Assessment of dyeing properties of novel bisazo-bisazomethine disperse dyes on polyester fabric

Article abstract of DOI:10.1155/2011/806137

Novel bisazo-bisazomethine disperse dyes were prepared by the coupling of diazotized solutions of various aromatic amines with 2,2'-sulfonylbis [4,1-phenylene nitrilomethylylidene] diphenol (SB). Above Schiff base was prepared by the condensation of 2-hyd

Full text of DOI:10.1155/2011/806137

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2011, 8(3), 1218-1225
http://www.e-journals.net
Assessment of Dyeing Properties of Novel Bisazo-
Bisazomethine Disperse Dyes on Polyester Fabric
B. C. DIXIT* and D. M. PATEL
Department of Chemistry
V. P. & R. P. T. P. Science College, Vallabh Vidyanagar-388120
Dist. Anand, State-Gujarat, India
dixits20002003@yahoo.co.in
Received 21 September 2010; Revised 19 December 2010; Accepted 8 January 2011
Abstract: Novel bisazo-bisazomethine disperse dyes were prepared by the
coupling of diazotized solutions of various aromatic amines with 2,2'-{sulfonylbis
[4,1-phenylene nitrilomethylylidene]} diphenol (SB). Above Schiff base was
prepared by the condensation of 2-hydroxybenzaldehyde with 4,4’-sulphonyl-
dianiline (Dapson). The resultant dyes were characterized by elemental
analysis, IR and 1H NMR spectral studies. The UV Visible absorption spectral
data were investigated in dimethylformamide (DMF) and are discussed in
terms of structural property relationship. Their dyeing performance as disperse
dyes has been assessed on polyester fabrics. The results show that a better hue
was obtained on polyester fabrics and have mild to moderate fastness
properties.
Keywords: Dapson, Schiff base, Bisazo-bisazomethine disperse dyes, Polyester fabrics,
Chromophoric group
Introduction
Since long back azo disperse dyes, azo-vat and azo-acid dyes etc. were marketed as a
commercial dyes. All have phenolic moiety bearing hydroxy group(s) as an auxochrome1-5.
Much attention has also been given towards bisazo and polyazo dyes as dying materials6-11
.
In addition to that there are several reports regarding bisazomethine dyes in which azoimine
group formed by Schiff’s reaction of aldehyde with aromatic diamine12-14. However, there
are no any reports regarding bisazo-bisazomethine disperse dyes in which both bisazo and
bisazomethine chromophoric groups lying in a single molecular framework. Hence, the
present communication comprises synthesis; characterization and dyeing performance of
bisazo-bisazomethine disperse dyes on polyester fabric.

1219
B. C. DIXIT et al.
Experimental
All the chemicals used were of analytical grade and were further purified as and when
required. Dapson (4,4’-sulfonyldianiline), salicylaldehyde (2-hydroxybenzaldehyde), different
aromatic primary amines, sodium hydroxide, sodium nitrite, hydrochloric acid were
purchased from local market. The organic solvents used were purified by standard
methods15. The aromatic amines used for diazotization are listed in Scheme 1. Polyester
fabrics were gifted by Color Tax (Pvt) Ltd, Surat. Melting points were determined by open
capillary method and were found uncorrected. The visible absorption spectra were measured
on a Carl Zeiss UV/VIS specord spectrometer and elemental analysis was carried out on
Perkin Elmer CHNS/O Analyzer 2400 Series II. Infrared spectra were recorded in KBr
1
pellets on a Perkin-Elmer spectrum GX FT-IR model. H NMR spectra were recorded on
Hitachi R-1500 in DMSO-D6 solvent and TLC (Thin layer chromatography) was run on a
aluminium sheets precoated with silica gel 60 F245 , (Merck, Germany) using ethyl acetate:
n-hexane (1:1) solvent system. Colour spot was visualized by UV chamber. Intra dyeing
machine was used for dying purpose.
