A study of reusing vinyl sulfone based reactive dye for dyeing cotton fiber

Reactive dye is a popular dye for dyeing cotton fiber due to its very good color fastness which is explained by the formation of covalent bond between dye and fiber. In this study, practicality of reuse of reactive dye by compensating for the hydrolyzed part of the dye solution is examined. A monofunctional dye (vinyl sulfone type) was used and it was found that dyeing cotton fiber with reused dyebath is possible. Since bifunctional dye can improve the chance of dye-fiber bond formation, vinyl sulfone based bifunctional reactive dyes were also selected in this study. Three types of bifunctional dyes were used and they basically share the same vinyl sulfone group; other reactive groups are monochlorotriazine, dichlorotriazine and vinyl sulfone. Such dyes were chosen in order to compare their respective efficiencies under the effect of one common reactive group. The aim of this study was to compare the effect of hydrolyzed and unhydrolyzed proportions of mono-and bifunctional reactive dyes on cotton fiber and study the possibility and efficiency of the two different reuse dyebath systems.     

Dyeing properties of bi-functional reactive dyes on a novel regenerated cellulosic fiber

Three bi-functional reactive dyes such as Bis(vinylsulphone) type, Bis(monochlorotriazine) type and Bis(mononicotinotriazine) type were applied to regular viscose rayon and new regenerated cellulosic fiber (enVix®) which was prepared from cellulose acetate fiber by the hydrolysis of acetyl groups, and their dyeing properties and fastness properties were compared.enVix exhibited better dyeability and fastness than regular viscose rayon and these results were also explained by the differences in the supramolecular structure of these two fibers.     

Colorimetric studies of benzoquinoline based hot brand monoazo reactive dyes and their dyeing performance on various fibers

A series of hot brand monoazo reactive dyes (9a-l) were obtained by the coupling of diazotized 1Hbenzo[ g]pyrazolo[3,4-b]quinoline-3-ylamine (5) with various cyanurated coupling components (8a-l) in good yield. Synthesized dyes were characterized by various spectroscopic techniques. Their dyeing performances as reactive dyes have been assessed on silk, wool, and cotton fabrics. The percentage dye bath exhaustion and fixation on different fibers were found to be very good. The dyed fabric showed moderate to very good light fastness and good to excellent washing and rubbing fastness properties. Spectral properties and colorimetric data of synthesized dyes have also been studied in detail.     

1-Aminoanthraquinone Diazonium Salt on the Coupling Modification Dyeing of Silk Fibroin with Enhanced Color Fastness

Chromophore incorporated into the protein chains through residue modification on silk fibroin will be an important way to get new dyeing technology with improved color fastness. Herein, 1-aminoanthraquinone diazonium salt was prepared and used for the modified dyeing on tyrosine of silk fibroin. The silk after modified dyeing was measured by UV-Vis, FTIR, MS, ¹H-NMR, Data color, and other testing techniques. Interestingly, the resulting silk showed excellent rub and wash fastness. The enhanced color fastness is contributed by an electrophilic substitution reaction between 1- aminoanthraquinone diazonium salt and the ortho position of phenolic hydroxyl in tyrosine molecular. Moreover, the mechanical property of silk was protected effectively by the mild coupling modified dyeing, better than the traditional acid dyeing under high temperature for a long time. This facile strategy provides an alternative approach to silk dyeing and benefits the silk applications.     

Dyeing and fastness properties of a reactive disperse dye on PET, nylon, silk and N/P fabrics

Dyeing and color fastness properties of a reactive disperse dye containing an acetoxyethylsulphone group on PET, Nylon, silk and N/P fabrics were examined. The reactive disperse dye exhibited almost the same dyeing properties on PET fabric as a conventional disperse dye except the level of dye uptake. The most appropriate pH and dyeing temperature for the dyeing of Nylon fabric were 7 and 100°C respectively. The build-up on Nylon fabric was good and various color fastnesses were good to excellent due to the formation of the covalent bond. Application of the reactive disperse dye on silk fabric at pH 9 and 80°C yielded optimum color strength. The rate of dyeing on Nylon fabric was faster than that on PET fabric when both fabrics were dyed simultaneously in a dye bath, accordingly color strength of the dyed Nylon was higher. The reactive disperse dye can be applied for one-step and one-bath dyeing of N/P mixture fabric with good color fastness.     

