A facile strategy to improve the encapsulation efficiency of polymer

microcapsules containing water-soluble salt cores

Mingming Zuo,1,2 Long Zhang,1 Xuzhou Yuan,2 Yuchen Li,2 Tianqing Liu 1
1
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People’s Republic of China
2
Jiangsu Key Laboratory of Advanced Functional Materials, Changshu Institute of Technology, Suzhou 215500,
People’s Republic of China
Correspondence to: T. Liu (E - mail: tqliu@yzu.edu.cn)

ABSTRACT: To increase the encapsulation efficiency of microcapsules composed of water-soluble salt cores and hydrophobic material
shells, we herein reported a facile and versatile strategy to improve the hydrophobicity of water-soluble salts [i.e., ammonium persul-
fate (APS)] by surface modification of APS using oleic acid or silane coupling agent, respectively. The results confirmed that the
hydrophobicity of the two modified APS had been successfully improved compared with that of non-modified APS. Moreover, the
two modified APS could be effectively encapsulated into hydrophobic polystyrene and the encapsulation efficiency of the resulting
microcapsules goes up significantly. This study was expected to drive progress in the preparation technology of microcapsules which
comprise water-soluble salts as cores and hydrophobic polymer materials as shells in many industrial application fields. V C 2017 Wiley

Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45294.

KEYWORDS: composites; drug delivery systems; grafting; packaging

Received 8 January 2017; accepted 4 May 2017

DOI: 10.1002/app.45294

INTRODUCTION
Microcapsules composed of water-soluble salts as cores have
been applied to many industrial fields. For instance, microcap-
sules containing water-soluble calcium zinc phosphate were
employed as corrosion protective agents in marine equipment
fields.1 Water-soluble ammonium polyphosphate was encapsu-
lated in microcapsules to improve the thermal stability and
flame retardancy of epoxy resin in materials fields.2 Microcap-
sules comprising ammonium persulfate (APS) cores with con-
trolled release properties were the most promising gel breaker
in oil and gas fields because they could delay the degradation
time of fracturing fluid and enhance the level of tertiary oil
recovery.3 Solvent evaporation and in situ polymerization meth-
ods were often used for synthesizing microcapsules composed
of water-soluble salts as cores.4–7 Hydrophobic materials were
chosen as shells of the microcapsules to retain the cores’ water
solubility.8–10 However, the difference of surface energy between
the water-soluble cores and hydrophobic shells was distinct.11,12
Accordingly, the cores were difficult to be encapsulated into
hydrophobic materials efficiently; the encapsulation efficiency of
the resulting microcapsules was low. This disadvantage limited
the development and practical application of the microcapsules
in many industrial fields.
One way to narrow the difference of surface energy between the
water-soluble salt cores and hydrophobic shells was to improve
the hydrophobicity of water-soluble salts by surface modifica-
tion. So far, there had been extensive studies on surface modifi-
cation of inorganic materials.13–18 However, little attention had
been paid to increase the encapsulation efficiency of microcap-
sules, which contains water-soluble salt cores, by improving the
hydrophobicity of salts.
Herein, we demonstrated a facile strategy to improve the surface
hydrophobicity of water-soluble salts (i.e., APS) by surface mod-
ification of APS using oleic acid (OA) and silane coupling
agent, respectively. The hydrophobic effect of the two modified
APS salts was investigated by studying their soluble time profiles
in water and sedimentation time profiles in liquid paraffin.
Both modified APS salts displayed good hydrophobicity. We
also demonstrated that the modified APS could be efficiently
encapsulated into hydrophobic polystyrene and the encapsula-
tion efficiency of the resulting microcapsules increased signifi-
cantly compared with the microcapsules containing non-
modified APS. Our strategy provided a facile and effective way
to solve the problem of incompatibility between water-soluble
salts and hydrophobic polymer materials. Moreover, this facile
strategy could be readily extended to the preparation for many

C 2017 Wiley Periodicals, Inc.

