A new way to improve the light-fastness of azo reactive dyes through the introduction of benzene sulfonamide derivatives into the triazine ring

Article abstract of DOI:10.1039/c9ra02108f

Herein, a new kind of hetero-bifunctional reactive dyes with high light-fastness was designed and synthesized by introducing benzene sulfonamide and its derivatives into the triazine ring. Benzene sulfonamide or its derivatives and 2-amino-5-naphthol-7-sulfonic acid (J-acid) were condensed with cyanuric chloride to synthesize coupling components, which were then coupled with the diazo salt of 4-(β-sulfatoethylsulfonyl)aniline. The dyes were characterized by IR spectroscopy and MS. The color fastness test proved that the light-fastness of the dyes could be improved by 1 grade via the introduction of benzene sulfonamide derivatives into the triazine ring when compared with the case of the control dyes. Fluorescence spectra demonstrated that after the introduction of benzene sulfonamide derivatives, the dye molecule could return to the ground state from the excited state and emit fluorescence; in addition, the introduced benzene sulfonamide derivatives helped to deteriorate the adverse effect of UV light on the dye. Moreover, the dyeing results showed that the dyes containing the sulfonamide groups had equal dyeing properties when compared with that of the control dyes.

Full text of DOI:10.1039/c9ra02108f

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A new way to improve the light-fastness of azo
reactive dyes through the introduction of benzene
sulfonamide derivatives into the triazine ring
Cite this: RSC Adv., 2019, 9, 17658
*
Xiong Wei, Ma Wei and Zhang Shufen
Herein, a new kind of hetero-bifunctional reactive dyes with high light-fastness was designed and
synthesized by introducing benzene sulfonamide and its derivatives into the triazine ring. Benzene
sulfonamide or its derivatives and 2-amino-5-naphthol-7-sulfonic acid (J-acid) were condensed with
cyanuric chloride to synthesize coupling components, which were then coupled with the diazo salt of 4-
(b-sulfatoethylsulfonyl)aniline. The dyes were characterized by IR spectroscopy and MS. The color
fastness test proved that the light-fastness of the dyes could be improved by 1 grade via the introduction
of benzene sulfonamide derivatives into the triazine ring when compared with the case of the control
dyes. Fluorescence spectra demonstrated that after the introduction of benzene sulfonamide derivatives,
the dye molecule could return to the ground state from the excited state and emit fluorescence; in
addition, the introduced benzene sulfonamide derivatives helped to deteriorate the adverse effect of UV
light on the dye. Moreover, the dyeing results showed that the dyes containing the sulfonamide groups
had equal dyeing properties when compared with that of the control dyes.
Received 19th March 2019
Accepted 21st May 2019
DOI: 10.1039/c9ra02108f
rsc.li/rsc-advances
usually introduced into a dye molecule by linkage with cyanuric
chloride,17 and the latter also acts as a reactive group in a reac-
Introduction
tive dye.
The photofading process of azo dyes occurs when the dye
Reactive dyes exhibit good wet-fastness because they form
chemical bonds with the textile bre.1,2 Since the average xa-
tion of mono-functional reactive dyes is below 65%,3,4 reactive
dyes are usually designed as bi-functional or multi-functional
structures to increase their utilization.5 Hetero-bifunctional
reactive dyes are widely used due to their good wet-fastness
under both acidic and alkali conditions.6,7
Due to its brilliant color, abundant hues, simple synthesis
procedures, excellent structure diversity and high molar
extinction coefficients, the azo chromophore has become the
most widely used chromophore. More than 80% of chromo-
phores used in reactive dyes are azo chromophores.8 However,
under natural conditions, the azo group will slowly decompose
in the presence of moisture, UV light, ozone, etc.9–12 With the
decomposition of the azo group, the light-fastness of the azo
dyes rapidly decreases. Therefore, the development of a strategy
to improve the light-fastness of azo dyes is of great importance
and current interest. Generally, there are two ways to improve
the light-fastness of azo dyes: rst, the use of chromophores,
such as anthraquinone and metal azo complexes, with high
light-fastness,13–15 and second, the incorporation of UV
absorbers into the dye molecules or the treatment of textiles
with UV absorbers before or aer dyeing.16–22 UV absorbers are
molecule is excited from the ground state to the excited state via
the absorption of a photon, and then, the dye molecule in the
excited state can react with oxygen,23–25 the return of the dye
molecule to the ground state from the excited state is favourable
for the light-fastness of azo dyes. The dye molecule can return to
the ground state from the excited state by emitting light; this
phenomenon is known as uorescence.
