Dyeing of nylon 6 and silk fabrics with a model disulphide bis(ethylsulphone) reactive disperse dye

The synthesis of a new reactive disperse dye containing the disulphide bis(ethylsulphone) group is described. The dye has been applied to nylon 6 and silk fabrics at a variety of pH and temperature conditions. Optimum dye exhaustion and fixation were achieved at pH 8 and 130 °C. The results of dyeings on both substrates indicate that the model disulphide bis(ethylsulphone) reactive disperse dye shows a higher degree of exhaustion and fixation on silk than on nylon 6. The fastness and levelling properties on both fabrics were good.     

Dyeing of nylon 6 fabric with a new bifunctional vinyl sulphone reactive disperse dye

A new bifunctional reactive disperse dye containing a temporarily anionic sulphatoethylsulphone and a nonionic disulphide bis(ethylsulphone) groups was synthesised and applied to nylon 6 fabric by the exhaust dyeing at a variety of pH and temperature conditions. A monofunctional reactive disperse dye containing only nonionic disulphide bis(ethylsulphone) group was also synthesised and its dyeing behaviour was compared with the bifunctional dye. The bifunctional reactive disperse dye exhibited high exhaustion and fixation values at pH 6 and 120 °C. The results also indicate that the combination of temporarily anionic and nonionic reactive groups of the bifunctional dye provided great enhancement in dyeing performance compared to that of the monofunctional dye. The dyes also showed very good levelling and fastness properties on nylon 6 fabric.     

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.     

One‐bath dyeing of polyester/cotton blends with disperse and bis‐3‐carboxypyridinium‐s‐triazine reactive dyes. Part 2: Application of substantive reactive dyes to cotton at 130 °C and neutral pH†

An earlier paper reported that the reactive dyes (not the disperse dyes) were responsible for the inability to achieve heavy depths of shade, when dyeing polyester/cotton blends by a one‐bath process at 130 °C and neutral pH using reactive dyes containing a 3‐carboxypyridinium‐s‐triazinyl group. It was shown that the poor colour yield of the bis‐3‐carboxypyridinium‐s‐triazine reactive dyes was because of their low exhaustion level at 130 °C and pH of 7.0–7.5. We now report the synthesis and evaluation of some bis‐3‐carboxypyridinium‐s‐triazine reactive dye structures, possessing highly substantive chromophores, as a means of obtaining high colour yield, on 100% unmercerised cotton, under the specified dyeing conditions. The technical performance of these dyes under such conditions was compared with that of selected Novacron (Cibacron) LS and Procion H‐E dyes, applied under their recommended (atmospheric) dyeing conditions.     

Structure—reactivity studies of a new polyfunctional disulphide bis(ES-MCT/SES) reactive dye applied to silk

A new polyfunctional reactive dye containing disulphidebis(ethylsulphone-monochlorotriazine/sulphatoethylsulphone) reactive system has been synthesised and applied to silk. High exhaustion/fixation results have been achieved at 90 °C and pH 9. The vinylsulphone precursor of the disulphidebis(ethylsulphone) group combined with a sulphatoethylsulphone/monochlorotriazine reactive system confers a relatively high fixation efficiency for this type of polyfunctional reactive dye when compared with that of a conventional bifunctional reactive dye containing the sulphatoethylsulphone/monochlorotriazine reactive system. The results also indicate that high fastness properties were obtained for the reactive dyes under investigation.     

Synthesis and application of a hetero-bifunctional disulphidebis(ethylsulphone/monochlorotriazine) reactive dye

The behaviour of a heterobifunctional reactive dye based on a disulphidebis(ethylsulphone/monochlorotriazine) reactive system has been investigated. Relatively high degrees of exhaustion and fixation were achieved for cotton fabrics dyed with the disulphidebis(ethylsulphone/monochlorotriazine) reactive dye compared to bifunctional sulphatoethylsulphone/monochlorotriazine and/or conventional monofunctional monochlorotriazine reactive dyes. The results also indicate that the fastness properties are approximately the same for all the dyes studied in this investigation.     

