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SULFURLESS CURE SYSTEM FOR CARBOXYLATED ACRYLONITRILE BUTADIENE

LATEX FILMS AND ITS CYTOTOXICITY PROPERTIES

Article · December 2015

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 Malaysian Polymer Journal, Vol. 10 No. 2, p 54-61, 2015
Available online at www.cheme.utm.my/mpj

SULFURLESS CURE SYSTEM FOR CARBOXYLATED ACRYLONITRILE

BUTADIENE LATEX FILMS AND ITS CYTOTOXICITY PROPERTIES
Lim, H.M.*#, Mok, K.L.* and Amir Hashim Md.Y.*

*Rubber Research Institute of Malaysia, Malaysian Rubber Board, P.O. Box 10150, 50908 Kuala Lumpur,
Malaysia

Corresponding author’s: e-mail: evelyn@lgm.gov.my

Abstract: Disposable synthetic gloves especially nitrile gloves have risen to become the glove of choice for
healthcare workers. However, residual chemicals may trigger allergy among its gloves wearers when they are
leached out from the glove during usage. Alternative vulcanizing system such as organic peroxide has been
found to perform as a crosslinker for nitrile polymer, but the uptake of this system by the glove dipping industry
has been slow. In this present study, zinc peroxide dispersion was used as an alternative compounding ingredient
in fabricating the nitrile latex films in replacement of the sulfur and zinc oxide system. The compounding of the
nitrile latex with zinc peroxide dispersion involved current manufacturing process and less materials usage. The
tensile strength and force at break value of the nitrile films cured with zinc peroxide dispersion were found to be
comparable with the typical nitrile films compounded with sulfur and zinc oxide formulation. The films also
showed higher tear strength and existed as a softer material with higher elongation at break value. The aged
films met the minimum requirements of a nitrile examination gloves.

Key words: carboxylated acrylonitrile butadiene latex, XNBR, nitrile, examination glove, zinc oxide, zinc
peroxide, cytotoxicity

