Light Fastness Properties Research Articles

Synthesis, application and antibacterial activity of new reactive dyes based on thiazole moiety

PurposeThis study aims to synthesise and characterise new reactive dyes based on thiazole derivatives which act as chromophoric moieties. These dyes were applied to cotton fabric, resulting in the dyed fabrics exhibiting good colour strength, light fastness and other fastness properties. The antibacterial activity of the dyed cotton fabric was evaluated against gram-negative and gram-positive bacteria.Design/methodology/approachThe dyes were synthesised in two steps. First, the coupling compound was formed by adding H-acid solution to cyanuric chloride in an ice bath at pH 5 then adding 4-aminobenzenesulphonic acid portion-wise at room temperature and at pH 6-7. Second, different diazonium salts 4-phenylthiazol-2-amine (2a) and 4-(4-methoxyphenyl) thiazol-2-amine (2b) were coupled with the coupling compound at pH 5. The resultant monochlorotriazine (MCT)-reactive dyes (6a, 6b) were formed. The synthesised dyes were applied onto cotton fabric under typical exhaust dyeing conditions and their dyeing properties were investigated.FindingsHigh antimicrobial activity, dye exhaustion and fixation yield on cotton fabric were recorded for each dye. All dyes showed high stability against washing, rubbing, perspiration and light fastness.Research limitations/implicationsDyeing of cotton fabric with these dyes which have higher fastness, higher exhaustion and higher antibacterial activity is considered one of the most important reactive dyes species.Practical implicationsThe preparation procedure showed the synthesis of the novel MCT-reactive dyes derived from thiazole derivatives followed by the application of these dyes on cotton fabrics.Social implicationsUse of reactive dyes will bring a number of benefits to society including higher fastness and higher antibacterial activity so, and these dyes can be used for dyeing cotton.Originality/valueIn this work, the new reactive dyes derived from thiazole derivatives were synthesised and their structures were confirmed by the analytical and spectral data. Such compounds are considered to be excellent reactive dyes with different colour shades and higher antibacterial activity.

Assessing the stability of arsenic sulfide pigments and influence of the binding media on their degradation by means of spectroscopic and electrochemical techniques

In this paper, we used the semiconducting and lightfastness properties of synthetic and mineral arsenic sulfide pigments to study their stability by means of electrochemical and microfadometric techniques. A combination of these techniques shows that in the early stage of the degradation process, amorphous arsenic sulfides are more stable than both crystalline forms, while upon longer exposure time, amorphous pigments will fade more than both mineral pigments, making it less suitable. While the stability study was carried out on unbound pigments, the influence of the organic binder on the relative degradation of the arsenic sulfide pigments was investigated through a multi-analytical approach on pigment/binder mock-up paint samples. For this purpose, the formation of arsenic trioxide was assessed by micro Fourier transform infrared (μ-FTIR) spectroscopy while the influence of the binder on the formation of sulfates was studied by means of synchrotron radiation X-ray near edge structure (μ-XANES). Both techniques elucidate a higher stability of all pigments in gum arabic while the use of egg yolk as binder leads to the most degradation, most likely due to its sulfur-rich composition. In the context of the degradation of arsenic sulfide pigments, other binders such as animal glue, egg white or linseed oil show an intermediate impact.

Synthesis of Direct dyes based on non-carcinogenic amines for leather and textile industry

ABSTRACT: A series of direct dyes based on 4,4'-diaminodiphenylamine-2'-sulphonic acid (1-5) have been synthesized to be used as potential alternative to benzidine ( human carcinogenic) and they are eco-friendly. Benzidine derivatives containing alkoxy groups ortho to an amino group of meta-phenyl diamine removed carcinogenicity. The Benzidine analogue was diazotized and coupled with widely used dye intermediate dye like FC acid to generate a group of direct dyes giving yellow, mustard, blue, purple and greenish black shades on cotton, leather and wool. Dye structures were confirmed by visible absorption spectra, IR spectra, and fastness property. Dye purity was confirmed by TLC using BuOH: EtOH: NH4OH:H2O (3:1:0:5:1) as the fluent. The dyed fabrics showed very good to excellent wash fastness and moderate to good light and perspiration fastness properties.

