Textile applications of photochromic dyes. Part 2: factors affecting the photocoloration of textiles screen‐printed with commercial photochromic dyes

The performance of five commercial photochromic dyes applied by screen printing on textiles was evaluated using a colour measurement methodology which has previously been established and validated. Printing as disperse dyes on polyester gives the strongest photochromic effect when the dye is located near the surface. However, the dyes are applied more effectively using an adaptation of a pigment printing method. Several factors influencing the photochromic properties of the printed textiles were evaluated. The ultraviolet reflecting properties of cotton give a higher level of photocoloration than on polyester. In the dyes studied, the spirooxazines show slightly faster colour development and fade much more rapidly than the naphthopyrans, and the latter show a residual colour after fading. The effect of the ultraviolet irradiation wavelength profile on the photochromic response may be correlated with the ultraviolet absorption spectra of the dyes.     

Textile applications of photochromic dyes. Part 4: application of commercial photochromic dyes as disperse dyes to polyester by exhaust dyeing

A series of commercial photochromic dyes was applied to polyester fabric as disperse dyes. The photocoloration properties of the dyed fabrics were investigated by applying techniques previously established in our laboratories using an independent source of ultraviolet irradiation and traditional colour measurement instrumentation. The dyed fabrics showed reversible photochromism, developing pronounced colours from weak background colours on irradiation with ultraviolet light and returning to their original state when the ultraviolet light source was removed. However, the extent of photocoloration and the depth of background colour varied significantly with the particular dye used. The dyeing procedure was optimised by maximising the degree of photocoloration, expressed as the colour difference (ΔE₁) between the colour developed after ultraviolet exposure and background colour, while minimising the background colour, expressed as the colour difference (ΔE₂) between unexposed dyed and undyed fabrics. Optimum dyeing concentrations were determined. The colour development and fading properties, fatigue resistance and storage stability of the dyed fabrics were investigated.     

Direct coloration of textiles with photochromic dyes. Part 2: The effect of solvents on the colour change of photochromic textiles†

Polyester, acrylic and nylon textile substrates dyed with two spirooxazine dyes, 1,3,3‐trimethyl‐spiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1a ) and 6′‐piperidino‐1,3,3‐trimethyl spiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1b ), exhibit significantly higher photochromic colour build‐up when wet compared with after drying. A study of this phenomenon, extended beyond water to the influence of a series of selected organic solvents on photochromic behaviour, using colour measurement of the photochromic textiles under controlled ultraviolet irradiation conditions, is reported. The results of molecular modelling calculations (AM1 in water and PM5 in water) have been used as a means of interpreting the observed effects, in conjunction with qualitative arguments based on solvation and fibre swelling.     

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester,nylon and acrylic fabrics†

1,3,3‐Trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1a ) and 6′‐piperidino‐1,3,3‐trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine ( 1b ) were applied as disperse dyes to polyester, nylon and acrylic fabrics. Under optimised dyeing conditions, photochromic fabrics were produced which, on irradiation with ultraviolet or exposure to sunlight, turned blue ( 1a) or blueish‐purple ( 1b ). Dye 1a showed enhanced photochromic colour change performance compared with dye 1b . The photochromic colour build was highest on nylon and lowest on acrylic fabric. The colour change properties and the technical performance (wash fastness and photostability) of the photochromic fabrics were evaluated using specifically adapted colour measurement methods. The data were analysed in terms of variation of lightness, a*, b*, chroma, hue angle and ΔE, colour difference before and after exposure, and K/S curves as a function of irradiation time. The fabrics generally showed good wash fastness. Although the colour build‐up decreased with exposure to the Xenotest fadeometer, some residual photochromism remained after prolonged 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.     

Anionic coloration of acrylic fibre. Part 1: Efficient pretreatment and dyeing with acid dyes

Anionic dyeable acrylic fibre has been obtained by a viable and efficient pretreatment process using hydroxylamine hydrochloride in the presence of acetate salt. The chemical modification relies on an amidoximation reaction that partially converts cyano groups present in the fibre to amidoxime groups. Different factors that may affect the pretreatment process have been investigated. The pretreated fabrics were dyed with CI Acid Red 1 and CI Acid Green 16 and gave improved dyeability over untreated fabrics due to the ion–ion interactions between the sulphonic groups present in the dye molecules and the protonated amino groups present in the fibres. The treated dyed fabrics also showed excellent fastness properties. Fibre characterisation (nitrogen content, tensile strength, shrinkage, infrared spectra and X-ray diffraction) proved the success of the amidoximation reaction.     

Modelling of integration dyeing of a wool package with acid dyes

This paper describes the behaviour observed during integration dyeing of a cross-wound wool package with an anionic dye of the supermilling type. The relationships between levelness and the variables dosing time, temperature, liquor flow rate and dye concentration in the fibre, at pH conditions corresponding to the isoelectric point of wool were examined. An increase in the flow rate and of the dye concentration during the dosing was found to improve dyeing levelness, while an increase in temperature and a decrease in dosing time impaired levelness.     

