Physicochemical aspects of the liposome-wool interaction in wool dyeing

Despite the promising application of liposomes in wool dyeing, little is known about the mechanism of liposome interactions with the wool fiber and dyestuffs. The kinetics of wool dyeing by two dyes, Acid Green 27 (hydrophobic) and Acid Green 25 (hydrophilic), were compared in three experimental protocols: (1) without liposomes, (2) in the presence of phosphatidylcholine (PC) liposomes, and (3) with wool previously treated with PC liposomes. Physicochemical interactions of liposomes with wool fibers were studied under experimental dyeing conditions with particular interest in the liposome affinity to the fiber surface and changes in the lipid composition of the wool fibers. The results obtained indicate that the presence of liposomes favors the retention of these two dyes in the dyeing bath, this effect being more pronounced in case of the hydrophobic dye. Furthermore, the liposome treatment is accompanied by substantial absorption of PC by wool fibers with simultaneous partial solubilization of their polar lipids (more evident at higher temperatures). This may result in structural modification of the cell membrane complex of wool fibers, which could account for a high level of the dye exhaustion observed at the end of the liposome dyeing process.     

Synthesis and application of disazo reactive dyes derived from sulfatoethylsulfone pyrazolo[1,5-a]pyrimidine derivatives

Two models of heterocyclic reactive dyes based on disazo pyrazoloprymidine derivatives and possessing a sulfatoethylsulfone reactive group were synthesized and characterized by elemental analysis, IR and ¹H NMR spectroscopy. The dyes were applied to cotton, wool and silk fabrics. Effects of varying dyeing conditions were investigated. The results assessed for the exhaust dyeing methods on the different fabrics indicate that these reactive dyes showed high exhaustion and fixation values. The dyed fabrics also showed very good light fastness and good to excellent washing, rubbing and perspiration fastness.     

Eco-dyeing and functional finishing of wool fabric based on Portulaca oleracea L. as colorant and Musa basjoo as natural mordant

Biomass energy is the most acknowledged renewable resource due to its universality, richness, and renewability. This study utilized a Portulaca oleracea L. plant as a natural colorant for wool fabric dyeing with a high color yield at optimum extraction and dyeing conditions. To evaluate the dyeing mechanism and feasibility of the extracted dyes, we analyzed and characterized the molecular structure and nano-level particle size. The dyeing kinetics and the morphology of dyed fabrics were integratedly explored; the adsorption process of wool fabric on natural colorant molecules was increasingly in line with the pseudo-second-order kinetic adsorption model. Further, the dyeing effects of wool fabrics were compared to that of Musa basjoo mordant and synthetic dyes to confirm the superior color depth (K/S value 23.53), biological function as anti-ultraviolet (UPF value 253.47), and anti-bacterial activity (antibacterial rate of Staphylococcus aureus/Escherichia coli was 71.3%/37%). Our findings provide a feasible scheme for providing deep color and biological activity to wool fabrics. This has broad application prospects in the field of eco-friendly textile materials.     

Synthesis,Properties, and Application of Cationic Reactive Disperse Dyes Containing Quaternary Group

A series of cationic reactive disperse dyes containing quaternary group were synthesized. The dyeing behavior of these dyes on wool was studied. The results show that cationic reactive disperse dyes containing quaternary group is available to form covalent bond with nucleophiles in the wool even under acidic condition. The fastness on wool was excellent.     

Extracting natural dyes from wool--an evaluation of extraction methods

The efficiency of eight different procedures used for the extraction of natural dyes was evaluated using contemporary wool samples dyed with cochineal, madder, woad, weld, brazilwood and logwood. Comparison was made based on the LC-DAD peak areas of the natural dye's main components which had been extracted from the wool samples. Among the tested methods, an extraction procedure with Na(2)EDTA in water/DMF (1:1, v/v) proved to be the most suitable for the extraction of the studied dyes, which presented a wide range of chemical structures. The identification of the natural dyes used in the making of an eighteenth century Arraiolos carpet was possible using the Na(2)EDTA/DMF extraction of the wool embroidery samples and an LC-DAD-MS methodology. The effectiveness of the Na(2)EDTA/DMF extraction method was particularly observed in the extraction of weld dye components. Nine flavone derivatives previously identified in weld extracts could be identified in a single historical sample, confirming the use of this natural dye in the making of Arraiolos carpets. Indigo and brazilwood were also identified in the samples, and despite the fact that these natural dyes were referred in the historical recipes of Arraiolos dyeing, it is the first time that the use of brazilwood is confirmed. Mordant analysis by ICP-MS identified the widespread use of alum in the dyeing process, but in some samples with darker hues, high amounts of iron were found instead.     

