Photostability and Durability Properties of Photochromic

Organosilica Coating on Fabric

Marzieh Parhizkar, PhD, Yan Zhao, PhD, Xunagi Wang, PhD, Tong Lin, PhD

Deakin University, Geelong, Victoria AUSTRALIA

Correspondence to:
Tong Lin email: [email protected]

ABSTRACT
Photochromic fabrics were prepared by a dip- the great advantages of this technique. Organically
coating method using a silica sol-gel solution modified silica (organosilica) can be processed
containing photochromic dyes. The coated fabric through the sol-gel method to develop
showed a rapid photochromic response. Three microporous matrices, which are excellent hosts
methods; incorporating a UV stabilizer in the for organic dopants. The inclusion of organic
coating layer, hydrophobic treatment of the porous functional groups in hybrid silica helps exploit the
surface, and covering the coating layer with an superior thermal and mechanical properties of the
additional silica layer; were used to improve the inorganic constituents, as well as create a
photostability and durability. All three treatments favorable environment for photochromic dye [16].
improved the photostability without noticeably
changing the photochromic response/fading Previously, we reported on developing a hybrid
speeds. Most of the treatments reduced the organosilica coating with a photochromic dye
washing and abrasion durability. The extra coating embedded through a sol-gel method [17].
layer increased the fabric rigidity. Although UV irradiation is essential in producing
the photochromic effect, prolonged exposure to
INTRODUCTION UV light leads to degradation of photochromic
Photochromism is a photo-induced transformation dyes, resulting in low photostability. To solve this
between two optical absorption states [1-4]. Since problem, three strategies were developed. These
the first report in 1867, this fascinating color- include incorporating UV photo-stabilizers,
changing property has received great attention in modifying surface wettability with a low surface
science and industry [1]. It has been used in areas energy silane, and blockading the dye-
such as sunglasses and ophthalmic lenses, security encapsulating pores with an additional silica
printing, cosmetics, optical data storage, coating layer. The effect of the treatments on
memories, optical switches, sensors, and displays photochromic properties, photostability, durability
[5-10]. Recently, there has been some interest in against washing and abrasion, fabric rigidity, and
developing photochromic smart textiles [8, 9, 11- wettability of the coatings were examined.
14]. Conventional methods to apply photochromic
substance on fabrics include exhaustion dyeing EXPERIMENTAL
and coating the dye microcapsules onto fabric Materials
surface. However, the first method fails to provide A list of chemicals used in this work is given in
sufficient space for photochromic molecules to Table I. An undyed double jersey knitted interlock
accomplish the structural transformation, and fabric (245 grams per square meter) was used in
consequently the photochromic effect is this work 1 . The fabric consisted of 19.5 μm
insignificant. The second method often leads to a Australian merino wool top, chlorine/Hercosett
harsh fabric handle. treated to machine washable standards. A visual
assessment of the front and back side of the fabric
The sol-gel method has been recently used for indicated 12 and 10 stitches per cm in the wale
producing photochromic hybrid materials [15]. and course directions, respectively.
The possibility of producing transparent, porous
solids at a low processing temperature is one of

1
Obtained from AIM Sports Pty Ltd (Australia)

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Volume 9, Issue 3 – 2014
 TABLE I. List of chemicals.

Type Chemical name Abbreviation

5-chloro-1,3-dyhydro-1,3,3-trimethylspiro[2H-
Photochromic dye -
indole-2,3’- [3H]–naphth [2,1-b] [1,4] oxazine]
Silica precursor octyltriethoxysilane OTES
Silica precursor phenyltriethoxysilane PhTES
Silica precursor 3-Aminopropyl) triethoxysilane APS
Silica precursor (3-Trimethoxysilyl) propylmethacrylate MPS
Silica precursor Tridecafluorooctyl triethoxysilane FAS (fluoroalkylsilane)2
Catalyst tetracetoxysilane TAS
2,2'-thiobis(4-tert-octylphenolato)-Nbutylamine
UV quencher UVQ3
nickel (II)
UV absorber 2-hydroxy-4-methoxy-benzophenone HMBP
2 -(2Hbenzotriazol-2-yl)-4-(1,1,3,3-
UV absorber BTMBP 4
tetramethylbutyl) phenol
poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidine HALS 5 Hindered Amine Light
Free radical scavenger
ethanol-alt-1,4-butanedioic acid) Stabilizer)
2
FAS was donated by Evonik Degussa. All the other chemicals were obtained from Sigma-Aldrich and used as received.
3
Commercial name: UV-1084
4
Commercial name: Tinuvin-329
5
Commercial name: HALS-622

