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

Seven new upper rim functionalized azocalix[4]resorcinarene dyes have been synthesized by coupling calix[4]resorcinarene with different diazo compounds of p-chloroaniline, p-nitroaniline, p-toludine, p-anisidine, p-aminobenzoic acid, o-aminophenol, and aniline. The characterization of these dyes has been carried out by elemental analysis, FT-IR, ¹H- and ¹³C-NMR. Effect of solvents of varying dielectric constants on the absorption spectra of substituted and unsubstituted azocalix[4]resorcinarene dyes have been examined by UV-vis spectrophotometer. These azocalix[4]resorcinarene dyes have also been used for dyeing textile fibers like cotton, silk, and wool. Their dyeing and fastness properties have also been discussed.     

Prediction of CIELab data and wash fastness of nylon 6,6 using artificial neural network and linear regression model

We tried to predict the CIELab data and wash fastness values of scoured nylon 6.6 knitted fabric dyed with 1:2 metal-complex acid dyes and aftertreated using three different methods named as syntan, syntan/cation and full backtan by artificial neural network (ANN) with Levenberg-Marquardt algorithm and regression models. Afterward, the predicting performance of these models was tested and compared with each other using unseen data sets. We were able to achieve to predict the all colorimetric data satisfactorily such as L*, a*, b*, C, h ^o and wash fastness performance using both models. The statistical findings indicated that the regression models provide more accurate prediction for all colour data with an average error of 1% contrast to previous study. In terms of prediction of fastness, artificial neural network is a bit more useful than regression models for prediction of staining value on the nylon part of adjacent multifiber.     

Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics

A series of new azomethine dyes based on pyrazolone system have been synthesized via different routes. The solvatochromism for the dyes was evaluated with respect to spectroscopic properties in various solvents. The dyes were applied as disperse dyes on polyester fabrics and gave shade poor to excellent light fastness, washing, perspiration, sublimation, and rubbing fastness properties. Also the position of color in CIELAB coordinates (L*, a*, b*) and K/S value were investigated.     

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.     

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.     

Dyeing of wool with Marigold and its properties

This research work involves the dyeing of wool with Marigold as a source of yellow colour. To do this, wool yarns pre-treated with Alum as a colorless mordant, dyed with Marigold and then treated with different percentages of ammonia solutions. The chromaticity co-ordinates of samples measured in CIELAB system. TheL* values of all ammonia treated samples decreased and the values ofa*,b*,C* dependent on the ammonia solution. It can also indicate that the reflectance spectrum of treated samples decreases due to ammonia treatment. The rate of vertical wicking decreases on Marigold dyed treated with ammonia. Color hue of the Marigold dyed wool alters after washing with standard soap and ammonia after-treatment has no influence on washing fastness. The samples dyed with Marigold and after-treated with ammonia show a lower light fastness.     

Investigations on C-glycosyl flavonoids from Rhynchosia capitata,its antimicrobial and dyeing properties

Natural dyes extracted from a novel source Rhynchosia capitata (R. capitata) Heyne ex roth were applied to cotton fabric by applying traditional and pad dyeing processes using pre-, post- and simultaneous-mordanting techniques. Both dyeing processes were carried out in the presence of natural mordants: Myrobalan, Pomegranate rind, Rhizhophora mucronata fruits, Manjistha, and eco-friendly metallic mordants such as tannic acid, stannous chloride (SnCl₂), ferrous sulfate (FeSO₄), and copper sulfate (CuSO₄). The range of color developed on dyed materials was evaluated in terms of (L*, a*, b*, C*) CIELAB coordinates and dye absorption concentration on textile materials was studied by using K/S values. Natural mordant Rhizhopora mucronata fruits exhibited good absorption value. It was found that metallic mordants FeSO₄ and CuSO₄ exhibited higher K/S values than SnCl₂. For other mordants except FeSO₄ shade developed on cotton fabric varied from pale yellow to brown. The fastness properties ranged from good to excellent. High pressure thin layer chromatographic analysis for solvents of varying polarity has been investigated and maximum yield was obtained from 80 % aqueous ethanol fraction. Antimicrobial activity was carried out with the aid of two human pathogenic strains, Staphylococcus aureus and Klebsiella pneumonia and the cotton fabric dyed with plain extract of R. capitata shows good activity.     

