Cross-linked soy-based wood adhesives for plywood

H. Lei
n
, G. Du, Z. Wu, X. Xi, Z. Dong
Materials and Engineering College, Southwest Forestry University, Kunming 650224, Yunnan, PR China
a r t i c l e i n f o
Article history:
Accepted 22 January 2014
Available online 6 February 2014
Keywords:
Soy adhesive
Cross-linker
Water resistance
Plywood
a b s t r a c t
To improve the water resistance of soy-based adhesive for wood panels, three kinds of cross-linkers,
namely, epoxy resin (EPR), melamineformaldehyde (MF) and their mixture EPRMF were used in this
paper. The results indicated that all the three cross-linkers improved the water resistance of soy-based
adhesive and the hybrid cross-linker EPRMF, was the best. With press temperature 160 1C and press
time 8 min, type II and even type I plywood could be prepared when 6.4%EPR6.4%MF is used as cross-
linker of soy-based adhesive. FT-IR indicated that the great improvement of water resistance of soy-based
adhesive modied with EPR and MF might be caused by the reaction between epoxy and OH, and that
between MF and NH.
& 2014 Elsevier Ltd. All rights reserved.
1. Introduction
Formaldehyde-based adhesives, such as ureaformaldehyde (UF),
melamineformaldehyde (MF), phenolformaldehyde (PF), are widely
used for the preparation of wood panels. But formaldehyde emission
caused by these resin adhesives has confused wood industry and has
been a topic of concern for many years. Some standards or require-
ments were given to dene the acceptable formaldehyde emission
levels. The newest requirement on formaldehyde emission comes
from California Air Resources Board (CARB) formaldehyde emissions
regulation of U.S. It was passed in 2008 and got effective in 2009.
Today, the mounting interest in formaldehyde emission is still driving
major changes in wood panel industry as well as the resin industry
that supplies the wood panel industry. In response to the need on
environment-friendly adhesives, great attention has been given to
adhesives from natural materials, such as starch [1,2], soy-based
adhesives [35], and so on, although most of these adhesives have
almost been pushed out of market in wood panel industry during the
past 30 years.
Soy-based adhesive was once a major adhesive for preparation of
plywood. But it has been replaced by synthetic resins since the 1960s.
Till the 1990s, it returned to the study area as a wood adhesive. It is
reported that one of the soy-based formaldehyde-free adhesives has
been used for production of interior plywood panels since 2004 [6].
However, the application of soy-based adhesives is rather limited.
Now, most of the efforts on soy-based adhesive are given to the
improvement of its bad water resistance. To resolve this problem,
some methods could be employed to modify the soy adhesive, such
as hydrolysis, chemical denaturation, cross-linking, enzyme modi-
cation, and so on.
Cross-linking modication is a comparatively acceptable
method for the modication of soy-based adhesive. Cross-linkers
can be either mixed with soy adhesive directly before its applica-
tion or added during the preparation of soy adhesive. For the latter
method, acrylates [7,8], maleic anhydride [9], etc. are used and in
most cases graft polymerization will occur. Commonly, some
complex preparation procedures are involved in this method.
Therefore, it is much easier in handling to mix cross-linkers
directly with soy adhesive. An effective cross-linker is the key for
this method. Since there are many reactive groups in soy proteins,
such as OH, SH, COOH, and NH
2
, many chemicals could be
used for the cross-linking of soy adhesive. Epoxy [6], aldehyde and
its deratives [10] have already been proved effective cross-linkers
for soy-based adhesive. With different cross-linkers, the mechan-
ism for the improvement of performance of soy adhesive is
different. Epoxy groups are thought to react with all of the
aforementioned functional groups in soy proteins [11]. Huang J
et al. proposed the possible curing mechanisms of the
soypolyepoxide adhesives [12]. For cross-linker aldehyde and
its derivatives, such as ureaformaldehyde, hydroxymethyl phe-
nol, the main reaction group, comes from NH
2
in soy protein.
