J Mater Cycles Waste Manag (2014) 16:557–565
DOI 10.1007/s10163-013-0210-1
ORIGINAL ARTICLE
Converting waste expanded polystyrene into polymeric azo dyes
containing the sulfonamide group
Dan Liu • Junlong Liu
Received: 4 March 2013 / Accepted: 9 October 2013 / Published online: 24 October 2013
Ó Springer Japan 2013
Abstract Using waste expanded polystyrene as raw
materials, a series of polymeric azo dyes containing the
sulfonamide group were prepared by chlorosulfonation,
amidation, hydrolysis, diazotization and coupling reactions
in this study. The main influence factors of each step
reaction were discussed and the proper reaction conditions
were obtained. The polymeric azo dyes prepared showed
good thermal stabilities, and their 5 % weight loss tem-
peratures were all higher than 350 °C. These polymeric
dyes could solve in toluene at the room temperature. They
showed different maximum absorption wavelengths in the
ultraviolet–visible region and gave various colors. The
relationships between colors and molecular structures of
polymeric dyes were investigated. These polymeric azo
dyes prepared have potential applications in dyeing poly-
mer materials, such as plastic and fiber.
Keywords Waste plastic  Polystyrene  Polymeric
azo dye  Sulfonamide group
Introduction
Polystyrene (PS) is the third-most-used thermoplastic after
polyethylene (PE) and polypropylene (PP) in the world. As
an important product of PS, expanded polystyrene (EPS) is
widely used as packaging materials and insulating
D. Liu
College of Biological, Chemical Sciences and Engineering,
Jiaxing University, Jiaxing 314001, People’s Republic of China
J. Liu (&)
School of Textile and Material Engineering, Dalian Polytechnic
University, Dalian 116034, People’s Republic of China
e-mail: junlongliu@163.com
materials in various industrial fields due to its excellent
properties, such as good strength, light weight, outstanding
durability and low cost. However, waste expanded poly-
styrene (WEPS) is causing serious environmental problems
because of the nonbiodegradability of WEPS. Landfilling
and incineration, traditional disposal methods of WEPS,
cannot completely solve the environmental pollution of
WEPS because these ways easily cause secondary pollution
[1, 2]. Recycling is a promising alternative to landfilling
and incineration for the treatment of WEPS. Recycling
WEPS to useful productions can not only effectively
resolve the problem of environmental pollution of WEPS,
but also has important significance for the sustainable
development of natural resources. Thermal pyrolysis, i.e.,
converting WEPS into oil and gas or the corresponding
monomers, is one of the widely used procedures for recy-
cling WEPS [3–6]. However, such a recovery process is
often not efficient because the values of recycling products
are generally lower than the costs in recycling process [7].
It is well known that various functional groups, such as
nitro, bromine, chloromethyl and so on, can be easily
introduced into PS molecule structure by use of the high
reactivity of benzene ring on the side chain of PS via
nitration, halogenation, chloromethylation, etc. Accord-
ingly, many functional polymers can be obtained using
WEPS as raw materials for some chemical reactions.
Compared with thermal recycling, converting WEPS to
useful high-value functional polymer products is more
valuable by chemical modification. Some modified pro-
ductions, such as flocculants [8–11], adhesives [12], sur-
face active agents [13] and adsorbents [14], have been
prepared from WEPS.
Azo dyes are a kind of compounds that contain two
aromatic fragments connected by a –N=N– double bond,
which are generally prepared by diazotization of a primary
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aromatic amine followed by coupling the resultant diazo-
nium salt with an electron donating aromatic compound
[15–20]. Azo dyes are the most important class of synthetic
dyes, accounting for more than half of all synthetic dyes.
However, there are still some problems in practical appli-
cation of these low molecular dyes because of their poor
solvent resistance and heat resistance, high transference,
and severe environmental pollution. Polymeric dyes have
many advantages over low molecular organic dyes, such as
high strength, good solvent resistance and heat resistance,
excellent processing properties, low toxicity and so on.
Therefore, polymeric dyes are more promising than low
molecular dyes as colorants in nonlinear optical material
[21], biomedicine [22], jet-printing [23], especially poly-
mer materials, such as fiber, plastic and rubber [24–26].
Polymeric dyes can be achieved by introducing chromo-
phoric groups into the main chain or bound to the side
chain of polymers via chemical reactions [27].
In our previous work [28], an attempt was made to find a
way to convert WEPS into polymeric dyes in our group.
Three azo polymeric dyes had been synthesized via nitra-
tion, reduction, diazotization and coupling reactions from
WEPS. Firstly, 4-nitro polystyrene (PS-NO2) was prepared
from WEPS via nitration reaction. Then 4-amino polysty-
rene (PS-NH2) was obtained by reduction reaction of PS-
NO2. PS-NH2 was diazotized to obtain macromolecular
diazonium salt. By the coupling reactions between mac-
romolecular diazonium salt with different coupling com-
pounds, three azo polymeric dyes were finally prepared.
However, it was found that the color intensities of the
