Solubility of Two Disperse Dyes Derived from <Emphasis Type="Italic">N</Emphasis>-Alkyl and <Emphasis Type="Italic">N</Emphasis>-Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

The solubility of naphthalimide-based monoazo dyes containing N-ethyl and N-ethanoic acid groups was investigated in the presence of a conventional monomeric counterpart (DTAB) and two cationic gemini surfactants (12-4-12 or 14-4-14) individually. The effective parameters on dye solubility such as temperature, time and concentration of surfactants were investigated by UV–Visible spectrophotometry. The results demonstrate that the solubility of both dyes was considerably increased at concentrations above the surfactant CMC. The wavelength for the maximum absorbance of dyes in the aqueous solution shifts toward longer wavelengths with changes in the concentration of the cationic surfactants. A kinetic study of solubilization of dyes in cationic surfactants solution showed that the rate of solubilization follows the pseudo-first-order reactions. Rates of solubilization were in the range of 0.5 × 10⁻³ to 6.8 × 10⁻³ min⁻¹ for both dyes. The disperse dye containing a carboxylic acid group (dye 2) has a higher solubility rate than the dye containing an alkyl group (dye 1). The type of surfactant has a very low effect on adsorption of dye 1 onto the polyester fibers, whereas changing the surfactant type from DTAB to 12-4-12 or 14-4-14 causes adsorption of dye 2 on polyester to decrease.     

A New Method for Clearing Dyed Polyester Fabrics by Gemini Cationic Surfactants

In the study, a new treatment with cationic surfactants was proposed to remove deposited disperse dyes from polyester fabrics as an alternative to the traditional reduction clearing process. For this purpose, dodecyltrimethyl ammonium bromide and two gemini cationic surfactants (12-4-12 and 14-4-14) were investigated and the optimum operating conditions were obtained using a central composite design. Findings indicated that gemini cationic surfactants can be considered as the best candidates to remove deposited disperse dyes from polyester fabrics. This was confirmed by the results of the scanning electron microscope images, fastness properties and spectrophotometry.     

Electrostatic self‐assembly dyeing of cotton fabrics

A new approach to the dyeing of cotton fabrics using an electrostatic self‐assembly method was evaluated. Cotton fabrics were pretreated with 2,3‐epoxypropyltrimethylammonuium chloride and cationic charges were produced on the fabric surfaces. For the dyeing of cotton fabric, reactive and acid dyes were used. Oppositely charged anionic reactive/acid dyes and cationic poly(diallyldimethylammonium chloride) were alternately deposited on the surface of cationised cotton fabrics. Ten multilayer films of dye/poly(diallyldimethylammonium chloride) were deposited on the cotton fabric surfaces using a padder. The build‐up of the multilayer films and the level of colour strength (K/S) achieved are discussed. Samples of cotton fabrics were also dyed with the same dyes, but using the exhaust method, and both types of dyed samples were compared. The washing, rubbing and light fastness properties were evaluated for the dyed fabrics.     

Novel hydrolysable azo disperse dyes based on N‐ester‐1,8‐naphthalimide: dyeing of polyester–cotton blends

The dyeing of polyester–cotton blends with new alkali‐hydrolysable azo disperse dyes based on N‐ester‐1,8‐naphthalimide was investigated. Polyester–cotton blend fabrics were dyed using both one‐ and two‐bath methods. Dyes 3 and 4 offered lower colour yield on polyester using the one‐bath method. For the rest of the dyes, employing either the one‐ or two‐bath method resulted in a similar colour yield on polyester fabric. The results for fastness properties and colour yield of the dyeings showed that the dyes were suitable for dyeing polyester–cotton blends using the one‐bath method. The kinetic study of hydrolysis of the dyes in alkali media obeyed the pseudo first‐order reaction rate.     

