Substituent effects on the colour,dyeing and fastness properties of 4-phenylazo-1-naphthylamines and of 2-acetylamino-5-methoxy-4-N-ß-cyanoethyl-N-ß-hydroxyethylaminoazobenzene

The synthesis of a series of blue disperse dyes obtained by diazotisation of substituted anilines and coupling with 2-acetylamino-5-methoxy-4-N-ß-cyanoethyl-N-ß-hydroxyethylaniline and to N-ß-hydroxyethyl-1-naphthylamine is described. Substituent effects on the colour of the dyes is discussed, with particular respect to analogous dyes derived from 4-N-ß-cyanoethyl-N-ß-hydroxythylaniline. Some dyes from trisubstituted anilines as diazo component colour polyester in deep blue shades of generally good fastness properties.     

Iodo-substituted 4-aminoazobenzenes and 4-phenylazonaphthylamines-dyes for synthetic-polymer fibres

2-Iodo-4-nitroaniline, 2,6 diiodo-4-nitroaniline, 6-iodo-2,4-dinitroaniline and 2-cyano-6-iodo-4-nitroaniline were prepared from the appropriate nitroanilines by various iodination procedures. Diazotisation of these, and coupling to N-ß-cyanoethyil-N-ß-hydroxyethylaniline, 2-methoxy-5-acetylamino-N-ß-cyanoethyl-N-ß-hydroxyethylaniline and N-ß-hydroxyethyl-1-naphthylamine afforded a series of red to blue disperse dyes. The colour, dyeing and fastness properties of the dyes are evaluated with respect to analogous fluoro-, chloro-and bromo-substituted derivatives.     

Structure—wet fastness relationships of some blue disperse dyes for polyester

A range of monoazo blue disperse dyes has been synthesised by coupling benzenoid and heterocyclic diazo components to aniline derivatives containing ester functions. The colour properties and wet fastness of the dyes on polyester at 1/1 standard depth have been examined and rationalised in terms of dye structure. Styryl dyes have also been prepared in order to compare their wet fastness properties to those of the azo dyes.     

Dyestuffs for synthetic polymer fibres: 4-N-morpholinoazobenzenes

A series of monoazo disperse dyes derived from the coupling to N-phenylmorpholine of diazotised anilines and aminothiazole derivatives is described. The colour, dyeing and fastness properties of the dyes is compared to those of the analogous dyes based on N-ethyl-N-β-hydroxy-ethylaniline. Dyes from the ring closed heterocyclic coupling components dye synthetic-polymer fibres in deep colours of good fastness properties and show significant hypsochromic colour shifts compared to the uncyclised derivatives.     

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.     

Disperse dyes: hetarylazo derivatives from dichloro-2-aminobenzothiazoles

The synthesis of 4,5-, 4,6-, 4,7- and 5,7-dichloro-2-aminobenzothiazoles is reported. Diazotisation of these and coupling to N-substituted anilines affords orange-red to blue dyes which have excellent coloration and good light fastness properties on polyester. The colour of the dyes is discussed with respect to the orientation of the chloro substituents and compared also with dichloro-4-aminoazobenzene analogues and to established colorants based on 5,6(6,7)-dichloro-2-aminobenzothiazole.     

High fastness heterocyclic azo disperse dyes bearing ester functions

Blue monoazo disperse dyes bearing carboxylic acid ester functions have been synthesised from thiophene diazo components in the search for colorants of high fastness and reduced environmental impact. The colour properties of the dyes in solution and on polyester, as well as the fastness of the dyes when applied to polyester, are examined and rationalised in terms of dye structure.     

Synthesis and properties of acid dye derivatives of arylsulphonanilides

Thirty-five acid dyes suitable for dyeing wool and polyamide fibres were synthesized, using derivatives of arylsulphonanilides prepared from o-nitrotoluene or chloronitrotoluene. As coupling components, derivatives of 1-phenyl-3-methylpyrazolone-5 and 2-naphthol were used. Fastness and colour properties of the prepared dyes were determined. It was found that some of the prepared dyes on polyamide fibres show batho- and hypso-chromic effects as well as hypo- and hyper-chromic effects during testing of their fastness to washing and to acid and alkaline perspiration. Spectroscopic examinations and determination of pK_a of the sulphonamide and hydroxyl groups of the dyes showed that the observed changes are associated with aggregation or disaggregation of the dyes on fibres or with a change in the azo-hydrazone equilibrium. Some of the prepared dyes are characterized by very good dyeing and fastness properties.     

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.     

Synthesis and Electronic Spectra of some 4–Aminoazobenzenes

The synthesis of a range of monoazo disperse dyes prepared from monosubstituted anilines as the diazo components is reported The absorption maxima of the dyes are recorded, and shifts resulting from the effect of different substituents in both the diazo component and the coupling component are correlated with the nature of the substituent. The use of monosubstituted aniline; as diazo components, coupled to different TV–substituted anilines, can result in dyes with λD_max differing by about 100 nm.     

