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.     

Preparation of nano disperse dyes from nanoemulsions and their dyeing properties on ultramicrofiber polyester

Six nano disperse dyes were prepared using corresponding O/W nanoemulsions which were obtained with sodium laurylsulphate and caprylic triglyceride. The average particle size of the dyes prepared were in the range of 110–130 nm. Exhaust dyeing using nano dyes resulted in low exhaustion yields of 17–26 % on regular polyester fiber and 28–38 % on ultramicrofiber polyester. The observed low exhaustion yields of nano disperse dye can be explained by the solubilization of dye particles into surfactant micelles as well as the high stability of the nanoemulsions, these might reduce the capacity of dye uptake onto the fibers. However, higher K/S values of dyeings with nano dyes on ultramicrofiber sites compared to those on regular polyester sites suggested their potential to be more efficient dyes for finer denier microfiber polyesters.     

Synthesis of cationized anthraquinone dyes and their dyeing properties for meta-aramid fiber

Due to compact structure of meta-aramid fiber caused by the intermolecular hydrogen bondings of amide groups, the degree of crystallinity increased, thus its poor dyeing properties arises. Among commercial dyes used in many previous researches, the basic dyes showed comparatively higher exhaustion yields as comparing to those of disperse dyes and acid dyes. The anthraquinone moiety was adopted for good performances of light fastness on meta-aramid fiber. In this study, eight of anthraquinone dye was synthesized. The three of them were obtained from chloro-anthraquinone, by Ullmann reactions with the corresponding heterocylic residues such as morpholine and one of them was obtained from lueco quinizarine by condensation with the corresponding heterocylic residues. The others were prepared by quaternization from dyes above. The synthesized disperse and cationic dyes were dyed on meta-aramid fibers and investigated for their build-up dyeing properties and wash fastness.     

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.     

Synthesis of temporarily solubilized reactive disperse dyes and their application to the polyester/cotton blend fabric

Five temporarily solubilized reactive disperse dyes were synthesized and characterized. They were applied to polyester/cotton blend fabric using one-bath dyeing method without dispersing agent. The dye that has azonaphthalene chromophore seemed to not only be exhausted on polyester but also react with cotton. But other dyes were selectively dyed on polyester and showed limited uptake on cotton. Good levelling as well as moderate to good colour fastness was obtained with the dyes on P/C blend fabric.     

Eco-friendly dyeing of poly(trimethylene terephthalate) with temporarily solubilized azo disperse dyes based on pyridone derivatives

Dispersant-free PTT dyeing of temporarily solubilized azo disperse dyes based on pyridone moiety which contain β-sulfatoethylsulfonyl group was investigated. The dyes were successfully applied to PTT without the use of dispersants. The color yields of the dyes on PTT fabric were dependent on dyeing pH as well as dyeing temperature. The optimum results were obtained at pH 5–6 and 110 °C. The dyes showed alkali-clearing property and exhibited good to excellent fastness on the PTT fabric. The COD levels of the dyeing effluent from the temporarily solubilized disperse dyes were much smaller than those from commercial disperse dye.     

Dyeing of cotton and polyester/cotton blend with disperse dyes using sodium 2-(2,3-dibromopropionylamino)-5-(4,6-dichloro-1,3,5-triazinylamino)-benzenesulfonate

The cotton fabrics were pretreated by sodium 2-(2,3-dibromopropionylamino)-5-(4,6-dichloro-1,3,5-triazinylamino)-benzenesulfonate (DBDCBS) at alkaline condition of room temperature and then dyed with four disperse dyes having amino groups (C.I. Disperse Yellow 9, C.I. Disperse Red 11, C.I. Disperse Blue 56 and C.I. Disperse Violet 1) at acidic condition of high temperature. A novel hetero-bifunctional bridge compound,DBDCBS, has two reactive groups such as dichloro-s-triazinyl group andα, β-dibromopropionylamido group. The first has reactivity towards hydroxy group of cellulosic fiber and the second shows reactivity towards amino groups of disperse dye containing amino groups. The results indicate that it is possible to dye polyester/cotton blend at one-bath dyeing using one kind of disperse dye containing amino groups. Therefore, two kinds of dyeing methods such as two-bath process one-bath dyeing and one-bath process one-bath dyeing were investigated and their dyeabilities were compared. The differences between these two methods were negligibly small so that perfect one-bath one-step dyeing of polyester/cotton blend by one kind of disperse dye was achieved.     

