Azomethine Dyes Research Articles

Long-Range Proton Transfer in 7-Hydroxy-Quinoline-Based Azomethine Dyes: A Hidden Reason for the Low Efficiency

In the tautomeric Schiff bases, derived from 7-hydroxyquinoline, two competitive channels are possible upon excitation of the enol tautomer, namely proton transfer (PT) through intramolecular hydrogen bonding to the corresponding keto form and trans-cis isomerization around the azomethine double bond. The former leads to switching, based on twist-assisted excited state intramolecular PT, where the long-range proton transfer can occur as a targeted process. The latter, determined by the flexibility of the crane part, reduces the efficiency of the main targeted process. In previously studied molecular switches based on the 7-hydroxyquinoline skeleton, only the intramolecular PT photo-process undergoing from the excited enol form towards the keto tautomer, which is in most cases barrierless, has been discussed. Therefore, in the current study, the ground state PT properties and isomerization of (E)-8-((phenylimino)methyl)quinolin-7-ol and (E)-8-(((pentafluorophenyl)imino)methyl)quinolin-7-ol are investigated in depth using the MP2 methodology, while the excited state energy profiles are calculated with the ADC(2) method. The obtained results are discussed in light of the existing experimental data.

Synthesis & characterization of heterocyclic disazo - azomethine dyes and investigating their molecular docking & dynamics properties on acetylcholine esterase (AChE), heat shock protein (HSP90α), nicotinamide N-methyl transferase (NNMT) and SARS-CoV-2 (2019-nCoV, COVID-19) main protease (Mpro)

In the study, by using 5-amino-4-arylazo-3-methyl-1H-pyrazole derivatives and 2‑hydroxy-5-(phenyldiazenyl) benzaldehyde; eight novel heterocyclic disperse disazo-azomethine dyes were synthesized, their chemical structures were characterized via FT-IR and 1H NMR studies. Synthesized compounds were also investigated computationally by performing various techniques. In the computational part of the study, geometry optimizations, frequency analyses, frontier molecular orbital (FMO) calculations, molecular electrostatic potential (MEP) map calculations, FT-IR and NMR spectral analyses were performed on the compounds. Additionally, to reveal their potentials against SARS-CoV-2 main protease (SARS-CoV-2 Mpro), acetylcholine esterase (AChE), heat shock protein (HSP90α) and nicotinamide N-methyl transferase (NNMT), molecular docking calculations were also performed on the synthesized compounds. Molecular dynamics (MD) simulations were carried out on the top-scoring ligand-receptor complexes to evaluate the stability of the complexes and the interactions between ligands and receptors in more detail. Results showed that synthesized compounds can interact with all these four receptors effectively and can be promising structures for further studies.

Singlet and Triplet State Properties and Singlet Oxygen Yield of an Amino-Acyl-Quinoxalinone Yellow Dye.

Amino-acyl-quinoxalinone yellow dyes are cyclised analogues of the yellow azomethine dyes developed for, and still used in, silver halide colour photography. Unlike image azomethine dyes, which are rapidly deactivated in their excited states by torsion about the azomethine bond, amino-acyl-quinoxalinone dyes have an interesting photophysics because torsion is not possible due to their cyclised structure. We report results from studies on singlet and triplet state properties, and singlet oxygen yields, of the yellow dye, 7-diethylamino-3-(2,2-dimethyl-propionyl)-5-methyl-1-phenyl-1H-quinoxalin-2-one, in polar and nonpolar solvents. The dye photophysics is characterised by a weak fluorescence, with a solvent dependent emission yield (ΦF ≈ 0.002-0.004), and short singlet state lifetime (τexpt ≈ 20-50ps), both increasing by a factor of ≈2 in going from polar acetonitrile to non-polar dioxane as solvent. DFT ZINDO calculations show a transition involving significant electron transfer from the diethyl-amino group into the carbonyl region of the molecule. In solution, in the presence of oxygen, the triplet state decays almost exclusively by oxygen quenching, and singlet oxygen is produced in high yield (Φ∆ ≈ 0.5-0.55). The triplet state absorbs across the 450-750nm region with maxima around 480 and 650nm, and moderate molar absorption coefficients (ca. 6000-8000M-1cm-1). In a glass at 77K, triplet decay gives a red phosphorescence, with λmax ≈ 640-650nm, and a ≈ 0.25s lifetime. If singlet oxygen yields are a good indication of triplet yields, then internal conversion and intersystem crossing occur with roughly equal efficiency.

