fabric was good and various color fastnesses were good to excellent due to the formation of the covalent bond. Application of the reactive disperse dye on silk fabric at pH 9 and 80°C yielded optimum color strength. The rate of dyeing on Nylon fabric was faster than that on PET fabric when both fabrics were dyed simultaneously in a dye bath, accordingly color strength of the dyed Nylon was higher. The reactive disperse dye can be applied for one-step and one-bath dyeing of N/P mixture fabric with good color fastness.     

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.     

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.     

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 properties and colour fastness of wool dyed with indicaxanthin natural dye

This research work involves the dyeing of wool with indicaxanthin, a natural dye extracted from fruits of Opuntia ficus-indica. The optimal conditions for dye extraction were to mix 50 g of Juice from cactus pears with 100 mL of 80% aqueous ethanol as solvent for dye extraction. Liquid chromatography was applied for the separation. Two main dyes were obtained, which were identified as indicaxanthin (75 mg per 50 g) and betanin (5 mg per 50 g). The effect of dye bath pH, salt concentration, dyeing time and temperature were studied. The optimal conditions for wool dyeing with indicaxanthin dye were carried out at 70 °C for 90 min with the pre-treatment of various metal salts as mordant. The colour yields of the dye on the wool were found to be highly dependent of the pH, optimum results being obtained at pH 4. The K/S of wool increased in the order of the dyeing using KAl (SO₄)₂ > MnSO₄ > CoSO₄ > FeSO₄ > none > ZnSO₄ > CuSO₄. Un-mordanted samples have good properties of water and washing fastness. Mordants KAl (SO₄)₂ and CoSO₄ were found to give good light fastness (rating 5).     

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.     

Synthesis and spectral properties of phthalimide based alkali-clearable azo disperse dyes

The synthesis of a series of phthalimide based azo disperse dyes and their spectral properties were investigated. The azo dyes containing phthalimide and N-methyl phthalimide structure in diazo component were synthesized in order to compare their spectral properties. The synthesized dyes developed the color of yellow to violet and the N-substitution of the phthalimide gave a bathochromic effect on the color change. Most of the synthesized dyes exhibit negative solvatochromism so that the absorption band of dyes moves toward shorter wavelengths as the polarity of the solvent increases. In the case of halochromic effect, the bathochromic shift decreased steadily with the general electron donating capacity of the substituents in the coupling component, and became negative especially when more powerful electron donating groups are present in the coupling components ring.     

Dyeing behavior of chemically modified poly(1,4-phenylene sulfide) fiber towards disperse,anionic, and cationic dyes

Poly(1,4-phenylene sulfide) (PPS) exhibits good dimensional stability and flame retardant characteristics but its commercial development as fibers is highly limited due to lesser dyeing and finishing characteristics. Hence in the present study, we focused on the anionic and cationic modifications of PPS to enhance its dyeing ability towards disperse, cationic, and anionic dyes. Novel sulfonation and chloromethylation-quaternization of PPS fiber were carried out to achieve an industrially viable dyeing process methodology. The chemically modified PPS fiber is dyed with disperse, cationic, and anionic dyes, and the dyeing adsorption efficiency is quantitatively studied using a dye-o-meter equipped with UV-visible absorption spectroscope. The ideal parameters for dye adsorption were determined as a function of dyeing time, material-toliquor ratio, dyeing temperature, carrier concentration, sulfonation, and chloromethylation. The fastness properties of the dyed fabrics were also studied. Overall, with a maximum dye uptake of 99 % and 90 % achieved for sulfonated PPS and quaternized PPS respectively, the optimized conditions can be readily scaled-up to the commercial dyeing of PPS fiber with disperse, anionic, and cationic dyes.     

Effects of alkali pre-treatment on dye exhaustion, color values, color fastness, tensile and surface properties of lyocell yarns

The effects of alkali (aqueous NaOH and KOH solutions) pre-treatment on dye exhaustion, color values, color fastness, tensile and surface properties of lyocell yarns were investigated. Dye exhaustion and color yield of lyocell yarns increased by increasing alkali concentrations. The lyocell yarns showed weight loss due to the decrease in carboxyl groups during alkali pre-treatment. The tensile strengths of lyocell yarns decreased with the increase of alkali concentrations because of the decrement of yarn diameter by weight loss the open twist spirals, and the increased volume of lyocell yarns after alkali pre-treatment. The washing and perspiration fastness results of untreated lyocell yarns were better than alkali pre-treated lyocell yarns, while the light fastness results of untreated and alkali pre-treated samples were similar.     

Antibacterial properties and color fastness of silk fabric dyed with turmeric extract

The use of non-toxic and eco-friendly natural dyes on textiles has received much attention due to the increased environmental awareness in order to avoid some hazardous synthetic dyes. In the present study, an eco-friendly approach was developed to impart color and antibacterial properties to silk fabrics dyed with turmeric extract as a non-toxic natural colorant. The natural colorant was extracted from Curcuma Longa rhizome. Copper sulfate, ferrous sulfate and potassium aluminium sulfate were applied in a pre-metallization process as mordanting agents. Antibacterial properties of treated fabrics were evaluated against common pathogenic bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The effects of dye concentration and mordant types on the obtained color hues, antibacterial efficiency and color fastness of the fabrics were investigated. The results indicated that mordanted and dyed fabrics possessed desirable antibacterial properties. Complete antibacterial activity of the treated fabrics was obtained with 3 %owf (on weight of the fabric) copper sulfate. It was also shown that increasing the dye concentration could lead to a more efficient antibacterial activity on the mordanted dyed fabrics. An optimum level of the antibacterial activity was observed in the sample treated with 30 %owf of turmeric. Furthermore, the results of CIE L*, a*, b* values, FTIR, washing, light and rubbing fastnesses of the dyed fabrics were reported. The mordanted dyed silk fabrics exhibited desirable color fastness properties. These studies proved a direct relationship between the degree of antibacterial activity of the fabrics treated with turmeric and the metals ion concentration.     

Dyeing properties and color fastness of 100% <Emphasis Type="Italic">meta</Emphasis>-aramid fiber

Dyeing characteristics and fastness of 100 % m-aramid fiber with some commercial dyes were investigated on various dyeing conditions, such as using a swelling agent and electrolyte as auxiliaries. Among commercial dyes used, the basic dyes showed comparatively higher exhaustion yield comparing to those of disperse dyes and acid dyes. Under acidic conditions in the range pH 3 to 5, preferably between pH 3 and 4, the stability of cationic dyes could be enhanced leading to higher adsorption. Dye exhaustions of trichromatic dyes were increased proportionally to concentration of swelling agents ranging from 1 to 4 g/l. The addition of electrolyte provided increased K/S values after washing process compared with those of blank dyeings, where the greatest effect was observed with NaNO₃.     

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.     

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.     

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.     

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.