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Eco-friendly cationic modication of cotton fabrics

for improving utilization of reactive dyes
Cite this: RSC Adv., 2015, 5, 45654
Long Fang, Xiaodong Zhang,* Jinhai Ma, Deshuai Sun, Botao Zhang and Jimei Luan

Received 2nd April 2015
Accepted 7th May 2015
DOI: 10.1039/c5ra05887b
www.rsc.org/advances
Cotton fabric was chemically modied by a prepared eco-friendly cationic polymer. The cationic polymer
was synthesized by the reaction of dimethylamine and epichlorohydrin using the novel method of three-
step polycondensation. And it was characterized by Fourier transform infrared (FTIR) spectroscopy,
1
H nuclear magnetic resonance (1H NMR) and gel permeation chromatography (GPC). Moreover, the
structures of both untreated and treated cotton fabrics were compared and investigated by FTIR, X-ray
diraction (XRD) and scanning electron microscopy (SEM). The dyeing properties of the treated cotton
fabrics are discussed. The results indicated that the total dye utilization of treated cotton by salt-free
dyeing was much higher than that of untreated cotton by conventional dyeing. And the color fastness
properties, the dyeing levelness and the tear strength of treated cotton were all satisfactory and could
meet application demands. The environmental hazard caused by the dye wastewater could be
decreased greatly in the dyeing process.

groups into cotton fabrics for enhancing interactions between

1. Introduction
Cotton fabric is the most widely used textile in the world and is
composed almost entirely of cellulose (9096% based on weight
of bres).1 Cotton fabric characteristically exhibits excellent
physical and chemical properties: for example, stability, being
comfortable to wear, high water absorbency and dyeability. In
industrial processes, reactive dyes are widely used for cotton
fabric dyeing due to their relative ease of application, wide color
gamut and high wet fastness.2 However, reactive dyeing systems
require huge amounts of electrolyte (NaCl or Na2SO4) to over-
come the repulsive charge between cotton and reactive dyes.
These electrolytes are neither exhausted nor destroyed aer
dyeing and only 6065% dye utilization is attainable.3 The
residual dyes and electrolytes have caused severe environmental
problems and disorders in living organisms.4
Over the years, many attempts have been made to enhance
fabric-dye anity for improving utilization of reactive dyes and
eliminating or reducing the amount of electrolyte.512 An
alternative approach is either to dye cotton with new reactive
dyes or to pre-treat cotton followed by reactive dyeing. These
new reactive dyes contain two or three functional (reactive)
groups per molecule. And the combination of reactive groups
greatly improves their dyeing ability and possibility for appli-
cations.13 The total utilization of reactive dyes can be increased
from an average of 60% to approximately 80%.14 Many
researchers have recently focused on introducing cationic
College of Chemical Engineering and Environmental, Qingdao University, Qingdao
266071, China. E-mail: zhangxdqd@hotmail.com; Fax: +86-532-85950518; Tel: +86-
532-85955589
cotton and reactive dyes. Such treated cotton fabrics can be
dyed with reactive dyes under neutral or mildly acidic condi-
tions without the addition of electrolyte, and dye utilization
eciency can be greatly increased. But there are some disad-
vantages which make it dicult to apply to industrial
production; for instance, the high production cost, the health
and safety of industrial production, the repeated pollution, and
the degradation of wearability.15,16
The epichlorohydrindimethylamine polymer is an eco-
friendly cationic polymer. It was reported that this cationic
polymer could be synthesized by two-step polycondensation,
whose weight-average molecular weight was less than 10 000 g
mol.1719 But it only had a single function, either as dye xative
agent or as occulant. It is appreciated that the cationic polymer
is useful for drinking-water treatment and no data are available
regarding its toxicity.17,20
In this context, epichlorohydrindimethylamine polymer
was prepared by the novel process of three-step poly-
condensation. Based on two-step polycondensation, the poly-
mer molecules were further polymerized under the catalysis of
alkali and formed an ordered cationic polymer with higher
molecular weights. The synthesis process conditions of the
cationic polymer were investigated and optimized. The polymer
was applied to modify cotton fabrics as cationizing reagent and
also to allow disposal of dye wastewater as a occulant. It did
not result in further pollution. The dyeing eect of the modied
cotton fabrics in salt-free dyeing was tested and compared with
that of raw cotton fabrics in conventional dyeing. And the green
modication method could greatly enhance the dyeability of
cotton fabrics to achieve euent reduction.