Salt-free dyeing of cotton cellulose with a model cationic reactive dye

A model cationic reactive dye based on an anthraquinone chromophore was prepared. The synthesis of this dye was achieved by the modification of the a free amino group of an anthraquinone-based dye, reacting first with cyanuric chloride and then with N -(2-aminoethyl)pyridinium chloride. TLC analysis was employed to follow the chemical reactions. The application of the prepared dye to cotton fabric was carried out using the exhaustion method without the addition of electrolytes. The results showed that, despite no electrolytes being present in the dye bath, a high percentage of dye exhaustion could be obtained. The high percentage of dye exhaustion was attributed to the attractive force between positive charges on the dye molecule and the negatively charged fibre surface. A high degree of dye fixation with excellent wash fastness was also achievable. Advantageously, it was found that this cationic reactive dye showed promising fastness to light when compared with that of analogous conventional basic dye on cotton. It is believed that the pyridinium cationic moiety, which attached separately to the chromophore via aliphatic spacer groups, was later eliminated during the washing-off process, hence causing an insignificant effect on the photofading of the dyed fabric.     

Dyeing of nylon with reactive dyes. Part 2. The effect of changes in level of dye sulphonation on the dyeing of nylon with reactive dyes

Four mono-functional reactive monochlorotriazinyl (MCT) dyes, each derived from the same chromophore and possessing a single monochlorotriazinyl reactive group, but differing only in degree of sulphonation, were synthesised and evaluated on nylon. The colour yield, degree of exhaustion, fixation, and the fastness properties of each dye were assessed. Initial exhaustion, at pH 4, was high for all dyes but percentage fixation, via covalent bond formation, increased with increasing levels of sulphonation. In all cases fixation efficiency reduced markedly with increasing concentrations of dye applied.     

双一氟三嗪活性染料的染色方法与染色性能

合成了一支含双一氟三嗪活性基团的活性染料并应用于棉纤维的染色。详细考察了染色温度、固色温度、加碱量以及加盐量对其染色结果的影响。结果表明,在染色温度90℃,Na2SO4用量70g/L,固色温度40～60℃,碱量（Na2CO3）0～3 g/L时染料的固色率可以达到87%。与同结构的含双一氯均三嗪活性染料相比,含氟活性染料的固色率提高13.5%。该染料具有较好的各项牢度性能。     

Synthesis of anionic water‐borne polyurethane with the covalent bond of a reactive dye

We successfully synthesized an anionic water‐borne polyurethane (PU) capable of reacting with a reactive dye to form a covalent bond with the dye molecule. The anionic water‐borne PU was synthesized and grafted with the reactive dye to form a dyed PU. First, the PU prepolymer was synthesized from 4,4′‐methylene bis(isocyanatocyclohexane), poly(tetramethylene glycol), 2,2′‐bis(hydroxymethyl) propionic acid (as an anionic center), and triethyleneamide (as a neutralizer). Then, pure water was added to emulsify and disperse the prepolymer to form an anionic water‐borne PU prepolymer. Finally, the extender N‐(2‐hydroxyethyl) ethylene diamine was used to extend the anionic water‐borne prepolymer to form a PU polymer with hydroxyl groups that could further react with the reactive dye molecule. With respect to the heating properties, the dyed PU polymers exhibited higher glass‐transition temperatures of the hard segment than those without dye molecules. However, neither the glass‐transition temperature of the soft segment nor the melting temperature of the soft segment varied in the presence of dye molecules, but they were changed with various chain lengths of the soft segment. As for the mechanical properties, the modulus and strength of the dyed PU polymers decreased because of the bulkiness of their dye molecules, but the breaking elongation increased. Moreover, the inherent viscosity decreased in the presence of the dye molecules. As for the dyeing properties, the percentage of dye grafting was greater than 90%. The dye‐grafted PU exhibited a lower percentage of migration than PU extended with ethylene diamine (without hydroxy groups) and also showed a higher grade of colorfastness to light. © 2002 John Wiley & Sons, Inc. J Appl Polym Sci 84: 797–805, 2002; DOI 10.1002/app.10336     

Synthesis and application of a polyfunctional bis(monochlorotriazine/sulphatoethylsulphone) reactive dye

The behavior of a polyfunctional reactive dye containing bis(monochlorotriazine/sulphatoethylsulphone) reactive system on silk has been investigated. The twinned monochlorotriazine/sulphatoethylsulphone reactive system confers a relatively high fixation efficiency of this type of polyfunctional reactive dye even at low salt and/or temperature conditions when compared with that of the conventional bifunctional reactive dye containing one monochlorotriazine/sulphatoethylsulphone reactive system. The results also indicate that the fastness properties are approximately the same for both the reactive dyes under investigation.     

