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.     

Evaluation of colour fastness and thermal migration in softened polylactic acid fabrics dyed with disperse dyes of differing hydrophobicity

This paper addresses the relative effects of softeners having different properties and their method of application (exhaust vs pad) on the colour fastness of poly(lactic acid) fabrics dyed with a range of disperse dyes with different levels of hydrophobicity. A comparison was made with a correspondingly finished polyethylene terephthalate fabric. Possible relationships between the levels of hydrophilicity/hydrophobicity of the dye, and softener, and the colour fastness were explored. Finally, the amount of dye thermally migrated into the finish on the softened poly(lactic acid) and polyethylene terephthalate fabrics was examined in comparison with their colour fastness. Softened poly(lactic acid) fabrics dyed with CI Disperse Red 167.1 exhibited more thermal migration, and hence lower colour fastness, than the corresponding polyethylene terephthalate fabrics. Conversely, softened poly(lactic acid) fabrics dyed with Dianix Deep Red SF exhibited less thermal migration, and hence better colour fastness, than the corresponding polyethylene terephthalate fabrics. Overall, no clear relationship was found between the hydrophobic nature of the disperse dye and the hydrophobic character of the softener on the colour fastness.     

Dyeing poly(lactic acid) fibres in supercritical carbon dioxide

A study has been conducted into the dyeing of poly(lactic acid) fibres in supercritical carbon dioxide. The fibres were completely dyed using disperse dyes at 50 °C as shown by fibre cross-sections, although high colour depths in dark shades still prove challenging. Dye uptake increased significantly at temperatures ≥80 °C. At 95 °C in supercritical carbon dioxide, shrinkage and hardening of raw poly(lactic acid) were observed which could partly be overcome by the supercritical carbon dioxide extraction step. Afterclearing with cold supercritical carbon dioxide (to remove unfixed dye after dyeing) decreased the colour depth and led to non-uniform dyeing results on poly(lactic acid). Wash and rub fastness was good to very good also when poly(lactic acid) was not aftercleared in supercritical carbon dioxide. Fibre damage and elongation at break in supercritical carbon dioxide were similar to water.     

One‐step dyeing of polyethylene terephthalate fabric,combining pretreatment and dyeing using alkali‐stable disperse dyes

In the conventional dyeing process, polyester and its blended fabrics are usually dyed in a weak acidic medium. In order to reduce cost and improve production efficiency, a new dyeing method – one‐step dyeing of polyethylene terephthalate fabrics, combining pretreatment and dyeing in alkali conditions – was investigated. The alkali‐stable disperse dyes Red 900, Red 902, Yellow BROB and Blue 825 were used to dye polyethylene terephthalate fabrics. The dyeing properties of polyethylene terephthalate fabrics in the case of one‐step dyeing at various pH values or sodium hydroxide concentrations were discussed in terms of colour yield, colour parameters and fastness. The performance of one‐step dyeing using alkali‐stable disperse dyes was excellent. The dyed fabric had good fastness. Wet processing could be combined and shortened. One‐step dyeing of polyethylene terephthalate fabrics could reduce the consumption of water and energy and improve production efficiency. One‐step dyeing of polyethylene terephthalate has potential application in cleaner textile production.     

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.     

Thermal migration of selected disperse dyes on poly(ethylene terephthalate) and poly(lactic acid) (Ingeo†) fibres

A study has been carried out to correlate the wet fastness properties of dyed knitted fabrics, derived from both poly(ethylene terephthalate) and poly(lactic acid) (Ingeo) fibres, with the thermal migration properties of the disperse dyes during heat treatment. The results indicate a greater amount of disperse dye at the surface of the Ingeo fibre fabric than the poly(ethylene terephthalate) fabric, after post heat‐setting using the conditions needed for fabric stabilisation, correlating well with its slightly lower wash fastness properties.     

