Study of the Influence of Gemini Cationic Surfactants on the Dyeing and Fastness Properties of Polyester Fabrics Using Naphthalimide Dyes

In this paper, the dyeing and fastness properties of three monoazo naphthalimide dyes including different imide groups (dye 1: ethyl amine, dye 2: ethyl glycinate and dye 3: glycine) on a polyester fabric were investigated in the presence of two gemini cationic surfactants (symbolized as 12‐4‐12 or 14‐4‐14) and a conventional single chain surfactant, dodecyltrimethylammonium bromide (DTAB). The color strength (K/S) of naphthalimide dyes on polyester fabric was measured through the reflectance spectrophotometric method, and the values obtained in the presence of different cationic surfactants increased in the order of dye 3 < dye 2 < dye 1. Although the K/S values indicated that the gemini cationic surfactants had almost no effect on the dyeing behavior of dye 1, but they were effective in dyeing ability of dye 2 and dye 3. The data for dye 2 demonstrated that build up of polyester fabrics in the presence of gemini surfactants are more than the conventional cationic surfactant, and also K/S values of dye 3 on polyester fabrics were in the order: DTAB > 12‐4‐12 > 14‐4‐14. It was found that the washing and rubbing fastness properties improved with increasing the concentration of surfactants. In addition, the sublimation fastness of dye 3 was more than the other dyes owing to the presence of a polar group in its chemical structure, and the light fastness of naphthalimide dyes on polyester fabrics was generally moderate.     

Solubility of Two Disperse Dyes Derived from <Emphasis Type="Italic">N</Emphasis>-Alkyl and <Emphasis Type="Italic">N</Emphasis>-Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

The solubility of naphthalimide-based monoazo dyes containing N-ethyl and N-ethanoic acid groups was investigated in the presence of a conventional monomeric counterpart (DTAB) and two cationic gemini surfactants (12-4-12 or 14-4-14) individually. The effective parameters on dye solubility such as temperature, time and concentration of surfactants were investigated by UV–Visible spectrophotometry. The results demonstrate that the solubility of both dyes was considerably increased at concentrations above the surfactant CMC. The wavelength for the maximum absorbance of dyes in the aqueous solution shifts toward longer wavelengths with changes in the concentration of the cationic surfactants. A kinetic study of solubilization of dyes in cationic surfactants solution showed that the rate of solubilization follows the pseudo-first-order reactions. Rates of solubilization were in the range of 0.5 × 10⁻³ to 6.8 × 10⁻³ min⁻¹ for both dyes. The disperse dye containing a carboxylic acid group (dye 2) has a higher solubility rate than the dye containing an alkyl group (dye 1). The type of surfactant has a very low effect on adsorption of dye 1 onto the polyester fibers, whereas changing the surfactant type from DTAB to 12-4-12 or 14-4-14 causes adsorption of dye 2 on polyester to decrease.     

涤纶常压染色促染剂的制备及应用

以有机碱三乙醇胺为催化剂,邻苯二甲酸酐(简称苯酐)与自制阳离子改性剂WLS反应,制备苯酯助剂,并将其作为涤纶分散黑ECT染料常压染色的促染剂。通过系统研究,优化出苯酯合成工艺,并探讨苯酯助剂与N-正丁基邻苯二甲酰亚胺(简称亚胺)复配对分散黑ECT常压染色性能的影响。结果表明:苯酯与亚胺有很好的协同效应,二者质量比按2∶1复配时,可获得最佳染色效果。该复配促染剂应用于涤纶常压染色中,染色后织物先进行195℃焙烘2.5 min,再还原清洗,织物的染色深度K/S值和上染百分率较常压无助剂、同条件染色工艺显著提高,而且基本达到传统高温高压的染色效果。     

分散染料还原性质的极谱研究

本文通过经典极谱法对分散染料的还原难易、快慢进行了探讨。测定了分散染料半波电位（E1/2）及表观半还原时间（t1/2）,分析了分散染料半波电位与拨染性之间的关系,研究了分散染料结构类型、取代基团、工艺参数对半波电位和拨染性的影响。提出表观半还原时间与拔染速率之间存在的对应关系。     

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.     