Synthesis of 2,2'-{sulfonylbis[4,1-phenylenenitrilomethylylidene]}diphenol (SB)
A solution of dapson (4.96 g, 0.02 mol) in absolute alcohol (50 mL) was prepared. To the
above solution an ethanolic solution (100 mL) of salicylaldehyde (4.88 g, 0.04 mol) was
added slowly under stirring to produce a yellow crystalline solid product upon cooling at
room temperature. The product thus obtained was filtered, washed with ethanol and dried in
0
vacuum desiccator. Yield: 79.65% m.p. 221-224 C (uncorrected). The synthetic route is
shown in Scheme 1.
Synthesis of the bisazo-bisazomethine disperse dyes
Diazotization procedure
Bisazo-bisazomethine disperse dyes were prepared in a two steps viz. diazotization of
aromatic amines followed by their coupling with Schiff base. Diazotization was carried out
by the reported method16-18. Accordingly, aniline and other substituted amines such as
p-toludine, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 3-chloroaniline, 4-chloroanilne,
4-bromoaniline, 3-aminophenol and 4-aminophenol were diazotized by following the given
procedure:
A solution of 1.86 g aniline (0.02 mole) in 25 mL 2 N HCI (0.05 mole) was cooled in an
ice bath and was stirred well. After reaching to 0-5 0C temperature a chilled 10 mL solution
of 1.38 g sodium nitrite (0.02 mole) was added drop wise so that the temperature should not
exceeds 2-3 0C during a time of half an hour. The mixture was stirred well further for about
10 min. after completion of diazotization reaction. The test conducted for this purpose is a
blue colouration with Congo red paper and a weak blue colour with starch iodide paper. If
diazotization is not completed than add more nitrite solution drop wise until a positive test
for diazotization is obtained. The diazotized amine solution thus prepared was used
immediately for coupling reaction. Almost all amines were diazotized by following the
similar procedure.
Coupling of above mentioned diazotized aromatic amines with Schiff base was carried
out by following the reported method16-18. Accordingly, 4.56 g Schiff base (0.01 mole) was
dissolved in aqueous solution of 50 mL sodium hydroxide (0.01 mole). The clear solution
was cooled in ice bath and diazonium salt solution of amine (0.02 mole) was added drop by
drop over a period of 15 minutes accompanied by vigorous stirring. The pH of solution

Assessment of Dyeing properties of Novel Bisazo-Bisazomethine
1220
mixture was maintained in the range of 8 to 9 by simultaneous addition of 10% w/v sodium
carbonate solution. Stirring was continued for 2 h, allowing the temperature to rise to
ambient. Then 2 M solution of acetic acid was added until the pH of solution becomes 7.
The dye precipitated out was then filtered off, washed with distilled water until it becomes
salts free and was dried at room temperature. The dyes were recrystallised by appropriate
organic solvent and were designated as dyes D1-D10.
Dyeing and fastness properties of fabrics
All the dyes D1 to D10 were applied on polyester fabrics in 2% shade by using the reported
procedure19. The fastness to light, sublimation and perspiration of the dye pattern was
assessed according to British standard 1006-1978 and the washing fastness according to
Indian standard (ISO method) at 60 0C/30 min. The rubbing fastness was tested using crock
meter (10 stroke To & fro) (Atlas) AATCC-1961. The percentage of exhaustion and fixation
of dyes on polyester fabric was determined by following the reported method20.
Results and Discussion
All the dyes were obtained as amorphous powder ranging in colour from yellowish orange to
dark brown. The TLC results showed that only a single spot was observed for each dye.
Characteristic data of Schiff’s base and dyes
2,2'-{Sulfonylbis[4,1-phenylenenitrilomethylylidene]}diphenol (SB). Yield: 79.65%, m.p.:
0
221-223 C (uncorrected). Calculated for C26H20N2O4S: m.wt.: 456; C, 68.42 %; H, 4.38%;
N, 6.41%; S, 7.01%. Found: C, 68.20%; H, 4.18%; N, 6.31%; S, 6.95%. IR (KBr, cm-1):
3032 (C−H aromatic), 1650 (>C=N−), 1495 (C=C aromatic), 1325 (C−N), 1195, 1375
1
(phenol, O−H bending and O−C stretching), 1145, 1305 (sulfones –SO2–). H-NMR (400
MHz, DMSO-D6 solvent, δ / ppm), 6.8-8.17 (16H, m, Ar−H), 8.52 (2H, s, N=CH), 12.63
(2H, s, Ar−OH).