Dyeing of poly(lactic acid) fibres with synthesised novel heterocyclic disazo disperse dyes

Poly(lactic acid) (PLA) is the first melt‐processable, renewable, sustainable and biodegradable natural‐based synthetic fibre. It has a broad range of uses and combines ecological advantages with outstanding performance in textiles. PLA fibre, as an aliphatic polyester, can be dyed with disperse dyes. Apart from the limited number of commercial disperse dyes, disperse dye exhaustion on PLA is generally lower than that on  poly(ethylene terephthalate) (PET). In this study, new heterocyclic disazo disperse dyes, substituted with methyl, nitro and chloro groups at their ortho‐, meta‐ and para‐ positions, synthesised in our previous study, were applied to PLA and PET fibres to examine their dyeing performance, and colour fastness and dye exhaustion properties. Different shades of yellow, orange, reddish brown and brown were obtained. Most of the synthesised novel heterocyclic disazo disperse dyes exhibited good build‐up properties with high K/S levels on both fibres. Para‐ bonding substituent provided higher K/S values than meta‐ and ortho‐ positions for –NO₂ and –Cl substituents for both fibres. Overall, the most synthesised novel heterocyclic disazo disperse dyes in this study exhibited good build‐up properties with high K/S, exhaustion and wet fastness levels on both PLA and PET fibres.      

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.     

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 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.     

Improving the dyeability of polyimide by pretreatment with alkali

Polyimide fabric, as a high‐performance fabric, possesses advantageous properties, such as outstanding thermal stability and chemical resistance, but has poor dyeability. In this paper, polyimide fabric was dyed successfully with disperse dyes by high‐temperature and high‐pressure dyeing in the presence of a swelling agent and auxiliaries. Under optimal dyeing conditions, it is pretreated with NaOH 6 g l^?1 and dyed with disperse dyes 5% o.w.f., NaCl 1 m , benzyl alcohol 60 ml l^?1 at 135 °C for 45 min to obtain a satisfactory colour yield with good washing fastness and dry rubbing fastness with 93.3% strength retention. The experimental results demonstrate that the Nernst adsorption isotherm is a favourable model for polyimide fabric dyeing with disperse dyes.     

The dyeing of nylon with a microencapsulated disperse dye

Melamine resin microcapsules containing CI Disperse Blue 56 were prepared by in situ polymerisation. The microcapsules were characterised by their thermal properties and morphology, such as particle size and particle size distribution. The dyeing behaviour of the microcapsules on nylon 6.6 was evaluated. The microencapsulated dye exhibited good build-up, levelness and fastness properties. It has been demonstrated that microencapsulated disperse dye can be used to replace commercial disperse dyes in dyeing polyamide fabric without dyeing additives, and the resulting effluent can be easily recycled after filtration.     

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.     

Deep‐coloured polyester/cotton blends with low concentrations of polymethylol dyes by a one‐pass continuous dyeing process

An obvious limitation of the one‐pass continuous dyeing process for polyester/cotton blends is its inability to achieve deep colour depth, which is caused by the low dye fixation yields of commercial reactive dyes. In this study, the performances of polyester/cotton blends dyed with high‐fixation polymethylol dyes and disperse dyes were compared with those of polyester/cotton blends dyed with a mixture of reactive dyes and disperse dyes. Polymethylol dyes were observed to be suitable for dyeing polyester/cotton blends when used in low concentrations; the required concentrations of polymethylol dyes were only 23–58% of the concentrations of commercial reactive dyes required to reach a given colour level on polyester/cotton blends. The wash and crocking fastness of polyester/cotton blends dyed with polymethylol dyes were similar to those of polyester/cotton blends dyed with reactive dyes.     

Electrostatic self‐assembly dyeing of cotton fabrics

A new approach to the dyeing of cotton fabrics using an electrostatic self‐assembly method was evaluated. Cotton fabrics were pretreated with 2,3‐epoxypropyltrimethylammonuium chloride and cationic charges were produced on the fabric surfaces. For the dyeing of cotton fabric, reactive and acid dyes were used. Oppositely charged anionic reactive/acid dyes and cationic poly(diallyldimethylammonium chloride) were alternately deposited on the surface of cationised cotton fabrics. Ten multilayer films of dye/poly(diallyldimethylammonium chloride) were deposited on the cotton fabric surfaces using a padder. The build‐up of the multilayer films and the level of colour strength (K/S) achieved are discussed. Samples of cotton fabrics were also dyed with the same dyes, but using the exhaust method, and both types of dyed samples were compared. The washing, rubbing and light fastness properties were evaluated for the dyed fabrics.     

Investigation of alkaline hydrolysis of phthalimide‐based azo dye and its application to after‐treatment optimisation for high‐fastness dyeing of polyesters

4‐Amino‐N‐methylphthalimide was prepared from phthalimide for use as a diazo component and was coupled with N,N‐Diethylaniline to produce a phthalimide‐derived monoazo disperse dye. The pseudo first‐order kinetics were confirmed by analyzing the dye hydrolysis under alkaline conditions using high performance liquid chromatography, and the optimal dyeing pH and alkali‐clearing conditions were proposed. The synthesised phthalimidyl disperse dyes exhibited excellent colour fastness with a mild alkaline after‐treatment instead of reduction clearing which results in a high biological oxygen demand and pH in conventional disperse dyeing wastewater.     