Synthesis,characterization and dyeing assessment of novel acid azo dyes and mordent acid azo dyes based on 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid on wool and silk fabrics

Novel acid mono azo and mordent acid mono azo dyes were synthesized by the coupling of diazonium salt solution of different aromatic amines with 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid. The resulting dyes were characterized by spectral techniques like elemental analysis, IR, ¹H-NMR and UV visible spectroscopy. The dyeing performance of all the dyes was evaluated on wool and silk fabrics. The dyeing of chrome pre-treated wool and silk fabrics showed better hues on mordented fabrics. Dyeing of wool and silk fabrics resulted in pinkish blue to red shades with very good depth and levelness. The dyed fabrics showed excellent to very good light, washing, perspiration, sublimation and rubbing fastness.     

The evaluation of structural changes in wool fibre keratin treated with azo dyes by Fourier Transform Infrared Spectroscopy

Fourier Transform Infrared Spectroscopy spectroscopy is a useful technique for the analysis of structural changes in wool fibres at the molecular and supermolecular levels. Ecological requirements the textile industry has to meet oblige manufacturers to use ecological dyes in the process of fibre dyeing. These dyes should not split into the forbidden, carcinogenic aromatic amines (e.g. benzidine) while used. Wool was dyed with an azo dye, then underwent a chemical reaction. Changes were observed in the region of Amide A, Amide B, Amide I and II, dipolar ions amino acids, and the fingerprint region.     

A study on multifunctional protein fibre with UV protection,moth repellency and antibacterial properties using ESIPT core containing benzimidazole and benzothiazole based functional acid azo dyes

Water soluble fluorescent acid azo dyes with benzimidazole and benzothiazole component having excited state intramolecular proton transfer (ESIPT) core were synthesised by diazo coupling. The structure of the dyes were analysed and confirmed by Fourier Transform Infrared – spectroscopy (FT-IR), elemental analysis, ¹H NMR and ¹³C NMR analysis. Absorption and emission characteristics of the dyes were studied in different polarity solvents shown bathochromic (red) shift as solvent polarity increases. Wool and silk fabric dyed with synthesised dyes displayed high exhaustion, uniform dyeing and good wet fastness properties. The dyed substrate showed green and purple fluorescence under UV light (366 ​nm) along with UV protection. Dyed wool fabric was also assessed for antibacterial activity by calculation of bacterial reduction Staphylococcus Auerus (Gram positive), Klebsiella Pneumonia (Gram negative) bacteria. The dyed wool were also examined for the resistivity against insect pests Anthrenus Flavipies (Le Conte) by calculation of the fabric weight loss, Mortality of moth and visible assessment of fabric attacked by moth after 14 days in given conditions. Consequently, it was demonstrated that wool fabric dyed with Benzimidazole and benzothiazole based acid dyes had various functionalities, such as UV protection, antibacterial activity and mild moth repellency.     

Theoretical investigation of azo dyes adsorbed on cellulose fibers: 2. Spectroscopic study

Electronic absorption spectra and the frontier orbitals of 1-arylazo-2-naphtol dyes are computed and analyzed in four models, namely in the gas phase (model I), in a solvent (model I + CPCM), adsorbed on the cellulose surface (model II), and model II in the presence of solvent (model II + CPCM) via time-dependent density functional theory (TD-DFT) and conductor-like polarizable continuum model (CPCM) at the B3LYP/6-31G** level of theory. A bathochromic shift is observed for the λ_max peak due to both short-range and long-range interactions of the non-ionic dyes with cellulose, while the ionic dyes exhibit hypsochromic shift in their λ_max peak. The results predict that the studied dyes should be nearly yellow after being adsorbed on cellulose with excellent color strength. Furthermore, the ionic dyes are suitable for the dyeing of cellulose fibers. The nuclear magnetic resonance (NMR) chemical shieldings calculated for the azo dyes in the gas phase and adsorbed states and for their tautomeric equilibrium mixtures show that the NMR technique can be used successfully to follow the dyeing process.     

