The Light Fastness of Anthraquinone Disperse Dyes on Poly(ethylene terephthalate)

The I.S.O. light-fastness grades of thirty-two anthraquinone disperse dyes on polyester fabric have been determined. High light fastness is exhibited by the 1- and 1,4-hydroxy derivatives and 1- or 1,4-sub-stituted amino derivatives possessing N-substituted electron-withdrawing groups. The 1- and 2-methoxyanthraquinones, 2-hydroxyanthraquinones and all the 2-amino derivatives examined, on the other hand, have poor light fastness. The high light stability of the 1-hydroxy- and 1-anilinoanthraquinones may be due to rapid de-activation of their photo-excited singlet states, while the poor light fastness of the 2-aminoanthraquinones is probably due to their ability to abstract electrons from their environment.     

Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics

Diazotized aryl amines were coupled with 2-aminothiazoles 1 and 2 to give the corresponding thiazolylazo dyes 3 and 4, respectively. 2-Amino-5-arylazothiazoles 5 reacted with chloroacetyl chloride to afford the chloro-acetamide derivatives 6 which further reacted with 2-mercaptobenzothiazole to furnish a new series of 5-arylazothiazolyl dyes 7. The azo structure of the dyes (rather than the tautomeric hydrazo structure) was assessed by ab initio DFT calculations at the B3LYP/6-31G* level. These dyes were applied to polyester fabric as disperse dyes and their fastness properties were evaluated.     

Dyeing of N-modified viscose rayon fibres with acid and metal-complex dyes

Viscose rayon N -modified by the incorporation of polydiallyldimethyl ammonium chloride gave good dye exhaustion and colour yield on dyeing with acid or metal complex dyes. The amount of additive present in the fibre was assessed from its nitrogen content, and percentage exhaustion was found to increase with increasing quantity of additive. Changes in hue, in addition to an increase in the light fastness of deeper shades, are attributed to aggregation of dye within the fibre. The light fastness of metal complex dyes on N -modified fibre was very good but acid dyes gave poor results. Wash fastness was improved after treating with a dye fixing agent.     

The accelerating effect of a small cationic quaternary ammonium compound and the adsorption kinetics in the dyeing of silk with reactive dyes

In order to develop an eco‐friendly method for silk reactive dyeing that uses a lower accelerant dosage to achieve a higher dye fixation, hexyl dimethyl octyl ammonium chloride was synthesised as an accelerant for the dyeing of silk with reactive dyes. The accelerating effect, corresponding adsorption kinetics, and interaction mechanisms among hexyl dimethyl octyl ammonium chloride, reactive dyes, and silk were investigated. At hexyl dimethyl octyl ammonium chloride concentrations of 10.8–14.4 mm , the dye fixations for three reactive dyes were much higher than those achieved with sodium sulfate, even though the required dosages of hexyl dimethyl octyl ammonium chloride were 30–40 times lower than those of sodium sulfate. The wash fastness, rub fastness, light fastness, K/S, and colour difference values after dyeing with hexyl dimethyl octyl ammonium chloride were similar to those obtained using sodium sulfate, and silk can be dyed uniformly. The adsorption kinetics followed a second‐order kinetic model. The activation energies of surface adsorption for the three reactive dyes were lower than those of sodium sulfate. The high fixation of reactive dyestuffs and the low required dosage of hexyl dimethyl octyl ammonium chloride demonstrate that the use of this new accelerant provides a novel, highly efficient method for silk dyeing. A possible acceleration mechanism of hexyl dimethyl octyl ammonium chloride for reactive dyes adsorbed on the surface of silk was proposed, based on a series of activation parameters of the adsorption process.     

Studies of novel water-soluble colored polyesters containing azo moiety

A series of water-soluble colored polyesters (polymeric dyes) were synthesized by interfacial polycondensation reaction of terephthaloyl chloride and various bisazodiols (monomeric dyes) that were derived from diarylidene cyclopentanone and diarylidene cyclohexanone by coupling with various diazonium salts of anthraquinone dyes containing the sodium salts of the sulfonic acid group. All the colored polyesters were characterized by their elemental analysis, IR and UV-visible spectroscopy, viscometry, solubility, and TGA. Color and dyeability of the polymeric dyes are discussed by comparing them with those of the corresponding monomeric dyes. The color fastness of the polymeric dyes show fair to very good fastness to light and very good to excellent fastness to washing, rubbing, perspiration, and sublimation. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 68: 2041–2048, 1998     

Pretreatment of cotton with poly(vinylamine chloride) for salt-free dyeing with reactive dyes

Poly(vinylamine chloride) has been investigated as a pretreatment for the salt-free dyeing of cotton with reactive dyes. Dye fixation was found to be much higher than by conventional dyeing without pretreatment, even in the presence of a large amount of salt. The influence of pretreatment conditions on dye fixation, such as pad–bake variables and the concentration of poly(vinylamine chloride), has been studied. The dyeing behaviour of CI Reactive Red 2 on pretreated cotton was examined and found to follow a Langmuir-type adsorption curve. Dyed cotton pretreated with poly(vinylamine chloride) showed excellent wash fastness and good rub fastness. It is concluded that poly(vinylamine chloride) is effective as a pretreatment for salt-free dyeing with reactive dyes.     