2-[(4-{4-[(2-Hydroxy-5-p-tolylazobenzylidene)amino]benzenesulfonyl}phenylimino)
methyl]-4-p-tolylazo phenol (D1)
Yield: 64.16%, m.p.: 135-137 0C (uncorrected). Rf value: 0.88; Calculated for C40H32N6O4S:
m.wt.: 692; C, 69.36%; H, 4.62%; N, 12.13%; S, 4.62%. Found: C, 69.25%; H, 4.33%; N,
12.04%; S, 4.50%. IR (KBr, cm-1) 3036 (C−H aromatic), 1631 (>C=N−), 1590 (−N=N−),
1435 (−CH3 C−H bending), 1180, 1336 (phenol, O−H bending and O−C stretching),
1340 (C−N), 1499, 1456 (C−C multiple aromatic), 1445, 1278 (sulfones –SO2–), 825
1
(aromatic substitution, two adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent, δ
/ ppm) 2.24 (6H, s, Ar−CH3), 6.88-8.17 (22H, m, Ar−H), 8.46 (2H, s, N=CH), 12.46
(2H, s, Ar−OH).
2-[(4-{4-[(2-Hydroxy-5-phenlazobenzylidene)amino]benzenesulfonyl}phenylimino)
methyl]-4-phenylazophenol (D2)
Yield: 71.08%, m.p.: 141-143 0C (uncorrected), Rf value: 0.87. Calculated for C38H28N6O4S:
m.wt.: 664; C, 66.67%; H, 4.21%; N, 12.65%; S, 4.81%. Found: C, 68.45%; H, 4.11%; N,
12.5%; S, 4.75%. IR (KBr, cm-1): 3029 (C−H aromatic), 1632 (>C=N−), 1594 (−N=N−),
1181, 1332 (phenol, O−H bending and O−C stretching), 1339 (C−N), 1499, 1456 (C−C
multiple aromatic), 1150, 1290 (sulfones −SO2−), 832 (aromatic substitution, two adjacent
H-atom). 1H-NMR (400 MHz, DMSO-D6 solvent, δ / ppm) 7.28-8.16 (24H, m, Ar−H), 8.45
(2H, s, N=CH), 12.44 (2H, s, Ar−OH).

1221
B. C. DIXIT et al.
2-{[4-(4-{[2-Hydroxy-5-(4-nitrophenylazo)benzylidene}aminobenzenesulfonyl)
phenylimino] methyl}-4-(4-nitrophenylazo)phenol (D3)
Yield: 65.30%, m.p.: 156.158 0C (uncorrected), Rf value: 0.86. Calculated for C38H26N8O8S:
m.wt.: 754; C, 60.47%; H, 3.44%; N, 14.85 %; S, 4.24%. Found: C, 60.41%; H, 3.40%; N,
14.75%; S, 4.20%. IR (KBr, cm-1): 3241 (C−H aromatic), 1663 (>C=N−), 1589 (−N=N−),
1502, 1334 (C−NO2 aromatic), 1186, 1378 (phenol, O−H bending and O−C stretching),
1388 (C−N), 1635, 1589, 1435 (C−C multiple aromatic) 1146, 1278 (sulfones –SO2−), 832
1
(aromatic substitution, two adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent,
δ / ppm) 7.2-8.17 (22H, m, Ar−H), 8.47 (2H, s, N=CH), 12.47 (2H, s, Ar−OH).
