Improvement of the light fastness of natural dyes: the action of singlet oxygen quenchers on the photofading of red carthamin

While the contribution of singlet oxygen quenchers to synthetic dyes has been investigated previously by several workers, there have been few studies pertaining to the use of singlet oxygen quenchers as a means of improving the light fastness of natural dyes. In this paper, the influence of various additives on the photofading of carthamin has been examined in cellulose acetate film. The rate of photofading of the colour was remarkably suppressed in the presence of nickel hydroxyarylsulphonates, while the addition of UV absorbers afforded little retardation in the rate of fading.     

Improving light fastness of natural dyes on cotton yarn

The objectives of this study were to evaluate the light fastness of selected natural dyes (madder, weld and woad) and the effect of some commonly used antioxidants and UV absorbers on the light fastness of these dyes.

The photofading rate curves of madder and weld fixed on cotton correspond to type II fading rate curves described by Giles. These results are in concordance with those of Cox-Crews. The woad presents a type III fading rate curve, similar to the indigo fading rate curve presented by Cox-Crews.

A poor light fastness of the three natural dyes in comparison with synthetic ones is established beyond question. Nevertheless, the use of some additives can improve this default of natural dyes. In all the cases, the use of UV absorbers or antioxidants improved the light fastness of dyed fabrics. The most effectives were the vitamin C and the gallic acid.     

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.     

Effect of stabilisers containing a singlet oxygen quencher on the photofading of dyes in a polymeric substrate

New ultraviolet absorbers and phenolic antioxidants bearing a nickel carboxylate group have been prepared and their ultraviolet–visible absorption spectra measured in ethanol. Their inhibiting effect on the fading of dyes was examined in cellulose acetate film. It has been found that the presence of a simple ultraviolet absorber or phenolic antioxidant is not of particular value in improving the light fastness of dyes. The introduction of a singlet oxygen-quenching group into an ultraviolet absorber can however have an important effect. The nickel complex of salicylic acid salicylate was very effective in reducing the rate of photofading.     

Photofading of reactive dyes on silk and cotton: effect of dye—fibre interactions

Fading characteristics of selected bifunctional and monofunctional reactive dyes have been studied on silk and cotton. Dyes were applied in the reactive and hydrolysed forms in order to study the influence of covalent bonding on the photofading of reactive dyes. The active dye-fibre interaction was found to influence the light fastness of dyes. Reactive dyes forming covalent bonds exhibited better fastness especially on cotton. Only a slight difference in light fastness of fixed and unfixed dyes was observed in the case of silk. The bifunctional reactive dyes, due to the formation of crosslinks, maintain the integrity of the fibre particularly for short periods of light exposure.     

Textile applications of photochromic dyes. Part 3: factors affecting the technical performance of textiles screen‐printed with commercial photochromic dyes

The technical performance of five selected commercial photochromic dyes applied by screen‐printing on textiles was evaluated using a colour measurement methodology that has previously been established and validated. The results of wash fastness assessments were distinctly unusual. With the selected spirooxazine dyes, the degree of photocoloration increased with initial washing and decreased with subsequent washings, while the naphthopyrans behaved more normally, showing a consistent marginal decrease in photocoloration with repeated washing. An explanation is proposed consistent with scanning electron microscopy examination of the binder film degradation and with the structural differences between the dye classes. The dyes in this application showed limited photostability. The incorporation of ultraviolet absorbers was found to increase photostability only to an extent specific to particular ultraviolet absorber/dye combinations. However, the presence of the ultraviolet absorber led to a consistent reduction in the degree of photocoloration of the dyes. In contrast, the incorporation of hindered amine light stabilisers significantly enhanced the photostability of the dyes, providing an increase in resistance to photodegradation of up to fivefold.     

Improving the light fastness of dyed nylon fabrics using nickel arylsulphonates

Various nickel arylsulphonates were synthesised and their protecting effects on the photofading of CI Basic Violet 3, CI Acid Red 94, CI Acid Red 87 and CI Acid Blue 74 examined on nylon fabric. The rates of photofading of the dyes were remarkably suppressed in the presence of nickel salts, while the addition of ultraviolet absorbers and conventional stabilisers afforded little retardation of the rate of fading. The antimicrobial activity against two species bacteria of nickel salts was also examined. This aftertreatment technique was shown to be safe for the environment and human health.     

