Synthesis, characterization and applications of some azo dyes derived from various aromatic amines

Article abstract of DOI:10.14233/ajchem.2018.21414

In this work, we report the synthesis of metal free dyes and their fastness properties. A series of monoazo dyes obtained by diazotization of various aromatic primary amines and coupling with different components. One coloured Schiff base derived from triethylene tetramine and N,N-dimethylbenzaldehyde was also synthesized. These coloured compounds were characterized by FTIR, UV-visible, ¹H, ¹³C NMR and ESI mass spectroscopic methods. The dyeing performance of all the compounds were evaluated on cotton fabric. They were applied on bleached cotton fabric and their dyeing and fastness properties were assessed. The absorption spectra of the dyes are discussed with regard to their structure. The structure of coloured dyes and Schiff base are proposed based on various spectroscopic data. The newly synthesized group of monoazo dyes gives shades ranging from yellow to reddish orange with good light fastness and excellent wash fastness.

Full text of DOI:10.14233/ajchem.2018.21414

Asian Journal of Chemistry; Vol. 30, No. 9 (2018), 2049-2053
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2018.21414
Synthesis, Characterization and Applications of Some
Azo Dyes Derived from Various Aromatic Amines
*
V.G. VIDYA and V. SADASIVAN
Department of Chemistry, University College, M.G. Road, Thiruvananthapuram-695 034, India
*Corresponding author: E-mail: vg_vidya@yahoo.co.in
Received: 28 April 2018;
Accepted: 7 June 2018;
Published online: 31 July 2018;
AJC-19019
In this work, we report the synthesis of metal free dyes and their fastness properties. A series of monoazo dyes obtained by diazotization
of various aromatic primary amines and coupling with different components. One coloured Schiff base derived from triethylene tetramine
and N,N-dimethylbenzaldehyde was also synthesized. These coloured compounds were characterized by FTIR, UV-visible, 1H, 13C NMR
and ESI mass spectroscopic methods. The dyeing performance of all the compounds were evaluated on cotton fabric. They were applied
on bleached cotton fabric and their dyeing and fastness properties were assessed. The absorption spectra of the dyes are discussed with
regard to their structure. The structure of coloured dyes and Schiff base are proposed based on various spectroscopic data. The newly
synthesized group of monoazo dyes gives shades ranging from yellow to reddish orange with good light fastness and excellent wash
fastness.
Keywords: Azo dyes, Cotton fabric, Fastness properties.
are used as intermediates in dye stuff industry [15-21]. Focussed
attention has been given to heterocyclic derivatives of azo dyes
due to their diverse biological activities as antitumor, anti-
inflammatory, antibacterial and antifungal agents [22-24]. In
this endeavour, a series of heterocyclic monoazodyes with good
dyeing and fastness properties have been assessed.
INTRODUCTION
Azo dyes are the most important class of dyes accounting
for more than 50 % of all commercial dyes or colourants. They
have found many applications in various fields of science and
technology [1,2]. The importance behind this study is to synth-
esize azo dyes containing heterocyclic rings due to their superior
properties. The introduction of heterocyclic ring as coupling
components have made possible the synthesis of good colou-
rants with chromophoric strength and brilliant colours. Such
dyes have high level dyeing properties and excellent fastness
properties [3]. The usability of heterocyclic azo dye lies in the
field of textiles, papers, leather, additives, food stuff, cosmetics,
holographic data storage materials, xerography laser materials,
laser printing, materials for organic solar cells and chemo-
sensors, etc. [4-9].
