Synthesis, characterization and thermal degradation of cross-linked polystyrene using the alkyne-functionalized esters as a cross-linker agent by click chemistry method

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# S S S S S S S S S S S S S S S S S S S S

## Synthesis, characterization and thermal degradation of cross-linked polystyrene using the alkyne-functionalized esters as a cross-linker agent by click chemistry method

Hakan Akat 1 - and Fehmi Saltan 1,2

_1Department of Chemistry, Faculty of Science, Ege University, Bornova, Izmir, Turkey_

_2Department of Chemistry, Faculty of Science, Çankırı Karatekin University,_
_Merkez, Çankırı, Turkey_

_*hakan.akat@ege.edu.tr_

Abstract

In this study, it has been demonstrated that cross-linked polystyrene (CPS) was successfully prepared by using
click chemistry. For this purpose, firstly, poly (styrene-co-4 chloromethylstyrene) with 4-chloromethylstyrene was
synthesized. Secondly, alkyne-functionalized esters (dipropargyl adipate, dipropargyl succinate) were obtained using
propargyl alcohol, adipoyl chloride and succinyl chloride. Azide-functionalized polystrene (PS-N3) and dipropargyl
adipate (or dipropargyl succinate) were reacted in N,N-dimethylformamide for 24 h at room temperature to give CPS.
The synthesized polymer and compounds were characterized by nuclear magnetic resonance ( 1 H-NMR), gel permeation
chromatography (GPC), fourier transform infrared spectroscopy (FT-IR) and thermogravimetric (TG/DTG) analysis.
The surface properties were investigated by Scanning Electron Micrography (SEM).

Keywords: _polystyrene, cross-linked polymers, click chemistry, thermal degradation._

1. Introduction

In last years, polystyrene (PS) has managed to become
one of the world’s most widely used polymers. PS is one of
the three standard plastics (polyolefins, poly(vinyl chloride),
and PS), and PS can be applied in many fields, such as the
packaging of electrical equipment, apparatus, instruments,
and foods, thermal insulation materials for buildings and
cold storage, and disposable dinner service [1] . However
polystyrene do not offer the properties associated with
thermoset polymers, and hence its applications are
limited. Cross-linking of polystyrene is one approach to
improve the properties and consequently to access the
demanding regimes of high-tech applications. Crosslinked
polystyrene (CPS) have excellent mechanical properties
and good chemical stability. Their excellent performances
provide wide applications as packing materials for liquid
chromatography [2-5], as ion-exchange resins [6,7] and as imprinted
adsorbents for the selective separation of hazardous organic
compounds [8,9] . Cross-linking of PS is readily achieved by
the incorporation of a multifunctional monomer during
the polymerization process [10-15] . High-energy radiation or
photochemical irradiation has been used, but in addition
to the cross-linking both methods may also involve chain
scission that can result in polymer degradation or the
introduction of unwanted impurities. Alternative thermal
methods for the formulation of thermosetting materials
usually involve Diels-Alder and click chemistry reactions
which may suffer from the reversibility [16-17] . Yagci et al. [15]
synthesized polystyrene using click chemistry method.
Other methods involves classical cross linker agent as DVB
in literature. In our study, we introduce new strategy using
both click chemistry method and new crosslinker agents
(alkyne-functionalized esters).

2. Experimental

_2.1 Materials_

Styrene (S, 99%, Sigma-Aldrich Company, USA) and
4-chloromethylstyrene (CMS, ca. 60/40 meta/para isomer
mixture, 97%, Sigma-Aldrich Company, USA) were distilled
under reduced pressure before use. 2,2 Azobis(isobutyronitrile)
(AIBN, 98%, Sigma-Aldrich Company, USA) was recrystallized
from ethanol. Other solvents were purified by conventional
procedures. Triethylamine (98%, Sigma‑Aldrich Company,
USA) and dichloromethane (99.9%, HPLC grade, Sigma-Aldrich
Company, USA) were distilled from CaH2. Noxyl- free radical
(TEMPO, 99%, Sigma-Aldrich Company, USA) was used
as received Ethylenediaminetetraacetic acid (EDTA, 99%,
Sigma‑Aldrich Company, USA) N,N-dimethylformamide
(DMF 99%, Sigma-Aldrich Company, USA). Propargyl
alcohol (99%, Sigma-Aldrich Company, USA) were
used without any purification. Pyridine (anhydrous, 98%,
Sigma-Aldrich Company, USA). Adipoyl chloride (98%,
Sigma-Aldrich Company, USA). Succinyl chloride (95%,
Sigma-Aldrich Company, USA). 2,2’-bipyridine (reagent
plus >99%, Sigma-Aldrich Company, USA). Copper(I)
bromide(98%, Sigma-Aldrich Company, USA). Hydrochloric
acid (ACS reagent, 37%, Sigma-Aldrich Company, USA).