Enzymatic grafting of lactoferrin onto silk fibroins for antibacterial functionalization

Enzymatic oxidation of tyrosine side-chains in proteins could produce reactive o-quinones that might subsequently react with the primary amino groups of functional compounds, which provided a worthwhile reference for functionalization of fibrion materials. In the present work the potential for using tyrosinase to graft the bovine lactoferrin onto Bombyx mori silk fibroin was examined. Lactoferrin could adsorb onto silk fibers and covalently bind to the previous enzymatically oxidized fibroin surface. The enzyme-generated quinones in silk fibers also might cause self-crosslinking of fibroin peptides, which led to beneficial changes of silk properties. For the fabric treated with tyrosinase and lactoferrin slight improvements of dyeability and strength were obtained in comparison to the control. The combinedly treated fabric showed encouraging resistance to S. aureus and E. coli, the antibacterial activities reached to 87.0 % and 76.4 %, respectively. The durability of the antibacterial silk was noticeably higher than that of the sample treated with lactoferrin alone.     

A study on combining natural dyes and environmentally-friendly mordant to improve color strength and ultraviolet protection of textiles

In this study, natural dyes were extracted from five plants, namely diospyros kaki, dioscorea cirrhosa, millettia (jixueteng), ecliptae, and macrocarpa nucuma, using environmentally-friendly solvents, including ethanol and deionized (DI) water. A plant mordant, tannin extracted from Emblica officinalis G., and a metal mordant, copper sulfate, were used in the pre-dyeing process. Cotton and silk fabric samples were treated using the five natural dyes without and with mordanting for comparison on their color strength and characteristics as well as protection against ultraviolet radiation (UVR). Results revealed that Emblica officinalis G. had the highest total phenol content, followed by dioscorea cirrhosa. The presence of abundant phenolic groups in the natural dyes and mordant makes them effective coloration agents for fabrics. Cotton and silk fabrics dyed using ecliptae without pre-mordanting had the highest K/S values. Silk fabrics had higher K/S values than cotton fabrics, indicating greater color strength in pre-mordanted silk treated with DI water-extracted dyes. Natural mordant used before treatment with natural dyes contribute to significant enhancement in color strength, and Emblica officinalis G. alone could darken the color of cotton and silk fabrics dyed with plant pigment. Moreover, treatment with natural dyes after mordanting can increase ultraviolet protection factor (UPF) and the enhancement in UVR protection is greater and more significant in cotton fabrics than in silk fabrics, and in fabrics treated with DI water-extracted natural dyes than in those treated with ethanol-extracted ones. In conclusion, pre-dyeing with natural mordant followed by treatment with natural dyes extracted using environmentally-friendly solvents can enhance significantly K/S and UPF, offering directions for manufacturing textiles without environmental hazards but with good appearance and health benefits.     

Relationships between antithrombogenicity and surface free energy of regenerated silk fibroin films

Silk fibroin (SF) was dissolved in calcium chloride/ethanol/water mixture (1/2/8 in mole ratio) at 70°C for 4 h. The dissolved silk fibroin was regenerated by casting the dialyzed solution into the films. The films were treated with 50% aqueous solution of methanol for different times, and their antithrombogenicity was evaluated byin vitro andin vivo tests.In vivo blood tests were made by a method of peripheral vein indwelling suture. It was found that the silk fibroin had a good anti-thrombogenicity and an absorbability even though the polymer showed foreign body reaction. Finally, the blood compatibilty of silk fibroin films which were subjected to structural change by the methanol treatment, was examined in connection with their interfacial surface energy, and a correlation between these properties was found to be present.     