Heterocyclic azodyes are found to be useful in second harm-
onic nonlinear optical material and optical switching devices
[10-12]. The strong bathochromic effect of heterocyclic system
is due to its diene character [13]. Towns [14] has reported the
developments in azo dyes derived from heterocyclic azo compo-
nents.A number of heterocyclic azo dyes and their derivatives
EXPERIMENTAL
All the reagents and solvents for syntheses and analyses
were of Merck products and used as supplied. FTIR spectra
were recorded using KBr discs on a Perkin-Elmer spectrum 65
spectrometer. Elemental analyses were performed on a Vario
EL-III CHN elemental analyzer. Electronic absorption spectral
measurements of the dyes in methanol were conducted using
Perkin-Elmer Lambda 25 UV-Vis spectrophotometer. 1H and
13C NMR spectra were recorded on a 400MHz FTNMR instru-
ment. Mass spectra of the dyes and Schiff base obtained with
ESI mass spectra. Fastness to light, sublimation and perspiration
were assessed in accordance with BS: 1006-1978. The rubbing
fastness test was carried out with a Crockmeter,Atlas in accor-
dance with AATCC-1961 and the wash fastness test in accor-
dance with IS:765-1979. The details of the method of colour
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2050 Vidya et al.
Asian J. Chem.
fastness test were described in literature [25]. The dyeing of
cotton fabrics were carried out according to the literature [26].
Synthesis of dyes: All the dyes were prepared by the
standard procedure of diazotization of amines [27,28] followed
by coupling with corresponding compounds.
Synthesis of 5-(3-hydroxy-pyridin-2-ylazo)-1H-primi-
dine-2,4-dione (dye III): A solution of 2-amino-3-hydroxy-
pyridine (0.01 mol) was prepared in the minimum amount of
HCl (2 mL). A cold solution of NaNO2 below 5 ºC was then
added to amine solution dropwise with continuous stirring. A
solution of 0.01 mol of uracil was prepared by dissolving in
NaOH solution then cooled to 0 ºC. The cold diazonium salt
solution was added to uracil solution in NaOH kept at 0 ºC
(Scheme-III). The pink coloured solid dye was filtered off and
recrystallized from ethanol. The purity of product was checked
by TLC. Yield: 81 %. IR (KBr, νmax, cm-1): 1438 (N=N), 1669
(C=O). UV (λmax, MeOH): 480 nm. 1H NMR (DMSO-d6) ppm:
δ 7.60-7.82 (3H), 11.01 (2H), 5.46 (1H), 9.37 (1H); 13C NMR
(DMSO-d6) ppm: δ 100.01, 124.36, 125.89, 138.75, 141.36,
142.75, 152.91, 155.36 (C-OH), 164.89 (C=O). Elemental anal-
ysis of C9H8N5O3 calcd. (found) %: C, 46.15 (46.17); H, 3.40
(3.38); N, 29.91 (29.92); HRMS Calcd. (found): [M+H]+ 235.03
([M+H]+ 235.01.
Synthesis of 5-(2,3-dimethyl-1-phenyl-3- pyrazolin-5-
one-4-ylazo)-1H-pyrimidine-2,4-dione (dye I): A solution
of 4-aminoantipyrine (0.01 mol) was prepared in least amount
of HCl (2 mL).A cold solution of NaNO2 below 5 ºC was then
added to amine solution dropwise with continuous stirring. A
solution of 0.01 mol of uracil was prepared by dissolving it in
NaOH solution and then cooled to 0 ºC. The cold diazonium
salt solution was added to uracil solution in NaOH kept at 0 ºC
(Scheme-I). The yellow coloured solid dye was filtered off and
recrystallized from ethanol. The purity of product was checked
by TLC. Yield: 80 %. IR (KBr, νmax, cm-1): 1455 (N=N), 1677
(C=O). UV (λmax, MeOH): 326 nm. 1H NMR (DMSO-d6) ppm:
δ 2.23 (3H) S, 3.14 (3H), 7.60- 7.82 (5H), 11.01 (2H), 5.46
ppm (1H) s; 13C NMR (DMSO-d6) ppm: δ12.43 (C-CH3), 36.13
(N-CH3), 96.48, 123.53 (C-N), 123.15, 125.92, 126.71, 128.43,
128.99, 129.28 (C), 135.34 (C=C), 142.08, 151.42, 166.14
(C=O), 164.26 (C=C). Elemental analysis of C15H14N6O3 calcd.
(found) %: C, 55.19 (55.21); H, 4.30 (4.28); N, 25.75 (25.74);
HRMS Calcd. (found): [M+H]+ 327.568 ([M+H]+ 327.569) [29].
