Thiophene Based Monomeric and Polymeric Disperse Dyes for Hydrophobic Fibres

Abstract

Eight monomeric dyes have been prepared by coupling 2-amino-3-carbethoxy-4,5-dimethylthiophene with various N-phenylmaleimides. Polymeric dyes have been prepared by free radical polymerization of monomeric dyes and they are characterized by IR spectra, Intrinsic viscosity, molecular weight by Vapour Pressure Osmometry, thermogravimetry analysis and elemental analysis. The monomeric dyes have been also characterized by IR spectral studies and elemental analysis. All the dyes were applied as a disperse dyes on nylon and polyester fibres. The dyed fibres showed fair to good fastness to light on nylon and fair fastness on polyester. The washing, rubbing, perspiration and sublimation fastness properties of the dyed fibres has been found to be very good to excellent.     

Dyeing of natural and synthetic textiles in supercritical carbon dioxide with disperse reactive dyes

Polyester, nylon, silk and wool were dyed with disperse reactive dyes in supercritical carbon dioxide (scCO₂). The dyes were substituted with either vinylsulphone or dichlorotriazine reactive groups. Since earlier research showed that water, distributed over the scCO₂ and the textile, increased the colouration, experiments were done with the vinylsulphone dye with varying amounts of water in the dyeing vessel, to investigate if there is an optimum water concentration. The amounts were such, that no liquid water was present. The maximum colouration was obtained when both the scCO₂ and the textiles were saturated with water. At the saturation point, deep colours were obtained with the vinylsulphone dye for polyester, nylon, silk and wool, with fixation percentages between 70 and 92% when the dyeing time was 2 h. The positive effect of water was due to its ability to swell fibres or due to an effect of water on the reactivity of the dye–fibre system. Also the dichlorotriazine dye showed more colouration when the scCO₂ was moist. With this dye, experiments were conducted in water-saturated scCO₂, varying the pressure from 225 to 278 bar and the temperature from 100 to 116 °C. The colouration of polyester increased with pressure, the results for silk and wool were not sensitive to pressure. Increasing the temperature had no influence on the dyeing of polyester, silk and wool. The fixations on polyester, silk and wool, being between 71 and 97%, were also independent of pressure and temperature.     

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.     

Solvent-assisted Dyeing of Nylon 6.6 and Polyester Fibres

The results of laboratory semi-bulk and bulk trial work on the dyeing of nylon 6.6, with anionic dyes in the presence of n-butanol, in an aqueous dyebath are described. The method gives improvements in coverage of barre which cannot be achieved in other ways, without detectable adverse effects on the physical properties of the nylon 6.6 or the colour and fastness properties of the dyes. Results of work by a similar, solvent-assisted dyeing method for polyester fibre are given. Improvements in migration and speed of fixation of dye in the presence of n-butanol are noted, but these are similar in magnitude to the improvements obtainable with conventional carriers for polyester dyeing at much lower concentrations. The method is likely to be commercially viable only if a substantial proportion of the butanol added to the dyebath can be recovered for re-use. This should theoretically be possible, but experimental confirmation of the process has not yet been obtained.     

Dyeing Properties of Monoazo Dyes Derived from Substituted 2-Aminobenzothiazole-3N-oxides on Various Synthetic-polymer Fibres

The preparation of new monoazo dyes from substituted 2-aminobenzothiazole-3N-oxides and aniline coupling components and their dyeing properties on polyester, cellulose acetate, nylon 6 and acrylic fibres are reported.     

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.     