Improvement of the dyeing and fastness properties of a naphthalimide fluorescent dye using poly(amidoamine) dendrimer

In this study, 4‐amino‐9‐methoxypropylnaphthalimide fluorescent dye (dye 1 ) was reacted with poly(amidoamine) dendrimer G = ?0.5 to prepare a naphthalimide–dendrimer hybrid dye (dye 2 ). The chemical structures of the synthesised dyes were confirmed by elemental analysis, Fourier transform infrared spectroscopy, ¹H nuclear magnetic resonance spectroscopy, and ultraviolet‐visible spectroscopy. The solvatochromism of the dyes was evaluated in various solvents with respect to visible absorption properties, and positive solvatochromism was observed by solvent polarity change from chloroform to ethanol. The dyeing ability of the synthesised dyes was investigated by their application onto nylon fabric, and nylon substrates dyed with dye 2 exhibited marked enhancement both in terms of colour strength and general fastness properties. The results of this study clearly demonstrated the high potential and performance of dye 2 as a novel promising fluorescent dye as compared with dye 1 . Overall, it was inferred that the modification of the naphthalimide fluorescent dye with poly(amidoamine) denderimer could markedly improve the dyeing and fastness properties of the naphthalimide fluorescent dye on nylon fabrics.     

Synthesis of temporarily solubilised azo disperse dyes containing a β‐sulphatoethylsulphonyl group and dispersant‐free dyeing of polyethylene terephthalate fabric

Disperse dyes containing a β‐sulphatoethylsulphonyl group have temporary solubility and can be applied for dispersant‐free dyeing of hydrophobic fibre. Six novel temporarily solubilised azo disperse dyes having a β‐sulphatoethylsulphonyl group in their structures were synthesised, and their dyeing properties on polyester were investigated. As a dye intermediate, a diazo component having dibromo groups was prepared, and 4‐diethylamino‐4′‐(2‐sulphatoethylsulphonyl‐4,6‐dibromo)azobenzene dyes were prepared by a diazo‐coupling reaction. Then, the dyes containing dicyano groups were prepared by cyanation of corresponding dyes with dibromo groups. The absorption maxima of the dyes were affected by the substituents in the diazo and coupling component rings and varied from 434 to 616 nm in dimethylformamide. Polyethylene terephthalate woven fabric could be dyed with the synthesised temporarily solubilised dyes without using any dispersants. Dyebath pH affected the K/S value at maximum absorption as well as percentage exhaustion on polyethylene terephthalate fabric, and the optimum pH was 5. The dyes gave brownish orange, red, purple, and greenish blue hues on polyethylene terephthalate fabrics, and colour build‐up was good. Wash fastness was good to excellent, rubbing fastness was moderate to excellent, and light fastness was poor to moderate.     

Dyeing and finishing of lyocell union fabrics: an industrial study

Lyocell union fabrics, namely lyocell/silk and lyocell/polyester fabrics, were woven in different fabric constructions and dyed with reactive dyes, acid dyes and a disperse dye. The resulting dyed fabrics were given a resin finishing treatment and their wash fastness was measured. With appropriate dye selection and control of dyeing conditions, some bright solid shades and effective cross‐dyed shades were obtained. The dyed and finished fabrics had a smooth, lustrous handle, ideal for lightweight garments.     

One‐step dyeing of polyethylene terephthalate fabric,combining pretreatment and dyeing using alkali‐stable disperse dyes

In the conventional dyeing process, polyester and its blended fabrics are usually dyed in a weak acidic medium. In order to reduce cost and improve production efficiency, a new dyeing method – one‐step dyeing of polyethylene terephthalate fabrics, combining pretreatment and dyeing in alkali conditions – was investigated. The alkali‐stable disperse dyes Red 900, Red 902, Yellow BROB and Blue 825 were used to dye polyethylene terephthalate fabrics. The dyeing properties of polyethylene terephthalate fabrics in the case of one‐step dyeing at various pH values or sodium hydroxide concentrations were discussed in terms of colour yield, colour parameters and fastness. The performance of one‐step dyeing using alkali‐stable disperse dyes was excellent. The dyed fabric had good fastness. Wet processing could be combined and shortened. One‐step dyeing of polyethylene terephthalate fabrics could reduce the consumption of water and energy and improve production efficiency. One‐step dyeing of polyethylene terephthalate has potential application in cleaner textile production.     

