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Colloids and Surfaces A 604 (2020) 125311

Contents lists available at ScienceDirect

Colloids and Surfaces A


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

Preparation, characterization and antimicrobial activity of grafted cellulose T


fiber from durian rind waste
Rosliana Lubisa,b, Basuki Wirjosentonoc,*, Eddyantoc,d, Athanasia Amanda Septevanie
a
Postgraduate School, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara, Jl. Bioteknologi No.1, Medan 20155,
Indonesia
b
Department of Sains dan Teknologi, Universitas Medan Area, Sumatera Utara, Indonesia
c
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara, Jl. Bioteknologi No.1, Medan 20155, Indonesia
d
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Medan, Sumatera Utara, Indonesia
e
Research Center for Chemistry, Indonesian Institute of Sciences, Jakarta, Indonesia

G R A P H I C A L A B S T R A C T

A R T I C LE I N FO A B S T R A C T

Keywords: In this work, novel strategy for the low-cost and facile grafting copolymerization between isolated cellulose from
Grafting durian rind waste (DRC) and 2-[acryloyloxyl] ethyltrimethylammonium chloride (CIAETA) initiated with po-
Copolymerization tassium persulfate was developed. Subsequently, the grafting yield of 30.4 % was obtained. Comparative
Durian rind waste characterization of the ungrafted and grafted cellulose through techniques such as FTIR, SEM, XRD and ther-
Cellulose
mogravimetry confirmed the grafting of the CIAETA monomers onto DRC polymer backbone (DRC-g-CIAETA).
Antimicrobial
Grafting process resulting in formation of porosity of DRC and coarse structure, thus crystallinity index slightly
reduced from 48.45 to 36.58 %, however DRC-g-CIAETA increased in thermal stability. Water uptake capability
revealed a significant enhancement by almost three times due to the hydrophilicity of CIAETA monomer. In
addition, DRC-g-CIAETA demonstrated excellent antibacterial and antifungal ability against S. aureus, S. epi-
dermis, and C. albicans. These antimicrobial properties exhibited potential application in biomedical healthcare
fields.


Corresponding author.
E-mail address: basuki@usu.ac.id (B. Wirjosentono).

https://doi.org/10.1016/j.colsurfa.2020.125311
Received 16 June 2020; Received in revised form 15 July 2020; Accepted 15 July 2020
Available online 17 July 2020
0927-7757/ © 2020 Published by Elsevier B.V.
R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

