Journal of Molecular Liquids xxx (2017) xxx-xxx

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Journal of Molecular Liquids

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journal homepage: www.elsevier.com

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Relationship between structures and dyeing properties of reactive dyes for cotton
dyeing
Umme Habibah Siddiquaa, Shaukat Alia, Munawar Iqbalb, ⁎, Tanveer Hussainc

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a
Department of Chemistry, University of Agriculture, Faisalabad, Pakistan
b
Department of Chemistry, The University of Lahore, Lahore, Pakistan
c
Department of Textile Chemistry, National Textile University, Faisalabad, Pakistan

ARTICLE INFO ABSTRACT

Article history: Heterofunctional reactive dyes were studied for their dye fixation and colour strength on to cotton fiber. Re-
Received 7 February 2017

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active dyes with different reactive groups (monochlorotriazine and sulphatoethylsulphone) were applied on to
Accepted 15 April 2017 cotton fabric with pad thermofix method to explore the role of functional group on colour strength and fast-
Available online xxx
ness properties. Dye fixation and colour strength of cotton fabric revealed that dye with different functional
groups have different reactivity and affinity to the cotton fiber. Reactive dyes exhibited high colour strength at
Keywords:
Heterofunctional reactive dyes
Dye structure
Cotton fiber
Dyeing properties
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optimum conditions of temperature, pH and reaction time. Among dyes under investigation, D-6 (ester vinyl-
sulphone at Para position) showed the highest colour strength (82%) and D-2 (ester vinylsulphone at Meta
position) furnished minimum colour strength of 67%. The dyes having linear and planar structure offer higher
reactivity. The fastness properties of cotton fiber for all reactive dyes were good to excellent in comparison to
commercial Reactive Red 195 dye.
Fastness properties
© 2016 Published by Elsevier Ltd.
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1. Introduction tinuous dyeing process, a significant amount of exhausting agents are
utilized (40–100 g/L) for better dye exhaustion to overcome dye–fiber
There is a growing trend to synthesize and employ new analogues repulsion. In spite of various advantages of pad dyeing method, nev-
of synthetic colorants for enhance dyes exhaustion to meet the de- ertheless, complete dye exhaustion is achieved and up to 15% dyes
sired colour strength (K/S), which can precludes the dye waste due are lost during dyeing process and have adverse effect on the of envi-
to low dye fixation. Reactive dyes are the most widely used class of ronmental safety [46,47]. The hydrolysis in dyeing bath attributes to
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dyes due to their comparatively better fastness properties and their the lower dye-fixation and is one of the main drawbacks of continuous
ease of applications [1,2]. The good fastness properties are attrib- dyeing method [48].
uted to the chemical linkage of dyes (functional group) with the cel- Therefore, to ensure sustainable environmental development, the
lulosic fiber [3]. It has been observed that nature of fabric, medium discharge of dyes in wastewater should be reduced to maximum level
pH, reaction time, dyeing methodology, chemical auxiliaries, dyeing [13,47], which demands the optimization of process variable along
temperature and nature of dye have significant role on dye fixation with suitable dyes section. The dyeing method, dye type, dye concen-
and colour strength [4–8]. The functional group (nature and number) tration, temperature, reaction time, medium pH and salt amount used
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present in the structure of reactive dye molecule has distinct influ- during dyeing affect the dye fixation. Moreover, dye structure (num-
ence on dyeing behavior. Dyes containing monochlorotriazine (MCT) ber of functional group and their position) are also important in con-
and sulphatoethylsulphone (SES) moieties showed higher fixation ef- trolling the dye fixation [49,50].
ficiency versus dyes containing only one type of reactive group (i.e., In the present investigation, six reactive dyes having different
a vinyl sulfone precursor, moieties which bond to the fiber in alka- functional group (number and positions) were selected and employed
line medium by means of nucleophilic substitution and Michael addi- on cotton fabric. The dyeing was performed by pad/thermosol method.
tion) [9]. Therefore, to enhance the dye fixation and colour strength, Various process variables were optimized to enhance to colour
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it is important to optimize the dyeing conditions since these affect the strength and dyeing fastness properties and responses were compared
dyeing [10–12]. The low fixation of dyes cause environmental issue with commercial Reactive Red 195 dye.
since dyes lost in dyeing process contaminate the water sheds and are
toxic to living organisms [13,14]. On the other hand, under the cur- 2. Materials and methods
rent scenario of environmental condition [15–45], there is a need to
use reactive dyes and to optimize the dyeing condition. During con 2.1. Materials

