Polymer Degradation and Stability 94 (2009) 558–565

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Polymer Degradation and Stability

journal homepage: www.elsevier.com/locate/polydegstab

The effect of phosphorus content on the thermal and the burning properties of
cotton fabric coated with an ultrathin film of a phosphorus-containing polymer
Ampornphan Siriviriyanun a, Edgar A. O’Rear b, Nantaya Yanumet a, *
a
The Petroleum and Petrochemical College, Chulalongkorn University, Soi Chula 12, Phyathai Road, Patumwan, Bangkok, Thailand
b
School of Chemical, Biological and Materials Engineering, University of Oklahoma, Norman, OK 73019, USA

a r t i c l e i n f o a b s t r a c t

Article history: The effect of phosphorus content on thermal degradation and burning behavior of poly(acryloyloxyethyl
Received 26 November 2008 diethyl phosphate) or PADEP-coated cotton was studied. The results showed that PADEP-coated cotton
Received in revised form prepared by admicellar polymerization using hexadecyltrimethylammonium bromide (HTAB) as
12 January 2009
a surfactant has higher amounts of phosphorus than that prepared using dodecyltrimethylammonium
Accepted 19 January 2009
Available online 14 February 2009
bromide (DTAB). Higher phosphorus content led to lower decomposition temperatures and greater
amounts of char formation after thermal degradation. The effectiveness of the amount of phosphorus on
the burning behavior of the treated cotton was investigated by an ASTM flammabilty test. In the case of
Keywords:
Phosphorus content PADEP-coated cotton prepared with DTAB, the flame spread slowly and extinguished with char formation
Cotton on the fabric. For untreated cotton however, the flame spread quickly and burned the fabric entirely
Admicellar polymerization without char formation. Cotton coated with PADEP using HTAB exhibited self-extinguishing behavior
Burning behavior after removing the ignition source. Decrease in decomposition temperature, increase in char formation
Thermal degradation and the burning behavior of PADEP-coated cotton are all consistent with phosphorus content on the
treated fabric.
Ó 2009 Elsevier Ltd. All rights reserved.

1. Introduction
At present, the use of phosphorus-containing flame retardant
for cellulose is preferred over a halogen-containing flame retardant,
as the latter releases smoke and toxic gases during combustion [1].
Many studies indicate that phosphorus-containing flame retar-
dants act by phosphorylation of cellulose at C-6 hydroxyl group of
the anhydroglucose unit, thus blocking the formation of levoglu-
cosan and reducing the production of combustible gases and
increasing the amount of char formation [2,3]. Schwenker and
coworker showed that the prevention of levoglucosan formation
would decrease the flammability of cellulose [4]. Many approaches
have been developed to deposit a phosphorus-based flame retar-
dant onto cellulose fiber such as the pad/dry/cure technique, graft
copolymerization to cellulose, or in situ polymerization of mono-
mer which can form three dimensional network in or on fibers
[5,6]. Many studies show that flame retardant efficiency depends
on the amount of phosphorus content on the treated cellulose
[5,7,8]. To obtain a good flame retardant efficiency, the effective
treatment requires a large amount of flame retardant to be applied
to the cellulose fiber, and this may result in strength reduction of
* Corresponding author. Tel.: þ66 2 675 9970; fax: þ66 2 215 4459.
E-mail address: ynantaya@yahoo.com (N. Yanumet).
the treated cellulose fibers [3,5]. Modification of cotton with thin
films containing phosphorus has been proposed for flame retard-
ancy. For example, Cireli et al. recently reported the use of phos-
phorus doped SiO2 thin film applied by a sol–gel process [9]. In this
paper, we examine the thermal degradation and burning behavior
of cotton fabric coated with a phosphorus-containing thin film
applied by the process of admicellar polymerization.
Admicellar polymerization process is a novel method that can be
used to form an ultrathin polymer film on a substrate surface with
the aid of a surfactant [10]. Generally, admicellar polymerization
process consists of three basic steps as shown in Fig. 1: admicelle
formation, adsolubilization of the monomer into the admicelle, and
admicellar polymerization to form a thin polymer film on the
substrate surface. Usually a fourth step is introduced to remove the
outer-layer surfactant to expose the polymeric film on the substrate
surface. This technique has been used to form various types of
polymer films on cellulosic fibers to modify the fabric properties
[11–14]. It has been found that films formed through this process are
nanoscale in dimension and possess good durability [14–16].
Admicellar polymerization represents a new approach to depositing
a phosphorus-containing flame retardant onto the cellulose fiber.
In previous work, it has been found that favorable performance of
admicellar-treated cellulose fibers depends on the amount of poly-
mer formed on the fiber surface [14]. Attempts to increase the
amount of polymer formation on the substrate surface have