45654 | RSC Adv., 2015, 5, 4565445661 This journal is The Royal Society of Chemistry 2015

Paper
2. Experimental part
2.1 Materials and chemicals
Epichlorohydrin (AR), dimethylamine (CP), diethylenetriamine
(AR) and other chemicals were purchased from Sinopharm
Chemical Regent Co. Ltd.
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The cotton fabric (bleached, desized and mercerized, 100
g m
2) was purchased from Qingdao Fanglian Group Co. Ltd.
The commercial reactive dyes CI Reactive Blue 19 and CI
Reactive Black 5 were obtained from Shanghai Dyestu Co. Ltd,
China; CI Reactive Red 195 and CI Reactive Yellow 176 were
purchased from Zhejiang Longsheng Group Co. Ltd, China.
Their structures are shown in Fig. 1.
2.2 Synthesis of epichlorohydrindimethylamine polymer
The cationic polymer was prepared by the reaction of dime-
thylamine and epichlorohydrin using the method of gradually
increasing temperature and three-step polycondensation. In the
rst step, dimethylamine and a crosslinking agent were rst
added to a 250 mL glass reactor equipped with a mechanical
stirrer at 010  C. Epichlorohydrin was added dropwise into the
reactor with constant stirring for 3 hours at a temperature below
10  C. The system temperature was slowly raised in a gradient
style, such as at 30  C for 15 minutes, at 40  C for 15 minutes. In
Fig. 1 Molecular structures of the reactive dyes used in the experiments.
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the second step, polycondensation was conducted at specic
temperature for 120 minutes with constant stirring. In the third
step, 4 g sodium hydroxide solution (10 wt%) was added into
the reactor to promote polymerization. When the viscous solu-
tion was climbing the stirrer sha, an appropriate amount of
distilled water was added into the glass reactor to inhibit the
rapid increase of viscosity. When sha-climbing phenomenon
was not apparent, the reaction solution was kept at reaction
temperature for 0.5 h and then hydrochloric acid solution was
added to adjust the pH value to 56. The epichlorohydrin
dimethylamine polymer was puried by alcohol and dried in
vacuum at 50  C for 24 h. The yield was about 96%.
2.3 Chemical modication of cotton fabrics
10 g L
1 epichlorohydrindimethylamine polymer solution was
prepared with distilled water and the pH value of the polymer
solution was adjusted to 13 with NaOH solution (1 mol L
1). The
pressure on the mangle was adjusted to give 80% wet pickup.
Cotton fabrics were dipped and padded twice in the above solu-
tion. Subsequently, the treated cotton fabric was baked at 60  C
for 15 min. Then it was rinsed with water, followed by soaping
with nonionic detergent (OP-10, 1 g L
1) at the boil for 30 min to
remove the physically adsorbed cationic polymer, then rinsed
thoroughly with water and air-dried at room temperature.21
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2.4 Characterization solution with stirring and the dyeing temperature was kept at
60  C for 60 min. Aer dyeing, the dyed fabric was introduced in
