Dyeing fine denier polypropylene fibers with phenylazo-<Emphasis Type="Italic">β</Emphasis>-naphthol-containing sulfonamide disperse dyes

A series of phenylazo-β-naphthol-containing sulfonamide disperse dyes were prepared from C.I. Acid Orange 7 by successive reactions of chlorination and amination, and their chemical structures were characterized by FTIR, ¹H NMR, and mass spectrometry. The dyes were applied to coloring of knitted fabrics from fine denier polypropylene fibers by exhaust dyeing and their optimal dyeing conditions, such as dyebath pH, dyeing temperature, dyeing time, and dye concentration were investigated in detail. Then, dye exhaustion, color strength, and color fastnesses of the dyes on the fibers were assessed and summarized. In view of dye exhaustion and color strength of the sulfonamide dyes on fine denier PP fabrics, 90°C was selected as the best dyeing temperature at dye concentration below or equal to 3.0% owf. For achieving higher color strength, 130°C was the better choice when the dye concentration was above 3.0% owf. The sulfonamide dyes, especially secondary sulfonamide dyes, exhibited superior dye exhaustion and color fastnesses to washing, sublimation, and rubbing on fine denier PP fabrics in comparison to C.I. Solvent Yellow 14 bearing the same chromophore but without sulfonamide group.     

Dyeing fine denier polypropylene fibers with phenylazo-β-naphthol-containing sulfonamide disperse dyes

A series of phenylazo-β-naphthol-containing sulfonamide disperse dyes were prepared from C.I. Acid Orange 7 by successive reactions of chlorination and amination, and their chemical structures were characterized by FTIR, ¹H NMR, and mass spectrometry. The dyes were applied to coloring of knitted fabrics from fine denier polypropylene fibers by exhaust dyeing and their optimal dyeing conditions, such as dyebath pH, dyeing temperature, dyeing time, and dye concentration were investigated in detail. Then, dye exhaustion, color strength, and color fastnesses of the dyes on the fibers were assessed and summarized. In view of dye exhaustion and color strength of the sulfonamide dyes on fine denier PP fabrics, 90°C was selected as the best dyeing temperature at dye concentration below or equal to 3.0% owf. For achieving higher color strength, 130°C was the better choice when the dye concentration was above 3.0% owf. The sulfonamide dyes, especially secondary sulfonamide dyes, exhibited superior dye exhaustion and color fastnesses to washing, sublimation, and rubbing on fine denier PP fabrics in comparison to C.I. Solvent Yellow 14 bearing the same chromophore but without sulfonamide group.     

Synthesis of acid dyes containing polyetheramine moieties and their low‐temperature dyeing properties on wool fiber

To realize the low‐temperature dyeing of wool fibers, the use of auxiliaries and wool modification are common methods. Low‐temperature auxiliaries may cause water‐pollution problems, and wool modification is a costly and uncontrollable process. In this study, new acid dyes, named D1–D3, containing polyetheramine groups were synthesized and applied to wool fiber by conventional and low‐temperature exhaust dyeing procedures. The results indicate that the new acid dyes could interact with wool‐fiber‐like auxiliaries and render a high exhaustion rate to the wool fiber at a dyeing temperature of 80 °C. In comparison with Acid Blue 25, the D1–D3 dyes showed an increased dyeing rate, especially under a dyeing temperature of 80 °C. Despite the bigger relative molecular masses of D1–D3, the exhaustion rates of D1–D3 were still higher, and the times of half‐dyeing were shorter than that of Acid Blue 25. The color differences between the wool fabrics dyed with the four dyes at 80 and 98 °C, respectively, were compared. We found that the color differences of D1–D3 between 80 and 98 °C were smaller than that of Acid Blue 25. The interactions between the dyes and wool fiber were analyzed and manifested by the measurement of the ζ potential of the dyes and wool fiber. The leveling and transfer properties of the D1–D3 dyes were also investigated, and the color differences of the wool fabrics dyed with Acid Blue 25, D1, and D2 were very low at all measured pH values and temperatures. The fastnesses of D1–D3 on wool fabric were almost the same as that of Acid Blue 25. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 45793.     

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.     