Surface and Biocidal Properties of Gemini Cationic Surfactants Based on Propoxylated 1,6-Diaminohexane and Alkyl Bromides

Two new classes of gemini cationic surfactants—hexanediyl-1,6-bis[(isopropylol) alkylammonium] dibromide {in the abbreviation form: C_nC₆C_n[iPr-OH] and C_nC₆C_n[iPr-OH]₂; alkyl: C_nH_{2n + 1} with n = 9, 10, 12 and 14}—have been synthesized by interaction of alkyl bromides with N,N′-di-(isopropylol)-1,6-diaminohexane and N,N,N′,N′-tetra-(isopropylol)-1,6-diaminohexane. The surface tension, electrical conductivity, and dynamic light scattering (DLS) techniques were used to investigate the aggregation properties of the gemini cationic surfactants in aqueous solution. The formation of critical aggregates at two concentrations in an aqueous solution from obtained gemini cationic surfactants were determined via the tensiometric method. Thus, these gemini cationic surfactants start to form aggregates at concentrations well below their critical micelle concentrations (CMC). The surface properties and the binding degree (β) of the opposite ion were tested against the length of the surfactant hydrocarbon chain and the number of the isopropylol groups in the head group. By applying the DLS technique, it was explored that how the number of isopropylol groups in gemini cationic surfactants with C₁₂H₂₅ chain affects the sizes of micelles at concentrations greater than CMC. It was discovered that the obtained gemini cationic surfactants have a biocidal character.     

Synthesis,interfacial properties,and antimicrobial activity of a new cationic gemini surfactant

Tetramethylene-1,4-bis(N,N-dodecylammonium bromide), cationic gemini surfactant, (12-4-12) was first synthesized with an one-step and shortened procedure and its interfacial and antimicrobial properties were compared with a conventional single-chain cationic surfactant, cetyltrimethylammonium bromide (CTAB). The interfacial and thermodynamic properties of both surfactants reveal that critical micelle concentration (CMC) of this novel synthetic cationic dimeric surfactant is lower than that of cationic monomeric surfactant at almost 15 times of its magnitude, which is due to the increase in hydrophobicity of the surfactant molecules by having dual hydrocarbon chains. In comparison with CTAB, the produced compound 12-4-12 yields much better interfacial and thermodynamic properties. The antimicrobial activities of the synthesized gemini surfactant were tested against eight strains of bacteria, as well as two strains of fungi. The results showed that both 12-4-12 compound and CTAB exhibited higher inhibitory effects on the growth of Gram-positive bacteria and fungi than that of Gram-negative bacteria. The minimum inhibitory concentrations in molar of 12-4-12 against all tested Gram-negative bacteria were lower than those of CTAB, which is hypothetically due to the lower HLB together with smaller CMC values of our gemini surfactant.     

载体复配对涤纶分散染料常压沸染的影响研究

将N-正丁基邻苯二甲酰亚胺、自制苯酯助剂和WLS联合应用于涤纶常压沸染染色中,结果表明:N-正丁基邻苯二甲酰亚胺和苯酯助剂具有增塑涤纶的作用,而苯酯助剂和WLS具有阳离子结构,可促进分散染料阴离子胶束吸附涤纶,这3种助剂按适当比例复配有协效作用。复配载体应用于涤纶织物分散染料常压染色,染料上染百分率、染色织物表观深度、耐摩擦牢度及耐皂洗牢度与传统高温高压染色工艺效果相当。     

Gemini Surfactants with Polymethylene Spacer: Supramolecular Structures at Solid Surface and Aggregation in Aqueous Solution

Aggregation of α,ω-bisammonium cationic gemini surfactants with a variable polymethylene spacer and two dodecyl chains has been studied on a solid surface and in aqueous solution. Scanning electron microscopy and dynamic light scattering with the time-resolved fluorescence quenching technique were used for the experiments on the solid surface and in aqueous solution, respectively. As the results from the scanning electron microscopy indicate, the morphology of supramolecular structures of gemini surfactants at the solid surface depends on the spacer length. In aqueous solution, gemini surfactants with spacers consisting of 4, 6, 8, 10, and 12 CH₂ groups form spherical micelles with diameters between 2 and 3.5 nm. Micelles of gemini surfactant with a short ethylene spacer show an increase in size up to 13 nm at the maximum concentration investigated. The aggregation number of micelles determined by time resolved fluorescence quenching was found to be in the range 14–25 for the spacer lengths from 6 to 12 CH₂ groups with only a moderate increase with surfactant concentration. For micelles of gemini surfactants with the short ethylene spacer, the increase of the aggregation number up to 50 at the maximum concentration was observed. The findings support micellar growth of gemini surfactants with short ethylene spacer.     

