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, color fastness and antimicrobial properties of some mono and disazo disperse dyes derived from thiazole moiety

Three series of mono and disazo disperse dyes were synthesized from 2-amino-4-(pyridin-3-yl) thiazole. The structure of the synthesized dyes was confirmed by elemental analysis, ultraviolet-visible, infrared, proton and carbon nuclear magnetic resonance and mass spectroscopy. The dyeing parameters, perspiration, wash and light fastness of eighteen azo disperse dyes on polyester have been investigated. Application of these dyes on polyester fabric gave yellow to reddish hues for mono azo derivatives and reddish to dark brown hues for disazo derivatives with fair to moderate light fastness and moderate to good wash and perspiration fastness grade. In addition, the synthesized dyes were screened for their antimicrobial activities against some gram positive, gram negative bacteria and fungi. Some of the prepared dyes gave excellent results against most of the tested organisms.     

Dispersant-free dyeing of polyester with temporarily solubilized azo disperse dyes from indole derivatives

Temporarily solubilized azo disperse dyes based on 1,2-substituted indoles were synthesized and characterized. Dispersant-free dyeing of polyester by using the synthesized dyes has been investigated. The colour yields of the dyes on the polyester fabric were found to be highly dependent on the dyeing pH, optimum results being obtained at pH 5. The dyes exhibited good to excellent fastness properties on polyester while lightfastness was moderate.     

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.     

One-bath dyeing of PET/cotton blends with azohydroxypyridone disperse dyes containing a fluorosulfonyl group

Azohydroxypyridone disperse dyes containing a fluorosulfonyl group were dyed on PET/cotton blends and their dyeing and fastness properties were investigated. Specially, the azohydroxypyridone dyes containing a nitro group in place of the fluorosulfonyl group in the para position to azo group were synthesized in order to compare their dyeing and fastness properties on PET/cotton blends with those of fluorosulfonyl-substituted analogues. As these dyes can be alkali cleared in the same bath, a one-bath dyeing method was used and the results were compared with that of a conventional two-bath dyeing method. In particular, the cross-staining of cotton was studied in order to assess their suitability for the one-bath dyeing of PET/cotton blends.     

Thiazole based disperse dyes for nylon and polyester fibers

Nine disperse dyes have been synthesized by diazotization of 2-amino-4-(p-nitrophenyl)-5-nitrothiazole and coupled to substituted N-alkylanilines. Spectral properties in the IR and visible range of the dyes obtained were investigated. The dyeing performance of these dyes was assessed on nylon and polyester fibers. These dyes were found to give reddish brown to bluish violet shades on dyeing with very good depth, brightness and levelness on nylon and polyester fibers. The dyed fibers showed fairly good light fastness, very good to excellent fastness to wash, rubbing, perspiration and excellent fastness to sublimation. The dyebath exhaustion and fixation on the fiber were found to be very good.     

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.     

Light fast monoazo dyes with an inbuilt photostabilizing unit: Synthesis and computational studies

A series of monoazo disperse dyes with a photostablilizing o-hydroxycarbonyl moiety was incorporated resulted in the enhancement of the light fastness properties on polyester and nylon substrates as compared to the dyes that do not possess the photostablilizing moiety. The geometries of the azo and the hydrazone tautomeric forms of all dyes were optimized at B3LYP/6-311+G(d) and electrophilicity index was calculated for propensity of the moiety to absorb electrons. The values of absorption and stability trend of the dyes were in good agreement with the trend of experimental light fastness values. These disperse dyes possess excellent wash fastness and moderate to good sublimation fastness on hydrophobic substrates.     

Polymeric dyes based on thiadiazole derivatives

A series of polymeric dyes were synthesized by free radical addition polymerization of monomeric dyes. The 2-amino-5-mercapto-1,3,4-thiadiazole was diazotized and coupled with various N-arylmaleimides to give monomeric dyes. All the polymeric dyes were characterized by elemental analysis, infrared spectroscopy, visible absorption spectroscopy, viscometry, and thermogravimetric analysis. Color and dyeing properties of the polymeric dyes were discussed by comparing them with those of the corresponding monomeric dyes. The dyeing performance of these dyes was assessed on nylon fiber. These dyes were found to give various color shades with good to very good depth and levelness on the fiber. The dyeing of the monomeric dyes showed moderate fastness to light and good to excellent fastness to washing, perspiration and sublimation and their corresponding polymeric dyes showed excellent fastness properties. The dyebath exhaustion and fixation on nylon fiber has been found to be good.     

