Synthesis, characterization and dyeing assessment of novel acid azo dyes and mordent acid azo dyes based on 2-hydroxy-4-methoxybenzophenone on wool and silk fabrics

Article abstract of DOI:10.2298/JSC090704039D

Novel acid mono azo and mordent acid mono azo dyes were synthesised by the coupling of diazonium salt solution of different aromatic amines with 2-hydroxy-4-methoxybenzophenone. The resulting dyes were characterized by spectral techniques, i.e., elemental

Full text of DOI:10.2298/JSC090704039D

J. Serb. Chem. Soc. 75 (5) 605–614 (2010)
UDC 677.027.423.1/.2:535.683+535.685
JSCS–3991
Original scientific paper
Synthesis, characterization and dyeing assessment of
novel acid azo dyes and mordent acid azo dyes based on
2-hydroxy-4-methoxybenzophenone on wool and silk fabrics
1
1
2
*
BHARAT C. DIXIT , HITENDRA M. PATEL , RITU B. DIXIT
and DHIRUBHAI J. DESAI1
1Department of Chemistry, V. P. & R. P .T. P Science College, Vallabh Vidyanagar-388 120,
Gujarat and 2Ashok & Rita Patel Institute of Integrated Study & Research in Biotechnology
and Allied Sciences, New Vallabh Vidyanagar-388 120, Gujarat State, India
(Received 4 July 2009, revised 21 January 2010)
Abstract: Novel acid mono az o and mordent acid mono az o dy es were syn-
thesised by the coupling of diazoniu m salt solution of differe nt aromatic ami-
nes with 2-hydroxy-4-methoxybenzophenone. The resulting dyes were charac-
1
terized by spectral techniques, i.e., elemental analysis, IR, H-NMR and UV–
–visible spectroscopy. The dy eing performance of all the dyes was evaluated
on wool and silk fabrics. The dyeing of chrome pre-treated wool and silk fab-
rics showed better hues on mordented fabrics. Dyeing of wool and silk fabric s
resulted in pinkish blue to red shade s with very good depth and levelne ss. The
dyed fabrics showed excell ent to very good l ight, washing, perspiration, su b-
limation and rubbing fastne ss. The results of antibacterial st udies of chro me
pre-treated fabrics revealed t hat the toxicit y of m ordented dy es against
Escherichia coli, Staphylococcus aureus, Salmonella typhi, Bacillus subtilis
bacteria was fairly good.
Keywords: acid azo dye; mordent acid azo dye; light fastness; washing fastness.
INTRODUCTION
Traditionally, azo dyes are the most important class of commercial dyes, oc-
cupying more than half of the dye chemistry, which contain phenols as interme-
1–6
diates. If they contain sodium salts of a sulphonic acid group i n addition to a
phenolic group, they are referred as an acid azo dye. All such dyes having pheno-
lic and sulphonic acid moieties, contain hydroxyl (–OH) and sulphonic (–SO H)
3
groups as auxochrom ic groups. Such an auxochromic (–OH) and chromophoric
(C=O) groups-containing co mpound, i.e., 2-h ydroxy-4-methoxybenzophenone,
7–9
has shown wide applications as a polymer additive. It is also known for its ex-
*Corresponding author. E-mail: dixits20002003@yahoo.co.in
doi: 10.2298/JSC090704039D
605
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606DI
XIT et al.
cellent UV absorbing capacity, as it prevents the photo-degradabi lity of most vi-
10–12
nyl polymers.
The acid m ono azo dyes and mordent mono azo dyes forma-
13–16
tion based on this compound has not b een developed except in a few patents.
Considering the above-mentioned importance of 2-hydroxy-4-methoxybenzophe-
none, it was planned t o explore the field of acid a zo dy es based on this com-
pound, which may yield dyes with good hue properties.
17,18
Hence, in continuation of earlier work,
the present communication com-
prises the sy nthesis, characterization and dyeing assessment of novel acid mono
azo and m ordent acid m ono azo dy es based on 2-hydroxy-4-m ethoxybenzophe-
none. The proposed synthetic route is shown in Scheme 1.