Synthesis and spectral characterization of azo dyes derived from calix[4]arene and their application in dyeing of fibers

In this study, the synthesis and characterization of two new upper rim functionalized azocalix[4]arene dyes have been obtained by coupling calix[4]arene with different diazo compounds of 3,5-dicarboxyaniline and 4-aminobenzene sulphon amide. The characterization of these dyes has been carried out by elemental analysis, FT-IR and ¹H NMR spectra. The effect of varying dielectric constants of solvents on the absorption spectra of azocalix[4]arenes (1, 2, 3, 4) and commercial Isolan Gelb SGL (T) have been examined by UV–Vis spectrophotometer. These azocalix[4]arene dyes have also been used for dyeing textile fibers like cotton, wool, acetate, polyester and polyamide fibers. Their dyeing and fastness properties have also been discussed.     

Synthesis,characterization, and dyeing performance of some azo thienopyridine and thienopyrimidine dyes based on wool and nylon

A string of novel heterocyclic mono azo dyes were synthesized and their utilization in dyeing different fabrics as wool and nylon were discussed. Thienopyridine azo dyes 4 and 6 were prepared by reaction of chloro acetamidederivative 2 with diamino compounds to yield 3 and 5 , followed by reaction with NaNO₂/HCl and coupling with nucleophilic reagent. One-pot reaction of chloro acetamide 2 with ammonium thiocyanat in solvent ethanol gave the unexpected thienopyrimidine derivative 7 , which contain two active sites, the former is primary amine that was able to form diazonium salt that coupled with N,N-dimethylaniline, resorcinol, and/or self-coupling to afford the azo dyes 8-10 , and the latter is active methylene group that underwent coupling with different diazonium salts to give the azo thienopyrimidine derivative dye 11-15 . The dyeing performance of these azo dyes had been investigated in terms of their dyeing behavior and fastness properties on different fabrics. Results showed that the color strength (K/S) values, as well as, washing, rubbing, and resistance to acid, alkali and light showed high efficiency of these heterocyclic mono azo dyes to dye wool rather than nylon fibers.     

Synthesis and characterization of reactive dyes based on 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid

A series of new quinazolinone based mono azo reactive dyes (D_1–10) have been prepared by subsequent diazotization of 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid (C) and coupling with various 4-chloro anilino cyanurated coupling components. These dyes give purple, red, orange and yellow color shades. All the reactive dyes were characterized by their percentage yield, UV–Vis spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy and dyeing performance on silk, wool and cotton fibres. The percentage dye bath exhaustion on different fibres has been found to be reasonably good and acceptable. The dyed fibres show moderate to very good light fastness and good to excellent washing and rubbing fastness.     

Changes in the Structure of Wool Fiber in Dyeing in a Redox Medium

The suitability of redox systems for wool dyeing with acid and active dyes at temperatures below the boiling point of the dyeing solutions was studied. The influence of the hydrogen peroxide-reductant (glucose, ethylene glycol, 1,2,3-propanetriol, polyoxymethylene, and hexamethylenetetramine) systems on the surface of wool roving was elucidated.__________Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 4, 2005, pp. 616-618.Original Russian Text Copyright © 2005 by Petrova, Grebennikov, Burinskaya.     

Application of liposomes in the textile industry

The results of the research of the role of liposomes in bleaching, dyeing, and finishing of wool and cotton, as well as sorption of dyes are discussed.     

Application of newly synthesized bisazo dichloro-s-triazinyl reactive dyes bearing 1,3,4-oxadiazole molecule

Novel bisazo dichloro-s-triazinyl (DCT) reactive dyes (5a–h) containing 1,3,4-oxadiazole molecule as a tetrazo component were synthesized and applied on silk, wool and cotton fibers by exhaust dyeing method. The structures of these dyes were confirmed by UV–vis, FT-IR, ¹H and ¹³C NMR and elemental analyses. The exhaustion, fixation and fastness properties of the dyed fabric were assessed and the results demonstrated that these dyes showed moderate to very good light and good to excellent washing and rubbing fastness properties. The colorimetric data (L¹, a¹, b¹, C¹, H¹, K/S) of these dyes have also been studied in detail.     