To date, no studies have been reported on the introduction
of a sulfonamide group directly into the s-triazine ring in the
dye industry to improve the light-fastness of azo dyes. Moreover,
signicant attention has been focused on the incorporation of
b-sulfatoethylsulfonyl aniline into dyes to improve the affinity
and xation of dyes;26,27 in previous studies, the sulfonamide
group has also been introduced into dyes as a linkage group to
replace benzidine since benzidine is highly carcinogenic and
mutagenic.28–32
Due to their simplest structure containing a sulfonamide
group, herein, benzene sulfonamide and its derivatives were
directly incorporated into the s-triazine ring with the aim to
obtain a new kind of reactive dyes with high light-fastness. The
new kinds of dyes were synthesized using 4-(b-sulfatoe-
thylsulfonyl) aniline as the diazo component. The coupling
component was synthesized by condensing cyanuric chloride
with benzene sulfonamide or its derivatives and 2-amino-5-
naphthol-7-sulfonic acid (J-acid). The inuence of benzene
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian
116012, P. R. China. E-mail: zhangshf@dlut.edu.cn; Fax: +86 411 84986264; Tel:
+86 411 84986265
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sulfonamide and its derivatives on the light-fastness has been 20 mL H2O at pH 6–7 by adding a sodium carbonate (10%, w/v)
discussed, and the dyeing properties have also been tested.
solution followed by cooling to 0–5 ꢀC. A solution of sodium
nitrite (0.72 g, 0.0105 mol) in H2O (5 mL) was then added to the
solution of 4-(b-sulfatoethylsulfonyl)aniline. The mixture was
then added to a cooled mixture of ice cubes and concentrated
hydrochloric acid (37%, 2.5 mL, 0.015 mol) under vigorous
stirring. The stirring was continued for 0.5 h at 0–5 ꢀC with
a positive test for nitrous acid. The excess nitrous acid was
decomposed by adding a small amount of sulfamic acid. The
diazo salt was used for the subsequent coupling reaction.
(3) Coupling reaction. The diazonium salt was slowly
added to the well-stirred condensation product solution
prepared previously at 5–10 ꢀC. The reaction pH was maintained
at 7–8 by adding a 10% (w/v) Na2CO3 solution, and stirring was
maintained for another 1 hour aer the solution was completely
added. At the completion of the coupling reaction, the dye was
salted out by adding potassium acetate, then ltered and
washed with ethanol to get dye 3a.
Experiment
Materials and instruments
2-Amino-5-naphthol-7-sulfonic acid (J-acid) and 4-(b-sulfatoe-
thylsulfonyl) aniline (para ester) were obtained from Zhejiang
Shunlong Chemical Co. Cyanuric chloride and benzene
sulfonamide and its derivatives were purchased from Aladdin
Industrial Corp. Aniline and sulfanilic acid were bought from
Tianjin Guangfu Chemical Reagent Co. All the other chemicals
involved in this study were of chemical grade. All the materials
were used without further purication.
The FTIR spectra were obtained via the JASCO 430 spec-
trometer (JASCO, Japan) using KBr pellets. The API-ES-Mass
spectra were obtained using the HP1100 mass spectrometer
(Hewlett-Packard, USA). UV-Vis spectra were obtained using the
HP-8453 UV-Visible spectrometer (Hewlett-Packard, USA).