Improvement of the dyeing and fastness properties of a naphthalimide fluorescent dye using poly(amidoamine) dendrimer

In this study, 4‐amino‐9‐methoxypropylnaphthalimide fluorescent dye (dye 1 ) was reacted with poly(amidoamine) dendrimer G = ?0.5 to prepare a naphthalimide–dendrimer hybrid dye (dye 2 ). The chemical structures of the synthesised dyes were confirmed by elemental analysis, Fourier transform infrared spectroscopy, ¹H nuclear magnetic resonance spectroscopy, and ultraviolet‐visible spectroscopy. The solvatochromism of the dyes was evaluated in various solvents with respect to visible absorption properties, and positive solvatochromism was observed by solvent polarity change from chloroform to ethanol. The dyeing ability of the synthesised dyes was investigated by their application onto nylon fabric, and nylon substrates dyed with dye 2 exhibited marked enhancement both in terms of colour strength and general fastness properties. The results of this study clearly demonstrated the high potential and performance of dye 2 as a novel promising fluorescent dye as compared with dye 1 . Overall, it was inferred that the modification of the naphthalimide fluorescent dye with poly(amidoamine) denderimer could markedly improve the dyeing and fastness properties of the naphthalimide fluorescent dye on nylon fabrics.     

Ozone applications for after‐clearing of disperse‐dyed poly(lactic acid) fibres

In this study, the effectiveness of the ozonation process, in neutral distilled water at room temperature, as a clearing process for disperse‐dyed poly(lactic acid) fibre fabrics is investigated. The efficiency of simultaneous decolorisation of dyebath effluent and clearing of dyed poly(lactic acid) in the cooled dyebath after completion of the poly(lactic acid) dyeing cycle is also explored. Conventional alkaline reduction clearing with sodium dithionite was chosen as a control clearing process for comparison. Wash fastness, colour difference, colour removal (in Hazen) and chemical oxygen demand values were determined and compared. Long ozone treatment times at high ozone dose resulted in unacceptable colour differences. The colour difference problem was solved by use of lower ozone dose; however, a warm soaping step had to be added to the after‐clearing sequence in order to achieve the desired fastness properties. A 33% reduction on the chemical oxygen demand load of the total process (dyeing + after‐clearing) could be achieved by ozone after‐clearing instead of using a conventional reduction clearing treatment. The addition of the warm soaping step to improve the fastness properties of the ozonated samples increased the total chemical oxygen demand of the process (dyeing + ozonation in water + warm soaping), but a 12–18% reduction on the chemical oxygen demand load of the total process was observed when compared with the conventional treatment sequence (dyeing + reduction clearing).     

Dyeing and fastness properties of phthalimide‐based alkali‐clearable azo disperse dyes on poly(ethylene terephthalate)

The properties of a series of phthalimide‐containing azo disperse dyes and azo dyes with N‐methyl phthalimide moieties in their diazo component were investigated and compared when used to colour polyethylene terephthalate. The N‐substitution of the phthalimide gave a hypsochromic effect on the colour change and better colour yields on poly(ethylene terephthalate) fabrics, probably because of the electron‐donating property of the methyl group and the higher hydrophobicity of phthalimide‐containing azo dyes compared with those containing phthalimide moieties. The results show that phthalimide‐based azo disperse dyes have excellent dyeing fastness properties and that high wash fastness can be achieved using alkali clearance. This alternative clearance method is important for reducing the environmental impact of the dyeing process by replacing reductive clearing and, in particular, by removing the need for sodium hydrosulphite, which creates a high biological oxygen demand when released in conventional disperse dyeing effluent and which generates aromatic amines.     

聚对苯二甲酸丙二酯纤维的染色性能

根据Shell公司和Dystar公司的研究,用Optidye系统从分散染料吸附与上染率、染色温度、pH值、匀染性及染色牢度等方面解析了聚对苯二甲酸丙二酯(PTT)纤维的染色性能。PTT纤维在100℃就可染到深色,在60～80℃和90～100℃有两个吸附速度较快区域;PTT纤维属易染型纤维,在最高温度染保持30～40min即可。高温型分散染料在120℃染色,常压100℃染色无需pH值调节。分散染料染色牢度(洗涤、摩擦及耐光)非常好。