Design, synthesis of new magenta dyestuffs based on thiazole azomethine disperse reactive dyes with antibacterial potential on both dyes and gamma-irradiated dyed fabric

A series of new magenta azomethine reactive disperse dyes were synthesized and applied into polyester/cotton blend fabrics. Various spectroscopic and analytical techniques characterized all the synthesized dyes. The obtained data and theoretical values of all the synthesized molecules were in good agreement with the proposed molecular structure. These dyes have proven their efficiency in dyeing blend fabrics, as they give satisfactory results in fastness properties, colorimetric data and exhaustion, fixation study. Moreover, the dyed fabrics were tested for ultraviolet protection factor and offered high ultraviolet protection. The advantage of synthesizing these dyes is quite facile, and scale-up is feasible, preferring industrial dyeing applications. The designed thiazole azomethine dyes exhibited broad-spectrum antibacterial agents against MDR Gram-positive and Gram-negative bacterial isolates, which will facilitate their rational usage in multiple therapeutic applications. Our findings also demonstrate the possibility of using gamma radiation for sterilization of dyed fabrics and the ability of radiation to intensify their antibacterial activities, thereby inhibiting any bacterial growth on the surface of textiles. The molecular docking study showed good binding as a preferred mode between the dyes and DNA gyrase's active site (2XCT).

Two new dichroic dyes: Quantum chemical modeling, synthesis, optical properties and their application in polarizing films

In the present work, the quantum chemical calculations of the molecular structures of the two newly synthesized dichroic dyes:2-methoxy-4-((1E)-((4-(phenyldiazenyl)phenyl)imino)methyl)phenyl isonicotinate (IN-1);2-methoxy-5-((1E)-((4-(phenyldiazenyl)phenyl)imino)methyl)phenyl isonicotinate (IN-2) have been predicted using Density Functional Theory (DFT) in solvent dimethylformamide (DMF). The geometries of the dichroic dyes were optimized using the B3LYP/6-311+G* level of the theory. In addition, the electronic spectra of these compounds in solvent DMF were carried out using the same method. After quantum-chemical calculations dichroic dyes for optoelectronic applications were synthesized. Based on polyvinyl alcohol (PVA) and the new synthesized azomethine dyes polarizing films for UV/Vis regions of the spectrum were developed. The main optical parameters of polarizing PVA-films (Transmittance and Polarization Efficiency) have been measured and discussed.

Optimization, Spectroscopic (Excited States, UV/Vis, Polarization) Studies, FMO, ELF, LOL, QTAIM, NBO Analysis and Electronic Properties of Two New Azomethine Derivatives: A Theoretical and Experimental Investigations

In the current study, the molecular structures of the two new azomethine dyes such as AAFOH-1 and AAFOH-2 have been investigated with the use of density functional theory (DFT/B3LYP/6-311+G(d)) in a DMSO solvent for the first time. The electronic spectra of the new dyes in a DMSO solvent were carried out by temporally dependent density functional theory (TD-DFT) method. The computed absorption spectral data of the investigated molecules are in good agreement with the experimental data, thus allowing an assignment of the UV/Vis spectra. The equilibrium geometry, the HOMO and LUMO molecular orbitals, excitation energies, oscillator strengths and natural bond orbital (NBO) analysis for the molecules have also been calculated and presented. The electron location function (ELF), localized orbital locator (LOL), and quantum theory of atoms in molecules (QTAIM) analyses were also carried out. On the basis of polyvinyl alcohol (PVA) and the new synthesized azomethine dyes polarizing films were developed. The main optical parameters of polarizing PVA-films (transmittance, polarization efficiency, and dichroic ratio) have been measured and discussed. Anizotropy of thermal conductivity of the PVA-films have been studied.