Cotton dyeing was operated using an XW-PDR (Jinjiang Xin-
wang Dyeing & Finishing Machinery Factory). Fluorescence
spectra were acquired using the F-7000 uorescence spec-
trometer (HITACHI, Japan).
3a: yield: 83.1%. IR (KBr, cmꢁ1): 3448 (N–H, O–H), 2975 (C–
H), 1594 (N–H), 1545 (N]N), 1498 (triazine), 1390, 1137 (SO2–
NH), 1195, 1083 (–SO3H). M/S (ES-API): m/z ¼ 798.9, found 798.0
([M ꢁ H]ꢁ), 398.5 ([M ꢁ 2H]2ꢁ/2).
The dyes 3b–g were synthesized via the same way by simply
changing the condensation reactant.
Dye 3b was synthesized by replacing benzene sulfonamide
with 4-sulfamoyl benzoic acid. Yield: 103.4%. IR (KBr, cmꢁ1):
3429 (N–H, O–H), 2975 (C–H), 1596 (N–H), 1561 (N]N), 1499
(triazine), 1453 (O–H), 1385, 1137 (SO2–NH), 1257, 1051
(–SO3H). M/S (ES-API): m/z ¼ 842.98, found 842.0 ([M ꢁ H]ꢁ),
420.6 ([M ꢁ 2H]2ꢁ/2).
Synthesis of dyes
The synthesis of the mono-azo reactive dyes 3a–i based on J-acid
with the substitution of benzene sulfonamide or its derivatives
is depicted in Scheme 1. The synthetic procedure of the dye 3a is
described as below.
(1) Condensation. Cyanuric chloride (1.84 g, 0.01 mol,
dissolved in 20 mL acetone) was dropped to a cooled mixture of
benzene sulfonamide (3.14 g, 0.02 mol), 0.02 mol NaOH and
20 mL H2O. The dropping procedure lasted for about 0.5–1 hour
at 0–5 ꢀC. The condensation reaction mixture was stirred for
another 1 hour until no cyanuric chloride was detected. More-
over, the excess benzene sulfonamide was ltered aer being
acidied with the condensation product by adjusting its pH to
lower than 3 using hydrochloric acid. The ltrate was then
added to a well-stirred solution of J-acid (2.39 g, 0.01 mol, dis-
solved in 40 mL H2O at pH 6–7). The reaction was stirred for
Dye 3c was obtained by replacing benzene sulfonamide with
4-toluene sulfonamide. Yield: 88.6%. IR (KBr, cmꢁ1): 3463 (N–
H, O–H), 2978 (C–H), 1595 (N–H), 1556 (N]N), 1498 (triazine),
1451, 1390 (C–H), 1320, 1137 (SO2–NH), 1221, 1052 (–SO3H). M/
S (ES-API): m/z ¼ 813.0, found 811.8 ([M ꢁ H]ꢁ), 405.5 ([M ꢁ
2H]2ꢁ/2).
Dye 3d was synthesized by replacing benzene sulfonamide
with 4-triuoromethyl benzene sulfonamide. Yield: 72.2%. IR
(KBr, cmꢁ1): 3444 (N–H, O–H), 2976 (C–H), 1595 (N–H), 1543
(N]N), 1499 (triazine), 1324, 1189, 1168 (Ar–CF3), 1390, 1136
(SO2–NH), 1225, 1051 (–SO3H). M/S (ES-API): m/z ¼ 866.9, found
865.9 ([M ꢁ H]ꢁ), 432.5 ([M ꢁ 2H]2ꢁ/2).
ꢀ
another 3 hours at 25 C and pH 6–7. The reaction was moni-
tored by thin layer chromatography (eluent: n-butanol/
isopropanol/ethyl acetate/H2O ¼ 2/4/1/3, v/v). The condensa-
tion product was used for the subsequent coupling reaction.