Photodegradation of some 1:2 metal-complexed formazan dyes in an amide environment

The photodegradation of some representative metallised formazan dyes has been investigated. Photofading was examined in NN-dimethylformamide (DMF) at wavelengths of 300 and 350 nm, and in daylight. The measured quantum yield of photodegradation depended on the metal present in the dye molecule and the photoysis wavelength. It was found that with UV light under anerobic conditions the presence of ketone sensitisers such as benzophenone accelerated photofading, confirming that hydrogen abstraction is responsible for degradation. Oxygen also played an important role in the photolytic behaviour under daylight exposure conditions. Co(III) complexed formazan dyes, unlike their Fe(III) analogues, were found to be effective singlet oxygen quenchers. Photofading of the metallised formazan dyes on polyamide fabric was also examined. Fading rates were directly related to the reciprocal of the light fastness of polyamide dyeings. The expected direct relationship between log quantum yield and the reciprocal of light fastness was also observed.     

UV absorber aftertreatment to improve lightfastness of natural dyes on protein fibres

The effect of a UV absorber on the lightfastness of natural dyes has been investigated. Wool and silk fabrics, dyed with natural dyes with or without mordants, were aftertreated with two UV absorbers. This treatment improved the lightfastness of the mordant-dyed fabric without affecting its colour or shade. The extent of photofading was evaluated by measuring the colour difference, Δ E , of the dyed sample before and after a 20 h period of irradiation under a xenon arc lamp. The uptake of the UV absorber on wool was much higher than that on silk.     

有机染料光褪色机理及主要原因

本文综述了有机染料光褪色机理的主要研究方法以及现有研究结论．对光氧化和光还原过程、影响因素、典型反应步骤、研究手段进行了系统的阐述，同时也对通过染料分子结构设计合成、通过添加剂的使用提高染料光牢度的方法进行了介绍．     

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.     

The effect of polycation on the light fastness of CI Acid Red 249

Cationic compounds are frequently used in direct dyeing processes and in ink-jet printing as dyefixing agents. In some cases, however, they can reduce the light fastness of dyes used. This report deals with the effect of a polycationic compound, Polyfix 601, on the light fastness of CI Acid Red 249, an anionic 2-phenylazo-1-naphthol dye, in aqueous solutions and in PVA films. As a comparison, the much smaller ammonium cation was used, which had no observable effect on hue or dye light fastness. However, some changes to the dye's physical properties were observed. The effect of the polycation is explained as a consequence of dye aggregation, facilitated by presence of polycation. Self-sensitised singlet oxygen seemed to play no part in dye photofading, but other oxygen species could participate in the process.     

Effect of uv absorbers containing singlet oxygen quenching groups on the photochemical stability of crystal violet lactone and related colours

The photofading behaviour of Crystal Violet Lactone was investigated in solution. The contribution of singlet oxygen to that fading was suggested. UV absorbers containing nickel sulphonate quenching groups were prepared and the protecting effect of these compounds towards the photofading of colour materials derived from colour formers was examined in solution and in solid state. It was proposed that nickel salts of 2,2′-dihydroxy-4,4′-dimethoxybenzophenone-5-sulphonic acid and its derivative can be applied as effective stabilisers against the photofading of indicator dyes in pressure (or heat) sensitive recording systems.     

Light fastness of naturally occurring anthraquinone dyes on nylon

Nylon fabric has been dyed with two purified components of Indian madder, purpurin (1,2,4-trihydroxyanthraquinone) and munjistin (1,3-dihydroxy-2-carboxyanthraquinone). The light and wash fastness of dyed and mordanted samples has been studied. Purpurin showed much better resistance to photofading than munjistin. It was found that the type of mordant and the method of mordanting significantly affected the rate and extent of photofading. The use of copper or ferrous sulphate gave high resistance to fading, whereas stannous chloride or alum did not. On the other hand, light fastness was improved when postmordanting was conducted with copper or ferrous iron, but pre-mordanting was superior in the case of stannous chloride or alum.     