Scheme 1. Proposed synthetic route for the 2-hydroxy-4-methoxybenzophenone
based dyes (D1–D7).
EXPERIMENTAL
All the e mployed che micals were of analy tical reagent gr ade. The aro matic a mines
shown in Table I were used for diazotization. W ool and silk fabrics were gift ed by Color Tax
(Pvt) Ltd., Surat, India. Melting points w ere determined by the open capillary method and are
given uncorrected. The UV–visible absorption spectra were measured on a Carl Zeiss UV/Vis
Specord spectrometer, and the elemental analysis was realized using a Perkin Elmer CHNS/O
Analyzer 2400 Series II. The infrared spectra were recorded in KBr pellets on a Perkin–Elmer
Spectrum GX FT-IR m odel. The 1H-NMR spectra were re corded on Hita chi R-1500 (40 0
MHz) in D MSO-d6 solvent and thin lay er c hromatography (TLC) was ru n on alu minium
sheets pre-coated with silica gel 60 F254 (Merck, Ger many) using a methanol–water–acetic
acid (12:3:7) solvent sy stem. The colour sp ots were vi sualized by a UV c abinet. A HTH P
dyeing machine (model LL) was used for dyeing.
Synthesis of acid mono azo dyes
Diazotization. Diazotization o f various aro matic a mines (sh own in Table I) was per-
formed by a reported method.19,20
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DYEING ASSESSMENT OF NOVEL ACID AZO DYES
607
Accordingly, each of the aromatic amines (3.19 g, 0.010 mol) was mixed with HCl (25
mL, 37 %) in a mortar, transferred to a 3-n eck round b ottom flask, and additional HCl (20
mL, 37 %) was added. To the resultant suspension, crushed ice (25 g) and NaNO 2 (2.5 mL, 4
M) were added. Diazotization was realized over 0.5 h at 0–5 °C under continuous stirring. The
complete synthetic route is shown in Scheme 1 and the structures of the various aromatic ami-
nes and the corresponding dyes are shown in Table I.
TABLE I. Structures of the aromatic amines and corresponding acid azo dyes
Dye
Aromatic amine
Acid azo dye structure
D1
HO3S
HO
D2
D3
O
N
N
OH
H3CO
D4
D5
D6
D7
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Coupling procedure. The coupling of ab ove mentioned diazotized aromatic amines (as
shown in Tabl e I) was perform ed by a m ethod reported in the literature. 19,20 The general
procedure followed is given b elow: 2-hydroxy-4-methoxybenzophenone (2.15 g, 0.010 m ol)
was dissolved in aqueous sodium hydroxide (100 mL, 0.10 M) solution. The clear solution
was cooled in an ice–salt bath and the diazonium salt solution of an aromatic amine was added
dropwise over a period of 30 min under vigorous stirring. The pH was maintained between 2.0
to 3.0 by the si multaneous ad dition of 10 % w/v sodi um c arbonate solution. Stirring was
continued for 2 h, allowing the temperature to rise to a mbient. The dy e was then filtered off
and di ssolved i n distill ed water. Then the a cid az o dy e w as o btained by the evaporation
procedure and subsequently dried at roo m te mperature. The dy es were designated a s aci d
mono azo dyes (D1–D7).
Acid mono azo dyeing method
Wool and silk fabrics are conveniently dyed in the laboratory at 90–130 °C and at a high
pressure (166–207 kPa). A model glycerine-bath, high-temperature beaker and HTHP (model
LL) dyeing machine were u sed. For this purpose, a pa ste of finely powdered acid azo dy e
(0.060 g) wa s prepared with a dispersing agent dodamol (0.090 g), wetti ng agent Tween-80
(0.0060 g) and water (2.0 mL) in a ball mill. Water (10 m L) was adde d to this past e under
stirring and the pH was adjusted to 2.0–4.0 u sing acetic acid. This dy e suspension (100 mL)
was added to a beaker provided with a lid an d a screw cap. A wetted p attern of wool or sil k
fabric was rolled into the beaker and the lid was placed on the beaker the metal cap tightened.
