Journal of Saudi Chemical Society (2013) 17, 2328

King Saud University

Journal of Saudi Chemical Society

www.ksu.edu.sa
www.sciencedirect.com

ORIGINAL ARTICLE

Dye xation and decolourization of vinyl sulphone

reactive dyes by using dicyanidiamide xer in the
presence of ferric chloride
M. Javaid Mughal a,*, Rehana Saeed b, M. Naeem a, M. Aleem Ahmed a,
Arfa Yasmien a, Qasim Siddiqui c, Mansoor Iqbal a
a

Applied Chemistry Research Centre (Textile Section) PCSIR Laboratories Complex, Off University Road, Karachi 75280,
Pakistan
b
Chemistry Department of Karachi University, Off University Road, Karachi 75280, Pakistan
c
Textile Commisioner Organistion, Ministry of Textile, Govt. of Pakistan, Kandawala Building, Karachi 74400, Pakistan
Received 27 October 2010; accepted 21 February 2011
Available online 24 February 2011

KEYWORDS
Dye xation;
Vinylsulphone;
Dicyanidiamide;
Formaldehyde;
Coagulation

Abstract A synthetic polymer was synthesized and used for the improvement of dyeing properties
as well as decolorization of textile waste water. Two dyes were selected having anthraquinone based
Remazol Blue R and azo based Remazol Red RB. It was observed that the synthetic polymer can be
used as xer for the xation of dye by crosslinking between dye and bre, which not only improves
the dyeing properties but also helpful to coagulate the colour after dyeing. By single point method the
concentrations of synthetic polymer were calculated in residual after dyeing. It was examined that the
residual synthetic polymer is helpful in colour removal efciency by coagulation of polymer with dye
to form heavy molecules which settle down and decolorization occurred. Colour removal efciency
was found dependents on pH, concentration of synthetic polymer and inorganic coagulant.
2011 King Saud University. Production and hosting by Elsevier B.V.
Open access under CC BY-NC-ND license.

* Corresponding author. Tel.: +92 3333423197.

E-mail addresses: javaidtextile@hotmail.com, Javaid_textile_pcsir@
yahoo.com (M.J. Mughal).
1319-6103 2011 King Saud University. Production and hosting by
Elsevier B.V. Open access under CC BY-NC-ND license.
Peer review under responsibility of King Saud University.
doi:10.1016/j.jscs.2011.02.017

Production and hosting by Elsevier

1. Introduction
Reactive dyes are the most important class of dyes used for
cellulosic substrate because their high wet fastness, brilliance
and range of hues (Carvalho et al., 2002). The cotton ber
assumes a negative charge on its surface in aqueous solution
(Chaiyapat Pisuntornsug et al., 2002). The most attractive
feature of the use of these dyes is the essential simplicity of
the dyeing process. However, the use of these dyes cause
certain problems, including the use of high electrolyte concentrations and the low wet fastness properties of the dyed materials. Despite the use of high electrolyte concentrations, the

24
exhaustion of the dyebath is still limited and the discharge of
coloured efuent leads to pollution problems.
Notable improvements in the wet fastness properties of anionic dyes can be brought about by pretreatment or after treatment of textile bers. The use of pretreatments or after
treatments to improve the fastness properties of dyeing has a
long and prolic history. Various pretreatment and after treatments system have been developed but at the moment most
widely used are cationic xing agents. These chemicals function by forming a complex of high molecular weight and low
aqueous solubility and therefore high wet fastness, amines,
quaternary ammonium, phosphonium, and tertiary sulphonium compounds and dicyanidiamide, formaldehyde can be used
as dye xing agents to improve there wet fastness properties.
By far the most important type of cationic xing agents used
in textile processing, have been applied to the bres either as
pretreatments or after treatments to improve the fastness properties of anionic dye (Saima Sharif et al., 2007). Every textile
plant requires large volumes of water and produces high volumes of efuent wastewater. The typical textile dye wastewater
composition is quite complex due to usage of various chemicals such as wetting agents, dyes, surfactants, xing agents,
softeners and many other additives are used in wet processes
such as bleaching, dyeing and nishing processes (Rehana
Saeed et al., 2009).
Typical dye wastewater treatment methods are coagulation,
adsorption and oxidation in combination with biological treatments. Combined treatment methods such as adsorption processes by various adsorbents, advanced oxidation processes
(using H2O2, Ozone, UV, etc) and biodegradation (aerobic
and anaerobic) have been also proposed for the treatment of
reactive dye wastewater (Sojka- et al., 1998; Bonat et al.,
1996). Coagulation and occulation processes have been
widely used as pretreatments to remove suspended particles
and coloring materials prior to biological treatment (Abdo
MSE and Al-Ameeri, 1996; Ciardelli et al., 2001). The removal
of color by coagulation is widely employed treatments process
(Duan and Gregory, 1996; Tan et al., 2000; Jiang and Graham,
1996), Al(lll) and Fe(lll) coagulants are two principle inorganic
coagulants used in wastewater treatment. These hydrolysable
cations are readily available as surface or chloride salts in bath
liquid and solid form. However, aluminum is suspected harmful to human and living organisms (Jiang et al., 1993). Thus,
ferric ions are often the coagulants of choice to destabilize colloidal and suspend solids. The use of inorganic coagulants and
organic coagulants together was proved to be effective to treat
water and wastewater (Gabetich et al., 2004).
In this present study dicyandiamide xer is synthesis, for enhance the xing property of vinyl sulphone reactive dyes. By the
use of this polymer the increasing coagulation efciency was
also improved. It was noted that polymer was not only used
for xation of dye molecules on the bre but it also may helpful
in decolorisation process of reactive dyes by reducing the cost
and protecting the environment from possible pollution effects.