Silica Sol-Gel Synthesis and Coating

Silica sols were prepared by mixing TAS, To add UV stabilizer to sols, a stabilizer was
alkyltriethoxysilane (RSi), and ethanol, and dissolved in ethanol. After ultrasonication for 5
stirring until TAS crystals were dissolved. Water minutes, dye-containing sol was added, and stirred
was subsequently added using a syringe pump at a at about 70 °C to produce clear solutions. The
1 ml/h rate and the mixture was stirred for 24 h. molar ratio of photochromic dye: UV stabilizer
The molar ratio of TAS: RSi: H 2O: ethanol was was 1:1. To adjust the wettability of the coating,
1:32:100:320. TAS was selected as catalyst to FAS was added to the silane at the beginning of
slowly release acetic acid into the mixture, to synthesis (before adding water). To seal off the
avoid rapid hydrolysis. Alkyltriethoxysilanes dye-containing pores, a second layer (20 mL) of
OTES and PhTES, with a ratio of 1:2 (mol/mol) sol containing no dyes was applied after air drying
were used for making all the coating solutions. the first for 24 hours, and was heat treated 24
The chemical structures of OTES and PhTES are hours later.
shown in Figure 1. 10 mL of photochromic dye-
ethanol solution (Dye: RSi molar ratio of 1:100) Photochromic Measurements
was then mixed with 10 mL of synthesized sol- A SUB4000 optical fiber UV-VIS spectrometer
gel, and stirred at about 70 °C until a clear and a DH2000-BAL UV-light source with a
solution was obtained. A 20×20 cm2 piece of wool wavelength range of 230-2000 nm 2 , and a
fabric was laid flat in the solution, air-dried personal computer were employed to measure the
horizontally to reduce coating nonuniformity, and photochromic properties of the coatings. The color
cured at 110 °C for 10 min. The coated fabric was changes are expressed using the differential
left for 1-2 days before measurement to ensure absorption between the state of presence and
complete stabilizing of the silica matrix while absence of UV light, ∆A=Alight−Adark , at the
avoiding wool yellowing caused by excessive heat wavelength of maximum absorption (~627 nm).
treatment.
The photochromic response and fading were
recorded in real time as the ascent and descent of
absorption when UV light was turned on and off,
respectively. The response and fading rates were
calculated from the time required for absorption to
rise and subsequently fall to half of its maxima.
These were expressed as response and fading half-
life times, t1/2 and t′1/2, respectively, and were

FIGURE 1. Chemical structures of (a) OTES, and (b) PhTES. 2

Both from Ocean Optics

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Volume 9, Issue 3 – 2014
measured using the absorption versus time graph where g2 is the thickness of the coated fabric (cm),
obtained from the software 3. measured under a 1 N weight. Water contact angle
was measured on a KSV Model CAM101 Contact
To measure photostability, samples were Angle Meter.
illuminated by strong UV light from an Hg metal
halide lamp 4 and their photochromic absorption RESULTS AND DISCUSSION
was recorded after each exposure period The chemical structure and photochromic
(approximately 3.2 hours). The required time for transformation of Photorome II, the spiro-oxazine
the coated fabric to lose its entire photochromic (SPO) chromophore used in this study, are shown
effect (i.e. for absorption to no longer rise with in Figure 2. This type of chromophore is colorless
UV stimulation) was considered the lifetime of the in its closed form, and undergoes a ring opening
photochromic coating. For comparison, the reaction when subject to UV radiation,
photostability of a selection of coatings was also transforming into a colored merocyanine in its
measured in a Suntest XLS+ from ATLAS. The open form. It subsequently returns back to its
samples were exposed to simulated sunlight for 5 stable colorless state thermally or via visible light.
hour periods at a 300 W/m2 energy level.