1.0 INTRODUCTION
Nitrile gloves are widely used as medical examination
gloves as it exhibits acceptable barrier protection, good
strength and puncture resistance and good chemical
resistance. The rubber polymer is made up of a random
terpolymer of acrylonitrile, butadiene and methacrylic
acid. Through crosslinking the rubber polymer in the
latex, the strength and elasticity of the nitrile film
improves substantially. The nitrile crosslinking occurs
via the reaction of its carboxylic groups and the metal
oxide forming ionic crosslinks and conventional
sulfur/accelerator system forming covalent crosslinks1.
Ionomers formed through ionic crosslinks in
combination with acrylonitrile were found to increase
the toughness of nanostructured materials2. The
mechanical properties of acrylonitrile containing films
were better than the non-acrylonitrile containing
ionomers films3. On the other hand increase in
carboxylation improves chemical resistance4.
In conventional compounding formulation, organic
accelerator such as thiuram, carbamates and thiazole
are used to contribute to the final properties of the
nitrile latex film. However, these organic accelerators
may cause Type IV allergic contact dermatitis when
residual chemicals from the gloves come in contact with
human skin. The Type IV response begins when the
antigens penetrate the skin, triggering the formation of
T cells sensitized to the specific antigens. Currently,
carbamates are the most common accelerators used in
the manufacturing of nitrile gloves. Clinically, a Type IV
allergy presents as a red, raised and palpable area at the
area of contact with the glove, accompanied by
subjective symptoms such as itching, burning and
tingling. Additional symptoms include erythema,
swelling, cracking, itching, weeping and dryness of the
skin at the site of contact although dermatitis may
extend beyond the area of contact5.
Gloves manufacturers have been trying to establish an
alternative vulcanizing system without accelerator to
combat the related health issues. A method and
formulations to make nitrile gloves using organic
peroxide crosslinking system in combination with the
use of zinc oxide were disclosed6. Kazumi et al found
dibenzoyle peroxide as an effective crosslinker in nitrile
latex dipping applications7. Over the years synthetic
latex manufacturers and researchers also geared
towards developing self crosslinking polymers8. Both
systems showed promising laboratory results but none
have been implemented widely into nitrile glove dipping
production process due to its ease of operation and
cost. In this present investigation zinc peroxide, a
divalent metal peroxide was used as an alternative
compounding ingredient in producing the nitrile latex
dipped films. It is postulated that the zinc peroxide can
react with the carboxylated groups to form ionic
crosslinking and covalent crosslinking to take place
between the double bonds of polybutadiene chains. The
objective of the study is to develop a sulfur and
accelerator free system for nitrile latex that meets the
specification of a nitrile examination gloves. While some
of the previous study has focus into modifying the main
 Lim, H.M., Mok, K.L. and Amir Hashim Md.Y. Malaysian Polymer Journal, Vol. 10, No. 2, p 54-61, 2015
polymer chain and use of organic peroxide for
mechanical properties enhancement without the use of
accelerators. The current study will delve into use of
zinc peroxide as a stand-alone compounding ingredient
in producing nitrile films.
2.0 MATERIALS & METHODS
2.1 Preparation of zinc peroxide dispersion
The commercial zinc peroxide used contains 50-60% of
zinc peroxide and 40-50% of zinc oxide. The metal
peroxide is grinded into dispersion form prior to
addition to the carboxylated acrylonitrile butadiene
latex (XNBR) by using ball milling method according to
the formulation in Table 1. The zinc peroxide powder is
filled into unglazed cylinder with balls, it is then ball
milled for 22-24 hours under room temperature.
Table 1: Zinc peroxide (ZnO2) dispersion.
Parts by weight
Ingredients (%)
Zinc peroxide powder 40.0
Dispersing agent (egAnchoid) 2.0
Water 58.0
2.2 Preparation of XNBR compound
The XNBR was compounded according to the
formulation in Table 2. The stabilizer sodium dodecyl
sulphate (SDS) was added before the pH of the latex is
raised, followed by addition of vulcanizing ingredients
in parts per hundred rubber (pphr). The preparation of
XNBR compound with the conventional compounding
ingredients (sulfur and zinc oxide) is as described in the
earlier paper9.
Table 2: XNBR compound formulation.
Ingredients Dry (pphr)
45% XNBR 100
5% KOH 2.0
10% SDS 0.2
40% Zinc peroxide 1.0−5.0
2.3 Preparation of XNBR films
The total solids content of the XNBR was reduced to
different percentage with distilled water to obtain
dipped film of different thickness. Unglazed porcelain
plates were first heated to 70°C before dipping into a
20% calcium nitrate solution. The plates were oven dried
in an air oven set at 70°C before dipping into the latex
compound for 10 seconds. The resulting wet films were
air dried under room condition for 10 minutes before
being subjected to leaching in distilled water for 2
minutes. The leached films were then dried in the oven
set at 80±5°C for 10 minutes before heating up the oven
to 100± 5°C and again to 110±5°C for 10 minutes
respectively. The films were then removed from the
oven and cooled to room temperature, before being
powdered with corn starch and stripped from the
plates.
2.4 Mechanical properties of XNBR films
The tensile properties and tear strength of the unaged
and aged (70ºC/7 days) films were determined using an
Instron 5565 Testing Machine according to the ASTM
D412 and ISO 34 test method with a crosshead speed of
500 mm/min and 100 mm/min respectively. The test
was conducted under room temperature condition
(25±1ºC).
2.5 Particle size measurement
A SALD-2001 SHIMADZU Laser Diffraction Particle Size
Analyzer with a measuring unit and a sampler was used
to measure the particle size of the zinc peroxide
dispersion using laser light scattering method. The
measurement range of the Analyzer ranges from 0.03-
70 µm. The measuring unit consists of a light source
using semiconductor laser and an optical measuring
unit using a photosensor. The sampler uses a radial
pump and water supply valve.
2.6 Cytotoxicity
The cell line and the procedures used are in accordance
to the guidelines detailed in ISO-10993 Part 1 and 5.
Test sample was firstly sterilized via autoclaving
followed by extraction ingrowth medium at 5 ml of
medium per gram of sample. The extract was exposed
to L929 murine fibroblasts for 24 hours after which the
cell viability was determined using the MTT assay which
measures conversion of the tetrazolium salt (i.e. 3-[4,5-
dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide)
by the succinate dehydrogenase enzyme found in the
mitocondrias of living active cells10. The optical density
reading which relates proportionally to the number of
living cells, was measured at 570 nm. Results were
normalized to that observed in growth medium only.
3.0 RESULTS & DISCUSSIONS
3.1 Particle size of zinc peroxide dispersion
The zinc peroxide dispersion was successfully prepared
using the ball mill grinding method. The dispersion was
observed to be a finely ground dispersion. The particle
size distributions of zinc oxide and zinc peroxide
dispersion were obtained by diffraction method and are
shown in Figure 1. The average diameter of the zinc
peroxide dispersion was 0.89 µm. The value of d(0.5)
representing the 50% percentiles of the size distribution
was found to be 0.84 µm. Comparatively the mean
diameter of zinc oxide dispersion was 0.62 µm and the
d(0.5) as 0.51 µm. As the particle size of the zinc
peroxide dispersion was found to be less than 5 µm,
though slightly larger than the zinc oxide dispersion, it
is expected that the dispersion can be added to the latex
system.
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100 100