O
O
H
N
O
N
N
N
-
NH
+
Cl
N
N
+
NH
N
N
O
H
Dye III
OH
OH
Scheme-III
O
CH
CH
3
3
O
H
N
H C
3
O
H C
3
Synthesis of 2-(2-hydroxy-naphthalen-1-ylazo)pyridin-3-
ol (dye IV): A solution of 2-amino-3-hydroxypyridine (0.01
mol) was prepared in the minimum amount of HCl (2 mL). A
cold solution of NaNO2 below 5 ºC was then added to amine
solution dropwise with continuous stirring. A solution of 0.01
mol of β-naphthol was prepared by dissolving in NaOH solution
then cooled to 0 ºC. The cold diazonium salt solution was added
to β-naphthol solution in NaOH kept at 0 ºC (Scheme-IV). The
grey coloured solid dye was filtered off and recrystallized from
ethanol. The purity of product was checked by TLC. Yield: 72
+
N
N
N
N
NH
-
N
Cl
N
+
NH
N
N
N
H
O
C
H
5
6
O
C H
6
5
Dye I
O
Scheme-I
Synthesis of 6-amino-5-(1,5-dimethyl-3-oxo-2-phenyl-
2,3-dihydro-1H-pyrazol-4-ylazo)-1H-pyrimidine-2,4-dione
(dye II):A solution of 4-aminoantipyrine (0.01 mol) was prepared
in least amount of HCl (2 mL).A cold solution of NaNO2 below
5 ºC was then added to amine solution dropwise with contin-
uous stirring.A solution of 0.01 mol of 6-aminouracil was prep-
ared by dissolving in NaOH solution then cooled to 0 ºC. The
cold diazonium salt solution was added to 6-aminouracil solution
in NaOH kept at 0 ºC (Scheme-II). The red coloured solid dye
was filtered off and recrystallized from ethanol. The purity of
product was checked by TLC. Yield: 78 %. IR (KBr, νmax, cm-1):
1429 (N=N), 1658 (C=O). UV (λmax, MeOH): 508 nm. 1H NMR
(DMSO-d6) ppm: δ 2.24 (3H), 3.24 (3H), 7.60-7.82 (5H), 11.02
(2H), 5.46 (1H), 8.34 (2H); 13C NMR (DMSO-d6) ppm: δ 11.23
(C-CH3), 37.12 (N-CH3), 97.41, 124.18 (C-N), 120.01, 124.21,
127.30, 128.14, 130.17, 131.99 (C), 142.13, 152.61, 160.14
(C=O), 167.15 (C=C), 178.01 (C-NH2). Elemental analysis of
C15H16N7O3 calcd. (found) %: C, 52.63 (52.64); H, 4.67 (4.65);
N, 28.65 (28.63); HRMS Calcd. (found): [M+H]+ 343.23 ([M+H]+
343.23).
%. IR (KBr, νmax, cm-1): 1468 (N=N), 3392 (O-H). UV (λmax
,
MeOH): 265 nm.1H NMR (DMSO-d6) ppm: δ 7.70-7.90 (9
H), 9.40 (1H), 10.40 (1H); 13C NMR (DMSO-d6) ppm: δ 99.98,
109.51, 116.16, 117.74, 120.13, 123.63, 125.12, 126.37, 126.53,
127.77, 128.98, 129.85, 134.61, 153.35, 159.12 (C-OH). Elem-
ental analysis of C15H11N3O2 calcd. (found) %: C, 67.66 (67.64);
H, 4.51 (4.50); N, 15.69 (15.70); HRMS Calcd. (found): [M+H]+
267.13 ([M+H]+ 267.11) [30].
