Study on coloration of silk based on coupling reaction with a diazonium compound

This paper describes how coloration of silk can be achieved using a coupling reaction between a diazonium compound, made from Color Base Red G (C.I. 37105) and tyrosine residues in the silk protein fibroin. A pigment with an azo structure obtained from the reaction between the diazonium of Color Base Red G with p-methylphenol was synthesized and studied as a model compound for the coloration reaction. The colored materials were characterized using UV-vis, FT-Raman, FT-IR, ¹H-NMR, and mass spectroscopy. Both the colored silk and the model compound gave yellow colors with absorption maxima in the region of 400 nm. The results suggest that the use of coupling reactions could be developed into a dyeing method for protein fibers or other protein materials that contain tyrosine residues. Because the chromophores are incorporated into the protein chains, such dyed silks should have good wet fastness properties.     

Eco-friendly dyeing using natural mordant extracted from <Emphasis Type="Italic">Emblica officinalis G</Emphasis>. Fruit on cotton and silk fabrics with antibacterial activity

Emblica officinalis G. dried fruit tannin was extracted and applied as a natural mordant alone and in combination with metal mordant namely copper sulphate for dyeing on cotton and silk fabrics using natural dyes. The color strength, color-coordinates, wash and light fastness were also evaluated for cotton and silk fabrics with and without mordanting. The pre-mordanted cotton and silk fabrics on dyeing gave better color strength, wash and light fastness than those dyeing obtained without mordanting. The total phenolic content of the extract was calculated. Cotton and silk fabrics resulted in good antibacterial activity using the Emblica officinalis G. mordant. When mordant was used along with 0.5 and 1 % copper sulphate mordant and the activity enhanced and was active up to 20 washes.     

Superfine pigment dyeing of silk fabric by exhaust process

The surface of silk is modified by a cationic reagent, N-(3-chloro-2-hydroxypropyl) trimethylammonium chloride(CHTAC) in order to enable the fibre to be dyed with superfine pigments by an exhaust process. The effects of cationization pretreatment conditions such as the amount of cationic reagent, pH, treatment temperature and time on color yield are discussed in detail. The result shows that the condition suitable for modification treatment is that the concentrationc of cationic reagent is 10 g/l, pH 8, liquor to goods ratio of 100:1 and 60°C for 30 min. The white index decreases with the increase of alkali of cationic treatment. The crock fastness and wash fastness of silk dyed by pigment exhaust dyeing achieve 3–4 and 4 scale, respectively. The treated silk fabrics still retain a soft handle because the bending rigidity B and hysteresis 2HB increase slightly after cationization pretreatment and dyeing procedure. It has been demonstrated that properties of surface modified silk dyed with superfine pigment by exhaust process are acceptable.     

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.     

Natural dyeing with black cowpea seed coat. I. Dyeing properties of cotton and silk fabrics

A new trial to determine the dyeing properties of cotton and silk fabrics with a black cowpea seed coat as crop waste was investigated. The natural dye anthocyanins were extracted from a black cowpea seed coat in an aqueous solution and used to dye silk and cotton. The optimal conditions for colorant extraction were an aqueous solution of a dried seed coat of black cowpea in a 1:10 liquor ratio at 70 °C for 4 hours with pH of 4. The best dye-uptake of silk and cotton fabric were obtained when the pH was 3.5 and 3.0 respectively, the temperature was 80 °C for 1 hour and the liquor ratio of black cowpea was 1:20. Different colors as dusky brown, brown, faint yellow, light green, reddish brown, cyan and green could be obtained using a various kind of mordants. The depth and brightness of color tones were affected by different dyeing and mordanting pH conditions. The colors of the fabrics were examined using a computer color matching system in terms of the K/S values and CIELAB color-difference values. The dyeing was evaluated using standard light, wash and heat fastness tests. Good wash and heat fastness were obtained but the poor light fastness indicated the need for improvement to fulfill the requirement for textile applications.     

Grafting of tyrosine-containing peptide onto silk fibroin membrane for improving enzymatic reactivity

During enzymatic modifications of silk fibroins, the accessibility of tyrosinases to the reactive sites was limited owing to the steric hindrance of tyrosine residues in the fibroin proteins. To improve the reactivity of silk fibroin, a tyrosine-containing peptide (TyrP) was covalently grafted onto the fibroin surfaces using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC). Enzymatic oxidation of the modified fibroins was subsequently carried out with a mushroom tyrosinase, followed by coupling of ε-polylysine (ε-PL) with the generated o-quinone residues of silk fibroins. The efficacy of grafting reaction was examined by means of SDS-PAGE and amine acid analysis. The results indicated EDC treatment might cause the direct self-crosslinks of silk fibroins and TyrP-bridged cross-links of fibroin molecules as well, which led to a noticeable increase in the molecular weight of fibroin proteins. TyrP-grafted fibroins displayed higher reactivity compared to the untreated, and more ε-PL was bonded to the fibroin surfaces when incubating with tyrosinase, resulting in improved wettability and mechanical property. The presented work offers an efficient alternative for the enzymatic modification of the fibroin-based materials with tyrosinase.     