Ecological risk assessment and health safety speculation during color fastness properties enhancement of natural dyed cotton through metallic mordants

Variety and durability of color are presumed as key constrains of natural dyes. So, this study attempts to investigate the effect of metallic mordants on the color fastness properties of ecologically dyed cotton fabric using banana floral stem sap. Color difference was measured in terms of hue (ΔH*), chroma (ΔL*) and value (ΔC*) difference. Metal ions in residual mordanting bath, dyeing wastewater and level of trace metals in the finished fabric surface were accessed to justify the environmental safety and speculate the health risk respectively. Pre-mordanted specimens were dyed at 100 °C for 60 min. Optical properties of extracted sap were observed by UV visible spectroscopy. Dye fixation with fiber was determined by FTIR-ATR spectra. Atomic absorption spectroscopy was employed to determine the trace metals in finished fabric. Effect of metallic mordants were calculated in terms of color fastness to wash, water, perspiration, rubbing and light for estimating the color durability. Except light fastness property almost all color fastness values were 4/5, i.e. very good. Light fastness properties were improved for mordanting action with metallic salts. The level of trace metals in finished fabric were within the safe zone.Graphical abstractMetallic mordant assisted natural dyeing of cotton.

Synthesis, characterization and ultrafiltration of reactive dyes. Application by exhaustion and/or ink-jet printing. IV.

Three new bis azo reactive dyes of different metallic salts (Na, K, Li) were synthesized. The synthesis was obtained by diazotization of 4-amino-2:5 di methoxy phenylene-beta hydroxyl ethyl sulphone sulphate ester and coupling with 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (H-acid) (moles ratio 2:1). The dyes were purified-concentrated by ultrafiltration technology, characterized and applied on cotton, wool and nylon 6,6 fabric by exhaustion (dyeing) and by ink-jet printing. Fastness properties of the dyeings were measured. Wash fastness was investigated according to international standard methods and was found to be very good to excellent in all cases, while light fastness values were medium to low. Ink-jet ink formulations were prepared using the ultra filtrated reactive blue dyes UF RB(a-c) and their properties pH, conductivity, surface tension and viscosity were monitored over a period of 90 days. The inks were used to print digitally cotton and nylon 6,6 samples and wash- and light fastness properties of the prints were measured. Wash fastness properties were excellent while light fastness values are low Colour measurements of the dyeings and prints were conducted.

Antibacterial evaluation of cotton fabrics by using novel sulfonamide reactive dyes

PurposeThe purpose of this paper was to synthesize novel antibacterial reactive dyes for dyeing cotton fabrics.Design/methodology/approachFour synthetic novel antibacterial reactive dyes based on sulfonamide (D1-D4) have been synthesized by the coupling reaction of sulfonamide diazonium salt with sulfonamido-cyanurated 7-amino-4-hydroxynaphthalene-2-sulfonic acid “j-acid”. The chemical structure of the synthesized dyes was secured by their spectral data [infra red (IR) and proton Nuclear magnetic Resonance (1HNMR)].FindingsThe prepared reactive dyes (D1-D4) were applied to cotton fabrics. Optimum conditions of the dying samples at sodium sulfate 100 g/l, liquor ratio (L.R.) 1:10, sodium carbonate 20 g/l at 80°C (D1, D2 and D4), 60°C (D3 for 60 min) were investigated. The fastness properties toward washing, perspiration, rubbing and light were evaluated. Dyed fabrics showed good light fastness property and good to very good washing and perspiration fastness properties according to the gray scale. Antimicrobial activities for synthesized dyes showed excellent activity against gram-negative organisms such as Pseudomonas aeruginosa and Proteus mirabilis faecalis, whereas very good activity against gram-positive organisms such as Staphylococcus aureus and Enterococcus faecalis with respect to the standard drugs ampicillin and chloramphenicol.Originality/valueThe principle advantages in this study were that the synthesis of novel synthesized dyes by introducing bisulfonamide-based moieties to increase the antimicrobial activity of the cellulose fabrics could be used as a medical textile, short reaction time and reaction procedure conducted in few steps, the work up is convenient and thus the starting material can be easily prepared.

Synthesis of 5-azo-8-hydroxy-2-methylquinoline dyes and relevant spectroscopic, electrochemical and computational studies

Twenty four derivatives of 5-azo-8-hydroxy-2-methylquinoline dyes with twenty three novel structures have been synthesized in an efficient one-pot synthesis protocol. Their properties were characterized by the combination of IR, NMR, MS, HRMS, GC-MS and electronic absorption spectroscopy. Two of the novel dyes have been synthesized as hydrochloride salts and structurally characterized by X-ray crystallography. The oxidation and reduction properties of selected 5-azo-8-hydroxy-2-methylquinoline dyes were studied using cyclic voltammetry. The measured visible absorption spectra of the dyes were discussed regarding the effects of substituent, varying pH and solvent upon their absorption ability. The molecular orbitals of the selected dyes have been calculated by density functional theory (DFT), which demonstrated that the HOMO orbitals were concentrated in the aromatic rings and in the azo part (–N=N–). The calculated HOMO and LUMO energies are in consistence with redox behavior of azoquinolines. The obtained dyes were successfully incorporated into polyester fabrics and their light fastness properties were evaluated.