2-{[4-(4-{[2-Hydroxy-5-(3-nitrophenylazo)benzylidene]amino}benzenesulfonyl)
phenylimino]methyl-4-(2-nitrophenylazo)phenol (D4)
Yield: 58.35%, m.p.: 137-139 0C (uncorrected), Rf value: 0.85. Calculated for C38H26N8O8S:
m.wt.: 754; C, 60.47%; H, 3.44%; N, 14.85%; S, 4.24% Found: C, 60.35%; H, 3.35%; N,
14.78%; S, 4.20%. IR (KBr, cm-1): 3032 (C−H aromatic), 1633 (>C=N−), 1587 (−N=N−),
1504, 1345 (C−NO2 aromatic), 1185, 1374 (phenol O−H bending and O−C stretching), 1336
(C−N), 1633, 1585, 1433 (C−C multiple aromatic), 1145, 1305 (sulfones −SO2−), 832
1
(aromatic substitution two adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent,
δ / ppm) 6.90-8.47 (22H, m, Ar−H), 8.49 (2H, s, N=CH), 12.43 (2H, s, Ar−OH).
4-(3-Chlorophenylazo)-2-{[4(4-{[5-(3-chlorophenylazo)-2-hydroxybenzylidene]
amino}benzenesulfonyl)phenyliminomethyl}phenol (D5)
Yield: 75.58%, m.p.: 148-150 0C (uncorrected), Rf value: 0.94. Calculated for
C38H26N6Cl2O4S: m.wt.: 733; C,62.21%; H, 3.54%; N, 11.45%; Cl, 9.68%; S, 4.36% Found:
C, 62.15%; H, 3.51%; N, 11.36%; Cl, 9.55%; S, 4.31%. IR (KBr, cm-1): 3035 (C−H
aromatic), 1631 (>C=N−), 1585 (−N=N−), 1184, 1377 (phenol O−H bending and O−C
stretching), 1601, 1584, 1498 (C−C multiple aromatic), 1335 (C−N), 1150, 1300 (sulfones –
1
SO2−), 833 (aromatic substitution two adjacent H-atom), 710 (C−Cl). H-NMR (400 MHz,
DMSO-D6 solvent, δ / ppm) 7.0-8.27 (22H, m, Ar−H), 8.44 (2H, s, N=CH), 12.47 (2H, s,
Ar−OH).
2-{[4-(4-{[2-Hydroxy-5-(2-nitrophenylazo)benzylidene]amino}benzenesulfonyl)
phenylimino}methyl}-4-(2-nitrophenylazo)phenol (D6)
0
Yield: 78.78%, m.p.: 152-155 C (uncorrected), Rf value: 0.92. Calculated for C38H26N8O8S:
m.wt: 754; C, 60.47%; H, 3.44%; N, 14.85%; S, 4.24%. Found: C, 60.35%; H, 3.40%; N,
14.20%; S, 4.14%. IR (KBr, cm-1): 3030 (C−H aromatic), 1640 (>C=N−), 1590 (−N=N−),
1510, 1350 (C−NO2 aromatic), 1183, 1370 (phenol, O−H bending and O−C stretching), 1605,
1575, 1507 (C−C multiple bond aromatic), 1334 (C−N), 1148, 1307 (sulfones –SO2−), 833
1
(aromatic substitution, two adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent, δ /
ppm) 6.95-8.21 (22H, m, Ar−H), 8.45 (2H, s, N=CH), 12.49 (2H, s, Ar−OH).