The beaker wa s then pla ced vertically on the rotatory carrier inside the ta nk and the cla mp
plate was firmly tightened.
The rotatory carrier was then a llowed to rotate in the glycerine-bath and the temperature
was raised to 90 °C at a rate of 2 ° C/min. The dyeing was continued for 1 h under pressure.
After cooling for 1 h, the beak er was removed from the bath and washed with distilled water.
The dyed pattern was thoroughly washed with cold water and dried at room temperature.
Mordent dyeing method
The wool a nd silk fabric dy e pattern obtained from the above-mentioned process was
treated with potassium dichromate solution equal to half of t he weight of the dye and it w as
allowed to roll into the beaker and again the beaker was then placed vertically on the rotatory
carrier inside the tank and the dyeing was continued for 1 h under pressure. After cooling for 1
h, the be aker was re moved f rom t he b ath a nd wa shed wit h cold distilled water. The dy ed
pattern was thoroughly washed with warm water and air dried at room temperature.
Determination of the percentage exhaustion and fixation
The percentage exhaustion and fixation of the dyed fabrics were determined according to
the reported methods.21
Fastness property
All the fastness properties of the synthesized dyes were assessed, i.e., the light, sublima-
tion and perspi ration fastnesses according to t he British standard: 1006-1978, the wash fa st-
ness according to the Indian st andard: IS: 765 -1979 and the rubbing fastn ess using a Croc k
meter (Atlas) AATCC-1961.
Antimicrobial activity
The in vitro an timicrobial acti vities of th e a cid azo chrome dyes were te sted agai nst
Escherichia coli, Staphylococcus aureus, Salmonella typhi and Bacillus subtilis bacteria using
agar nutrient as the medium. A stock solutio n of 250 pp m was prepare d by dissolving th e
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DYEING ASSESSMENT OF NOVEL ACID AZO DYES
609
compounds in 20 % DMSO solution. The anti
microbial activity was perfor med at a
concentration 100 μg/ml, using the agar-cup method in which the well diameter was 4 mm,22
with DMSO as the control.
RESULTS AND DISCUSSION
Physical properties of dyes
All the dy es obtained upon recry stallization from acetone were crystalline
powders ranging in col our from pinkish blue to red. The purity of the d yes was
checked by TLC using methanol–water–acetic acid (12:3:7 ) solvent sy stem. A
single spot was observed for each dye.
Analytical and spectral data of the dyes
4-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)-5-hydroxy-2,7-naphthalenedi-
sulphonic acid (D ). Yield: 78 % ; m .p.: 1 46–150 °C; Rf. value: 0.78. Anal.
1
Calcd. for C H O N S (FW 55 8): C, 51.61; H, 3.32; N, 5. 01; S, 1 1.46 %.
24 18 10 2 2
–1
Found: C, 51.59; H, 3. 21; N, 5.00; S, 11.38 %. IR (KBr, cm ): 3463 ( –OH),
3072 (=CH, aromatic), 1628 (C=O, diary l), 1521 (N=N), 1520 (for naphthalen e
substitution), 1481 (C=C, aro matic), 1 333 (C–N), 1101 (C–O), 1030, 650 (for
1
sulphonic acid), 732, 584, 481 (for substituted benzene). H-NMR (400 M Hz,
DMSO-d , δ / ppm): 3.82 (3H, s, Ar–OCH ), 5.4 (2H, s, Ar–OH), 7.2–7.4 (11H,
6
3
m, Ar–H), 8.0 (1H, s, –SO H), 8.2 (1H, s, –SO H).