Stimuli-responsive luminescent coumarin thiazole hybrid dye: Synthesis, aggregation induced emission, thermochromism and DFT study

Novel coumarin thiazole hybrid dye with azomethine linkage was synthesized. The dye is very sparingly soluble in DMF and insoluble in other solvents. The dye shows 2 fold increase in emission enhancement on aggregation caused at 60% DMF-H2O mixture. Differential thermal analysis revealed a change from one polymorph to the other polymorph at 285 °C leading to emission in the red region. Excited State Intramolecular Proton Transfer takes place with thiazole nitrogen atom and not with N atom of azomethine linkage contrary to Pigment Yellow 101. High color value (K/S = 10.42) and light fastness (rating = 8) properties were found as compared to Pigment Yellow 101. The computed absorption and emission values were found closer to the experimental values. The pigment exhibits higher first and second order hyperpolarizabilities (24 times more α0, 248 times more β0 and 756 times more γ value than urea).

Synthesis, characterization and ultrafiltration of reactive dyes. Application by exhaustion and/or ink-jet printing—II

Three novel vinyl sulfone reactive dyes of various metallic salts (Na, K, Li) have been synthesized by coupling 1-amino-phenyl-4-beta hydroxyethyl sulfone sulfate ester with 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (H-acid). The reactive dyes were then purified using ultrafiltration (UF). The ultrafiltrated dyes of the various metallic salts were characterized by their spectrophotometrical data using Ultra Violet-visible (UV-vis), Fourier transform infra-red and optical emission spectroscopy, X-ray diffraction, and elemental analysis. The purity of the dyes was checked by Thin Layer Chromatography (TLC). The solubility characteristics of the various salts of the ultrafiltrated reactive dyes were assessed and compared with the non-ultrafiltrated reactive dyes of the same salts. The dyes were characterized and applied to cotton, wool, and nylon 66 by exhaustion (dyeing). Novel water-based reactive ink-jet inks were prepared with the ultrafiltrated reactive dyes of the various metallic salts. Their suitability for digital printing applications was examined by using a digital printer on suitably pretreated cotton samples. Color and fastness properties measurements were performed for both the dyed and digitally printed samples. K/S values of the dyed samples were higher than those of the digitally printed ones, whereas K/S values of the samples dyed with the ultrafiltrated dyes were much higher than those of the non-ultrafiltrated dyes. The other coloristic co-ordinates L*, a*, b*, C*, and ho were in line with strength changes of the dyes before and after UF. The dyed and digitally printed samples had excellent wash and good light fastness properties. UF slightly improved the fastness properties of the dyed samples.

Eco-friendly Cotton Coloration Using Banana (Musa Sapientum) Waste: Optimization of Dyeing Temperature

Temperature has a promising role in textile coloration process. This study intends to optimize the dyeing temperature for sustainable coloration of cotton fabric employing banana waste. Natural dye retrieved from banana floral stem by roller squeezer machine. To explore the effect of temperature, samples were dyed for 60℃, 70℃, 80℃, 90℃, 100℃ and 110℃ respectively by keeping constant time at 60 minutes. Effect of temperature variation on colorimetric appearance were expressed using CIE L*a*b* color space in terms of color co-ordinates, color strength (K/S), brightness index (BI) and degree of color levelness values. The dye fiber bonding stability was accessed via color fastness to wash, water, perspiration, rubbing and light. Except light fastness property almost color fastness value was 3-5 i.e. good to excellent. Best result of K/S, bright index % and color levelness value recorded 0.65, 50.58 and 0.069 respectively for 100℃. Excellent color fastness properties also appeared for 100℃. This reports prognosis an environmental begins approach for coloration of cotton fabric by deploying of banana plant waste.

Optimization of Dyeing Time of Eco-friendly Cotton Coloration Using Banana (Musa Sapientum) Floral Stem Sap

This study attempts to disclose the optimum dyeing time for exploiting banana agricultural bio-resource waste for sustainable dyeing of cotton fabric. 100% cotton knitted single jersey commercially scoured-bleached fabric used for this experiment having areal density 175 grams per square meter. Natural dye retrieved from banana floral stem by roller squeezer machine. Selected samples were dyed at 100℃ for 20, 30, 40, 50, 60 and 70 minutes respectively. Effect of time variation were calculated using CIE L*a*b* color space in terms of colorimetric properties of colored fabric viz. color co-ordinates, color strength (K/S), brightness index (BI), degree of color levelness. Color fastness to wash, water, perspiration, rubbing and light were valued for estimating the color durability. Except light fastness property all tested color fastness properties were 3-5 i.e. very good to excellent. For all evaluated parameters samples dyed for 60 minutes exhibited best result. This reports forecast a sustainable technology for effective utilization banana floral stem sap bio-resource waste for coloration of cotton fabric.