The cationicity of the prepared polymer was measured using the
a solution containing 1 g L
1 nonionic surfactant (Triton X-100)
method adopted in the literature.22 The viscosity of the prepared
at 90  C for 20 min at a liquor ratio of 1 : 30, and then rinsed
polymer system before purication was measured by using a
and allowed to air dry.
NDJ-79 Rotary Viscometer.
The chemical structure of the prepared epichlorohydrin
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dimethylamine polymer was conrmed by means of infrared 2.6 Determination of dye exhaustion and xation
(IR) spectroscopy using a Thermo Nicolet IR spectrophotometer The dye exhaustion (E) was determined according to eqn (2),
model IR 460 and 1H NMR spectroscopy using a Bruker AV-500 where A0 is the absorbance of the original dye solution and A1 is
spectrometer. 1H NMR measurements were performed in D2O. the absorbance of the residual dye solution aer dyeing. The
The weight-average molecular weight (Mw) of the prepared dye xation (F) was determined according to eqn (3), where A2 is
polymer was determined by gel permeation chromatography the absorbance of the soap bath aer soaping, and the total
(GPC) (Wyatt Dawn Heleos) with columns of Shodex OHpak SB- utilization of the original dye (T) was determined according to
805HQ (8  300 mm, Showa Denko, Tokyo, Japan) connected in eqn (4). The absorbance of the dye solution was measured at
series. THF was used as the GPC solvent. maximum absorbance of the dye using a Shimadzu UV-1700
Fourier transform infrared (FTIR) spectroscopy experiments spectrophotometer.
with the untreated cotton fabric and treated cotton fabric were A0
A1
carried out. E  100% (2)
A0
A LEO 1530 scanning electron microscope (SEM) was used to
study the surface morphologies of cotton samples. All samples A0
A1
A2
F  100% (3)
were coated by gold sputtering before SEM testing. A0
A1
The cross-section of the dyeing fabrics was observed with an
MIT 500 optical microscope. TEF (4)
The X-ray diraction (XRD) patterns of the cotton fabrics
were recorded stepwise with 2q between 5 and 60 by a Rigaku
D/max 2500 diractometer. The relative crystallinity (C) of the 2.7 Color yield analysis
cotton fabrics was calculated as described by Rabek with the
The color yield strength expressed as K/S value was obtained
following equation, where Ac is the crystalline area and Aa is the
from the KubelkaMunk equation (eqn (5)). The reectance
amorphous area:23,24
ratio (R) was determined at the minimum reectance of the dye
Ac using a CM-2600d spectrophotometer (Konica Minolta). Eight
C  100% (1)
Ac Aa separate points on each cotton fabric sample were measured.
The levelness of the dyed cotton fabric was evaluated using Sr(l).
Before FTIR, SEM and XRD testing, all of the treated cotton A lower Sr(l) means better levelness.25,26 Sr(l) was calculated
fabrics were washed until the cationicity of the washing solution according to eqn (6) and (7).
was not detected. K 1
R2
(5)
S 2R
2.5 Dyeing procedures
X
n