Dyeing performance of disperse dyes based on 2-aminothiazole for cellulose triacetate and nylon fibers

A series of monoazo disperse dyes based on 2-amino-4-phenylthiazole was prepared using variousN,N-dialkylaniline derivatives as the coupling component. The dyes were characterized by IR spectral studies, visible absorption spectroscopy and elemental analysis. The dyeing performance of these dyes was assessed on cellulose triacetate and nylon fibers. These dyes were found to give a wide range of colour shades varying from bright red to royal blue with very good depth, brightness and levelness on fibers. The dyed fibers showed good to very good light fastness and very good to excellent fastness to washing, perspiration, rubbing and sublimation. The dyebath exhaustion and fixation on the fibers were found to be very good.     

Synthesis and spectral properties of phthalimide based alkali-clearable azo disperse dyes

The synthesis of a series of phthalimide based azo disperse dyes and their spectral properties were investigated. The azo dyes containing phthalimide and N-methyl phthalimide structure in diazo component were synthesized in order to compare their spectral properties. The synthesized dyes developed the color of yellow to violet and the N-substitution of the phthalimide gave a bathochromic effect on the color change. Most of the synthesized dyes exhibit negative solvatochromism so that the absorption band of dyes moves toward shorter wavelengths as the polarity of the solvent increases. In the case of halochromic effect, the bathochromic shift decreased steadily with the general electron donating capacity of the substituents in the coupling component, and became negative especially when more powerful electron donating groups are present in the coupling components ring.     

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.     

Dyeing properties of the disperse dyes containing cyano group based on benzisothiazole for polyester fabrics under alkali condition

One step dyeing of polyethylene terephthalate (PET) fabrics combining pretreatment and dyeing under the alkali condition was developed for cleaner production. One step dyeing of PET fabrics required that the dye used has good acid and alkali stability. In this paper, dyeing properties of three azo disperse dyes containing cyano group based on benzisothiazole, 3- (4-N-ethoxyl-N-cyanoethyl -phenyldiazenyl)-5-nitro-2,1-benzisothiazole (D1), 3-(4-N-ethyl-N-cyanoethyl- phenyldiazenyl)- 5-nitro-2,1-benzisothiazole (D2), and 3-(N-benzyl-N-cyanoethyl- phenyldiazenyl)-5-nitro-2,1-benzisothiazole (D3), were investigated under alkali condition. The results showed that polyester fabrics could be well dyed with D1, D2 and D3 under the acid condition. However, D1 was decomposed while dyeing at the alkali solution. D2 and D3 had excellent color yields under the alkali condition. The acid-alkali stability and the structure change were analyzed by UV-vis spectrum and high pressure liquid chromatography (HPLC). Gaussian 09 program package was used to optimize geometry by B3LYP method and 6-31G (d) basis set. The solvation energy of D1 in water was higher than those of D2 and D3. The electron withdrawn effect of the hydroxyl affected the energy gap of HOMO and LUMO orbits. D2 and D3 showed excellent stability in the strong alkali medium. And the dyed polyester fabrics with D2 and D3 at the alkali condition also had good fastness properties.     

Studies on antimicrobial activity for multidrug resistance strain by using phenyl pyrazolones substituted 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one derivatives in vitro condition and their dyeing performance

Heterocyclic monoazo quinazolinone based azo dyes derived by the diazotization of 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one with various phenyl pyrazolones based coupling components. All the heterocyclic azo dyes have been characterized by their percentage yield, UV-VIS spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy, and dyeing performance on silk, wool, nylon, and polyester fibers. All the dyes gave moderate to excellent fastness properties on each fiber. The main focus was to synthesize heterocyclic monoazo dyes that give good dyeing property along with pharmacological activity (anti bacterial and antifungal). Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.     

Dyeing properties of novel azo disperse dyes derived from phthalimide and color fastness on poly(lactic acid) fiber

The coloration of poly(lactic acid) (PLA) fiber with 18 carbocyclic monoazo disperse dyes bearing a hydrolyzable phthalimide ring fused to the aromatic ring of their diazo components has been investigated. The phthalimidyl nitrogen atom was substituted with either a n-butyl, sec-butyl, or isopropyl group, while the adjoining phenyl ring bore a substitution pattern typical of commercial colorants. There was a broad correlation between percentage dye exhaustion onto PLA and that onto polyester (PET) fiber, although significant differences in certain instances were apparent with no clear trends regarding dye structure. Attempts to explain the observed percentage exhaustion values by mapping them to calculated partition coefficient or solubility parameter values were unsuccessful. Wash fastness was relatively good compared to that of some conventional disperse dyes applied to PLA. As was found to be the case with PET, the wash fastness of dyes on PLA tended to be highest when their diazo ring was substituted with electron acceptors.     