Dispersant-free dyeing of polyester with temporarily solubilised disperse dyes

In an effort to overcome some of the environmental problems associated with the use of dispersing agents, four temporarily solubilised disperse dyes had previously been synthesised and characterised for use in dispersant-free polyester dyeing. In this paper the dyeing and fastness characteristics of these dyes on polyester fabrics have been examined. It was found that the optimum pH to guarantee a moderate rate of hydrolysis was 5, which allowed temporarily solubilised disperse dyes to be successfully applied to polyester without the use of dispersants. The dyebath remained stable during the dyeing procedure. The dyes exhibited good levelling and fastness properties on polyester.     

Aftertreatment of polyester fabric dyed with temporarily solubilised disperse dyes

Temporarily solubilised disperse dyes derived from aminophenyl-4-(β-sulphatoethylsulphone) are exhausted on the polyester fibre mostly in the vinylsulphone form and to a lesser extent as their hydroxyethylsulphone analogues. After dyeing, to remove the unexhausted dyes on the polyester fibre, sulphite anions were added to the dyebath. The vinylsulphone residue of the dye was attacked by the sulphite anion via an addition reaction converting the dye into a soluble derivative, which then had little affinity for the polyester fibre. The effect of sodium sulphite on the conversion of the dye was investigated using HPLC. The wash and rub fastness properties of the dyed fabric aftertreated with sodium sulphite were similar to those obtained with reduction clearing.     

Effect of Sandospace R on the dyeability of gamma-irradiated wool,wool/polyester and polyester fabrics with some disperse dyes containing amino groups

The effect of Sandospace R on the dyeability of gamma-irradiated wool, wool/polyester and polyester fabrics towards disperse dyes has been investigated. The effects of the different factors that may affect the colour yield of the dyed samples (such as radiation dose, Sandospace R concentration, pH strength of the dye bath, dye concentration, dyeing temperature and time were studied. In general, and regardless of the studied factor, the irradiated fabric showed a significant dye affinity for the disperse dyes employed compared/to the unirradiated fabrics. However, the different fabrics irradiated to a dose of 2Mrad showed the highest colour strength with a high level of dyeing. Also, it was observed that a concentration of Sandospace R as low as 0·5% effectively enhances the dye affinity for the disperse dyes used here. Moreover, it was found that the pH of the dyeing bath at which the highest colour strength obtained was 3. Increasing the dye concentration up to 4% based on fabric weight, caused a significant enhancement in the colour strength, whilst raising/the dyeing bath temperature from 60°C to 100°C appreciably accelerated the rate of dye uptake. Complete exhaustion absorption of the disperse dye occurred over a period of 2h. © 1998 Society of Chemical Industry     

Studies on the possibility of recycling microencapsulated disperse dye‐bath effluents

The volume of water consumed by human beings has increased dramatically in recent years while water supply has remained constant; both demographic growth and the expansion of industrial activity require more water consumption. The textile industry is undoubtedly one of the most pressured industries that need water intensively. Efficient use of water tends to be a crucial subject for the dyeing industry. In this study, melamine resin microcapsules containing pure disperse dyes were prepared by in situ polymerization. The microcapsules were characterized on the basis of structure, morphologies, mean particle size, and size distribution. The dyeing behaviors of microencapsulated disperse dyes (MDDs) were evaluated on polyester fabrics in the absence of auxiliaries. Its effluent can be reused several times after being simply filtered and can be used as solvent for PET fabric scouring. The treated fabrics exhibited satisfactory levelness and fastness properties. MDDs can be used in dyeing PET, without using surfactants, and the effluents can be recycled and reused. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

A facile synthesis and tautomeric structure of novel 4‐arylhydrazono‐3‐(2‐hydroxyphenyl)‐2‐pyrazolin‐5‐ones and their application as disperse dyes

The main target of this paper was the synthesis of novel azo disperse dyes with better dyeing properties, together with a systematic investigation to determine their dominant tautomer(s) from 12 possible tautomeric structures. In this regard, novel azopyrazolin‐5‐one dyes were synthesised via the reaction of hydrazine hydrate with 2,3,4‐chromantrione‐3‐arylhydrazones. The acid dissociation constants both in the ground and in the excited state for the series prepared were determined and correlated by the Hammett equation. The results of this correlation, together with spectral data, indicated that the compounds under scrutiny exist predominantly in the keto‐hydrazo structure as a Z‐configuration, both in the ground and in the excited state. Finally, the synthesised dyes were applied as disperse dyes for dyeing polyester fabrics, and their fastness properties were evaluated. Also, the position of colour in CIELAB coordinates was estimated and discussed.     