HO
HO
N
N
+
N
N
-
N Cl
+
N
OH
Dye IV
OH
Scheme-IV
O
CH
CH
3
3
O
H
N
Synthesis of 4-(2,4-dihydroxy-phenylazo)-3-hydroxy-
naphthalene-1-sulfonic acid (dyeV):A solution of 1-amino-
2-naphthol-4-sulphonic acid (0.01 mol) was prepared in least
amount of HCl (2 mL). A cold solution of NaNO2 below 5 ºC
was then added to amine solution dropwise with continuous
stirring. A solution of 0.01 mol of resorcinol was prepared by
H C
3
O
H C
3
N
N
N
NH
+
N
N
-
N
Cl
+
NH
N
N
N
H
O
C H
6
H N
2
5
O
C H
6
5
H N
2
O
Dye II
Scheme-II

Vol. 30, No. 9 (2018)
Synthesis and Applications of Some Dyes Derived from Various Aromatic Amines 2051
dissolving in NaOH solution then cooled to 0 ºC. The cold diazo-
nium salt solution was added to resorcinol solution in NaOH
kept at 0 ºC (Scheme-V). The brown coloured solid dye was
filtered off and recrystallized from ethanol. The purity of product
was checked by TLC. Yield: 83 %. IR (KBr, νmax, cm-1): 1459
(N=N), 3436(O-H). UV(λmax, MeOH): 360 nm. 1HNMR(DMSO-
d6) ppm: δ 6.10-7.70 ppm (8H), 2.50 (1H, s), 8.70 (1H, s), 9.30
(1H, s), 11.1 (1H, s); 13C NMR (DMSO-d6) ppm: δ108.12, 109.34,
117.43, 124.01, 124.35, 126.12, 126.51, 126.99, 127.32, 129.30,
133.05, 136.73, 145.08, 145.98, 152.28,152.31 (C-OH). Elem-
ental analysis of C16H12N2O6S calcd. (found) %: C, 53.30 (53.32);
H, 3.32 (3.30); N, 7.71 (7.70); S, 8.88 (8.87). HRMS Calcd.
(found): [M+H]+ 361.31 ([M+H]+ 361.30) [31,32].
[33,34]. Furthermore, the dyes gave excellent uniformity
of colouration on cotton fabric without the use of retarding
agent.
Fastness to washings at 50 ºC and to perspiration shows
excellent behaviour. Most of the dyes have a fair rubbing fastness
3, which can be attributed to inadequate diffusion of the dye
molecules into the fabric. Most of the dyes exhibit good sublim-
ation and light fastness.
Determination of dyeing and fastness
Dyeing: The fabric was dyed with 2 % dye (calculated
on the weight of fabric), 1 % NaCl (as dispersing agent), kept
at a liquor ratio of 20:1. The process was started at 60 ºC and
the temperature was then raised to 130 ºC over 30 min and main-
tained for 1 h. After cooling, the fabric was taken out and
treated with a solution of 2 % sodium bisulphite, 2 % NaOH
and 0.1 % NaCl at 70 ºC for 30 min. Finally, the fabric was
rinsed and dried at 60 ºC [35].
Evaluation of fastness properties of a dye is done by meas-
uring washing, light, rubbing and perspiration fastness values
using wash wheel, xenoster, crock meter and prespirometer,
respectively in terms of standard methods and these properties
were measured using grey scale [36].
+
N
-
HO
Cl
N
OH
OH
N
+
OH
N
HO3S
SO3H
HO
OH
Dye V
Scheme-V
Synthesis of N-(4-dimethylamino-benzylidene)-N-(2-
{2-[(4-dimethylamino-benzylidine)amino]ethylamino}-
ethyl)-ethane-1,2-diamine) (dye VI): A methanolic solution
of triethylenetetramine (0.01 mol) and N,N-dimethylbenzal-
dehyde (0.01mol) was heated under reflux on a water bath for
7 h. The solution was kept at room temperature for 24 h. Brown
crystals separated was filtered and recrystallized from methanol
(Scheme-VI). Yield: 85 %. IR (KBr, νmax, cm-1): 1620 (C=N),
3021 (N-H). UV (λmax, MeOH): 394 nm.Elemental analysis
of C24H36N6 calcd. (found) %: C, 70.58 (70.59); H, 8.82 (8.80);
N, 20.58 (20.57). HRMS Calcd. (found): [M+H]+ 409.03
([M+H]+ 409.01).
