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.     

Synthesis of methine dyes derived from indol‐2‐ones and their dyeability on polyester fibres

Three series of methine dyes were synthesised by the condensation of indol‐2‐ones with aryl acroleins. The structures of these dyes were confirmed by ¹H nuclear magnetic resonance spectroscopy, infrared spectrometry and elemental analysis. The ultraviolet‐visible absorption spectra of the dyes were examined in different solvents. The maximum absorption wavelength ranged from 386 to 495 nm. The dyes were applied to polyester fibres, and the colour gamut and dyeing properties were investigated. Results showed that the dye uptake (percentage exhaustion) was 86.9–92.0%, with the hue changing from yellow to red. The rubbing fastness, wash fastness, and sublimation fastness were between 4 and 5.     

The use of poly(amidoamine) dendrimer in modification of jute for improving dyeing properties of reactive dyes

In this study, the poly(amidoamine) (PAMAM) G‐2 dendrimer was applied to the jute yarn. Fourier transform infrared spectrophotometry (FTIR) of the dendrimer‐treated jute yarn indicated that all carbonyl groups of the jute fiber have reacted with amino groups of the PAMAM dendrimer. Jute yarns which had been pretreated with PAMAM dendrimer displayed markedly enhanced color strength with reactive dyes, even when dyeing had been carried out in the absence of electrolyte or alkali. Dendrimer‐treated jute yarn showed much better light‐fastness than that of untreated jute yarn. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Synthesis,spectral and dyeing properties of phenylazopyrazolone‐containing acylamide disperse dyes designed for poly(lactic acid)

A series of phenylazopyrazolone disperse dyes containing an acylamide moiety were synthesised from carboxyl‐containing acid dyes via chlorination and amidation with different sorts of amines. The structures of these new dyes were confirmed by Fourier Transform–infrared, proton nuclear magnetic resonance, mass spectroscopy and elemental analysis. Their solvatochromic properties in different solvents were also investigated and the absorbance spectra of the acylamide dyes in solution exhibited a red shift when dissolved in dimethylformamide, compared with acetone. Their dyeing behaviour, including dye sorption, colour build‐up and colour fastness properties on poly(lactic acid) fibres, was also determined, whereupon it was found that the tertiary acylamide dyes simultaneously exhibited high dye sorption and satisfactory colour build‐up and fastness properties on the poly(lactic acid) fabric.     

Novel anti‐bacterial acid dyes derived from naphthalimide: synthesis,characterisation and evaluation of their technical properties on nylon 6

As an attempt to combine the dyeing and functional finishing steps into one process, two novel anti‐bacterial monoazo acid dyes based on N‐ester‐1,8‐naphthalimide were synthesised. To do this, 4‐amino‐N‐ethyl glycinate‐1,8‐naphthalimide was prepared, diazotised and then coupled to thiosalicylic acid or salicylic acid to produce anti‐bacterial dyes. The synthesised dyes were purified and then fully characterised using Fourier Transform–infrared spectrometry, proton nuclear magnetic resonance spectroscopy and melting point analysis. Dispersion of the dyes was prepared in water and applied to nylon 6 fabrics. The novel dyes offered good build‐up properties on the substrate. The anti‐bacterial efficacy of the synthesised dyes was assessed, with the dyes showing activity against both Gram‐positive and Gram‐negative bacteria.     

Synthesis of a novel fluorescent coloured copolymer based on 4‐butylthio‐1,8‐naphthalimide

A novel fluorescent coloured copolymer based on naphthalimide was prepared. Acenaphthene was brominated and oxidised to prepare 4‐bromo‐1,8‐naphthalic anhydride and further reacted with butanethiol, 2‐aminoethanol and acryloyl chloride, in order to obtain a new polymerisable fluorescent dye. The synthesised dyes were characterised by differential scanning calorimetry, absorption spectroscopy (Fourier Transform–infrared, proton and carbon nuclear magnetic resonance, ultraviolet–visible spectroscopy) and fluorimetry. Molar extinction coefficients and wavelength maxima were obtained by examining the dye solution in ethanol. The solvatochromic effects of the prepared dyes have also been investigated. Finally, the dye was copolymerised with methyl methacrylate and an intrinsically coloured copolymer was obtained. The photophysical characteristics of the obtained copolymer have also been considered. It is assumed that 99% of the copolymerised dye is chemically bonded to polymer chains. The fluorescent characteristics of the copolymer in the solid state were determined by fluorometer and it was found that it has relatively high fluorescent intensity. The physical properties of the synthesised copolymer have been evaluated by differential scanning calorimetry and gel permeation chromatography.     

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.     

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.     

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.     

