Synthesis of an electron-rich aniline-containing dye and its dyeing behaviors on silk through a three-component Mannich-type reaction

Under the guidance of the finding that the tyrosine residues in proteins could undergo three-component Mannich-type reactions with formaldehyde and electron-rich aniline-containing compounds,which forms covalent bonding connections between the protein of interest and the aniline with high levels of selectivity under relatively mild conditions,an orange aromatic primary amine-containing acid dye AMODB was designed and readily synthesized.The molecular structure was characterized by FTIR,~1H NMR,mass spectrometry and elemental analysis.The synthesized dye and a similar control dye(C.I.Acid Yellow 11) without primary amine groups were applied to dye silk fabric by three dyeing processes:Mannich-type dyeing(with and without the addition of formaldehyde) and acidic dyeing.Their washing and rubbing fastness properties with different dyeing methods were examined and compared.It was found that the dyed silk fabric with AMODB by the Mannich-type dyeing showed higher color depth,better anti-stripping ability to DMF and better washing fastness than those of the dyed silk fabric with C.I.Acid Yellow 11 by acidic dyeing due to the covalent bond formation between the dye chromophore of AMODB and silk fiber.In addition,mild Mannich dyeing conditions suitable for silk(AMODB at 3%owf,75:1 liquor-to-goods ratio,dyebath pH 5.5,30℃,10 h) were provided.     

Properties of a novel acid dye 1-amino-4-[(6-nitro-2-benzothiazolyl)amino]-9,10-anthraquinone-2-sulfonic acid with anti-UV capability

<正>A novel acid dye acid was synthesized by the condensation reaction between bromamine acid and 2-amino-6-nitrobenzothiazole and its anti-UV protection properties were evaluated.The results showed that silk dyed with this dye had very good ultraviolet radiation protection capability and excellent dyeing performance.The UV-absorption mechanism of this dye was also discussed.     

Ultrasonic assisted improved extraction and dyeing of mordanted silk fabric using neem bark as source of natural colourant

Natural products with therapeutic nature are nowadays warmly welcomed in textiles. Current study is concerned with isolation of tannin from neem bark (Azadirachta indica) and its application onto silk fabric. For improvement in shades, chemical & bio-mordants have been employed at optimal dyeing conditions. It is found that methanolic extract of pH 5 obtained 8 g dye powder after US Treatment for 30 min has given high color strength if used to dye irradiated silk for 65 min at 75 °C. Bio-mordanting using herbal plants has improved the color characteristics as compared to chemical mordants used. ISO standards for color fastness reveal that herbal based bio-mordants have improved the rating from good to excellent as compared to chemical mordants used. It is concluded that US treatment has not only isolate the colorant for neem bark under mild condition but also given excellent characteristic using bio mordants onto silk fabrics.     

Silk fabric dyed with extract of sophora flower bud

This study analysed the use of sophora flower bud extract for dyeing and the resulting colour character and fastness of dyed silk fabric. The pigment composition on the silk fabric and recycling of this extract were also studied. The results indicated that the dyed silk fabric possessed good washing, rubbing and perspiration fastness, and the pigment composition on the silk fabric was mainly rutin and quercetin. The average recovery rate of the dye was 55.00%. These results demonstrate that the sophora flower bud extract is an effective natural dye.     

Development of a novel method for investigation the uptake behaviors of acid dye on silk fabric at various flow statuses in a coloration circular pipe

A novel methodology and a special fluid dynamics coloration machine were successfully constructed, and then the uptake behaviors of an acid dye on silk fabric under different flow statuses and parameters were explored for the first time. The obtained results show that the traditional additions of auxiliaries will not significantly change the kinematic viscosity of the dyeing bath. As coloration flow status was in laminar, transitional and turbulent flow, respectively, the dye uptake behaviors on the silk fabric were significantly different. Meanwhile, decreasing the bath pH value and increasing the temperature of the dyeing bath had a significant positive effect on the dye uptake behaviors in different flow statuses. Additionally, coloration in laminar or transitional flow preferred a relatively low dosage of neutral salt, which benefits to a cleaner production. Additionally, high coloration performance with color-fastness to washing and rubbing of the dyed silk at 4-grade or above was achieved under different flow statuses. The results further clearly indicate that the constructed method and self-built fluid dynamics coloration machine are helpful to investigate dye uptake behavior in different flow statuses, and are potentially beneficial to an efficient process and parameters design for cleaner production in textile coloration.     

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.     

Synthesis of novel 1:2 Fe-complexed dye containing polyamine groups

A Fe-complexed dye containing crosslinkable polyamine groups was synthesized through diazotization and coupling reaction, chlorination,amination and metallization.The structure of the Fe-complexed crosslinking dye was characterized by FT-IR and Atomic Absorption Spectroscopic techniques.The dyeing and light fastness properties of the Fe-complex on silk and wool were tested,and the results showed that the novel Fe-complex exhibited both high fixation and good light fastness.     

