The evaluation of procedures for dyeing silk with buckthorn and walloon oak on the basis of colour changes and fastness characteristics

In this study, silk fabric samples were dyed according to various procedures with buckthorn (Rhamnus petiolaris Boiss) and walloon oak (Quercus ithaburensis Decaisne) extracts. Reversed‐phase high‐performance liquid chromatography with diode‐array detection was utilised for the identification of dyes present in the dyed silk fabrics and the plant extracts. The extraction of dyes was carried out with a hydrochloric acid/methanol/water (2:1:1; v/v/v) mixture. The colour coordinates of the silk fabrics were measured, and the rubbing, wash and light fastness properties of the dyed silk materials were determined and are discussed.     

High‐performance liquid chromatography of some natural dyes: analysis of plant extracts and dyed textiles

In this study, wool fibre samples were mordanted by means of 25% alum mordant solution. The mordanted wool samples were dyed in 50%Reseda luteola L. (weld), 20%Rhamnus petiolaris Boiss (buckthorn) and 50%Datisca cannabina L. (bastard hemp) dyebaths. A reverse‐phase high‐performance liquid chromatography with diode‐array detection method was utilised for the identification of dyes in the dyed wool samples and the plant extracts. The extraction of dyes was carried out with a hydrogen chloride/methanol/water (2:1:1; v/v/v) mixture.     

Preparation and properties of Fe(II)‐ion‐sensitive colour‐changing fabric

Textile fabrics were dyed with complexometric indicators (ionochromic dyes) to develop Fe(II) ionochromic fabric. Three kinds of ionochromic dye were used to dye silk fabric, and they were evaluated for colour changes triggered by Fe(II) solution. The K/S values and photos of the fabrics were then recorded. It was found that 1,10‐phenanthroline was the most suitable ionochromic dye in these dyes. Colour change from white to red could be clearly seen when 1,10‐phenanthroline‐dyed silk fabric was triggered by Fe(II) solution, but it showed no colour change when triggered by Cu(II), Mg(II), or Ca(II) solution. Moreover, 1,10‐phenanthroline‐dyed nylon, polyester, and cotton fabrics showed no obvious colour changes after triggering by Fe(II) solution. Ion concentration, pH value, and reaction time could affect the colour changes. When triggered by 8 mg l^?1 of Fe(II) solution at neutral pH for about 15 min, the ionochromic fabric showed a clear colour change. In addition, three coloured fabrics in green, blue, and yellow were also dyed with 1,10‐phenanthroline. It was found that they could also show clear colour changes when triggered by Fe(II) solution. These ionochromic fabrics may find broad application in many fields, such as Fe(II) detection, magic toys, anticounterfeiting materials, and bionic silk flowers.     

Polydopamine‐coated silk yarn for improving the light fastness of natural dyes

One of the problems occasionally associated with the use of natural dyes in the dyeing of silk is the susceptibility of the dyed yarn to fading in light. While a number of approaches have been used to address this problem, the use of polydopamine (PDA), a known agent with photo‐protective properties, has not been assessed previously. In this study, silk was pretreated with nano‐particulate PDA formed in situ by oxidation of a dopamine solution, then dyed with lac dye or annatto dye as model natural dyes. Photofading rates were significantly reduced in the case of annatto‐dyed, PDA‐coated silk relative to uncoated silk, while wash fastness was unaffected and remained only moderately good. In contrast, no significant change was seen in photofading rates with treated or untreated lac‐dyed silk, and wash fastness was also unaffected. The PDA did not adversely affect resultant colour values if the concentration of the dopamine precursor was kept low. When this was done, acceptable colours were obtained in the dyed silk. Further investigation is warranted of PDA as a photofading protectant and mordant with other natural dyes on silk and other fibres.     

Investigation on colour,fastness properties and HPLC‐DAD analysis of silk fibres dyed with Rubia tinctorium L. and Quercus ithaburensis Decaisne

Silk fabric samples were dyed according to the various procedures using madder (Rubia tinctorium L.) and walloon oak (Quercus ithaburensis Decaisne) extracts. The colour coordinates, K/S, as well as wash, light, rub and perspiration fastness values were determined. A reversed‐phase high‐performance liquid chromatography with diode‐array detection was utilised for the identification of the components of dyes present in the dyed fabrics and in the plant extracts.     