0141-3910/$ – see front matter Ó 2009 Elsevier Ltd. All rights reserved.
doi:10.1016/j.polymdegradstab.2009.01.014
 A. Siriviriyanun et al. / Polymer Degradation and Stability 94 (2009) 558–565 559

generally been made by increasing the amount of monomer added
to the system. However, it has also been known that, in admicellar
polymerization, the molecular structure of the surfactant used in the
process can also influence the extent of polymer formation [17–19].
In the present work, two types of quarternary ammonium cationic
surfactants with different hydrocarbon chain lengths were used in
carrying out admicellar polymerization. The thermal degradation
and burning behavior of the treated cotton were investigated by
using thermal gravimetric analysis and the burning test.
2. Experimental
2.1. Materials
Dodecyltrimethylammonium bromide (DTAB) and hexadecyl-
trimethylammonium bromide (HTAB), used as the surfactants,
were purchased from Aldrich. 2,20 -Azobisisobutyronitrile (AIBN)
(97%), used as initiator, came from Aldrich as well. Absolute ethyl
alcohol, sulfuric acid (96%), and hydrogen peroxide (H2O2) (30%)
were obtained from Mallinckrodt, Carlo Erba Reagenti, and Ajax
Finechem, respectively. All chemicals were used as received. The
phosphorus-containing monomer, 2-acryloyloxyethyl diethyl
phosphate (ADEP), was synthesized from 2-hydroxyethyl acrylate
and diethyl chlorophosphate. Details of the experiments and
identification of the product formed are described elsewhere [20].
Plain weave bleached cotton fabric (285 g/m2) purchased from
a local vender was washed several times in a washing machine at
95  C until it was free from any remaining surfactant prior to use.
2.2. Determination of the adsorption isotherm
Adsorption of DTAB and HTAB on cotton fabric was carried out
by placing a 1.2-g piece of cotton fabric in a vial containing 30 mL
surfactant solution of known initial concentration. The adsorption
took place at 30  C over 15 h in a 36 mL vial with the lid sealed with
paraffin film. All vials were placed in a shaker bath. Surfactant
concentration in the supernatant was determined by using a total
organic carbon analyzer (TOC) (Shimadzu, TOC 5000) with the
amount of adsorbed surfactant calculated by a simple mass balance.
The initial surfactant concentration in this experiment was varied
from 0.7 to 40 mM for DTAB and from 0.1 to 8 mM for HTAB which
covered the regions below and above the critical micelle concen-
tration (CMC). A plot of the amount of adsorbed surfactant versus
equilibrium supernatant concentration yielded the surfactant
adsorption isotherm.
surfactants and with a 1:5 initiator:monomer molar ratio. Surfactant
concentrations used were 14.0 mM and 0.9 mM for DTAB and HTAB,
respectively. Cotton fabric (6.5 cm  6.5 cm, 1.2 g) was placed in
a vertical position with no folding or overlapping in a 36-mL vial
containing a 30 mL solution of surfactant, monomer (using ethanol
as a co-solvent) and initiator at the desired concentrations. The vial
was then wrapped with aluminium foil and the lid was screwed on
and sealed with paraffin film. All vials were placed into a shaker bath
set at 30  C for 15 h to allow the surfactant adsorption and monomer
adsolubilization in the admicelle to reach equilibrium. The
temperature was then raised to 75  C to initiate the polymerization
reaction which was carried out for 24 h. After polymerization, the
treated fabric was removed from the vial and washed in water three
times at 80  C for 30 min to remove the upper-layer surfactant.
Finally, the fabrics were dried in an oven overnight at 65  C.
2.4. Characterization of coated film on treated cotton
The polymer film coated on treated cotton was analyzed on an
FTIR-ATR spectrometer (Nicolet model Nexus 670). The spectra
were collected at a resolution of 4 cm1 over the wavenumber
range of 4000–400 cm1.
2.5. Thermal analyses
Thermal analyses of untreated and PADEP-coated cotton was
carried out using a Perkin Elmer TG–DTA analyzer, Model TGA
2550, operating under N2 atmosphere using a platinum pan con-
taining 25–30 mg of cotton. The runs were performed over
a temperature range of 30–600  C at a heating rate of 10  C/min
under a continuous N2 flow of 100 mL/min.