Comparison of disperse dye exhaustion,color yield,and colorfastness between polylactide and poly(ethylene terephthalate)

Ten popular disperse dyes with different energy levels and chemical constitutions were used to compare their exhaustion, color yield, and colorfastness on polylactide (PLA) and poly(ethylene terephthalate) (PET). Only two out of the 10 dyes had exhaustions higher than 80% on PLA at 2% owf. Five out of the 10 dyes had exhaustions less than 50%. All 10 dyes had more than 90% exhaustion on PET, whereas six of them had exhaustions of 98% or higher. There was no obvious pattern as for which energy level or which structure class provided dye exhaustion better than that of others. Although PLA had lower disperse dye exhaustion than that of PET, it had higher color yield. Based on the 10 dyes examined, the color yield of PLA was about 30% higher than that of PET. This means that even with low dye uptake, PLA could have a similar apparent shade depth as that of PET if the same dyeing conditions are applied. Our study supported that the lower reflectance, or reflectivity, of PLA contributes to the higher color yield of PLA than that of PET. A quantitative relation between the shade depth of PLA and PET based on their dye sorption was developed. Disperse dyes examined had lower washing and crocking fastness on PLA than on PET. The differences in class were about 0.5 to 1.0. If the comparison was based on the same dye uptake, the differences might be larger. The differences in light fastness between the two fibers were smaller than that in washing and crocking fastnesses. The light fastness of disperse dyes on PLA is expected to be even better if the comparison is based on the same dye uptake on both fibers. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 3285–3290, 2003     

Effect of Sandospace R on the dyeability of gamma-irradiated wool,wool/polyester and polyester fabrics with some disperse dyes containing amino groups

The effect of Sandospace R on the dyeability of gamma-irradiated wool, wool/polyester and polyester fabrics towards disperse dyes has been investigated. The effects of the different factors that may affect the colour yield of the dyed samples (such as radiation dose, Sandospace R concentration, pH strength of the dye bath, dye concentration, dyeing temperature and time were studied. In general, and regardless of the studied factor, the irradiated fabric showed a significant dye affinity for the disperse dyes employed compared/to the unirradiated fabrics. However, the different fabrics irradiated to a dose of 2Mrad showed the highest colour strength with a high level of dyeing. Also, it was observed that a concentration of Sandospace R as low as 0·5% effectively enhances the dye affinity for the disperse dyes used here. Moreover, it was found that the pH of the dyeing bath at which the highest colour strength obtained was 3. Increasing the dye concentration up to 4% based on fabric weight, caused a significant enhancement in the colour strength, whilst raising/the dyeing bath temperature from 60°C to 100°C appreciably accelerated the rate of dye uptake. Complete exhaustion absorption of the disperse dye occurred over a period of 2h. © 1998 Society of Chemical Industry     

Microwave‐assisted dyeing of poly(butylene terephthalate) fabrics with disperse dyes

In this study, conventional heating and microwave dielectric heating in the exhaust dyeing of poly(butylene terephtalate) fabrics with disperse dyes were studied in order to determine whether microwave heating could be used to increase the dyeability of poly(butylene terephtalate) fibre in shorter processing times and enable dyeings of adequate wet fastness to be obtained. Accordingly, the samples of 100% poly(butylene terephtalate) single jersey knitted fabric were dyed with CI Disperse Yellow 160 and CI Disperse Yellow 42, CI Disperse Red 177 and CI Disperse Red 91, CI Disperse Blue 79:1 and CI Disperse Blue 54 at 98 °C with or without microwave dielectric heating. The colouristic properties, colour fastnesses and the tensile properties of the dyed fabrics were investigated and compared with each other. Microwave dielectric heating is regarded as a tool for ‘green chemistry’ and provides many advantages over conventional heating without any deterioration in the properties of the dyed materials. Microwave heat dyeing enhances the exhaustion and the fixation of dye, and good colour fastnesses and repeatability in dyeings are achieved in short heating times of the dyebath.     