3-Hydroxy-1,2,4-benzotriazin-1-oxid-7-carbonsäure und verwandte Verbindungen

The chloride of 3-chloro-1,2,4-benzotriazine-1-oxide-7-carboxylic acid has been prepared, and from this a number of derivatives of 3-hydroxy-1,2,4-benzotriazine-1-oxide-7-carboxylic acid were synthesized by stepwise substitution of the two halogen atoms. This acid chloride has further been used for linking dye components containing amino groups, and for the synthesis of reactive dyes whose suitability for dyeing cellulose and wool has been examined.     

Environmental hazard in textile dyeing wastewater from local textile industry

Colorants and chemicals used in the textile coloration process are required to meet the fashion demands; however these introduced serious environmental hazards that are mainly resulted in effluent loading, containing the toxic, carcinogenic, and mutagenic substances, to natural environment. Textile dyeing process and the rinsing of dyed fabric utilize a variety of substances including dyes/ pigment, fixing agent, surfactants, leveling agent, mordant, salts etc. However, all these substances are not fully consumed in the process, and a residual content remains in the dyeing effluent. This review observes the challenges to environment posed by the dyes and chemicals present in spent dye bath, progress in possible remedies in dyeing wastewater treatment including the nanotechnology; and particularly discusses the studies based on the dyeing effluent samples collected from the local textile processing industries. There are obvious case studies made in different regions, using the process wastewater from the local textile dyeing and processing industries, confirming the need for research and innovation to replace or control the hazardous dyes and chemicals in conventional dyeing process and making the resulting effluent more environment- friendly. Moreover, the cleaner production practices and environmental standards are introduced in improving the textile dyeing process. Selection of dyes and chemicals, use of best available techniques, and wastewater treatment technologies can significantly improve the textile dyeing to become an environment- friendly process.

     

Micro Analysis on Hallstatt Textiles: Colour and Condition

Due to the special conditions in the Bronze Age and Hallstatt Period salt-mines of Hallstatt, Austria, a large number of archaeological textile fragments, dated from 1400 to 400 BC, can be found. Textiles of good condition from these periods are quite unique. The fibres are identified as wool and most of the fragments still have colours i.e. yellow, green, olive-green, brown, blue and black. To obtain information about the dyeing techniques used in this period, dyestuffs analyses are performed by high performance liquid chromatography coupled to photo diode array detection (HPLC-PDA) and mordant analysis by scanning electron microscopy with energy dispersive X-ray spectroscopy (SEM/EDS). In addition, the condition of the textile fibres is assessed by SEM. The analyses revealed that all textiles were dyed with plant dyes and insect dyes. The yellow plant dyes and the red insect dyes are mordant dyes but the identification of mordants turned out to be difficult. SEM/EDS analyses of small uncontaminated areas on the fibre showed that the elements aluminium, iron and copper are present in many samples. These elements could originate from a mordant or from the mine. The condition of the fibres was assessed by the presence of the characteristic scales on the wool, tears, cuts and particles from the mine. It was found that a relation exists between the copper content of the fibres and their condition. Degraded fibres contain more copper. Black textile fragments which are most possibly coloured by iron gall-black show as well degradation phenomena.     

Eco-dyeing using Tamarindus indica L. seed coat tannin as a natural mordant for textiles with antibacterial activity

Tamarind seed coat tannin was extracted and its tannin class was determined. The extracted tannin was employed as a natural mordant alone and in combination with metal mordant namely copper sulphate for cotton, wool and silk fabrics and dyed using natural dyes namely turmeric and pomegranate rind. The colour strength, colour coordinates, wash and light fastness were evaluated and compared for all the three fabrics with and without mordanting. The pre-mordanted fabrics on dyeing gave better colour strength, wash and light fastness than those dyeing obtained without mordanting. The total phenolic content of the extract was calculated and minimum inhibition concentration was 1% against both the Staphylococcus aureus and Escherichia coli bacteria. The mordanted and dyed fabrics resulted in good antibacterial activity up to 20 washes, when natural mordant was used along with 0.5% and 1% copper sulphate mordant and dyed with natural dyes.     

2-氨基-10-羟基-5,10-二氢磷杂吖嗪-10-氧化物的合成、诱变性及应用

2-氨基-10-羟基-5;10-二氢磷杂吖嗪-10-氧化物的合成、诱变性及应用;二氢磷杂吖嗪; 吡唑啉酮; 合成; 结构鉴定; 诱变性