2.3. Admicellar polymerization process

Polymerization of ADEP to form poly(2-acryloyloxyethyl diethyl

phosphate) (PADEP) on cotton fabric was carried out in a series of
ADEP concentrations (6.2, 18.6, 24.8 and 31 mM) for each of the two

Step 1. Step 2. Step 3. Step 4.

Admicelle Monomer Admicellar Washing
Formation Adsolubilization Polymerization

M = monomer, P = polymer, I = initiator

Fig. 1. Schematic of the admicellar polymerization process. Fig. 2. Adsorption isotherms of (a) DTAB and (b) HTAB on cotton at 30  C.
560 A. Siriviriyanun et al. / Polymer Degradation and Stability 94 (2009) 558–565
Fig. 3. Correlation between phosphorus content and ADEP concentration.
2.6. Determination of the phosphorus content on PADEP-coated
cotton
Treated fabric samples taken from different parts of the test
fabric were cut into small pieces. Concentrated H2SO4 (2 mL) was
added to 0.1 g of the sample in a bottle. Then 10 mL of 30% H2O2 was
added dropwise to the mixture which was stirred by a magnetic
stirrer on a hot plate, allowing the reaction to subside between
drops. The mixture was then stirred and heated on the hot plate for
1 h. After that, the completely digested sample as a clear viscous
solution was transferred to a 50 mL volumetric flask, and then
carefully diluted to 50 mL with distilled water. The sample thus
prepared was analyzed with a Perkin Elmer Model PLASMA-1000
inductively coupled plasma/atomic emission spectrometer (ICP/
AES) to determine the percent concentration of phosphorus [21].
Control samples with known amounts of phosphorus added were
used to confirm the accuracy of the results.
2.7. Burning tests
Burning behavior of untreated and PADEP-coated cotton fabrics
were studied using the Atlas 45 Automatic Flammability Tester
according to ASTM D1230-94 [22]. In this study, the ignition time
Fig. 4. FTIR-ATR spectra of (a) PADEP, (b) untreated cotton, PADEP-coated cotton using
(c) DTAB and (d) HTAB.
was set at 10 s. The experiments were carried out at the ambient
temperature of 30  C and 68% RH. The burning behavior of the
fabric was recorded by a digital video camera.
2.8. Characterization of the charred fabric surface
The charred surface of the burnt fabric from the burning tests
was investigated by SEM using a Jeol SEM model JSM 5200-2AE.
Charred samples did not need gold sputter coating since carbon on
the surface already provided sufficient electrical conductivity.
3. Results and discussion
3.1. Adsorption isotherms of DTAB and HTAB on cotton fabric
In admicellar polymerization the surfactant concentration used
should be just below the critical micelle concentration (CMC) of the
surfactant solution to ensure maximum surfactant adsorption while
avoiding emulsion polymerization. The CMC of a surfactant solution
can usually be determined by its adsorption isotherm and the point
where the adsorption starts to reach a constant value is taken as the
CMC of the system. The adsorption isotherms of DTAB and HTAB on
cotton at 30  C are shown in Fig. 2. The estimated values of the CMC
for DTAB and HTAB from the adsorption isotherms were 14.0 and
0.9 mM, and the adsorbed amounts at the CMC were 16.5 and
17.1 mmol/g cotton, respectively. The results compare favorably with
CMC’s from the literature of 16 and 0.92 mM, respectively [23].
Hence, the concentrations of 14.0 mM DTAB and 0.9 mM HTAB were
chosen for the admicellar polymerization, respectively.
3.2. Correlation between ADEP concentration and the phosphorus
content
In this work the amount of polymer coated on the treated fabric
was determined by its phosphorus content. The results in Fig. 3
show that phosphorus levels in the treated fabric increased with
the initial monomer concentration. The phosphorus content of the
PADEP-coated cotton using HTAB as a surfactant was higher than
using DTAB. It is known that in general solubilization goes up with
the diameter of the micelle and, similarly, adsolubilization
increases with the thickness of the admicelle. HTAB has a longer
hydrocarbon chain length than DTAB, and the hydrophobic core of
the HTAB admicelle can be expected to be larger. Hence, more ADEP
monomer can partition into the core of the HTAB admicelle leading
to greater polymer formation on the fiber surface. The phosphorus
content of fabric using DTAB ranged from 0.23 to 0.88 mg/g cotton
while that using HTAB ranged from 0.36 to 2.98 mg/g cotton.
3.3. Identification of PADEP film on the treated cotton
FTIR-ATR spectra of PADEP, untreated and PADEP-coated cotton
fabrics are shown in Fig. 4. The characteristic peak of PADEP at
1730 cm1, attributed to the carbonyl (C]O) bond of ADEP, can be
seen in the spectra of PADEP alone and of the treated fabrics indi-
cating that PADEP is present on the cotton surface. The film thick-
ness calculated from the amount of polymer formed on the fabric
and the fabric surface area of 4.54 m2/g as determined from BET
with nitrogen was found to be in the range of 1–5 nm indicating
that the film formed was ultrathin. Other workers also found the
film formed by the admicellar polymerization process to be very
thin in nanoscale [16,24].
 Fig. 6. TGA, DTG, DTA and DDTA curves of (a) untreated cotton and the PADEP-coated
Fig. 5. TGA, DTG, DTA and DDTA curves of (a) untreated cotton and the PADEP-coated cotton using (b) 6.2 mM, (c) 18.6 mM and (d) 24.8 mM and (e) 31 mM ADEP using
cotton using (b) 6.2 mM, (c) 18.6 mM and (d) 24.8 mM and (e) 31 mM ADEP using DTAB. HTAB.
562 A. Siriviriyanun et al. / Polymer Degradation and Stability 94 (2009) 558–565