(2) Diazotization of 4-(b-sulfatoethylsulfonyl)aniline. Typi-
cally, 0.01 mol 4-(b-sulfatoethylsulfonyl)aniline was dissolved in
Dye 3e was obtained by replacing benzene sulfonamide with
4-nitrobenzene sulfonamide. Yield: 77.5%. IR (KBr, cmꢁ1): 3442
(N–H, O–H), 2975 (C–H), 1594 (N–H), 1564 (N]N), 1529, 1355
(–NO2), 1498 (triazine), 1385, 1138 (SO2–NH), 1226, 1052
(–SO3H). M/S (ES-API): m/z ¼ 843.9, found 842.9 ([M ꢁ H]ꢁ),
421.0 ([M ꢁ 2H]2ꢁ/2).
Dye 3f was synthesized by replacing benzene sulfonamide
with 4-chlorobenzene sulfonamide. Yield: 89.6%. IR
(KBr, cmꢁ1): 3406 (N–H, O–H), 2978 (C–H), 1595 (N–H), 1542
(N]N), 1498 (triazine), 1386, 1136 (SO2–NH), 1257, 1050
(–SO3H), 1087 (Ar–Cl). M/S (ES-API): m/z ¼ 832.9, found 831.8
([M ꢁ H]ꢁ), 415.5 ([M ꢁ 2H]2ꢁ/2).
Dye 3g was obtained by replacing benzene sulfonamide with
4-bromobenzene sulfonamide. Yield: 99.4%. IR (KBr, cmꢁ1):
3422 (N–H, O–H), 2975 (C–H), 1595 (N–H), 1564 (N]N), 1498
Scheme 1 Synthesis procedure of the reactive dyes 3a–i.
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(triazine), 1388, 1137 (SO2–NH), 1221, 1051 (–SO3H), 1078 (Ar–
Br). M/S (ES-API): m/z ¼ 876.9, found 437.5 ([M ꢁ 2H]2ꢁ/2).
Color fastness measurement
The wash fastness was assessed using a 5 g Lꢁ1 standard soap
ꢀ
solution at 40 C for 30 min according to GB/T 3921-2008. The
rub fastness was tested according to GB/T 3920-2008 using
a Y(B)571-II crockmeter (Darong Standard Textile Apparatus Co.
Ltd., Wenzhou). The light-fastness was tested according to GB/T
8427-2008 using YG(B)611-V light-fastness tester (Darong Stan-
dard Textile Apparatus Co. Ltd. Wenzhou). The K/S value was
measured by using a Ultrascan XE Color Measuring and
Matching Meter (Hunter Co. UK).
Synthesis of control dyes 3h–i
The synthesis procedure for control dye 3h is described below.
Cyanuric chloride (1.92 g, 0.0105 mol) and 20 g of ice cubes
were stirred for 30 minutes at 0–5 ꢀC. The rst condensation
reaction was started by adding aniline (0.93 g, 0.01 mol) at the
temperature of 0–5 ꢀC for 2 hours. Then, the condensation
mixture was added to J-acid (2.39 g, 0.01 mol) at the temperature
of 30 ꢀC and pH of 6–7. The reaction was monitored by TLC
(eluent: n-butanol/isopropanol/ethyl acetate/H2O ¼ 2/4/1/3; v/v).
The diazotization and coupling process were the same as those
of dye 3a.
Results and discussion
Dye synthesis
3h: yield: 84.4%. IR (KBr, cmꢁ1): 3397 (N–H, O–H), 2976 (C– In this study, dyes based on J-acid were synthesized, as depicted
H), 1599 (N–H), 1575 (N]N), 1496 (triazine), 1298 (C–N), 1255 in Scheme 1. Benzene sulfonamide derivatives were condensed
(C–O), 1227, 1049 (–SO3H). M/S (ES-API): m/z ¼ 735.03, found with cyanuric chloride to obtain a new kind of reactive dyes with
734.0 ([M ꢁ H]ꢁ), 366.5 ([M ꢁ 2H]2ꢁ/2).
high light-fastness.
3i was synthesized using sulfanilic acid instead of aniline.