V

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Figure 1. (a) The molecular formulae of silane coupling agent (KH-570)
and OA, respectively. The action mechanism of KH-570 (b) and OA (c)
on APS surface. Others: (I) hydrolysis, (II) dehydration condensation
reaction, (III) hydrogen bond formation, (IV) covalent bond forming.
[Color figure can be viewed at wileyonlinelibrary.com]
other microcapsules composed of water-soluble cores, such as
corrosion inhibitor, catalysts, and phase-change materials.
Figure 3. FTIR spectra of (a) non-modified APS, (b) OA-modified APS,
(c) silane-modified APS, and (d) KH-570. [Color figure can be viewed at
wileyonlinelibrary.com]
(CH2CCH3COO(CH2)3Si(OCH3)3, KH-570) was supplied by
Yizheng Tianyang Chemical Co. Ltd., China. All the chemicals
were used as received.

EXPERIMENTAL Procedures of Surface Modification

Materials
Analytical reagents of APS (ground in mortar before use),
xylene, ethanol (95% purity), isopropanol, OA, petroleum ether
(90–120 8C), trichloromethane, polyoxyethylene sorbitan mono-
oleate (Tween 80), styrene (St), and 2,20 -azobis(2-methylpropio-
nitrile) (AIBN) were all purchased from Sinopharm Chemical
Reagent Co. Ltd., China. Technical grade silane coupling agent
Surface modification of APS with OA (denoted as OA-modified
APS): In a typical synthesis, APS (10.0 g) was added to a mix-
ture composed of OA (0.5 g) and xylene (50.0 g). The mixture
was then heated at 80 8C for 8 h at a constant stirring rate
(500 rpm). After cooling to ambient temperature, the obtained
products were washed with ethanol twice to remove residual
OA.

Figure 2. FE-SEM images of (a) APS particles, (b) a single APS particle surface, (c) OA-modified APS particles, (d) magnified images of OA-modified
APS particles, (e) silane-modified APS particles, (f) a single silane-modified APS particle.