1. Introduction showed antifungal activity without any cytoxicity effect [31]. Another
study also reported that the mechanism for the antimicrobial properties
In the past few years, an extensive research has been conducted on are correspond to the adsorption of positively charged of quarternary
developing antibacterial materials that can be incorporated into com- ammonium on the negatively charged cell surfaces of the microorgan-
monly used items to reduce the risk of bacterial infections [1]. The isms followed by diffusion through cell wall induced by long lipophilic
demand for hygiene, antibacterial products and personal care applica- alkyl chain [32]. Subsequently, binding, disruption and loss of cyto-
tions is increasing, especially health care supplies, have received con- plasmic membrane and constituents, resulting in inhibition of micro-
siderable amount of interest among researchers [2]. Traditional dres- organisms growth. Therefore, CIAETA is an interesting bioactive and
sings such as cotton wool has been replaced by advanced wound non-cytotoxicity materials.
nursing products made from biomass, such as hyaluronic acid [3], Herein, we report for the first time using CIAETA grafted onto cel-
chitosan [4] and bacterial cellulose [5] can attach tightly to the wound lulose fiber isolated from durian rind using Schiff base reaction. It has
without causing discomfort during removal. Cellulose is the most been well known that grafted cellulose via Schiff base reaction de-
abundant renewable biopolymer available in natural resources and at- monstrated strong antibacterial activity [25–34]. In addition, the
tracted a lot of attention owing to its, large-scale availability, cost-ef- CIAETA grafted onto cellulose was characterized with FT-IR, TGA/DTG,
fectiveness, eco-friendliness, sustainability and biocompatibility [6,7]. XRD and SEM, respectively. The water adsorbability and antimicrobial
Isolation of cellulose from agricultural waste has become more popular activity against S. aureus, S. epidermis, and C. albicans were also in-
[7] as a promising source for cellulose production such as oil palm vestigated.
trunk [8,9], sugarcane bagasse [10], vegetable waste [11], date palm
[12] and durian rind [13] 2. Methods and materials
In Indonesia, durian is one of the largest commodity and considered
as one of the biggest by-product which is increased from 65 ton in 2015 2.1. Materials
to 74 ton in 2017 and was predicted to increase by 900.000 ton/year for
the next 20 years [14]. Durian rind are the most promising cellulosic Duria rind was obtained from local market in Medan, Indonesia.
resource owing to its high cellulose content (60.54 %) and several Sodium metaperiodate and ClAETA were purchased from Sigma
components namely hemicellulose (13.09 %) and lignin (15.45 %) [15]. Aldrich. Methanol (70 wt.%), HNO3 (98 %), NaOH (98 %), NaOCl (98
Many efforts has been devoted to incorporate antibacterial agents into %) and acetone (90, wt%) were purchased from Merck Chemical.
cellulose such as chitosan [16], ZnO [17], metal nanoparticles [18–20] Bacterial strain of Staphylococcus aurous, Staphylococcus epidermis, and
and drug loaded [21] However, the antibacterial agents incorporated Candida albicans were obtained from Laboratory of Microbiology,
into cellulose commonly suffered from major leaching issues, which can Faculty of Medicine, Universitas Prima Indonesia. All chemicals were
be harmful due to the possible accumulation of toxic substance [22]. used without further purification.
Recent strategy to solve the leaching issues are chemically modified via
graft copolymerization of cellulose [21,22]. Isolated cellulose from
2.2. Preparation of oxidized cellulose fiber isolated from durian rind
sugarcane bagasse grafted with acrylamide and glycidyl methacrylate
was successfully obtained with significant improvement in antibacterial
Cellulose fibers were purified from the durian rind by following
properties [24]. Dopamine and montmorillonite grafted onto cellulose
similar process to our previous report for durian rind with modification
nanofibril demonstrated good antibacterial properties [25].
[13]. 75 g of cleaned durian rind was soaked into 1000 mL of HNO3
In general, antimicrobial surface was divided into two groups of
(3.5 wt%) and autoclaved. Afterwards, the obtained fiber were washed
leaching and non-leaching systems. Although the leaching systems are
for several times with distilled water until neutral pH was reached. The
efficient as antimicrobial, the practical applications are limited due to
process was continued by dispersing the fiber into 750 mL of NaOH
the suppression capacity to kill over time and cause contamination to
(2 wt%) and refluxed for 30 min at 70–80 °C. The fiber were then wa-
the environment [26]. Therefore, antimicrobial agent was fixed onto
shed using distilled water until the pH was neutral and the fiber im-
the surface of cellulose fibers through covalent bonding, which is an
mersed into 500 mL of NaOCl (1.75 wt%) at 70−80 °C for 30 min and
alternative approach trough grafting reaction of quarternary ammo-
washed until the neutral pH was achieved. Additionaly, α-cellulose was
nium such as 2-[acryloyloxyl] ethyltrimethylammonium chloride
obtained by treating the fiber into 500 mL of NaOH (17.5 wt%) and
(CIAETA), thus effectively against the gram-negative bacteria [27].
500 mL of H2O2 (10 wt.%) at 70−80 °C for 30 min, followed by
Moreover, the interaction between bacteria and active chlorine of
washing until the pH was neutral. 200 g of wet isolated cellulose was
quarternary ammonium perhaps became more efficient because the
dispersed in 2 L of distilled water and poured into handsheet. The pulp
permeability of the CIAETA could released an Cl+ and adsorbed by
then was pressed and the obtained sheet film was dried using vacuum
bacteria which is directly killed [28]. Generally, CIAETA is mainly
oven for overnight (Fig. 1).
composed of a quaternary ammonium salt group and an unsaturated
Prior to oxidation process, 5 g of isolated cellulose was homo-
vinyl group which could react with various vinyl monomer [29]. Pre-
genized using Meakida (Model ST43 DR SN.ZNST43DR) at speed
vious report suggests that CIAETA grated chitosan could enhanced the
3000 rpm. Subsequently, sodium metaperiodate (NaIO4:cellulose by
antibacterial activity [30] and nanocellulose crosslinked with CIAETA
ratio 0.6) was added and homogenized for 1 h. After 2 h, 20 mL of

Fig. 1. Photograph images of isolation process of cellulose fiber from durian rind casted film.

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R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

Fig. 2. Schematic illustration of synthetic route for oxidized DRC-g-CIAETA.

methanol was added into the dispersion. The obtained fiber was washed Where: Icr, I002, and Iam, referred to crystallinity index, intensity of
using distillated water for several times to obtained pH 7. crystalline region (22°), and intensity of amorphous region (18°).