Physical,chemical, and dyeing properties of Bombyx mori silks grafted by 2‐hydroxyethyl methacrylate and methyl methacrylate

To obtain silk weight gain and to improve silk properties, Bombyx mori silks were grafted with either 2‐hydroxyethyl methacrylate (HEMA) or methyl methacrylate (MMA). The moisture regain of the HEMA‐grafted and MMA‐grafted silks depended on the hydrophilicity of the used monomers. The acid and alkaline resistances of the HEMA‐grafted and MMA‐grafted silks were clearly improved. Both commercial synthetic dyes, that is, acid and reactive dyes, and a natural dye extracted from turmeric, with potassium aluminum sulfate as a mordant, were used in this study. The results suggested that the dye uptake increased in the presence of poly(2‐hydroxyethyl methacrylate) or poly(methyl methacrylate) in the silk fibroin structures when acid and curcumin dyes were used. The washfastness level of the HEMA‐grafted silk dyed by acid and reactive dyes was similar to that of the degummed silk. However, the colorfastness to washing of the MMA‐grafted silk dyed by an acid dye was improved when the polymer add‐on concentration was 65%. In addition, the washfastness for both grafted silks was improved when they were dyed with natural curcumin dyestuff. The acid and alkaline perspiration fastness properties remained unchanged for the HEMA‐grafted and MMA‐grafted silks when acid, reactive, and curcumin dyes were applied. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007     

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.     

Eco‐friendly pretreatment of silk fabric for dyeing with Delonix regia extract

The flowers of Delonix regia have been evaluated for the natural dyeing of silk using a biomordant and enzymes. This is an eco‐friendly textile pretreatment that does not utilise metal mordanting. The aqueous extract obtained from the dried red flowers was used for the dyeing of silk fabrics. A bright reddish‐brown hue colour was observed when 30% owf Delonix extract was used on the pretreated silk material. The silk fabric was treated with either an enzyme or biomordant. The resulting dyed fabric showed resistance to fading. Finally, all dyed specimens were tested for wash and light fastness properties, making Delonix a viable alternative to synthetic red dyes. Through desorption studies, the order of reactivity of enzymes towards dye uptake in the one‐step process was found to be lipase > diasterase > protease–amylase = Pyrus(biomordant). For the two‐step process, the order of reactivity of enzymes was found to be protease–amylase > lipase > Pyrus (biomordant) > diasterase. Overall, it can be concluded that, treatments, the two‐step process was better in terms of larger colour yield values, fastness properties and both dye adherence ability.     

Extraction of natural dyes from Alpinia blepharocalyx K. Schum. for dyeing of silk fabric

Natural dyes were extracted from the leaves and stems of Alpinia blepharocalyx K. Schum. Analysis of the designed experiment revealed that extraction at a plant/water ratio of 1:20 could reach an optimal production of natural dyes when extraction was performed at 80 °C, for 4 h, under 20 min ultrasound, in the presence of 10 g/l sodium hydroxide, and with two extractions. The extracted natural dyes were applied to the dyeing of silk fabrics using different methods, including or excluding a mordant. It was found that mordants had a significant effect on the colour of dyed silk fabrics. The silk fabric dyed with the pre‐mordant method using potassium aluminium sulphate as a mordant showed a bright yellow with a higher colour strength. The optimal dyeing conditions were reached when the extracted natural dyes were pre‐mordanted with 10 g/l potassium aluminium sulphate at pH 6, and for a 20 min dyeing time.     

Application of D‐optimal design in the analysis and modelling of dyeing of plasma‐treated wool with three natural dyes

Both the dyeing and finishing of textiles with natural compounds are gaining increasing attention because of various environmental and health problems associated with the use of synthetic reagents. In this study, wool fibres were dyed with three natural dyes, namely, Arnebia euchroma, cotton pods and harmal seeds. Alum was used as the mordant, and samples were mordanted by the premordanting method. Oxygen plasma was employed for the surface modification of wool. Plasma treatment time, alum concentration, dyebath temperature and pH were selected as the process variables, and their effects on the K/S of the dyed samples were analysed using D‐optimal design. The surface topography, morphology and chemistry of the wool fibres after plasma treatment were studied by atomic force microscopy (AFM), scanning electron microscopy (SEM) and Fourier Transform–infrared spectroscopy (FTIR), respectively. FTIR confirmed the creation of new oxygen‐containing groups on the surface of wool fibres after plasma treatment. SEM and AFM images confirmed the surface etching and increase in the roughness of plasma‐treated fibres. Increasing the dyebath pH and temperature increased the K/S of the dyed samples. Increasing the amount of alum mordant increased the K/S of samples dyed with cotton pods but decreased the K/S of samples dyed with A. euchroma and harmal seeds. Increasing the plasma treatment time improved the K/S of samples dyed with A. euchroma and cotton pods but had no significant effect on the K/S of samples dyed with harmal seeds.     