Solubilisation kinetics of some monoazo naphthalimide disperse dyes containing butyric acid and investigation of fastness properties of the dyes on polyester

In this paper, the solubilisation kinetics of three novel monoazo disperse dyes based on naphthalimdes incorporating a butyric acid group were investigated in different conditions using spectrophotometry. All dyes showed a reasonable level of solubilisation in alkaline media. Kinetic studies of the solubilisation reaction of the dyes in alkaline media showed that the rate of solubilisation of all dyes is a pseudo first‐order reaction equation. The rate constants of the solubilisation reaction of the dyes in alkaline media indicated that dye 3 , which is prepared by the diazotisation of 4‐amino‐n‐butyric acid 1,8‐naphthalimide and coupled with N,N‐diethy‐n‐hydroxyethyllaniline, has the highest rate of reaction and dye 1 , which is prepared by the diazotisation of 4‐amino‐n‐butyric acid 1,8‐naphthalimide and coupled with N,N‐diethylaniline, has the lowest rate. The dyes were applied on polyester fabrics and their fastness properties were examined. The dyed fabrics showed a good to excellent degree of wash and rubbing fastnesses after replacing reduction clearing with alkali clearing.     

The colour properties of polyester/cotton knitted fabrics coated with poly(N‐vinyl‐2‐pyrrolidone)

The objective of this research was to investigate the use of crosslinked poly(N‐vinyl‐2‐pyrrolidone) (PVP) to coat polyester/cotton knitted fabric, without adversely affecting its dyeing properties. Before dyeing, the knitted fabrics were tested for bursting strength to assess the influence of the coating on their resistance. The dyeing parameters were evaluated as the exhaustion (%), K/S value, colour difference (ΔE), relative strength (RS %) and colour fastness to washing. Bursting strengths were 9.4 for coated and 9.7 kgf cm^?2 for uncoated knitted fabric samples, confirming an insignificant loss in resistance. In the evaluation of K/S, ΔE and RS%, the values for the samples with the highest concentration of PVP were the most different to those for the standard sample. The colour fastness showed satisfactory results indicating that neutralisation and washing after dyeing were effective. These results could lead to increased quality in the textile industry, adding value to products.     

Neutral dyeing of wool and wool/polyester blend fabrics using sulphatoethylsulphone reactive‐disperse dyes

Two models of temporarily anionic sulphatoethylsulphone reactive disperse dyes were applied to wool, polyester and wool/polyester blend fabrics at different dyeing pH. Maximum exhaustion values and colour yield were observed at pH 7. The results showed that reactive disperse dyes containing bis‐sulphatoethylsulphone reactive groups were more convenient for neutral dyeing of wool and wool/polyester blend fabrics if compared with a dye containing a mono‐sulphatoethylsulphone group. Excellent to very good wet fastness properties on all dyed fabrics were achieved.     

Pretreatment of cotton fabrics with polyamino carboxylic acids for salt‐free dyeing of cotton with reactive dyes

In this study, polyamino carboxylic acids have been used to improve the dyeability of cotton in a salt‐free reactive dyeing process. These polyamino carboxylic acids were prepared by partial carboxylation of polyvinylamine. Cotton fabric was pretreated with polyamino carboxylic acids and dyed with reactive dyes. The colour strengths of the dyed fabrics were evaluated by measuring the K/S values. The fastness properties (washing, rubbing and light fastness) of the dyed cotton fabrics were also measured. The pretreatment of cotton with polyamino carboxylic acids creates positive charges on the fabric surface. In this way, salt‐free reactive dyeing of cotton or dyeing with only a small amount of electrolyte is possible.     

Synthesis,stability and printing properties of a novel 2‐sulphophenoxy‐4‐chloro‐s‐triazine reactive dye for ink‐jet printing of wool

We report here the synthesis and characterisation of a new medium‐reactivity reactive dye containing 2‐sulphophenoxy‐4‐chloro‐s‐triazine, having enhanced the activity of the chlorine atom for further substitution by the functional groups carried by wool fibre. In addition, a dichloro‐s‐triazine dye was also synthesised for the purpose of comparison. The progress of synthesis reactions and purity of the dyes were determined using capillary electrophoresis and thin layer chromatography. The molecular structure and the chemical compositions of the synthesised dyes were confirmed using Fourier Transform–infrared spectral data and elemental analyses. The inks containing the synthesised dyes were formulated and ink‐jet‐printed onto wool fabrics and then the printed fabrics were steamed at 102°C. Compared with the dichloro‐s‐triazine dye, superior performance in terms of ink stability, K/S and dye fixation was observed for the new 2‐sulphophenoxy‐4‐chloro‐s‐triazine dye. In addition, the light fastness of the fabric printed with the inks containing the new dye was 0.5‐grade greater than that of the fabric printed with the inks containing the dichloro‐s‐triazine dye, and no changes in shade and staining were observed following wash fastness tests of the fabrics printed with the inks containing the new dye.     