2. Material and methods

2.1. Materials

M.J. Mughal et al.

hydrochloric acid, sodium chloride, sodium bicarbonate, ferric
chloride were used as analytical grade, purchased from Merck
chemicals Pakistan. Reactive Red RB, Reactive Blue R
(Dystar, Karachi, Pakistan), were used for this study. The
characteristics of these Remazol dyes are given in Table 1.
Dicyandiamide, Wetting agent Sandopan DTC were used
commercial grade are purchased from local market of Karachi.
O

SO3Na

HN

SO2CH2CH2OSO3Na

Reactive Blue R

Cl
N

NaO3SH2CH2CO3S

OH

NaO3S

N
N

N
SO3Na

SO3Na

Reactive Red RB

2.2. Equipments
Dyeing was carried out on IR dyeing machine of AHIBA.
Colour matching system of Data colour SF 650X was used
for the evaluation of colorimetric data. Washing fastness
(ISO-105-CO3) was carried out on IR dyeing machine of
AHIBA. Crocking fastness (ISO-105-X12) carried out on
crockmeter Atlas. Fastness rating was evaluated on colour
matching cabinet by comparing with grey-scale. UV-spectrophotometer (Nicolet evaluation 100, Thermo electron) was
used to measure the kmax of synthetic polymer as well as to
calculate the decolorization efciency. The equation used to
calculate the colour removal efciency was
%Colour removal Abs0  Abst 100

Abs0

Where Abs0 and Abst were the absorbance of the dye in solution at the beginning of the experiment and at the time t,
Table 1

Characterizations of Remazol reactive dyes.

Parameters

Remazol Blue R Remazol Red RB

Color index name

Chromophore group
Reactive anchor systems
Molar mass (g/mol)
Max Abs kmax (nm)
Molar extinction coecients
Purity (%)
Water solubility at 293 K (g/l)
Company

Reactive Blue 19
Anthraquinone
VSa
524.50
596
3996.852
50
100
Dystar

Scoured and bleached optical brightener free 100%, woven

cotton fabric was used. Formaldehyde solution, acetic acid,

NH2

Vinyl sulphone.
Monochlorotriazine.

Reactive Red 198

Azo
MCTb + VSa
984.22
534
16092.51
63
70
Dystar

Dye xation and decolourization of vinyl sulphone reactive dyes

25

respectively. The pH value was measured with Digital pH-meter (Model Mettler Toledo seven Multi Switzerland). Coagulation process was carried on laboratory stirrer, having speed
200 rpm.

with deionized water to obtain 50% (wt%) of polymer content

(Duk Jong et al., 2007).