Yield: 82.0%. IR (KBr, cmꢁ1): 3443 (N–H, O–H), 2973 (C–H),
1596 (N–H), 1557 (N]N), 1495 (triazine), 1370 (C–N), 1222, 1050
Synthesis of the reactive dyes 3a–i
(–SO3H). M/S (ES-API): m/z ¼ 814.98, found 406.5 ([M ꢁ 2H]2ꢁ
/
The reactants R–NH2 and J-acid were condensed with cyanuric
chloride, and then, the obtained product was coupled with
a para ester diazo salt to synthesize the dyes 3a–i, as depicted in
Scheme 1. Benzene sulfonamide and its derivatives were used to
synthesize the dyes 3a–g containing sulfonamide groups. Dyes
substituted with the anilino and 4-sulfonato phenyl groups were
used to synthesize the control dyes 3h–i.
The visible spectra of the dyes 3a–i are shown in Fig. 2. As
shown in Fig. 2, the dyes 3a–i exhibit same absorption feature in
the visible light region due to the presence of same chromo-
phore based on J-acid. All the dyes showed a broad absorption
band from 400 to 550 nm, with the maximum absorption
wavelength of about 480 nm.
2).
Dyeing process
The dyes 3a–i were applied to the dyeing cotton at 1–2% owf
color shade to achieve dyeing cotton with a similar K/S value at
Na2SO4 of 100 g Lꢁ1 (added in three times) and Na2CO3 of 10 g
Lꢁ1 under the xation of 75 C. The liquor-to-goods ratio was
ꢀ
10 : 1. Aer dyeing, the colored cotton was washed thoroughly;
then, the dyeing cotton was soaped in a 2 g Lꢁ1 OP-10 solution
ꢀ
at 95 C for 10 min and nally washed and dried. The dyeing
process was conducted as descripted in Fig. 1.
The exhaustion, xation and reactivity of the dyes were
calculated using eqn (1)–(3), and the absorbance was deter-
mined using the HP 8453 UV-Vis spectrophotometer at the lmax
of each dye.
The structural and UV-Vis absorption information of 3a–i are
listed in Table 1. The molar absorption coefficients range from
19 103 L molꢁ1 cmꢁ1 to 27 079 L molꢁ1 cmꢁ1. Dyes substituted
with benzene sulfonamide and its derivatives have higher molar
E ¼ (A0 ꢁ A1)/A0 ꢂ 100%
F ¼ (A0 ꢁ A1 ꢁ A2)/A0 ꢂ 100%
R ¼ E/F ꢂ 100%
(1)
(2)
(3)
where A0, A1 and A2 respectively represent the absorbance of the
original dyeing solution, the dyeing waste solution and the
soaped solution.
Fig. 1 Dyeing procedure of the synthesized dyes.
17660 | RSC Adv., 2019, 9, 17658–17663
Fig. 2 Visible spectra of the dyes 3a–i.
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Table 1 Structure, solubility and spectral data of the dyes 3a–i based Table 2 Dyeing results of the dyes 3a–i
on J-acid
Dye
E%
F%
R%
lmax
(nm, H2O) 3 (L molꢁ1 cmꢁ1) (H2O)
S (g Lꢁ1
)
3a
3b
3c
3d
3e
3f
3g
3h
3i
98.7
86.7
96.0
98.1
93.9
96.5
98.4
95.7
95.1
86.4
72.0
82.9
84.2
79.9
79.7
86.1
87.7
87.3
87.6
83.1
86.3
85.8
85.0
82.6
87.5
91.7
91.8
Dye
R
3a
3b
3c
3d
140.52
226.94
96.16
478
479
478
479
21 185
21 880
22 598
25 037
154.36
sulfonamide and its derivatives. Moreover, Fig. 3 displays the
images of the dyeing cotton. As shown in Fig. 3, the dyes 3a–i
provide the same orange color, and all the dyeing cotton
samples show good color uniformity.