polymeric dyes prepared were low, which might be due to
the low chromophore contents in the molecular structures
of these dyes. In this study, a new modified synthetic route
for the preparation of polymeric dyes from WEPS was
presented. By chlorosulfonation, amidation, hydrolysis,
diazotization and coupling reactions, five polymeric azo
dyes (D1–D5) containing the sulfonamide group with dif-
ferent colors were prepared using WEPS as raw material.
The UV–Vis absorption properties, solubility and thermal
properties of these polymeric azo dyes were investigated.
Materials and methods
Materials
Waste expanded polystyrene was obtained from polysty-
rene foam used for packing. A supply of 4-acetamidoani-
line was purchased from the Cangzhou Ruidong Chemical
Industry Co., Ltd., while 2-naphthol and phenol were
provided by the Shenyang Chemical Reagent Factory, and
1-naphthylamine was obtained from the Shanghai Sillian
Chemical Plant. A supply of N-ethyl-3-cyano-4-methyl-6-
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hydroxy-2-pyridone and N-butyl-3-cyano-4-methyl-6-
hydroxy-2-pyridone were obtained from the Changzhou
Sanling Chemical Trade Co., Ltd.. Other chemical reagents
were analytical reagent grade and used as received.
Synthesis procedures
Synthesis of polystyrylsulfonyl chloride (I1)
A volume of 5.1 ml of chlorosulfonic acid was cooled to
below 5 °C, to which a solution of WEPS (2.00 g) in
chloroform was added dropwise with stirring. The mixture
was heated to 50 °C and stirred for 1 h. Then, a volume
of 1.4 ml of thionyl chloride was added and stirred at this
temperature for another 1 h. After cooling to room tem-
perature, the mixture solution was poured into ice deion-
ized water. The precipitate was filtered off and then washed
with ice deionized water until neutral. The product was
dried under vacuum at 80 °C to a constant weight. Yield:
86.14 %.
Synthesis of 4-acetamino-polystyrylsulfonamide (I2)
A mass of 1.00 g 4-acetamidoaniline was dissolved in
50.0 ml of acetone under reflux, and then cooled to the room
temperature. A solution of I1 (1.35 g) in 50.0 ml of acetone
was slowly added. After reacting at the room temperature for
1 h, the mixture was heated to 40 °C for another 2 h. The pH
of the reaction mixture was adjusted to 9–10 using 10 %
sodium carbonate solution during the reaction. The resulting
product was filtered off, washed with acetone to remove the
unreacted 4-acetamidoaniline, and dried under vacuum at
40 °C to a constant weight. Yield: 74.84 %.
Synthesis of 4-amino-polystyrylsulfonamide (I3)
A mass of 1.00 g I2 was added to 50.0 ml of 10 % sodium
hydroxide solution. After stirring for 3 h under reflux, the
mixture was cooled to the room temperature, and pH was
adjusted to near neutrality by 10 % hydrochloric acid
solution. The resulting product was filtered off, and dried
under vacuum at 80 °C to a constant weight. Yield:
92.22 %.
Synthesis of polymeric azo dyes (D1–D5)
The preparation procedure of polymeric azo dye D1 was
described as follows: A mass of 1.10 g I3 was added to a
mixture of 20.0 ml of deionized water and proper amount
concentrated hydrochloric acid under stirring, and cooled
to below 5 °C. Then a 30 % aqueous solution of sodium
nitrite (included 0.42 g sodium nitrite) was dropped slowly
into the mixture, keeping the temperature below 5 °C. The
J Mater Cycles Waste Manag (2014) 16:557–565
Ehrlich reagent was used to determine the end point of the
reaction, and then a proper amount of sulfamic acid was
added to remove the excess nitrous acid. The obtained
diazonium salt solution was kept below 5 °C and used
immediately in the coupling reaction.
A mass of 0.58 g 2-naphthol was dissolved in 10.0 ml of
10 % sodium carbonate solution and cooled to below 5 °C,
to which the diazonium salt solution was added dropwise
with stirring. The pH of the reaction mixture was adjusted
to 9–10 using 10 % sodium hydroxide solution and the
temperature was kept below 5 °C. The end point of the
reaction was determined by flushing ring testing method.
The resulting product was filtered off, washed with 10 %
sodium carbonate solution to remove the unreacted b-
naphthol, then washed with deionized water until neutral,
and dried under vacuum at 80 °C to a constant weight to
abtain the red polymeric dye D1. Yield: 78.77 %.
The synthesis methods of polymeric azo dyes D2–D5 are
similar to that of polymeric azo dye D1 except that the
coupling components are replaced by phenol, 1-naphthyl-
amine, N-ethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone,
and N-butyl-3-cyano-4-methyl-6-hydroxy-2-pyridone,
respectively.
Determination of the chlorosulfonyl group content of I1
The chlorosulfonyl group content of I1 was determined by
the neutralization method. The method is as follows: A
mass of 0.5000 g I1 was added to 65.0 ml of 0.1 mol l-1
sodium hydroxide solution. The mixture was heated to
reflux for 2 h and cooled to the room temperature. The
excess alkali was back-titrated with hydrochloric acid
standard solution using phenolphthalein as indicator.
In order to exclude the interference of the free acid in
the I1 sample to the determination of the chlorosulfonyl
group content, it is necessary to titrate the free acid in the
sample with sodium hydroxide standard solution. The
method is as follows: A mass of 0.5000 g I1 was added to
25.0 ml deionized water, stirred thoroughly, and then