Colour fastness tests
Fastness to washing: A specimen of dyed cotton fabric
was stitched between two pieces of undyed cotton fabric all
of equal length and then washed at 50 ºC for 30 min. After
soaping treatment, the specimen is removed, rinsed twice in
cold water and then in cold running tap water. Squeezed and
dried in air at a temperature not exceeding 60 ºC. The staining
on the undyed adjacent fabric was assessed according to the
gray scale [37].
Fastness to perspiration: The samples were prepared by
stitching a piece of dyed cotton fabric between two pieces of
undyed cotton fabric, all of equal length and then immersed
in the acidic (pH 3.5) or alkaline solution(pH 8.0) for 30 min.
The staining on undyed adjacent fabric was assessed according
to gray scale.
Fastness to rubbing: The dyed cotton fabric was placed
on the base of crockmeter, so that it rested flatly on the abrasive
cloth with its long dimension in the direction of rubbing. A
square of white testing cloth was allowed to slide on the tested
fabric back and froth 20 times by making 10 complete turns
of the crank. For the wet rubbing test, the testing squares were
thoroughly immersed in distilled water. The rest of the procedure
was the same as in the dry test. The staining on the white testing
cloth was assessed according to the gray scale [38].
Fastness to sublimation: Sublimation fastness was measured
with an iron tester.The samples were prepared by stitching a
piece of dyed cotton fabric between two pieces of undyed
cotton, all of equal length and then treated at 180 and 210 ºC
after every 1 min. Any staining on undyed adjacent fabric or
change in tone was assessed according to gray scale.
Fastness to light: Light fastness was determined by exposing
the dyed polyester on a Xenotest 150 (original Hanau, Chamber
temperature: 25-30 ºC; black panel temperature: 60 ºC; relative
humidity: 50-60 %; dark glass UV filter system) for 40 h. The
change in colour was assessed according to gray scale [39].
HN
N
NH
N
CHO
HN
NH
NH
2
+
H N
2
2
NMe
2
Dye VI
N(Me)
Me N
2
2
Scheme-VI
Dyeing of cotton fabric and dyeing properties: Efforts
have been made to prepare disperse dyes derived from hetraryl
compounds. Useful dyes in this respect are derived from 4-amino-
antipyrine, uracil, 6-aminouracil, 2-amino-3-hydroxy-pyridine,
1-amino-2-naphthol-4-sulphonic acid and triethylenetetramine.
The new dyes are studied for their dyeing properties and perfor-
mance. The new dyes were applied on cotton fabric at 2 %
shade by high temperature technique and gave generally deep
and bright intense hues, ranging from yellow to red.
Assessment of colour fastness: Satisfactory colour yields
compared with commercial dyes applied under similar conditions
were obtained at 2 % depth of dye liquors were also achieved

2052 Vidya et al.
Asian J. Chem.
TABLE-1
FASTNESS PROPERTIES OF THE DYES ON COTTON FABRIC
Washing
Staining on
Sublimation fastness
Staining at
Perspiration
Rubbing
Dye
I
II
III
IV
V
1
1
1
1
1
1
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4-5
4
4-5
4
4-5
4-5
4-5
4
4-5
4
3
2-3
2-3
2-3
2-3
2-3
2-3
4
4
4
4-5
4-5
4-5
4
3-4
3-4
4
4-5
4-5
4
1-3
5
1-3
5
5
3
3
3
3
3
3
4-5
4-5
4-5
4
VI
4-5
crystalline and hydrophobic in nature it inhibit the diffusion
of dye out of the fiber, thus better ratings are obtained. The
remarkable degree of brightness of the fabric after washing is
indicative of good penetration and the excellent affinity of the
dye to different fabrics [45].
RESULTS AND DISCUSSION
The above mentioned azo dyes provide wide range of colour
with good levelness, brightness and depth on dyeing cotton
fabrics. The nature and position of substituents present on the
diazotized compound and coupling components has great influ-
ence on shade of dyeing [40,41]. The heteroatoms present in
the ligand structure also results in the bathochromicity and leads
to the brightness of shades. From the results (Table-1), it is
revealed that dyes have fair to good fastness properties to light,
washing, perspiration, rubbing and sublimation. The fastness
properties of dyeing are correlated with the structure of the
dye and substrate to which it is applied [42].