Novel efficient nonlinear optical azo- and azomethine polymers containing an antipyrine fragment: synthesis and characterization

Set of azo- and azomethine dyes with antipyrine fragments, including one bent shaped azomethine, its homo- and copolymers with MMA were synthesized. The materials demonstrated efficient refractive nonlinear optical response via self-action effect.

СИНТЕЗ ТА ФОТОВОЛЬТАЇЧНІ ВЛАСТИВОСТІ СИМЕТРИЧНИХ БІС-АЗОМЕТИНІВ З АКЦЕПТОРНИМИ ЗАМІСНИКАМИ У 4,4'-ПОЛОЖЕННІ

Two new symmetric azomethine dyes capable of photoinduced isomerization were synthesized by condensing symmetric bis-aldehyde (obtained by the reaction of epichlorohydrin with 4-oxybenzaldehyde) with 4-nitroaniline and 4-chloroaniline, respectively. The yield of the target products decreases with the transition from nitro-substituted azomethine to chlorine-substituted. This is due to the greater basicity of the starting amines with nitro-substitution when increasing the acceptor force of the substituent complicates the course of the reaction. Azomethines are characterized by absorption with a maximum at 400–410 nm, which makes them sensitive to radiation with a blue component of the spectrum. The photoelectric properties of azomethines upon irradiation were investigated by the method of measuring the surface potential with the help of a Kelvin dynamic probe. The maximum value of the electric potential of the photosensitive films free surface during irradiation with white LED at I = 60 W/m2 is about 270 mV in the case of azomethine with a nitro group in the 4,4' position and about 125 mV in the case of azomethine with chlorine as a substituent. That is, the magnitude of the electric potential of the free surface decreases approximately twice during the transition from nitro substituent to chlorine. This may be explained by the fact that the photoinduced changes in azomethine with a higher acceptor substituent flow more quickly and with greater efficiency. But at the same time, the reverse changes when turning off the light are just as fast. For chlorine substituted azomethine samples, the reverse process proceeds rather slowly, which may indicate greater stability over time of the photochemically modified form in case of chlorine substitution compared to the nitro-substituted analogue. Thus, the synthesized azomethines can be used in the development of new photovoltaic media and recording media for optical information recording.

Physicochemical Investigation of HDDP Azomethine Dye as Turn-On Fluorescent Chemosensor for High Selectivity and Sensitivity of Al3+ Ions

4-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (HDDP) was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 2-hydroxy-l-naphthaldehyde. The structure was confirmed by the IR, 1H-NMR, 13C-NMR, and EI-MS spectra and elemental analysis. Physicochemical parameters of the HDDP such as extinction coefficient, oscillator strength, transition dipole moment, Stokes shift, and fluorescence quantum yield in different solvents were studied on the basis of polarities. The interactions of various metal ions with HDDP were also studied using steady state fluorescence measurements. The emission profile reveals that it acts as off–on type fluorescent chemosensor for selective and sensitive detection of Al3+ ions. Complexation stoichiometry and mechanism of enhancement were determined from a Benesi–Hildebrand plot.

Spectroscopic Studies (Geometry Optimization, E → Z Isomerization, UV/Vis, Excited States, FT-IR, HOMO-LUMO, FMO, MEP, NBO, Polarization) and Anisotropy of Thermal and Electrical Conductivity of New Azomethine Dyes in Stretched Polymer Matrix

In the present work, first time the molecular structures of three newly synthesized azomethine dyes: (1Z)-N-benzylidene-4-((E)-1-(oxim)ethyl)benzenamine (AAFOX-1), 4-((1Z)-(4-((E)-1-(oxim)ethyl)phenylimino)methyl)phenol (AAFOX-7), (Z)-1-(4-((Z)-(4-methoxybenzylidene)amino)phenyl)ethanone oxime (AAFOX-8) have been investigated using Density Functional Theory (DFT) in dimethylformamide (DMF). The electronic spectra of azomethine dyes in a DMF solvent was carried out by TD-DFT method. After quantum-chemical calculations three new azomethine dyes for optoelectronic applications were synthesized. FT-IR spectra of the title compounds are recorded and discussed. The computed absorption spectral data of the azomethine dyes are in good agreement with the experimental data, thus allowing an assignment of the UV spectra. The molecular HOMO-LUMO, excitation energies and oscillator strengths for E and Z isomers of the dyes have also been calculated and presented. Optical Properties of the PVA-films containing new substances have been also investigated. Polarizing Efficiency (PE) of obtained PVA-film is 70–80 % at Stretching Degree (Rs) 3.5. First time anisotropy of thermal and electrical conductivity of PVA-films containing E and Z isomers of the dyes was also measured and discussed. It is new result for physical chemistry of organic dyes.