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester,nylon and acrylic fabrics†

1,3,3‐Trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1a ) and 6′‐piperidino‐1,3,3‐trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1b ) were applied as disperse dyes to polyester, nylon and acrylic fabrics. Under optimised dyeing conditions, photochromic fabrics were produced which, on irradiation with ultraviolet or exposure to sunlight, turned blue ( 1a) or blueish‐purple ( 1b ). Dye 1a showed enhanced photochromic colour change performance compared with dye 1b . The photochromic colour build was highest on nylon and lowest on acrylic fabric. The colour change properties and the technical performance (wash fastness and photostability) of the photochromic fabrics were evaluated using specifically adapted colour measurement methods. The data were analysed in terms of variation of lightness, a*, b*, chroma, hue angle and ΔE, colour difference before and after exposure, and K/S curves as a function of irradiation time. The fabrics generally showed good wash fastness. Although the colour build‐up decreased with exposure to the Xenotest fadeometer, some residual photochromism remained after prolonged exposure.     

Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

Acid dyes are employed for commercially dyeing silk, which results in ionic bonds between the silk fibroin and the dye. This generally leads to low wet fastness properties for dyed silk fabrics. In this work, three commercial acid dyes with aromatic primary amine structures were selected to dye silk using a Mannich‐type reaction, resulting in improved wet fastness of dyed silk by forming covalent bonds between silk fibroin and dye. The Mannich‐type reactive dyeing was applied to silk fabrics at both 30 and 90°C in trials. Dyeing at 90°C can shorten the dyeing time compared with dyeing at 30°C, even although dye exhaustion and relative fixation at 90°C were a little lower. The dyeing process was optimised when the dyeing temperature was 90°C, dyebath pH 4, dye‐to‐formaldehyde ratio 1:30 and holding dyeing time 60 minutes. The results showed that the dye exhaustion on silk fabrics for the three aromatic primary amine‐containing acid dyes exceeded 94% and their relative fixation was over 80%. Their washing and rubbing fastness reached grade 4 or higher. Hence, the colour fastness properties of dyed silk fabrics using the Mannich‐type reactive dyeing method is superior to the conventional acid dyeing method using the same aromatic primary amine‐containing acid dyes. The Mannich‐type reactive dyeing for silk fabrics at 90°C can be developed into a novel and rapid reactive dyeing method, promising an effective dyeing process with excellent colour fastness.     

Cetylpyridinium chloride cationic finishing improves the dyeing and antibacterial properties of madder dyed cotton

In this work, after cationic pretreatment of cotton fabric with cetylpyridinium chloride (CPC), the compound of citric acid (CA) and succinic acid (SUA) were used as crosslinking agents to dye cotton fabrics with natural madder dye to improve the dyeing and antibacterial properties and realise the multifunctional finishing of cotton fabric. The effects of mordant dyeing, CA + SUA crosslinked dyeing, and CPC/CA + SUA crosslinked dyeing on the microstructure and properties of cotton fabrics were compared. The dyeing by the three processes occurred primarily in the amorphous zone of the fibres, and all kept the original crystalline form of the cotton. CA + SUA crosslinked dyeing and CPC/CA + SUA crosslinked dyeing increased the thermal stability of the cotton fabric. CPC/CA + SUA crosslinked dyed cotton obtained excellent dyeing results with the colour depth value (K/S) of 12.3 and rubbing fastness and washing fastness of levels 4–5, and the levelness and dye permeability were acceptable. Furthermore, the antibacterial rate against Escherichia coli and Staphylococcus aureus reached 99.99%, and the ultraviolet protection factor (UPF) reached 50+. Moreover, the wrinkle recovery angle (WRA) increased by 55% compared with raw cotton. This showed that CPC/CA + SUA crosslinked dyed cotton had excellent antibacterial, anti-ultraviolet, and anti-wrinkle performances.     