Besides choosing a suitable cross-linker, its addition amount is
very important for the application of soy adhesive. Because of the
usage of some expensive cross-linkers, such as epoxy, the cost of
soy-based adhesive is greatly dependent on the addition amount
of cross-linker. Wood composites bonded with soy protein isolate
and Kymene are reported to show shear strengths comparable to
or higher than those of composites bonded with phenolformal-
dehyde [13]. As a wet-strength agent for paper, Kymene is an
aqueous solution of cationic polyamidoamineepichlorohydrin
Contents lists available at ScienceDirect
journal homepage: www.elsevier.com/locate/ijadhadh
International Journal of Adhesion & Adhesives
http://dx.doi.org/10.1016/j.ijadhadh.2014.01.026
0143-7496 & 2014 Elsevier Ltd. All rights reserved.
n
Corresponding author.
E-mail address: honeyray2006@hotmail.com (H. Lei).
International Journal of Adhesion & Adhesives 50 (2014) 199203
(PAE). However, because of the high dry weight ratio SPI/Kymene
1.33:1, cross-linker Kymene is the most expensive component of the
soy-based adhesive. A new curing agent was developed by the same
research group from epichlorohydrin and ammonium hydroxide to
decrease the cost of soy-based adhesive. But there was still about 14%
on dry soy our weight of this curing agent needed for the
preparation of soy-based adhesive and interior plywood [6]. When
melamineureaformaldehyde (MUF) resin is added to soy-adhesive
as a cross-linker, the addition amount of solid MUF is about 40% on
solid soy our or even higher [14,15]. For phenolformaldehyde, the
weight ratio of phenolformaldehyde to soy adhesive was 30:70 in
public reports [16]. In this formulation phenolformaldehyde had a
solid content of 55% and soy solution of 42%.
In this paper, the effects of different cross-linkers on the water
resistance of soy-based adhesive were studied. In order to transfer
all of the possible hydrophilic groups of soy protein to hydro-
phobic ones, a hybrid cross-linker was used for the modication of
soy-based adhesive. The objectives of this work were as follows:
(1) to optimize the proportion of components of hybrid cross-
linker; (2) to decrease the addition amount of cross-linker; and
(3) to prepare plywood with good water resistance.
2. Materials and methods
2.1. Materials
Defatted soy our (53.4% protein content) was obtained from
Yuxin Soybean Protein Co., Ltd, China. Poplar veneer with a
thickness of 1.5 mm and moisture content of 810% was purchased
for the preparation of plywood. Epoxy resin (EPR) was a commer-
cial product with the name of E-44, whose epoxide number was
0.410.47 and softening point was 1220 1C. All other chemicals
mentioned in this work were all of reagent grade.
2.2. Preparation of soy-based adhesive
Soy-based adhesive was prepared according to a method already
reported [17]. A three-neck round-bottom ask equipped with a
mechanical stirrer, a thermometer and a condenser was charged with
water (187 g), sodium dodecyl benzene sulfonate (0.8 g), CaO( 1.9 g)
and NaOH (3.7 g) to 70 1C. Soy our (80 g) was then charged to the
rapidly stirring solution. The mixture was heated to 90 1C over
15 min, with rapid agitation, and held between 88 1C and 92 1C for
3 h. The mixture was cooled to 35 1C in an ice bath. The solid content
of the resulting soy-based adhesive was 3071%.
2.3. Preparation of melamineformaldehyde (MF) resin
Formaldehyde 37% (150 g), melamine (80 g) and water (107 g)
were charged into a three-neck ask equipped with a mechanical
stirrer, thermometer and condenser and then the pH was adjusted
to 9.0 with NaOH 30%. The mixture was heated to 85 1C during
2030 min, and held the temperature for another 30 min. The
mixture was cooled to room temperature and kept at pH 9.0 and
room temperature.
2.4. Preparation of plywood samples bonded with soy-based
adhesive
The soy-based adhesive was mixed well with different cross-
linkers just before the preparation of three-layer plywood of
dimensions 300 mm220 mm4 mm. The double sides glue
loading was 360 g/m
2
. Before sending into the press, the veneers
with adhesives were allowed to rest at room temperature for
15 min and were then assembled. The plywood was pressed under
pressure of 2 MPa at 160 1C for 8 min. Other press times and press
temperatures were also used in this paper.