Durability and Rigidity Measurements

The durability of the coatings was calculated from
Eq. (1):

Durability (%) = ∆A2/∆A1 × 100 (1)

FIGURE 2. Structure and photochromic reaction of
spirooxazine; left: closed colorless form; right: open colored
where ∆A1 and ∆A2 represent the differential form.
maximum absorption of the coating before and
after the durability test, respectively. The To select a suitable silica precursor for the
Martindale machine was used for the durability to synthesis of the matrix, preliminary trials were
abrasion measurement. A 9 kPa load was applied carried out with different combinations of OTES
and changes in absorption were recorded after and PhTES silanes. A ratio of OTES:PhTES 1:2
1000 abrasion cycles. The wash fastness (O:P 1:2) was selected for optimum coating
measurement was carried out in accordance with performance, encompassing the superior
Australian standard AS 2001.4.15.C. A M003B photostability and response/fading speed of OTES
Shirley Stiffness Tester was employed for in addition to the better durability of PhTES
measuring the bending properties of the coated against abrasion and washing. The chemical
fabrics. The test was conducted in accordance structures of the silica precursors are shown in
with BS 3356 BS9073 part 7 and ASTM D1388. Figure 1. The Octyl functional group in OTES
The Flexural Rigidity (G) and Bending Modulus helps create more flexible pores, which leads to
(Q) were calculated from Eq. (2) and Eq. (3) in less steric hindrance for the encapsulated dye.
mg∙cm and kg/cm2, respectively: This allows better optical performance by the
photochromic dye. On the other hand, the phenyl
G = 0.1MC3 (2) ring in PhTES creates rigid pores which inhibit
the structural transformation of the photochromic
where M is the mass per unit area (g/m2) and C is dye, leading to reduced photochromic
the bending length (cm) of the fabric. performance.

Q = (12G × 10-6)/g23 (3) The optical absorption of an OTES: PhTES 1:2

organosilica coating doped with SPO
photochromic dye in the presence and absence of
UV irradiation is displayed in Figure 3a. In the
absence of UV light, the absorption spectrum was
a flat line, whereas a photochromic peak was
observed at a wavelength of around 627 nm in the
3
presence of UV light.
SpectraSuite
4
Type OH N30/50E from Heraeus Noblelight GmbH; UV-A:
350-400 nm, relative irradiance around 90-120, and an
intensity of approximately 80 mW/cm2 at 365 nm

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Volume 9, Issue 3 – 2014
The optical absorption spectrum of the coating radicals [18]. UV absorbers, HMBP and BTMBP,
recorded in real time at 627 nm is shown in Figure block UV light, reducing the chance of generating
3b. The time required for the absorption to ascend free radicals [19, 20]. Hindered amine light
and subsequently descend to half of its maxima stabilizers (e.g. HALS) are free radical scavengers
was calculated as shown in this graph, and [21]. Although they do not absorb UV light, they
denoted as t1/2 and t′1/2, or response and fading trap and deactivate the free radicals generated,
half-life times, respectively. preventing photochromic dyes from being
degraded.
TABLE II. Coating conditions.

Method Additives Constituents

Control OTES:PhTES 1:2 sol + dye

Adding UV UVQ O:P 1:2 sol + UVQ + dye
stabilizer HALS O:P 1:2 sol + HALS + dye
BTMBP O:P 1:2 sol + BTMBP + dye
HMBP O:P 1:2 sol + HMBP + dye
Fluorinating FAS O:P 1:2 + FAS sol + dye
Double coating APS 1 st O:P 1:2 sol + dye
with extra silica layer
2 nd APS sol only
layer

MPS 1 st O:P 1:2 sol + dye

layer
2 nd MPS sol only
layer

Same silica 1 st O:P 1:2 sol + dye

(shown as layer
2xSS) 2 nd O:P 1:2 sol only
layer

FIGURE 3. (a) VIS spectra, and (b) coloration-decoloration

curve of an OTES:PhTES 1:2 photochromic coating.
FAS enriches the pore surfaces with fluorine
The effects of three different treatments on atoms leading to increased hydrophobicity, thus
photochromic and durability properties of the preventing moisture and degrading elements from
photochromic fabric were measured. The coming into contact with the dye. Hou, et al.
treatments included incorporating UV photo- reported the positive effect of fluoro-alkyl silane
stabilizers, modifying the coating’s on photostability, used independently or in
hydrophobicity by means of fluorinating the conjunction with other additives [22-24]. In this
pores, and blockading the pores with an additional work, FAS was combined with the sol precursors
layer of silica coating. prior to hydrolysis, to further engage this additive
with the matrix.
In this study, three different types of light
stabilizers were employed: a free radical The addition of an extra layer of sol-gel silica was
quencher, UVQ, two UV absorbers, namely adopted to seal the dye-containing pores, and thus
HMBP and BTMBP, and a free radical scavenger, deterring degrading elements. (3-Aminopropyl)
HALS. The quencher, UVQ, captures the energy triethoxysilane (APS) and (3-Trimethoxysilyl)
absorbed by the photochromic dye as a result of propyl methacrylate (MPS) were used as
the UV irradiation, and dissipates it as heat, precursors for the additional protective sol-gel
fluorescence, or phosphorescence emission. It has layer. The amino group also helps protect the
been reported that the degradation of chromophore from photobleaching [25].
photochromic dye is caused by photo-induced free