Studies of novel monomeric and polymeric azo disperse dyes

A series of polymeric dyes were synthesized by free‐radical addition polymerization of monomeric dyes that were derived from diazotized 2‐amino‐3,5‐bis‐(ethoxycarbonyl)‐4‐methylthiophene by coupling with various N‐arylmaleimides. All the polymeric dyes were characterized by elemental analysis, IR and visible spectroscopy, viscometry, and TGA. Color and dyeability of the polymeric dyes are discussed by comparing them with those of the corresponding monomeric dyes. All the dyes have been found to give various color shades with good to very good depth and levelness on the fiber. The dyeing of the monomeric dyes shows good fastness to light and very good to excellent fastness to washing, perspiration, sublimation, and solvents. The corresponding polymeric dyes show excellent fastness properties. The percentage dyebath exhaustion and fixation on the fiber have been found to be good to very good (60–90%). © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 84: 1380–1389, 2002; DOI 10.1002/app.10276     

Preparation and properties of water‐soluble polyester surfactants. II. Preparation and surface activity of silicone‐modified polyester surfactants

We prepared a novel series of water‐soluble silicone‐modified polyesters [poly(ethylene glycol) (PEG)–silicone polyesters] by reacting organopolysiloxane with a hydroxy‐terminated polyester. The polyesters were obtained by the polymerization of maleic anhydride and PEGs (molecular weights = 2000, 4000, 6000, 8000, and 10000). These water‐soluble PEG–silicone polyesters can be used as auxiliaries in dyeing process because they exhibit good surface activities such as surface tension, low foaming, and wetting power. The presence of these surfactants also retarded the rate of nylon dyeing with acid dyes. The retarding effect and low‐foaming property of these novel PEG–silicone polyesters make it possible for these surfactants to be used as leveling agents for modern nylon dyeing with acid dyes. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 3005–3012, 2002     

2-Aryl Azo Benzothiazole Resorcinol Formaldehyde Oligomer Dyes

Abstract

A series of Oligomenc azo dyes has been prepared by coupling various diazonium salt of Benzothiazols to Resorcinol-formaldehyde(RF) oligomer. They were evaluated in terms of their softening pointes, yield, colour, solubility and U.V.-Visble spectra. Structure property relationships are discussed and dyeing on polyester PET, Nylon-6,6 and wool assessed. Dyeing on polyester, Nylon-6,6 and wool resulted in yellow, Orange and brown to red colourations having excellent fastness to light and washing.     

Alkaline dyeing of polyester and polyester/cotton blend fabrics using sodium edetate

An alkaline dyeing of polyester with an alkali‐stable disperse dye, Dianix® Scarlet AD‐RG, was developed using sodium edetate as an alkaline buffering agent. The results obtained indicate the suitability of using sodium edetate for alkaline dyeing of polyester when compared with the control alkaline dyeing using Dianix AD system. Selected mono and bifunctional reactive dyes were used in combination with the alkali‐stable disperse dye for dyeing of polyester/cotton blend. Different dyeing methods for cotton and polyester/cotton blend fabrics using sodium edetate were evaluated in comparison with their respective control alkaline dyeing methods. The results of using sodium edetate in one‐bath two‐stage and two‐bath dyeing of polyester/cotton blend were comparable with that of the control dyeing method. Particularly, no change in the leveling and fastness properties was evaluated for all samples irrespective of the dyeing method. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

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.     

Disperse dyeing of polyester fibers: Kinetic and equilibrium study

The effect of temperature on the dyeing rate constant k, diffusion coefficient D, and time of half‐dyeing t_1/2 was evaluated for the dyeing of polyester fibers with two disperse dyes, an azo and an anthraquinone dye. Activation energies of diffusion E were calculated. The polyester dyeing equilibrium was also studied and the partition coefficient K and standard affinity Δμ° at various temperatures were determined for the anthraquinone dye. Standard enthalpy ΔH° and standard entropy ΔS° of dyeing were also obtained. The same equilibrium parameters were not obtained for the azo dye because of its dyeing behavior. A similar kinetic and equilibrium study was made for the pure azo and anthraquinone compounds free from the dispersing agents present in the commercial dyes and the results are discussed. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 123–128, 2002     

Effects of additives on the dyeing of polyamide fibres. Part I: β-cyclodextrin

A series of 12 dyes were synthesised and used for the dyeing of nylon 6 and 6,6. β-Cyclodextrin was tested as a low environmental impact additive in dyeing processes. Interactions between dyes and β-cyclodextrin were studied by means of solubility isotherms, TGA and DTA analysis. β-Cyclodextrin showed good levelling properties in the dyeing of polyamide fibres. The observed effect can be due to the formation of complexes between β-cyclodextrin and dyes.     