Application of sodium benzoyl thiosulphate from aqueous solution to wool and its effect on substantivity of disperse dyes. Part 2: modification of wool with sodium benzoyl thiosulphate

Sodium benzoyl thiosulphate was applied to wool fabric from aqueous solutions in order to covalently bind benzoyl groups to the fibre and thus impart disperse dye substantivity to the modified wool. The modified wool fabric was dyed with a selected model disperse dye, CI Disperse Blue 56, and the wash fastness properties of the dyeings assessed.     

Textile applications of photochromic dyes. Part 5: application of commercial photochromic dyes to polyester fabric by a solvent‐based dyeing method

A series of commercial photochromic dyes was applied to polyester by a solvent dyeing process followed by thermal fixation using dichloromethane as the solvent. The process was optimised in terms of solvent/fabric ratio, dye concentration and the conditions of thermal fixation. The dyed fabrics showed reversible photochromism, developing colour on ultraviolet exposure and fading after removal of the ultraviolet source. The degree of photocoloration, background colours, fading characteristics, fatigue resistance and storage stability of the dyes were evaluated and comparisons made with the outcomes of a traditional aqueous disperse dyeing method. A study of the visible spectra of concentrated solutions of the dyes in a range of solvents provided evidence for the origin of the permanent background colours on the fabric when applied from solvents. Relationships were established between the magnitudes of the visible absorption in solution and the background colours developed, in relation to the nature of the solvents. The results suggest that toluene and ethyl acetate may offer certain advantages as solvents for the application of these dyes.     

One–bath dyeing of polyester/wool blend with disperse dyes

The present work aims to investigate and develop a one–bath dyeing process for most common blend fibres to replace the conventional two–step process usually applied to dye each fibre constituent separately. The main objectives of the proposed process is the conservation of energy, raw materials, dyes, auxiliaries and labour.     

One-bath dyeing of wool/polyester blends with acid and disperse dyes. Part 2 — disperse dye distribution on polyester and wool

Disperse dye distribution on polyester and wool during one-bath dyeing of wool/polyester blends is discussed. The addition of carriers increases the wool's intrinsic saturation value for disperse dye, thus raising the degree of staining on the wool component at the low dye uptakes. However, staining can be minimised if the dyeing is close to or attains equilibrium conditions. Sequestering agents can accelerate the disperse dye diffusion out of the wool fibre, further reducing staining on wool and transferring more disperse dyes from wool to polyester. Citric acid can be used as a sequestering agent as well as a pH adjusting agent.     

One‐bath union dyeing of a modified wool/acrylic blend with acid and reactive dyes

Pretreated wool/acrylic fibre was obtained by a facile amidoximation process. Fibre characterisation (nitrogen content, tensile strength, shrinkage, infrared spectra and X‐ray diffraction) proved the success of the pretreatment. Union dyeing of wool/acrylic fabrics with acid and reactive dyes, namely CI Acid Red 40, CI Acid Blue 25, CI Reactive Red 194 and CI Reactive Blue 25, was obtained using a one‐bath dyeing process. Different factors that may affect the dyeability of the blend fibre, such as dyebath pH, liquor ratio, temperature, time and dye concentration, were evaluated with respect to the dye exhaustion, fixation, colour strength, levelling and fastness properties. Excellent to good fastness was obtained for all samples, irrespective of the dye used. The result of the investigation offers a new viable method for union dyeing of wool/acrylic fibres in a one‐dyebath process.     

Sorption of nonionic auxiliary products by wool and its influence on dyeing with acid dyes

Pretreatment of wool fibres with nonionic auxiliary products recommended for low-temperature dyeing resulted in an increase in dyebath exhaustion and a faster rate of dyeing. This indicated that the auxiliary product was absorbed to a certain extent by the wool. This absorption occurred rapidly and produced an increase in dyebath exhaustion and improved the levelness of the resultant dyeings     

Improving the dyeing properties of textiles via utilization of redox systems. I. Dyeing of wool and wool/polyacrylic blend fabrics with acid dye

Dyeing of wool and wool/polyacrylic fabrics with an acid dye, namely, Kiton Scarlet 4 R, was carried out in absence or presence of different redox systems. The latter were based on sodium, potassium, or ammonium peroxodisulphate or potassium periodate as oxidant and glucose, sodium thiosulphate, potassium pyrosulphite or thiourea as reductant. Regardless of the redox system used, the colour strength was far greater in presence than in absence of the redox system. Except in case of potassium periodate/glucose redox system, increasing the oxidant concentration up to 0.03 mol/l caused significant enhancement in colour strength. The same was observed upon increasing the temperature from 30 to 60°C as well as the time from 10 to 40 minutes. It is postulated that presence of the redox system alters the mode of dye attachment to the substrate. Association of the dye with the substrate, wool in particular, seems to involve covalent bonding beside the usual salt-linkage. Hence the approach presented is advantageous in producing dyeings with much higher colour strength and dye fixation at relatively low temperature.     