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.     

Dyeing behavior of chemically modified poly(1,4-phenylene sulfide) fiber towards disperse,anionic, and cationic dyes

Poly(1,4-phenylene sulfide) (PPS) exhibits good dimensional stability and flame retardant characteristics but its commercial development as fibers is highly limited due to lesser dyeing and finishing characteristics. Hence in the present study, we focused on the anionic and cationic modifications of PPS to enhance its dyeing ability towards disperse, cationic, and anionic dyes. Novel sulfonation and chloromethylation-quaternization of PPS fiber were carried out to achieve an industrially viable dyeing process methodology. The chemically modified PPS fiber is dyed with disperse, cationic, and anionic dyes, and the dyeing adsorption efficiency is quantitatively studied using a dye-o-meter equipped with UV-visible absorption spectroscope. The ideal parameters for dye adsorption were determined as a function of dyeing time, material-toliquor ratio, dyeing temperature, carrier concentration, sulfonation, and chloromethylation. The fastness properties of the dyed fabrics were also studied. Overall, with a maximum dye uptake of 99 % and 90 % achieved for sulfonated PPS and quaternized PPS respectively, the optimized conditions can be readily scaled-up to the commercial dyeing of PPS fiber with disperse, anionic, and cationic dyes.     

Azocalix[4]pyrrole dyes: Application in dyeing of fibers and their antimicrobial activity

The dyeing performance of the azocalix[4]pyrrole dyes on fibers like nylon, wool, acrylic, and silk have been determined. Their fastness properties towards light, water, washing, and acid-alkali perspiration have been studied. The position of color in CIELAB coordinates (L*, a*, b*, H, and C*) was assessed. The azocalix[4]pyrrole demonstrated good antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Aspergillus niger. These super molecules exhibit bright shades on fabric with very good fastness properties.     

Synthesis and electropolymerization of 9-(4-vinylbenzyl)-9H-carbazole on carbon fiber microelectrode: Capacitive behavior of poly(9-(4-vinylbenzyl)-9H-carbazole)

The synthesis of 9-(4-vinylbenzyl)-9H-carbazole (VBCz) monomer and surface characterizations of thin film coating of poly(9-(4-vinylbenzyl)-9H-carbazole), P(VBCz) homopolymer on carbon fiber microelectrode (CFME) was performed. Coatings of polymer thin films obtained, with different initial monomer concentrations, were characterized by cyclic voltammetry, scanning electron microscopy and Fourier transform infrared reflectance-attenuated total reflection spectroscopy. Different initial monomer concentrations (1, 3, 5, and 10 mM) were electrodeposited in 0.1 M lithium perchlorate/acetonitrile solution. The characterization of the thin polymer films was performed on the surface of carbon fiber, and composition of polymeric structure was proposed. Capacitor behavior of modified CFME was studied by electrochemical impedance spectroscopy. The deposition charge of polymer growth affected the redox parameters of resulting coated CFME.     

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.     

Acid dyeing properties of meta-aramid fiber pretreated with PEO45-MeDMA derived from [2-(methacryloyloxy)ethyl] trimethylammonium chloride

A diblock copolymer (PEO₄₅-MeDMA) derived from [2-(methacryloyloxy)ethyl]trimethylammonium chloride (MeDMA) was synthesized and applied to the dyeing of the meta-aramid fibers with some acid dyes. This copolymer created positive charges on meta-aramid fiber surface and a strong attraction with anionic groups of acid dyes. Meta-aramid fabric was pretreated using the synthesized copolymer and then dyed with two commercial acid dyes. The dyeability was found to be directly dependent on the concentration of PEO₄₅-MeDMA, pH in the dyebath as well as dye concentration. The color fastness of the copolymer pretreated dyed fabric was also evaluated.     

Coloration of poly(lactic acid) with disperse dyes. II. Dyeing characteristics and color fastness

In Part 1 of this study, the dyeability, color shade, wash, light fastness and compatibility of homogeneous disperse dyes on PLA fabric and PET fabric were reported. The present paper (Part 2) focuses on the application of commercial disperse dyes to PLA fabric. Specific areas of investigation are the coloration properties of dyes originally intended for the production of high lightfastness polyester fabrics or for application to cellulose diacetate. The compatibility of the eight members of the dye set was investigated. In terms of lightfastness, the ratings were higher than that of conventional disperse dyes. In addition, the use of dye combinations to achieve synergistic uptake on PLA was explored leading to the pronounced synergism with a mixture of CI Disperse Blue 374 and 284.