High Light Fastness Research Articles

Enhancing color brilliance and fastness of polyester dyeing with antipyrine-derived disperse dyes

Disperse azo dyes are important colorants for dyeing polyester fabrics, but developing optimized disperse azo dyes remains a challenge. This work details the synthesis of seven new disperse azo dyes 3a-g derived from the coupling reaction of 4-aminoantipyrine diazonium salt with various phenolic precursors including phenol (3a), salicylic acid (3b), salicylaldehyde (3c), cresols (3d-f), and resorcinol (3g). The dyes were characterized by spectroscopic techniques. Their UV–visible absorption spectra were studied, revealing bathochromic shifts for 3d-g containing electron-donating methyl and hydroxyl substituents compared to parent dye 3a while dyes 3b-c showed hypsochromic shifts. The impact of acid and base on the absorption spectra indicates azo-hydrazone tautomerism for 3f-g but predominant azo form for 3a-e. The dyes showed excellent dyeing on polyester fabrics with up to 97.86 % dye exhaustion. High wash, light and perspiration fastness was exhibited while fastness to respiration varied. The strongest color yield on polyester was achieved with 3g derived from resorcinol coupler. Density functional theory calculations were performed to elucidate relationships between substituent effects and spectral attributes. Lower energy gaps were computed for 3f-g, consistent with enhanced reactivity. This work expands disperse azo dye precursors while offering fundamental structure-performance insight to guide future design. The potent polyester coloration and good fastness properties warrant ongoing investigation of these dyes.

Dyeing of Cotton and Wool Fibers with the Aqueous Extract of Alnus glutinosa: Evaluation of Their Ultraviolet Protection Factor, Their Color fastness and the Antioxidant Activity of the Aqueous Extract

The aim of the present study is to evaluate the dyeing properties and behavior of the aqueous extract of Alnus glutinosa leaves when applied on cotton and wool fibers. The antioxidant activity and the total phenolic content of the aqueous extract were calculated. The colorfastness of the dyed samples such as washing, acid and alkali perspiration, wet and dry fastness and light fastness was performed. The ultraviolet protection factor (UPF) which is a measurement of the protection offered by the dyed fabric substrates against ultraviolet radiation was also assessed. It was found that Alnus glutinosa aqueous extract shows exceptionally high antioxidant activity and high phenolic content. The dyed samples showed astonishingly high light fastness approaching the light fastness of synthetic dyes such as the vat dyes or metal complex dyes. The conferred protection of the dyed samples against the distractive ultraviolet radiation is exceptionally high as this is demonstrated by the high UPF measurements of the dyed samples.

Bioactive and Multifunctional Wool Textiles Finishing with Diospyros mollis Griff. Extract

Due to the sudden pandemic outbreak, there is a substantial demand for antimicrobial textiles for health and hygiene. Natural dyeing with plant sources has been proven to be an excellent eco-friendly method for producing healthcare textiles. In this study, Diospyros mollis Griff. extract was applied to the simultaneous dyeing and multi-functionalization (antibacterial activity and UV-protection) of wool fabrics. Response surface methodology was applied to optimize the treatment procedure and assess parameter interactions. The optimal result was achieved when dyeing at pH 4, dye concentration 25 g/L, temperature 88°C, and time 95 min. The dyed fabrics had good antibacterial activity against both E.coli and S.aureus (bacterial colony reduction > 90%), with E.coli being more pronounced. The UV protection factor (UPF) also reached the maximum (40+) level, demonstrating their superior UV protection. The finished wools are black, with high color strength (K/S > 9), good light and washing fastness, and fair to good crocking fastness. Thus, Diospyros mollis Griff. fruit extract can be used as a new bioactive agent for multifunctional textiles, as well as simultaneous black coloring.

Synthesis, recovery, and application of environmentally friendly disperse dyes with high light fastness

Dye wastewater has attracted great attention due to high pollution and toxicity which can cause harm to the living environment. It is common for azo-disperse dyes to be used to dye hydrophobic fibers. A reduction clearing method is used to eliminate the dye particles on the fabric after dyeing. However, when azo disperse dyes on the fiber surface are eliminated by the reduction clearing process, this can give rise to an effluent discharge due to the presence of sodium hydrosulfite. The introduction of carboxylic ester groups into dye molecules can effectively avoid this issue. Six novel environmentally friendly alkali-clearable disperse dyes, containing cyano and carboxylic ester groups, were readily synthesized by a diazo coupling reaction with various diazo components. Their dyeing properties on polyethylene terephthalate fabrics were respectively measured and compared with those of commercial reference dyes. It was indicated that some fastness properties of the synthesized dyes on polyethylene terephthalate fabrics after the alkali clearing were improved compared with those of the reference dyes due to the existence of the carboxylic ester group. Moreover, the chromaticity of dye wastewater can be further reduced by recovering hydrolyzed dyes.

