Synthesis and application of a novel,triphendioxazine‐based,phosphorus‐containing acid dye for wool

A novel phosphorus‐containing acid dye based on triphendioxazine was designed and synthesised from diphenylamine through a series of reactions. The dye has a navy‐blue colour, high molar extinction coefficient of 5.32 × 10⁴ l/mol·cm, and high substantivity for dyeing wool in a salt‐free, aqueous dyebath. A high exhaustion value of 98.2% on wool fabrics was recorded at 3% omf and a liquor ratio of 1:20. The wash fastness values of the acid dye, including colour change and staining on cotton and wool, were grades 5, 4 and 4–5, respectively. The dry and wet fastness are grades 4–5 and 4, respectively. In addition, light fastness reaches grades 6–7 at 3% omf dye concentration. These dye properties are better than those of commercial triphendioxazine dyes, for example, CI Direct Blue 106 and CI Reactive Blue 198, under analogous dyeing conditions.     

Decolorisation by Bacillus flexus of exhausted dyebaths containing CI Acid Red 249 and their reuse for wool dyeing

A dyebath containing left-over CI Acid Red 249 after dyeing of wool was completely decolorised using an isolated bacteria Bacillus flexus. Optimisation was carried out by varying the pH, temperature, dye concentration, and microbial loading. Complete decolorisation of a 50 mg l⁻¹ dye solution was achieved in 8 h at pH 7 and 37 °C with 10% v/v loading of the bacteria. The decolorised bath was utilised for dyeing of wool fabric with the same dye at 5% shade. This cycle of dyeing–decolorising–dyeing was repeated 5 times. The evaluation of dyed fabric was done using K/S, colour values, and fastness to light and washing. Comparison of a sample dyed with the conventional exhaust process showed that the dyeing quality is not affected for all five successive reuse cycles. The results are important from the viewpoint of reducing water consumption and chemicals.     

Pomegranate fallen leaves as a source of natural dye for mordant-free dyeing of wool

The application of metal mordants is usually necessary in dyeing of wool with natural dyes to improve the dye exhaustion and fastness properties. The majority of metal salts generally used as mordants are considered as toxic and it is important to find replacements for them. Plant sources with high content of tannins are good candidates as bio-mordant or colourant to overcome this drawback. In this study, the waste fallen leaves of pomegranate tree were used as a source of natural dye for the eco-friendly dyeing of wool fabric without the use of metal mordants. The dyeing process variables including dye concentration, dyebath pH, and temperature were optimised using response surface methodology to obtain the highest colour strength. The colour strength was increased by increasing the natural dye powder up to 100%owf while the optimum pH and dyebath temperature were 4 and 100°C, respectively. The sample dyed under the optimal condition exhibited good fastness properties against washing and light. This study approved the potential of Punica granatum fallen leaves for the dyeing of wool without any mordant, while high fastness properties were obtained.     

Dyeing of leather with microencapsulated acid dye

CI Acid Black 210 was microencapsulated into liposomic systems, and the effects of the microencapsulation on dyebath exhaustion, depth of shade, colour fastness properties and through‐dyeing of chrome‐tanned leather were studied. In comparison with the original dyestuff form, the microencapsulated dye showed a deeper shade and a greater depth of through‐dyeing. Exhaustion and colour fastness values were the same.     

The effect of reactive dyes on damage in wool dyeing

This paper demonstrates that reactive dyes exert a significant fibre–protective effect when dyeing wool fabric; this effect may be measured, in a reproducible manner, using the wet–burst strength test. The effect of dyebath pH, dye concentration, dyebath temperature and dyeing time on wool can thus be evaluated. The magnitude of the above protective effect has been compared with that achieved using commercially available fibre–protective agents. It is concluded that reactive dyes are significantly more effective than the latter agents when employed in medium to full depths. It is proposed that the unusual protective effect afforded by reactive dyes is related to the following factors. Reactive dyes readily react with sulphur nucleophiles, thus inhibiting thiol–disulphide interchange reactions and thereby significantly interfering with the level of set produced in a boiling dyebath. Reactive dyes react preferentially with non–keratinous proteins in the intercellular cement and the endocuticle thus reducing their tendency to hydrolyse and to partially dissolve in the hot aqueous dyebath.     