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Volume 9, Issue 3 – 2014
The chemical structures of the UV stabilizers, Figure 5b shows the coloration and fading half-
fluorinated alkyl silane (FAS), and amino and life times for the untreated (control) and treated
methacrylate functionalized silica precursors are samples. It was observed that the incorporation of
illustrated in Figure 4. UV stabilizers, FAS coating, and extra protective
coating increased the response and fading times,
while extra coating layer from APS sol-gel
improved both these rates and MPS enhanced
fading rates only. However, the impact of the
treatments on coloration and de-coloration rates
was overall insignificant.

FIGURE 4. The chemical structures of UV stabilizers: (a)

UVQ, (b) HALS, (c) BTMBP, (d) HMBP, as well as (e) FAS,
(f) APS, and (g) MPS.

Photochromic Properties
The lifetime of the photochromic effect was
measured by exposing the coated fabric to strong
UV light for periods of 3.2 hours. The optical
absorption was measured at the beginning of the
experiment and after each exposure period. The
test was continued until a photochromic peak was
no longer distinguishable in the absorption
spectrum. The response and fading times were FIGURE 5. (a) Photostability and (b) photochromic response
calculated from the strips in Figure 3b. The and fading half-life times of the coatings.
photostability and response/fading data are plotted
in Figure 5. All three types of treatments The UV absorbers and extra APS silica coating
improved photostability, without significantly reduced the maximum absorption while HALS
affecting coloration/decoloration times. The exhibited a smaller impact and UVQ displayed
incorporation of UVQ was the most efficient none (Figure 6). Since UV absorbers also
treatment in terms of increasing photostability. Its absorbed UV light, the addition of the UV
performance was followed by that of double- absorbers lowered the photochromic optical
coating with APS sol-gel. The enrichment of the absorption.
pores with fluorine however was the least
effective treatment, although it also slightly
increased photostability.

It is difficult to judge the performance of the UV

absorbers in comparison with the free radical
scavenger, as BTMBP performed better than
HALS in terms of improving photostability, while
HMBP performed poorer.

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Volume 9, Issue 3 – 2014
 Figure 7b shows the UV absorption change for the
UVQ and APS coatings during irradiation with
Suntest. The slope of the fall was 0.003 for UVQ
and 0.009 for APS in the first exposure period (5
hours). This was followed by a 0.006 and 0.005
decline for UVQ and APS, respectively, in the
second cycle of irradiation. The rate of
photochromic loss in the Suntest, which simulated
solar radiation, was an order of magnitude slower,
and the total photochromic lifetime longer
compared to the UV light box, which used a Hg
metal halide lamp as the light source. This is due
to the lower intensity of UV irradiation in the
FIGURE 6. The differential absorption at a wavelength of
Suntest compared to that in the Hg metal halide
627 nm.
lamp. It is noteworthy that the Suntest provides a
The changes of UV absorption with time for the closer simulation of the real-life application of
two most photostable coatings, measured in a UV photochromic fabrics. However, the UV light box
light box, are shown in Figure 7a. Absorption was selected as the main apparatus for
dropped with a rate of 0.01 and 0.03 for UVQ and photostability testing in this work because its
APS, respectively, in the first cycle (3.2 hours). higher UV intensity helped expedite the
This was followed by a 0.04 and 0.01 drop in the measurements.
following cycle for UVQ and APS, respectively.
Generally, photo-degradation was most rapid in The higher photostability which resulted from the
the first few cycles of irradiation, but slowed incorporation of UVQ compared to that of APS
down after approximately ten hours of UV can be attributed to the mechanism by which UVQ
exposure. This can be attributed to a screening works and the method by which APS was applied
effect in which the photochromic dyes in the to the fabric. As mentioned earlier, UVQ converts
uppermost layers of the coating are the first to light into thermal energy or other forms of
become degraded from UV irradiation, and their emission. The amino group in APS protects the
degraded products screen the inner layers of dye dye from decomposition in the presence of light
from UV exposure. and oxygen. However, APS was applied to the
fabric as an additional layer of silica.