3
3
7-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)-4-hydroxy-2-naphthalenesul-
phonic acid (D2). Yield: 80 % ; m.p.: 138–142 °C; Rf. value: 0.82. Anal. Calcd.
for C H O N S (FW 4 78): C, 6 0.25; H, 3.7 6; N, 5.85; S, 6.69 %. Found: C,
24 18
7 2
–1
60.20; H, 3.7 2; N, 5.83; S , 6.61 % . IR (KBr, cm ): 3450 (–OH), 3082 (=CH,
aromatic), 1624 (C=O, diary l), 1540 (for naphthalene substitution), 1522 (N=N),
1490 (C=C, aromatic), 1345 (C–N), 110 1 (C–O), 1032, 653 (for sulphonic acid),
1
744, 564, 478 (for substituted benzene).
H-NMR (400 MHz, DMSO-
-d , δ / ppm): 3.81 (3H, s, Ar–OCH ), 7.2–7.5 (12H, m, Ar–H), 5.42 (1H, s, Ar–
6
3
–OH), 6.3 (1H, s, Ar–OH), 8.2 (1H, s, –SO H).
3
4-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)-5-hydroxy-1,7-naphthalenedi-
sulphonic acid (D ). Yield: 79 % ; m .p.: 1 42–146 °C; Rf. value: 0.77. Anal.
3
Calcd. for C H O N S (FW 55 8): C, 51.61; H, 3.32; N, 5. 01; S, 1 1.46 %.
24 18 10 2 2
–1
Found: C, 51.58; H, 3. 19; N, 4.97; S, 11.34 %. IR (KBr, cm ): 3481 ( –OH),
3070 (=CH, aromatic), 1632 (C=O, diary l), 1542 (N=N), 1525 (for naphthalen e
substitution), 1483 (C=C, aro matic), 1 337 (C–N), 1103 (C–O), 1029, 650 (for
1
sulphonic acid), 737, 562, 472 (for substituted benzene). H-NMR (400 M Hz,
DMSO-d , δ / ppm): 3.82 (3H, s, Ar–OCH ), 7.1–7.3 (11H, m, Ar–H), 5.5 (2H, s,
6
3
Ar–OH), 7.9 (1H, s, –SO H), 8.35 (1H, s, –SO H).
3
3
6-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)-2-naphthalenesulphonic acid
(D ). Yield: 81 % ; m.p.: 131– 135 °C; Rf. valu e: 0.84. An al. Calcd. for
4
C H O N S (FW 462): C, 62.33; H, 3.89; N, 6.06; S, 6.92 %. Found: C, 62.27;
24 18
6 2
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–1
H, 3.83; N, 6.00; S, 6.89 %. IR (KBr, cm ): 3633 (–OH), 3080 (=CH, aromatic),
1652 (C=O, diary l), 1 560 (for napht halene substitution), 1 532 (N=N), 1473
(C=C, aromatic), 1338 (C–N), 1104 (C–O), 1032, 653 (for sulphonic acid), 782,
1
741, 583, 48 5 (for substit uted benzene). H-NMR (400 MHz, DMSO- d , δ /
6
/ ppm): 3.83 (3H, s, Ar–OCH ), 7.2–7.4 (13H, m, Ar–H), 6.1 0 (1H, s, Ar–OH),
3
8.1 (1H, s, –SO3H).
2-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)-1-naphthalenesulphonic acid
(D ). Yield: 79 % ; m.p.: 136– 141 °C; Rf. valu e: 0.82. An al. Calcd. for
5
C H O N S (FW 462): C, 62.33; H, 3.89; N, 6.06; S, 6.92 %. Found: C, 62.26;
24 18
6 2
–1
H, 3.84; N, 6.01; S, 6.88 %. IR (KBr, cm ): 3580 (–OH, phenolic), 3070 (=CH,
aromatic), 1621 (C=O, diary l), 1575 (for naphthalene substitution), 1531 (N=N),
1482 (C=C, aromatic), 1463 (C–N), 133 8 (C–O), 1034, 650 (for sulphonic acid),
1
1103, 732, 574, 473 (for substituted benzene). H-NMR (400 MHz, DMSO-d , δ
6
/ ppm): 3.82 (3H, Ar–OCH ), 7.1–7.5 (13H, m, Ar–H), 6.3 (1H, s, Ar–OH), 8 .2
3
(1H, s, –SO H).