吡唑啉酮型通用染料的合成与应用研究

以1=(2，5-二氯-4-磺酸基苯基)-5-甲基-5-吡唑啉酮为起始原料、经过一系列反应合成了一支吡唑啉酮型黄色通用染料。希望不需在染浴之外进行其它的化学反应就能用它对不同类型的织物进行染色。这是一个五步合成反应、包括重氮化偶合反应，氯置换反应，缩合反应，水解反应，缩合反应。实验中对第二步和第四步的反应工艺进行了改进，改进工艺后使两步反应的操作简化，成本降低，收率提高合成的染料以三聚氯氰为活性基，该染料及中间体的化学结构，通过^1H核磁共振谱、质谱和红外光谱分析得以表征，在中性染浴中，合成的染料可用于羊毛，丝绸，尼龙，涤纶纤维染色：通过加入N，N-二甲基乙二胺调节pH值为5，可对腈纶纤维进行染色。染料在纤维上的日晒和水洗牢度测试结果表明，染料在晴纶上的日晒、水洗牢度较低：在羊毛、丝绸上有中等的牢度性能；在涤纶、尼龙上日晒牢度较低．水洗牢度较高。     

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.     

Enzymes as auxiliary agents in wool dyeing

The action of three enzymes has been comparatively studied when used as auxiliary agents in dyebath. The absorption rate of the dye, the colour differences between wool dyed with and without enzymes and the colour fastness were determined. The action of enzymes consists of increasing dye absorption and also seems to produce a better diffusion of the dye into the fibre. The use of the enzymes in wool dyeing offers the possibility of dyeing under mild temperature conditions.     

Comparison of different ultrasound support methods during colour and chemical oxygen demand removal of disperse and reactive dyebath solutions by ozonation

In this study, the effects of ozonation, ozonation with ultrasonic bath and ozonation with ultrasonic homogeniser processes on colour and chemical oxygen demand removal properties of disperse (CI Disperse Red 60, CI Disperse Blue 337) and reactive (CI Reactive Blue 171 and CI Reactive Blue 19) dyebath solutions with and without dyeing auxiliaries were investigated. Chemical oxygen demand (in mg/l) and colour (in Hazen) measurements of the studied dyebath solutions were determined. The ozonation process caused simultaneous chemical oxygen demand removal during decolorisation. However, the improvement in chemical oxygen demand reduction was less than of that on decolorisation. The application of the combination of ozonation with ultrasonic homogeniser is the most efficient process and creates a great time advantage over the other process types studied (ozonation alone and ozonation with ultrasonic bath) to reach the same colour and levels of chemical oxygen demand removal.     

Modification of polypropylene fibres with cationic polypropylene dispersion for improved dyeability

Polypropylene (PP) fibres are important hydrophobic fibres which are used in the production of functional textiles such as sports textiles. The absence of functional groups and low polarity make PP fibres difficult to dye, thus mass coloration during fibre extrusion is the major technique applied today. However, the disadvantage of mass coloration is the low flexibility and the demand to produce high volumes. A new method to modify the surface of PP fibres utilises the deposition and thermal fixation of cationic PP dispersion. Through padding and thermal fixation of a cationic PP dispersion, dyeable 100% PP fibres can be obtained. The effects of fixation temperature, and of the amount of dispersion used on the modified fibres were studied using Fourier Transform‐infrared spectroscopy, laser scanning microscopy, dyeing experiments with CI Acid Red 151, and by determining selected fastness properties. The results indicate the potential of this new method to produce surface‐modified 100% PP fibres, which can be dyed in conventional acid‐dyeing processes and therefore used in fibre blends, for example in combination with wool.     

