Pyridazine derivatives and related compounds. 23*. synthesis of 3-substituted pyrazolo[3,4-c] pyridazines and their application as disperse dyes

Article abstract of DOI:10.1007/s10593-010-0494-1

Acetylacetone and malononitrile were coupled with diazotized arylamines to give arylazoacetylacetones and arylazomalononitriles. When refluxed with 3-hydrazino-4,5-diphenyl-1H-pyrazolo-[3,4-c]pyridazine in the presence of ethanol/HCl, they yielded the corresponding 3-[4-(arylazo)-3,5-dimethylpyrazol- 1-yl]- and 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4- c]pyridazine dyes. The dyes were applied to polyester and polyamide fabrics, and their spectral and fastness properties were measured.

Full text of DOI:10.1007/s10593-010-0494-1

Chemistry of Heterocyclic Compounds, Vol. 46, No. 2, 2010
PYRIDAZINE DERIVATIVES AND RELATED
COMPOUNDS. 23*. SYNTHESIS OF 3-SUBSTITUTED
PYRAZOLO[3,4-c]PYRIDAZINES AND THEIR
APPLICATION AS DISPERSE DYES
A. Deeb1*, F. Yassin1, N. Ouf1, and W. Shehta1
Acetylacetone and malononitrile were coupled with diazotized arylamines to give arylazoacetyl-
acetones and arylazomalononitriles. When refluxed with 3-hydrazino-4,5-diphenyl-1H-pyrazolo-
[3,4-c]pyridazine in the presence of ethanol/HCl, they yielded the corresponding 3-[4-(arylazo)-3,5-di-
methylpyrazol-1-yl]- and 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyri-
dazine dyes. The dyes were applied to polyester and polyamide fabrics, and their spectral and fastness
properties were measured.
Keywords: 3-hydrazino-1H-pyrazolo[3,4-c]pyridazine, monoazo dyes, color fastness.
Derivatives of the pyrazolopyridazine ring systems are known to possess potent biological and
pharmacological properties [2-4]. On the other hand, some pyrazole derivatives are very important compounds
due to their biological and pharmacological activities [5]. They are also used as a key starting material for the
synthesis of commercial aryl/hetarylazopyrazole dyes [6]. All these properties aroused our interest in the
synthesis of new heterocyclic compounds, including the pyrazolo[3,4-c]pyridazine moiety, which is a
continuation of our previous work [7-12]. The present investigation deals with the synthesis of some 3-[4-
(arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine and 3-[3,5-diamino-4-(arylazo)-
pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine dyes from 3-hydrazino-4,5-diphenyl-1H-pyrazolo-
[3,4-c]pyridazine and evaluation of their properties on polyester and polyamide fabrics.
Ph
Ph
N2
NHNH2
Ph
Ph
SnCl2 / HCl
r. t.
N
N
N
N
N
N
N
N
H
1
2
_______
* For Communication 22 see [1].
** To whom correspondence should be addressed, e-mail: dralideeb@hotmail.com.
1 Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt.
__________________________________________________________________________________________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 262-274, February, 2010. Original
article received April 7, 2008, revised version submitted December 30, 2009.
212
0009-3122/10/4602-0212©2010 Springer Science+Business Media, Inc.