Photostability of Mannich‐type dyed silk fibroin with pyrazolone‐containing aromatic primary amine dyes

AbstractMannich‐type dyeing of silk fibroin with aromatic primary amine dyes (APADs) is a novel reactive dyeing method that requires mild conditions and exhibits high selectivity and good wet fastness. However, the primary amine group in the APADs significantly decreases the photostability of Mannich‐type dyed silk fabrics. To reveal the structure–activity relationship and photofading mechanism of the APADs by Mannich‐type dyeing, six pyrazolone‐containing APADs with similar structures were designed and synthesised. Variation in amino electron density among the dye analogues was related to differences in colour fixation of the Mannich‐dyed fabrics, as determined from the calculated Mulliken charge densities. Using mass spectrometry to monitor the photodecomposition of the dyed silk, it is demonstrated that the Mannich‐type dyed silk fabrics undergo photooxidative fading, in contrast to the conventional acidic‐type dyed fabrics that undergo photoreductive fading. Furthermore, it is shown that the Mannich‐type dyed silk fabric has a higher light fastness than conventional acidic‐type dyed fabrics using the same pyrazolone‐containing APADs. Evaluation of dye dipole moment and Mannich‐type dyeing shows that the APADs with increased dipole moments generally demonstrated increased light fastness.

Effect of isoindole derivative pigments with planar macroconjugated structure on the UV resistance of HDPE

Different colors of high-density polyethylene (HDPE) natural gas pipelines, water supply pipelines, geomembranes in small communities, garden agriculture, and large factories, play a differentiation, warning, decorative aesthetic, and other aspects of the role. However, little research has been done on HDPE that can be used for long periods and in a variety of colors other than black and white. Phthalocyanine pigments with a large planar conjugate structure are often used in modern artists' paints because of their good stability and are hopeful for use in HDPE. For this reason, in this paper, phthalocyanine blue with a high lightfastness rating was selected. Pure HDPE and HDPE with pigment were compared by color difference, carbonyl index (CI), mechanical properties, and thermomechanical properties before and after UV irradiation. After irradiation for 2000 h, the latter not only did not fade easily but also maintained 82 % elongation at break. At the same time, the carbonyl index was much lower, representing the addition of pigments to inhibit the photo-aging process. Hindered amine light stabilizers (HALS) were also added to the matrix to further improve the ultraviolet (UV) stability along with ultraviolet light absorber (UVA). Addition of HALS and pigments had a positive effect on the UV stability of HDPE, but the excess of HALS had a negative effect on color stability, dispensability and tensile strength. Addition of UVA had little effect on HDPE/Blue/HALS. Finally, the mechanism of the phthalocyanine blue pigment in improving the light aging resistance of HDPE was investigated by ultraviolet spectroscopy. HDPE/Blue/HALS prepared in this work had a low CI and high elongation at break of all formulations at 2000 h of irradiation, indicating that it maintains good performance over a long period of time. The low color change and dispersion uniformity of that under prolonged irradiation met the long-term aesthetic needs of HDPE.

Syntheses and dyeing properties of novel water‐soluble reactive sulphur black dyes

AbstractThe practical application of a sulphur black dye relies on its ability to dye cotton fibres with pure black colour and maintain the colour with high light fastness. Here, we report a synthesis method to prepare a novel water‐soluble reactive sulphur black dye. The approach involves the reduction of CI Sulphur Black 1 to its leuco form and subsequent reaction with a water‐soluble intermediate containing reactive groups synthesised from amino acid and cyanuric chloride. The optimal carboxyl and reactive group content of the water‐soluble reactive sulphur black dye is 141 mmol/100 g, and the water solubility can reach 92 g/L. The fixation of the reactive sulphur black dye on cotton reaches 89% in a pad dyeing process without using sodium sulphate. The reactive sulphur black dye can achieve a light fastness of grade 6‐7, a dry rub fastness of grade 4 and a wet rub fastness of grade 2, comparable or higher than the conventional CI Sulphur Black 1. The dyeing results showed that the novel water‐soluble reactive sulphur black dye has excellent performance and good application prospects.