"Synthesis Of New Azomethine Dyes "

"The research includes the preparation of new azoketimines dyes by means of the coupling reaction of the schiff bases with various phenolic compounds . The prepared derivatives were diagnosed using infrared techniques, NMR proton, ultraviolet-visible radiation and thin-layer chromotography."

Design of geometry, synthesis, spectroscopic (FT-IR, UV/Vis, excited state, polarization) and anisotropy (thermal conductivity and electrical) properties of new synthesized derivatives of (E,E)-azomethines in colored stretched poly (vinyl alcohol) matrix

In the present work, the molecular structures of two new azomethine dyes: [Display omitted] have been predicted and investigated using Density Functional Theory (DFT) in dimethylformamide (DMF). The geometries of the azomethine dyes were optimized by B3LYP/6-31+G* level of theory. The electronic spectra of these azomethine dyes in a DMF solvent was carried out by using TD-B3LYP/6-31+G* method. After quantum-chemical calculations two new azomethine dyes for optoelectronic applications were synthesized. FT-IR spectra of the title compounds are recorded and discussed. The computed absorption spectral data of the azomethine dyes are in good agreement with the experimental data, thus allowing an assignment of the UV/Vis spectra. On the basis of polyvinyl alcohol (PVA) and the new synthesized azomethine dyes polarizing films for visible region of spectrum were developed. The main optical parameters of the polarizing PVA-films (Transmittance, Polarization Efficiency and Dichroic Ratio) have been measured and discussed. Anisotropy of thermal and electrical conductivity of the PVA-films have been studied and explained.

A new class of oxazolidinone- and phthalimide-based oxidation dye couplers and their effect on azomethine dye color

In the study of the effects of auxochromes on azomethine dye color, an oxazolidinone ring in the acceptor portion of the dye was useful both as a masking group for preparation of the electron-donating hydroxyethyl group, and as an electron-withdrawing auxochrome. In the case of m-aminophenol derivatives coupled with p-phenylenediamine, there was a 15 nm bathochromic shift relative to the parent azomethine of the series (PPD-MAP)3 and a 30 nm bathochromic shift relative to the azomethine formed from PPD and AHT, which contains an electron-donating group. However, unlike many electron-withdrawing groups, the oxazolidinone group does not significantly slow the rate of oxidative coupling of the MAP derivative with the primary intermediate to form the azomethine dye; it was about 70% of that for PPD with AHT, making the oxazolidinone-containing MAP a potentially effective oxidation dye intermediate. The effect on color of an oxazolidinone moiety in the acceptor portion of an azomethine formed with a 4,5-diaminopyrazole as the primary intermediate was similar in the magnitude of the bathochromic shift. Finally, including an auxochrome (phthalimide) that is electron-withdrawing in the acceptor portion of the azomethine, but which has decreased overlap with the π-system of the chromophore due to twisting out of plane caused by steric interactions, results in a significant hypsochromic shift.