Telechelic PEG-polymers end-capped with chromophores: Using as cationic reactive dyes and salt-free dyeing properties on cotton fabrics

In this article, telechelic polymers containing polyethylene glycol (PEG) moieties as space groups were combined with chromophores to synthesize cationic reactive dyes (BCD-R, BCD-Y, and BCD-B). The salt-free dyeing performance of these telechelic polymeric cationic reactive dyes on cotton fabrics was evaluated. The exhaustion and fixation of the dyes in salt-free dyeing was above 89.33 and 77.22%, respectively. The color fastness of dry rubbing for the three dyes reached grade 4–5, and their color fastness to light reached grade 5–6. Their washing fastness also reached grade 4–5, except for that of BCD-Y (grade 3–4). The results showed that the dyes possessed good leveling and build-up properties and substantivity to cellulose fiber. The zeta potential (ξ-potential) of dyed fabric was estimated, and it was found that the ξ-potential of the fabrics increased after dying with telechelic polymeric cationic reactive dyes, and the more dye that was used, the greater ξ-potential increase. The exhaustion curves of dyes were also determined, and they were much different from those of anionic reactive dyes. The adsorption kinetics and isotherms of BCD-R were investigated. It was found that the pseudo-second-order kinetic model gave the best fit of the experimental data at all three tested dyeing temperatures (25, 45, and 65°C) with R² values over 0.998. Both the Langmuir and Freundlich models could be used to describe the adsorption of BCD-R onto cellulose fibers and the Langmuir model fit the experimental data better than the Freundlich model. The thermodynamic parameters (ΔG, ΔS, ΔH, and activation energy) of the dye adsorption process were researched further. The results indicated that the adsorption of BCD-R onto cotton fibers was spontaneous and exothermic and that after adsorption onto the cotton fibers, the degree of freedom of the dye decreased.     

Redox-initiated graft copolymerization onto wool with thiourea as reductant. IV. Grafting of vinyl sulfone dyes onto wool using thiourea–H2O2 redox system

Wool samples were dyed with a vinyl sulfone dye in the presence of thiourea and H₂O₂ under a variety of conditions. Increasing the H₂O₂ concentration from 2.5 mmole/l. to 20 mmole/l. caused a significant enhancement in the rate of the dyeing, whereas increasing the thiourea concentration from 1.25 mmole/l. to 10 mmole/l. brought about an increase in the rate of dyeing. Further increase in the thiourea concentration (i.e., up to 15 mmole/l.) caused a significant decrease in the rate of dyeing. Raising the dyeing bath temperature from 30°C to 70°C accelerated appreciably the rate of dye uptake. With respect to dye concentration, complete exhaustion occurred at dye concentrations of 0.5% and 1% (owf) when dyeing was performed at 70°C and pH 6 over a duration of 2 hr. This contrasts with 90% and 55% exhaustion for dye concentrations of 3% and 5% (owf), respectively. The rate of dyeing obtained at different pH's follows the order pH 2 < pH 4 < pH 6 < pH 8. A dye fixation of approximately 68%, 64%, and 50% could be achieved at pH 4, 6, and 8, respectively, if dyeing was performed at 70°C for 2 hr in a bath containing a dye concentration of 3% (owf) in the presence of thiourea (10 mmole/l.) and H₂O₂ (15 mmole/l.). The mechanism of dyeing is believed to be grafting by vinyl addition to wool radical formed under the influence of the decomposition products of thiourea and H₂O₂. Evidence of this mechanism is presented.     

Dyeing behaviors of ionic liquid treated wool

In this article, a new class of “green” solvent—ionic liquid (IL) was employed to improve the dyeability of wool. The physical and chemical properties of the IL‐treated wool, such as surface morphology, wettability, and tensile strength were first analyzed, and then the dyeing properties of IL‐treated wool were investigated in terms of dyeing rate, dyeing exhaustion at equilibrium, color depth, and color fastnesses. The scanning electron microscope (SEM) images showed eroded marks on IL‐treated wool fiber surfaces. The water contact angle of the fabric treated with IL at 100°C decreased from 118.6° to 106.4°. The tensile strength of IL‐treated wool fibers was slightly decreased when the treating temperature was less than 100°C. Dyeing kinetics experiments revealed that the IL treatments greatly increased initial dyeing rate, shortened half‐dyeing time, and time to reach dyeing equilibrium. The final exhaustion and color depth of IL‐treated wool were also increased accompanying with slightly decreased color fastness. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