2.5.1 Dyeing procedure for the modied cotton. Exhaustive K=S 1=n K=Sil (6)
i1
dyeing was performed in the absence of salt. The modied
cotton fabric was immersed in 4% dye solution (o.w.f., weight v
u n  2
percent of dye relative to ber) with a liquor ratio of 1 : 30. The uX K=S
u il

1
u
dyeing temperature was kept at 25  C for 30 min and then was t i1 K=S
Sr l (7)
gradually raised to 60  C in 20 minutes. Subsequently, 15 g L
1 n
1
Na2CO3 was added to the dye solution with stirring and the
dyeing temperature was kept at 60  C for 60 min. Aer dyeing,
the dyed cotton fabric was introduced in a solution containing 2.8 Color fastness and tear strength testing
1 g L
1 nonionic surfactant (Triton X-100) at 90  C for 20 min at The washing fastness test of the dyed cotton fabric was per-
a liquor ratio of 1 : 15, and then rinsed and allowed to air dry. formed according to the standard (ISO 105-C06 (C2S)) with an
2.5.2 Dyeing procedure for the untreated cotton. The SW-12 (Dongyuan Testing Machinery) washing machine. The
untreated cotton fabric was immersed in 4% dye solution rubbing fastness test was performed according to the standard
(o.w.f.) with a liquor ratio of 1 : 30. 25 g L
1 NaCl was added to (ISO 105-X12) using a Y571B (Changzhou Textile Instrument Co.
the dye bath with stirring. The dyeing temperature was kept at Ltd) rubbing machine.
25  C for 30 min. Another amount of 25 g L
1 NaCl was added to The tear strength test of cotton fabric samples was per-
the dye bath and the dyeing temperature was slowly raised to formed using a YG (B) 033A tearing instrument (Wenzhou,
60  C in 20 minutes. Then 20 g L
1 Na2CO3 was put into the dye China) according to ASTM D 5734-1995.