Azo Acid Dyes Based on 2H-Pyrido[1,2-a]Pyrimidine-2,4(3H)-Dione with Good Tinctorial Power and Wetfastness - Synthesis,Photophysical Properties,and Dyeing Studies

A series of five azo acid dyes were synthesized using different diazotized aromatic amine sulfonic and carboxylic acids followed by coupling with 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione. The dyes were characterized by ¹H-NMR, ¹³CNMR, FTIR, and elemental analysis. They were applied on nylon, silk, and wool. Their fastness properties were evaluated and color on the fabric was assessed. Yellow, brown, and crimson dyeings with good fastness properties were obtained. The dyes are water soluble and showed absorption from 380 nm to 550 nm. Acid dyes from diazo component 4- aminonaphthalene-1-sulfonic acid (naphthionic acid) and 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid (H-Acid) were found to be more red shifted as compared to the other dyes. More red shifted absorption maximum was observed in acidic pH than in alkaline pH. The trends in vertical excitations obtained from Time Dependent Density Functional Theory calculations are in good agreement with the experimental absorptions.     

Synthesis and microbial studies of N-phenyl-2-(4-phenyl-thiazol-2-ylamino)-acetamide based disperse dyes and their dyeing performance on polyester fiber

Azo disperse dyes (D₁-D₁₃) were prepared by various diazotized aryl amines coupled with N-(phenyl)-2-[(4-phenyl-1,3-thiazol-2-yl)amino] acetamide. All the azo disperse dyes have been characterized by their percentage yield, UV-VIS spectroscopy, elemental analysis, IR spectroscopy, ¹H-NMR spectroscopy, and dyeing performance on polyester fiber. These dyes were applied to polyester fabric by HTHP method and their fastness properties were evaluated. All the dyes gave moderate to excellent fastness properties on polyester fiber. The main focus was to synthesize azo disperse dyes that give good dyeing property along with pharmacological activity. Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.     

The Use of Sumac as a Natural Mordant in Green Production of Iranian Carpet

Dyeing is a state-of-the-art realm of textile engineering, however, the emphasis on petroleum-based products is now shifting towards green fibers, particularly, green manufacturing processes. In the present work, a natural mordant, sumac, was extracted and used alone and in combination with alum (a mineral mordant) in silk fibers dyeing with madder and Reseda green dye to make the green production of Iranian carpet possible. The FT-IR ATR spectra of the washed, mordanted, and mordanted dyed silk fibers revealed bonding between silk fibers and green materials. The color of the silk fibers dyed with madder and Reseda extraction was quantified in terms of CIELab (L*, a*, and b*) and K/S values. The effects of different treatments on fastness properties including light, wash, and rubbing fastness were assessed by ISO standard test method.     

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.     

Synthesis and evaluation of a series of novel monoazo disperse dyes derived from N-carboxylic acid-1,8-naphthalimide on poly(ethylene terphthalate)

A series of novel monoazo disperse dyes based on N-carboxylic acid-1,8-naphthalimides have been synthesized via 4-(4-amino-1,8-naphthalimido) butanoic acid as diazo components and various couplers. The synthesized dyes were characterized with elemental analysis, differential scanning colorimetry, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, and UV-visible spectroscopic techniques. The molar extinction coefficient, wavelength maxima, and solvatochromism effect were obtained using chloroform, acetone, and N,N-dimethyl formamide as solvent. The results showed that the synthesized dyes had molar extinction coefficient of 20908 to 38939 l mol⁻¹ cm⁻¹, wavelength maxima of 409–549 nm, and positive solvatochromism by changing solvent from chloroform to N,N-dimethyl formamide. The synthesized dyes were applied on poly(ethylene terephthalate) using high temperature method. Dyes 1 and 2 showed high build-up properties on poly(ethylene terephthalate), whereas dyes 3 and 4 offered medium build-up. All the dyes offered excellent heat fastness, good wash and rubbing fastnesses on poly(ethylene terephthalate) fabrics. The hydrolysis of the synthesized dyes in alkali media indicated that the presence of a carboxylic acid group within the dye molecules provides alkali-clearable potential.     