偶氮型分散染料结构与应用性能关系的研究

以2—氨基—3,5—二硝基噻吩和3—硝基—4—氨基笨甲酸甲酯为重氮组分,与不同的偶合组分偶合,合成了12只分散染料。测试了合成的染料和参比商品染料的应用性能。结果表明,合成的12只分散染料均具有良好的湿处理牢度、耐摩擦牢度及耐升华牢度,且优于参比商品染料。重氮组份相同时,偶合组分上带有双酯结构的染料,其湿处理牢度好于带有双乙酰氧乙基的染料。     

Synthesis and characterization of hetarylazo disperse dyes derived from substituted N‐β‐acetoxyethylanilines—Application on cellulose acetate

The heterocyclic amines 2‐amino‐6‐methoxy‐ and 2‐amino‐6‐nitrobenzothiazole, 3‐amino‐5‐nitro‐[2,1]‐benzisothiazole, and 2‐amino‐3,5‐dinitrothiophene were diazotized and coupled to substituted N‐β‐acetoxyethylanilines to give dyes which colored cellulose acetate in red to deep blue hues. The color of the dyes is discussed with respect to the nature of the heterocyclic ring and to the substituents in the diazo and coupling component. Dyeing and fastness properties of the dyes on cellulose acetate are also reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 3479–3483, 2004     

Azo dyes based on naphtholic oligomers

A series of oligomeric azo dyes has been prepared by coupling various diazonium salts of benzothiazoles to 1-naphthol/formaldehyde (1-NF) and 2-naphthol/formaldehyde (2-NF) oligomers. They were characterised in terms of their softening point, yield, colour, solubility and UV-VIS spectra. Structure-property relationships are discussed. Dyeing on polyester, nylon-6,6, and wool resulted in orange to red coloration having excellent light and washing fastness properties.     

The influence of methyl groups on the colour and dyeing properties of acid dyes derived from 1-amino-4-bromo-anthraquinone-2-sulphonic acid and arylamines

Four blue acid dyes were synthesized by condensation of bromamine acid with aniline, 2,4-dimethylaniline, 2,6-dimethylaniline and 2,4,6-trimethylaniline. It was found that the number and orientation of the methyl groups on the 4-phenylamino substituent affected both the colour and dyeing properties of the dyes. The more methyl groups present, the higher was the dye uptake and the better the fastness to wet treatments. When a methyl group is present in the ortho position of the phenylamino group, the hue of the dyes is hypsochromically shifted.     

噻吩型偶氮分散染料的合成与应用性能研究

合成了六只蓝色噻吩型偶氮分散染料,并测试了染料的应用性能.讨论了染料的湿处理牢度等应用性能与染料分子结构的关系.结果表明,合成的六只分散染料具有良好的湿处理牢度、耐摩擦牢度及耐升华牢度;重氮组份相同时,偶合组分上带酯基结构的染料,其湿处理牢度优于带有乙酰氧乙基的染料.     

Monoazo disperse dyes. Part 3; Synthesis and fastness properties of some novel 4,5-disubstituted thiazolyl-2-azo disperse dyes

Novel blue disperse dyes bearing a 5-nitro substituent on various C-4 substituted thiazolyl-2-azo dyes have been prepared using m -aminoacetanilide derived coupling components. These dyes have been characterised using a range of spectroscopic techniques and exhibit interesting fastness behaviour on dyed polyester. For Parts 1 and 2 in this series, see references 9 and 10, respectively.     

Synthesis of yellow pyridonylazo colorants and their application in dye–pigment hybrid colour filters for liquid crystal display

Nine yellow azo dyes were designed and synthesised by using different diazo components and pyridonyl coupling components for application in dye–pigment hybrid colour filters for liquid crystal displays. The synthesised dyes were characterised by proton nuclear magnetic resonance and elemental analysis. The thermal stability was examined by thermogravimetric analysis, and solubility was estimated in industrial solvents such as N-methyl-2-pyrrolidone and propylene glycol methyl ether acetate. The dyes, which exhibited suitable physical properties for use in a dye–pigment hybrid colour filter, were fabricated into colour filters, and their optical properties were measured.     

Coloration properties and clearability of phthalimide‐derived monoazo disperse dyes containing ester groups

The coloration properties and clearability of disperse dyes prepared from phthalimide‐derived diazo components and a coupling component containing two carboxylic acid ester groups have been investigated. Members of the series featured C₂–C₄ alkyl substituents on their phthalimidyl nitrogen atom. The nature of the N‐alkyl group made no consistent difference to dye uptake on polyester. No correlation was found between percentage exhaustion and calculated solubility parameters. Wash fastness was extremely good. Comparison with analogues indicated that the diester motif was of significant extra benefit to wash fastness for phthalimide‐derived dyes, but did not increase photostability above the lower range of commercial acceptability. Clearability was compared with that of dyes lacking one or both hydrolysable structural features, as well as with that of some industrial dyes. The novel dyes exhibited a greater tendency to be solubilised, consistent with hydrolysis of their ester and/or phthalimide functionalities.     

Substitutes for 1-naphthylamine. Part 3-disazo direct dyes with 3-amino-4-methoxyacetanilide and 1-naphthylamine components

A parallel series of dyes using 3-amino-4-methoxy acetanilide and 1-naphthylamine as intermediate components, and 6-(N-phenyl)-amino-1-naphthol-3-sulphonic acid as a coupling component, together with some well known disazo components, have been synthesised and compared in order to identify effective substitutes for 1-naphthylamine.     

合成纤维及其混纺织物用染料的研究(Ⅳ)偶氮型活性分散染料结构与性能的关系

本文合成了以对-(β-羟乙基砜硫酸酯)苯胺、2-氨基-6-(β-羟乙基砜硫酸酯)苯骈噻唑为重氮组分,以不同取代端氨基苯胺为偶合组分的2个系列偶氮型活性分散染料.探讨了这些染料的分子结构与其在涤-棉混纺织物上分配的关系;与染料吸收光谱的关系;与涤、棉两组分上颜色的关系及与染色织物耐晒牢度的关系.