POLYMERS FOR ADVANCED TECHNOLOGIES

Polym. Adv. Technol. 14, 676–685 (2003)

Published online in Wiley InterScience (www.interscience.wiley.com). DOI:10.1002/pat.435

Enzyme Degradability of Benzylated

Sisal and its Self-reinforced Composites
Xun Lu1,2, Ming Qiu Zhang3*, Min Zhi Rong1,3 and Gui Cheng Yang1,3
1
Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Zhongshan University,
Guangzhou 510275, P. R. China
2
Department of Polymer, School of Materials Science and Engineering, South China University of Technology,
Guangzhou 510640, P. R. China
3
Materials Science Institute, Zhongshan University, Guangzhou 510275, P. R. China

ABSTRACT
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INTRODUCTION
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To produce natural polymer based composite materials, It has been known that wood can be converted into
sisal fibers were slightly benzylated and then molded into thermoplastics by etherification or esterification
sheets. Because the modified skin portions of the fibers such as cyanoethylation, benzylation and carbox-
acquired certain thermoplasticity and the unmodified core ylation, which were traditionally used for the mod-
parts remain constant, the resultant composites fall into ification of cellulose [1–3]. Having been treated in
the category of self-reinforced ones. The present article is this way, wood sawdust becomes thermally form-
devoted to the evaluation of the materials biodegradability able at certain temperatures and pressure without
with the help of cellulase. It was found that the inherent the aid of additional adhesives. It factually taps
biodegradability of plant fibers is still associated with the another resource for producing thermoplastic com-
benzylated sisal and the molded composites, as character- ponents based on renewable biomaterials. Viewed
ized by structural variation, weight loss and deterioration from a practical angle, however, the mechanical
of mechanical performance of the materials. Reaction properties of the plates molded from the plasticized
temperature and time, pH value of the enzyme solution, wood flour are not satisfactory enough due to their
and dosage of the enzyme had significant influences on the relatively low strength (flexural strength: 34.3 MPa)
decomposition behavior of the materials. In principle, the and the intrinsic brittleness (unnotched Charpy
enzymolysis of sisal and its self-reinforced composites is a impact strength: 5.6 kJ/m2) [4]. To overcome the
diffusion-controlled process. Due to the insusceptibility of aforesaid shortcoming, a novel type of thermoplas-
lignin to cellulase and the hindrance of it to the cellulase ticized and self-reinforced composite made solely
solution, the degradation rates of the materials are gra- from sisal has been developed in our laboratory
dually slowed down with an increase in time. Copyright [5, 6], which takes advantage of gradient plasticiza-
ß 2003 John Wiley & Sons, Ltd. tion along the radial direction of the fibers. That is,
through slight benzylation treatment, the skin
layers of sisal fibers are converted into thermoplas-
KEYWORDS: biofibers; biomaterials; composites; tic material while the cores of the fiber cells remain
sisal; biodegradable unchanged. In the course of hot pressing, the
plasticized parts of sisal are able to flow serving
as matrix resin and the unplasticized cores of the
*Correspondence to: Dr Ming Qiu Zhang, Materials Science
Institute, Zhongshan University, Guangzhou 510275, P. R. fibers stand in the form of fibrous reinforcement.
China. The resultant products fall into the category of
E-mail: ceszmq@zsu.edu.cn self-reinforced composites. The feasibility of this