3-Hydrazino-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine 2 [13] was prepared in 96% yield as yellow
crystals (mp 168°C) by reduction of 3-diazo-4,5-diphenylpyrazolo[3,4-c]pyridazine 1 with stannous chloride/HCl at
room temperature.
Ar
N
N
CHX2
CH2X2
+
N
NaNO2 / HCl
0–5°C
4a,b
5a–t
–
ArNH2
NCl
Ar
0–5°C
AcONa
pH 3–4
3
Ar
N
N
CX2
H
4 a X = COMe, b X = CN; 5 a,k Ar = Ph, b,l Ar =2-MeOC6H4, c,m Ar = 4-MeOC6H4, d,n Ar = 2-ClC6H4,
e,o Ar = 3-ClC6H4, f,p Ar = 2-MeC6H4, g,q Ar = 3-MeC6H4, h,r Ar = 4-MeC6H4, i,s Ar = 4-O2NC6H4,
j,t Ar = 2-naphthyl; a-j X = COMe, k-t X = CN
TABLE 1. Characteristics of Arylazoacetylacetone and Arylazomalono-
nitrile Derivatives 5a-t
Found, %
——————
Calculated, %
Com-
pound
Empirical
formula
mp*, °C
88–89
Yield, %
85
C
H
N
5a
C11H12N2O2
64.50
64.69
5.80
5.92
13.80
13.72
5b
5c
5d
5e
5f
C12H14N2O3
C12H14N2O3
C11H11ClN2O2
C11H11ClN2O2
C12H14N2O2
C12H14N2O2
C12H14N2O2
C11H11N3O4
C15H14N2O2
C9H6N4
61.50
61.53
61.50
61.53
55.20
55.36
55.30
55.36
65.90
66.04
66.10
66.04
66.10
66.04
53.10
53.01
70.70
70.85
63.40
63.52
60.10
60.00
59.90
60.00
52.70
52.83
52.90
52.83
65.10
65.21
65.20
65.21
5.90
6.02
6.10
6.02
4.60
4.65
4.70
4.65
6.40
6.47
6.40
6.47
6.60
6.47
4.40
4.45
5.40
5.55
3.40
3.55
4.00
4.03
4.10
4.03
2.40
2.46
2.50
2.46
4.40
4.38
4.30
4.38
12.10
11.96
11.90
11.96
11.60
11.74
11.70
11.74
12.70
12.84
12.80
12.84
12.60
12.84
16.70
16.86
11.10
11.02
33.00
32.92
28.10
27.99
28.00
27.99
27.50
27.38
27.40
27.38
30.30
30.42
30.50
30.42
117-119
99-100
117-118
92-94
90
91
89
90
87
88
88
92
86
78
81
82
84
85
80
79
80
85
83
118-119
80-81
5g
5h
5i
94-96
208-209
223-25
144-145
112-114
142-143
100-102
169-171
99-100
151-153
171-172
224-226
188-189
5j
5k
5l
C10H8N4O
C10H8N4O
C9H5ClN4
C9H5ClN4
C10H8N4
5m
5n
5o
5p
5q
5r
5s
5t
C10H8N4
C10H8N4
65.30
65.21
50.10
50.24
80.00
70.90
4.50
4.38
2.30
2.34
3.60
3.66
30.40
30.42
32.60
32.55
25.30
25.44
C9H5N5O2
C13H8N4
_______
* Recrystallization solvent: chloroform.
213