聚乳酸纤维的常压染色研究

在常压下,用七种分散染料及其复配染料对聚乳酸纤维进行染色,并对染色纤维进行了牢度性能测试。除了黄棕色外,其余染料的上染率都随着色度的增加而下降。同一只染料在同一的色度下,延长染色时间对增加染料的上染率作用不明显。随着染色温度的升高,黄素色和蓝色染料的上染率得到明显的提高,而对深红色和黄棕色染料而言这种作用并不明显。同时,通过测量染色纤维的色彩强度定量的描述了染料上染率对温度的敏感性。     

竹/棉混纺织物活性染料染色使用代用碱固色的工艺探讨

通过代用碱TF-221和常规纯碱对活性染料浸染固色的对比实验,测定了碱剂在染色浴固着反应中pH值的动态变化值。通过染色K/S值、各项色牢度、上染速率的对比实验,讨论了代用碱TF-221在活性染料染色中代替纯碱作为固色剂的作用效果,并测定两种工艺染色后织物的强力变化,找到合适的固色工艺。实践证明:代用碱TF-221完全可以代替纯碱用于活性染料染色对竹/棉混纺织物染色时的固色,其固着浴pH值稳定范围符合活性染料的染色特征,可以获得与使用纯碱相当或高于的K/S值和染色牢度,且上色缓慢,起到匀染作用;染色后织物的强力无明显下降。     

Pigment dyeing of polyamide‐epichlorohydrin cationized cotton fabrics

A synthesized cationic reagent named polyamide‐epichlorohydrin (PAE) was used to cationize cotton fabrics which were dyed with nanoscale pigments after PAE modification. The results showed that when the PAE concentration was below 7% (owf), the K/S value increased nearly linearly with increasing of PAE concentration, and excess that concentration the K/S value did not increase further. With increasing the pH value of cationization bath, the K/S value increased first and then decreased, the maximum K/S value appeared at pH 9–10. Cotton fabrics cationized at 80°C for 20 min exhibited the best cationizing result. Both the pigment uptake and the color strength reached their own maximum values when the dye bath was neutral. When the pigment concentration was 1% (owf) the addition of 1g/L sodium chloride in the dye bath could decrease the pigment uptake while for 5% (owf) pigment concentration the uptake increased with increasing the amount of sodium chloride. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Salt-free reactive dyeing of betaine-modified cationic cotton fabrics with enhanced dye fixation

Novel cationic cotton fabrics were prepared by an efficient and simple one-step pad–dry–bake pretreatment process with betaine as cationic reagent. Ester bonds formed between cotton fibers and betaine hydrochloride were proved by Fourier transformed infrared attenuated total reflection(FTIR-ATR) spectra. Moreover, the properties of the cationic fabrics, including X-ray Diffraction(XRD), tensile strength and whiteness and yellowness index,were investigated in comparison with that of the untreated ones. The cationic fabrics were applied in salt-free dyeing of C.I. Reactive Red 195, C.I. Reactive Yellow 145 and C.I. Reactive Blue 19. Different dye fixation processes were applied and compared for untreated and cationic cotton. Dye fixation and color fastness properties of the dyes were tested, and the results presented that dye fixation on the cationic fabrics in the absence of salt was improved with satisfactory light fastness property and applicable wash and rub fastnesses.     

One‐bath union dyeing of wool/polytrimethylene terephthalate blends†

The one‐bath dyeing of blends of polytrimethylene terephthalate (PTT) staple and wool has been investigated. The exhaustion of selected Terasil disperse dyes on PTT fibre and Lanasol reactive dyes on wool was measured as a function of temperature, together with the cross‐staining of the Terasil dyes on the wool component and the Lanasol dyes on PTT component. Most Terasil disperse dyes achieved satisfactory dye uptake on PTT at 110 °C, whereas on conventional polyester (polyethylene terephthalate) temperatures of up to 130 °C are required. An optimised union‐dyeing technique for wool/PTT blends was developed which minimised the staining of Terasil disperse dyes on wool and produced dyed goods with high levels of wet colour fastness. Carriers were not required to enhance the dyeability of PTT at low temperatures. The wool component appeared to be protected against damage at 110 °C by the reactive dyes. The results indicate the potential for blending PTT fibre and wool to produce fabrics that are easier to dye at lower temperatures than conventional wool/polyester blends.     