Light fast monoazo dyes with an inbuilt photostabilizing unit: Synthesis and computational studies

A series of monoazo disperse dyes with a photostablilizing o-hydroxycarbonyl moiety was incorporated resulted in the enhancement of the light fastness properties on polyester and nylon substrates as compared to the dyes that do not possess the photostablilizing moiety. The geometries of the azo and the hydrazone tautomeric forms of all dyes were optimized at B3LYP/6-311+G(d) and electrophilicity index was calculated for propensity of the moiety to absorb electrons. The values of absorption and stability trend of the dyes were in good agreement with the trend of experimental light fastness values. These disperse dyes possess excellent wash fastness and moderate to good sublimation fastness on hydrophobic substrates.

Applications of natural dye from Ixora coccinea L. in the field of textiles and cosmetics

In the present study an attempt has been made to propose the application of natural dye from Ixora coccinea L., commonly known as Jungle geranium, in the field of textiles and cosmetics. Dyeing with I. coccinea colourant with different combinations of mordants resulted in different shades, such as pink, lilac, and grey shades. The dyed samples were tested according to ISO standard test methods. The samples dyed with combinations of stannous chloride/ferrous sulphate and stannous chloride/ammonium ferrous sulphate were found to have good wash, rubbing, and light fastness properties. Moreover, an effort was made to formulate lip balm. The formulation was evaluated for its stability at 25 and 40 °C for 90 days. The colour of the product was assessed by measuring the L*a*b* values. The product offers excellent properties of smoothness, spreadability, and stability at 25 °C.

Central Composite Design Approach for Optimization of Extraction and Dyeing Conditions of Marigold Colorant

Marigold flowers are used in many Asian countries for various occasions, rituals and offerings. A considerable amount of unused marigold flowers is wasted while the used ones also pose problems in disposing off. Central composite design of experiment was used to optimize the extraction and dyeing conditions of natural dye from marigold flowers. The effect of pH of the extraction medium, extraction time and material to liquor ratio was investigated. It was found that pH and liquor ratio had statistically significant effect on dye extraction, whereas the effect of time, within the range used in this study, was not found to be significant. Optimum dye extraction was obtained in acidic pH of the extraction medium at lower liquor ratio. Temperature and time dyeing are the most influential factors among many other parameters including amount of salt and material-to-liquor ratio. Cotton fabric dyed with the optimized dye extract, showed very good washing and light fastness properties but poor wet crocking fastness.

Extraction of Natural Dye from Ficus cunia and Dyeing of Polyester Cotton and Wool Fabric Using Different Mordants, with Evaluation of Colour Fastness Properties

Due to the various side-effects of synthetic dye, a need has been felt to discover the new dye yielding plants and optimization of various conditions of dyeing. Ficus cunia was proved to be the good dye yielding plant and wide range of color shades were obtained when different mordants were used with different mordanting methods. Leaves of this plant were used for dyeing wool and polyester cotton (PEC) using different mordants, viz. Potassium Aluminium Sulphate, Ferrous Sulphate, Stannous Chloride and Tannic Acid along with one natural mordant. The natural dye extract gave different shades using different natural and synthetic mordants. The washing, rubbing and light fastness properties of dyed samples were assessed and good to excellent fastness grades were obtained.

Dyeing of Carpet Woolen Yarn using Natural Dye from Cochineal

Natural dyes from plant sources are preferred for coloration of woolen textiles and they give dark and dull colors. Development of a woolen carpet with elegant and vivid colors from natural dyes is still scanty. Natural dye from Coccus Cacti called cochineal was extracted by aqueous extraction method and applied on woolen yarn in presence of five different mordants in single and combination forms. Without mordanting, cochineal dye gave bluish purple color and after mordanting, it gave range of colors from scarlet red to black colors on woolen yarn. If two mordants are applied, the final color will depend on the chelating property of dominant mordant. The dominant mordant forms more amount of coordination complex preferentially with the cochineal dye than other mordants. Woolen yarn dyed with cochineal dye in presence of single and dual mordants, showed moderate (grade 3) to very good (grade 4–5) washing fastness and moderate (grade 5) to excellent (grade 7–8) light fastness properties. It is concluded that natural dye extracted from cochineal has potential to produce selective elegant colors on woolen yarn that can improve the aesthetic value of the woolen carpet.