_2.2 Instrumentation_

1H-NMR (NMR, nuclear magnetic resonance) measurements
were recorded in CDCl3 (deuterium chloroform) with Si(CH3)4
as internal standard, using Varian AS-400 (400 MHz)
instrument. Fourier transform infrared spectroscopy (FTIR)
spectra were recorded on a PerkinElmer FTIR Spectrum

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One-B spectrometer. Molecular weights were determined by
gel permeation chromatography (GPC) instrument equipped
with a Waters styragel column (HR series 2, 3, 5E) with
THF as the eluent at a flow rate of 0.3 mL/min and a Waters
410 differential refractometer detector.
TG measurements of powders polymer samples
were obtained on PerkinElmer Diamond TA/TGA from
25 to 1000 °C and heating rate of 10 °C/min under constant
flow rate of 100 mL/min of nitrogen atmosphere. The sample
weights for all the experiments were taken in the range of
8–10 mg. All SEM images were obtained by using a field
emission scanning electron microscope Zeiss FE-SEM Supra
25 microscope under high vacuum at a voltage of 15.0 kV
with a working distance of 6.0 mm.

_2.3 Synthesis of poly(styrene-co-chloromethylstyrene)_

Poly(styrene- _co_ -4-chloromethylstyrene) (P(S- _co_ -CMS))
was synthesized as described previously [18] .

_2.4 Synthesis of polystyrene azide (PS-N3)_ _[19]_

A typical procedure for the preparation of PS-N3 from
10 mol % CMS containing P(S-co-CMS) is as follows:
P(S‑ _co_ -CMS) (1.0 g, 1.04 ×10 –4 mol) was dissolved in DMF,
and NaN3 (0.07 g, 1.01 ×10 –3 mol) was added. The resulting
solution was allowed to stir at 25 °C overnight and precipitated
in excess methanol/water mixture (1/1 by volume). 1 H NMR
(CDCl3): δ ppm) 7.40–6.20 (b, 9H), 4.25 (s, 2H) FTIR T%
(cm_1): 3060, 2924, 2096, 1681, 1601, 1492, 1453, 757,
698. Mn: 3500 g/mol PDI: 1.50.

_2.5 Synthesis of dipropargyl adipate (DPA, diprop-2-ynyl_
_adipate) and dipropargyl succinate (DPS, diprop-2-ynyl_
_succinate)_

Propargyl alcohol (2.01 g, 0.036 mol), pyridine
(2.69 g, 0.034 mol), and dry dichloromethane (20 mL)
were charged to a 50 mL round-bottom flask. The resulting
solution was maintained at 0 °C by means of a salt-ice bath.
A solution of adipoyl chloride (2.63 g, 0.017 mol) or succinyl
chloride (3.11 g, 0.017 mol) in 5 mL of dry dichloroethane
was added dropwise over 30 min. The solution was stirred
overnight at room temperature and then transferred to a
250 mL separatory funnel with the aid of a small amount of
dichloromethane. The dichloromethane solution was washed
with water (2×25 mL), 5% HCl (20 mL), and saturated
sodium bicarbonate solution (25 mL). The dichloromethane
solution was dried over MgSO4 and the mixture was filtered.
Organic phase was removed by evaporator. The product s
were dried under vacuum overnight. DPA: yield of 70%.

Table 1. Mol feed ratio of synthesized cross-linked polymers.