Application of some novel pyrazole disperse dyes to synthetic fabrics

In this study, 8 novel pyrazole disperse dyes which were synthesized in our previous work [1] were applied to polyethylene terephthalate (PET), poly (lactic acid) (PLA) and polyamide 6.6 (PA 6.6) fiber fabrics and their colorimetric and fastness properties were evaluated. The measured a*, b* and hue angle (ho) values of all dyed fabrics exhibited yellow, orange and red colour shades. Quite high colour strength values (K/S) were measured particularly for dyes containing substitute groups; p-OCH3 and o-OCH3. Shade changes of all fabrics after standard washing and sublimation tests were in the commercially adequate range. All dyed PET, PLA and PA 6.6 fabrics exhibited commercially acceptable fastness staining performances with very good to excellent levels. Synthesized novel disperse dyestuffs led to moderate to high light fastness levels particularly in the case of PLA and PET fabrics.

Facile Synthesis of Novel Disperse Dyes for Dyeing Polyester Fabrics: Demonstrating Their Potential Biological Activities.

Original work showed the composition of the dyes and the antimicrobial/UV protective properties of a series of dyes obtained in our laboratories over the past twelve years in an easy way using microwave technology and their comparisons with conventional methods. The results we obtained clearly indicated that by using the microwave strategy, we were able to synthesize the new disperse dyes in minutes and with a much higher productivity when compared to the traditional methods, which took a much longer time, sometimes up to hours. We also introduced ultrasonic technology in dyeing polyester fabrics at 80 °C for an environmentally friendly approach, which was an alternative to traditional dyeing methods at 100 °C; we obtained a much higher color depth than traditional dyeing methods reaching 102.9%. We presented both the biological activity of the prepared new dyes and the fastness properties and clearly indicated that these dyes possess biological activity and high fastness properties.We presented through the results that when dyeing polyester fabrics with some selected disperse dyes, the color strength of polyester fabrics dyed at high temperatures was greater than the color strength of polyester fabrics dyed at low temperatures by 144%, 186%, 265% and 309%. Finally, we presented that a ZnO or TiO2 NPs post-dyeing treatment of polyester fabrics is promising strategy for producing polyester fabrics possess multifunction like self-cleaning property, high light fastness, antimicrobial and anti-ultraviolet properties.

Synthesis and properties of poly(styrene‐co‐maleic acid) macromolecular reactive dyes

AbstractTo obtain a new type of macromolecular reactive dye with high fixation and good light fastness, poly(styrene‐co‐maleic acid) was synthesised by co‐polymerisation of styrene and maleic anhydride, then, through nitration, reduction, diazotisation and coupling reaction, novel macromolecular reactive dyes were prepared with a solubility greater than 60 g/L. The dyes were used to dye cotton fabrics; the results showed their fixation was more than 92%, and both the rub and wash fastness of the dyes were good. The light fastness of the red and blue dyes with the ethoxy group on melamine was grade 4, and for the yellow dye reached grade 5. The poly(styrene‐co‐maleic acid) macromolecular reactive dyes exhibit very good application prospects in practice.

Noninvasive identification of turmeric and saffron dyes in proteinaceous textile fibres using Raman spectroscopy and multivariate analysis

AbstractWe used Raman spectroscopy combined with multivariate analysis to study noninvasively naturally and artificially aged samples of silk and wool fibres dyed with turmeric and saffron dyes, following historical recipes. The Raman spectra obtained from all the samples using the two excitation lasers (785 and 1064 nm) showed the characteristic peaks of each dye and fibre. The 1064‐nm macro FT‐Raman offered more information regarding the degradation of the fibre substrate, whereas the μ‐Raman at 785‐nm spectra proved more suitable in the identification of dye characteristic peaks. We also performed colorimetric measurements to evaluate the colour change upon artificial ageing and compared them with the information obtained with Raman spectroscopy. The results suggest saffron has a higher lightfastness than turmeric and that silk fibres suffer higher fading and more evident degradation than wool. Raman spectroscopy informs about the chemical composition of the colourants and fibres and their changes upon ageing without sample pretreatment. Finally, we analysed a historical wool sample coming from a 19th‐century Persian carpet, and we identified turmeric.