阳离子改性棉织物活性染料染色性能

用自制的阳离子改性剂对棉织物进行改性处理,用浓度为6%(o.w.f.)的活性红3BS、活性黄3RS、活性黑KN-B三种染料分别对改性后的棉织物进行无盐染色。分别讨论了上染速率曲线、移染性能对上染性能的影响。得到的最优固色工艺为:碳酸钠用量为10 g/L~15 g/L,在60℃下固色20分钟~30分钟。改性棉织物的匀染性良好,耐水洗色牢度和耐摩擦色牢度与常规染色基本一致。     

活性染料无盐无碱染色研究

通过对活性染料染色整理一浴的工艺条件进行分析,得出最佳的染色工艺条件:浸轧(80%轧余率)→堆置(18小时~24小时)→烘干(100℃×3分钟)→焙烘(160℃×3.5分钟)→后处理。筛选出了适合染色整理一浴的活性染料:活性翠蓝、活性红HE-7B、活性黄HE-4G、活性红HE-3B。同时不仅考虑了染料浓度对皂洗后染料的提升性能、染料浓度对织物物理性能的影响,还分析了不同有机硅油柔软剂对织物的折皱恢复角和撕破强力的影响,得出用20g/L的柔软剂T689较适合该工艺。     

The use of trisodium nitrilo triacetate in the pad–steam dyeing of cotton with reactive dyes

This paper presents results on the use of trisodium nitrilo triacetate, a biodegradable alkaline organic salt, for pad–steam dyeing of cotton with reactive dyes as a replacement for conventionally used inorganic electrolyte and alkali. Two widely used dyes, CI Reactive Red 147 and CI Reactive Blue 250, were used in the study. The colour yield, dye fixation and ultimate colour fastness achieved by using trisodium nitrilo triacetate were closely comparable with those obtained by using inorganic electrolyte and alkali. The tensile breaking force and wrinkle recovery angle of the dyed fabrics were also measured and were slightly improved when using organic salt. Additionally, the dyeing effluent showed reductions in total dissolved solids content with trisodium nitrilo triacetate.     

非反应型阳离子助剂在一浴法无盐轧蒸染色工艺中的应用

使用自制的非反应型阳离子助剂对棉织物进行预处理,分别选用活性黄K-RN、活性艳红K-2BP、活性艳蓝KN-R进行一浴法无盐轧蒸染色试验.确定了阳离子助剂处理棉织物的最佳方式和使用的最佳浓度,并与常规有盐染色进行性能对比.结果表明,采用一浴法无盐轧蒸染色对染样的固色率、色光和牢度未产生影响.阳离子助剂的使用能够替代电解质的加入,染料利用率提高25％～40％.棉纤维阳离子化能够在相对较低的温度下进行,提高了该工艺的适用范围,最终达到节能减排的目的.     

The effect of liposome on dyeing mohair/wool blends

The aim of this study was to examine the use of liposome in the dyeing of wool and mohair fibres with acid dyestuffs. Soybean lecithin and cholesterol were used to form the liposome membrane utilised in the dyebath. Liposome production was performed according to the thin lipid layer method (Bangham Method) using a rotary evaporator. Two different forms of liposome were used for dyeing wool and mohair fibres. In its first form, liposome was utilised as an auxiliary agent, where it was added to a conventional dyebath at the beginning of the process. In its second form, dyes were encapsulated with liposome and then used in dyeing. The effects of these two different forms of liposome were compared with conventional dyeing. Dyeing was carried out at depths of shade of 0.5%, 1.0% and 2.0% using three different concentrations of liposome (0.33%, 0.66% and 1.33%). An analysis of K/S values, fastness to washing, and the alkali solubility of fibres was conducted. The fibre samples dyed in the presence of liposome exhibited very good fastness to light (grade 8). The wash fastness test results of the liposomal‐dyed samples were significantly better (grade 4‐5) than for those samples which were conventionally dyed. In the presence of liposome, the tensile strength of fibres was 20 gf, whereas it was 11 gf without liposomes.     