3
2-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)benzoic acid (D ). Yield: 78
6
%; m.p.: 145–148 °C; Rf. value: 0.83. Anal. Calcd. for C H O N (FW 376):
21 16
5 2
–
C, 67.02; H, 4.25; N, 7.44 %. Found: C, 67.01; H, 4.18; N, 7.39 %. IR (KBr, cm
): 3430 (– OH, phenolic), 3540 (–OH, ac idic), 3062 (=CH, aro matic), 1634
(C=O, diaryl), 1678 (C=O, carboxylic acid), 1581 (N=N), 1483 (C=C, aromatic),
1
1352 (C–N), 1103 (C–O), 1100, 850 (f or carboxylic acid), 783, 741, 583, 482
1
(for substituted benzene). H-NMR (400 MHz, DMSO-d , δ / ppm): 3.82 (3H, s,
6
Ar–OCH ), 7.1–7.5 (11H, m, Ar–H), 5.5 (1H, s, Ar–OH), 10.9 (1H, s, –COOH).
3
4-(5-Benzoyl-4-hydroxy-2-methoxyphenylazo)benzenesulphonic acid (D ).
7
Yield: 83 %; m.p.: 150–154 °C; Rf. value: 0.85. Ana l. Calcd. for C H O N S
20 16
6 2
(FW 412): C, 58.25; H, 3.88; N, 6.79; S, 7.76 % . Found: C, 58. 18; H, 3.82; N,
–1
6.71; S, 7.70 % . IR (KBr, cm ): 3590 (–OH), 30 63 (=CH, aromatic), 1632
(C=O, diary l), 1533 (N=N), 1471 (C=C, aromatic), 1324 (C– N), 1103 (C– O),
1
1031, 652 (for sulphonic acid), 780, 744, 586, 475 (for substituted benzene). H-
-NMR (400 MHz, DMSO-d , δ / ppm): 3.82 (3H, s, Ar–OCH ), 7.2–7.4 (11H, m,
6
3
Ar–H), 6.1 (1H, s, Ar–OH), 7.9 (1H, s, –SO3H).
The results of ele mental analyses of each acid azo dy e were consistent with
the predicted structure, as shown in Table I. The number of azo group was almost
one for each dye. The nitrogen content and number of azo group for each dye are
co-related with each other. The IR spectrum of each dye comprised the important
features of aromatic, azo, hydroxyl, keto and carboxylic acid groups.
1
The H-NMR spectra of all the dy e compounds based on 2- hydroxy-4-me-
thoxybenzophenone show s im portant signals at their respective positions, con-
firming the structures of various acid azo d yes, as shown in Tabl e I. One of the
–OH protons in the D and D dyes might be merged with the aro matic protons,
1
3
while the other –OH protons in the othe r dyes resonated as a singl et between 5.4
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DYEING ASSESSMENT OF NOVEL ACID AZO DYES
611
to 6.3 δ. In the D dye, the –COOH proton gave a singlet at 10.9 δ. The singlet of
6
the –SO H proton resonated between 7.9 to 8.35 δ and –OCH protons resonated
3
3
as a singlet around 3.8 δ in all the acid azo dyes.
The visible absorption spectroscopic prope rties of the dyes were recorded in
DMF. The absorption m axima (λ ) of all the dyes falls in the range 422–465
max
nm in DMF, and the values are given in Table II. Th e values of the logarithm of
molar extinction coefficient (log ε) of all the dyes were in the range of 4.21–4.60,
consistent with their high absorption intensity. Moreover, the presence of elec -
tron donating or electron attracting groups did not bring about any marked in-
crease or decrease in λ
in the visible region and log ε remained nearly cons-
max
tant. However, an electron attracting substituent, suc h as –SO H, in the structure
3
of the coupler increases th e polarizability and will results in bathochromic shifts.