The influence of a polymer substrate on the light fastness and isomerisation of some azo dyes

Poly(ethylene terephthalate) films having different morphologies have been coloured with some azo dyes. Isotropic and anisotropic films showed an inversion in dyeing behaviour as well as in light fastness, always at crystallinity β=0.5. We have interpreted the phenomenon in terms of a different localisation of the dye in going from a structure of PET corresponding to a free-volume model to a structure corresponding to a pore model. It was found that polymer morphology strongly affected dye photofading whilst the thermal cis-trans isomerisation of azo dyes in the PET matrix depended only on the amorphous region; below the glass transition temperature isomerisation proceeded in a way that was determined by the effects of restrictions in the mobility of the photochrome itself.     

Ink‐jet printing of cotton with natural dyes

Four natural dyes, annatto, cutch, pomegranate fruit rind, and golden dock, were used as colorants for the preparation of water‐based ink‐jet inks for digital textile printing. The physical and rheological properties (pH, conductivity, surface tension, and viscosity) of the inks were measured over a period of 90 days for the evaluation of ink stability and suitability for ink‐jet printing. The inks were found to be suitable and were used for the digital printing of cotton fabrics. The prints were subjected to wash, light, and rub fastness tests and colour measurements. Colour consistency and fastness results, especially after fixation, are comparable with those of synthetic dyes, which paves the way for the production of environmentally friendly ink‐jet inks using natural dyes for the digital printing of cotton through the formulation of suitable printing techniques.     

Improving transfer printing and ultraviolet‐blocking properties of polyester‐based textiles using MCT‐β‐CD,chitosan and ethylenediamine

This study demonstrates the possibility of improving the transfer printability and fastness properties, as well as the ultraviolet‐protecting functionality, of polyester, polyester/wool, polyester/cotton and polyester/viscose woven fabrics via pretreatment with monochlorotriazinyl β‐cyclodextrin (MCT‐β‐CD), chitosan or ethylenediamine, followed by subsequent transfer printing with sublimable disperse dyes. The modification variables as well as the transfer printing conditions were optimised. The experimental results reveal that generating hydrophobic cavities (via grafting of β‐CD) at the fabric surface, fixing of chitosan, with its amino groups, onto the finish/fabric matrix, or introducing amine functional groups, via aminolysis of the polyester component, results in obtaining transfer printed fabric samples with darker depth of shades and better fastness properties, as well as with higher ultraviolet‐protecting functions. It was further noted that, in all cases, the enhancement in the imparted properties is governed by type of substrate, kind and extent of chemical modification, affinity for the sublimable disperse dyes, accessibility of generated hosting and fixing sites, as well as the ultraviolet‐blocking capacities of the modified/post‐printed substrates against damaging ultraviolet rays. The mode of interaction, as well as the surface morphology of some non‐treated and treated fabric samples, was also investigated.     

Technical properties and photofading of disperse heterocyclic azo dyes

A series of heter acyclic azo dyes derived from aminophenyl-benzothiazoles and substituted dialkylanilines was prepared and tested on polyamide and polyester. The overall properties were satisfactory and compared favourably with related dyes previously described.

Several correlations between structure and physical, spectroscopic (VIS and NMR) and fastness properties were found. An investigation of the photofading of the dyes on substrates as a function of time, checked with colourimetric techniques, proved a close time-dependent feature for colour parameters.     

Role of quaternary ammonium salts in improving the fastness properties of anionic dyes on cellulose fibres

The object of this study was to review the developments taking place during 1990–2005 regarding the use of quaternary ammonium salts as dye fixing agents for improving the fastness properties of anionic dyes on cellulose fibres. As far as fastness properties are concerned, this review is restricted only to fastness to light, washing and water treatments.     

偶氮染料结构与日晒牢度关系研究

本文介绍了近年来国内外对于偶氮染料光致褪色的研究进展,综述了偶氮染料光褪色与偶氮键断裂机理。利用Hammett方程,反映出取代基效应与染料褪色速率间的定量关系,并将Hammett方程引入分散、酸性偶氮染料日晒牢度的分析中,很好的阐释了取代基团吸、供电子效应对染料在不同纤维上日晒牢度的影响,并提出了获得优异日晒牢度染料的合成和应用方法。