Synthesis, geometry optimization, spectroscopic investigations (UV/Vis, excited states, FT-IR) and application of new azomethine dyes

In the present work, the quantum theoretical calculations of the molecular structures of the four new synthesized azomethine dyes such as:1.(E)-N-(4-butoxybenzylidene)-4-((E)-phenyldiazenyl)aniline (PAZB-6),2.(E)-N-(4-(benzyloxy)benzylidene)-4-((E))-phenyldiazenyl)aniline (PAZB-7),3.4-((E)-4-((E)-phenyldiazenyl)phenyl)imino)methyl)phenol (PAZB-8),4.(E)-N-(4-methoxybenzylidene)-4-((E))-phenyldiazenyl)aniline (PAZB-9)have been predicted using Density Functional Theory in the solvent Dimethylformamide. The geometries of the azomethine dyes were optimized by PBE1PBE/6-31+G* level of theory. The electronic spectra of the title compounds in the solvent DMF was carried out by TDPBE1PBE/6-31+G* method. FT-IR spectra of the title compounds are recorded and discussed. Frontier molecular orbitals, molecular electrostatic potential, electronic properties, natural charges and Natural Bond Orbital (NBO) analysis of the mentioned compounds were investigated and discussed by theoretical calculations. The azomethine dyes were synthesized after quantum chemical modeling for optical applications. A new study of anisotropy of thermal and electrical conductivity of the colored stretched PVA-films have been undertaken.

Quantum chemical modeling of new derivatives of (E,E)-azomethines: Synthesis, spectroscopic (FT-IR, UV/Vis, polarization) and thermophysical investigations

In the present work, the molecular structures of three new azomethine dyes: N-benzylidene-4-((E)-phenyldiazenyl)aniline (PAZB-1), 2-methoxy-4-(((4-((E)- phenyldiazenyl)phenyl)imino)methyl)phenol (PAZB-2) and 2-methoxy-5-((E)-((4-((E)- phenyldiazenyl)phenyl)imino)methyl)phenol (PAZB-8) have been predicted and investigated using Density Functional Theory (DFT) in dimethylformamide (DMF). The geometries of the azomethine dyes were optimized by PBE0/6-31 + G* level of theory. The electronic spectra of these azomethine dyes in a DMF solution was carried out by TDPBE0/6-31 + G* method. After quantum-chemical calculations three new azomethine dyes for optoelectronic applications were synthesized. FT-IR spectra of the title compounds are recorded and discussed. The computed absorption spectral data of the azomethine dyes are in good agreement with the experimental data, thus allowing an assignment of the UV/Vis spectra. On the basis of polyvinyl alcohol (PVA) and the new synthesized azomethine dyes polarizing films for Visible region of spectrum were developed. The main optical parameters of polarizing PVA-films (Transmittance, Polarization Efficiency and Dichroic Ratio) have been measured and discussed. Anisotropy of thermal conductivity of the PVA-films has been studied.

Physicochemical and Nonlinear Optical Properties of Novel Environmentally Benign Heterocyclic Azomethine Dyes: Experimental and Theoretical Studies.

Novel heterocyclic azomethine dyes were prepared by the reaction of anthracene-9-carbaldehyde with different heterocyclic amines under microwave irradiation. Structures of the azomethine dyes were confirmed by the elemental analysis, mass spectrometry and several spectroscopic techniques. We studied absorbance and fluorescence spectra of the azomethine dyes in various solvents. They are found to be good absorbers and emitters. We also report photophysical properties like, extinction coefficient, oscillator strength, stokes shift and transition dipole moment. This reflects physicochemical behaviors of synthesized dyes. In addition, their intramolecular charge transfer and nonlinear optical properties, supported by natural bond orbital technique, were also studied computationally by density functional theory. The negative nonlinear refractive index and nonlinear absorption coefficient were measured for these dyes using the closed and open aperture Z-scan technique with a continuous wave helium-neon laser. These are found to vary linearly with solution concentration.

In vitro antibacterial, radical scavenging and solvato-chromism properties of some 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino)methyl) phenols