FTIR T% (cm –1 ): 3294 (HC≡ CH), 2920 (-CH2-), 2126
(≡C-H), 1736 (-C=O), 1259 (-C-O-) 1 H-NMR (CDCl3,
400 MHz, 25 °C, TMS): δ=1.76 (m, 4H, CH2), 2.45 (m, 4H,
CH2-CO), 2.55 (t, 2H, ≡C-H), 4.72 (d, 4H, O-CH2) ppm.
DPS:yield of 65%. FTIR T% (cm -1 ): 3289 (HC≡ CH), 2920
(-CH2-), 2128 (≡C-H), 1724 (-C=O), 1242 (-C-O-) 1 H-NMR
(CDCl3, 400 MHz, 25 °C, TMS): δ = 2.50 (m, 4H, CH2-CO),
4.40(d, 4H, O-CH2), 2.20 (t, 2H, ≡C-H).

_2.6 Preparation of the crosslinked polystyrene by using_
_DPA(C-PSA) and DPS(C-PSS)_

In a flask, PS-N3, DPA (or DPS), copper (I) bromide, 2,
2’-bipyridine and dry DMF were added. The flask was capped
with a septum and purged with dry nitrogen for 10 min.
The mixture was stirred overnight at room temperature. After
removing the catalyst by EDTA, functionalized polymer
was precipitated in methanol (200 mL), filtered, and dried
under vacuum overnight with a yield of 70% (mol feed
ratios are seen Table 1).

3. Result and Discussion

In our study, we first synthesized (P(S- _co_ -CMS)) and P-N3.
Following experiment was carried out for alkyne‑functionalized
esters (DPA and DPS). DPA and DPS were used to obtain
cross-linked polystyrene. CPS was synthesized via click
chemistry (Scheme 1). Chemical structure of both esters
and polymers were identified by several techniques such
as FT-IR, NMR, GPC, TG, DTG and SEM.

The FT-IR spectra of DPA;PS-N3;C-PSA65%;C-PSA12%
and DPS;PS-N3;C-PSS65%;C-PSS12% are shown in Figure 1
and Figure 2, respectively. According to this FT-IR spectra,
appearance of the -N3 stretching is clear at 2096 cm –1 and it
is notable that spectra of ADP and DPS show -H C≡ C H- ;
≡ C-H - peaks at around 3290;2120 cm -1 . After cross-linked
reaction between DPA(or DPS) and PS-N3, disappearance
of –N3 and alkyne peaks can be seen. These FT-IR data
show successful of PS-N3, CPS, DPA and DPS synthesis.
On the other hand, they are also supported by 1 H-NMR.
From the 1 H NMR spectra of synthesized DPA and DPS, it
is observed that -C≡ H protons signals at 2.40 and 2.20 ppm,
respectively. O-C H2 protons are observed at 4.72(DPA) and
4.40(DPS) ppm. -C H2 -CO protons can be seen at 2.45 ppm
and 2.50 ppm.

Thermal behaviour and thermal stability of the synthesized
CPS is investigated by TG measurement. TG curves and
the corresponding derivative curves (DTG) for cross-linked
polystrene are shown in Figure 3 and Figure 4, respectively.
The derivative of the thermogram with respect to temperature,

Compound

(C)

65% Azide Containing PS
CuBr bipyridine C PS-N3 DMF

DPA 6.6×10 –4 mol 0.094 g 1.3×10 –3 mol 0.2 g 4.12×10 –4 mol 0.092g 3.3×10 –4 mol 0.1 g 5 ml
DPS 3.3×10 –4 mol 0.0473g 6.6×10 –4 mol 0.10g 2,10×10 –4 mol 0.041g 1.68×10 –4 mol 0.05g 5ml
Compound 12% Azide Containing PS

(C)

12% Azide Containing PS
CuBr bipyridine C PS-N3 DMF

DPA 0.3×10 –4 mol 0.042 g 0.6×10 –4 mol 0.093g 1.87×10 –4 mol 0.041g 1.5×10 –4 mol 0.05g 5 ml
DPS 0.3×10 –4 mol 0.042 g 0.6×10 –4 mol 0.093g 1.87×10 –4 mol 0.036g 1.5×10 –4 mol 0.05g 5ml

Scheme 1. General procedure for the synthesis of alkyne functionalized ester containing CPS via click chemistry.

also known as a differential thermogram or DTG, indeed
shows the maximum rate of polymer decomposition
(Tmax). TG thermogram under N2 atmosphere revealed
that C-PSA65% and C-PSS65% degradation takes place in
three stages, C-PSA12% and C-PSS12% degradation takes
place in two stages.