Received 12 July 2003

Copyright ß 2003 John Wiley & Sons, Ltd. Accepted 30 July 2003
 Enzyme Degradability of Benzylated Sisal / 677

idea has been proved in our earlier work [5], and To produce composite plates of modified sisal
the processing–structure–property relationships of fibers, the above benzylated sisal fibers were com-
the composites have also been investigated in detail pressed into sheets using a hot press at 160
C
elsewhere [6]. Besides the easy processing and low under 9.8 MPa.
production cost, the experimental results indicate Enzymolysis of the materials was carried out by
that the self-reinforced composites of sisal have using cellulase from aspergillus niger (ICN, Corp.,
improved mechanical performance (e.g. flexural activity >600,000 unit/g solid). The materials to be
strength: 87.8 MPa, flexural modulus: 3.3 GPa, and degraded by the enzyme, were either sisal as-
unnotched Charpy impact strength: 33.9 kJ/m2), received or benzylated sisal ground into 20–40
which is comparable to conventional short glass mesh, while the self-reinforced composites of sisal
fiber reinforced synthetic polymer composites. took the form of sheets (6.5  0.9  0.3 cm3). The
Considering that one of the main reasons for the vacuum dried specimens and cellulase were put
preparation of composite materials employing lig- together in certain proportion into the buffer solu-
nocellulosic fibers results from the common inter- tion of acetic acid-sodium acetate with water bath
ests in their biodegradability, the degradation at the desired temperature. After a given time, the
habits of the newly developed sisal composites in specimens were taken out of the reactor, washed
different environments should be evaluated. As thoroughly, and dried in vacuum. Variations in
stated before, the chemical modification of the weight (of sisal fibers and the composite sheets)
fibers used for plasticization follows the route of and mechanical properties (of the composites)
benzylation, which takes place mostly at the side before and after the enzymolysis were then deter-
chains of cellulose of plant fibers. The hydroxyl mined to show the effect of enzyme-aided biode-
groups of cellulose are substituted by benzyl gradation. All the chemicals and solvents used in
groups, but the backbone structures of cellulose this work belong to analytic grade without further
might not be affected in principle. Therefore, the treatment or purification.
plasticized sisal should still be biodegradable like Infrared spectroscopy analysis was carried out
the unmodified version. using a Bruker Equinox 55 Fourier transform infra-
To the authors’ knowledge, biodegradabilities red (FT-IR) spectrometer. Surface morphological
and variation of mechanical properties after degra- changes due to biodegradation tests were observed
dation of the lignocellulosic materials with certain using a Hitachi S-520 and a Philips XL30 FEG
thermoplasticity have not yet been systematically scanning electron microscopes.
documented, in spite of the fact that the biodegra- Flexural properties of the composites were
dation of the derivatives of cellulose, like cellulose determined by a LWK-5 universal tester at a cross-
acetates, have been reported in the literature [7]. head speed of 10 mm/min in accordance with
The objective of the present article is thus focused GB3354-82 standard. Unnotched Charpy impact
on one of the most fundamental aspects of the strength was measured by an XJJ-5 impact tester.
biodegradability of the modified sisal and its All the reported data were the average of five
composites, i.e. enzymatic degradation. It is successful tests.
hoped that the results will give a deeper under-
standing of the all-plant fiber composites and their
RESULTS AND DISCUSSION
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life cycle.

Like other lignocellulosic fibers, sisal consists of

EXPERIMENTAL
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cellulose, hemicellulose and lignin. Since cellulose

constitutes the majority of sisal and lignin contains
Sisal fibers with diameter ranging from 100 to only a few hydroxyl groups, the benzylation reagent
200 mm were provided by Dongfanghong State that provides the fibers with thermoplasticity, benzyl
Farm in Guangdong Province, China. Chopped chloride, has to react mainly with the hydroxyl
sisal fibers that had been extracted by benzene- groups of cellulose. In this context, benzylated sisal
ethanol (v/v ¼ 2/1) were added into NaOH solu- still belongs to the derivative of cellulose. So long as
tion of desired concentration with stirring at 80
C. cellulose is degraded, catastrophic decay of mechan-
After 1.5 hr, the fibers were transferred into a flask ical performance of the plant fibers and their compos-
containing benzyl chloride. Benzylation reaction ites would take place as it acts as the predominant
was carried out under vigorous stirring at certain component of the fibers. For this reason, cellulase is
temperatures for a period of time to get benzylated employed by the authors of the present work to
products with varying extents of reaction. Then, the study the biodegradability of the modified sisal
products were purified through washing with dis- and its composites. The working principle of cellu-
tilled water to remove inorganic salts, and with lase to catalyze the breakdown of cellulose can be
ethanol to remove residues of benzyl chloride and simply illustrated by the following processes [8]:
by-products, respectively. Finally the treated sisal
was dried under vacuum at 60
C until constant
weight was reached. The extent of benzylation is
evaluated by the percentage weight gain after
benzylation of sisal fibers. High weight gain
means great extent of benzylation [2].