Dyeing and finishing of lyocell union fabrics: an industrial study

Lyocell union fabrics, namely lyocell/silk and lyocell/polyester fabrics, were woven in different fabric constructions and dyed with reactive dyes, acid dyes and a disperse dye. The resulting dyed fabrics were given a resin finishing treatment and their wash fastness was measured. With appropriate dye selection and control of dyeing conditions, some bright solid shades and effective cross‐dyed shades were obtained. The dyed and finished fabrics had a smooth, lustrous handle, ideal for lightweight garments.     

阳离子染料可染聚酯纤维染色工艺探讨

本文用分散型阳离子黄SD-5GL、红SD-GRL、蓝SD-GSL上染阳离子可染纤维,研究了温度、保温时间、升温速率、染浴的pH值对上染率和K/S值的影响,并讨论了分散型阳离子染料和分散染料拼混对染色性能的影响。研究结果表明,三组分阳离子可染涤纶可以在常压下染色。     

The Use of Disperse Dyes Containing Diester Groups to Produce Discharge Effects on Fully Dyed Lightweight Polyester Fabrics

The chemistry of a range of disperse dyes containing diester groups of carboxylic acids (Dispersol PC dyes) are briefly described. The development of a ‘discharge–resist’ printing method and a true resist technique on 100% polyester using these disperse dyes is then outlined. The introduction of two new auxiliary products (Matexil PN–AD and PN–DG) has now led to the use of these Dispersol PC dyes in a process for the discharge printing of fully dyed lightweight polyester fabrics (generally defined as those fabrics having a weight of 80 g/m² or less and a yarn count per filament of less than 3 dtex). Emphasis is placed on the practical processing conditions necessary to produce these discharge styles and in particular on a new approach to the print thickening system that will enable extremely fine line definition to be achieved.     

Novel hydrolysable azo disperse dyes based on N‐ester‐1,8‐naphthalimide: dyeing of polyester–cotton blends

The dyeing of polyester–cotton blends with new alkali‐hydrolysable azo disperse dyes based on N‐ester‐1,8‐naphthalimide was investigated. Polyester–cotton blend fabrics were dyed using both one‐ and two‐bath methods. Dyes 3 and 4 offered lower colour yield on polyester using the one‐bath method. For the rest of the dyes, employing either the one‐ or two‐bath method resulted in a similar colour yield on polyester fabric. The results for fastness properties and colour yield of the dyeings showed that the dyes were suitable for dyeing polyester–cotton blends using the one‐bath method. The kinetic study of hydrolysis of the dyes in alkali media obeyed the pseudo first‐order reaction rate.     

One-bath dyeing of a polyester/cotton blend with reactive disperse dyes from 2-hydroxypyrid-6-one derivatives

A series of temporarily solubilised reactive disperse dyes based on 1-substituted derivatives of 2-hydroxypyrid-6-one were applied to a 65;35 polyester/cotton blend using a one-bath dyeing method without dispersing agent. The dyeing behaviour of these dyes on polyester and cotton fabrics, and polyester/cotton blend fabric, were studied. The colour yields of the dyes on the polyester/cotton blend were found to be highly dependent on the initial pH, optimum results being obtained at pH 5. Good levelling and good to excellent fastness properties were obtained on the blend, with the exception of lightfastness, which was moderate.     

Antimicrobial activity of some new 4‐arylazo‐3‐methylthiophene disperse dyes on polyester fabrics

A series of novel 4‐arylazo‐3‐methylthiophenes was synthesized by the heterocyclization of 2‐arylhydrazono‐2‐acetyl thioacetanilide derivatives with a variety of α‐halogenated reagents, such as chloroacetone, phenacyl bromide, ethyl chloroacetate, and chloroacetonitrile. The structures of the synthesized thiophene derivatives were confirmed by ultraviolet–visible, IR, and ¹H‐NMR spectroscopic techniques and elemental analysis. The synthesized dyes were applied to polyester fabrics as disperse dyes, and their fastness properties were evaluated. The dyed polyester fabrics displayed antibacterial efficacy against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011