Antibacterial properties and color fastness of silk fabric dyed with turmeric extract

The use of non-toxic and eco-friendly natural dyes on textiles has received much attention due to the increased environmental awareness in order to avoid some hazardous synthetic dyes. In the present study, an eco-friendly approach was developed to impart color and antibacterial properties to silk fabrics dyed with turmeric extract as a non-toxic natural colorant. The natural colorant was extracted from Curcuma Longa rhizome. Copper sulfate, ferrous sulfate and potassium aluminium sulfate were applied in a pre-metallization process as mordanting agents. Antibacterial properties of treated fabrics were evaluated against common pathogenic bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The effects of dye concentration and mordant types on the obtained color hues, antibacterial efficiency and color fastness of the fabrics were investigated. The results indicated that mordanted and dyed fabrics possessed desirable antibacterial properties. Complete antibacterial activity of the treated fabrics was obtained with 3 %owf (on weight of the fabric) copper sulfate. It was also shown that increasing the dye concentration could lead to a more efficient antibacterial activity on the mordanted dyed fabrics. An optimum level of the antibacterial activity was observed in the sample treated with 30 %owf of turmeric. Furthermore, the results of CIE L*, a*, b* values, FTIR, washing, light and rubbing fastnesses of the dyed fabrics were reported. The mordanted dyed silk fabrics exhibited desirable color fastness properties. These studies proved a direct relationship between the degree of antibacterial activity of the fabrics treated with turmeric and the metals ion concentration.     

Dyeing and DP treatment of sol-gel pre-treated cotton fabrics

Cotton samples were pre-treated with various sol solutions containing different alkoxysilanes (TEOS, GPTMS, APTES, and TESP-SA). The as-prepared cotton samples were dyed with 2 % owf Red and 4 % owf Blue. Furthermore, dyed cotton samples were after-treated with the alkoxysilanes. The alkoxysilane were also incorporated into the dyeing bath. The as- prepared cotton samples were subjected to a treatment with the non-formaldehyde durable press finishing agent BTCA in conjunction with the catalyst SHP. The textile materials were evaluated with respect to the colorimetric data (L*, a*, b*, ΔE*) and the color strength expressed in terms of K/S values. Tensile strength and dry crease recovery angles of the durable pressfinished samples were measured. The findings indicate that APTES and TESP-SA exert a significant influence on the color properties.     

Cytotoxic and Antibacterial Cembranoids from a South China Sea Soft Coral,Lobophytum sp

Chemical examination of a South China Sea soft coral Lobophytum sp. led to the isolation of three new α-methylene-γ-lactone-containing cembranoids, (1R*,3R*,4R*,14R*,7E,11E)-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide (1), (1R*,7S*,14S*,3E,11E)-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (2), and (1R*,7S*,14S*,3E,11E)-18-acetoxy-7-hydroperoxycembra-3,8(19),11,15(17)-tetraen-16,14-olide (3), along with eleven known analogues 4–14. The structures of the new compounds were elucidated through extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1–3 exhibited moderate cytotoxic activity against the selected tumor cell lines. Moreover, 2 and 3 were found to be moderate inhibitors against the bacteria S. aureus and S. pneumoniae.     