Dye I toV contains azo group andVI contains azomethine
group as chromophore. Dye I and II contains carbonyl group,
dye II and III contains amino group, IV andV contains hydroxyl
group,V contains sulfonic acid group andVI contains NH group
as well as N(Me)2 groups. Such groups often attatched to chromo-
phores modify colours to molecules. In cotton fabrics, these
dyes gets attached to fabric by hydrogen bonding. Dye VI is
long enough and straight so that they can line up with cellulose
fibers and form several hydrogen bonds.
An important property of textiles is their light fastness
which is affected by several factors such as physico-chemical
characteristics of fibers, chemical structure of dyes the wave-
length distribution of impinging radiation and several other
environmental conditions [43]. In this present case, the reported
dyes exhibit wide range of fastness from 1 to 5 on cotton fabrics
and are significantly affected by nature of substituents. The light
fastness depends on degree of aggregation of dye within the
fabric, nature of fabric in which it is dispersed, characteristics
of incident radiation, molecular structure, molecular size and
substantivity [41]. In this work, the best light fastness was
obtained for dye II, IV and V. This agrees with the notion that
azo compounds appended with electron withdrawing substituents
on the diazo components are less prone to photofading [44].
The presence of electron withdrawing group such as sulfonic
acid adjacent to diazotizable amino group has a bathochromic
influence on the shades of these dyes on fabric and is useful
for better dispersability and dyeability.
The best results are shown for perspiration fastness as the
dye molecules penetrates deeper into fabric. The rubbing fast-
ness depends on the presence of loose dye particles on the surface
of fabric. It depends on the substantivity of dye for the fabric,
which in turn depends on molecular size, geometry and polarity
of molecule [46]. Rubbing fastness property is moderate in
dry and fair to moderate in wet condition. Sublimation fastness
are good to excellent at 180 ºC and moderate to excellent at
210 ºC as dye molecules are less stable at higher temperature.
Dye V having sulfonic acid group as well as three hydroxyl
group shows better result to fastness properties among the
discussed dyes in this work. The molecular size, geometry
and molecular mass also enhances the discussed properties.
Conclusion
Azo dyes derived from various heterocyclic amines have
been synthesized and characterized. These dyes gave yellow
hues with good levelness, brightness and depth on fabrics. The
variation in the hues of the dyed fabrics results from both the
nature and position of the substituent present on the azo
coupling ring.All the fastness properties are inter-related since
they depend on rate of diffusion of dye into fabric. This rate is
a function of geometry of dye molecule, small molecular size,
the intrinsic property of heterocyclic ring, the electron with-
drawing character of an appropriately substituted groups and
hydrophobic nature of heterocyclic ring which is useful for
better dispersability, dyeability and intrinsic conjugation in
structure leading to fair to excellent properties. All the dyes
have higher rating. The washing fastness of dyes are very good
compared with commercial dyes. From the results, it can be
conclued that dye IV and V have good assessment values for
fastness properties that can be successfully used for dyeing textile
fabrics,mainly on account of the facility and low-cost of the
dyes synthesis, ease of application and overall versatility of
their use.
The solubility and rate of movement of dye out of the fabric
during washing depends on the size of dye molecules, the type
of mechanical linkage between dye and fiber, and the type of
charge on dye, which in turn depends on the electron donating
or electron attracting character of substituents. If the fabric is
ACKNOWLEDGEMENTS
The authors are thankful to Department of Chemistry, Univ-
ersity College, Trivandrum, India for instrumental facilities
under FIST DST, SITRA Coimbatore, India and SAIF Cochin

Vol. 30, No. 9 (2018)
Synthesis and Applications of Some Dyes Derived from Various Aromatic Amines 2053
20. D.R. Patel and K.C. Patel, Serb. Chem. Soc., 76, 177 (2011);
for analytical facilities. One of the authors (VGV) is thankful
to UGC for the Faculty Development Programme support.
https://doi.org/10.2298/JSC090225021P.