Diazotized arylamines 3 were coupled with active methylene compounds such as acetylacetone 4a and
malononitrile 4b in sodium acetate buffered solution to give azobenzeneacetylacetone and azobenzene-
malononitrile derivatives 5a-j and 5k-t in good yield, respectively. Spectral data [14] for such compounds indicate
them to have a hydrazone configuration [15]. The characteristics of compounds 5a-t are shown in Table 1.
R
N
N
Ph
N
Ph
Heat
N
N
2
5a–t
+
N
N
R
N
H
Ar
6a–t
6 a,k Ar = Ph, b,l Ar =2-MeOC6H4, c,m Ar = 4-MeOC6H4, d,n Ar = 2-ClC6H4,
e,o Ar = 3-ClC6H4, f,p Ar = 2-MeC6H4, g,q Ar = 3-MeC6H4, h,r Ar = 4-MeC6H4,
i,s Ar = 4-O2NC6H4, j,t Ar = 2-naphthyl; a-j R = Me, kꢀt R = NH2
TABLE 2. Characteristics of Compounds 6a-t
Found, %
——————
Calculated, %
Empirical
formula
Dye
mp*, °C
Yield, %
C
H
N
6a
6b
6c
6d
6e
6f
C28H22N8
71.30
71.47
69.60
69.59
69.70
69.59
66.70
66.60
66.40
66.60
71.90
71.88
71.80
71.88
71.70
71.88
65.20
65.23
73.70
73.83
66.00
66.09
64.40
64.53
64.50
64.53
61.50
61.60
61.50
61.60
66.50
66.65
4.80
4.71
4.80
4.83
4.70
4.83
4.10
4.19
4.20
4.19
5.10
4.99
4.90
4.99
5.20
4.99
4.00
4.11
4.60
4.65
4.20
4.27
4.30
4.41
4.50
4.41
3.90
3.78
3.70
3.78
4.50
4.56
23.70
23.81
22.30
22.39
22.40
22.39
22.10
22.19
22.30
22.19
23.00
23.12
23.20
23.12
23.10
23.12
24.50
24.45
21.60
21.52
29.90
29.64
27.90
27.87
27.70
27.87
27.60
27.63
27.70
27.63
28.90
28.79
>300
211-212
219-221
174-175
291-293
299-300
212-213
>300
85
94
93
78
95
90
75
94
95
77
72
80
92
80
93
75
75
76
83
72
C29H24N8O
C29H24N8O
C28H21ClN8
C28H21ClN8
C29H24N8
6g
6h
6i
C29H24N8
C29H24N8
C28H21N9O2
C32H24N8
>300
6j
193-195
260-262
>300
6k
6l
C26H20N10
C27H22N10O
C27H22N10O
C26H19ClN10
C27H22ClN10
C27H22N10
C27H22N10
C27H22N10
C26H19N11O2
C30H22N10
6m
6n
6o
6p
6q
6r
6s
6t
149-151
245-246
240-242
150–151
>300
66.60
66.65
66.60
66.65
60.30
60.34
68.90
68.95
4.60
4.56
4.70
4.56
3.60
3.70
4.10
4.24
28.60
28.79
28.70
28.79
29.80
29.77
26.90
26.80
179-181
214-215
165-167
_______
* Recrystallization solvent: DMF.
214

TABLE 3. Spectral Characteristics of Compounds 6a-t
Com-
pound
MS,
IR (KBr), Ȟ, cm–1
3155, 3061, 2970
1H NMR, į, ppm*
m/e M+
6a
2.18 (3H, s, CH3); 2.27 (3H, s, CH3);
6.99-7.76 (15H, m, H Ar),
15.19 (1H, br. s, NH)
470.2
6b
6c
6d
6e
3162, 3066, 2972, 2856
3171, 3070, 2973, 2850
3182, 3071, 2960
500.24
500.2
504.2
504.1
3216, 3066, 2970
2.18 (3H, s, CH3); 2.28 (3H, s, CH3);
7.0-7.7 (14H, m, H Ar);
15.2 (1H, br. s, NH)
6f
6g
6h
6i
3200, 3060, 2970
3184, 3060, 2960
3190, 3065, 2965
3212, 3081, 2974,
1525, 1342
484.21
484.23
484.2
515.15
6j
3156, 3063, 2972
3400, 3300, 3160, 3060
520.2
470.2
6k
5.4 (4H, br. s, 2NH2); 6.98-7.5 (15H, m, H Ar);
13.22 (1H, br. s, NH)
6l
3425, 3380, 3182, 3061, 2857
3365, 3334, 3158, 3060, 2854
502.3
502.2
6m
3.78 (3H, s, CH3); 5.5 (4H, br. s, 2NH2);
6.94-7.67 (14H, m, H Ar);
14.9 (1H, br. s, NH)
6n
6o
6p
6q
6r
6s
6t
3350, 3304, 3182, 3060
506.24
506.17
486.5
486.9
486.7
517.2
522.3
3361, 3310, 3180, 3062
3380, 3328, 3170, 3062, 2987
3372, 3324, 3181, 3060, 2987
3385, 3325, 3162, 3062, 2986
3476, 3360, 3190, 1524, 1340
3394, 3324, 3150, 3058
_________
* The 1H NMR spectra were obtained in DMSO-d6 (compounds 6a,e,m) and
CDCl3 (compound 6k).
Compound 2 when reacted with azobenzeneacetylacetone derivatives 5a-j in ethanol/HCl yields
3-[4-(arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine dyes 6a-j. The reaction
proceeds in two stages, viz. the initially formed hydroxypyrazoline subsequently loses water by an acid-
catalyzed reaction [16, 17]. Compound 2, when reacted with azobenzenemalononitrile derivatives 5k-t in a
similar manner, gives 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines
6k-t. The characteristics and spectral data of compounds 6a-t are shown in Tables 2 and 3.
The absorption maxima of dyes 6a-t were recorded in DMF and are shown in Table 4. The absorption
maxima of dyes 6a-j varied from 343 to 372 nm, and those of dyes 6k-t from 352 to 400 nm. It was observed in
general that dyes 6k-t derived from azobenzenemalononitrile derivatives 5k-t were bathochromic when
compared with analogous dyes 6aj derived from azobenzeneacetylacetone derivatives 5a-j. This bathochromic
shift is attributed to the stronger electron release of the amino group with respect to the methyl group in
positions 3 and 5 of the pyrazole ring, thus enhancing electron delocalization in the dye molecule [18].
Dyeing of polyamide and polyester fabrics and dyeing properties [19]. 3-[4-(Arylazo)-3,5-di-
methylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines 6a-j and 3-[3,5-diamino-4-(arylazo)pyrazol-
1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines 6k-t were synthesized to assess their dyeing properties on
polyamide and polyester fabrics. The dyeing was performed at 2% shade by high-temperature techniques and
gave generally deep and bright intense hues, ranging from yellow to orange-yellow.
215