The photostability of the control, UVQ, APS, and

FAS samples, measured using the Suntest, were
45±0, 328.3±2.9, 113.3±5.8, and 36.7±2.9 hours,
respectively.

Washing and Abrasion Durability

The durability of the coated fabrics against
abrasion was assessed by monitoring the changes
in absorption after 1000 abrasion cycles (Figure
8a). Although some of the coatings reduced the
abrasion durability, the overall level of abrasion
fastness was satisfactory. The incorporation of UV
absorbers BTMBP and HMBP merely reduced the
durability by approximately 2%, while MPS and
FAS caused a 9% and 11% fall, respectively. The
double coating with same silica and APS
treatments shifted durability by 11% and 13%,
respectively. None of the treatments seemed to
lead to a significantly large change in abrasion
durability.
FIGURE 7. Change of photochromic absorption with UV
irradiation time, irradiated by (a) Hg metal halide lamp, and
(b) Suntest.

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Volume 9, Issue 3 – 2014
 FIGURE 9. (a) Flexural rigidity and (b) bending modulus.

Wettability
The water contact angle of the coated fabrics was
FIGURE 8. Durability to (a) abrasion and (b) washing.
also measured. All the treatments caused a slight
increase in the surface hydrophobicity, as
The washing durability was measured by
evidenced by the slightly increased contact angle
recording the changes in absorption after a wash
after the coating treatment. The largest increase in
cycle (Figure 8b). The incorporation of UVQ and
contact angle was caused by HALS (4.5%),
BTMBP were found to improve the washing
followed by BTMBP (3.9%) and UVQ (3.9%).
durability, while the other treatments showed
Double coating with the same silica caused the
reduced durability compared to the control. The
smallest change (0.3%), followed by double
wash durability of the MPS double coating was
coating with APS (0.9%) and HMBP (1.1%). The
the lowest among all treatments.
more hydrophilic nature of the APS and HMBP
coatings compared to the other treatments could
Fabric Flexural Rigidity
be attributed to the amino group and hydroxyl
The handle of the coated fabrics was assessed
group present in their chemical structures,
based on their flexural rigidity (mg∙cm) and
respectively.
bending modulus (kg/cm2). The results indicated a
notable increase in stiffness caused by APS sol-
gel treatment (Figure 9). The other treatments did
not cause a significant increase in flexural rigidity
and bending modulus. All the treatments showed a
higher flexural rigidity and bending modulus in
the warp direction in comparison with the control,
while this trend was not observed for all coatings
in the weft direction.

FIGURE 10. Water contact angle of the coated fabrics.

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Volume 9, Issue 3 – 2014
CONCLUSION [10] Chodorowski, S., Quinn, F. X., and Sanchez,
A photochromic silica coating on fabric was C., "Method for improving UV radiation
produced. The effects of incorporating UV stability of photosensitive sunscreen
stabilizers, modifying the surface wettability, and filters". 2003, L'Oreal.
adding an extra silica layer on the coating [11] Lee, S. J., Son, Y. A., Suh, H. J., Lee, D. N.,
properties were examined. All the treatments and Kim, S. H., "Preliminary exhaustion
improved photostability to different extents, but studies of spiroxazine dyes on polyamide
did not affect the other photochromic properties fibers and their photochromic properties",
significantly. The highest photostability was Dyes and Pigments, 69, 1-2. 2006, 18-21.
obtained by incorporation of a quencher UV [12] Son, Y. A., Park, Y. M., Park, S. Y., Shin, C.
stabilizer. The addition of an extra layer of APS J., and Kim, S. H., "Exhaustion studies of
sol-gel was the next most effective treatment in spiroxazine dye having reactive anchor on
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maximum absorption and increased coating properties", Dyes and Pigments, 73, 1.
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AUTHORS’ ADDRESSES
Marzieh Parhizkar, PhD
Yan Zhao, PhD
Xunagi Wang, PhD
Tong Lin, PhD
Deakin University
Pigdons Rd
Geelong, Victoria 3216
AUSTRALIA

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Volume 9, Issue 3 – 2014