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2.9 Flocculation experiments
Flocculation experiments for the residual dye liquor (CI Reac-
tive Black 5) were conducted with a jar test apparatus. Aer the
addition of the epichlorohydrindimethylamine polymer, the
dye solution was stirred rapidly for 3 min at 450 rpm, followed
by stirring slowly for 15 min at 40 rpm and sedimentation for 30
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min. The absorbance of supernatant samples was measured
using a Shimadzu UV-1700 spectrophotometer. The color
removal eciency of the prepared cationic polymer was deter-
mined by comparing the absorbance dierence between orig-
inal and occulated dyeing solution.18
3. Results and discussion
3.1 Characterization of the chemical structure and
evaluation of the prepared polymer
Fig. 2 shows the FTIR spectrum of the prepared cationic polymer.
The peak characteristic of OH stretching was visible at
3419 cm
1.27 And the peaks at 1636 cm
1, 1475 cm
1 and
Fig. 2 FTIR spectrum of the prepared polymer.
1
Fig. 3 H NMR spectrum of the prepared polymer.
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1096 cm
1 indicated the presence of CN vibration and CH2N+
R3 type nitrogen (quaternary ammonium groups).28,29 The band
of medium intensity at 634 cm
1 was typical of the CCl
stretching vibration in the CH2Cl group. The additional peaks at
1280 cm
1 indicated the presence of the CH2Cl group.30
Fig. 3 shows the 1H NMR spectrum of the prepared cationic
polymer. The 1H NMR spectrum of the epichlorohydrindime-
thylamine polymer had the characteristic proton peaks of a
N+CH2 linkage at 3.42 ppm, an N+CH3 linkage at 3.64 ppm, a
CH2 linkage at 1.19 ppm and a CH2Cl linkage at 3.78 ppm.
These results conrmed that dimethylamine had reacted with
epichlorohydrin to form the cationic polymer.
The weight-average molecular weight of the prepared
cationic polymer was 47 150 g mol
1. Its cationicity is
4.975 mmol g
1.
3.2 FTIR study of the modied cotton fabric
The chemical modication process of cotton fabrics is
summarized in Fig. 4. Under basic conditions, the chloromethyl
group of the epichlorohydrindimethylamine polymer could
change into an epoxy group to react with the primary hydroxyl
groups of cotton fabrics. And then quaternary amine groups
could be chemically attached in the cotton fabrics and enhance
the fabric-dye anity. The FTIR spectra of untreated cotton and
treated cotton aer sucient washing are illustrated in Fig. 5.
Compared with the untreated cotton spectrum, an absorption
peak at about 1460 cm
1 appeared in the spectrum of the
treated cotton, which was assigned to the bending vibration
of CN. This observation clearly indicated the presence of
CH2 N+ R3 type nitrogen (quaternary ammonium groups).28 It
fully demonstrated that the quaternary amine group was
chemically adsorbed on the treated cotton fabrics. It indicated
that the reaction between cotton fabrics and cationic polymer
had occurred.
3.3 Surface morphology
SEM was employed to intuitively observe the surface
morphology of untreated cotton and treated cotton, which
could be used to evaluate the inuence of the cationic modi-
cation process. SEM images of untreated cotton and treated
cotton are given in Fig. 6. The wrinkle of the treated cotton
surface was signicantly reduced. The surface of the treated
cotton was smoother and plumper than that of the untreated
cotton. Generally, the cationic modication caused little change
and there was no damage to the structure of the cotton fabrics.
3.4 X-ray diraction (XRD) analysis
Fig. 7 shows the XRD patterns of the untreated and treated
cotton. Typical diraction peaks appeared at 2q 14.5 , 16.2 ,
22.3 , and 33.7 in both Fig. 7(a) and (b) which are typical of
cellulose I crystalline form, in perfect accordance with a
previous study.31 Moreover, the peak intensity of the patterns of
cotton fabrics before and aer cationic modication changed
very little. The relative crystallinities of untreated cotton and
treated cotton were 58.3% and 59.7%, respectively. This meant
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Fig. 4 Scheme of modication reaction and dyeing process.
Fig. 5 FTIR spectra of cotton fabric samples.
that cationic modication le almost unchanged the main
crystalline form and crystal structure of the cotton fabrics.
3.5 The optimum reaction conditions of the cationic
polymer
The method of increasing temperature gradually could mean
the polymerization reaction slowly forms regular oligomers in
the rst step of polycondensation. Then these regular oligomers
formed relatively larger polymer molecules in the second step of
45658 | RSC Adv., 2015, 5, 4565445661
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polycondensation. In the third step, polymer molecules were
further polymerized by the catalysis of alkali and formed
ordered cationic polymer with higher molecular weights.
The eect of the monomer ratio, the reaction temperature
and the crosslinking agent was evaluated with the total dye
utilization (CI Reactive Black 5) of cotton fabrics modied by the
prepared cationic polymer. Fig. 8 shows that the total dye utili-
zation of modied cotton fabrics was greatly improved. Total dye
utilization increased with an increase of polymer solution
viscosity. That is to say, the greater the average molecular weight
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of the cationic polymer is, the higher the total dye utilization of
modied cotton. The cationic polymer with high molecular
weights had usually a high cationic degree and thus showed high
substantivity. The optimized process conditions were as follows:
reaction temperature was 65  C, mole ratio of epichlorohydrin to
dimethylamine was 1.3, and the crosslinking agent was
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diethylenetriamine whose dosage was 3%.