红色复合多活性基活性染料的结构与性能关系研究--染色特性参数

应用直接性S、反应性R、竭染率E、表观固色率F、实际固色率Fr、移染指数MI、易洗涤性因子WF、匀染因子LDF等八个参数，描述了10只红色复合双活性染料的上染、匀染、清洗等染色特性。M型染料的上染曲线形状介于碱控型和盐控型之间，直接性相对较小的染料，上染曲线更接近于碱控型；直接性相对较大的染料，更相似于盐控型。在本文研究的染料中，用苯系重氮组分的染料直接性较小，易洗涤性好，移染指数和匀染性好，但竭染率和固色率相对较低。用蔡系重氮组分的染料具有良好的直接性，因而导致较好的竭染率和固色率和中等的匀染性。尤其是以2-萘胺-1，5-双磺酸为重氮组分的R4，适中的直接性、缓和的上染速度和易洗涤性，加上良好的移染性与匀染性，使其被选为M-型染料三原色之红色组分。但其固色率尚属中等水平。重氮组分上也具有硫酸酯乙基砜基的活性染料R5、R6，具有中等直接性，其反应性、竭染率、固色率均较高，和优异的易洗涤性和很好的湿处理牢度，但移染性和匀染性稍低．乙烯砜染料的直接性比相应的乙基砜硫酸酯染料大，在苯系重氮组分中差别比萘系明显。但E，F相差不大，乙烯砜的易洗涤性略差于相应的硫酸酯乙基砜染料。通过不同芳环、磺酸基和硫酸酯乙基砜基引入重氮组分，可以调节本文涉及的复合双活性基染料的亲和力、反应性，从而对染料的竭染率、固色率、易洗涤性、匀染性和湿处理牢度作出大致的预测，并可作为染料结构和复配增效配方设计的参考依据。     

Synthesis and application to cellulose of reactive dye precursor of anti‐bacterial N‐halamine

To achieve textile dyeing and functional finishing in one process, a bleach‐resistant reactive dye precursor to anti‐bacterial N‐halamine was synthesised by reacting a type of dichlorotriazine reactive dye with 4‐amino‐2,2,6,6‐tetramethylpiperidine. The synthesised compound, which can be transformed to an N‐halamine molecule by exposure to dilute bleach solution, was used to dye cotton fabrics. After exposure to a dilute sodium hypochlorite solution, dyed cotton fabrics showed excellent anti‐bacterial properties against Staphylococcus aureus and Escherichia coli O157:H7, facilitating a ca. 6‐log reduction in bacteria within a short period of contact. Compared with the dichlorotriazine reactive dye, the reactive dye precursor demonstrated comparable dyeing properties including exhaustion and fixation values. No differences in rub fastness, wash fastness or bleach fastness were detected between fabrics dyed with, respectively, dichlorotriazine reactive dye and the reactive dye precursor to N‐halamine.     

Investigation into the dyeing of wool with Lanasol and Remazol reactive dyes in seawater

Freshwater is an increasingly scarce resource that is extensively used in textile wet‐processing. In seeking to identify alternative low freshwater‐usage coloration technology, this study examined the potential use of seawater (SEAW) as the dyeing medium for wool coloration using a range of reactive dyes. Initially, the dyeing behaviour of the wool fabric in simulated seawater (SSW) was compared with conventional dyeing from distilled water (DW) using α‐bromoacrylamide‐based Lanasol dyes and sulphatoethyl sulphone‐based Remazol dyes. These preliminary studies demonstrated that comparable coloration could be achieved in the SSW medium based on an assessment of the dye exhaustion, dye fixation, colour yield and levelness. Subsequent dyeing studies of wool using Mauritian seawater with both the Lanasol and Remazol reactive dyes confirmed that, based on the dye exhaustion, dye fixation, colour yield and levelness, comparable coloration could be achieved, highlighting the possibility of substituting freshwater with seawater as the dyeing medium.     

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.     