Differential dyeing of wool fabric with metal‐complex dyes after ultraviolet irradiation

Experiments were conducted to investigate the ultraviolet irradiation of wool fabric as a pretreatment for differential dyeing. Wool fabric was irradiated using a medium‐pressure mercury lamp in order to obtain, on the irradiated area, increased dye uptake under the same dyeing conditions as untreated wool. The chemical modification of the fibre surface as a result of ultraviolet irradiation was confirmed by an increase in metal ion absorption and hydrophilicity, in agreement with Fourier Transform‐infrared–attenuated total reflectance spectra, although scanning electron microscopy showed that the fibre morphology was unaffected. A selection of 1:1 metal‐complex dyes was used to show the maximum colour difference between irradiated and untreated areas of the fabric. The experiments focused on two effects: a double face with the same shade but different depths (greater depth on the treated side), and a double face with different shades. The latter effect was achieved by dyeing the irradiated fabrics with mixtures of acid and metal‐complex dyes. Rubbing and washing fastness evaluations at 50 °C confirmed that the dyeings after irradiation with the selected 1:1 metal‐complex dyes scored identically to conventional dyeings.     

The coloration of polypropylene fibres with acid dyes

Modified polypropylene fibre has been prepared by incorporating a polymeric additive into the polypropylene, followed by melt spinning. Fibres with various additive concentrations were dyed with acid dyes, and the amount of dye adsorbed by the fibre was compared with the concentration of dye sites supplied to the fibre by the additive. A diffusion mechanism of dye molecules through interconnected additive particles to the fibre matrix is proposed. Colour yield was assessed by reflectance spectroscopy and photoacoustic spectroscopy. The latter was shown to be particularly suitable for measuring very dark colours. Photoacoustics can also used to detect ring dyeing of fibres at lower additive concentration.     

Latest developments in the low-temperature dyeing of wool with 1:2 metal-complex and milling acid dyes*

The advantages of dyeing wool at low temperatures with metal-complex and milling acid dyes are examined. Details of variations in conventional dyeing practice are discussed in detail and recommendations for applying selected dyes are given. The cost implications of dyeing at temperatures below the boil are reviewed, and some techniques for the low-temperature dyeing of woo/nylon blends briefly mentioned.     

Controlled coloration: a success strategy for the dyeing of cellulosic fibres with reactive dyes

The impact of improving the rate of right-first-time production on productivity and profitability for a batchwise dyehouse processing cellulosic fibres is reviewed. The measurement and level of performance required from reactive dyes to support right-first-time production is defined in the form of a reactive dye compatibility matrix (RCM). The application of the RCM as a diagnostic tool in dye selection and process design is outlined.     

Neutral dyeing of wool and wool/polyester blend fabrics using sulphatoethylsulphone reactive‐disperse dyes

Two models of temporarily anionic sulphatoethylsulphone reactive disperse dyes were applied to wool, polyester and wool/polyester blend fabrics at different dyeing pH. Maximum exhaustion values and colour yield were observed at pH 7. The results showed that reactive disperse dyes containing bis‐sulphatoethylsulphone reactive groups were more convenient for neutral dyeing of wool and wool/polyester blend fabrics if compared with a dye containing a mono‐sulphatoethylsulphone group. Excellent to very good wet fastness properties on all dyed fabrics were achieved.     

Synthesis of acid dyes containing polyetheramine moieties and their low‐temperature dyeing properties on wool fiber

To realize the low‐temperature dyeing of wool fibers, the use of auxiliaries and wool modification are common methods. Low‐temperature auxiliaries may cause water‐pollution problems, and wool modification is a costly and uncontrollable process. In this study, new acid dyes, named D1–D3, containing polyetheramine groups were synthesized and applied to wool fiber by conventional and low‐temperature exhaust dyeing procedures. The results indicate that the new acid dyes could interact with wool‐fiber‐like auxiliaries and render a high exhaustion rate to the wool fiber at a dyeing temperature of 80 °C. In comparison with Acid Blue 25, the D1–D3 dyes showed an increased dyeing rate, especially under a dyeing temperature of 80 °C. Despite the bigger relative molecular masses of D1–D3, the exhaustion rates of D1–D3 were still higher, and the times of half‐dyeing were shorter than that of Acid Blue 25. The color differences between the wool fabrics dyed with the four dyes at 80 and 98 °C, respectively, were compared. We found that the color differences of D1–D3 between 80 and 98 °C were smaller than that of Acid Blue 25. The interactions between the dyes and wool fiber were analyzed and manifested by the measurement of the ζ potential of the dyes and wool fiber. The leveling and transfer properties of the D1–D3 dyes were also investigated, and the color differences of the wool fabrics dyed with Acid Blue 25, D1, and D2 were very low at all measured pH values and temperatures. The fastnesses of D1–D3 on wool fabric were almost the same as that of Acid Blue 25. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 45793.