titrated with sodium hydroxide standard solution using
methyl orange as indicator.
The content of chlorosulfonyl group of I1 could be
expressed by the number of moles of the chlorosulfonyl
group (–SO2Cl) per gram of I1 (expressed in units of
mmol g-1), which could be calculated according to the
following equation:
Content of SO2 Cl ¼ ð650:1N1 V1 N2 V2 Þ=ð20:5000Þ
Where N1 (mol l-1) and V1 (ml) are the concentration
and the consumed volume of the hydrochloric acid
standard solution in the back-titration of excess alkali,
respectively. N2 (mol l-1) and V2 (ml) are the
559
concentration and the consumed volume of the sodium
hydroxide standard solution in the titration of free acid,
respectively.
Measurements
Fourier transform infrared spectra (FTIR) were measured
on a Perkin-Elmer FTIR Spectrum One-B spectrometer in
the 4000–400 cm-1 region using KBr pellets. Ultraviolet–
visible (UV–vis) absorption spectra were recorded on a
Perkin-Elmer Lambda 35 Ultraviolet–visible spectropho-
tometer at room temperature. Thermal gravimetric analyses
(TGA) were performed on STA-409 PC simultaneous
thermal analyzer under nitrogen atmosphere in the region
of 50–800 °C with a heating rate of 10 °C min-1.
Results and discussion
Preparation of polymeric azo dyes
As shown in Fig. 1, five polymeric dyes were synthesized
using WEPS as raw material via chlorosulfonation, ami-
dation, hydrolysis, diazotization and coupling reactions. In
order to achieve the proper reaction conditions, the main
influence factors of each step reaction were investigated.
I1 was prepared from WEPS by chlorosulfonation
reaction using chlorosulfuric acid and thionyl chloride as
chlorosulfonation agents. WEPS firstly reacted with an
equal mole of chlorosulfuric acid to form polystyrene
sulfonic acid, and then polystyrene sulfonic acid obtained
further reacted with excess chlorosulfuric acid to yield the
target product I1. It was worth pointing out that thionyl
chloride played an important role in chlorosulfonation
reaction. Sulfuric acid was the main by-product in chlo-
rosulfonation reaction. Thionyl chloride could react with
the by-product sulfuric acid to form chlorosulfuric acid,
which was able to continually participate in the chloro-
sulfonation reaction as raw material. Additionally, thionyl
chloride could also react with the polystyrene sulfonic acid
to yield I1. The effects of the reaction temperature and
reaction time on the chlorosulfonation reaction of WEPS
were investigated. From Fig. 2, it can be seen that with the
increase in reaction temperature from 40 to 50 °C, the yield
and content of –SO2Cl of I1 increased from 62.13 to
86.14 % and 3.56 to 4.19 mmol g-1, respectively. The
results show that the increase of reaction temperature was
favorable to the chlorosulfonation reaction of WEPS.
However, when the reaction temperature continued to
increase from 50 to 60 °C, the yield of I1 was not
increased, and on the contrary decreased slightly, while, the
content of –SO2Cl obviously decreased from 4.19 to
2.13 mmol g-1. This was because too high a reaction
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Fig. 1 Synthesis of polymeric azo dyes (D1–D5)
Fig. 2 Effect of reaction temperature on yield and content of –SO2Cl
of I1. The inset table presents the corresponding experimental data.
Reaction conditions: 5.1 ml chlorosulfuric acid, 2.00 g WEPS, 1.4 ml
thionyl chloride, chloroform as solvent, reaction time 2 h
temperature might result in decomposition of I1 and the
formation of some by-products with high boiling points,
leading to the decrease yield and the low content of –
SO2Cl, and meanwhile deepening the color of the product,
which was observed during the experiment. On the other
hand, it can be seen from Table 1 that the yield and content
of -SO2Cl of I1 increased from 72.27 to 86.14 % and 3.47
to 4.19 mmol g-1, respectively, when the reaction time
increased from 1 to 2 h. However, too long a reaction time
(3 or 4 h) might cause the decomposition of the I1 and the
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Table 1 Effect of reaction time on yield and content of –SO2Cl of I1
Reaction Yield (%) Content of –SO2Cl
time (h) (mmol g-1)
1 72.27 3.47
2 86.14 4.19
3 79.59 3.06
4 83.66 2.53
Reaction conditions: 5.1 ml chlorosulfuric acid, 2.00 g WEPS, 1.4 ml
thionyl chloride, chloroform as solvent, reaction temperature 50 °C
occurrence of some side effects, resulting in the decrease
yield and the low content of –SO2Cl. The results above
suggested that the effects of the reaction temperature and
reaction time on the chlorosulfonation reaction of WEPS
had a similar trend on yield and content of –SO2Cl of I1,
and the appropriate reaction temperature and reaction time
were 50 °C and 2 h, respectively.
I2 was synthesized by amidation reaction between I1 and
p-acetamidoaniline using 10 % sodium carbonate solution
as acid binding agent and acetone as solvent. At the initial
reaction stage, the reaction temperature should not be too
high because I1 was easy to discompose at high tempera-
ture. For this reason, the reactants firstly reacted for 1 h at
the room temperature, and then the reaction temperature
was increased to higher temperatures for another period of
time in order to accelerate reaction speed. As shown in
Fig. 3, with the increase of the reaction temperature from
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reaction temperature or reaction time continuously