3e
3f
222.58
66.98
478
479
27 079
25 958
In Table 2, we can see that the exhaustion of the dyes 3a and
3h was 98.7% and 95.7%, and the xation was 86.4% and
87.7%, respectively. The exhaustion and xation of the dyes 3a
and 3h were almost the same. The difference in the structures of
the dyes 3a and 3i originated due to the substitution of the
sulfonamide group; however, similar dyeing properties ob-
tained at 75 ꢀC indicated that the introduction of the sulfon-
amide group had a slight inuence on the dyeing properties.
Using another soluble group in the dye molecule, the solubility
of the dyes 3b and 3i was found to be signicantly higher than
that of those without the soluble group. Owing to the high
solubility of dye 3b (up to 226.94 g Lꢁ1), its exhaustion was only
86.7%, which was lower than that of the other dyes. Moreover,
the presence of the carboxyl group in 3b in the form of –COOꢁ
would increase the electrostatic repulsion between the dyes and
the cotton bers. Although it was substituted with another
water-soluble group, the dye 3i still maintained the high
exhaustion of 95.1%, which was attributed to its low solubility
and high substantivity. The xation of the dye 3b was 72.0%,
which was lower than that of the dye 3i (87.3%). The xation
difference between 3b and 3i was due to the increase in steric
hindrance during the xation reaction caused by the introduc-
tion of the sulfonamide group.
3g
3h
67.68
20.20
479
479
23 355
19 103
3i
163.18
479
19 947
absorption coefficients than the control dyes 3h–i. When
different substitution groups were incorporated into the dye
molecules, the solubility of the dyes 3a–i signicantly differed.
The dye 3h substituted with aniline exhibited the lowest solu-
bility of 20.20 g Lꢁ1. When another water-soluble group,
carboxyl group, was substituted into the dye molecule, 3b
exhibited the highest solubility of 226.94 g Lꢁ1 among all the
dyes.
The incorporation of benzene sulfonamide and its deriva-
tives had a positive effect on the dye solubility; the improved
solubility most probably originated due to the increase in
molecular polarity, which could help reduce the formation of
dye clusters; on the other hand, the increased molecular
polarity originated due to the deterioration of molecular
planarity, which resulted from the introduction of the sulfon-
amide group.
Dyeing properties
The dyeing process was conducted as shown in Fig. 1. The dyes
3a–i were applied to the dyeing cotton at 1–2% omf to achieve
the close K/S values of about 15.5–16.5. To reduce the hydrolysis
of vinyl sulfonate and enhance the reactivity of the mono-
chlorotriazine reactive group, the xation temperature was set
ꢀ
at 75 C.
Dyeing results
The dyeing results for 3a–i are provided in Table 2. To compare
the inuence of the sulfonamide group on the dyeing properties
of different dyes, the control dyes 3h and 3i without the
substitution of the sulfonamide group were designed and
compared with the dyes 3a–g substituted with benzene Fig. 3 Images of the cotton dyed with the dyes 3a–i.
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For the dyes 3c–g with different substitution groups on the
benzene sulfonamide residue, the solubility differed from 66.98
to 222.58 g Lꢁ1. However, no obvious difference in their
exhaustion and xation was observed; this implied that the
substitution groups on the benzene sulfonamide had no
essential inuence on the dye exhaustion and xation. The
steric hindrance caused by the incorporation of sulfonamide
made the reaction between the reactive dyes and cotton difficult
to occur; this led to a decrease in the xation of the dyes 3c–g.
Color fastness of the dyes
The color fastness of the dyes with similar K/S values on cotton
was tested and is presented in Table 3. Since the covalent bonds
formed between the dyes and cotton are the same, the rub-
fastness and wash-fastness of the dyes involved in this study
should be the same. However, because of higher water solubility
of dyes due to the introduction of benzene sulfonamide or its
derivatives, the color fastness test showed that the rub-fastness
and wash-fastness of the dyes 3a–g containing benzene
sulfonamide and its derivatives were slightly better than those
of the control dyes 3h and 3i. The high water-solubility provided
the dyes with a good wash-off property, which was favourable to
improve the wet-fastness and rub-fastness. Moreover, the light-
fastness values of the dyes 3b–g containing benzene sulfon-
amide derivatives were 4–5 grade, which were 1 grade higher
than those of the dye 3a and the control dyes 3h and 3i. The
difference in the light-fastness could be explained by the
difference in their uorescence spectra.