2.3. Grafting of ClAETA onto cellulose 2.6. Water uptake capability

The oxidized cellulose (5 g) was dispersed in distilled water for 4 h Dried pristine and grafted DRC films were first weighed and (m0)
into three-neck round flask heated up to 50 °C, after 30 min, potassium soaked in distilled water for different time point at 1, 2, 3, 4, 5, 6, and
persulfate and 25 mL ClAETA 50 % were added into the solution to 7 h. Upon taking out the sample pieces from the solution, the clean
initiate the reaction. Grafting reaction was carried out at 80 °C under tissue paper was used to remove excessive water on the surface of
nitrogen atmosphere for 3 h, then the dispersion was cooled and me- sample and the second weight was recorded (m1). The swelling ratio of
thanol/acetone mixed solution was added to separate the enreacted each sample was calculated according to the Eq. (3).
monomer and the grafted cellulose. The obtained of grafted cellulose
Swelling ratio (%)= [[m1-mo]/mo] x 100 % (3)
fiber was dried in vacuum oven [30]

2.4. Determination of grafting yield 2.7. Antimicrobial activity

The grafted cellulose fiber were dried in vacuum oven at 60 °C until Gram positive bacterial, S. aureus and S. epidermis, and C. albicans
a constant weight was reached. The grafting yield (GY) was determined were used to determine the antimicrobial of pristine and grafted oxi-
gravimetrically and calculated as follows according to previous report dized cellulose fiber isolated from durian rind. The measurement was
[35]: performed using disc diffusion Kirby-Baauer (KB). The isolate of bac-
teria was cultured on nutrient agar (NA) medium, and fungi was cul-
GY (%) = [W2 – W1] / W1 x 100 % (1)
tured on potato dextrose agar (PDA) medium [36]. Each isolate with
Where W1 is the weight of cellulose before and W2 is the weight of the density of 108 was inoculated into physiological solution of NaCl
cellulose after grafting. 0.85 %. The density of bacteria and fungi was determined using a
standard solution of Mc. Farland. The concentration of modified cel-
lulose was varied, i.e. 25, 50, 75, and 100 %. Incubation was performed
2.5. Characterization
at 30 °C for 48 h [37].
The functional group of pristine and grafted oxidized cellulose was
determined by FT-IR Agilent Cary 630. The surface morphology char- 3. Results and discussion
acterization of cellulose and modified cellulose were determined using
scanning electron microscope (SEM) using JEOL EO JSM-6510LA. The 3.1. Grafting copolymerization of ClAETA onto oxidized cellulose fiber
thermal stability were performed by thermogravimetric analysis (TGA)
using TG/DTA STA 7300 at temperature range of 30−600 °C and The DRC was isolated via modified conventional bleaching method
heating rate of 10 °C min−1 under a nitrogen atmosphere to prevent [13]. In this study, the strategy of improving the antibacterial activity
thermoxidative degradation. The residual mass at 600 °C was directly of the DRC was to chemically anchor ClAETA with (R-N(CH3)+) group
obtained from the measurement data. X-ray difftraction (XRD) analysis via free radical polymerization from sulfate groups. In this reaction,
was employed using Shimadzu-610 to determine the crystallinity index cellulose pulp was used as the backbone of the whole structure, which is
using equation Segal [2]: initiated by heating process and the free radical species interact with
monomer and cellulose pulp. During the grafting process, the homo-
I002 − IAm polymer of CIAETA could be formed at the end of this process. The
ICr = x 100%
I002 (2) transformation of cellulose after oxidized and grafting can be seen in

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R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

Fig. 3. SEM images of oxidized DRC (a) before and (b) after grafted with CIAETA.