2.3. Methods

3.1. Crosslinking between fabric and dye molecules

Eleven fabrics samples were dyed with each dye i.e. Remazol
Red RB and Remazol Blue R in a laboratory dyeing machine
(Ahiba, Datacolour International) at a liquor ratio of 30:1.
The dye bath was prepared by adding dye 10 g/l, sodium chloride 60 g/l and sodium carbonate 10 g/l to distill water at room
temperature. Dyeing was started for 5 min at room temperature then it was raised to 60 C at 1 C/min. Dyeing was continued at 60 C for 45 min. After dyeing the waste solutions
were separated and out of 11, 10 dyed fabric were introduced
in xer solution with different concentration (0.55 g/l), xation was carried out at 60 C for 20 min. The eleventh fabric
was considered as without treatment. After xation the solutions were separated and fabrics were rinsed thoroughly in
hot water and a soap solution of 1 g/l with non-ionic surfactants. The absorbance of xer solution was measured before
and after xation by using spectrophotometer. Both waste
solution of dye and xer are mixed and after adding FeCl3
as 1 g/l, the solution is further coagulated. All coagulation
experiments were conducted in 1.0 L Pyrex glass beakers using
a conventional Jar-test apparatus, the laboratory stirrer.
250 ml waste water was dosage with different concentration
of synthetic polymer with inorganic coagulant. The solutions
were stirred rapidly at 120 rpm for 5 min during inorganic
coagulation addition, and followed by slow stirring at
30 rpm for 15 min and sedimentation for 20 min. After sedimentation, supernatant samples were taken from a point of
1 cm below the surface of the test water sample for analysis.

Fixer is used on textile to hold the unxed dye molecules on

fabric through polymerization between fabric and dyes. The
crosslinking of Red RB and Blue R with the fabric can be
attributed in Fig. 1. The absorbance of synthetic polymer at
240 nm has been recorded at concentration level 0.55 g/l. It
has been observed that the absorbance gradually increased,
which shows to obey the Lambert Beers law. The absorbance
was again recorded, of the residual solution with double beam
UV spectrophotometer. The trend in the observed values of
absorbance of dyed efuent containing polymer was same as
the absorbance of the pure polymer solutions. Infact, the residual absorbance remarkably reduces from above 2.5 to less than
1. This difference in absorbance is the evidence by the fact that
major part of synthetic polymer was used in crosslinking between fabric and dye molecules, which not only improves the
xation but also improves the fastness result.
It has also been noticed from the residual concentration
values, that the polymer was slightly more consumed in the
reactive Red RB dyed efuent as compared to the reactive Blue
R dyed efuent, may be due to the fact that the Red RB dye
molecules even having a bigger molecular size rather than Blue
R dye molecules (Dizge et al., 2008). By apply single point
method, the concentration of synthetic polymer in residual
were calculated from the residual absorbance i.e., from 0.09
to 1 g/l, which may helpful in the decolorization process of
residual of bath dyes.

3. Results and discussions

3.2. Effect of synthetic polymer on dyeing

2.4. Measurement of dye xation
The xation of the dye in percentage was calculated rst by
determining the reectance R of the dyed samples at the wavelength of minimum reectance (maximum absorbance) on a
Data colour SF 650X spectrophotometer. The colour yield
(K/S) value was then calculated by using the KubelkaMunk
equation (Eq. (2)) and the dye xation (%) was evaluated
using Eq. (3).
K=S 1  R2 =2R

3.2.1. Fixation
Synthetic polymer was used as a xer for xation of unxed
dye by crosslinking agent. It was observed that, with out using
xer the xation percentage is 71% and 74% for Red RB and
Blue R respectively. When xer is using, the dyed fabric percent xation is enhanced which increases to 86% and 87%
for Red RB and Blue R respectively in Table 2 show that

4
3.5

%Dye fixation K=Svalue of sample after soaping 100

3
2.5. Synthesis of polymer
A polymer was synthesized in a 500 ml glass reactor equipped
with temperature controller; mechanical stirred having
150 rpm speed, with dropping funnel for formaldehyde solution. Para formaldehyde was dissolved in HCl solutions (0.1
0.5 mol). The formaldehyde reacts with industrial grade dicyandiamide, solution in HCl which was added drop wise
through a dropping funnel for 26 h at 6080 C. After the
reaction was completed, aqueous polymer solution was diluted

Absorbance

K=Svalue of sample before soaping

Abs at 248nm Before

2.5
2

After residual Abs of Red

1.5

After residual Abs of Blue

1
0.5
0
0

Concentration of Polymer (g/l)

Figure 1 Absorbance of variable concentration of synthetic
polymer before and after dyeing.

26

M.J. Mughal et al.

Fixation, fastness and color coordinates of Remazol Red RB and Remazol Blue R.

Table 2
Dye conc.