The first stage for the C-PSA65% being at a temperature
around 312 °C that corresponds to a very small mass loss

of about 10%. The second occurs at about 378 °C that
corresponds to mass loss of about 25% and the last stage
occurs at about 600 °C that corresponds to mass loss of about
50%. C-PSA12% has two main decomposition stages. First
one appears to begin around 291 °C and stop around 414 °C.
The second one appears to begin around 390 °C and stop
around 526 °C. The remaining mass without degradation
of C-PSA65% is higher than C-PSA12%. When compared to

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Figure 1. Comparison of FT-IR spectra of DPA;PS-N3;C-PSA65%;C-PSA12%.

Figure 2. Comparison of FT-IR spectra of DPS;PS-N3;C-PSS65%;C-PSS12%.

Figure 3. Comparison of TG curves of PSS65%;C-PSS12% and C-PSA65%;C-PSA12%.

Figure 4. Comparison of DTG curves of C-PSA65%;C-PSA12% and PSS65%;C-PSS12%.

C-PSS65% and C-PSS12%, it is observed that C-PSS65% more
stable then C-PSS12%.

The first, second and third degradation stages of
C-PSS65% begin 225, 296, 396 °C and the mass loss is about
10%, 20% and 75%, respectively. C-PSS12% curves show
two degradation stages which temperatures are 220 o C and
412 o C. When thermal degradation curves of polystyrene
compared with crosslinked polystyrene, the char yield of
the thermally cured polystyrene was about 40% and much
higher than PS (0.0%) in literature [15,20-22] . We also observed
that thermal stability of CPS increases with the chain length
of alkyne functionalized esters used (All Tmax values are
shown in Table 2).

Table 3 displays the SEM micrographs obtained
before and after cross-linked PS-N3/DPA/DPS. The SEM
microphotographs of PS-N3 show that, most of the
microspheres are unregularly spherical, and the interface
is clear and smooth. The average particle size is between
1500μm-680 nm in diameter. The SEM images of various
crosslinked PS, it could be visualized that no inert layer
was formed on the surfaces of the C-PSS and C-PSA after
cross-linked between PS-N3 and alkyne functionalized
esters. The images also indicate an increase in compact

packing with increasing DPA or DPS content, suggesting
the formation of a rigid interpenetrating network formation
and increased crosslinking.

4. Conclusions

In conclusion, we introduce an effective strategy to
synthesize a novel cross-linked polystyrene(C-PS) by
using click chemistry. The Cross-linking reaction was

Table 2. Tmax values of the synthesized cross-linked polystyrene.

CPS C-PSS C-PSA
N3% 12 65 12 65
Tmax( o C) 225 235 351 335
412 320 423 387

- 421 - 629

Table 3. SEM micrographs of PS-N3, C-PSA65%;C-PSA12% and
C-PSS65%-C-PSS12%.

Sem micrographs
Azid%

of PS-N3

Sem micrographs of CPS after

crosslinked
C-PSA C-PSS

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carried out under the condition of low temperature and
we used the synthesized alkyne-functionalized esters as a
cross-linker. According to data obtained from TG and DTG
curves, chain length of alkyne functionalized esters plays
important role for thermal stability and in char yield . PS
cured in this way exhibited much more thermal stability than
those of structurally similar cross-linked polymers. Surface
morphologies of CPS changed when used cross‑linker
(DPA or DPS) of different chain lengths.

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_Received: Oct. 03, 2014_

_Revised: Feb. 26, 2015_
_Accepted: Mar. 20, 2015_

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