Synthesis and application of KM‐type reactive dyes containing 2‐ethoxy‐4‐chloro‐s‐triazine

A new kind of hetero‐bifunctional reactive dye containing 2‐ethoxy‐4‐chloro‐s‐triazine, with better activity matching with β‐hydroxyethyl sulphone sulphate at a low fixation temperature, was successfully synthesised and characterised. An ethoxy group was designed to be introduced into triazine to increase the substantivity and the reactivity of the dyes. Thereby, the fixation of mono‐s‐chlorotriazine/hydroxyethyl sulphone sulphate (KM‐type) bifunctional reactive dyes on cotton was improved, and dyeing under mild conditions with high fixation was realised. Nineteen dyes with orange, red and blue colours were synthesised and characterised by UV‐Vis and infrared spectroscopy and mass spectrometry. Synthesised dyes were dyed at 60, 75 and 90°C, respectively. Exhaustion and reactivity for all of the ethoxy‐containing KM‐type dyes was over 90% at the optimal temperature, and fixation was over 87%, which was higher than the ethoxy‐free comparative dyes. The optimal fixation temperature of ethoxy‐containing dyes was initially reduced to 75°C, and then to 60°C. Compared with comparative dyes, the wash fastness and light fastness were basically unchanged, and the wet rub fastness of the H‐acid series was reduced by one grade.     

Improving the UV resistance of aromatic poly(l,3,4‐oxadiazole) fiber using a disperse dye modified with octavinyl POSS. Part 1: Preparation of dye and dyeing

Modified dyes were obtained by grafting of disperse dyes with octavinyl polyhedral oligomeric silsesquioxanes (POSS) using a Friedel‐Crafts alkylation reaction and using different ratios of POSS and the original disperse dye. The modified dyes are used to dye aromatic poly(l,3,4‐oxadiazole) (p‐POD) fiber to improve its UV resistance. Then the structure of the modified dye is characterized by Fourier transform infrared spectroscopy and NMR, and the effects of the structure of the modified dye and the dyeing conditions on the UV resistance and color strength (K/S value) of the dyed samples are investigated. The results indicated that the UV adsorption peaks of the modified dye solutions are located at the specified UV wavelengths. The UV resistance of the p‐POD fiber dyed with the modified dye (1:3) can be effectively improved, and the dyed p‐POD fiber can obtain a higher K/S value simultaneously. During the dyeing process, increasing the dyeing temperature and prolonging the dyeing time are both beneficial in improving the anti‐UV ability of the dyed p‐POD fiber; these changes can effectively promote the fixation of dye molecules into p‐POD fibers due to stimulating the motion of dye molecules and p‐POD macromolecules. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 44745.     

Aryl and heteroaryl azo dyes derived from 6, 8‐dichloro‐4‐hydroxyquinolin‐2 (1H)‐one: synthesis,characterisation, solvatochromism and spectroscopic properties

In this research study, 6, 8‐dichloro‐4‐hydroxyquinolin‐2(1H)‐one was prepared by the thermal cyclocondensation of 2‐(2, 4‐dichlorophenylcarbamoyl) acetic acid or N, N?‐bis(2,4‐dichlorophenyl)malonamide at 140‐150°C in polyphosphoric acid, resulting in a yield of 48%. This compound was then coupled with a series of diazonium salts derived from aromatic and heteroaromatic amines for synthesis of the corresponding azo dyes. The structures of the compounds were confirmed using elemental analysis as well as ultraviolet‐visible, Fourier Transform‐infrared and proton nuclear magnetic resonance spectroscopy. The effects of organic solvents with different polarities, pH values and substituents of the diazotising components on the maximum absorption wavelength of the colorants were discussed and evaluated in detail. The acidity constants (pK_a) of the dyes were also determined using the spectrophotometric method in an ethanol‐water mixture (80:20, v/v) at 20‐23°C.     