Fig. 7. Correlation between (a) DTG peak temperature, (b) % remaining residue, and
phosphorus content.
Fig. 9. Correlation between endothermic peak temperature and DTG peak
temperature.

3.4. Thermal analyses

temperature obtained with 2.98% phosphorus content was 304  C
3.4.1. The TGA/DTG thermograms with 23.9% remaining residue. This is a significant change from the
The thermal behavior of untreated and PADEP-coated cotton untreated cotton which has a degradation temperature of 350  C
was investigated by using a TG–DTA analyzer. Figs. 5 and 6 show with 10% remaining residue.
the TGA, DTG, DTA, and DDTA thermograms of untreated and A plot of decomposition temperature versus the % remaining
treated cotton for DTAB and HTAB at different ADEP concentrations. residue exhibits a strong linear correlation (Fig. 8). This suggests
From the TGA and DTG curves, it can be seen that the main that the flame retardant mechanism of phosphorus-based flame
degradation temperature of untreated cotton started at 310  C
followed by a sharp weight loss of almost 80% over a narrow
temperature range of 60  C with a remaining residue of 10% at
600  C. Its DTG curve showed a single peak at 350  C. In the case of
PADEP-coated cotton, with increase in ADEP concentration, the
DTG peak decreased both in the peak temperature and peak height
while the TGA curves showed a corresponding increase in the %
remaining residue.
Fig. 7 shows the effect of phosphorus content on the DTG peak
temperature and % remaining residue. The graphs are parabolic in
shape with a rapid change initially and the slope leveling off after
a phosphorus content of about 1.5 mg/g cotton. The result confirms
the general observation that up to a certain limit, further increase in
the phosphorus content will lead to no further change in the flame
retardancy of cotton [5]. The lowest cotton degradation

Fig. 10. DDTA thermograms of untreated cotton and PADEP-coated cotton using DTAB
Fig. 8. Correlation between DTG peak temperature and % remaining residue. and HTAB at (b) 6.2 mM, (c) 18.6 mM, and (d) 24.8 mM, and (e) 31 mM ADEP.
 A. Siriviriyanun et al. / Polymer Degradation and Stability 94 (2009) 558–565 563

Fig. 11. Burning behavior of (a) untreated cotton and PADEP-coated cotton using (b) DTAB, (c) HTAB at various times, and (d) samples at the end of the burning.