Dyeing, fastness, and deodorizing properties of cotton, silk, and wool fabrics dyed with gardenia, coffee sludge, Cassia tora. L., and pomegranate extracts

Four kinds of natural dying solutions (natural colorant extracts) were obtained by extraction from gardenia, coffee sludge, Cassia tora. L., and pomegranate using water at 90°C for 90 min with a liquor ratio (solid natural colorant material/solvent water, weight ratio) of 1/10. The dyeing, colour fastness, and deodorizing properties of cotton, silk, and wool fabrics dyed with natural colorant extracts were compared. It was found that these properties were significantly dependent on the concentration of extracts, the structure of colorant, and the kind of fabrics. The order of colour strength (K/S) is Cassia tora. L., pomegranate, coffee sludge, and gardenia. Colour fastness (light, water, and perspiration fastness) was in the range of 2nd–5th grades. The deodorizing performance of fabrics dyed with various natural colorant extracts was in the range of 50–99 %. The deodorizing performance increased in the order of gardenia < Cassia tora. L. < coffee sludge < pomegranate. Especially, the deodorizing performance of all fabrics dyed with pomegranate was found to be highest at 99 %.     

Sonicator dyeing of natural polymers with <Emphasis Type="Italic">Symplocos spicata</Emphasis> by metal chelation

Symplocos spicata (local name: Dom sheng) belonging to Family Symplococeae produces yellowish brown natural dye which has been used for dyeing textiles since ancient times by the Monpas tribe of Arunachal Pradesh. Symplocos spicata (Dom Sheng) was found in the Lumla area of Tawang district. Leaves of the plant are used by the Monpas and Tibetans for extraction of dye. Innovative sonicator dyeing with S. spicata showed that pretreatment with 2–4% metal mordant of the weight of the fabric is optimum showing very good fastness properties for dyed natural polymers such as cotton, wool, and silk. CIELab and K/S of the dyed fabrics were also evaluated. The superiority of sonicator dyeing over conventional dyeing has been established through this study.     

Superfine pigment dyeing of silk fabric by exhaust process

The surface of silk is modified by a cationic reagent, N-(3-chloro-2-hydroxypropyl) trimethylammonium chloride(CHTAC) in order to enable the fibre to be dyed with superfine pigments by an exhaust process. The effects of cationization pretreatment conditions such as the amount of cationic reagent, pH, treatment temperature and time on color yield are discussed in detail. The result shows that the condition suitable for modification treatment is that the concentrationc of cationic reagent is 10 g/l, pH 8, liquor to goods ratio of 100:1 and 60°C for 30 min. The white index decreases with the increase of alkali of cationic treatment. The crock fastness and wash fastness of silk dyed by pigment exhaust dyeing achieve 3–4 and 4 scale, respectively. The treated silk fabrics still retain a soft handle because the bending rigidity B and hysteresis 2HB increase slightly after cationization pretreatment and dyeing procedure. It has been demonstrated that properties of surface modified silk dyed with superfine pigment by exhaust process are acceptable.     

Dyeing properties and colour fastness of cotton and silk fabrics dyed with<Emphasis Type="Italic">Cassia tora L.</Emphasis> extract

A natural colorant was extracted fromCassia tora L. using buffer solutions (pH: 2–11) as extractants. The dyeing solution (Cassia tora L. extract) extracted using pH 9 buffer solution was found to give the highest K/S values of dyed fabrics. Cotton and silk fabrics were dyed withCassia tora L. extract at 60°C for 60 min with pre-treatment of various metal salts as mordants. It was found thatCassia tora L. extract was polygenetic dyestuffs and its major components were anthraquinones. Studies have been made on the effects of the kind of mordant on dyeing properties and colour fastnesses of cotton and silk fabrics. The K/S of cotton fabrics increased in the order of the dyeing using FeSO₄>CuSO₄>ZnSO₄>MnSO₄≅Al₂(SO₄)₃>NiSO₄>none, however, the K/S of silk fabrics increased in the order of the dyeing using FeSO₄>CuSO₄>ZnSO₄≅Al₂(SO₄)₃>MnSO₄≅NiSO₄>none. It was found that the K/S values of dyed fabrics were largely affected by the colour difference (ΔE) between mordanted fabric and control fabric. However, they were not depended on the content of mordanted metal ion of the fabrics. Mordants FeSO₄ and CuSO₄ for cotton fabric, FeSO₄, CuSO₄, and Al₂(SO₄)₃ for silk fabric were found to give good light fastness (rating 4).