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
678 / Lu et al.
That is, cellulose (Cx) is attacked by endo-glucanase
(Ex) leading to the scission of
1, 4-glucosidic
bonds and the generation of amorphous cellulose
and soluble oligosaccharide (Co). Then, the resul-
tant oligosaccharide (Co) is either directly decom-
posed into glucose (C1) by the action of exo-
glucanase (Eo) or hydrolyzed into cellobiose (C2)
by cellobiase (E2), which is subsequently hydro-
lyzed into glucose (C1) by
-glucosidase (E1).
So far, many methods have been developed to
evaluate biodegradability of polymers, such as
analysis of structure, examination of degree of
polymerization, weight loss, variation in mechan-
ical performance and product of enzymolysis
[9, 10]. Due to the structural complexity of plant
fibers, only the changes in infrared spectroscopy
characteristics, weight and mechanical properties
of the materials before and after enzymolysis are
taken as the measures of the enzymatic degradation
in the present article.
It would be a reasonable starting point to check
the biodegradability of sisal fibers first, prior to the
study of the composites, which might provide the
knowledge basis for a better understanding of the
later results. Figure 1 shows the results of cellulase-
aided degradation of sisal fibers as a function of
time. For the convenience of discussion, the data of
cotton pulp, that is almost full of cellulose, is also
plotted in Fig. 1 as a reference. It is seen that
enzymolysis of sisal fibers proceeds mainly at the
beginning stage. After 48 hr, the rate of material
removal becomes rather low. As viewed from the
structural features of plant fibers, lignin might be
one of the main factors that influence the biode-
gradability of plant fibers. Each fiber cell is essen-
tially a composite in which rigid cellulose
FIGURE 1. Time dependence of weight loss of (1) sisal fibers, (2), (3) and (4) benzylated
sisal fibers and (5) cotton pulp due to enzymolysis. Conditions of enzymolysis: pH 5.0;
reaction temperature, 40
C; cellulase-to-specimen weight ratio, 2%. Weight gains of the
benzylated sisal: (2) 17.2 wt%, (3) 25.0 wt%, and (4) 44.8 wt%.
Copyright ß 2003 John Wiley & Sons, Ltd.
microfibrils are embedded in a soft lignin and
hemicellulose matrix [9, 10]. Lignin always blocks
the diffusion of cellulase towards cellulose. With a
rise in time, the cellulase solution diffusing from
the skin to the core of sisal cells encounters more
and more lignin. As a result, the production rate of
the enzymolytic substances is reduced. This analy-
sis can be supported by the enzymolysis of the
refined cotton pulp containing a little lignin (cellu-
lose content >97.5%) in Fig. 1. That is, the weight
loss and the rate of weight loss of cotton pulp due
to enzymolysis are much greater than those of
untreated and benzylated sisal fibers.
In addition, it is also seen from Fig. 1 than an
increase in the extent of benzylation corresponds to
increased rate of weight loss as well as the ultimate
weight loss of sisal fibers. This reveals that the
plasticization approach applied to sisal fibers in
the current work exerts an accelerative effect on the
enzymolysis, owing to (i) partial removal of lignin
from sisal during the pretreatment by NaOH, (ii)
expansion of interstitial volume inside the rigid
cellulose microbibrils, and (iii) decrystallization of
the orderly arranged cellulose molecules as a result
of the introduction of the benzyl groups. For highly
substituted sisal, much more crystalline regions of
cellulose are destroyed so that the diffusion of
cellulase solution becomes more easily.
To enhance the enzymolysis efficiency and to
further confirm the above analysis dealing with the
negative influence of lignin on lignocellulosic mate-
rials’ biodegradability, the effect of lignin removal
from sisal should be investigated. The experiments
were conducted as follows. The specimens that had
already experienced enzymolysis for 192 hr were
treated with 35% NaOH solution at 80
C for 2.0 hr
Polym. Adv. Technol., 14, 676–685 (2003)
 Enzyme Degradability of Benzylated Sisal / 679