The 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino) methyl) phenols were synthesized from the reaction of 5-((4-R-phenyl)diazenyl)-2-hydroxybenzaldehyde with aminopyridines in absolute ethanol and characterized by elemental analysis, mass, FT-IR, UV and NMR spectroscopy. The absorption maxima of synthesized compounds show bathochromic shift in various solvents. The nature of substitutions, solvent environment, hydrogen bonds, temperature, pH and dipole moment of the molecules are the key factors in deciding the solvato-chromism of azo–azomethine dyes. Antibacterial activity was studied by disk diffusion and broth microdilution methods. Diphenylpicrylhydrazyl assay was used to determine the radical scavenging properties. Compounds having electron donating groups in the aryl azo component showed significant antibacterial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli and Klebsiella pneumonia. Derivative 2-((E)-(pyridin-4-ylimino) methyl)-4-((E)-p-tolyldiazenyl) phenol (2h) with excellent antibacterial activity showed the highest scavenging effect, while the minimum antibacterial and scavenging activity was observed by 4-((E)-(4-chlorophenyl)diazenyl)-2-((E)-(pyridin-2-ylimino)methyl) phenol (2f) having electron withdrawing Cl substituent in the aryl azo component. The antibacterial and scavenging activity of synthesized derivatives are affected by the nature and position of the substituent groups and position of the nitrogen atoms in the pyridine ring. The aminopyridine-based azo–azomethine compounds have been synthesized by condensation reaction of 5-((4-R-phenyl)diazenyl)-2-hydroxybenzaldehyde with n-aminopyridine. The spectra indicated positive solvato-chromism in prepared substances which is dependent on the solvent, substitution, pH and temperature. All the synthesized azo Schiff bases except 2f showed significant antibacterial activity.

Effect of Dye Type on Montmorillonite-Supported Pr-Doped TiO2Composite Photocatalsyt

Scarcity of water in today’s world has led to scientific researches for finding smarter ways of discharging and re-using water located in the seas and lakes. That is how advanced oxidation technologies have emerged as one of the new discharging techniques to keep water sources clean. In our method we have synthesized praseodymium (Pr) doped TiO2-Montmorillonite composite photocatalyst by using acid sol-gel method. Pr, in the group of rare earth metals, is known for its ability to form Lewis bases in order to break down aldehydes, amines, etc., by decreasing the crystal size and consequently increasing the surface area. We have used the mineral form of the bentonite clay (montmorillonite) to increase the surface area of our composite photocatalyst. Two types of azo dyes which are commercially known as Basic Yellow 28 (BY 28) and Basic Blue 41 (BB 41) were used in experimants. These dyes are composed of different chemical structures: BY 28 is known as azomethine dye (–CH=N–), whereas BB 41 has one azo bond (–N=N–). The initial model dye concentrations were 100 ppm. Amount of 1.0 g/l of photocatalyst was used throughout the experiments. In order to evaluate degradation efficiency results, the dissolved organic carbon analyzer was used. We have found the optimum dark adsorption time to be under 15 minutes. By stirring under 15 minutes in the dark we have achieved efficiency of 52.50% for BY 28 and 66.74% for BB 41. On the other hand, by stirring under UV-A light irradiation for two hours we have achieved the overall degradation efficiency of 86.30% for BY 28 and 92.39% for BB 41. Our results show that higher adsorption and overall efficiencies were observed in BB 41 than in BY 28. Moreover, according to Water Pollution Control Regulations, the chemical oxygen demand limitations for textile industry are between 200–400 mg/l. To evaluate the degradation characteristics of Pr-doped TiO2-Montmorillonite composite, the change of chemical oxygen demand values with time for 100 mg/l of BY 28 and BB 41 were investigated. The obtained chemical oxygen demand values were 60.5 and 34.8 mg O2/l after 2 hours of oxidation processes for BY 28 and BB 41. As it can be seen from the results, obtained values are below the limitations.

Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

The new chromene-based azomethine dyes were synthesized via two-component coupling of 2-amino-7-hydroxy-4H-chromene with 2-hydroxy-5-(aryldiazenyl)benzaldehyde and characterized by elemental analyses, mass, NMR, IR, UV–Vis spectroscopy and X-ray diffraction analysis. Easily available and easy work-up are the key features of the present method. The pyran, chromene moiety and aromatic rings in the azomethine linkage are flattened. Intramolecular hydrogen bonding is possible between hydroxyl group and the imine nitrogen atom. All of the compounds except 2-amino-7-hydroxy-4H-chromene exhibited activity against Gram-positive bacteria Bacillus cereus, Staphylococcus aureus and Staphylococcus epidermidis. The compounds displayed weak to mild antioxidant activity compared with ascorbic acid as standard.

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.