Polymer conc. (g/l)

% x

Washing
fastness
ISO-105-CO3

Crocking fastness ISO-150-X12

Dry

Wet

Remazol Red RB 10 g/l

Without treatment
0.5
1
1.5
2
2.5
3
3.5
4
4.5
5

71%
72%
75
75
78
78
81
82
84
84
86

2/3
3
3
3/4
4
4
4
4/5
4/5
4/5
4/5

4
4
4
4
4/5
4/5
4/5
4/5
5
5
5

3
3/4
3/4
3/4
4
4
4/5
4/5
4/5
5
5

49.22
48.47
48.19
48.22
47.79
47.78
47.31
47.28
46.52
46.50
45.89

53.88
53.18
54.23
54.07
52.19
52.12
52.63
52.63
53.52
53.50
53.12

3.20
3.40
3.83
3.24
3.66
3.62
3.74
3.73
2.98
2.48
2.36

54.09
53.29
52.42
54.17
52.27
52.25
52.79
52.76
53.57
53.56
53.47

Remazol Blue RB 10 g/l

Without treatment
0.5
1
1.5
2
2.5
3
3.5
4
4.5
5

74
76
76
78
79
82
85
86
86
87
87

3
3
3/4
4
4
4
4/5
5
5
5
5

4
4
4
4
4
4/5
4/5
4/5
5
5
5

3
3/4
3/4
3/4
3/4
4/5
4/5
4/5
4/5
5
5

54.70
53.86
53.59
53.27
53.26
53.01
52.87
52.51
52.84
51.75
51.21

3.36
3.45
3.41
3.14
3.94
4.03
3.51
3.82
3.50
3.59
3.67

37.28
37.22
36.62
37.22
38.58
34.85
38.86
38.40
39.04
38.52
39.56

37.43
37.38
36.78
37.21
38.78
35.08
38.02
38.59
39.20
38.69
38.88

the polymer improves the dye xation of both dyes. As the

concentration of polymer increases the xation also increases
which was particularly true for the crosslinking of xer between ber and dyes molecules.
3.2.2. Colour measurement of dyed fabric
Measurement of colour yield (K/S) values of dyed fabric is a
measure of dye concentration on the fabrics. Fig. 2 shows
the relation between K/S and the concentration of polymer applied after dyeing for each dyes. Both dyes show good colour
yield with the increase in concentration of polymer. A sharp
build up properties were observed up to 3.0 g/l but then a characteristics change was occurred. In fact, by applying xer the
unxed dye may also link to the fabric to enhance the dyeing
yield of the dyed fabric. Above 3.0 g/l of xer, the crosslinking

K/S Values

4.5
4
3.5
3
K/S value of Red

3.2.3. Colour fastness

In all cases the fabric treated with xer have better fastness results in Table 2. It is explained that during dyeing, the unxed
dyes may also present on dyed fabric which results in low fastness results as during washing, the untreated fastness rating is
2/3, 3 and wet crocking fastness rating is 3, 3 for Red RB and
Blue R, respectively. When xer is used at 5 g/l the fastness
rating is improve to 4/5, 5 for washing and wet crocking fastness rating 5,5 for Red RB and Blue R respectively. Some of
these unxed dyes can undergoes in crosslinking, so giving a
better fastness as well as less polluted efuents. As the crosslinking process also increases the fastness also improves. In
staining process of the fabric shows the same manner.
3.3. Effect of synthetic polymer on decolorization efciency

K/S value of Blue

2.5

was reduced may be due to over crowded of molecules to restrict the crosslinking.
Colour coordinates CIE LAB L*, a*, b* and C* were determined to dened the properties of colour on dyed fabric. In
Table 1 the value of L shows that as the xation improves with
increase in polymer concentration. The depth of shade also increases from 49.22 to 48.47 and 54.70 to 51.21 for Red RB and
Blue R respectively. On applying the polymer, the depth instantly improves and after that it gradually and steadily improves. The value of a, b, c follows the Munsell equation
and show the maintaining of colour.

Concentration of Polymer (g/l)

Figure 2 K/S value of Remazol Red RB and Remazol Blue R
using different concentration of synthetic after dyeing.

3.3.1. Effect of pH
The wastewater from textile industries usually has a wide range
of pH values. Generally, pH plays an important role in the
characteristics of textile wastewater (Neppolian et al., 2002).
In wastewater treatment using inorganic coagulant with

Dye xation and decolourization of vinyl sulphone reactive dyes

3.3.2. Effect of polymer concentration

The effect of polymer dosage on the colour removal of real
waste water was investigated. Polymer dosage was increased
01 g/l with a xed concentration of ferric (0.7 g/l). The initial
pH of wastewater was adjusted to pH 4.5. The colour removal
efciency gradually increased by increasing the concentration
of polymer, about 90% of decolorization was observed in case
of Blue R when polymer dosage was above 0.5 g/l, but in case

Colour removal

100

95

90
85
Red RB
Blue R

80
0

10

pH
Figure 3

Decolorization of Remazol dyes at various pH.