Fig. 2. The resulting oxidized DRC-g-CIAETA could be well dispersed in


water as shown in inset Fig. 2 with grafting yield about 30.4 %.
Fig. 3 displayed the SEM images with significant difference in the
surface morphology of before and after grafting CIAETA on to oxidized
DRC. Comparably, DRC-g-CIAETA appears to be coarser surface, which
implied that CIAETA could have been bond onto the DRC molecules,
leading to the enhancement of the surface density of fibrous ribbons of
grafted DRC. Notably, it can be clearly seen in Fig. 3b revealed that the
formation of smaller porosity after grafting process. Fig. 4 exhibits the
FT-IR spectra of pristine oxidized DRC and after grafting. The indicator
to prove the occurrence of grafting process can be determined by
comparing the transmittance of pristine with characteristic peaks at
3332, 2907, 1640, 1028 and 887 cm−1 corresponds to the OeH, CeH,
C]O, CeOeC and CeC stretching, respectively. After grafting process,
a new band was observed at 1729 cm−1 associated with the C]O ester
group molecular structure [38]. Another characteristic of CIAETA
modification at 1476 and 1217 cm−1 corresponds for the vibration of
trimethyl group of quaternary ammonium salt [39] and CeCeN Fig. 5. XRD patterns of pristine DRC and DRC-g-CIAETA.
asymmetric [40]. These further confirmed that CIAETA molecules were
chemically anchored onto oxidized DRC surface and may significantly
consistent with previous report of isolated cellulose from durian rind
enhance the density of positive surface charges (R-N(CH 3)+).
waste [13]. Similarly, grafted poly[(2-acryloyloxy)ethyl trimethyl am-
X-ray diffraction was utilized to investigate the crystalline structures
monium chloride) onto hydrolized starch backbone caused a reduction
of the pristine DRC and DRC-g-CIAETA samples was shown in Fig. 5.
in the crystallinity degree from 20.7 into 10.1 [43]. In addition, grafting
Cellulose fiber normally has semi-crystalline structure, which consisted
[2-(methacryloyloxy)ethyl]trimethylammonium chloride)] onto cotton
of amorphous and crystalline regions. The diffraction peaks appeared at
fiber demonstrated lower crystallinity than the untreated cotton [44].
2θ of 14.5, 15.8, and 21.1°, were assigned to the (1–10), (110) and
Guleria et al. also found that the crystallinity index of cellulose-g-poly-
(102), respectively [36,41]. The crystallinity index was calculated using
(acrylamide-co-acrylic acid) reduced to 36.58 % compared to pristine
Segal equation (eq. 1) [42], pristine DRC has higher crystallinity index
cellulose of 48.45 % [45]. The decrease of crystallinity index indicating
(26.19 %) than the grafting cellulose pulp (11.70 %). This finding is in
that the chemical bonding between CIAETA and DRC cause a distortion
in polymer backbone, which affecting the structure of cellulose. Fur-
thermore, the hydrogen bonds in cellulose was partly destroyed during
the polymer grafting with CIAETA, which is in consistent with previous
finding [46]. Besides, it also implying that the reduction in crystallinity
of CIAETA-g-DRC and an increase in amorphous region while com-
paring with pristine DRC. This also suggested that all CIAETA chains
were grafted on the surface of DRC, meanwhile hydroxyl groups did not
anchored during the graft polymerization process.

3.2. Thermogravimetry analysis

The thermal stability of the DRC before and after modification was
investigated. Fig. 6a and b shows the TGA and DTA curves of before and
after gradted DRC, while the corresponding parameters from TGA curve
are shown in Table 1. The result displayed the initial decomposition of
DRC before grafting process with an initial weight loss of 8.8 % at
55−110 °C, which indicating the dehydration of entrapped water in the
matrix of polymer and removal of moisture. The second step of thermal
degradation showed weight loss of 66.2 % at a range of 110−350 °C
Fig. 4. FTIR spectra of pristine DRC and DRC-g-CIAETA. could be due to loss of HCl and up to 89.2 % at the final decomposition

4
R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

Fig. 6. TGA dan DTG curves of (a) pristine DRC and (b) DRC-g-CIAETA.