Cumulative particle amount

Cumulative particle amount

75 75

50 50

25 25

0 0
0.5 1.0 1.5 2.0 2.5 3.0
0.5 1.0 1.5 2.0 2.5 3.0

Particle diameater (µm) Particle diameter (µm)

(a) (b)

Figure 1: Cumulative particle size distribution of (a) zinc oxide and

(b) zinc peroxide dispersion.

3.2 XNBR crosslinked with zinc peroxide the 3600 - 3100 cm-1 region of the spectrum, which is
the stretching band of OH from the carboxylate group.
Combination of metal salt and carbon-carbon crosslinks Both films showed similar transmittance bands with the
may have taken place in the vulcanization of XNBR latex zinc oxide containing films showing lower intensity.
with zinc peroxide, as the peroxide used is a mixture of
zinc oxide and zinc peroxide. Ionic crosslinks are
known to form when zinc oxide is present with the
carboxylic group11. The zinc peroxide decomposes to
give zinc oxide and oxygen radicals with no other phase 100
transition when it is heated12 which may occur during
the vulcanization of the nitrile gloves. The curing of
XNBR latex with peroxides presumably occurred
Transmittance (%)

80
through the development of carbon to carbon linkages13.
The oxygen radicals might attack the double bonds of
the butadiene, the repeating monomers of XNBR to form
the crosslinks. 60

The carboxylic group environment and other functional

40
groups of the films were studied using FTIR as shown in
Figure 2. The characteristic band of the olefinic double
bond (-CH=CH-) groups14 from butadiene is 1640 cm-1. 4000 3500 3000 2500 2000 1500 1000 500
However this band could not be observed in the FTIR Wavenumber (cm-1)
spectrum for both films. The absorption band for un-
ionized carboxylate band15 is known to be at 1700 cm-1.
The XNBR films cured with zinc peroxide showed a
strong band at 1600 cm-1, this could be assigned to the
Figure 2: FTIR spectrum of XNBR film cured with zinc
carbonyl stretching vibration of zinc carboxylated salt.
peroxide (──) and zinc oxide (----).
This may indicate that zinc oxide acted as base and
neutralize the carboxylate groups, thus forming zinc
salt of carboxylic acid into the polymer16. Stretching of 3.3 Mechanical properties of XNBR films cured with zinc
nitrile triple bonds (C≡N) at weak peak of 2237 cm-1 was peroxide dispersion
evident in the FTIR spectra17. There was a broad band in
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 Lim, H.M., Mok, K.L. and Amir Hashim Md.Y. Malaysian Polymer Journal, Vol. 10, No. 2, p 54-61, 2015