This leads to a decr ease in the energy between the highest occupied m olecular
orbital and lo west unoccupied molecular orbital and t hus the π → π* electronic
transition occurs with a lower frequency photon, resulting in a bathochromic shift
of the visible absorption band.
TABLE II. Absorption maxima in DMF (λmax), intensities (log ε), exhaustion (E) and fixation
(F) of acid mono azo dyes on wool and silk fabrics
Acid azo dyeing on wool
E / % F / %
80 89 72 90
Acid azo dyeing on silk
E / % F / %
Dye
λ
max / nm
log ε
D1
D2
D3
D4
D5
D6
D7
465
445
450
435
430
420
422
4.60
4.36
4.45
4.27
4.20
4.18
4.21
75 94 75 87
72 90 80 92
85 89 76 88
74 86 82 91
71 88 75 89
85 92 78 90
Dyeing properties of dyes
The acid mono azo dyes were applied at a 2 % depth on wool and silk fab-
rics. Their dyeing properties are shown in Tables III–VI. These dyes gave a wide
range of colours vary ing from pinkish blue to red shades with good levelness,
brightness and depth on the fabric s. The variation in the shades of the dye fabric
results from both the nature and position of the substituent present on the diazo-
tized compound. The dyeing showed excellent fastness to light, with a very good
to excellent washing, perspiration, rubbing and sublimation fastnesses.
A remarkable degree of s moothness after washing was observed. This m ay
be attributed to the good penetration into and affinity of the dye molecule for the
structure of the fabrics. The most prominent feature of these dyes is that the dy e
patterns treated with Cr(II I) salt solution afforded an excellent shining shade of
the dyes. This might be due to chrome complex formation on the fabric matrix.
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TABLE III. Results of acid mono azo dyeing and various fastness properties of dy es on wool
fabrics (grading: 5 – excellent, 4 – very good, 3 – good, 2 – fair, 1 – poor)
Perspiration
fastness
Acid Alkaline
Rubbing
fastness
Dry W et
Colour shades
on wool
Light Washing
fastness fastness
Sublimation
fastness
Dye
D1
D2
D3
D4
D5
D6
D7
Pinkish blue
Pinkish blue
Reddish brown
Yellowish pink
Chocolate brown
Red 5
5
5
5
4
4
5
4
5
5
4
5
4
4
5
5
4
5
5
5
5
4
5
5
5
5
5
4
4
5
4
4
5
4
4
4
5
4
5
4
5
4
4
4
3
4
3
4
Red 5
TABLE IV. Results of acid mono azo dy eing and various fastne ss properties of dy es on silk
fabrics (grading: 5 – excellent, 4 – very good, 3 – good, 2 – fair, 1 – poor)
Perspiration
fastness
Acid Alkaline
Rubbing
fastness
Dry W et
Colour shades
on silk
Light
fastness fastness
Wash
Sublimation
fastness
Dye
D1
D2
D3
D4
D5
D6
D7
Pinkish blue
Pinkish blue
Reddish brown
Yellowish pink
Chocolate brown
Red
5 4 4
5 4 5
4 4 4
4 4 4
5 5 4
5 4 4
5 4 4
5
4
5
4
4
4
4
5
4
5
4
4
5
5
4
4
4
4
5
4
5
3–4
3
4
3–4
4
4
Red
3–4
TABLE V. Re sults of mordent acid azo dy eing an d vario us fa stness pro perties of dy es on
wool fabrics (grading: 5 – excellent, 4 – very good, 3 – good, 2 – fair, 1 – poor)
Perspiration
fastness
Acid Alkaline
Rubbing
fastness
Dry W et
Colour shades
on wool
Light Washing
fastness fastness
Sublimation
fastness
Dye
D1
D2
D3
D4
D5
D6
D7
Pinkish blue
Pinkish blue
Reddish brown
Yellowish pink
Chocolate brown
Red 5
5
5
5
5
5
5
5
5
5
4
5
5
4
5
5
5
5
5
5
5
4
5
5
5
5
5
5
5
5
5
4
5
5
5
4
5
5
5
4
5
4
4
4
4
4
4
4
Red 5
The antibacterial activities of t he chrome co mplexes of the dyes ( D –D )
1
7
were monitored against the various pat hogens. The results (Table VII) showed
that the D , D and D dyes had moderate to high, D weak to moderate and the
1
3
7
6
other dyes weak activity against all the tested microorganisms. The dye pattern of
the chrome-treated dye may be tolerable for the human body.