Application of polycarboxylic acid sodium salt in the dyeing of cotton fabric with reactive dyes

In this study, the effects of polycarboxylic acid sodium salt on the dyeing of cotton with reactive dyes were evaluated by measuring and comparing the K/S values and dyeing fastnesses of the dyed cotton fabric samples. Results showed that the K/S value and dyeing fastness of cotton fabrics dyed with polycarboxylic acid sodium salt, substituting inorganic salts as exhausting agent were close to that of with sodium chloride when dip‐dyeing process was used. While, in pad‐dry dyeing, the K/S value of cotton fabric samples dyed with polyacid salts as exhausting agent was higher than that of with sodium sulfate, and the dyeing fastnesses of these samples were nearly the same. The dyeing mechanism of cotton fabric with reactive dye, using polycarboxylic acid sodium salt as exhausting agent was analyzed. The dyeing exhausting mechanism of reactive dye seems different when the inorganic salt and polycarboxylic acid sodium salt were used as exhausting agent in the dyeing of cotton fabric with reactive dye. The polycarboxylic acid sodium salt, as weak electrolyte, increased the dye‐uptake of reactive dye on cotton fabric not only by screening negative charges on cotton surface, but also by the effect of salting‐out or hydrophobic combination. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007     

Optimising by response surface methodology the dyeing of polyester with a liposome‐encapsulated disperse dye

Optimisation of conditions for dyeing polyester with liposome‐encapsulated CI Disperse Red 50 was performed using response surface methodology. The effects of temperature, time, and lecithin:dye ratio on the colour strength of dyed fabrics were investigated by a central composite design. The coefficient of determination, the probability value in analysis of variance, and the normality plot of residuals demonstrated sufficient significance of the proposed fitness function. It was found that the temperature and time of the dyeing cycle were effective factors in the dyeing of polyester fabrics with encapsulated dye. It was also established that the colour yield of dyed fabrics was above 25 in the case of a dyeing time of >80 min, a lecithin:dye ratio of ≤2, and a temperature of ca. 128 °C. Comparison of colour strengths produced by liposome‐encapsulated dye and commercial dye revealed that there was approximately the same build‐up on polyester. Dyeings from encapsulated CI Disperse Red 50 exhibited very similar fastness to dyeings from conventional CI Disperse Red 50.     

Dyeing of poly(lactic acid) fibres with synthesised novel heterocyclic disazo disperse dyes

Poly(lactic acid) (PLA) is the first melt‐processable, renewable, sustainable and biodegradable natural‐based synthetic fibre. It has a broad range of uses and combines ecological advantages with outstanding performance in textiles. PLA fibre, as an aliphatic polyester, can be dyed with disperse dyes. Apart from the limited number of commercial disperse dyes, disperse dye exhaustion on PLA is generally lower than that on  poly(ethylene terephthalate) (PET). In this study, new heterocyclic disazo disperse dyes, substituted with methyl, nitro and chloro groups at their ortho‐, meta‐ and para‐ positions, synthesised in our previous study, were applied to PLA and PET fibres to examine their dyeing performance, and colour fastness and dye exhaustion properties. Different shades of yellow, orange, reddish brown and brown were obtained. Most of the synthesised novel heterocyclic disazo disperse dyes exhibited good build‐up properties with high K/S levels on both fibres. Para‐ bonding substituent provided higher K/S values than meta‐ and ortho‐ positions for –NO₂ and –Cl substituents for both fibres. Overall, the most synthesised novel heterocyclic disazo disperse dyes in this study exhibited good build‐up properties with high K/S, exhaustion and wet fastness levels on both PLA and PET fibres.      

Alkaline dyeing of polyester and polyester/cotton blend fabrics using sodium edetate

An alkaline dyeing of polyester with an alkali‐stable disperse dye, Dianix® Scarlet AD‐RG, was developed using sodium edetate as an alkaline buffering agent. The results obtained indicate the suitability of using sodium edetate for alkaline dyeing of polyester when compared with the control alkaline dyeing using Dianix AD system. Selected mono and bifunctional reactive dyes were used in combination with the alkali‐stable disperse dye for dyeing of polyester/cotton blend. Different dyeing methods for cotton and polyester/cotton blend fabrics using sodium edetate were evaluated in comparison with their respective control alkaline dyeing methods. The results of using sodium edetate in one‐bath two‐stage and two‐bath dyeing of polyester/cotton blend were comparable with that of the control dyeing method. Particularly, no change in the leveling and fastness properties was evaluated for all samples irrespective of the dyeing method. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008