Dyeing performance of the azo dyes containing trifluoromethyl group for polyester fabrics and its single crystal structure

The structures of disperse dyes and their intermolecular interactions have important impacts on dyeing and printing performances for polyester fabrics. The fluorine dyes show some unique molecular stability and photochemical properties. The dyeing property of the azo dye containing trifluoromethyl group for polyester fabrics, 4'-(N-acetoxyethyl-Nethyl)- amino-2-bromine-4-nitro-6-trifluoromethylazo- benzene (D1), was investigated and compared with the similar structure disperse dye. The results show that the high color yield and good exhaustion of the dyed PET fabrics could be obtained. The polyester fabrics dyed with D1 had excellent light fastness. Its single crystal was prepared and the supramolecular interactions were solved by X-ray diffraction. Dye D1 formed triclinic crystals in a trimeric packing mode. The C-F bond distances of CF3 are 1.2730 Å, 1.2240 Å and 1.2900 Å, respectively. The two benzene rings linked azo unit (-N=N-) are obviously twist. The dihedral angle of the two benzene rings is 50.23 o. There are six weak hydrogen bonds around trifluoromethyl group in the intramolecule and intermolecule. The excellent light stability of the dye should be attributed to its unique supramolecular structure.     

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.     

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.     

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.     

Dyeing of meta-aramid fibers with disperse dyes in supercritical carbon dioxide

Dyeing characteristics of meta-aramid fibers were investigated in supercritical carbon dioxide by employing three disperse dyes and a carrier. The effects of dyeing temperature, pressure, time, dye concentration, CO₂ flow, and carrier concentration on dyeing properties were investigated. The results showed that meta-aramid fiber could be dyed in supercritical carbon dioxide. Its color depth was improved with increasing dyeing temperature, pressure, time, dye concentration, CO₂ flow, and carrier concentration. Moreover, the color depth could be significantly improved by adding the carrier. The dyeing procedure of supercritical carbon dioxide fluid did not influence the chemical structure and antistatic properties of the meta-aramid fiber. The maximum decomposition temperature and breaking strength of the dyed meta-aramid fiber are slightly increased. The dyed meta-aramid fiber in supercritical carbon dioxide had good fastness, which was rated at 4–5.     

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 and fastness properties of vat dyes on meta-aramid woven fabric

meta-Aramid fibers have an excellent heat-resistant property and are widely used for protective clothings such as fire-fighter suit and racing suit. They can also be used as military uniforms such as flight suit or army uniform. Vat dyes are specially used for military uniforms owing to outstanding fastness properties, earth tone shade, and near infrared (NIR) camouflage. In this study, 100 % meta-aramid woven fabric was dyed with three vat dyes using an exhaustion method and their dyeing and fastness properties were investigated. Color yields of the vat dyes on the meta-aramid fabric were found to be dependent upon dyeing temperature, liquor ratio, amount of reducing agent, and amount of salt. Dyeing behavior of the vat dye on the meta-aramid fiber was very similar to that on cellulose fibers. It was found that the meta-aramid fabric dyed with 1% owf of C.I. Vat Green 1 satisfied the tolerance of the reflectance spectrum of forest green color in the Korean military standard. Thermal stability and mechanical property of the meta-aramid fabric did not significantly affected by the vat dyeing process. Wash and perspiration fastness was generally good but rubbing and light fastness was unsatisfied.     

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 properties and color fastness of 100% <Emphasis Type="Italic">meta</Emphasis>-aramid fiber

Dyeing characteristics and fastness of 100 % m-aramid fiber with some commercial dyes were investigated on various dyeing conditions, such as using a swelling agent and electrolyte as auxiliaries. Among commercial dyes used, the basic dyes showed comparatively higher exhaustion yield comparing to those of disperse dyes and acid dyes. Under acidic conditions in the range pH 3 to 5, preferably between pH 3 and 4, the stability of cationic dyes could be enhanced leading to higher adsorption. Dye exhaustions of trichromatic dyes were increased proportionally to concentration of swelling agents ranging from 1 to 4 g/l. The addition of electrolyte provided increased K/S values after washing process compared with those of blank dyeings, where the greatest effect was observed with NaNO₃.     

High Light-Fastness Acid Dyes Synthesized from Corresponding Anthraquinone Chromophore Utilizing a Sulfonation Reaction. I. Dye Synthesis and Characterization

As the diameter of polyamide fibers decreased to finer denier, the dyeing fastness tends to be deteriorated due to the increase of their surface area, particularly both light fastness and wash fastness. In this study, three acid dyes were synthesized utilizing a sulfonation reaction starting from corresponding hydrophobic dye (for yellow and red dye) and dye intermediate containing a sulfonic acid group (for blue dye), those featured by high light fastness property. A Gaussian structural prediction model was used to determine the structure of the acid dyes prior to dye synthesis, and the optimal structures of three acid dyes were analyzed. Dye structures prepared were confirmed by ¹H-NMR, mass spectroscopy, and elemental analysis. By using a UV-vis spectrophotometer, the absorption maxima and molar extinction coefficient were also measured for three acid dyes comparing to that of the corresponding disperse dye or blue dye intermediate. Judging from spectroscopic data, the introduction of sulfonyl groups led to increase of molar extinction coefficient and a bathochromic shift.     

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.