4-(4-Chlorophenylazo)2-{[4-(4-{[5-(4-chlorophenylazo)-2-hydroxybenzylidene
amino}benzenesulfonyl)phenylimino]methyl}phenol (D7)
Yield: 75.0%, m.p.: 150-152 0C (uncorrected), Rf value: 0.88. Calculated for
C38H26N6Cl2O4S: m.wt: 733; C, 62.21%; H, 3.54%; N, 11.45%; S, 4.36%; Cl, 9.68%. Found:
C, 62.11%; H, 3.45%; N, 11.40%; S, 4.26%; 9.61%. IR (KBr, cm-1): 3238 (C−H aromatic),
1632 (>C=N−), 1591 (−N=N−), 1178, 1397. (phenol O−H bending and O−C stretching),

Assessment of Dyeing properties of Novel Bisazo-Bisazomethine
1222
1632, 1540, 1492 (C−C multiple bond aromatic), 1333 (C−N), 1145, 1279 (sulfones –
SO2−), 694 (C−Cl), 831 (aromatic substitution, two adjacent H-atom). 1H-NMR
(400 MHz, DMSO-D6 solvent, δ / ppm) 7.19-8.15 (22H, m, Ar−H), 8.46 (2H, s, N=CH),
12.48 (2H, s, Ar−OH).
4-(4-Hydroxyphenylazo)-2-{[4-(4-{[5-(4-hydroxyphenylazo)-2-hydroxybenzylidene]
amino}benzenesulfonyl)phenylimino]methyl}phenol (D8)
Yield: 55.56%, m.p.: 139-141 0C (uncorrected), Rf value: 0.85. Calculated for C38H28N6O6S:
m.wt.: 696; C, 65.51%; H, 4.02%; N, 12.06%; S, 4.59%. Found: C, 65.38%; H, 3.95%; N,
11.98%; S, 4.45%. IR (KBr, cm-1): 3032 (C−H aromatic), 1631 (>C=N−), 1595 (−N=N−),
1195, 1399 (phenol O−H bending and O−C stretching), 1610, 1590, 1490 (C−C multiple
bond aromatic), 1331 (C−N), 1148, 1280 (sulfones –SO2−), 831 (aromatic substitution, two
1
adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent, δ / ppm) 6.87-8.18 (22H, m,
Ar−H), 8.45 (2H, s, N=CH), 12.44 (2H, s, Ar−OH terminal), 10.84 (2H, s, Ar−OH).
4-(3-Hydroxyphenylazo)-2-{[4-(4-{[5-(3-hydroxyphenylazo)-2-hydroxybenzylidene]
amino}benzenesulfonyl)phenylimino]methyl}phenol (D9)
Yield: 73.89%, m.p.: 171-173 0C (uncorrected), Rf value: 0.83. Calculated for C38H28N6O6S:
m.wt.: 696; C, 65.51%; H, 4.02%; N, 12.06%; S, 4.59%. Found: C, 65.35%; H, 4.03%; N,
12.02%; S, 4.49%. IR (KBr, cm-1): 3063 (C−H aromatic), 1625 (>C=N−),
1591(−N=N−), 1187, 1380 (phenol O−H bending and O−C stretching), 1337 (C−N),
1624, 1591, 1500 (C−C multiple bond aromatic), 1146, 1278 (sulfones –SO2−), 833
1
(aromatic substitution, two adjacent H-atom). H-NMR (400 MHz, DMSO-D6 solvent,
δ / ppm) 6.88-8.13 (22H, m, Ar−H), 8.46 (2H, s, N=CH), 9.91 (2H, s, Ar−OH terminal),
12.48 (2H, s, Ar−OH).
4-(4-Bromophenylazo)-2-{[4-(4-{[5-(4-bromophenylazo)-2-hydroxybenzylidene]
amino}benzenesulfonyl)phenylimino]methyl}phenol (D10)
Yield: 57.18%, m.p.: 155-157 0C (uncorrected), Rf value: 0.88. Calculated for
C38H26N6Br2O4S: m.wt.: 822; C, 55.47%; H, 3.16%; N, 10.21%; Br, 19.46%; S, 3.89%.
Found: C, 55.37%; H, 3.11%; N, 10.15%; Br, 19.35%; S, 3.75%. IR (KBr, cm-1): 3080
(C−H aromatic), 1633 (>C=N−), 1585 (−N=N−), 1180, 1375. (phenol O−H bending and
O−C stretching), 1340 (C−N), 1595, 1570, 1495 (C−C multiple bond aromatic), 1144, 1310
(sulfones –SO2−), 1340 (C−N), 835 (aromatic substitution, two adjacent H-atom), 545
1
(C−Br). H-NMR (400 MHz, DMSO-D6 solvent, δ / ppm) 7.18-8.16 (22H, m, Ar−H), 8.44
(2H, s, N=CH), 12.42 (2H, s, Ar−OH).