Colour removal %

100
80
60
40
20

90

Colour removal%

synthetic polymer coagulants, an optimum pH range in which

metal hydroxide precipitates occur, should be determined
(Choi et al., 2001). The effect of pH on the vinyl sulphone reactive dyes removal was determined by using xed amount of ferric chloride (0.7 g/l) and polymer (1 g/l) in this study. The
removal of Blue R decreases when pH increases, but in case
of Red RB, the color removal was highly dependent over the
alkaline pH, which increases as pH increases in ferric/polymer
system which shows in Fig. 3. The optimum pH was observed
for both of dyes are near at pH 4.5. The results indicate that
pH should be properly controlled upon the characteristics of
inorganic coagulant and the target dyes for efcient treatments. An highly alkaline waste water, the ferric ions form
complex with OH ions, which is more stable as far as synthetic
polymer bridging system thats why the color removal efciency decreases with increasing the pH range.

27

70

50

30
Red RB
Blue R

10
0.3

0.5

0.7

0.9

Concentration of Ferric chloride (g/l)

Figure 5 Decolorization of Remazol dyes with different concentration of inorganic coagulant (ferric chloride).

Red RB required additional amount of polymer dosage which

shows in Fig. 4.
The coagulation of suspended particles and colloids result
by various mechanisms, including electrostatics attraction,
sorption and bridging related to the high molecular weight
of the polymer (Roussy et al., 2005). Therefore, the interaction
between dye molecules and synthetic polymer is basically the
combined effect of the charges on the dye molecules and the
surface of the polymer-ferric system.
3.3.3. Effect of inorganic coagulant dosage
The inuence of ferric chloride dosage on the vinyl sulphone
reactive dyes colour removal efciency was measured. In this
experiment the variable amount of ferric chloride is (0.3 g
1 g/l), the colour removal efciency was not signicantly changed which shows in Fig. 5. The test result shows that the reduced in inorganic coagulant dose with small amount of
polymer coagulant gives good performance as compared to
the use of inorganic coagulant only (Lee et al., 1998), while
reactive dyes, which are characterized by azo bands (NN)
and have SO3, COO, OH groups have high solubility,
they are not prone to be adsorbed by Fe(OH)x particles
(Al-Degs et al., 2000; Kim et al., 2004). The colour removal
efciency of both of the dyes is 98.5% and 99.8% for Red
RB and Blue R, respectively. In case of colour removal efciency of FeCl3 without with synthetic polymer, such no colour
removal efciency was observed at any iron dose examined in
the coagulation test, although the formation of small amount
of oc was observed (Surina J. Ergas et al., 2006). The appropriate amount of synthetic polymer and inorganic coagulant
resulted in reduction of sludge production by reducing the dose
of inorganic coagulants.
4. Conclusion

Colour removal Red

Colour removal Blue

0
0.05 0.15 0.25 0.35 0.45 0.55 0.65 0.75 0.85 0.95

Concentration of Polymer (g/l)

Figure 4 Decolorization of Remazol dyes with various concentration of synthetic polymer.

In the present research works, we have synthesized dicyandiamide/formaldehyde based polymer, and their application on
the cotton substrate for the xation of vinyl sulphone reactive
dyes as well as on the treatment of dyes waste water. By the
above investigation the following conclusions have been
drawn.
Dye xation signicantly by the application of synthetic
polymer. The % xation efciency without the treatment of

28
synthetic polymer was found 71% for Red RB and 74% for
Blue R, but after polymer application it increases upto 86
87% for both the dyes at a polymer concentration of 5 g/l. It
has also been observed, after polymer application the washing
and crocking fastness remarkably enhanced, especially we observed an increase in the fastness properties of Red RB dyes,
which are normally in moderate range in conventional dyeing
process. The optimum value of K/S was found 4.2 at a polymer
concentration of 4 g/l for both dyes.
After the xation process the polymer was found in waste
water at the range of concentration 0.050.95 g/l, which is useful in the coagulation of reactive dyes in further process. In
colour removal efciency the optimum pH was observed for
the both the dyes at 4.5 in case of coagulation in the presence
of 0.7 g/l ferric chloride and at a polymer concentration of 1 g/
l. The colour removal efciency gradually increased by increasing the concentration of polymer, about 90% of decolorization
was observed in case of Blue R at a polymer concentration of
0.5 g/l. The Red RB dyes required an additional amount of
synthetic polymer. It is also evident that the reduced inorganic
coagulant (ferric chloride) dose with small amount of polymer
gives good performance results as compared to the use of inorganic coagulant alone. Dicyandiamide-formaldehyde polymer
is use full in terms of dye xation and decolorization of dyeing
waste water by reducing the cost of textile industry.
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