Dyeing characteristics of Nylon,cotton and N/C mixture fabrics with reactive-disperse dyes containing a sulphatoethylsulphone group

The dyeing and color fastness properties of three reactive-disperse dyes containing a sulphatoethylsulphone group on Nylon, cotton and N/C mixture fabrics were examined. Reduction-clearing was more effective in removing the unfixed dyes than soaping since the reactive-disperse dye became hydrophobic during dyeing process. Nylon was dyed well with three reactive-disperse dyes at pH 5∼8 and difference in chemical structure between dyes did not affect the final color strength of the dyed Nylon fiber, but their build-up properties on Nylon were not so good. The color strength of the dyed cotton was not as high as that of Nylon. The color strength of cotton increased by lowering dyeing temperature when the reactive-disperse dyes having hydroxy group were used. Nylon absorbed more dye molecules than cotton in simultaneous dyeing, the color difference between Nylon and cotton could be reduced as the dyeing temperature decreased. N/C mixture fabric was dyed well at 60 °C with the reactive-disperse dyes having hydroxyl group when applied at pH 7 and 60 °C, and their build-up properties were good. It was also found that washing fastness and rubbing fastness of dyed Nylon, cotton and N/C fabrics with the reactive-disperse dyes were excellent, while light fastness was moderate.     

Dyeing of synthetic fabrics in water using azoic dyes based on boronic acid derivatives

Development of water-soluble dyes for the dyeing of different textile fabrics is essential for the textile industry due to ecological and economical reasons. In this study, a series of new azoic dyes were prepared by diazotization reaction between the phenyl boronic acid and different aniline derivatives, and their dyeing capacity in aqueous solution was evaluated. The synthesized boronic azo dyes present good water solubility and can dye polyamide (nylon), wool, silk, and cellulose acetate fabrics. The effect of factors such as concentration of dye, dyeing temperature, and pH on the level of color strength (K/S) was studied. The dyeing results showed that higher color strength K/S (about 16) and fastness properties (about 4/5) with boronic acid dyes were achieved at higher temperatures avoiding the use of surface agents, mordants, and other polluting chemical additives.     

Dye-resist properties of reactive dye-resist agents in acid dyeing of silk

The dye-resist effect of reactive dye-resist agents in acid dyeing of silk was investigated. The dye-resist agent containing dichlorotriazine achieved a higher resist effectiveness than others since they make a charge barrier against diffusion in the silk fiber periphery due to the high reactivity of dichlorotriazine group. Especially, the increase in the number of ionic groups in acid dyes leads to better electrostatic repulsion of reactive dye resist agent treated silk and thus improves the resist effectiveness. However, the hydrophobicity effect of acid dyes on the dye-resist properties was relatively minor.     

Synthesis,characterization and ultrafiltration of reactive dyes. Application by exhaustion and/or ink-jet printing. IV.

Three new bis azo reactive dyes of different metallic salts (Na, K, Li) were synthesized. The synthesis was obtained by diazotization of 4-amino-2:5 di methoxy phenylene-beta hydroxyl ethyl sulphone sulphate ester and coupling with 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (H-acid) (moles ratio 2:1). The dyes were purified-concentrated by ultrafiltration technology, characterized and applied on cotton, wool and nylon 6,6 fabric by exhaustion (dyeing) and by ink-jet printing. Fastness properties of the dyeings were measured. Wash fastness was investigated according to international standard methods and was found to be very good to excellent in all cases, while light fastness values were medium to low. Ink-jet ink formulations were prepared using the ultra filtrated reactive blue dyes UF RB(a-c) and their properties pH, conductivity, surface tension and viscosity were monitored over a period of 90 days. The inks were used to print digitally cotton and nylon 6,6 samples and wash- and light fastness properties of the prints were measured. Wash fastness properties were excellent while light fastness values are low Colour measurements of the dyeings and prints were conducted.     