For dyeing bleached and mercerized cotton fabric (plain weave

⁎
Corresponding author. with areal density of 97.8 g/m2) was obtained from Aziz Fatima tex
Email address: bosalvee@yaho.com (M. Iqbal)

http://dx.doi.org/10.1016/j.molliq.2017.04.057
0167-7322/© 2016 Published by Elsevier Ltd.
2 Journal of Molecular Liquids xxx (2017) xxx-xxx

tile limited, Faisalabad. The dyes used for cotton dyeing are given in rinated water and perspiration testing ISO 105-X12 (1987), ISO
Table 1, which as abbreviated as D-1 to D-6. The λmax of dyes were 105-B02 (1988), ISO 105-C02, ISO 105-E03 and ISO 105-E04 (1989)
measured by CE Cecil 7200, UK spectrophotometer. Padder machine were used, respectively [53].
model (MH-1-Tsujii Dyeing Machine Mfg. Co. Ltd. Osaka/Japan)
was used for dyeing process of cotton fiber. Ultra-pure water with 3. Results and discussion

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a resistivity of 18.2 MΩ cm from Milli-Q® system (Millipore) was
used throughout the study. NaOH (97%)/HCl (36.5%) 0.1 M solution 3.1. Effect of temperature
was used for pH adjustment and detergent used for washing were pur-

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chased from Sigma-Aldrich. The dyeing process influenced under variable temperature since
temperature affects physico-chemical properties. Temperature effect
2.2. Dyeing procedure was studied in the range of 140, 150 and 160 °C, while other para-
meters were constant and responses revealed that temperature affected
Bleached and mercerized cotton fabric was subjected to padding the dyes exhaustion significantly (Fig. 1). Dye D-1 and D-2 showed
dyeing using 2% dye solutions. For dyeing, material to liquor ratio of maximum colour strength at 160 °C (same reactive groups are pre-
25:1 was used. The pressure on the mangle being controlled to give sent in both dyes), whereas D-3 to D-6 furnished higher strength at

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80% pick-up and different conditions for the optimization of the dye- 150 °C (have one monochlorotriazine and two vinylsulphone reactive
ing parameters were studied i.e., temperature (150, 160, and 170 °C), groups). Maximum colour strength of 80% was observed for D-6 at
dyeing time (1, 1.5, and 2 min) and pH (9, 10 and 11). 150 °C, whereas D-2 revealed minimum colour strength of 40% at
The cotton fiber after dyeing was washed with 2 g/L detergent so- 140 °C. It is observed that at low temperature, the dyes exhaustion was
lution and then, washed with warm and cold water to remove the low, which increased by increasing the dyeing temperature. The op-
un-reactive dye. The percentage absorbance was measured on spec- timum temperature for dyes D-3 to D-6 was 150 °C and D-1 to D-2
traflash spectrophotometer [51]. showed better response at 160 °C. It is reported that the dyes exhaus-
The dye percentage fixation ratio was calculated considering K/S tion can be improved at higher temperature and are generally higher

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values before and after washing of the dyed samples. The K/S values temperature is recommended for to obtain better penetration and fix-
were evaluated at λmax using spectraflash spectrophotometer and dye ation of dye [54]. Dye having similar functional groups gave better
fixation was measured as shown in Eq. 1 [52]. response at one temperature and as the functional groups changed,
the temperature sensitivity of dyes also changed, which revealed that

where, (K/S)1 and (K/S)2 are the colour strengths of the dyed cotton
TE(1)
functional groups in dyes structure are sensitive to temperature and
they may respond differentially under variable temperature values. It
is well known that temperature other than the optimum value might af-
fect the dye exhaustion. At higher temperature, desorption of already
before and after washing, respectively. absorbed dye may occur since hydrolytic degradation of dye may oc-
International Organization for Standardization (ISO) methods used cur in aqueous media [55,56]. The low colour strength at lower tem-
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for colour fastness testing i.e., for rubbing, light, washing, chlo perature was due to aggregation of dye molecule and preclusion of
dyes to fix on fiber [57,58].