Synthesis,spectral properties and application of novel disazo disperse dyes derived from polyester waste

Terephthalic dihydrazide was obtained through aminolytic depolymerisation of polyester bottle waste by using hydrazine hydrate. It was further reacted with 4‐aminobenzoic acid in the presence of polyphosphoric acid to obtain a cyclic compound, 4,4′‐[5,5′‐(1,4)‐phenylene)bis(1,3,4‐oxadiazole‐5,2‐diyl)dianiline, having a heterocyclic moiety. Diazotisation of this compound followed by coupling with various N,N‐disubstituted anilines afford a series of novel disazo disperse dyes. The structures of these synthesised dyes were confirmed by elemental analysis and Fourier Transform–infrared, proton nuclear magnetic resonance and mass spectroscopy. Ultraviolet–visible spectra of these azo dyes in different polar solvents showed considerable variation in the wavelength of maximum absorbance (λ_max). Application of these dyes on polyester and nylon fabrics using high‐temperature dyeing methods gave brilliant yellowish red hues with fair to moderate light fastness and very good to excellent wash fastness and sublimation fastness.     

Synthesis and dyeing properties of polyvinylamine dyes for cotton

Novel polyvinylamine dyes were designed and synthesised from poly(N‐vinylformamide‐co‐vinylamine) and reactive dyes, then used to dye cotton fibres by the dip‐pad‐steam process, with the dyeing methods being examined in detail. Each polyvinylamine dye was fixed to cotton without a crosslinking agent through covalent bonds formed between the reactive group of the dye and the cotton fibres. A fixation of 99% was achieved, with grades of 4 and 4‐5 wash and dry‐rub fastness, respectively.     

A study of novel bisazo reactive red dyes with good wet fastness

Three series of bisazo reactive red dyes were synthesised using 6‐amino‐1‐naphthol‐3‐sulphonic acid and its derivatives as the coupling components. The dyeing parameters and wash fastness of these dyes on knitted cotton were evaluated and the relationships between the structure and dyeing properties were investigated. It was found that the hydrophilic groups introduced into the dye molecules decrease the substantivity and fixation of the dyes, but increase the build‐up and migration properties. The defined wash‐off factor can directly reflect the wash fastness of the dyes and the build‐up property can be improved by commercialisation using certain auxiliaries. The results indicate that there is the possibility of synthesising a red reactive dye with a satisfying balance between high fixation and good wash fastness and several such dyes have been developed.     

Synthesis and application of yellow azo‐anthraquinone disperse dyes for polylactide fibres

1‐Phenyl‐3‐methyl‐5‐pyrazolonyl azo‐anthraquinone dyes having high light fastness on polylactide fibres were synthesised from 1‐aminoanthraquinone via a diazotisation‐coupling reaction with 1‐phenyl‐3‐methyl‐5‐pyrazolones. The structures of these new dyes were confirmed using mass spectrometry, infrared and proton nuclear magnetic resonance spectroscopy and combustion analyses. Their dyeing behaviour on polylactide fibres was also determined, whereupon it was found that the title dyes could be applied at a relatively low dyeing temperature and that the corresponding dyed fabrics had good fastness properties.     

Dispersant‐free dyeing of poly(lactic acid) fabric with temporarily solubilised disperse dyes from azopyridone derivatives

Poly(lactic acid) fibre is derived from annually renewable crops and known to be 100% compostable. In order to extend its environmental friendliness into the dyeing process, dispersant‐free dyeing of poly(lactic acid) fabric with three temporarily solubilised azo disperse dyes based on hydroxypyridone moiety containing a β‐sulphatoethylsulphonyl group was investigated. The dyes were successfully applied to poly(lactic acid) fabric without the use of dispersants. The colour yields of the dyes on poly(lactic acid) fabric were observed to be dependent on dyebath pH and dyeing temperature. The optimum results were obtained at pH 4–5 and 110 °C. One of the dyes showed a colour yield as good as that of a commercial disperse dye and good build‐up on poly(lactic acid) fabric. All of the dyes could be alkali cleared owing to ionisation of the dye under mild alkaline conditions. Wash fastness was good to very good, and light fastness was good. The chemical oxygen demand levels of the poly(lactic acid) dyeing effluent from the dyes were considerably lower than those from a commercial disperse dye.     

2-Pyrazoline Dyes for Wool and Nylon

A range of yellow fluorescent 2-pyrazoline acid dyes has been synthesized. Their spectral and dyeing properties (on wool and nylon) depend both on the nature of the substitution pattern of the dye and on the nature of the fibre substrate. Exhaustion and fastness to washing, which are better on nylon than on wool, are improved by substituents attached to the 2-pyrazoline ring. Fastness to light is independent of the fibre and is increased by substituents on the 4- and 5- positions of the 2-pyrazoline ring. The fastness properties of the pyrazoline dyes were compared with those of C.I. Acid Yellow 7.     