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Figure 4. EDS patterns of (a) non-modified APS, (b) OA-modified APS,
and (c) silane-modified APS. [Color figure can be viewed at wileyonlineli-
brary.com]
Surface modification of APS with silane coupling agent (denoted
as silane-modified APS): Briefly, APS (10.0 g) was introduced
into a jacketed stainless steel reactor equipped with a reflux
condenser, a thermocouple, and a stainless-steel stirrer. Then
the reactor was heated at a constant stirring rate (4000 rpm).
When the reaction temperature reached 90 8C, a mixture of
KH-570 (0.2 g) and isopropanol (0.4 g) was slowly injected into
the reactor (about 10 min). The reaction was proceeded further
at 90 8C for 0.5 h. After cooling to ambient temperature, the
reaction products were washed with xylene three times to
remove the excess KH-570.
Preparation of Microcapsules Containing Modified APS
The synthesis of microcapsules composed of modified APS as
cores and hydrophobic polystyrene as shells was conducted as
follows. First, a mixture including petroleum ether (40 mL), tri-
chloromethane (10 mL), modified APS (5.0 g), and Tween 80
(0.15 g) was introduced to a 100 mL glass reactor at room
temperature. Second, the monomers of St (3.5 g) and AIBN
Table I. Elemental Composition on Surfaces (%) of Non-Modified APS, OA-Modified APS, and Silane-Modified APS Determined from EDS
Sample N (%) O (%)
Non-modified APS 17.35 66.49
OA-modified APS 11.44 68.56
Silane-modified APS 15.05 63.44
WWW.MATERIALSVIEWS.COM 45294 (3 of 8)
(0.15 wt % of St) were added to the mixture and stirred at
200 rpm for 1.5 h using a mechanical stirrer to ensure the
monomers were absorbed on the modified APS surface effec-
tively. Finally, the mixture was heated up to 70 8C and stirred
further for 6 h to obtain microcapsules with modified APS as
cores and polystyrene as shells. The resulting microcapsules
were washed twice with distilled water and ethanol, respectively,
to remove the non-encapsulated cores.
Characterizations
Field emission scanning electron microscope (FE-SEM) images
of pure and modified APS were recorded by a FE-SEM (S-4800,
Japan). The Fourier transform infrared spectroscopy (FTIR)
spectra (Nicolet-740, United States) were employed to record
the characteristic absorption peak of the modified APS. The
sample was ground with spectroscopic-grade potassium bromide
(KBr), and the wavenumber range was set from 400 to
4000 cm21. X-ray powder diffraction (XRD) pattern of sample
was determined by a German Bruker AXS D8 ADVANCE X-ray
diffractometer with a tube voltage of 45 kV. Transmission elec-
tron microscopy (TEM) characterizations of the samples were
performed on a TEM (TECNAI-12, Philips, the Netherlands).
The hydrophobicity of the modified APS was assessed by inves-
tigating their time profiles including sedimentation in liquid
paraffin and dissolution in water. The contact angles of water
on the modified APS surface were analyzed through a KSV
CAM200 optical contact angle measurement instrument. The
encapsulated efficiency of microcapsules was calculated by using
extraction method with water as solvents.19 Based on the initial
total weight (M1, the dry microcapsule samples) and residual
weight (M2, the samples were ground and washed with distilled
water three times) of microcapsule samples, moreover, knowing
the initial weight (M3) of APS which was used for synthesizing
microcapsules, the encapsulated efficiency of the microcapsules
(Em) was obtained as follows:
M1 2M2
Em 5 3100% (1)
M3
RESULTS AND DISCUSSION
Formation Mechanism and Surface Morphology of Modified
APS
The interaction process between APS and KH-570 is shown in
Figure 1(b). KH-570 undergoes hydrolysis first, whereby the
SiOCH3 groups are converted into SiAOH groups. Second, KH-
570 forms oligomeric entities after dehydration condensation of
SiAOH groups. Third, the SiAOH groups of oligomeric entities
interact with hydroxyl groups of APS surface to form hydrogen
bond.20,21 Finally, the hydrophobic group of KH-570 is grafted
onto the APS surface through covalent bonds after drying.22 As
S (%) C (%) Si (%)
16.16 0 0
13.19 6.81 0
14.67 1.08 5.76
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Figure 5. XRD patterns of APS: (a) non-modified, (b) OA-modified, and
(c) silane-modified. [Color figure can be viewed at wileyonlinelibrary.
com]
observed in Figure 1(c) OA was adsorbed onto the APS surface
via covalent bonding from a Lewis acid–base reaction.23
The FE-SEM images (Figure 2) show that the original geometri-
cal amorphous structures of APS particles are preserved after
being treated with OA [Figure 2(c)], however they are con-
nected to each other by pellicular materials [Figure 2(d)],
thereby indicating that the APS surface can be coated with OA.
When APS particles are modified by KH-570 [Figure 2(e,f)],
the modified APS surface appear compact “flaky-like” materials
compared with that of pure APS particles [Figure 2(a,b)].
Results indicate that hydrophobic groups of KH-570 could be
grafted onto APS surface via chemical coupling.
Components of OA-Modified APS and Silane-Modified APS
The FTIR spectra of APS modified with OA and KH-570 is
shown in Figure 3. The characteristic absorption peaks of APS
observed at 1060 and 1400 cm21 are attributed to the sulfate
group [Figure 3(a)].19 These characteristic APS peaks are also
observed in both OA-modified APS [Figure 3(b)] and silane-
Figure 6. Photographs of (a) silane-modified and (b) OA-modified APS in distilled water after preserved for different time. The content of KH-570 and
OA are 2 and 5 wt %, respectively. [Color figure can be viewed at wileyonlinelibrary.com]
WWW.MATERIALSVIEWS.COM 45294 (4 of 8)
modified APS [Figure 3(c)]. The broad stretching vibration peak
at 1650–1750 cm21 is assigned to the carboxyl group of OA [Fig-
ure 3(b)].24–26 The absorption peaks of asymmetry stretching
vibration of CAH at 2971, 2927 cm21,20,27 which exist in the
spectra of Figure 3(c), are attributed to KH-570 [Figure 3(d)].
Figure 4 shows two-dimensional scanned energy-dispersive X-ray
spectroscopy (EDS) patterns of non-modified APS, OA-modified
APS, and silane-modified APS surfaces. The N, O, and S ele-
ments are detected on the surface of non-modified APS salts,
which are attributed to APS, (NH4)2S2O8. C and Si elements are
additionally detected in the EDS spectra of OA-modified APS
and silane-modified APS. Thereby it indicates that OA and KH-
570 are successfully grafted onto the APS surface.11
Table I shows the elemental compositions of non-modified APS,
OA-modified APS, and silane-modified APS. Non-modified APS
is constituted of 17.35% N, 66.49% O, and 16.16% S, which is
consistent with the theoretical values (16.7% N, 66.6% O, and
16.7% S). The contents of N and S in OA-modified APS are
11.44% and 13.19%, slightly lower than those of non-modified
APS. In contrast, the contents of C and O (6.81% and 68.56%)
in OA-modified APS are higher than those of non-modified
APS. The EDS pattern signals of silane-modified APS are mostly
unchanged compared with non-modified APS, except for a
prominent EDS signal of 5.76% Si atom (owing to the addition
of KH-570).28
XRD pattern of non-modified APS, OA-modified APS, and silane-
modified APS is shown in Figure 5. The modified APS salts (treated
with either OA [Figure 5(b) or KH-570 [Figure 5(c)] displays typi-
cal APS peaks, suggesting that the APS structure is mostly
unchanged after being modified by OA or KH-570.
Sedimentation Time Studies of OA-Modified APS and
Silane-Modified APS
APS particles are water soluble salts. Therefore, the dissolving
capacity of the modified APS salts in water can be performed to
evaluate their surface hydrophobicity. As shown in Figure 6, the
solubility of the two modified APS salts has no distinct
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Figure 7. The sedimentation time (a) and photographs (b) of silane-modified APS and OA-modified APS in liquid paraffin. The content of KH-570 and
OA are 2 and 5 wt %, respectively. [Color figure can be viewed at wileyonlinelibrary.com]