The current practice in manufacturing nitrile gloves is
by using the sulfur and accelerator system. In our
current study, the nitrile films were fabricated with the
zinc peroxide dispersion. The tensile strength of the
nitrile latex compounded with zinc peroxide dispersion
at two different thicknesses is shown in Figure 3. As the
trend of nitrile gloves in the current market are moving
towards thinner and lighter gloves, the properties of the
XNBR films cured with zinc peroxide were investigated
within the thickness range of commercial gloves.
Tensile strengths are measurements associated with
extreme conditions near to complete material failure18.
Without the presence of sulfur, the nitrile films still
achieved the minimum specification19 of tensile strength
(14 MPa) at the lowest dosage although it was lower
compared to zinc oxide containing nitrile films.
However at higher dosage at 3 phr, the tensile strength
of the nitrile films increased and was found to have
comparable strength with the zinc oxide containing
nitrile films. As the dosage of the zinc peroxide
dispersion continued to increase at above 3 phr, the
tensile strength of the nitrile films was above 30 MPa.
The crosslinking that had occurred has significant
impact on the tensile strength for both type of films20.
The force at break value of all the nitrile films
compounded with zinc peroxide dispersion were also
more than 6 N except the 2 phr films at 0.05 mm
thickness. With less compounding ingredient, the films
achieved the minimum specification21 (6 N) for nitrile
examination gloves as shown in Figure 4. Generally the
zinc peroxide containing nitrile films had higher force
at break value than the zinc oxide containing nitrile
films when it is more than 3 phr. The forces at break
behaviour of the films were similar to its tensile
strength.
The elongation at break value of the nitrile films
containing zinc peroxide dispersion were higher
compared to the zinc oxide containing nitrile films. The
films elongated higher than the conventional
formulated nitrile films as shown in Figure 5, indicating
that the films containing zinc peroxide dispersion were
softer22. All the elongation at break values of the nitrile
films was higher than 500% and met the nitrile
examination gloves requirement. The modulus 300
values in this study also reflected that the zinc peroxide
containing nitrile films were softer (3 – 4 MPa) as
compared to zinc oxide (7 – 8 MPa).

0.05 mm films 0.06 mm films

Figure 3: Tensile strength of XNBR films at different thickness cured with zinc peroxide (white bar) in comparison with
zinc oxide (grey bar).

0.05 mm films 0.06 mm films

Figure 4: Force at break of XNBR films at different thickness cured with zinc peroxide (white bar) in comparison with
zinc oxide (grey bar).