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.     

A novel eco-friendly colorant and dyeing method for poly(ethylene terephthalate) substrate

Although madder (Rubia tinctorum) has been used as a well-known natural textile dye source for dyeing of natural fibers such as wool, silk and cotton, 100 % polyester dyeing with madder is not common. In this study, polyester samples were dyed with madder at different dyeing temperatures, from 60 °C to 130 °C, in company with 7 chemical and 5 natural mordants. Color properties and rub, light and wash fastness performances were investigated. Different shades of orange, brown, pink and reddish green colors were obtained. Dyeing at 130 °C exhibited the highest color yield, the highest chroma and the lowest lightness values. Overall, chemical mordants exhibited higher color yields than natural mordants. High wash fatness, moderate light and rub fastness levels were observed. The potassium bitartrate and gallnut, a natural mordant, exhibited the best results. The madder dyeing of polyester should be carried out at hot temperature conditions, 130 °C, in order to obtain the highest achievable color yield and chroma with the highest light and wash fastness properties.     

Dyeing of synthetic fabrics in water using azoic dyes based on boronic acid derivatives

Development of water-soluble dyes for the dyeing of different textile fabrics is essential for the textile industry due to ecological and economical reasons. In this study, a series of new azoic dyes were prepared by diazotization reaction between the phenyl boronic acid and different aniline derivatives, and their dyeing capacity in aqueous solution was evaluated. The synthesized boronic azo dyes present good water solubility and can dye polyamide (nylon), wool, silk, and cellulose acetate fabrics. The effect of factors such as concentration of dye, dyeing temperature, and pH on the level of color strength (K/S) was studied. The dyeing results showed that higher color strength K/S (about 16) and fastness properties (about 4/5) with boronic acid dyes were achieved at higher temperatures avoiding the use of surface agents, mordants, and other polluting chemical additives.     

Natural dyeing of cotton with <Emphasis Type="Italic">Xylocarpus granatum</Emphasis> bark extract: Dyeing,fastness, and ultraviolet protection properties

In this research we investigated the dyeing of cotton fabrics with extracts of Xylocarpus granatum, a mangrove plant with a long history of use in leather tanning and textile dyeing. X. granatum bark was extracted and spray-dried, yielding a tannin-rich, reddish-brown powder. This powder proved a suitable colorant for the natural dyeing of cotton with promising color fastness properties to wet treatments (washing, water, sea water, and perspiration), hot pressing, crocking, and light exposure. However, the dye alone produced only weak levels of coloration and therefore metallic salt mordants were employed to improve the color strength, through the formation of insoluble tannate complexes. The resulting fabric K/S values were dependent on the mordant used and exhibited the following trend: ferric sulfate > sodium dichromate > copper sulfate > potassium aluminum sulfate > no mordant, for fabrics exposed to mordants before and after dyeing. Mordanting resulted in slight variations in shade and color fastness. In most cases, the color fastness properties were preserved, except for color fastness to light and hot pressing, for which lowered ratings were found for some mordants. Stiffness and mechanical performance were not greatly affected by dyeing or mordanting, except for sodium dichromate mordanting which significantly stiffened and weakened the fabric. The ultraviolet protection factor (UPF) of all the dyed samples achieved the maximum (50+) level, highlighting the excellent UV shielding properties of the fabric. Overall, X. granatum bark extract is a promising, effective colorant for the natural dyeing of cotton in terms of appearance, fastness, and physical characteristics.     

The Use of Sumac as a Natural Mordant in Green Production of Iranian Carpet

Dyeing is a state-of-the-art realm of textile engineering, however, the emphasis on petroleum-based products is now shifting towards green fibers, particularly, green manufacturing processes. In the present work, a natural mordant, sumac, was extracted and used alone and in combination with alum (a mineral mordant) in silk fibers dyeing with madder and Reseda green dye to make the green production of Iranian carpet possible. The FT-IR ATR spectra of the washed, mordanted, and mordanted dyed silk fibers revealed bonding between silk fibers and green materials. The color of the silk fibers dyed with madder and Reseda extraction was quantified in terms of CIELab (L*, a*, and b*) and K/S values. The effects of different treatments on fastness properties including light, wash, and rubbing fastness were assessed by ISO standard test method.     