Synthesis,spectral properties and dyeing on polyester of monoazo dyes from indol‐2‐one derivatives

Three series of phenylazo disperse dyes were prepared by coupling diazotised 4‐aniline dyes with 5‐indol‐2‐one dyes. The structures of these dyes were determined by proton nuclear magnetic resonance, Fourier Transform–infrared and elemental analysis. The effects of solvent on the ultraviolet–visible absorption spectra of these dyes were studied. The dyes displayed a λ_max shift of between 399 and 438 nm. The dyes were finally applied in the dyeing of polyester fibres in order to investigate their colour range and dyeing properties. Most of the dyes displayed high rubbing fastness and good washing and sublimation fastnesses on polyester fibres.     

Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes—Part 2: Application of some disperse dyes to polyester fibres

A series of yellow to greenish-blue aziridinyl azo dyes and their azo precursors containing a thienyl coupling moiety has been applied to conventional polyester fibre as well as microdenier polyester by high temperature exhaust dyeing. Heat transferability of these dyes onto polyester fibre has also been examined, using conventional heat-transfer printing techniques. The relevant dyeing characteristics, heat transferability, build-up, dyeability on microfibre polyester, washfastness and lightfastness are given. These aziridinyl dyes are reactive to polyester fibres under HT dyeing conditions. Fabrics dyed with aziridinyl dyes are more resistant to solvent extraction than those dyed with conventional dyes. Residual liquors showed only a pale colour when fabric dyed with aziridinyl dyes was dissolved and then precipitated, whereas a coloured polyester precipitate was obtained.     

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。     

Synthesis of 4,4′-aryldihydrazono-3-(3′-pyridyl)-2-pyrazolin-4,5-diones and 1-aryl-3-(3′-pyridyl)-4,4′-arylbisazo-5-aryliminopyrazoles and their application as disazo disperse dyes. Part II

3-(3′-Pyridyl)-2-pyrazoline-4,5-dione 4,4′(4,4′-biphenylenedihydrazone and p-phenylenedihydrazone) and its derivatives ( IIa-e, IIIa-e ) were obtained by the coupling reaction of tetrazotised benzidine and p-diamonobenzene with 3-(3′-pyridyl)-2-pyrazolin-5-ones ( Ia-e ). Similarly, bis-azo compounds containing pyrazole nucleous as, 1-aryl-3-(3′-pyridyl)-4,4′-arylbisazo-5-aryliminopyrazoles ( VIa-i and VIIa-i ) were prepared by the interaction of the corresponding chloro compound ( IV and V ) with aromatic amines. The compounds so obtained ( II, III, VI and VII ) are used as disazo disperse dyes for dyeing polyester fibres fast yellow-orange shades. Their fastness properties towards washing, rubbing, acid-alkaline perspiration and light were investigated.     

Disperse dyeing of polyester fibers: Kinetic and equilibrium study

The effect of temperature on the dyeing rate constant k, diffusion coefficient D, time of half‐dyeing t_1/2 was evaluated for the dyeing of polyester fibers with two disperse dyes, an azo and an anthraquinone dye. Activation energies of diffusion E were calculated. The polyester dyeing equilibrium was also studied and the partition coefficient K and standard affinity Δμ° at various temperatures were determined for the anthraquinone dye. Standard enthalpy ΔH° and standard entropy ΔS° of dyeing were also obtained. The same equilibrium parameters were not obtained for the azo dye because of its dyeing behavior. A similar kinetic and equilibrium study was made for the pure azo and anthraquinone compounds free from the dispersing agents present in the commercial dyes and the results are discussed. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 83: 2785–2790, 2002; DOI 10.1002/app.10254