Fig. 3 Effect of a reaction temperature and b reaction time on yield
of I2. The inset table presents the corresponding experimental data.
Reaction conditions: 1.35 g I1, 1.00 g p-acetamidoaniline, 10 %
sodium carbonate solution as acid binding agent, acetone as solvent
30 to 40 °C (curve a), the yield obviously increased from
59.35 to 74.84 %, and with the increase of the reaction
time from 1 to 2 h (curve b), the yield increased from
65.16 to 74.84 %. However, the yield decreased when the
increased, which might be due to the hydrolysis of p-
acetamidoaniline in alkaline condition. Therefore, the
appropriate reaction temperature and reaction time of the
amidation reaction of I1 were 1 h at the room tempera-
ture, and then 2 h at 40 °C.
I3 was prepared by hydrolysis reaction of I2 in 10 %
sodium hydroxide solution for 3 h under reflux. Under the
above condition, the amide groups of 4-acetamino-poly-
styrylsulfonamide were hydrolyzed to amino groups and
the target product I3 could be obtained.
A macromolecular diazonium salt was obtained by the
diazotization reaction of I3 with sodium nitrite in the pre-
sence of hydrochloric acid. The reaction temperature was
kept below 5 °C to avoid decomposition of the diazonium
salt at high temperature. Three representative types of
coupling components, including phenolic (2-naphthol and
phenol), amine (1-naphthylamine), and heterocyclic com-
pounds (N-ethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone
and N-butyl-3-cyano-4-methyl-6-hydroxy-2-pyridone)
were chosen. By the coupling reaction of macromolecular
diazonium salt with these coupling agents, a series of
polymeric azo dyes (D1–D5) were prepared, as shown in
Fig. 1, and the synthesis results are summarized in Table 2.