Fig. 6 SEM images of cotton fabric samples: (a) untreated and (b) 3.6 Fastness properties and tear strength
treated.
Table 1 summarizes the tear strength and color fastness prop-
erties of untreated and treated cotton fabrics. The tear strength

Fig. 7 XRD patterns of cotton fabric samples: (a) untreated and (b) treated.

Fig. 8 The inuence of the monomer ratio, the reaction temperature and the crosslinking agent.

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Table 1 The tear strength and color fastness properties of dyed cotton was slightly higher than that of untreated cotton, the levelness
fabrics of the cationic cotton was relatively good. The cross-section of
the dyed cotton sample was examined under an optical micro-
Rub Tear
Wash fastness fastness strength (N) scope, as shown in Fig. 9. It was found that the inside of the
cationic cotton was largely colored and darker than the
Staining untreated cotton, which demonstrated that the reactive dye had
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Fabric Shade change Cotton Wool Dry Wet Warp We penetrated into the center of the fabrics under salt-free dyeing
conditions.
Untreated 45 45 45 45 34 22.9 17.4 The dyeing mechanism was postulated and is shown in
Treated 4 45 45 4 34 22.7 17.3 Fig. 4. It was thought that most of the reactive dyes were easily
absorbed and diused into the modied cotton by opposite
charges attracting in the exhaust dyeing process. The above-
Table 2 Dyeing eect of untreated and treated cotton fabrics mentioned absorption could greatly increase the concentra-
tion of reactive dyes inside the treated cotton, which enhances
Untreated cotton Treated cotton
dye-ber xation reaction in the dye-xation process. To some
Reactive dye name T (%) K/S Sr(l) T (%) K/S Sr(l) degree, the positive charge of the modied cotton could
temporarily restrict the movement of anions, especially the
CI Reactive Black 5 52.9 21.68 0.065 92.7 25.32 0.076
hydroxyl anion, which accordingly decreases the hydrolysis of
CI Reactive Blue 19 56.8 16.08 0.061 88.6 22.84 0.068
CI Reactive Yellow 176 64.2 16.56 0.045 93.3 19.41 0.046 reactive dyes. So the total utilization of reactive dyes was
CI Reactive Red 195 67.4 19.33 0.058 85.5 20.21 0.053 improved greatly. On the other hand, the sulfatoethyl sulfonyl
dye could be easily changed into a vinyl sulfone reactive dye by
the elimination reaction probably due to the existence of posi-
of treated cotton fabric was reduced very slightly. The treated tive charges in the modied cotton. And the generated small
cotton fabric showed equal or lower rub fastness and wash molecule with vinyl sulfone groups could move and attack cel-
fastness ratings as compared to the untreated one. These results lulosate anions to form a conventional dye-bre bond. There-
were relatively good and were up to the application standard for fore the dyeing levelness of the treated cotton could be secured.
dyed fabrics. The cationic modication process had almost no
negative inuence on the tear strength and color fastness 3.8 Decolorization performance of the prepared cationic
properties of cotton fabrics. polymer
A occulation experiment for the removal of residual dyes
3.7 Suitability of modied cotton fabrics with other reactive (CI Reactive Black 5) was performed. The composition of
dyes residual dyes was that the reactive dye concentration was 0.1
In this section, other reactive dyes were used to assess the g L
1 and the nonionic surfactant (Triton X-100) concentration
suitability of cationic modication. The cationic cotton was was 0.3 g L
1. The variations of color removal eciency with
dyed without the addition of salt and untreated cotton was dyed occulant dosage are presented in Fig. 10. Almost 94% e-
with the conventional method (adding 50 g L
1 NaCl). Table 2 ciency was achieved at 60 mg L
1 dosage. The result indicated
shows that the color yield and the total dye utilization of the that the prepared cationic polymer was highly eective for
cationic cotton with four reactive dyes were all much higher treating CI Reactive Black 5 wastewater.
than those of untreated cotton. In comparison with untreated In the washing liquid of the modifying process, the cationic
cotton, the cationic cotton displayed excellent color strength polymer concentration was about 101126 mg L
1 (per gram of
using salt-free dyeing. Though Sr(l) of the cationic cotton fabric cotton fabrics) from measurement of cationicity. So the washing

Fig. 9 Microscope photos of cotton fabrics dyed with CI Reactive Black 5: (a) untreated cotton after conventional dyeing and (b) treated cotton
after salt-free dyeing (400).

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Fig. 10 Eect of cationic polymer dosage on color removal in the
residual dye liquor (CI Reactive Black 5).
liquid could be collected to occulate dye wastewater. And the
modifying solution could be recycled and the residue also could
be used to dispose of dye wastewater. So the cationic polymer
has good occulating property and possesses signicant
potential to modify cotton fabrics in a green manner.
4. Conclusions
A novel epichlorohydrindimethylamine polymer with
controlled molecular weight and controlled cationicity was
successfully synthesized. FTIR analysis and 1H NMR analysis
conrmed the expected structure.
This study conrmed that aer the chemical modication of
the cotton fabrics, the total utilization of reactive dyes was
improved greatly in the absence of salt. Besides, the color
fastness properties and levelness of modied cotton fabrics
were both satisfactory.
The cationic polymer had good occulating property and did
not result in repeated pollution. The investigation provided a
feasible and eco-friendly way to realize salt-free dyeing with
reactive dyes.
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