Color, Fastness, Antibacterial, and Skin Sensitivity Properties of High Lightfastness Azo Disperse Dyes Incorporating Sulfamide Groups

A series of cationic and disperse dyes has been applied on to the nylon and acrylic fabrics in order for their dyeing properties to be investigated. The build-up values and the fastness properties of the dyed fabrics such as wash, light, and rubbing fastness degrees were measured by standard methods. Moreover, the color gamut of the synthesized dyes was measured on polyamide and acrylic fibers. The results showed that the synthesized dyes were able to dye polyamide fabrics with deep shades. However, synthesized azo dyes did not show good dyeing ability on acrylic fiber. The antimicrobial properties of dyed polyamide fabrics were evaluated against various bacteria and fungi. The dyed fabrics exhibited excellent antimicrobial efficacy against both Gram-positive, Gram-negative bacteria, and fungi. The skin irritation test on azo dyes and dyed polyamide fibers with this dye was carried out. The results showed that none of the dye and dyed polyamide fibers created any skin irritation.

Synthesis and application of poly(vinylamine-co-acrylic acid) macromolecule dyes with high light fastness

New types of poly(vinylamine-co-acrylic acid) macromolecule dyes were designed and synthesized based on poly(vinylamine-co-acrylic acid) and reactive dyes. The structures of the synthesized dyes were characterized by ultraviolet-visible spectroscopy, infrared spectroscopy, proton nuclear magnetic resonance and thin layer chromatography. They were applied for dyeing cotton fibers and high fixations were achieved due to their reactive abilities. The dyed samples showed excellent fastness to washing and rubbing and the light fastness of red, blue and yellow poly(vinylamine-co-acrylic acid) dye could reach grades 3–4, 4 and 6–7, respectively.

High Lightfastness Acid Dyes Synthesized from Corresponding Anthraquinone Chromophore Utilizing a Sulfonation Reaction Part 2: Dyeing Properties on Polyamide and m-Aramid Fibers and Fastness

This study aimed at investigating the dyeability of synthesized acid dyes on fine nylon and m-aramid and their light fastness. A sulfonic acid group was introduced into the corresponding hydrophobic dye, which has an anthraquinone structure, to allow dyeing capabilities through ionic bonding with the nylon and m-aramid. Dyeability on fine nylon and m-aramid was mainly evaluated by the UV-Vis absorbance at maximum absorption wavelength (λmax). As the dyeing temperature increased to 110°C, the exhaustion rate of synthesized acid dyes increased. The synthesized acid dyes showed higher adsorption rates when dyeing occurred at high temperature. For fine nylon, as the synthesized acid dye concentration increased, the K/S value increased to 2.5 % o.w.f. and remained at that level thereafter. The fastness of light, wash, rubbing, and perspiration of fine nylon fabric dyed at these optimum conditions had higher ratings than those of commercial acid dyes. Regarding m-aramid dyeing, the grade of light fastness was higher than that of the commercial basic dye.

A new way to improve the light-fastness of azo reactive dyes through the introduction of benzene sulfonamide derivatives into the triazine ring.

Herein, a new kind of hetero-bifunctional reactive dyes with high light-fastness was designed and synthesized by introducing benzene sulfonamide and its derivatives into the triazine ring. Benzene sulfonamide or its derivatives and 2-amino-5-naphthol-7-sulfonic acid (J-acid) were condensed with cyanuric chloride to synthesize coupling components, which were then coupled with the diazo salt of 4-(β-sulfatoethylsulfonyl)aniline. The dyes were characterized by IR spectroscopy and MS. The color fastness test proved that the light-fastness of the dyes could be improved by 1 grade via the introduction of benzene sulfonamide derivatives into the triazine ring when compared with the case of the control dyes. Fluorescence spectra demonstrated that after the introduction of benzene sulfonamide derivatives, the dye molecule could return to the ground state from the excited state and emit fluorescence; in addition, the introduced benzene sulfonamide derivatives helped to deteriorate the adverse effect of UV light on the dye. Moreover, the dyeing results showed that the dyes containing the sulfonamide groups had equal dyeing properties when compared with that of the control dyes.

High Light-Fastness Acid Dyes Synthesized from Corresponding Anthraquinone Chromophore Utilizing a Sulfonation Reaction. I. Dye Synthesis and Characterization

As the diameter of polyamide fibers decreased to finer denier, the dyeing fastness tends to be deteriorated due to the increase of their surface area, particularly both light fastness and wash fastness. In this study, three acid dyes were synthesized utilizing a sulfonation reaction starting from corresponding hydrophobic dye (for yellow and red dye) and dye intermediate containing a sulfonic acid group (for blue dye), those featured by high light fastness property. A Gaussian structural prediction model was used to determine the structure of the acid dyes prior to dye synthesis, and the optimal structures of three acid dyes were analyzed. Dye structures prepared were confirmed by 1H-NMR, mass spectroscopy, and elemental analysis. By using a UV-vis spectrophotometer, the absorption maxima and molar extinction coefficient were also measured for three acid dyes comparing to that of the corresponding disperse dye or blue dye intermediate. Judging from spectroscopic data, the introduction of sulfonyl groups led to increase of molar extinction coefficient and a bathochromic shift.