Application of anthocyanins as natural dye extracted from Brassica oleracea L. var. capitata f. rubra: dyeing studies of wool and silk fibres

Brassica oleracea L. var. capitata f. rubra (Red Cabbage) dye is composed mainly of natural pigment called anthocyanins used as a natural colourant. Wool and silk fibres were dyed with the aqueous extract obtained from red cabbage. The dyeing process was investigated and the combined effects of dyeing conditions on the colour yield parameter (K/S) were studied. Resulted fastness to wash, rubbing and light of the dyed fabrics were evaluated. Chemical Oxygen Demand (COD) and Biological Oxygen Demand (BOD₅₎ of the residual effluent were measured. Best dyeing conditions were found to be: 50 g/100 mL, pH 2, 60 min and 100 °C, respectively, for the red cabbage weight, pH, dyeing duration and temperature. Good fastnesses properties were found in both cases: for wool and silk fabrics. It was found also that the calculated biodegradability ratio (COD/BOD₅) of the residual bath of dyeing wool and silk with red cabbage extract are lower than 1.5 which means that these baths are biodegradable.     

丝素蛋白纤维的接枝聚合Ⅲ．丝素蛋白纤维的接枝聚合染色

本文提出了通过接枝聚合物将丝素蛋白纤维的染色的设想：在染料分子上引入丙烯酰基，然后将其接枝到丝素蛋白纤维表面。将2－羟基－4－丙烯酰氧二苯酮（HAOBP），1－羟基－2－丙烯酰氧蒽醌（HAOAQ）和1，5，8－三羟基－2－丙烯酰氧蒽醌（THAOAQ）等三种染料，分别用无引发剂存在下的接枝聚合法接枝到丝素蛋白纤维表面，使丝素蛋白纤维分别染成了浅黄、浅红和浅紫三种颜色。这样染色了的丝素蛋白纤维在浓酸或浓碱溶液中回流，未发生任何裉色现象，并且其热稳定性和紫外稳定性也得到了显著的改善。力学性能未下降。采用甲基丙烯酸甲酯（MMA）与染料单体共同进行接枝聚合染色，可以提高丝素蛋白纤维的光泽度，并可将接枝整理和染色两道工序合而为一。HAOBP、HAOAQ和THAOAQ在丝素蛋白纤维上的接枝率（mol单体／g丝），具有如下顺序，HAOBP＞HAOAQ＜THAOAQ。该顺序与它们的亲水性顺序恰好相反，这一结果支持了Imoto等人的无引发剂存在下的接枝聚合发生在丝素蛋白纤维的疏水区域的观点。     

高效液相色谱研究丝素亲核基团与一氯均三嗪型活性染料反应动力学

以异丙胺、对甲酚和甲醇分别模拟蚕丝丝素的氨基、酚羟基和醇羟基,应用高效液相色谱分析一氯均三嗪型活性染料与蚕丝丝素的不同亲核基团的反应速率.结果表明:在pH=8～10、70～95 ℃的条件下,染料的酚解总反应速率远大于染料的氨解总反应速率和醇解总反应速率.其中C.I.活性红24 和C.I.活性橙2在pH=9,95 ℃条件下的酚解总速率分别约为其氨解总反应速率的8.5倍和12.5倍,为其醇解总反应速率的23倍和50倍;该两染料的酚解效率分别为47.4和96.3,氨解效率分别为4.6和6.9,醇解效率仅为1左右.通过异丙胺-对甲酚-甲醇混合溶液(1∶ 10∶ 100,V/V)模拟蚕丝与染料的反应,研究一氯均三嗪型活性染料与丝素上亲核基团的反应选择性,推断出一氯均三嗪型活性染料染蚕丝的最适宜条件为pH=8～9,温度85 ℃左右.在此条件下,酚羟基在蚕丝的一氯均三嗪型活性染料染色中起主要作用,氨基起次要作用,而醇羟基的作用甚微.     

In situ fluorimetry: a powerful non-invasive diagnostic technique for natural dyes used in artefacts Part I. Spectral characterization of orcein in solution, on silk and wool laboratory-standards and a fragment of Renaissance tapestry

In this paper the potentialities of spectrophotometric and fluorimetric techniques for identifying the materials used in artistic textiles are investigated. A portable non-destructive instrument suitable to record fluorescence spectra on surfaces was set up and successfully experienced. A naturally occurring dye, orcein, which was widely used in antiquity for textile dyeing, has been spectrally characterized in both solution and powder. Laboratory samples of wool and silk orcein-dyed threads were analysed before and after ageing. An original fragment of Renaissance tapestry was also analysed. The textile (wool) and the colourant (orcein) were recognised by comparison with the data from the laboratory samples.     