retarding agent proceeds through dehydration leading to the
formation of carbonaceous char. It is interesting to note that the
points from the use of both DTAB and HTAB fit very well on the
same graph indicating that degradation of the treated fabrics
depended only on its phosphorus content and not on the type of
surfactant used. From the graph, it was found that a 10 decrease in
the DTG peak temperature led to an approximately 2.7% increase in
the % remaining residue.
3.4.2. The DTA thermograms
All the DTA thermograms of untreated and treated cotton
show two sharp endothermic peaks, one at 100  C which repre-
sents the loss of absorbed water, and the other one at around
300–350  C which represents the endothermic decomposition of
the cotton fiber (Figs. 5 and 6). The endothermic peak tempera-
ture shifted to lower temperature with an increase in the amount
of ADEP used. Fig. 9 shows that there is a good linear relationship
between the endothermic peak temperature and the DTG peak
temperature with the endothermic peak about 12  C higher than
the DTG peak. This is understandable as the sample needs to
undergo substantial weight loss before the endothermic peak can
be detected.
3.4.3. The DDTA thermograms
A DDTA thermogram is obtained by taking the first derivative of
the DTA thermogram. Hence, even a very slight temperature
change can be detected. Fig. 10 shows the DDTA thermograms of
the samples over the temperature range of 250–400  C. It can be
seen that, when a high amount of ADEP was used, an additional
second peak can be seen at a lower temperature. This peak became
more prominent and shifted to a lower temperature as the phos-
phorus content increased. It is proposed that this small second peak
may result from the phosphorylation of cellulose prior to its
thermal degradation.
564 A. Siriviriyanun et al. / Polymer Degradation and Stability 94 (2009) 558–565
Fig. 12. SEM micrographs of (a) fabric surface of untreated cotton, and burnt surface of PADEP-coated cotton using (b) DTAB and (c) HTAB.
3.5. Burning behavior of the PADEP-coated cotton fabric
Differences in the burning behavior of the untreated and PADEP-
coated cotton using DTAB and HTAB at the monomer concentration
of 31 mM can be seen in sequences of the ASTM flammability test
(Fig. 11a–c). In the case of untreated cotton, after removing the
ignition source, the fabric burned slowly at first, but, as more
flammable volatiles evolved and started to burn, an upward-
moving flame formed and the burning process became more rapid
and intense. At 20 s, the flame was distinctly evident. Ten seconds
later, the flame had significantly gained in height and speed while
burning the lower half of the fabric in less than 40 s and the whole
fabric in 71 s with nothing remaining. In contrast, for the PADEP-
coated cotton using DTAB as the surfactant (Fig. 11b), the flame
spread slowly after removing the ignition source with little change
in flame height and intensity until it reached the top end of the
fabric sample. The flame extinguished in a total of 2.05 min leaving
behind a charred fabric. During thermal degradation of PADEP-
coated cotton, PADEP on the cotton surface would degrade first
generating phosphoric acid, leading to phosphorylation at C-6 of
the anhydroglucose unit and blocking the formation of levogluco-
san. Decrease in levoglucosan formation lowered the fuel available
for flame propagation [7] and, hence, the flame generated from the
burning of PADEP-coated cotton was much less intense. In the case
of treated cotton using HTAB (Fig. 11c), the flame immediately
extinguished upon removing the ignition source, leaving behind
a small charred area. The results were consistent with the higher
amount of phosphorus deposited on the fabric prepared with HTAB.
After the burning tests, the three samples displayed marked variety
in appearance as clear evidence of the difference in flammability
(Fig. 11d). It is interesting to note also that the charred surface of the
DTAB sample was very uniform indicating that the polymer film
fully and uniformly covered the fabric surface.
3.6. Charred surface of PADEP-coated fabric
SEM images of the charred surface of PADEP-coated cotton
fabrics after the burning tests and of the surface of virgin untreated
fabric are presented in Fig. 12. It can be seen that fibers in both
burned samples still retained the integrity of the fiber structure, but
with a reduced diameter when compared with the virgin fibers. The
diameter of the burned cellulose fibers of the PADEP-coated with
HTAB (Fig. 12c) was larger than those in the treated fabric using
DTAB (Fig. 12b), indicating that the higher the content of phos-
phorus on the cotton surface, the larger the size of the burned
cellulose fiber. This can be explained by the increased amount of
char formed from the acid-catalyzed dehydration. The char acts as
a thermal barrier resulting in a reduction in the heat transfer to the
interior of cotton during the burning process and so, less
degradation.
4. Conclusions
The amount of phosphorus in flame retardant cotton has the
effect of reducing the decomposition temperature of the treated
cotton with an increase in the amount of char formation during
thermal degradation. PADEP-coated cotton using HTAB as surfac-
tant has higher phosphorus content than using DTAB. Hence,
PADEP-coated cotton using HTAB has lower decomposition
temperature and higher amount of char formation than using
DTAB. Importantly, the amount of phosphorus also affects the
burning behavior of the flame retardant cotton. In case of PADEP-
coated cotton using DTAB, the flame spread slowly charring the
whole test sample while the burning of the PADEP-coated cotton
using HTAB stops after removing the ignition source, leaving
behind only a small charred area on the fabric surface.
Acknowledgements
Ampornphan Siriviriyanun gratefully acknowledges the schol-
arship provided by the Thailand Research Fund (TRF-RGJ Program)
and The Petroleum and Petrochemical College. Additional support
from National Excellence Center in Petroleum, Petrochemical, and
Advanced Materials is also gratefully acknowledged. Special thanks
also go to Asst. Prof. Sireerat Charuchinda and Mr. Rutchapong
Horthimaworrakorn at the Department of Materials Science,
Faculty of Science, Chulalongkorn University, for their assistance in
the flammabilty tests.
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