Dyeing and antibacterial properties of <Emphasis Type="Italic">Liriope platyphylla</Emphasis> fruit extracts on silk fabrics

Dyeing and antibacterial properties of a natural dye extracted from Liriope platyphylla fruit applied on silk fabrics have been studied. The total phenolic content (1109.13±69.02 mg), total flavonoid content (530.60±89.44 mg), and total anthocyanin content (492.26±77.79 mg) were measured in 100 g fresh weight of L. platyphylla fruits. In addition, ten anthocyanins and four flavanols were identified in L. platyphylla fruits by high performance liquid chromatography with diode array detection coupled with electrospray ionization mass spectrometry (HPLC-DAD/ESI-MS). A broad variation in color shade and color depth can be achieved with mixtures of dye extracts and metal mordants. Purple, blue, and pale green were main color shades of silk fabrics dyed with the extracts. The fastness of dyed silk fabrics except for control dyed fabrics against light, washing, and rubbing were acceptable with at least a grey scale rating of 3. The antibacterial activities of L. platyphylla fruit extracts were retained on dyed silk fabrics even after home washing 30 cycles. Mordanting with metal salt mordant had a positive effect on antibacterial activity of dyed silk fabrics in this study. Among them, aluminum and copper were the most effective mordants for improving antibacterial activity of silk fabrics dyed with L. platyphylla fruit extracts. The costs of natural dyeing of per silk fabrics kg by the extracts from L. platyphylla fruit were also calculated on laboratory scale.     

Properties of basic dyes on polyacrylonitrile treated m-aramid fabrics

Treatment of polyacrylonitrile (PAN) onto m-aramid fabric was carried out by pad-dry-cure method using dimethylformamide (DMF) dissolved acrylic fiber solution. The obtained PAN treated m-aramid fabric was dyed using exhaustion method with basic dyes. The effect of PAN treatment on fabric stiffness property was acceptable with acrylic fiber solutions ranging from 1 wt% to 4 wt%. Whilst, more than 4 wt% PAN treated fabrics exhibited undesirable stiffness. The dyeing results showed that PAN treated m-aramid fabrics exhibited a significant increase in color strength when compared to untreated fabric, arising from an increase in anionic dye sites (styrene SO₃ ^? group). Wash fastness was comparable to that of untreated fabric, indicating the strong interaction between dye molecules and the PAN. Rubbing fastness of treated fabrics was not affected by treatments with PAN concentrations lower than 4 wt%. Further increase in PAN concentration led to poorer rubbing fastness property due to the problem of surface dyeing. For light fastness, the PAN treatment failed to improve the light fastness property which is the main disadvantage of basic dyeing of aramid fabric. Finally, in case of PAN treatments with the range of 1 wt% to 4 wt%, the flame retardancy property of PAN treated m-aramid fabrics was found not affected by the percent add-on. However, above 4 wt% PAN treatment, the flame retardancy performance became deteriorated.     

Study on the natural dyeing of wool modified with enzyme

In this study, the natural pigment from sappan was used for the dyeing of wool fabrics after treatment with the protease and transglutaminase. The influences of protease and transglutaminase on the UV/visible absorption spectrum of aqueous extract of sappan were studied. The enzymatic modified wool was compared with non-modified wool in K/S value and fastness after direct dyeing and mordant dyeing. It was shown that protease and transglutaminase made the absorbance at the λ _max 540 nm in visible region increase. It suggested that there might be some interaction between the enzymes and sappan dye and the residual enzyme on wool fabric might affect the color of following dyeing. Compared to untreated wool, treatments with protease and transglutaminase enhance K/S value of wool dyed subsequently with sappan. Modification of protease led to some decrease in wet rubbing fastness, whereas transglutaminase had almost no influence on rubbing fastness. Enzymatic treatments have no influence on the washing fastness for samples dyed with sappan.     

Dyeing of cotton and silk yarn with the extracted dye from the fruit hulls of mangosteen,<Emphasis Type="Italic">Garcinia mangostana</Emphasis> linn

The extracted dye from the dried fruit hulls of mangosteen was used as a natural dye for the dyeing of cotton and silk yarn. The optimal conditions for dye extraction were to extract the dried fruit hulls of mangosteen at 80°C for 1 hour with a 15 % w/v citric acid solution in a 1:4 ratio of mangosteen powder to solvent. Cotton dyeing with the extracted dye from the dried fruit hulls of mangosteen was carried out at 60°C for 60 minutes with a material to liquor ratio of 1:25. The effect on dyeing of mordant type with different mordanting methods was studied. The results showed that the dyeing of cotton using the post-mordanting method with ferrous sulfate and calcium hydroxide not only provided better depth of shade but also provided better wash fastness and light fastness than with other mordants (alum; zinc tetrafluoroborate) or without a mordant. Good fastness properties were also obtained using a post-mordanted silk with calcium hydroxide.     