216

217

Versatility is the first technical property of the present dyes to be emphasized. Satisfactory color yields,
as compared with commercial dyes applied under similar conditions, were obtained at 2% depth, and excellent
leveling and exhaustion of dye liquors were also achieved. Furthermore, the dyes gave an excellent coloration
uniformity of polyamide and polyester without the use of a retarding agent. Relevant fastness data for the dyes
are given in Table 4, which reveals the following:
a) Excellent behavior is shown in fastness to washing at 50°C and to perspiration on dyed polyamide
and polyester fabrics.
b) Most of the dyes have a good to excellent rubbing fastness (4–5) (dry and wet); only a few of these
dyes have a good to moderate rubbing fastness (wet) and this may be attributed to inadequate diffusion of the
dye molecules into the fabrics.
c) Most of the dyes show a good sublimation fastness.
d) The light fastness of 3-[4-(arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyrid-
azines 6a-j and 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines 6k-t on
polyamide and polyester is significantly affected by the nature of the substituent in the arylazo component. In this
study the inclusion of the electron-withdrawing nitro group improves the light fastness. In most cases, the best light
fastness was obtained by dyes containing a nitro group in the arylazo component (e.g., dyes 6i and 6s).
The intensity of color for the dyes applied on polyamide and polyester fabrics expressed as K/S values
is given in Table 5. The following generalizations can be drawn.
The intensity of color for all dyes, expressed as K/S values, applied on nylon is greater than on
polyester fabrics.
a) The K/S values of dyes 6k-t derived from azobenzenemalononitrile derivatives 5k-t are greater than
those of dyes 6a-j derived from azobenzeneacetylacetone derivatives 5a-j. This bathochromic shift is attributed
to the stronger electron release of the amino group with respect to the methyl group in positions 3 and 5 of the
pyrazole ring, thus enhancing electron delocalization in the dye molecule and consequently increases the
vibration energy of the dye molecule, which in turn increases the color strength (K/S) values of the dyed fabrics
and directs the color towards reddish and yellowish directions on the red-green and yellow-blue axis,
respectively.
The color of the dyed fabric was assessed by tristimulus colorimetry. The results are listed in Table 6.
TABLE 5. K/S* Value of Dyes 6a-t on Polyamide and Polyester Fabrics at
Ȝ
max 420 nm
K/S
K/S
Dye
Dye
Polyamide
Polyester
Polyamide
Polyester
6a
6b
6c
6d
6e
6f
19.0
17.5
18.0
18.5
18.0
18.0
18.2
16.0
17.5
19.5
7.0
5.0
6k
6l
20.0
17.3
19.2
20.0
20.5
19.0
21.5
18.5
19.9
15.0
6.1
5.0
4.8
12.5
5.0
8.0
5.2
7.5
3.0
2.2
7.2
6m
6n
6o
6p
6q
6r
6s
9.5
11.2
3.4
6g
6h
6i
11.0
5.3
5.0
6j
12.8
6t
________
* K/S ꢀ color strength.
218