FIGURE 2. Time dependence of enzymolysis induced weight loss of (1) sisal fibers, (2)
and (3) benzylated sisal fibers. Prior to the experiments, all the fibers had been degraded
by cellulase solution for 192 hr and then the newly exposed lignin was partially removed
by NaOH treatment. Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C;
cellulase-to-specimen weight ratio, 2%. Weight gains of the benzylated sisal: (2) 25.0 wt%
and (3) 44.8 wt%.
to remove the exposed lignin. Then, the materials striking contrast to the fact that the degradation
were filtrated and washed with distilled water to processes nearly terminated at the reaction of
pH 6–7, and dried under vacuum at 60
C until 192 hr before the delignification (Fig. 1).
constant weight was reached. The partially deligni- The chemical structure of benzylated sisal
fied specimens were decomposed by cellulose once fiber after enzymolysis has remarkably changed,
more, and the results of weight loss are recorded as illustrated by the FT-IR spectra in Fig. 3.
in Fig. 2. Evidently, the fibers keep on losing weight The absence of the absorptions at 1800–1950, 1600,
in the environment of the enzyme. It presents a 736 and 695 cm  1, which are characteristic of

FIGURE 3. FT-IR spectra of (1) benzylated sisal fibers with weight gain of 44.8 wt% and (2)
fibers biodegraded in cellulase. Conditions of enzymolysis: pH 5.0; reaction temperature,
40
C; cellulase-to-specimen weight ratio, 2%; reaction time, 192 hr.

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
680 / Lu et al.

FIGURE 4. SEM micrographs of (a) untreated sisal fibers, (b) untreated sisal fibers
having been enzymolyzed for 192 hr, (c) benzylated sisal fibers, and (d) benzylated
sisal fibers having been enzymolyzed. Conditions of enzymolysis: pH 5.0; reaction
temperature, 40
C; cellulase-to-specimen weight ratio, 2%; reaction time, 192 hr.

mono-substituted benzene rings of benzyl groups,
displays the removal of benzyl groups in benzy-
lated sisal fiber after enzymolysis. Besides, the
appearance of the absorption band at 1730 cm  1
corresponding to carbonyl groups and aldehyde
groups is indicative of lignin and hemicellulose in
the residue of the benzylated sisal fiber after enzy-
molysis. According to these phenomena, it can be
deduced that the plasticized skin layers of sisal
have been completely decomposed by cellulase
under the given conditions, and the remains are
the unmodified core portions of sisal because of the
gradual diffusion of the buffer solution containing
enzyme outside in.
To give a direct image of the effect of cellulase-
aided biodegradation, morphologies of sisal fibers
before and after enzymolysis are given in Fig. 4. For
untreated sisal, the attack of cellulase leaves splits
and cavities on the cell walls (cf. Fig. 4(a) and (b)).
However, the skeletons of the cells still exist because
of the hindrance of lignin, which coincides with the
results and analyses of Fig. 1. In the case of benzy-
lated sisal, the rough surface of the fiber becomes
relatively smooth after enzymolysis, strongly sug-
gesting that the modified outer layers have been
removed during enzymolysis (cf. Fig. 4(c) and (d)).
For enzymolysis, temperature is a very impor-
tant influencing factor. It not only affects the rate of
enzymolysis, but also affects the activity of cellu-
lase. Similar to other chemical reactions, rate of
enzymolysis increases when the temperature goes
up. However, the activity of cellulase decreases
with increasing temperature due to denaturation,
which slows down enzymolysis. As a result, it is
necessary to choose an appropriate temperature for
enzymolysis. As shown in Fig. 5, weight loss of
untreated and benzylated sisal peaks at a value of
about 40
C. When the reaction temperature exceeds
50
C, the weight loss remarkably decreases
obviously because of the reduced activity of cellu-
lose. It means the competition between the two
opposite factors reaches an equilibrium near 40
C.