Table 2 Synthesis results of polymeric azo dyes (D1–D5) from WEPS

Poymeric azo dye Coupling compound Dye structure

OH
OH
SO2NH N N
D1

OH
D2 SO2NH N N OH

NH2
SO2NH N N NH2
D3

CH3 CH3
CN CN
SO2NH N N
D4
HO O HO N O
C2H5
C2H5

CH3 CH3
CN CN
SO2NH N N
D5
HO N O HO N O
C4H9 C4H9

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Fig. 4 FTIR spectra of a I1, b I2, c I3, and d polymeric dye D1
FTIR spectral analysis of polymeric azo dyes
The FTIR spectra of I1, I2, I3 and polymeric azo dye D1 are
shown in Fig. 4a–d, respectively. The absorption peaks
located at 1385 and 1125 cm-1 in Fig. 4a were attributed
to the asymmetric and symmetric stretching vibrations of
S=O bond of –SO2Cl group, respectively, suggesting that I1
was obtained from WEPS by chlorosulfonation reaction
[29]. In Fig. 4b, two new peaks at 1325 and 1156 cm-1
belonging to the asymmetric and symmetric stretching
vibrations of S=O bond of –SO2NH– group, respectively,
appeared. Meanwhile, the absorption peaks at 1662 and
1512 cm-1 corresponding to the stretching vibrations of
C=O bond and the bending vibration of N–H bond of –
CONH– group, respectively, were detected. These results
indicated that p-acetamidoaniline had been successfully
attached onto the benzene ring of polystyrene backbone
and I2 was prepared. As shown in Fig. 4c, the two above
peaks characteristic absorption of –CONH– group were
absent, and alternatively, a new peak at 1638 cm-1
belonging to the bending vibration of N–H bond of NH2
group appeared, indicating that I3 was obtained from I2 by
the hydrolysis reaction. In Fig. 4d, the characteristic
absorption peak of amino group in Fig. 4c disappeared,
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while a new strong peak at 1504 cm-1 attributed to the
stretching vibration of –N=N– emerged, and moreover, the
peak at 1209 cm-1 corresponding to the stretching vibra-
tion of C–O bond of phenolic hydroxyl group appeared
[30]. These results confirmed that polymeric azo dye D1 (as
shown in Fig. 1) was successfully synthesized.
UV–vis absorption properties of polymeric azo dyes
Figures 5 and 6 present the UV–vis absorption spectra of
polymeric azo dyes D1–D5. The obtained maximum
absorption wavelength (kmax) values and the colors of these
dyes are listed in Table 3.
As seen in Table 3, the kmax values for polymeric azo
dyes D1, D2 and D3 are 470, 385 and 485 nm, respectively.
It is well known that the kmax value of dye depends on
electronic transitions in the entire conjugated system of dye
molecule, which is mainly determined by the size of the
conjugated system of dye molecule and the nature of the
substituents in the dye structure [31]. It could be seen from
Table 2 that dye D3 molecule had a longer conjugated
system than dye D2 due to the introduction of the naph-
thalene rings. Meanwhile, the electron donor ability of
amino groups on the para-position of the naphthalene rings
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in the dye D3 molecule is stronger than hydroxyl groups on
the para-position of the benzene rings in the dye D2.
Therefore, compared to dye D2, in the dye D3 molecule, the
p-electrons delocalization increased and the excitation
energy decreased, and thus electronic transitions were easy.
Consequently, dye D3 had the longer kmax than that of dye
D2, and thus displayed a deeper color than dye D2, as
shown in Table 3. For dyes D1–D3, as expected, the kmax
shifted to longer wavelengths and the colors deepened in
the order D2 (385 nm, deep yellow) \D1 (470 nm, red)
\D3 (485 nm, purplish red).
The molecular structure of polymeric azo dye D5 was
similar to that of polymeric azo dye D4 except that the
ethyl group attached to the nitrogen atom on the pyridine
ring in the dye D4 molecule was replaced by butyl group. It
is generally known that the electron donor ability of butyl
group is slightly stronger than that of ethyl group. As a
result, the kmax value of dye D5 showed small hypsochro-
mic shift (only 5 nm) than that of dye D4, and the dye D4
and D5 exhibited the similar color (orange red), as seen in
Fig. 6 and Table 3.
Based on the above discussion, it could be found that the
colors of these polymeric dyes could be tuned by choosing
different coupling agents to change the size of the conju-
gated systems and the type of the substituents in the
polymeric dye structures. Therefore, polymeric azo dyes
with various colors could be prepared from WEPS by
means of the synthesis method above, which was benefit
for satisfying the requirement for the application.