Table 1 ratio increases with time for both pristine and grafted DRC. As in-
Thermal analysis data of cellulose pulp and oxidized cellulose pulp grafted. dicated, the increase in water uptake performance was shown to be
Samples T10% (oC) T50% (oC) Tonset (oC) Tmax (oC) Residue (%)
higher after the addition of the CIAETA grafted onto DRC by almost
three times. The significant improvement in the water uptake properties
DRC 166.66 312.19 270.96 315.50 10.80 of the grafted DRC was certainly due to the alkyl chain of the CIAETA
DRC-g-CIAETA 61.32 304.12 289.93 319.30 15.30 covalently bonded to the cellulose backbone, thus promoting the water
uptake into the cellulose structure [46]. This finding is also supported
by SEM analysis (Fig. 3b) due to the formation of porosity, which
temperature (FDT) of 550 °C can be ascribe to the oxidative degradation
leading to enhance the penetration of water molecules into cellulose
of the cellulose. In contrast, DRC grafted with CIAETA showed four
fiber. Accordingly, this result is in good agreement with previous re-
steps of degradation at 50–100, 100–240, 240–350, and 350−550 °C
port, which demonstrated lowered contact angle when introducing poly
correspond to the weight loss of 12, 45, 66, and 84 %, respectively.
[2-(methacryloyloxy)ethyl] trimethylammonium chloride [50]
Importantly, the FDT was higher for CIAETA-g-DRC compared to pris-
tine cellulose and was observed higher residual weight of 15.30 com-
pared to 10.80 % for pristine. TGA curves exhibited three exothermic 3.4. Antimicrobial activities
peaks at 52.60, 241.97 and 321.09 °C for both pristine and DRC-g-
CIAETA sample correlated to the evaluation of moisture, decomposition Antibacterial activity of DRC before and after grafting process was
of polymer and decomposition of impurities in polymer [47]. Grafting determined against Staphylococcus aureus, Staphylococcus epidermis, and
of the CIAETA on to cellulose enhances the thermal stability of the graft Candida albicans. According to the agar diffusion technique described
copolymers as is indicated by the higher FDP of grafted copolymers as above, we have determined the diameter of inhibition zone, which
compared to the pristine cellulose. This can ascribe to the increased of appeared around the tested samples. Fig. 7b exhibited the different
grafting and formation of three dimensional networks due to in- diameter around the samples after incubation for 48 h in the agar. No
corporation of covalent bonding of copolymer chains onto DRC [39,40] inhibition zone was observed around the pristine DRC with three dif-
ferent bacteria tested as shown in Fig. 8, whereas chloramphenicol was
used as the positive control. A large inhibition zone around grafted DRC
3.3. Swelling behavior with different strains of bacteria. We noted that the diameters of the
inhibition zones are greater in the case of DRC-g-CIAETA summarized in
Swelling behavior of cellulose fiber highly depends on the hydro- Table 2, which implying that the antibacterial agents of CIAETA [51].
philicity of the polymers immersed in aqueous solution to adsorb water This demonstrates that the grafting had a higher antibacterial activity
with difference in osmotic pressure [49]. Fig. 7 presents the swelling than pristine DRC and could further enhance the antibacterial activity.

Fig. 7. Swelling degree curve of grafted cellulose pulp and untreated cellulose pulp.

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R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

Fig. 8. Antibacterial activity of (a) pristine and grafted DRC on (b) S. aureus, (c) S. epidermis and (d) C. albicans MH agar plates.

4. Conclusions demonstrated strong antibacterial and antifungal activities.

Grafting copolymerization between DRC and CIAETA monomer in


the presence of potassium persulfate has been successfully obtained CRediT authorship contribution statement
with grafting yield of 30.4 %. Based on FTIR analysis, a characteristic
peaks at 1729, 1476, 1217 cm−1 after grafting process were assigned to Rosliana Lubis: Conceptualization, Data curation, Formal analysis,
the C]O ester, COO, and CeCeN asymmetric, respectively owing to Investigation, Methodology, Writing - original draft. Basuki
the CIAETA grafting process. SEM and XRD analysis demonstrated that Wirjosentono: Conceptualization, Data curation, Formal analysis,
the morphology of grafted DRC showed pore formation and coarse Methodology, Supervision, Writing - review &
surface, therefore the crystallinity index reduced from 48.45 to 36.58 editing.Conceptualization, Data curation, Investigation, Methodology,
%. The thermal stability of cellulose enhances with higher FDP and Supervision, Writing - review & editing. Athanasia Amanda
higher residual owing to the CIAETA grafting. The water uptake cap- Septevani: Data curation, Formal analysis, Investigation, Methodology,
ability of DRC-g-CIAETA improved significantly by almost three times Writing - review & editing.
by the presence of CIAETA monomer. Accordingly, the DRC-g-CIAETA

Table 2
Summary of diameter of inhibition zone against Staphylococcus aureus, Staphylococcus epidermis, and Candida albicans treated with pristine and grafted DRC.
Microbial/fungal Treatment Diameter of inhibition zone (mm)

25 % 50 % 75 % 100 %

S. epidermis Pristine 0 0 0 0
DRC-g-CIAETA 0 6.15 ± 0.23 6.75 ± 0.31 7.02 ± 0.26
Chloramphenicol 22.02
S. Aureus Pristine 0 0 0 0
DRC-g-CIAETA 0 7.15 ± 0.48 7.85 ± 0.53 8.30 ± 0.24
Chloramphenicol 25.75
Candida albicans Pristine 0 0 0 0
DRC-g-CIAETA 8.00 ± 0.52 9.06 ± 0.41 11.0 ± 0.35 16.02 ± 0.37
Chloramphenicol 7.56

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R. Lubis, et al. Colloids and Surfaces A 604 (2020) 125311

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transport and photon absorption of bimetallic Au-Ag nanoparticles on ZnO photo-
The authors declare that they have no known competing financial anode for photoelectrochemical enhancement under visible light, J. Phys. Chem. C.
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