21. M.M. Parekh and K.C. Maheria, J. Sci. Ind. Res., 70, 525 (2010).
22. G.B. Bagihalli, P.G.Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem.,
43, 2639 (2008);
CONFLICT OF INTEREST
https://doi.org/10.1016/j.ejmech.2008.02.013.
23. E. Rodríguez-Fernández, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte
and J.J. Criado, J. Inorg. Biochem., 99, 1558 (2005);
https://doi.org/10.1016/j.jinorgbio.2005.05.004.
24. Z.H. Chohan, S.H. Sumrra, M.H.Youssoufi and T.B. Hadda, Eur. J. Med.
Chem., 45, 2739 (2010);
https://doi.org/10.1016/j.ejmech.2010.02.053.
25. J. Park and D.J. Smith, J. Soc. Dyers Colourists, 90, 431 (1974);
https://doi.org/10.1111/j.1478-4408.1974.tb03179.x.
26. C.L. Bird, J. Soc. Dyers Colourists, 70, 68 (1954);
https://doi.org/10.1111/j.1478-4408.1954.tb02017.x.
27. V. Sadasivan and M. Alaudeen, Indian J. Chem., 46A, 1959 (2007).
28. G. Kaupp, J. Schmeyers and J. Boy, J. Prakt. Chem., 342, 269 (2000);
https://doi.org/10.1002/(SICI)1521-3897(200003)342:3<269::AID-
PRAC269>3.0.CO;2-0.
The authors declare that there is no conflict of interests
regarding the publication of this article.
REFERENCES
1. J. Tao, G. Mao and L. Daehne, J. Am. Chem. Soc., 121, 3475 (1999);
https://doi.org/10.1021/ja983842v.
2. A. Navarro and F. Sanz, Dyes Pigments, 40, 131 (1999);
https://doi.org/10.1016/S0143-7208(98)00048-5.
3. K.L. Georgiadou and E.G. Tsatsaroni, Dyes Pigments, 50, 93 (2001);
https://doi.org/10.1016/S0143-7208(01)00034-1.
4. J.A. Mikroyannidis, D.V. Tsagkournos, S. Sharma, A. Kumar,Y.K. Vijay
and G.D. Sharma, Sol. Energy Mater. Sol. Cells, 94, 2318 (2010);
https://doi.org/10.1016/j.solmat.2010.08.001.
5. H. Dincalp, F. Toker, I. Durucasu, N. Avcibasi and S. Icli, Dyes
Pigments, 75, 11 (2007);
https://doi.org/10.1016/j.dyepig.2006.05.015.
6. D. Zhang, M. Zhang, Z. Liu, M.Yu, F. Li, T. Yi and C. Huang, Tetrahe-
dron Lett., 47, 7093 (2006);
29. V.G. Vidya, S.S. Meena, P. Bhatt, V. Sadasivan and S. Mini, AIP Conf.
Proc., 1536, 1009 (2013);
https://doi.org/10.1063/1.4810574.
30. S. Mini, S.S. Meena, P. Bhatt, V. Sadasivan and V.G. Vidya, AIP Conf.
Proc., 1620, 1011 (2013);
https://doi.org/10.1016/j.tetlet.2006.07.080.
https://doi.org/10.1063/1.4810575.
7. B.A. Trofimov, E.Y. Schmidt, A.I. Mikhaleva, A.M. Vasil’tsov, A.B.
Zaitsev, N.S. Smolyanina, E.Y. Senotrusova,A.V.Afonin, I.A. Ushakov,
K.B. Petrushenko, O.N. Kazheva, O.A. Dyachenko, V.V. Smirnov, A.F.
Schmidt, M.V. Markova and L.V. Morozova, Eur. J. Org. Chem., 4021
(2006);
31. V.G. Vidya, V. Sadasivan, S.S. Meena and P. Bhatt, AIP Conf. Proc.,
1620, 622 (2014);
https://doi.org/10.1063/1.4898308.