3.2. Effect of pH
Table 1
Structures of the reactive dyes, showing functional group positions and dye codes (D-1 pH of the medium is one of main factors in the dyeing process and
to D-5).
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reactive dyes are more sensitive to pH. The pH (acidic/basic) affect

Dye Reactive Group
No. positions Dye Structures

D-1 Para ester

Vinylsulphone
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D-2 Meta ester

Vinylsulphone

D-3 Meta and Para

ester
Vinylsulphone
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D-4 Meta and meta

ester
Vinylsulphone

D-5 Para and Meta

ester
Vinylsulphone

D-6 Para and Para

ester
Vinylsulphone Fig. 1. Effect of dyeing temperature (140–160 °C) on colour strength (%) of six reactive
dyes.
 Journal of Molecular Liquids xxx (2017) xxx-xxx 3

the dyeing characteristics of both dyes and substrate [54,59–63]. Tri-

azine and vinylsulphone have reactive components to interact with
cellulose fibers [64]. Hydroxyl group (cellulose) in alkaline pH inter-
acts with electron deficient carbon attached to the chloro group and
high temperature required to replace the third group and to establish

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covalent linkage. Similarly, reactive dyes get activated under alkaline
pH at high temperature to produce the reactive form of vinylsulfone,
which interacts with O-nucleophile in the cellulosic fabrics and resul-

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tantly, a covalent bond is established via Michael addition mechanism
[65]. In view of analyzing the influence of the reactive group chem-
istry as a function of pH, dyeing was carried out at different pH's (9, 10
and 11). The dyes maximum exhaustion was at pH 10 (Fig. 2), which
may be ascribed to low hydrolysis of dyes at pH 10. At lower pH cot-
ton substrate offer low degree of deprotonation and at higher pH, the
dye may be hydrolysed and resultantly, colour strength was reduced.

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Chen et al. [66] also studied the effect of pH on the reactive dyes dye-
ing behavior and pH 10 was found to be optimum.

3.3. Effect of dyeing time Fig. 3. Effect of dyeing time (1–2 min) on colour strength (%) of six reactive dyes.

In dyeing process, surface adsorption, diffusion and dye-fabric fix- 3.4. Dye structure and colour strength relationship
ation of dye is involved [67]. This dyeing process reached at an equi-

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librium stage for specific reaction time and at that specific time, the The structure of the dye molecule plays an important role in the
sorption and desorption equilibrium is reached. However, prolonged affinity of the dye for the fiber [69–71]. The hetero-functional re-
dyeing time at higher temperature would facilitate dye desorption active present in dye structures have more affinity for the cellulosic
more efficiently [58]. The hydrolysis of dye is one of main factors, fibers [51]. Dye structure linearity, coplanarity and presence of the
which desorbs the dye molecule at unfavorable condition. The dyeing
behavior of dyes under investigation, as a function of time is shown
Fig. 3. The results revealed 2 min dyeing time yielded higher colour
strength with smooth shade for all the dyes. D-6 showed maximum
TE conjugated double bonds are the general factors in achieving higher
dye fixation [72]. In this connection, the colour strength and dye
structure relationship was studied and results are shown in Fig. 4.
The dyes (D-1 and D-2) having heterobifunctional reactive groups
colour strength, while D-2 colour strength was least. However, all showed low colour strength versus heterotrifunctional reactive groups.
dyes (D-1 to D-6) furnished colour excellent colour strength for 1.5 to It is well know that functional groups interact with substrate, and
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2 min reaction time and these findings are in line with reported results the colour strength was observed for dyes having different functional
of heterofunctional reactive dyes that dyeing time is effective for re- groups (D-3 to D-6) showed significantly different colour strengths.
active dyes. The reactive dyes fixation can be achieved in very short Both dye D-1 and D-2 (two reactive groups) furnished low colour
duration at optimize conditions of temperature and pH [68]. strengths. Moreover, the position of reactive group is also impor-
tant. The dye D-2 showed low colour strength and D-6 colour
RR
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Fig. 2. Effect of dyeing pH (9–11) on colour strength (%) of six reactive dyes.
Fig. 4. Comparison of the colour strength (%) of six reactive dyes on cotton fiber dyed
by pad thermofix method.
4 Journal of Molecular Liquids xxx (2017) xxx-xxx

strength was higher. In case of D-2 dye, the vinylsulphone reac- Table 3
tive group was at the Meta position which likely to offer the diffi- Fastness properties of the cotton dyed with six reactive dyes and commercial dye (Re-
active Red 195).
dent coplanarity, whereas in case of D-6 dye, vinylsulphone reactive
groups were at the Para position making the geometry of the mol- Dye D-1 D-2 D-3 D-4 D-5 D-6 RR 195
ecule more planar, linear and less hindered [73]. It is observed that

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Washing fastness 5 4 4–5 5 5 4–5 4–5
the different colour strength was mainly due to the dye structure and Rubbing fastness 4 4 4 4 4–5 4–5 4–5
the number of reactive groups and their positions. The dyes D-3, D-4, Light fastness 4–5 4–5 5 5 5 5 5
D-5 and D-6 dyes have similar chromophore, number of the reac- Perspiration fastness 4 4 4–5 5 4–5 5 4–5