The uorescence emission spectra of the dyes 3a–g and
control dyes 3h and 3i were obtained, as displayed in Fig. 4. All
the dyes have been tested at the concentration of 2 g Lꢁ1, which
is about the dyeing concentration. Moreover, the uorescence
intensity of the system has been determined from 350 to 575 nm
with the excitation wavelength of 300 nm since all the dyes show
their maxima absorption around 300 nm in the UV region.
From Fig. 4, we can conclude that aer the substitution of
the benzene sulfonamide derivatives, the dyes 3b–g show weak
uorescence emission characteristics, which can help the dye
molecule in the excited state to return to the ground state by
emitting uorescence; in addition, the dye 3a shows weaker
uorescence than the dyes 3b–g; this weakens the effective
Fig. 4 Fluorescence spectra of the dyes 3a–i.
energy transfer of the dye 3a. Moreover, no uorescence was
observed for the dyes 3h and 3i; this illustrated that the dyes 3h
and 3i could not return to the ground state from the excited
state by emitting uorescence. Therefore, the differences in the
light-fastness of the dyes 3a–i were most possibly caused by the
differences in their uorescence spectra.
Conclusions
Herein, benzene sulfonamide and its derivatives were
condensed with cyanuric chloride to synthesize a new series of
hetero-bifunctional azo dyes; this new kind of dyes was
synthesized using 4-(b-sulfatoethylsulfonyl) aniline as the diazo
component, and the coupling component was synthesized by
condensing cyanuric chloride with benzene sulfonamide or its
derivatives and J-acid. According to the fastness test, dyes
substituted with benzene sulfonamide derivatives displayed
better light fastness than the control dyes, which was about 1
grade higher than that of the control dyes. Moreover, the uo-
rescence spectra showed that aer the introduction of the
sulfonamide group, the dyes showed weak uorescence, which
could help transfer the UV light. Via the transfer of the absorbed
UV light, the destructiveness of the UV light to azo dyes was
weakened. Moreover, the dyeing results showed that the
incorporation of the sulfonamide group had a little inuence on
the exhaustion of the dyes; however, the xation of the dyes
decreased as the reaction between the reactive dyes and cotton
became difficult to occur due to the increase in the steric
hindrance caused by the introduction of sulfonamide groups.
Table 3 Color fastness of dyes 3a–i on cotton
Rub-
fastness
Wet-fastness
Entry K/S
Light-fastness Dry Wet Change Cotton Wool
Conflicts of interest
3a
3b
3c
3d
3e
3f
3g
3h
3i
15.66 3–4
4–5
4
4
4–5
4–5
4–5
4–5
4
4
4
4
4
4
4
4
4–5
4
4
4
4
4
4–5
4
4
4
4
4
4–5
4–5
4–5
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4–5
4–5
4–5
4–5
4–5
16.56 4–5
16.61 4–5
16.65 4–5
15.61 4–5
16.18 4–5
16.11 4–5
15.58 3–4
15.98 3–4
All authors declare that there are no conicts of interest.
4
4–5
4–5
4–5
Acknowledgements
This work was supported by the National Key R&D Program of
China (2017YFB0307401), the Science Fund for Creative
3–4 4–5
4
4–5
4
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Research Groups of the National Natural Science Foundation of 15 A. D. Towns, Dyes Pigm., 1999, 42, 3–28.
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University of Technology (Dalian University of Technology 17 R. Rajagopal and S. Seshadri, Dyes Pigm., 1988, 9, 233–241.
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19 E. Yousif and R. Haddad, SpringerPlus, 2013, 2, 398.
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M. Bonet, J. Ind. Text., 2016, 45, 2–12.
21 Y. Tang, P. Gao, M. Wang, J. Zhu and X. Wan, RSC Adv., 2014,
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