Figure 8. Contact angles of water on (a) OA-modified APS, (b) silane-modified, and (c) non-modified APS. Others: APS samples are pressed into sheet
shapes by tableting machine before experiments.

Figure 9. Schematic illustration of the synthesis of APS at polystyrene microcapsules. [Color figure can be viewed at wileyonlinelibrary.com]

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Figure 10. FE-SEM images of microcapsules with (A) OA-modified APS and (B) silane-modified APS as cores and hydrophobic polystyrene as shells. (A,B,
insets) Corresponding transmission electron images of the microcapsule samples. (C) The encapsulation efficiency of microcapsules prepared with different
APS as cores: (a) non-modified APS, (b) OA-modified APS, and (c) silane-modified APS. [Color figure can be viewed at wileyonlinelibrary.com]

difference at the early stages (<5 s). At 40 s, the residual amount The surface hydrophobicity of OA-modified APS and silane-
of OA-modified APS is lower than that of silane-modified APS. modified APS are all improved significantly compared with that
It indicates that OA-modified APS displays poorer hydrophobic- of non-modified APS. Moreover, the contact angle of water on
ity than silane-modified APS. This may attribute to the fact that silane-modified APS (u 5 93.78) is higher than that on
OA physically adsorbs onto APS surface through a Lewis acid– OA-modified APS (u 5 69.68). These results are in accordance
base reaction, rather than that KH-570 chemisorbs onto APS sur- with the obtained results of Figures 6 and 7.
face via covalent bonds. After 80 s, all OA-modified APS salts
and most silane-modified APS salts are dissolved in water. This Preparation of Microcapsules Containing Modified APS
phenomenon shows that although KH-570 can increase the A schematic illustration of the preparation of APS at polysty-
hydrophobicity of water-soluble APS salts significantly, APS salts rene microcapsules is shown in Figure 9. APS is firstly modified
are not thoroughly covered with KH-570. In other words, only by OA or KH-570, and then styrene monomers are absorbed on
partial APS surface are modified with KH-570.29 These results the modified APS surface effectively in a mixed solvent com-
are consistent with those shown in Figure 2. posed of petroleum ether and trichloromethane. Finally, the
monomers are initiated by APS to form the shells of
Water-soluble APS salts cannot form a suspension in nonpolar
microcapsules.
solvent (i.e., liquid paraffin), thus we can further verify the sur-
face hydrophobicity of the modified APS by observing their sed- Microcapsules prepared by using the modified APS as cores and
imentation time and suspension in liquid paraffin. As shown in hydrophobic polystyrene as shells through in situ polymeriza-
Figure 7(a), the sedimentation time of silane-modified APS is tion method are shown in Figure 10. The surface of the two
longer than that of OA-modified APS. This indicates that the modified APS is all covered with rough membrane materials
surface hydrophobicity of silane-modified APS is better than [Figure 10(A,B)]. TEM images of the microcapsules [insert in
OA-modified APS. From an economical viewpoint, the opti- Figure 10(A,B)] display typical core–shell structure. Results
mum dosages of KH-570 and OA are 2 and 5 wt %, respec-
tively. From the sedimentation time curves of Figure 7(a), we
also noticed that if the dosages of KH-570 exceeds 4 wt %, the
sedimentation time of silane-modified APS will decrease. How-
ever, when the dosages exceed 6 wt %, the sedimentation time
will increase again. This phenomenon can be explained as
follows: if the dosages of KH-570 range from 2 to 4 wt %,
KH-570 forms a uniform monolayer on the APS surface. If the
dosages exceed the saturated adsorption quantity of APS, resid-
ual KH-570 will be adsorbed onto the KH-570 previously
formed layer.23 Results show that the polarity of silane-modified
APS can be influenced by the dosages of KH-570.
Figure 7(b) shows the photographs of the modified APS salts
mixed with liquid paraffin. Both modified APS salts display
good suspension and dispersion in liquid paraffin. The sedi-
mentation time of the modified APS salts is consistent with the
results of Figure 7(a).
The contact angles of water on OA-modified APS, silane- Figure 11. FTIR spectra of (a) APS and (b) APS at polystyrene microcap-
modified APS, and non-modified APS are shown in Figure 8. sules. [Color figure can be viewed at wileyonlinelibrary.com]