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
 Enzyme Degradability of Benzylated Sisal / 681

FIGURE 5. Effect of temperature on enzymolysis induced weight loss of (1) sisal fibers
and (2) benzylated sisal fibers with weight gain of 44.8 wt%. Conditions of enzymolysis:
pH 5.0; cellulase-to-specimen weight ratio, 2%; reaction time, 48 hr.

Besides temperature pH value of the buffer activity of cellulose and promotes the biodegrada-
solution that serves as the reaction medium also tion [7].
influences the enzymolysis of the materials. The It is worth noting that enzymatic degradation of
maximum weight loss of both untreated and ben- cellulose is a reversible reaction, which can be
zylated sisal appears at a pH value of 5.0 (Fig. 6). illustrated by the following formula [11]:
Excessively high or low acidity would restrain the
activity of cellulase, leading to reduced rate of
enzymolysis. Only an appropriate range of pH
value of the buffer solution helps to retain high

FIGURE 6. Effect of pH value of enzyme solution on enzymolysis induced weight loss of

(1) sisal fibers and (2) benzylated sisal fibers with weight gain of 44.8 wt%. Conditions of
enzymolysis: reaction temperature, 40
C; cellulase-to-specimen weight ratio, 2%;
reaction time, 48 hr.

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
682 / Lu et al.
FIGURE 7. Effect of cellulase dosage (expressed in terms of cellulase-to-specimen
weight ratio) on enzymolysis induced weight loss of (1) sisal fibers and (2)
benzylated sisal fibers with weight gain of 44.8 wt%. Conditions of enzymolysis:
pH 5.0; reaction temperature, 40
C; reaction time, 48 hr.
When the amount of the specimen ([S]) was given,
the amount of cellulase ([E]) determines the enzy-
molysis rate of cellulose. It is found from Fig. 7 that
there is a critical value for the cellulase-to-specimen
weight ratio with respect to the weight loss of the
sisal fibers. When the cellulase-to-specimen weight
ratio is less than 2%, the degree of fiber degradation
increases with increasing the dosage of cellulase.
Afterwards, the weight loss of the specimens
remains almost constant. It means that excess cel-
lulase is useless due to the limited amount of the
active reaction sites on the fibers.
So far, it can be concluded from the earlier
discussion that the optimal way for enhancing
enzymolysis of sisal with the present cellulase, no
matter whether the fibers have been chemically
modified or not, should be conducted at 40
C in
the buffer solution of pH value of 5.0 where the
cellulase-to-specimen weight ratio is 2%. Therefore,
the biodegradation of self-reinforced composites of
sisal discussed hereinafter has followed these con-
ditions.
In comparison with the results observed in the
fibrous state of sisal within the same testing time
range (Fig. 1), the weight loss of the molded self-
reinforced composites from sisal is much less
(Fig. 8). It suggests that the composites are less
susceptible to enzyme-aided biodegradation than
the raw materials. This can be attributed to the
significantly increased packing density of the
molded sheets. The buffer solution of cellulase
can only migrate into the sheets through the surface
defects, and hence the reaction probability is
greatly decreased accordingly. As manifested by
scanning electron microscopy (SEM) observation
(Fig. 9), there are a number of cracks and voids on
Copyright ß 2003 John Wiley & Sons, Ltd.
the surface of the composites experienced enzymo-
lysis (cf. Fig. 9(a) and (b)). It again demonstrates
that the biodegradation is initiated at the sample
surface and then occurs inside the material with the
diffusion of cellulase.
Since chain scission of cellulose due to enzymo-
lysis weakens the lignocellulosic cell walls, the
mechanical performance of the self-reinforced
sisal composites would certainly decay. Unexpect-
edly, the reduction in flexural stiffness and strength
as well as impact toughness of the composites after
enzymolysis is not significant (Figs 10, 11 and 12).
In addition, the decrement of the mechanical prop-
erties induced by enzymolysis seems not to vary
with the extent of benzylation of the fibers. It not
only manifests that the composites have high
damage tolerance, but also helps to understand
the mechanism involved. For the current self-
reinforced sisal composites, it can be deduced that
enzymolysis of the plasticized skin layers of sisal
fibers (i.e. the matrix) plays a leading role. Owing to
the inherent compatibility between the plasticized
parts and unplasticized parts of sisal, the reinforce-
ments of the composites are hard to be accessed
by the cellulase solution and hence are still able
to provide loading carrying ability to a great
extent.
CONCLUSIONS
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(1) Although a certain amount of hydroxyl groups
of sisal have been substituted by benzyl groups
during the thermoplasticization process, the
inherent biodegradability associated with
Polym. Adv. Technol., 14, 676–685 (2003)
 Enzyme Degradability of Benzylated Sisal / 683