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tive groups and linking group, but surprisingly difference in colour Chlorinated fastness 3–2 3–2 3–4 3 3 3 3
strengths can be correlated with reactive group positions. In case of RR 195 = Reactive Red 195.
D-3 and D-5, one vinylsulphone reactive group was present at the
Meta position and other at the Para position, while in case of D-4 and
D-6 both reactive groups are present at the Meta positions and Para effect of washing agents (soaps and detergents). The washing fast-
positions, respectively. So far, dyes having same functional groups at ness showed that dyed cotton fiber furnished good to excellent wash-
different position showed different colour strengths. ing fastness. The washing fastness was comparable with reactive red
195. The good washing fastness of the reactive dyes may be due to the

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3.5. Comparison of Colorimetric data chemical fixation of the dye molecules [74]. Colour fastness to rub-
bing is also considering a crucial parameter. Rubbing fastness evalu-
Colorimetric data of the cotton fabric dyed with the dyes (having ates the ratio of colour which may transfer from the surface of a col-
different number and positions of function groups) were compared and ored fabric to an uncolored bleached test cloth during the systematic
results are shown in Table 2. The Colorimetric data of dyes under in- rubbing practice. All dyes furnished good rubbing fastness. The D-1
vestigation was compared with commercial dye reactive red 195. The to D-4 rubbing fastness values were 4, whereas D-5 to D-6 and re-
cotton fiber sowed bright shade (high C* value), which indicates that active red 195 showed the values in the range of 4–5. Results of the
rubbing fastness revealed good penetration and fixation of the dyes.

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dye uptake was excellent since C* value was comparable with com-
mercial dye. The dye D-3, D-4, D-5, D-6 furnished dark shades (low Light fastness is the resistance of dyed fiber to fade upon exposure
L* value) with redder tone (higher a* values) versus standard dye. On to light. Different dyes have varying susceptibilities to light exposure.
the other hand, D1 and D2 dyes showed lighter (high L* value) and Light fastness of all dyes was also high (4–5), which was 5 for reactive
blurred shades (higher–b* values) in comparison to standard dye (re-
active red 195).

3.6. Comparison of fastness properties

TE red 195. The stability of the chromophore to sunlight is greater for the
azo dyes containing H-acid because chromophoric group undergoes to
the azo-hydrazone tautomerism that might responsible for stability to
photo-effect (Fig. 5). The strong covalent bond between the dye and
fiber seems to have facilitated the transfer of energy from the excited
Standard grey scale was used for the assessment of the staining and dye molecule to the fiber increasing the stability of the reactive dyes
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responses (fastness properties) are shown in Table 3. Washing fast- under light exposure [75]. Perspiration and chlorinated fastness as-
ness is the resistance offered by dyed fiber to retain dye under the sessed showed good to excellent responses and Perspiration and chlo-
rinated values (fastness) were comparable with reactive red 195. The
structure of standard dye (reactive red 195) is based on H-acid which
Table 2
showed similar fastness properties to the reactive dyes under investi-
Colorimetric data of dyed cotton by pad thermofix dyeing method of six reactive dyes gation.
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and commercial dye (Reactive Red 195).

4. Conclusions
Dye Dye Shade L* a* b* C* h* K/S

Reactive 43.67 38.32 − 9.61 44.5 0.2 14.56 Cotton fiber was dyed with six reactive dyes (have different num-
195 ber and positions of functional groups) through pad dyeing. The dye-
ing parameters like temperature, pH and reaction time were optimized
D1 45.48 39.89 0.12 39.89 0.9 11.35 and dyeing properties were compared with commercial dye (reac-
CO

tive red 195). Under similar dyeing condition, all dyes showed vari-
D2 48.25 45.01 − 2.11 38.06 0.6 8.53
able colour strength and fastness properties of dyed cotton were also
found to variable for different dyes. The change colour strength and
fastness properties of cotton fiber correlated with functional groups
D3 38.77 40.37 2.93 43.48 7.89 17.67 (numbers and their positions). In comparison to commercial
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D4 41.77 46.87 2.26 42.92 4.95 15.52

D5 38.36 51.42 3.47 42.53 7.67 17.52

D6 36.22 41.45 2.32 43.51 5.80 19.85

L*, a*, b*, L*, C*, H* are the colour coordinates. Fig. 5. Tautomerism of reactive dyes.
 Journal of Molecular Liquids xxx (2017) xxx-xxx 5

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