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Figure 12. XRD patterns of (a) APS and (b) APS at polystyrene micro-
capsules. [Color figure can be viewed at wileyonlinelibrary.com]
indicate that both OA-modified APS and silane-modified APS
are successfully encapsulated into hydrophobic polystyrene. The
encapsulation efficiency of the resulting microcapsules is 71%
and 83.5%, respectively, which is higher than the microcapsules
containing non-modified APS (37.5%) [Figure 10(C)]. These
obtained results clearly show that APS salts with enhanced sur-
face hydrophobicity can effectively increase the encapsulation
efficiency of the relevant microcapsules.
FTIR spectrum of the corresponding APS at polystyrene micro-
capsules is shown in Figure 11. The characteristic absorption
peaks of APS exist in the microcapsules. Moreover, there are
many characteristic absorption peaks of polystyrene. The peaks
at 695, 759 cm21 are attributed to flexural vibrations (dCAH)
of benzene ring, 1406, 1458, 1612 cm21 are assigned to benzene
ring mCAC vibrations, and 2842, 2954 cm21 belonged to
mCAH of saturated ACAHA, while 3016 cm21 corresponds to
mCAH of benzene ring.
XRD pattern of APS and APS at polystyrene microcapsules is
displayed in Figure 12. The typical crystal diffraction peaks of
microcapsules are consistent with APS. This result suggests that
the crystal structure of APS is not changed during its coating
Figure 13. TGA diagram of APS at polystyrene microcapsules.
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process and APS is suitable for being encapsulated into polysty-
rene shell.
Figure 13 shows the thermogravimetric analysis (TGA) result of
the synthesized microcapsules from 50 to 800 8C in nitrogen.
The initial weight loss of 7.64% up to 180 8C is attributed to
the evaporation of adsorbed water. Between 181 and 395 8C,
there is one big weight loss of 50.71%, which is due to decom-
position of polystyrene, indicating the formation of polymer in
the APS surface. The residual weight of 34.01% could be caused
by decomposition of APS.
CONCLUSIONS
The surface hydrophobicity of water-soluble APS salts was suc-
cessfully improved after being modified by OA or KH-570.
Moreover, the two modified APS could be easily encapsulated
into hydrophobic polystyrene. Compared with that of the
microcapsules with unmodified APS as cores (37.5%), the
encapsulation efficiency of microcapsules with modified APS as
cores was increased a lot (71% and 83.5%, respectively) as well.
The strategy provided in this paper was readily to be applied in
synthesizing other water-soluble core microcapsules, such as
water-soluble corrosion inhibitor (sodium nitrite), catalysts
(quaternary ammonium hydroxide), and phase-change materials
(calcium chloride hexahydrate). This paper was also expected to
promote the development of the preparation technology of
water-soluble core microcapsules in many industrial application
fields.
ACKNOWLEDGMENTS
For this work, authors acknowledge the support of National
Natural Science Foundation of China (20573091), Scientific Research
Foundation for Advanced Scholars (XZ1520), and the Testing
Center of Yangzhou University for Materials’ Characterization.
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