Synthesis and application of KM‐type reactive dyes containing 2‐ethoxy‐4‐chloro‐s‐triazine

A new kind of hetero‐bifunctional reactive dye containing 2‐ethoxy‐4‐chloro‐s‐triazine, with better activity matching with β‐hydroxyethyl sulphone sulphate at a low fixation temperature, was successfully synthesised and characterised. An ethoxy group was designed to be introduced into triazine to increase the substantivity and the reactivity of the dyes. Thereby, the fixation of mono‐s‐chlorotriazine/hydroxyethyl sulphone sulphate (KM‐type) bifunctional reactive dyes on cotton was improved, and dyeing under mild conditions with high fixation was realised. Nineteen dyes with orange, red and blue colours were synthesised and characterised by UV‐Vis and infrared spectroscopy and mass spectrometry. Synthesised dyes were dyed at 60, 75 and 90°C, respectively. Exhaustion and reactivity for all of the ethoxy‐containing KM‐type dyes was over 90% at the optimal temperature, and fixation was over 87%, which was higher than the ethoxy‐free comparative dyes. The optimal fixation temperature of ethoxy‐containing dyes was initially reduced to 75°C, and then to 60°C. Compared with comparative dyes, the wash fastness and light fastness were basically unchanged, and the wet rub fastness of the H‐acid series was reduced by one grade.     

Polymerizable Dyes Part II

Abstract

Arylene bisazo resorcinol dyes IIIa-e were prepared and polycondensed with formaldehyde in the presence of aqueous oxalic acid. The resulting polymeric dyes IVa-e were characterized by yield, melting point, colour, elemental analysis and visible and IR spectroscopy. The thermal properties of polymeric dyes were examined by thermogravimetric analysis. Their dyeing performance on nylon and polyester was assessed. The dyeing on nylon and polyester had yellow, orange, red and brown shades with moderate to good, light and wash fastness. Polymerization of bisazo dyes IIIa-e with formaldehyde on dyed nylon and polyester have also been carried out. The dyeing properties of polymeric dyes were compared with the dyes polymerized on nylon and polyester.     

Synthesis of temporarily solubilised azo disperse dyes containing a β‐sulphatoethylsulphonyl group and dispersant‐free dyeing of polyethylene terephthalate fabric

Disperse dyes containing a β‐sulphatoethylsulphonyl group have temporary solubility and can be applied for dispersant‐free dyeing of hydrophobic fibre. Six novel temporarily solubilised azo disperse dyes having a β‐sulphatoethylsulphonyl group in their structures were synthesised, and their dyeing properties on polyester were investigated. As a dye intermediate, a diazo component having dibromo groups was prepared, and 4‐diethylamino‐4′‐(2‐sulphatoethylsulphonyl‐4,6‐dibromo)azobenzene dyes were prepared by a diazo‐coupling reaction. Then, the dyes containing dicyano groups were prepared by cyanation of corresponding dyes with dibromo groups. The absorption maxima of the dyes were affected by the substituents in the diazo and coupling component rings and varied from 434 to 616 nm in dimethylformamide. Polyethylene terephthalate woven fabric could be dyed with the synthesised temporarily solubilised dyes without using any dispersants. Dyebath pH affected the K/S value at maximum absorption as well as percentage exhaustion on polyethylene terephthalate fabric, and the optimum pH was 5. The dyes gave brownish orange, red, purple, and greenish blue hues on polyethylene terephthalate fabrics, and colour build‐up was good. Wash fastness was good to excellent, rubbing fastness was moderate to excellent, and light fastness was poor to moderate.     

A hemicyanine fluorescent reactive cationic dye: synthesis and applications on wool fabrics

A novel hemicyanine fluorescent reactive cationic dye was synthesised by the reaction between the free amino group of a hemicyanine fluorescent dye and 2,3‐dibromopropionyl chloride. The dye was characterised by proton nuclear magnetic resonance spectroscopy, high‐resolution mass spectrometry, ultraviolet‐visible absorption spectrometry, and single‐photon fluorescence spectrometry. The prepared dye was applied to wool fabrics to give fluorescent orange shades. The colour fastness of the dyed wool fabrics was tested. Results show that dyed fabrics using the novel hemicyanine fluorescent reactive cationic dye could be used as fluorescent clothing.     

Dyeing Properties of Monoazo Disperse Dyes Containing 5- and 6-Aminoindazoles as Diazo Components

In this study the effects of various coupling components, used in conjunction with 5- and 6-aminoindazoles as diazo components, on the spectral characteristics and dyeing properties of dyes for cellulose secondary acetate (acetate), nylon 6 and polyester have been investigated. Eight new disperse dyes suitable for acetate, nylon 6 and polyester were synthesised. In general, when disperse dyes are applied in the dyeing of nylon 6 the colour fastness to water is very low. However, we found that the new dyes synthesised showed good dyeing properties in all cases, on all three fibre types. Some of the dyes obtained using 5- and 6-aminoindazoles gave bright dyeings of good fastness to light, washing, perspiration, dry cleaning and rubbing. Some bright dyeings on polyester were also obtained.