Grafting of tyrosine-containing peptide onto silk fibroin membrane for improving enzymatic reactivity

During enzymatic modifications of silk fibroins, the accessibility of tyrosinases to the reactive sites was limited owing to the steric hindrance of tyrosine residues in the fibroin proteins. To improve the reactivity of silk fibroin, a tyrosine-containing peptide (TyrP) was covalently grafted onto the fibroin surfaces using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC). Enzymatic oxidation of the modified fibroins was subsequently carried out with a mushroom tyrosinase, followed by coupling of ε-polylysine (ε-PL) with the generated o-quinone residues of silk fibroins. The efficacy of grafting reaction was examined by means of SDS-PAGE and amine acid analysis. The results indicated EDC treatment might cause the direct self-crosslinks of silk fibroins and TyrP-bridged cross-links of fibroin molecules as well, which led to a noticeable increase in the molecular weight of fibroin proteins. TyrP-grafted fibroins displayed higher reactivity compared to the untreated, and more ε-PL was bonded to the fibroin surfaces when incubating with tyrosinase, resulting in improved wettability and mechanical property. The presented work offers an efficient alternative for the enzymatic modification of the fibroin-based materials with tyrosinase.     

Synthesis and characterization of novel reactive dyes with simultaneous insect-repellent and anti-bacterial properties

N,N-Diethyl-m-toluamide (DEET) is widely used as an insect-repellent. Sulfonamides are an important class of anti-bacterial drugs. In order to combine the strength of anti-bacterial activities of sulfonamides and insect-repellent property of DEET, three azo reactive dyes were designed and synthesized. To do this, the diazoniom salts of sulfonamides viz. 4-amino-N-(4-methyl-2-pyrimidinyl) benzene sulfonamide, 4-amino-N-(4-dimethyl-2-pyrimidinyl) benzene sulfonamide and 4-amino-N-(4,6-dimethyl-2-pyrimidinyl) benzene sulfonamide were prepared using HCl and NaNO₂. The resulting diazoniom salts were then coupled to the coupling component containing N,N-diethyl-m-toluamide to produce the novel dyes. The synthesized dyes were filtered off and then purified. To investigate and analyze the dyes, analytical methods such as ¹H-NMR, FTIR, UV-visible spectroscopy, and elemental analysis were used. Consequently, the anti-bacterial activities of dyes were measured with E. coli and P. aeruginosa as a Gram-negative strain and S. aureus and S. mutans as a Gram-positive strain according to MIC method. The insect-repellent efficacy of the dyes was studied using standard methods for Anophle mosquito repellent. The results confirmed anti-bacterial and insect-repellent activity of the dyes.     

Novel cationic softener containing MCT reactive dyes for cotton: Synthesis and characterization

Two novel cationic softener containing mono-s-chloro triazinyl reactive dyes together with their analogues were designed. The dyes were synthesized via reacting an N,N-dimethyldodecylamine with p-nitrobenzyl bromide. The resultant was reduced using stannous chloride and hydrochloric acid to produce the primary amine. The quaternary ammonium salt containing primary amine was then diazotized to produce diazonium salt part of azo dye. The diazonium salt was then coupled to H-acid/J-acid reacted with cyanuric chloride and sulfanilic acid. The analogue dyes were prepared via the same route without quaternary ammonium salt making stage. The chemical structures of the novel dyes were characterized by FTIR, ¹H-NMR, and elemental analysis. The spectroscopic properties of the dyes were determined in terms of λ _max and ? _max in aqueous solution.     

Novel cationic softener containing MCT reactive dyes for cotton: Simultaneous dyeing and functional finishing

The cationic softeners containing MCT (monochloro-s-triazinyl) reactive dyes were employed on the dyeing of cotton fabrics. The substantivity, exhaustion, and fixation of the dyes were investigated. It was found that these functional dyes could be effectively introduced to cotton fibers to achieve simultaneous coloration and functional finishing effects. All the dyed fabrics exhibited softening efficacy. The dyes offered excellent washing fastness on cotton substrate. Light fastnesses of the dyes on the substrate were poor.     