Eco-Friendly Synthesis of Some Thiosemicarbazones and Their Applications as Intermediates for 5-Arylazothiazole Disperse Dyes.

The solid-solid reactions of thiosemicarbazide with 4-formylantipyrine, 2-acetylpyrrole and camphor were performed to afford the thiosemicarbazones 1–3 which underwent hetero-cyclization with phenacyl bromide to furnish the corresponding thiazole derivatives 4–6. The yields of the reactions are quantitative in all cases and the products do not require further purification. A series of 5-arylazo-2-(substituted ylidene-hydrazinyl)-thiazole dyes 7–9 was then prepared by diazo coupling of thiazole derivatives 4–6 with several diazonium chlorides. The synthesized dyes were applied as disperse dyes for dyeing polyester fabric. The dyed fabrics exhibit good washing, perspiration, sublimation and light fastness properties, with little variation in their moderate to good rubbing fastness.

Extraction of juglone from Pterocarya fraxinifolia leaves for dyeing, anti‐fungal finishing, and solar UV protection of wool

In many countries, the search for new sources of natural colourants has recently been intense. This paper deals with the extraction procedure, dyeing behaviour, antifungal activity, and ultraviolet protection of Pterocarya fraxinifolia as a new natural source of dyes. Juglone was found as the main extracted compound after characterisation by ultraviolet‐visible spectrophotometry and Fourier transform infrared spectroscopy. Mordanting and subsequent dyeing of wool with extracted juglone were then performed to study the dyeability and antifungal activities. Three metal salts, aluminium sulfate, copper sulfate, and iron sulfate, were used as chelating materials. The colorimetric properties of samples were evaluated using a reflectance spectrophotometer. Furthermore, the washing and light fastness properties were tested according to ISO 105‐CO3:1989 and ISO 105‐B01:2014. Interestingly, we found P. fraxinifolia to be a source of strong antifungal compounds against microorganisms. Extracted juglone also exhibited strong protection activity against solar ultraviolet rays.

Effect of plasma treatment and grafting of β-cyclodextrin on color properties of wool fabric dyed with Shrimp shell extract

The aim of this study was to evaluate the effect of low temperature plasma (LTP) treatment and grafting of beta-cyclodextrin (β-CD) on dyeing and fastness properties of wool fabrics using natural dye extracted from shrimp shell. Aluminum sulfate, iron sulfate, tin chloride, copper sulfate, and sodium dichromate were used as mordant and the dyeing of samples was conducted after the pre-mordanting process. Scanning electron microscopy and Fourier transform infrared spectroscopy (FTIR) were used to study the morphological and chemical changes of the fibers. Also, the antimicrobial properties of fabrics were quantitatively evaluated against Staphylococcus aureus according to AATCC 100-1993 test method. The results showed using of sodium dichromate as mordant could be attained to green shade after dyeing fabrics. The color difference and color strength of samples were improved by increasing the sodium dichromate concentration and β-CD in the after-treatment process. FTIR analysis indicated a significant increase in the absorption peak of hydroxyl group after grafting of β-CD on LTP-treated samples. Antimicrobial results of samples indicated that LTP-treated fabric demonstrated no antimicrobial behavior, while the dyed and β-CD-grafted sample possessed significant reduction in the number of bacteria. Moreover, the β-CD-treated samples showed very good to excellent light and washing fastness properties.

Salt-free reactive dyeing of betaine-modified cationic cotton fabrics with enhanced dye fixation

Novel cationic cotton fabrics were prepared by an efficient and simple one-step pad–dry–bake pretreatment process with betaine as cationic reagent. Ester bonds formed between cotton fibers and betaine hydrochloride were proved by Fourier transformed infrared attenuated total reflection (FTIR-ATR) spectra. Moreover, the properties of the cationic fabrics, including X-ray Diffraction (XRD), tensile strength and whiteness and yellowness index, were investigated in comparison with that of the untreated ones. The cationic fabrics were applied in salt-free dyeing of C.I. Reactive Red 195, C.I. Reactive Yellow 145 and C.I. Reactive Blue 19. Different dye fixation processes were applied and compared for untreated and cationic cotton. Dye fixation and color fastness properties of the dyes were tested, and the results presented that dye fixation on the cationic fabrics in the absence of salt was improved with satisfactory light fastness property and applicable wash and rub fastnesses.