γ-Radiation induced graft copolymerization of N-phenyl- and N-p-hydroxyphenyl maleimide onto cotton fabrics

The graft copolymerization of N-phenylmaleimide and its p-hydroxy derivative onto cotton fabric using γ-radiation was studied. The effects of monomer concentration, dose rate, and irradiation time have been investigated. The surface topology, the x-ray diffraction, and the thermal stability of the modified fabric also were studied. In addition, the dyeing characteristics of the grafted fabrics when dyed with basic dyes together with the color fastness of these dyes towards UV radiation were investigated.     

Improving the environmental and economic aspects of cotton dyeing using a cationised cotton†

One approach to improve the affinity of anionic dyes for cotton is to add cationic dye sites to the fibre. The dyeing behaviour of cotton that had been rendered cationic by reaction with 2,3‐epoxypropyltrimethylammonium chloride was examined. Dye yields and fastness properties are reported for a number of direct, reactive and acid dyes with the modified fibre. Excellent dye yields and colour fastness properties were obtained without the use of electrolytes, multiple rinsings or fixation agents which are normally employed in cotton dyeing.     

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。     

Photoconductivity and Fading

The conductivity of purified films of the eight dyes used in the ISO Light-fastness Test have been studied both in the dark and under illumination by the visible and ultra-violet radiation from a mercury vapour lamp. All eight dyes behaved as n-type semiconductors and additionally those of light fastness ratings five and above showed p-type semiconduction. All the dyes also behaved as photoconductors and the activation energies of photoconduction were between one third and one fifth of those for semiconduction. Very rapid response to illumination was shown by the dyes of highest light fastness. Although the dyes were of five different chemical types, some tentative rules relating properties to light fastness can be formulated. These are: (1) Dyes should show p-type and n-type semicon-ductivity. (2) Response time of photo-conduction should be short. (3) In the case of dyes of similar structure, higher activation energies for photoconduction favour higher light fastness.     

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.     

铁金属络合偶氮染料的合成研究

Some novel 1:1 and 1 ：2 Fe complex azo dyes were synthesized in this study.The mass spectrum analysis of 1:1 and 1:2 Fe complex azo dyes is presented.Lightfastness,rubbing fastness and washing fastness of these metallized complex dyes were evaluated for use on wool.Results show that these dyes are of good lightfastness and satisfactory brown shades.     

新型活性染料染锦纶用匀染剂的研制

采用正交试验法、对比试验法,合成了两性表面活性剂作为锦纶染色用匀染剂。结果表明：在温度90℃、时间3 h的酯化反应条件和牛脂胺聚氧乙烯（T15）醚的酯化产物与氯化苄反应物摩尔比为1∶1,反应温度为80℃、反应时间为5 h的季胺化反应条件下合成的匀染剂用于锦纶染色中,解决了锦纶染色不匀的问题,提高了活性染料染色的牢度及染色上染率。     

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.     

New azodisperse dyes with thiazole, thiophene, pyridone and pyrazolone moiety for dyeing polyester fabrics

New antipyrinylazo dyes were prepared by diazocoupling of 4-antipyrinyl diazonium chloride with a variety of coupling components e.g. thiazole, thiophene, pyridone, and pyrazole moieties. The synthesized dyes were characterized by UV-visible absorption, IR, ¹H NMR, and MS spectroscopy. These dyes were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates (L*, a*, b*, H*, C*) was assessed.     

高分子染料在纤维染色中的研究进展

在纤维染色中,染料可以分为反应性高分子染料,分散高分子染料及酸性高分子染料等。这些染料具有各自鲜明的染色性能特点,如反应性高分子染料可与纤维以共价键结合而染色,分散性高分子染料与纤维有很好的相容性,酸性高分子染料可与相应的单体染料具有相同的染色性能但热稳定性更好。本文介绍了各类高分子染料的结构特点及在纤维染色中的应用情况。有24篇参考文献。     

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.     

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.     

活性染料对莲纤维的染色性能研究

为了了解活性染料对莲纤维的染色性能,采用单因素分析法,在改变温度、浴比、时间、元明粉浓度、纯碱浓度等工艺条件下,分别采用两种不同类型的活性染料对莲纤维进行染色,并测试其上染率、固色率、耐皂洗色牢度和耐汗渍色牢度。结果表明:活性大红X-3B上染莲纤维的最佳染色工艺为染色温度40℃,染液浴比1∶40,染色时间60 min,元明粉质量浓度20 g/L,纯碱质量浓度30 g/L;活性嫩黄X-7G上染莲纤维的最佳染色工艺为染色温度40℃,染液浴比1∶50,染色时间60 min,元明粉质量浓度10 g/L,纯碱质量浓度20 g/L;活性染料耐皂洗色牢度和耐汗渍色牢度都在3级以上。     

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.