Dispersant-free dyeing of poly(lactic acid) knitted fabric with temporarily solubilized azo disperse dyes

Poly(lactic acid) (PLA) is known for environmentally friendly material as it is derived from annually renewable crops and biodegradable. Dispersant-free dyeing of PLA fabric with three temporarily solubilized azo disperse dyes which contain β-sulfatoethylsulfonyl group was investigated and their dyeing and fastness properties were compared with those of commercial disperse dyes. The temporarily solubilized azo disperse dyes were successfully applied to PLA fabric without the use of dispersant. The color yield on PLA fabric was dependent on dyebath pH and dyeing temperature as well. The optimum results were obtained at pH 7-8 and 110 °C. The dyes showed markedly higher color yield on PLA fabric when compared to commercial disperse dyes. Wash fastness was very poor to poor but light fastness was good. The COD levels of the dyeing effluent from the temporarily solubilized disperse dyes were considerably lower than those from commercial disperse dyes.     

Synthesis, characterization and application of quinazolinone based reactive dyes for various fibers

Seven hot brand heterocyclic mono azo reactive dyes (7a–g) have been synthesized by coupling diazotized 2-phenyl-3{4′-[(4″-aminophenyl)sulphonyl]phenyl}-quinazoline-4(3H)-one-6-sulphonic acid (4) with various 2-chloro-4-nitro anilino cyanurated coupling components (6a–g) and their dyeing performance on silk, wool, and cotton has been assessed. The purity of dyes was checked by thin layer chromatography. These dyes were identified by recording IR and ¹H-NMR spectra. The λ _max, R _f value, %exhaustion, %fixation, light fastness, wash fastness, rubbing fastness, reflectance (%R) value, and K/S value have also been studied.     

Synthesis of some new thermally stable reactive dyes having 4(3<Emphasis Type="Italic">H</Emphasis>)-quinazolinone molecule for the dyeing of silk,wool, and cotton fibers

Diazotized 3-{4-[2-chloro-4-amino-5-carboxybenzyl]-5-chloro-2-carboxyphenyl}-6-iodo-2-phenylquinazolin-4(3H)-one (4) was coupled with various p-nitro anilino cyanurated coupling components (6a-j) to give the corresponding quinazolinone based reactive dyes (7a-j) in reasonable yields. All the reactive dyes (7a-j) were characterized by spectroscopic technique and elemental analysis. These dyes were applied to silk, wool, and cotton fibers as reactive dyes and their spectroscopic data, colorimetric data, antimicrobial activity, thermal stability, and fastness properties were evaluated.     

Removal of some cationic dyes from aqueous solution by acrylamide- or 2-hydroxyethyl methacrylate-based copolymeric hydrogels

In this study, anionic hydrogels were prepared using a crosslinker (N,N′-methylenebisacrylamide) through a free radical addition reaction in aqueous solutions of neutral acrylamide or 2-hydroxyethyl methacrylate monomer and anionic monomers, mesaconic acid or aconitic acid. Cationic dyes along with safranine (azine-), nile blue (oxazine-) and methylene blue (thiazine-) were selected as models of pollutants, and adsorption of these dyes onto the hydrogels was investigated. To examine the effect of concentration on adsorption, dye solutions prepared with a concentration range of 5–50 mg l^?1 and 0.1 g hydrogel at 25 °C were exposed to the hydrogels until equilibrium was established. Dye adsorption onto the hydrogels was found to be an L type Giles adsorption isotherm. Monolayer sorption capacity and adsorption constant values were calculated from the Langmuir plots. To calculate R_L values, a non-dimensional analysis was used and they were always found to be 0<R<1. In other words, the hydrogels were favorable for adsorption of these dyes. Aqueous solutions of dyes were observed to interact with hydrogels in the following order: oxazine > azine > thiazine. Furthermore, the higher the number of carboxyl groups in the hydrogel composition, the higher the adsorbed amount of substance.