FIGURE 8. Time dependence of weight loss of self-reinforced sisal composites due to

enzymolysis. Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C; cellulase-
to-specimen weight ratio, 2%. Weight gains of the benzylated sisal: (1) 17.2 wt%, (2)
25.0 wt%, and (3) 44.8 wt%.

FIGURE 9. SEM micrographs of (a) surface of self-reinforced sisal composite sheet

and (b) surface of self-reinforced sisal composite sheet having been enzymolyzed.
Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C; cellulase-to-specimen
weight ratio, 2%; reaction time, 192 hr.

plant fibers still remains in either the benzy-
lated fibers or the resultant self-reinforced com-
posites, as revealed by their decomposition
behaviors induced by cellulase. It means that
the preparation of sisal self-reinforced compo-
sites does not increase the environment’s load.
(2) Depending upon the activity of the enzyme
used and the structural features of the materials
to be degraded as well, enzymolysis of sisal
fibers and their modified versions is influenced
by many factors, such as cellulase dosage, pH
value of the enzyme solution, reaction tempera-
ture and reaction time. It is necessary to select
appropriate conditions for each enzyme/plant
fiber pair to obtain the optimal biodegradation
effect.
(3) The enzymatic degradation of the benzylated
sisal fibers and their composites is decelerated

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
684 / Lu et al.

FIGURE 10. Deterioration of flexural modulus of self-reinforced composites of sisal.

Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C; cellulase-to-specimen
weight ratio, 2%; reaction time, 192 hr.

FIGURE 11. Deterioration of flexural strength of self-reinforced composites of sisal.

Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C; cellulase-to-specimen
weight ratio, 2%; reaction time, 192 hr.

Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)
 Enzyme Degradability of Benzylated Sisal / 685

FIGURE 12. Deterioration of impact strength of self-reinforced composites of sisal.

Conditions of enzymolysis: pH 5.0; reaction temperature, 40
C; cellulase-to-specimen
weight ratio, 2%; reaction time, 192 hr.

by lignin, which cannot be hydrolyzed by cel- 3. Simon J, Muller HP, Koch R, Muller V. Thermoplas-
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plant fiber composites, I. Unidirectional sisal fiber
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ACKNOWLEDGMENTS
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based on sisal. Adv. Compos. Lett. 2001; 10: 73–79.
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Copyright ß 2003 John Wiley & Sons, Ltd. Polym. Adv. Technol., 14, 676–685 (2003)