The result of the elemental analysis of each dye is consistent with the predicted
structure as shown in Scheme 1. The number of azo groups and methine groups are two in
each dye molecule. The nitrogen content and number of azo groups and number of
azomethine groups are correlated with the expected values. IR spectrum of each dye
exhibited the important features of aromatic, azo, hydroxyl, azomethine, nitro, halo and
1
sulfonyl groups. The H NMR spectra also showed the important signals at their expected
positions for all bisazo-bisazomethine disperse dyes. Thus, the structure of
bisazo-bisazomethine disperse dyes were confirmed as shown in Scheme 1. The
absorption maxima (λmax) in the visible spectra of all dyes recorded in DMF fall in the
range of 420-535 nm as shown in Table 1. The value of the logarithm of the molar
extinction coefficient (log ε) of all the dyes were in the range of 4.15-4.41, which
consistent with their high absorption intensity.

1223
B. C. DIXIT et al.
O
S
2
CHO
+
H2N
NH2
O
OH
N
RT
O
S
N
OH
O
HO
I (SB)
_
NaNO2 , HCl
0 - 5 oC
+
N2Cl
2 R3
2 R3
+
NH2
I (SB)
R2
R2
R1
R1
R3
N
N
O
N
N
R3
R2
R1
N
S
N
OH
O
R1
R2
HO
II (Disperse Dye)
Scheme 1. Synthetic route for the preparation of bisazo-bisazomethine disperse dyes {D1-D10}
Where R1, R2 and R3 substituent of aromatic amines are given below:
Dye No.
D1
D2
R1
H
R2
H
R3
CH3
H
Amines
4-Methylaniline
Aminobenzene
4-Nitroaniline
3-Nitroaniline
3-Chloroaniline
2-Nitroaniline
4-Chloroaniline
4-Hydroxyaniline
3-Hydroxyaniline
4-Bromoaniline
H
H
D3
D4
H
H
NO2
H
H
NO2
Cl
H
D5
D6
H
H
NO2
H
H
H
Cl
OH
H
D7
D8
H
H
D9
D10
H
OH
H
H
Br
Moreover, the presence of electron donating or electron attracting groups did not bring
about any marked increase in λmax in the visible region and log ε remained nearly constant.
However, electron attracting substitutions such as –Cl and –NO2 increase the polarizability.
This leads to a decrease in the energy between the highest occupied molecular orbital and
lowest unoccupied molecular orbital and thus, the π→π* electronic transition occurs with
lower frequency photons, resulting in a bathochromic shift of the visible absorption band.
Dying properties of the dyes
The dispersed dyes were applied at 2% depth on polyester fabric. The result of exhaustion of
the dye bath and the fixation of the dyed fabric are given in Table 1. These dyes gave a wide
range of colours varying from yellowish orange to dark brown with good levelness,
brightness and depth on the fabric. The variation in the shades of the dye fabric results from

Assessment of Dyeing properties of Novel Bisazo-Bisazomethine
1224
both the nature and position of the substituent present on the diazotised compound. The
dyeing showed an excellent fastness to washing, perspiration and sublimation but showed
poor rubbing fastness and is shown in Table 2. A remarkable degree of levelness after
washing was observed. This may be attributed to the good penetration into and affinity of
the dye for the fabric structure.
Table 1. Absorption maxima (λmax), intensities (log ε), exhaustion (E) and fixation (F) of
bisazo-bisazomethine disperse dyes on polyester fabric
Dye
No.