Light fastness of printing inks: a review

Light fastness, in its broadest sense, is the resistance of colours to fading un-der the influence of a light source. Light fastness is one of the most important physical, and therefore visual, properties sought in both pigments and in the inks. Artificial and natural light causes most pigments to fade resulting in co-lour change. The light fastness of inks is important especially in the packag-ing and advertising industries. The posters and advertisements hung on the billboards used especially in outdoor advertising, printed product packaging and other printed products exposed to sunlight require high degree of light fastness. In this study, light fastness and factors affecting the resistance of the colour to the light were investigated and suggestions were made regard-ing high light fastness in terms of printability.

Structural coloration of chitosan coated cellulose fabrics by electrostatic self-assembled poly (styrene-methyl methacrylate-acrylic acid) photonic crystals

The structural coloration of a chitosan-coated woven cotton fabric obtained by glutaraldehyde-stabilized deposition of electrostatic self-assembled monodisperse and spherically uniform (250 nm) poly (styrene-methyl methacrylate-acrylic acid) photonic crystal nanospheres (P(St-MMA-AA)) was investigated. Bright iridescent coatings displaying different colors in function of the viewing angle were obtained. The SEM, diffuse reflectance spectroscopy, TGA, DSC and FTIR analyses confirm the presence of structural color and the glutaraldehyde and chitosan ability to provide durable chemical bonding between cotton fabric and photonic crystal (PCs) coating with the highest degradation temperature and the lowest enthalpy. The coatings are characterized by a mixture of face-centered cubic and hexagonal close-packed arrays alternating random packing regions. For the first time a cost-efficient structural coloration with high washing and light fastness using self-assembled P(St-MMA-AA) photonic crystals was successfully developed onto woven cotton fabric using chitosan and/or glutaraldehyde as stabilizing agent opening new strategies for the development of dye-free coloration of textiles.

Synthetic Fiber Dyeing with New Pyrazole Disperse Dyes and Their Colorimetric and Fastness Properties

A series of disazo pyrazole disperse dyes were synthesized and reported at our previous work. These 8 synthesized disazo pyrazole disperse dyes (3a-3h) were applied to poly(lactic acid) (PLA), poly(ethylene terephthalate) (PET), and polyamide 6.6 fibers. Their colorimetric and color fastness properties were investigated. All studied fibers dyed with these synthesized dyes exhibited yellow-red shades. 3c (p-Cl), 3e (m-Cl), and 3h (o-Cl) disazo disperse dyes, having auxochrome -Cl, led to the lowest color yield values for all three studied fibers. The same dyes resulted in higher color strength with darker shades on the PET and PLA fabrics in comparison PA 6.6 fabrics. 3a (p-NO2), 3b (p-OCH3), 3d (m-NO2), 3f (o-NO2), and 3g (o-OCH3) disazo disperse dyes can be recommended for PLA and PET dyeing from the color point of view leading to medium to heavy depth of shades. The wash, alkaline and acidic perspiration, dry and wet rub, water and sea water fastness levels of PLA, PET, and PA 6.6 samples dyed with 3a-3h dyes were generally quite high and in the commercially acceptable range with few exceptions. Dyed PLA fabrics displayed better sublimation fastness levels than dyed PET and PA 6.6 fabrics. Synthesized disperse dyes resulted in high light fastness performance on especially PET and PLA fibers. Light fastness level was better for dyed PET samples by comparison with dyed PLA and PA 6.6 fabrics.

Alternative plants to be used in natural dyeing on wool yarn fibers

ABSTRACTIn this study, 28 plants were collected from nature and the extracts were obtained with and without mordants from these plants. The wool yarns (3.5 N m natural wool carpet yarns obtained from the natural fibers 60 s, 23.3 µm, 10−4 cm) were colored by each of these extracts and the light and abrasion fastness of obtained colored substances of various colors were determined. While the plant showing the highest light fastness was walnut tree leaf (Juglans regia), the plant showing the highest abrasion fastness was determined as quince leaf (Cydonia oblonga). On the other hand, while the ferric sulfate as a mordant provided the highest light fastness, the highest abrasion fastness was obtained from the experimental group to which mordant was not applied.