Fig. 5 UV–vis absorption spectra of polymeric dyes a D1, b D2, and

Table 4 Solubilities of polymeric azo dyes (D1–D5) from WEPS
c D3
Solvent D1 D2 D3 D4 D5

Toluene ? ? ? ? ?
DMF ? ? ? - -
DMSO ? ? ? - -
Trichloromethane ? ? ?- - -
Acetone - - ?- - -
Ethanol - - - - -
?, soluble; -, insoluble; ? -, soluble on heating

Fig. 6 UV–vis absorption spectra of polymeric dyes a D4 and b D5

Table 3 kmax values and colors of polymeric dyes (D1–D5) from

WEPS
Polymeric D1 D2 D3 D4 D5
azo dye

kmax (nm) 470 385 485 445 450

Color Red Deep Purplish Orange Orange
yellow red red red
kmax maximum absorption wavelength Fig. 7 TGA curves of polymeric dyes (D1–D5)

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Solubilities and thermal stabilities of polymeric azo
dyes
As shown in Table 4, all polymeric azo dyes prepared were
soluble in toluene at the room temperature based on the
principle of ‘‘similarity and intermiscibility’’. The dyes D1,
D2 and D3 could also solve in high polar solvents such as
N,N-dimethylformamide (DMF) and dimethyl sulfoxide
(DMSO) at the room temperature, while the azo dyes D4
and D5 were soluble neither in DMF nor in DMSO even be
heated. In ethanol, all polymeric azo dyes were not soluble.
The thermal stabilities of the polymeric azo dyes were
investigated by TGA in N2 atmosphere. The obtained TGA
curves of dyes (D1–D5) are presented in Fig. 7. It could be
seen that, these polymeric azo dyes had similar TGA
curves mainly due to their similar molecular structures, and
the 5 % weight loss temperatures of these dyes were all
higher than 350 °C. For example, the temperature at 5 %
weight loss of dye D1 was at about 357 °C. The TGA
results showed that the polymeric azo dyes prepared had
good thermal stabilities.
Conclusion
A feasible method for the preparation of polymeric azo
dyes from WEPS was proposed in this paper. By a series of
chemical reactions, using WEPS as raw material, five
polymeric azo dyes (D1–D5) containing the sulfonamide
group with different colors, including red, deep yellow,
purplish red, etc., were synthesized successfully. The col-
ors of the polymeric azo dyes could be tuned by using
different compounds as the coupling agents. The polymeric
dyes showed excellent thermal stabilities and good solu-
bilities in toluene at the room temperature. These poly-
meric dyes prepared are promising as colorants in plastic
and fiber materials. Therefore, the converting of WEPS
into polymeric azo dyes with practical applied values will
be of great benefit for protecting environment and the
sustainable development of resource.
Acknowledgments The authors acknowledge National Natural
Science Foundation of China (Grant No. 21306062), Zhejiang Pro-
vincial Natural Science Foundation of China (Grant No.
LQ13E030007) and Foundation of Zhejiang Educational Committee
(Grant No. Y201226209) for financial supports.
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