219

It was observed that
a) the color hues of dyes 6a-t on dyed polyamide and polyester fabrics are shifted towards the reddish
and yellowish directions on the red-green and yellow-blue axes, respectively;
b) dyes 3-[4-(arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines 6a-j are
lighter
than
the
corresponding
3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-
c]pyridazines 6k-t according to the color lightness values (L*);
c) 3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines 6k-t are brighter
than the corresponding 3-[4-(arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines
6a-j according to the color brightness values (C*).
We have come to the following conclusions. A set of 20 disperse dyes 6a-t was synthesized by the
reaction of 3-hydrazino-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine 2 with arylazoacetylacetone and arylazo-
malononitrile derivatives. All of them were investigated for their dyeing characteristics on polyamide and
polyester. The electronic absorption spectra cover a Ȝmax range of 343-400 nm at uniformly high absorption
intensity and give bright intense hues from yellow to orange-yellow on polyamide and polyester fabrics due to
the variations in polarity. The changes in color coordinates between dyes 6a-t (Table 6) are remarkable in view
of minor variations of the absorption maxima in solution. The dyed fabrics exhibit a very good to excellent (4-5)
washing, perspiration, rubbing, and sublimation fastness properties (Table 4). The remarkable degree of
levelness and brightness after washings is indicative of a good penetration and excellent affinity of these dyes
for the fabric due to the accumulation of polar groups. In combination with the ease of preparation, this makes
them particularly valuable.
EXPERIMENTAL
All melting points are uncorrected and are in °C. IR spectra were recorded on a Bruker Vector 22
1
Germany spectrometer (KBr). The H NMR spectra were obtained on a Varian Gemini 200 MHz spectrometer
using TMS as an internal standard. Electron impact mass spectra were obtained at 70 eV using a GCMS-qp1000
EX Shimadzu spectrometer. Electronic spectra were recorded on UV-Visible Recording Shimadzu
spectrophotometer from the dye solution in DMF at a concentration of 1˜10–5 mol/l.
Azobenzeneacetylacetone derivatives 5a-j (General Method). The appropriate arylamine 3 (0.01 mol)
was dissolved in aqueous hydrochloric acid (8 ml, 1:1) and cooled to 0-5°C, prior to the addition of a cold
solution of sodium nitrite (0.7 g in 3 ml water), while maintaining the temperature at 0-5°C. A diazonium salt
solution was then added dropwise to a cooled and stirred mixture of acetylacetone 4a (1.0 g, 0.01 mol) and
sodium acetate (2.0 g, dissolved in 10 ml of 50% aqueous ethanol). Stirring was continued for 1.5 h and the
resulting crystals collected, washed with water, and recrystallized from chloroform.
Azobenzenemalononitrile derivatives 5k-t (General Method). The above procedure was repeated,
except that acetylacetone 4a was replaced by malononitrile 4b.
3-[4-(Arylazo)-3,5-dimethylpyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazines
6a-j
(General Method). A mixture of 3-hydrazino-4,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine 2 (0.6 g, 2 mmol) and
arylazoacetylacetone 5a-j (2 mmol) was refluxed in ethanol (50 ml) with a few drops of hydrochloric acid for 10
h. The reaction mixture was cooled to room temperature and the separated solid was filtered off, washed with
water, dried, and recrystallized from DMF.
3-[3,5-Diamino-4-(arylazo)pyrazol-1-yl]-4,5diphenyl-1H-pyrazolo[3,4-c]pyridazines 6k-t. The above
procedure was repeated, except that arylazoacetylacetone was replaced by arylazomalononitrile 5k-t.
Dyeing and fastness determinations.
Dyeing procedure. The fabric was dyed with 2.0% dye (calculated by weight of the fabric) and 1 g/l
Viscavine as a dispersing agent, kept at a liquor ratio of 30:1. The process was started at 40°C (for polyamide
220