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DYEING ASSESSMENT OF NOVEL ACID AZO DYES
613
TABLE VI. Results of mordent acid azo dyeing and various fastness properties of dyes on silk
(grading: 5 – excellent, 4 – very good, 3 – good, 2 – fair, 1 – poor)
Perspiration
fastness
Acid Alkaline
Rubbing
fastness
Dry W et
Colour shades
on silk
Light
fastness fastness
Wash
Sublimation
fastness
Dye
D1
D2
D3
D4
Pinkish blue
Pinkish blue
Reddish brown
Yellowish pink
5 5 5
5 5 5
5 4 5
5 5 5
5 5 5
5 5 5
5 5 5
5
5
5
5
5
5
4
5
5
5
4
4
5
5
5
4
4
5
5
4
5
4
4
4
5
4
4
4
D5 Chocolate brown
D6
D7
Red
Red
TABLE VII. Antibacterial activity of the acid azo chrome dyes (100 μg/mL)
Zone of inhibition, mm
Dye
E. coli
S. aureus
S. typhi
B. subtilis
D1
D2
D3
D4
D5
D6
D7
>21 16–20
11–15 11–15
>21 16–20
11–15 11–15
11–15 11–15
16–20 16–20
>21 >21
16–20
11–15
16–20
11–15
11–15
11–15
16–20
16–20
11–15
16–20
11–15
11–15
16–20
16–20
CONCLUSIONS
All newly synthesized acid mono azo dyes and mordent acid mono azo dyes
exhibited very good to excellent fastness to light, sublim ation, perspiration and
rubbing. The remarkable degree of levelness after dyeing indicates good penetra-
tion into, and affinity of these dy es for th e fabric matrix. They give deep and
bright hues with levelling dy eing. The na ture of the substituent in the coupl ing
component has little influence on the UV–visible absorption and shade of the
dyeing. A com parison of t he acid mono azo and the mordent acid azo dy es re-
vealed that the mordent acid mono azo dyes have better shades than the acid azo
dyes. Of the acid azo chrome dyes (D –D ), the dyes D , D and D showed mo-
1
7
1
3
7
derate to high antibacterial activity against all the tested microorganisms.
Acknowledgments. The authors are thankful t o the principal, V. P. & R. P. T. P. Science
College an d C. V. M. for pro viding the nece ssary research facilities. The authors are als
thankful to Mr. Ashok C. Kapadia and Mr. Pradeep N. Mistry of the Color Tax (Pvt) Ltd. ,
Surat, India, fo r characterizati on of the azo group and givi ng the stand ard of fastness pro-
perties and to Raju Mehta of G.P.C.B., Surat, India, for providing useful chemicals.
o
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2010 Copyright (CC) SCS

614DI
XIT et al.