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 Lim, H.M., Mok, K.L. and Amir Hashim Md.Y. Malaysian Polymer Journal, Vol. 10, No. 2, p 54-61, 2015
0.05 mm films
Figure 5: Elongation at break of XNBR films at different thickness cured with zinc peroxide (white bar) in comparison
with zinc oxide (grey bar).
Figure 6 shows the tear strength of the nitrile latex
compounded with zinc peroxide dispersion compared
with the nitrile latex compounded with zinc oxide
dispersion at different dosage of dispersion. The films
compounded with zinc oxide showed significant lower
tear strength value. Nitrile films compounded with zinc
peroxide dispersion showed tear strength value of more
than 5 N/mm. The tear strength of the films made from
the zinc peroxide dispersion was more superior
compared to the films made from the zinc oxide
dispersion. The tear strength of the nitrile films are well
known to be more inferior as compared to the natural
rubber latex films. Nitrile films made from the zinc
peroxide dispersion might be able to narrow the gap of
tear strength value with the natural rubber latex films.
The mechanical properties of the aged nitrile films are
shown in Figure 7. The behaviour of the aged nitrile
films containing zinc oxide was studied previously9 and
shall not be described further here. All the films met
the minimum specifications of a nitrile examination
glove in terms of tensile strength and force at break,
except the 0.05 mm nitrile films containing 1 phr of
zinc peroxide dispersion. There was also no significant
change in the elongation at break value of the films
after ageing as compared to the unaged films, indicating
that the nitrile films were not stiffer after ageing and no
weakening of the polymer matrix after thermal ageing23.
The films also maintained its tear strength properties
after being subject to ageing conditions. Retention of
the film’s mechanical properties indicated mild
degradation of polymer molecules24.
3.4 Cytotoxicity properties of XNBR films in the presence
of zinc peroxide dispersion
Extent of toxicity exerted by the extracts prepared from
films compounded with different amounts and types of
curatives is shown in Table 3 below. For this part of the
study, toxicity was tested at two different
concentrations (i.e. neat and 10X dilution) in case no
distinct result was observed with one concentration.
0.06 mm films
Comparing cell performance at these two
concentrations enables one to gauge improvement in
biocompatibility. When the extracts were tested at neat
concentration, all samples caused massive cell death
with extremely low, almost negligible cell viability. This
could be due to the presence of residual ZnO and other
chemicals (if any) present in the extracts from both
formulations. Leaching of chemicals from products has
been invariably implicated to trigger toxicity25.
When the extracts were tested at 10X dilution, a clearer
ranking was seen with improved cell viability for all
samples. Dilution is expected to alleviate toxicity and
condition the extract to a concentration whereby its
toxicity is sufficiently potent to discriminate between
samples without causing infinite cell death. Results
show that at 10X dilution, extracts from the zinc
peroxide formulation consistently gave higher cell
viability than the absolute ZnO formulation, suggesting
that zinc peroxide was more tolerable by cells and less
toxic. It is noteworthy to mention that at this dilution
factor, biocompatibility of the zinc peroxide
formulation was similar to that of the cell growth
medium (normalized to 100%), indicating that toxicity
was essentially negligible.
Unexpectedly, at 10X dilution, the absolute ZnO
formulation showed improved cell viability with
increasing amount of ZnO used. The reason for this is
unknown however it should be clarified that thetoxicity
assay used in this study measurescell responses
towards residual chemicals that are extracted into
aqueous medium. The amount of residual chemicals in
the extract depends on how readily these chemicals can
be leached out into the extract. Hence, the initial total
chemicals used in any formulation may not always
relate proportionally to the toxicity. Within the limit of
experiments carried out in this study, the amount of
residual ZnO and other chemicals (if any) present in the
extracts was not examined. Therefore the trend noted
with absolute ZnO formulation could not be interpreted
further.
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0.05 mm films 0.06 mm films

Figure 6: Tear strength of XNBR films at different thickness cured with zinc peroxide (white bar) in comparison with
zinc oxide (grey bar).

Figure 7: Mechanical properties of aged XNBR films at 0.05 mm thickness (grey bar) and 0.06 mm thickness (white bar).

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 Lim, H.M., Mok, K.L. and Amir Hashim Md.Y. Malaysian Polymer Journal, Vol. 10, No. 2, p 54-61, 2015
Table 3: Cell viability of L929 fibroblasts exposed to extracts prepared from ZnO and ZnO2formulations. Extracts were
tested neat and 10X dilution in growth medium.
Sample Tested at Cell viability (%)
1.0 phr ZnO Neat
3.0 phr ZnO Neat
5.0 phr ZnO Neat
1.0 phr ZnO2 Neat
3.0 phr ZnO2 Neat
5.0 phr ZnO2 Neat
4.0 SUMMARY
An alternative vulcanization system without the use of
sulfur and accelerator was developed for nitrile gloves.
The zinc peroxide dispersion was prepared using the
ball mill grinding method and successfully used as a
compounding ingredient in the nitrile latex system. FTIR
results showed that the carboxylate groups in the films
were ionically bonded by zinc ions. The nitrile films
cured with zinc peroxide dispersion showed comparable
mechanical properties with higher elongation and tear
strength as compared to the sulfur and accelerator
system. The aged films maintained its mechanical
properties as well. The superior mechanical properties
were probably due to the crosslinks provided by the
zinc peroxide compound. Improvement in
biocompatibility with lower toxicity potency was
observed in these films.
5.0 ACKNOWLEDGMENTS
The authors would like to thank the Director General of
the Malaysian Rubber Board for the permission to
publish this paper. The authors are also grateful to Mrs
Zuliza Ahmad, Mrs Sevensiatina Harris and Mr Syahril
Zainul for the assistance rendered.
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