Studies on antimicrobial activity for multidrug resistance strain by using phenyl pyrazolones substituted 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one derivatives in vitro condition and their dyeing performance

Heterocyclic monoazo quinazolinone based azo dyes derived by the diazotization of 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one with various phenyl pyrazolones based coupling components. All the heterocyclic azo dyes have been characterized by their percentage yield, UV-VIS spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy, and dyeing performance on silk, wool, nylon, and polyester fibers. All the dyes gave moderate to excellent fastness properties on each fiber. The main focus was to synthesize heterocyclic monoazo dyes that give good dyeing property along with pharmacological activity (anti bacterial and antifungal). Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.     

Azocalix[4]pyrrole dyes: Application in dyeing of fibers and their antimicrobial activity

The dyeing performance of the azocalix[4]pyrrole dyes on fibers like nylon, wool, acrylic, and silk have been determined. Their fastness properties towards light, water, washing, and acid-alkali perspiration have been studied. The position of color in CIELAB coordinates (L*, a*, b*, H, and C*) was assessed. The azocalix[4]pyrrole demonstrated good antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Aspergillus niger. These super molecules exhibit bright shades on fabric with very good fastness properties.     

Actinomycin X2, an Antimicrobial Depsipeptide from Marine-Derived Streptomyces cyaneofuscatus Applied as a Good Natural Dye for Silk Fabric

Actinomycins as clinical medicine have been extensively studied, while few investigations were conducted to discover the feasibility of actinomycins as antimicrobial natural dye contributing to the medical value of the functional fabrics. This study was focused on the application of actinomycin X2 (Ac.X2), a peptide pigment cultured from marine-derived Streptomyces cyaneofuscatus, in the dyeing and finishing of silk fabric. The dyeing potential of Ac.X2 with silk vs. cotton fabrics was assessed. As a result, the silk fabric exhibited greater uptake and color fastness with Ac.X2. Through Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), and X-ray diffraction (XRD) analyses, some changes of chemical property for the dyed fabric and Ac.X2 were studied. The silk fabric dyed with Ac.X2 exhibited good UV protection ability. The antibacterial properties of dyed and finished silk were also evaluated, which exhibited over 90% antibacterial activity even after 20 washing cycles. In addition, the brine shrimp assay was conducted to evaluate the general toxicity of the tested fabric, and the results indicated that the dyed silk fabrics had a good biological safety property.     

Dyeing of modified acrylic fibers with curcumin and madder natural dyes

Hydrophobic fibers are highly crysta lline and non-polar polymers hence pose a big problem for dyers. Modified acrylic fiber containing different amounts of amidoxime groups as a function of the nitrogen content was obtained and dyed with curcumin and madder natural dyes. The dyeing parameters, such as dye concentration, dye bath pH, salt concentration, temperature, and time and the effect of alum and ferrous sulfate used as mordants were investigated. Compared with the dyeings obtained from modified acrylics, those of blank samples appeared less in color strength values. The color strength was proportional to the nitrogen content of the sample and the maximum value was obtained at pH 2 and pH 5 using madder and curcumin, respectively. The fixation of the dye molecules to the modified acrylic fibers was investigated to show mainly ionic and physical bonds. The washing, perspiration, and rubbing fastness properties for the dyed samples were enhanced by application of alum. The light fastness ratings were also improved using ferrous sulfate especially for the case of the samples dyed with madder.     

Synthesis,spectral characterization of azo dyes derived from calix[4]resorcinarene and their application in dyeing of fibers

Seven new upper rim functionalized azocalix[4]resorcinarene dyes have been synthesized by coupling calix[4]resorcinarene with different diazo compounds of p-chloroaniline, p-nitroaniline, p-toludine, p-anisidine, p-aminobenzoic acid, o-aminophenol, and aniline. The characterization of these dyes has been carried out by elemental analysis, FT-IR, ¹H- and ¹³C-NMR. Effect of solvents of varying dielectric constants on the absorption spectra of substituted and unsubstituted azocalix[4]resorcinarene dyes have been examined by UV-vis spectrophotometer. These azocalix[4]resorcinarene dyes have also been used for dyeing textile fibers like cotton, silk, and wool. Their dyeing and fastness properties have also been discussed.