И З В О Д
СИНТЕЗА, КАРАКТЕРИЗАЦИЈА И ИСПИТИВАЊЕ БОЈЕЊА ВУНЕНИХ И СВИЛЕНИХ
ТКАНИНА НОВИМ КИСЕЛИМ И МОЧИЛСКИМ АЗО БОЈАМА
НА БАЗИ 2-ХИДРОКСИ-4-МЕТОКСИБЕНЗОФЕНОНА
BHARAT C. DIXIT1, HITENDRA M. PATEL1, RITU B. DIXIT2 и DHIRUBHAI J. DESAI1
1Department of Chemistry, V. P. & R. P .T. P Science College, Vallabh Vidyanagar-388 120. Gujarat и 2Ashok
& Rita Patel Institute of Integrated Study & Research in Biotechnology and Allied Sciences,
New Vallabh Vidyanagar-388120, Gujarat State, India
Нове киселе и мочилске моноазо боје су синтетизоване купловањем диазонијумових
соли различитих ароматичних амина са 2-хидрокси-4-метоксибензофеноном. Добијене боје
су окарактерисане елементарном анализом, ИЦ, 1H-NMR и UV–Vis техникама. Својства
бојења су испитана на вуненим и свиленим тканинама. Бојење вунених и свилених тканина
претходно третираних хромом дало је боље обојење. Обојеност бојених вунених и свилених
тканина се кретала од плавичасто розе до црвене нијансе. Обојене тканине су показале веома
добру постојаност на светлост, прање, зној, сублимацију и трење. Резултати антибактериј-
ских испитивања својстава тканина претходно третираних хромом указала су на релативно
добру токсичност мочилских боја према Escherichia coli, Staphylococcus aureus, Salmonella
typhi и Bacillus subtilis.
(Примљено 4. јула 2009, ревидирано 21. јануара 2010)
REFERENCES
1. W. M. Cumming, G. J. Howie, J. Chem. Soc. (1933) 133
2. A. T. Peters, D. Walker, J. Chem. Soc. (1956) 429
3. A. I. Vogel, A Textbook of Practical Organic Chemistry, 3 rd ed., Long man, London,
1961, p. 620
4. P. F. Gordon, P. Gregory , Organic Chemistry in Colour, 1st ed., Springer-Verlag, Berlin,
1983, p. 60
5. S. K. Mohamed, A. M. Nour El-Din, J. Chem. Res. 8 (1999) 508
6. R. D. Naik, C. K. Desai, K. R. Desai, Orient. J. Chem. 16 (2000) 159
7. S. Yurteri, A. Onen, Y. Yagci, Eur. Polym. J. 38 (2002) 1845
8. W. Huang, B. Hou, Tribology Lett. 18 (2005) 445
9. E. Eltayeb, M. Barikani, A. R. Mahdavian, H. Honarkar, Iranian Polym. J. 18 (2009) 753
10. M. Johnson, R. G. Hauserman, J. Appl. Polym. Sci. 21 (1977) 3457
11. H. Kamogawa, M. Nanasawa, Y. Uehara, J. Polym. Sci. A 15 (1977) 675
12. K. Allmer, A. Hult, B. Ranby, J. Polym. Sci. 27 (1989) 3419
13. V. Frantisek, N. Hana, Czech patent: 176, 377 (1979) [CA 91:P58685x]
14. B. Raouf, US patent 4,066,388 (1978)
15. B. Brian, C. Donald, A. G. Sandoz, DE patent 3,417,782 (1984)
16. R. T. Markus, K. Jakob, Eur. Patent (EP) 169,808 (1986)
17. B. C. Dixit, H. M. Patel, D. J. Desai, J. Serb. Chem. Soc. 72 (2007) 119
18. B. C. Dixit, H. M. Patel, D. J. Desai, R. B. Dixit, E-J. Chem. 6 (2009) 315
19. H. E. Frirz-David, L. Blengy , Fundamental Process of Dye Chemistry, 3rd Ed., Wiley,
New York, 1949, p. 241
20. M. Szymczyk, A. E. Shafei, H. S. Freeman, Dyes Pigm. 72 (2007) 8
21. R. M. E. Shishtawy, Y. A. Youssef, N. S. E. Ahmed, A. A. Mousa, Dyes Pigm. 72 (2007) 57
22. M. J. Pelzar, E. C. S. Chan, N. R. Krieg, Antibiotics and Other Chemotherapeutic Agents
in Microbiology, 5th ed., Blackwell Science, New York, 1998.
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