Antimicrobial activity of some new 4‐arylazo‐3‐methylthiophene disperse dyes on polyester fabrics

A series of novel 4‐arylazo‐3‐methylthiophenes was synthesized by the heterocyclization of 2‐arylhydrazono‐2‐acetyl thioacetanilide derivatives with a variety of α‐halogenated reagents, such as chloroacetone, phenacyl bromide, ethyl chloroacetate, and chloroacetonitrile. The structures of the synthesized thiophene derivatives were confirmed by ultraviolet–visible, IR, and ¹H‐NMR spectroscopic techniques and elemental analysis. The synthesized dyes were applied to polyester fabrics as disperse dyes, and their fastness properties were evaluated. The dyed polyester fabrics displayed antibacterial efficacy against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

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.     

Synthesis of a new,yellow crosslinking polyvinylamine dye and its crosslinking/dyeing process through a crosslinker

A new, yellow crosslinking polyvinylamine dye was synthesized by the reaction of 2,4‐dinitrochlorobenzene with polyvinylamine prepared from Hofmann degradation of polyacrylamide. It was crosslinked and dyed to cotton and silk by a crosslinker synthesized from 1,3,5‐trichloro‐s‐triazine and sodium 2‐(p‐aminophenylsulfonyl)ethyl sulfate. The crosslinking/dyeing conditions of the yellow polyvinylamine dye, such as pH, cure temperature, and concentration of the crosslinker were investigated. The fixations of the polymeric dye by the crosslinker on cotton and silk were greater than 99%. The crosslinking covalent dye–fiber bond was proved indirectly by the comparison of IR spectra of the undyed fiber, the dyed fiber, and the crosslinked one, and also by the fact that no dye was stripped off from the crosslinked and dyed sample by extraction with DMF/water (1 : 1). © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 1568–1573, 2006     

Dyeing properties of Bombyx mori silks grafted with methyl methacrylate and methacrylamide

To improve their dyeing and colorfastness properties, degummed Bombyx mori silks were chemically modified by a grafting technique with either methyl methacrylate (MMA) monomer or methacrylamide (MAA) monomer. Both commercial synthetic dyes, that is, acid and basic dyes, and natural dyes extracted from turmeric, without and with potassium aluminum sulfate mordant, were used in this study. Percentage dye uptake increased with the presence of poly(methyl methacrylate) or polymethacrylamide in the silk fibroin structure regardless of the types of the dyestuffs. Furthermore, compared to the degummed silk, the colorfastness to washing of the MMA‐grafted and MAA‐grafted silks dyed with acid, basic, and curcumin dyestuffs were greatly improved. Colorfastness to both acid and basic perspirations with acid and basic dyestuffs was slightly improved, whereas perspiration fastness remained unchanged for curcumin dyeing without and with the presence of the mordant. Also, the low‐light resistances of the degummed and grafted silks dyed by curcumin dyestuff were notably improved by the MMA and MAA grafting technique. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100:1169–1175, 2006     

The accelerating effect of a small cationic quaternary ammonium compound and the adsorption kinetics in the dyeing of silk with reactive dyes

In order to develop an eco‐friendly method for silk reactive dyeing that uses a lower accelerant dosage to achieve a higher dye fixation, hexyl dimethyl octyl ammonium chloride was synthesised as an accelerant for the dyeing of silk with reactive dyes. The accelerating effect, corresponding adsorption kinetics, and interaction mechanisms among hexyl dimethyl octyl ammonium chloride, reactive dyes, and silk were investigated. At hexyl dimethyl octyl ammonium chloride concentrations of 10.8–14.4 mm , the dye fixations for three reactive dyes were much higher than those achieved with sodium sulfate, even though the required dosages of hexyl dimethyl octyl ammonium chloride were 30–40 times lower than those of sodium sulfate. The wash fastness, rub fastness, light fastness, K/S, and colour difference values after dyeing with hexyl dimethyl octyl ammonium chloride were similar to those obtained using sodium sulfate, and silk can be dyed uniformly. The adsorption kinetics followed a second‐order kinetic model. The activation energies of surface adsorption for the three reactive dyes were lower than those of sodium sulfate. The high fixation of reactive dyestuffs and the low required dosage of hexyl dimethyl octyl ammonium chloride demonstrate that the use of this new accelerant provides a novel, highly efficient method for silk dyeing. A possible acceleration mechanism of hexyl dimethyl octyl ammonium chloride for reactive dyes adsorbed on the surface of silk was proposed, based on a series of activation parameters of the adsorption process.     

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.     

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.