32. S. Mini, V. Sadasivan, S.S. Meena and P. Bhatt, AIP Conf. Proc., 1536,
322 (2014);
https://doi.org/10.1002/ejoc.200600357.
https://doi.org/10.1063/1.4898259.
8. M. Bhaskar,A. Gnanamani, R.J. Ganeshjeevan, R. Chandrasekar, S. Sadulla
and G. Radhakrishnan, J. Chromatogr. A, 1018, 117 (2003);
https://doi.org/10.1016/j.chroma.2003.08.024.
9. M. Dakiky and I. Nemcova, Dyes Pigments, 44, 181 (2000);
https://doi.org/10.1016/S0143-7208(99)00086-8.
10. M.M. Russew and S. Hecht, Adv. Mater., 22, 3348 (2010);
https://doi.org/10.1002/adma.200904102.
11. E. Kleinpeter, U. Bolke and J. Kreicberga, Tetrahedron, 66, 4503 (2010);
https://doi.org/10.1016/j.tet.2010.04.067.
12. X. Li, Y. Wu, D. Gu and F. Gan, Dyes Pigments, 86, 182 (2010);
https://doi.org/10.1016/j.dyepig.2010.01.002.
13. J. Griffiths, Colour and Constitution of Organic Molecules; Academic
Press, London, p. 186 (1976).
33. M.A. Metwally, Dyes Pigments, 60, 249 (2004);
https://doi.org/10.1016/S0143-7208(03)00153-0.
34. H.R. Maradiya, J. Saudi Chem. Soc., 14, 77 (2010);
https://doi.org/10.1016/j.jscs.2009.12.012.
35. V.A. Shenai, Chemistry of Dyes and Principles of Dyeing, Sevak
Publication, Bombay, India (1973).
36. Anon, Standard Methods for Determination of Colour Fastness of
Textiles and Leather, Society of Dyers and Colourists Publication
Bradford, England (1990).
37. AATCC Test method, p. (1961).
38. Indian Standard ISO, p. 765 (1979).
39. Standard Rest Method BS 1006-1978; UK, ISO 105-1995.
40. B.C. Dixit, H.M. Patel and D.J. Desai, J. Serb. Chem. Soc., 72, 119
(2007);
14. A.D. Towns, Dyes Pigments, 42, 3 (1999);
https://doi.org/10.1016/S0143-7208(99)00005-4.
https://doi.org/10.2298/JSC0702119D.
15. V. Arun, P.P. Robinson, S. Manju, P. Leeju, G. Varsha, V.K.K.M. Digna
and K.K.M. Yusuff, Dyes Pigments, 82, 268 (2009);
https://doi.org/10.1016/j.dyepig.2009.01.010.
16. H.S. Bhatti and S. Seshadri, Color. Technol., 120, 151 (2004);
https://doi.org/10.1111/j.1478-4408.2004.tb00221.x.
17. V.H. Patel, M.P. Patel and R.G. Patel, Dyes Pigments, 52, 191 (2002);
https://doi.org/10.1016/S0143-7208(01)00068-7.
18. D.R. Patel and K.C. Patel, Dyes Pigments, 90, 1 (2011);
https://doi.org/10.1016/j.dyepig.2010.10.013.
19. D.R. Patel and K.C. Patel, Arab. J. Chem., 76, 1 (2011).
41. H.R. Maradiya and V.S. Patel, Bull. Chem. Technol., 21, 57 (2002).
42. G. Hallas and A.D. Towns, Dyes Pigments, 35, 45 (1997);
https://doi.org/10.1016/S0143-7208(96)00088-5.
43. M.R. Massafra, E. Selli, S. Salsa and B. Marcandalli, Dyes Pigments,
40, 171 (1999);
https://doi.org/10.1016/S0143-7208(98)00045-X.
44. P.F. Gordon and P. Gregory, Organic Chemistry in Colour, Springer-Verlag,
New York (1983).
45. H.R. Maradiya, Turk. J. Chem., 25, 441 (2001).