Dyeing of nylon 6 fabric with a bifunctional sulphatoethylsulphone reactive disperse dye

A bifunctional reactive disperse dye containing two temporarily anionic sulphatoethylsulphone groups was synthesised and applied to nylon 6 fabric by exhaust dyeing at a variety of pH levels and temperatures. A monofunctional reactive disperse dye containing one temporarily anionic sulphatoethylsulphone group was also synthesised, and its dyeing behaviour was compared with the bifunctional dye. The bifunctional reactive disperse dye exhibited high exhaustion and total fixation yield under alkaline conditions. The results also indicate that the introduction of two temporarily anionic sulphatoethylsulphone groups of the bifunctional dye gave an enhancement in dyeing performance compared with that of the monofunctional dye. The dyes also showed very good levelling and fastness properties on nylon 6 fabric.     

Spectrophotometric investigation of laser dye diffusion in styrene–acrylonitrile copolymer solutions

An ultraviolet spectrometer was used to measure the absorption kinetics of a laser dye, 1,4‐bis(5‐phenyloxazoyl‐2‐yl) benzene, at its maximum wavelength in solutions of styrene–acrylonitrile copolymer dissolved in 1,4‐dioxane. From the time‐dependent absorbance data, the dye diffusion coefficient was calculated by a combination of Fick's law of diffusion with the Beer–Lambert law of absorption. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 95: 1481–1484, 2005     

Dye–fibre bond stabilities of some reactive dyes on cotton

Cotton fabric dyed with commercial reactive dyes of the monochloro-s-triazine, bis(monochloro-s-triazine), and bis(monofluoro-s-triazine) type was treated in buffer solutions pH 10 and 12 at 60, 85 and 98°C. Hydrolysis has been investigated using spectrophotometrical measurements of hydrolysed dye at λ_max. The percent of hydrolysed dye was calculated.     

Behavior of chemically modified cellulose towards dyeing. IV. Dyeability of poly(methyl vinyl pyridine)-cellulose graft copolymers before and after treatment with epichlorohydrin

Grafting of 2-methyl-5-vinyl pyridine (MVP) onto partially carboxymethylated cotton having 6 meq COOH/100 g cellulose (PCMC) was effected by a Fe²⁺-H₂O₂ redox system. Different graft yields were obtained by varying MVP concentration from 10 to 100 wt % PCMC. In a subsequent step these graft copolymers were treated with epichlorohydrin. Dyeing of untreated cotton, PCMC, PCMC grafted with MVP, and epichlorohydrin-treated poly(MVP)-PCMC graft copolymers was carried out at room temperature (27°C) for varying lengths of time (2.5–60 min) in the absence of alkali catalyst or any other additives. Three reactive dyes, Procion Red M-GS, Procion Orange Brown H-2GS, and Remazole Brilliant Blue; a direct dye, Orangé Solophényle 2RL; and an acid dye, Erio Blue Marine 2GR were used at a concentration of 2% by weight of material. It was found that none of the three reactive dyes or the acid dye interacts with untreated cotton or PCMC. In contrast, the direct dye did. PCMC grafted with MVP, on the other hand, showed a substantial extent of dye exhaustion regardless of the dye used. After-treatment of poly(MVP)-PCMC graft copolymers with epichlorohydrin significantly enhanced the extent of dye exhaustion. The latter reacted almost 100% with all the dye examined, irrespective of the graft yield, which varied from 1.6% to 63%. Dyeings for reactive dyes withstood soaping for 1 hr at boil and extraction with 50% dimethylformamide, whereas dyeings for the direct dye and the acid dye failed to do so. It is believed that the presence of pyridine moieties in the graft act as an internal, built-in catalyst for expediting the reaction of reactive dyes with cellulose hydroxyls and behave as a weak base capable of salt-linkage formation in case of the acid and direct dyes.     

The Modification of Wool with Reactive Hydrophobes

A series of seven reactive hydrophobic compounds was synthesised and authenticated. Aqueous dispersions of these compounds were prepared by milling and applied to wool by pad–dry–steam and exhaustion procedures. The extent of fixation achieved was assessed by determining the weight gain of the treated wools. Treated wool fabric was transfer printed with disperse dye papers and the disperse dye affinity was assessed both by dye yield (K/S) measurements and by determining the