Production,Partial Characterization,and Use of a Red Biochrome Produced by <Emphasis Type="Italic">Serratia sakuensis</Emphasis> subsp. nov Strain KRED for Dyeing Natural Fibers

We have described a novel red biochrome, 514 Da in size, produced by solid-state cultivation of a bacterial isolate obtained from garden soil. The growth requirements of the isolate, the chemical characteristics of the biochrome produced, and the application of the biochrome in dying of silk, wool, and cotton fabrics have been studied. The biochrome obtained after 52 h of incubation and having a λ _max of 535 nm was used for dyeing the fabrics. We found that silk, wool, and cotton fabrics dyed with this new natural red compound have high color strength values and dye uptake along with good color fastness as well as antibacterial activity.     

Dyes with high affinity for polylactide

Attempts were made to develop dyes with high affinity for polylactide as an alternative to the existent commercial disperse dyes. The dyes synthesized according to the affinity concept of dye to polylactide exhibited excellent dyeing properties on polylactide compared with the commercial disperse dyes.     

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.     

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.     

Effect of UV radiation on the dyeing of cotton fabric with reactive blue 13

For the present study, the cotton fabric and dye solution were irradiated to UV radiation for different times. Dyeing was performed using un-irradiated and irradiated cotton with un-irradiated and irradiated reactive blue dye. Different dyeing parameters such as temperature, pH and time were optimized using irradiated dye and irradiated cotton. The data of colour report were obtained from un-irradiated and irradiated cotton dyed with reactive blue dye using spectra flash (SF650). Colourfastness properties show that UV radiation of both cotton and dye powder has improved the grading of fastness from fair to good. It is found that UV irradiation has not only enhanced the strength of dye on irradiated fabric but also improved the dyeing properties.     

CI Reactive Black 5 dye as a visible crosslinker to improve physical properties of lyocell fabrics

Bi-functional reactive dyes have been used for reducing the fibrillation of lyocell fibres. The sole influence of CI Reactive Black 5 dye on the fibrillation tendency of lyocell single jersey knitted fabrics was investigated by dyeing with different concentrations (35 g/L for medium shade and 70 g/L for dark shade), dyeing without dyestuff and by decolouration process after each dyeing. The fibrillation tendency of lyocell fibres was accessed by means of fibre wet abrasion resistance and fibrillation number. Nitrogen content was used as indication of the amount of reactive dye in fabrics during dyeing and decolouration processes. The correlation between fibre fibrillation tendency and colour values of fabrics was found. Due to the fibrillation reduction, pilling formation in dyed lyocell fabrics was improved. As colour values can estimate the dye fixation and reduction in fabrics, reactive dye can be used as a visible marker for crosslinking effect on lyocell fabrics.     

Single bath process for imparting antimicrobial activity and ultraviolet protective property to bamboo viscose fabric

Bamboo viscose, a new cellulose-based textile material was investigated for biomedical applications such as ultraviolet protective ability and antimicrobial activity. Untreated bamboo viscose fabric was found to afford poor protection against UV radiation and also possessed minimal antimicrobial properties. To enhance UV protection characteristics, fabrics were subjected to different treatments viz., dyeing; finishing with commercial UV absorbers; and one-bath dyeing and finishing with UV absorber. Treatment conditions were optimized with regard to the concentration of UV absorber and dye. Results obtained showed that the UPF values increase with increase in UV absorber and dye concentration. Subsequently, a single bath process to apply both antimicrobial and UV protective treatments to bamboo fabric was studied. Results showed that both treatments are compatible for application from a single bath. The effectiveness of the antimicrobial agent was not adversely affected by the presence of an UV absorber and the treated fabric also retained excellent UV protective properties.     

Dye fixation and decolourization of vinyl sulphone reactive dyes by using dicyanidiamide fixer in the presence of ferric chloride

A synthetic polymer was synthesized and used for the improvement of dyeing properties as well as decolorization of textile waste water. Two dyes were selected having anthraquinone based Remazol Blue R and azo based Remazol Red RB. It was observed that the synthetic polymer can be used as fixer for the fixation of dye by crosslinking between dye and fibre, which not only improves the dyeing properties but also helpful to coagulate the colour after dyeing. By single point method the concentrations of synthetic polymer were calculated in residual after dyeing. It was examined that the residual synthetic polymer is helpful in colour removal efficiency by coagulation of polymer with dye to form heavy molecules which settle down and decolorization occurred. Colour removal efficiency was found dependents on pH, concentration of synthetic polymer and inorganic coagulant.     

Disperse dyes derived from 2-amino-5-mercapto-1,3,4-thiadiazole

Some novel heterocyclic monoazo dyes based on 2-amino-5-mercapto-1,3,4-thiadizole have been synthesized by coupling with various N-phenylacrylamide derivatives. The dyeing performance of these dyes was assessed on polyester fabrics. IR and visible spectra of the dyes were examined. The percentage dye bath exhaustion, fixation, and various fastness properties of the dyes were also determined. These dyes were found to give brownish-orange to reddish-pink shades on dyeing with good depth, levelness, and brightness on fabric. The dyed fabric showed a good to excellent fastness to washing, rubbing, perspiration, and sublimation.