Dyeing of glass fiber fabrics having amino groups with acid dyestuff and after-chroming

The glass fiber fabrics treated with a coupling agent that contains aminoethyl groups are used as a dye with a procedure similar to that for nylon with acid dyestuff and after-chroming. Furthermore, we investigated the dyeing parameters and physical properties. Results revealed that the glass fiber fabrics treated with the coupling agent were dyeable. The best conditions for acid dyestuff are at pH = 6 and at 5% owf (on the weight of fiber) concentration of dyestuff; for after-chroming, they are at 1.4% owf concentration of potassium dichromate and at 70°C for 50 min. In addition, the fabrics dyed have much better colorfastness (4–5 grade), and the average dyeing evenness is lower than 1.5. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 66: 1039–1048, 1997     

蓝色活性染料的合成及拼混增效

本文设计合成了22只含复合双活性基的蓝色活性染料。测定了活性染料的四个特征参数S、E、R和F值,考察了染料结构与直接性的关系。测定了染料的提升力,根据染料的相容性和染料的结构特征选择拼混染料;不同类活性染料的拼混和同类活性染料的拼混都得到染深性很好的混合染料。测定了活性染料的耐碱性,耐碱性好的染料与耐碱性差的染料通过适当比例混合后,混合染料具有优异的耐碱性。     

Dyeing of woven polyester fabric with curcumin: effect of dye concentrations and surface pre‐activation using air atmospheric plasma and ultraviolet excimer treatment

Dyeing of polyester fabric with curcumin was studied at 90 and 130 °C without and with a prior surface activation of polyester fabric using two different ecotechnologies: air atmospheric plasma treatment and ultraviolet excimer lamp at 172 nm. Without surface activation, dyeing with curcumin followed classical disperse dye behaviour, with higher dye uptake at 130 °C than at 90 °C, and saturation was readily reached at 2% dye owf at 130 °C with a colour yield of 22. Surface‐sorbed curcumin molecules extracted with ethanol seemed to increase the colour yield values at 90 °C dyeing, while at 130 °C they decreased the colour yield values. When dyeing was carried out after a prior surface activation of the polyester fabrics, increased colour yield was observed at both dyeing temperatures for the ultraviolet excimer lamp only (with colour yield increasing from 2 to 10 at 90 °C and from 22 to 28 at 130 °C for a 2% dye owf). Indeed, both surface activation methods yielded hydrophilic species at the polyester fabric fibre surface, which were confirmed by water contact angle, X‐ray photoelectron spectroscopy measurements and atomic force microscopy. However, the surface of the polyester fabric activated using plasma lost all of its hydrophilic species, reaching the water contact angle of untreated polyester when subjected to the dyeing conditions. The excimer treatment yields hydrophilic species that are more resistant to high temperature and pressure dyeing.     

混纺交织制品染色存在的问题与染料商品开发

将纤维按染色性能分成ABCD四类，A类纤维是指能用酸性染料染成坚牢的深浓色的纤维，B类纤维是指能用阳离子染料染成坚牢的深浓色的纤维，C类纤维是指纤维素纤维用染料染成坚牢的深浓色的纤维，D类纤维是指能用分散染料染成坚牢的深浓色的纤维。综述了同类不同种纤维或不同类纤维混纺交织制品染色存在了问题，以及用于混纺交织制品染色用染料的开发情况。     

Dye distribution in the dyeing of mixed denier polyester fabrics

Microfibre polyester is sometimes blended with higher denier fibres to achieve good aesthetic effects at lower cost. Two polyester yarns of 1.4 and 0.7 denier were dyed singly and together with a range of depths of CI Disperse Blue 79, and the dye distribution over the course of the dyeings was examined. The uptake is initially greater on the microfibre, but as dyeing is continued the distribution becomes more even, and eventually the same concentration of dye is present on both fibres. Based on the common observation that a given concentration of dye produces a lighter shade on a microfibre, the redistribution of dye during the process causes a continuing shade change even though the bath exhaustion is constant. A mixture of three dyes produced a stable hue on a fabric of 1.0 denier polyester after 20 min at a fixed dyeing temperature, but when dyed on a fabric of 1.0 and 0.5 denier yarns, a change in hue continued for more than 60 min.