D1
D2
D3
D4
D5
D6
D7
D8
Absorption maxima
max/nm in DMF
Disperse dyeing on polyester
λ
log ε
4.33
4.15
4.41
4.22
4.32
4.41
4.32
4.26
% E
74
67
65
68
72
70
79
75
% F
77
78
66
71
71
68
76
69
440
420
535
472
441
481
460
490
D9
D10
433
428
4.28
4.17
82
62
82
63
Table 2. Results of bisazo-bisazomethine disperse dyeing and various fastness properties of
the dye on polyester fabric
Rubbing
fastness
Perspiration
fastness
Dye Color shades on
Light Washing
Sublimation
fastness
no.
polyester fabric fastness fastness
Acid Alkaline
Dry Wet
D1
D2
D3
D4
D5
D6
D7
D8
D9
D10
5
5
5
4
4.5
5
5
5
5
5
5
5
4
5
4
5
5
5
3
3
Yellowish orange
Light Orange
Light Brown
3.4 3.4
5
4
5
5
3
4
3
4.4
5
5
4.5
5
5
3.4
Brownish Yellow
Light Orange
Yellowish Brown
Light Orange
Dark Yellow
5
5
3.3 3.4
3.4
3.3 3.3
4.5
4
5
5
5
4
4.5
3
4
4.5
4
4
4
3
3.4
3
3
3
5
4.5
5
5
5
Dark Yellow
5
5.3
5
3.4
Dark Brown
Conclusion
Novel bisazo-bisazomethine disperse dyes were prepared and duly characterized. They have
good fastness to light, sublimation and perspiration properties but exhibit poor rubbing
fastness. The nature of the substituent in the coupling components has little influence on the
visible absorption and the shade of the dyeing.
Acknowledgment
The authors are grateful to the principal, for providing the necessary research facilities.

1225
B. C. DIXIT et al.
References
1.
2.
3.
4.
Mohamed S K and Nour EI-Din A M, J Chem Res., 1999, 8, 508-509.
Peters A T and Walker D, J Chem Soc., 1956, 1429-1436
Naik R D, Desai C K and Desai K R, Orient J Chem., 2000, 16, 159.
Gorden P F and Gregory P, Organic Chemistry in Color, 1st Ed., Springer Verlag,
Berlin, Heidelberg, New York, 1983, 60.
5.
6.
7.
Yurteri S, Onen A and Yagci Y, Eur Polym J., 2002, 38, 1845-1850.
Griffiths J, Bello K A and Chong L, J Chem Soc., Perkin Trasactions, 1981, 2, 815.
Stopa B, Konieczny L, Piekarska B, Roteman I, Rybarska J and Skowronek M,
Biochimie., 1997, 79, 23-26.
8.
9.
Dayananda B P and Revanasiddappa H D, Chemical Papers, 2007, 61(6), 446-451.
Wang M, Funabiki K and Matsui M, Dyes and Pigments, 2003, 57(1), 77-86.
10. Mali N J, Mistry B D and Desai K R, Oriental J Chem., 2000, 16, 185.
11. Matsui M, Kamino Y, Hayashi M, Funabiki K, Shibata K, Muramatsu H, Abe Y and
Kaneko M, Liq Cryst., 1998, 25, 235-240.
12. Asiri A M, Dyes and Pigments, 1999, 42, 209.
13. Asiri A M, Bull Korean Chem Soc., 2003, 24(4), 426-430.
14. Asiri A M, J Chem Soc Pak., 2004, 26, 57-60.
15. Vogel A I, A Textbook of Practical Organic Chemistry, 3rd Ed., Longman, London
1961, 620.
16. Frirz-David H E and Blengy L, Fundamental process of Dye Chemistry, 3rd Ed.,
Wiley, New York, 1949, 241.
17. Szymczyk M, Shafei A E and Freeman H S, Dyes and Pigments, 2007, 72, 8.
18. Dixit B C, Patel H M and Desai D J, J Serb Chem Soc., 2007, 72(2), 119.
19. Maradiya H R and Patel V S, High Perform Polym., 2000, 12, 335.
20. Maradiya H R and Patel V S, Fibres and Polym., 2002, 3, 43.

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