fabric) and 60°C (for polyester fabric) raised at a rate of 2°C/min to 98°C (for polyamide fabric) and 130°C (for
polyester fabric) and maintained there for 60 min. After cooling, the fabric was taken out and washed in a
solution containing 5 g/l detergent at 60°C for 15 min. Finally, the washed fabric samples were rinsed with
water and dried at ambient conditions.
Color fastness tests. The results are collected in Table 5.
(i) Fastness to washing.
A specimen of dyed fabric was stitched between two pieces of undyed wool and cotton fabric, all of
equal length, and then washed at 50°C for 30 min. The change in color of the dyed fabric and staining on the
undyed adjacent fabric were assessed according to the following grey scale: 1 – poor, 2 – fair, 3 – moderate, 4 –
good, 5 – excellent.
(ii) Fastness to perspiration.
The samples were prepared by stitching a piece of dyed fabric between two pieces of undyed wool and
cotton fabric, all of equal length, and then immersed into the acid solution for 30 min. The change in color of the
dyed fabric and staining on the undyed adjacent fabric were assessed according to the following grey scale: 1 –
poor, 2 – fair, 3 – moderate, 4 – good, 5 – excellent. The acid solution (pH 3.5) contained sodium chloride (10
g/l–1), lactic acid (1 g/l–1), disodium orthophosphate (1 g/l–1), and histidine monohydrochloride (0.25 g/l–1).
(iii) Fastness to rubbing.
The dyed fabric was placed on the base of the Crockmeter, so that it rested flat 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 forth twenty times by making ten complete turns of the crank according to the
international standard procedure. For the wet rubbing test, the testing squares were thoroughly immersed into
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 grey scale: 1 – poor, 2 – fair, 3 – moderate, 4 – good, 5 – excellent.
(iv) Fastness to sublimation.
Sublimation fastness was measured with an iron tester (Yasuda No. 138). The samples were prepared by
stitching a piece of dyed fabric between two pieces of undyed fabric, one of which was cotton and the other
similar to the fabric under test, all of equal length, and then treated at 160 and 180°C in case of testing
polyamide and 160, 180, and 210°C in case of testing polyester each for 1 min. Any staining on the undyed
adjacent fabric or change in color of the dyed fabric was assessed according to the following grey scale: 1 – poor,
2 – fair, 3 – moderate, 4 – good, 5 – excellent.
(v) Fastness to light.
Light fastness was determined by exposing the dyed fabric on a Xenotest 150 (Original Hanau, chamber
temperature 25–30°C, black panel temperature 60°C, relative humidity 50–60%, dark glass UV-filter system) for
40 h. The changes in color were assessed according to the following blue scale: 1 – poor, 3 – moderate, 5 – good, 8
– very good.
Color assessment. Table 6 reports the color parameters of the dyed fabric assessed by tristimulus
colorimetry. The color parameters of the dyed fabric were determined on a spectral multichannel photodetector
(model MCPD-110A), equipped with D65, tungsten, and fluorescent sources. The color of the dyed fabric was
assessed in terms of tristimulus colorimetry. The values of the chromaticity coordinates and luminance factor
and the positions of colors in the CIELAB color solid are reported.
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