Reactive dyeing of silk using commercial acid dyes based on a three‐component Mannich‐type reaction

Acid dyes are employed for commercially dyeing silk, which results in ionic bonds between the silk fibroin and the dye. This generally leads to low wet fastness properties for dyed silk fabrics. In this work, three commercial acid dyes with aromatic primary amine structures were selected to dye silk using a Mannich‐type reaction, resulting in improved wet fastness of dyed silk by forming covalent bonds between silk fibroin and dye. The Mannich‐type reactive dyeing was applied to silk fabrics at both 30 and 90°C in trials. Dyeing at 90°C can shorten the dyeing time compared with dyeing at 30°C, even although dye exhaustion and relative fixation at 90°C were a little lower. The dyeing process was optimised when the dyeing temperature was 90°C, dyebath pH 4, dye‐to‐formaldehyde ratio 1:30 and holding dyeing time 60 minutes. The results showed that the dye exhaustion on silk fabrics for the three aromatic primary amine‐containing acid dyes exceeded 94% and their relative fixation was over 80%. Their washing and rubbing fastness reached grade 4 or higher. Hence, the colour fastness properties of dyed silk fabrics using the Mannich‐type reactive dyeing method is superior to the conventional acid dyeing method using the same aromatic primary amine‐containing acid dyes. The Mannich‐type reactive dyeing for silk fabrics at 90°C can be developed into a novel and rapid reactive dyeing method, promising an effective dyeing process with excellent colour fastness.     

Synthesis of an amino coumarin‐based fluorescent reactive dye and its application to wool fibres

The objective of the current study was to introduce the coumarin structure into a conventional reactive dye system. A fluorescent reactive dye was synthesised based upon 7‐amino‐4‐methylcoumarin. The dye was obtained by a multi‐step sequence initiated by displacement of a chlorine group from 2,4,6‐trichloro‐1,3,5‐triazine using H‐acid. Diazo coupling of 3‐aminobenzenesulphato‐ethylsulphone to this adduct, followed by a second chlorine displacement using aminomethylcoumarin completed the sequence. The fluorescent dye and the non‐fluorescent precursor were characterised by mass spectrometry, infrared spectroscopy and capillary electrophoresis. The newly synthesised dye was applied to wool fibres using an exhaust dyeing method. The exhaustion, fixation and total efficiency values were calculated by ultraviolet–visible spectrophotometric analysis of the dyebath. The synthesised red dye presented high values for exhaustion, fixation and total efficiency on the wool fibres. The novel dye, after its application to the wool fibres, exhibited fluorescence under an ultraviolet light. This feature confirmed that the novel dye retained the inherent characteristic feature of fluorescence on the wool fibres. The dyed wool fibres exhibited level 4–5 of light fastness when compared with international wool light fastness standards.     

Ultrasonic‐assisted dyeing: I. Nylon dyeability with reactive dyes

The use of ultrasonic power (38.5 KHz, 350 W) to assist the dyeability of nylon‐6 fibre with reactive dyes is reported. The effects of the different factors that may affect the dyeability of nylon‐6 fibre with Reactive Red 55 were simultaneously carried out under both ultrasonic power and conventional heating conditions. The colour strength values obtained for the dyed samples using ultrasonic power were higher than those obtained using conventional heating. Also, the effect of alkaline soaping treatment on dye fixation for the dyed fabrics with different reactive dyes, at both acidic and neutral pHs, is generally better with ultrasonic than with conventional heating. The overall results indicate that the enhancing effect is mainly attributed to the de‐aggregation of dye molecules, which leads to better dye diffusion and possible assistance for dye‐fibre covalent‐bond fixation. The results of wet fastness properties of the dyed fabrics reveal improvement using ultrasonic power dyeing relative to the conventional heating method. © 2003 Society of Chemical Industry     

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.     

Statistical investigation of the cotton dyeing kinetics of CI Reactive Black 5 dye

In this study, the dyeing kinetics of CI Reactive Black 5 dye was statistically investigated. Cotton fabrics were dyed with this dye under different conditions by the exhaustion technique. Dye samples were taken from the dyebath from the start to the end of the process at 10 min intervals in order to determine the percentage dye exhaustion. The transmittance of the coloured dyebath samples was measured using a UV‐vis spectrophotometer. The results were investigated by statistical methods using analysis of variance and regression curves. The dye exhaustion of the cotton fabrics was found to change as a function of the dyeing parameters. Times of half‐dyeing were determined from the regression curves.