2.5. Test of dry and wet shear strength of plywood samples
After conditioning in the laboratory for 1 day, the plywood panel
was then cut into shear specimens with dimension of 100 mm
25 mm to determine its shear strength and water resistance. Each
specimen has a bonded area of 25 mm25 mm. Both dry and wet
shear strength of plywood specimens were tested on a WDS-50KN
mechanical testing machine. For wet shear strength, the specimens
were soaked in (6373) 1C water or in boiling water for determined
time. The mean result of 810 specimens was considered as the nal
shear strength. The testing method was referred to Chinese national
standard GB/T 9846.3-2004. In this standard, for type II plywood, the
specimens were soaked in (6373)1C water for 3 h. For type I plywood,
the specimens should pass waterdrywater cycle. That is to say, the
specimens were rstly soaked in boiling water for 4 h, then dried in
(6373) 1C for 20 h, and lastly re-applied in boiling water for another
4 h. For both type II and type I plywood, before the measuring by the
testing machine, the specimens were taken out of water and left at
room temperature for 10 min.
2.6. FT-IR analysis
The oven was preheated to 160 1C. Liquid soy adhesives with or
without cross-linkers were put in the oven to a constant weight.
The cured soy adhesives were ground into ne powder. 1 g KBr
and 0.001 g soy adhesive samples were mixed well for the
preparation of KBr pills. The FT-IR spectra were obtained on a
Varian 1000 infrared spectrophotometer.
3. Results and discussion
3.1. Effect of cross-linker on performance of soy adhesive-based
plywood
Table 1 shows the performance of plywood specimens with soy
based-adhesive with or without different amounts of cross-linkers.
The cross-linkers used in this work included EPR, MF and their
mixture. The dry shear strength for all of the soy-based plywood
specimens was good enough to satisfy the requirement of relative
Chinese national standard (GB/T 9846.3-2004, Z0.70 MPa). But
considering that wood failure for almost all of the specimens is
100%, which meant the measured dry strengths were mainly
determined by the strength of wood, it was difcult to see the effects
of cross-linker on the dry shear strength of plywood. However, the
water resistance of plywood specimens showed big differences with
or without cross-linkers. Soy adhesive without cross-linking had no
water resistance at all, which was indicated by the 100% delamination
of specimens when soaked in 63 1C water for 3 h. All of the three
cross-linkers in this work improved the water resistance of soy-based
adhesive more or less. When cross-linked with different amounts of
EPR, although the wet strength of plywood at 60 1C for 3 h could be
measured, it was not enough to meet the requirement of relative
standard. More than 50% of the specimens cross-linked by EPR failed
the soak test in 63 1C water for 3 h and 100% of the specimens
delaminated when the test condition became more severe as in
boiling water cycles. With the increase of the addition amount of EPR,
the percentage of number of specimens that failed in the soak test to
the total number of specimens decreased from 50% to 20%, which
indicated the improvement of the water resistance of soy-based
adhesive, although their water resistance was not enough to meet the
relative standard. Epoxy was assumed to improve the water resis-
tance of soy adhesive because of the reaction between epoxy groups
H. Lei et al. / International Journal of Adhesion & Adhesives 50 (2014) 199203 200
with high reactivity at the opposite ends of resin molecule and
reactive groups in soy protein. In this work, just epoxy was used as
itself without excess solvent or even curing agent being added. It is
wellknown that a curing agent is necessary for the curing of epoxy.
The most commonly used curing agent for epoxy is amine. Here, soy
protein could be regarded as the curing agent of epoxy. Once there is
some curing reaction between epoxy and protein, the water resistance
and mechanical performances of the nal soy-based system would be
improved with the increase of its molecular weight. Although EPR
could react with a wide variety of functional groups in soy protein,
high addition amount of EPR could not be used as an ideal cross-linker
for three reasons. (1) EPR is not soluble in water. Simple mixing of soy
our and an epoxy resin in water cannot generate a homogeneous
mixture. High addition amount EPR tended to aggregate in the
presence of water and got a poor cross-linking with soy. This was
the reason why the soy adhesive could not resist the boiling water
cycle test. (2) EPR will increase the viscosity of soy-based adhesive a
lot with a high addition amount, which will greatly affect the
application of the adhesive. (3) EPR is too expensive. It was unac-
ceptable to the industry when addition amount of EPR was higher
than 10% of the solid soy. Once the addition amount of EPR was higher
than 10%, the cost of EPR would be almost 30% of the soy powder.
MF is a widely-used adhesive with good water resistance in wood
industry. Soy adhesive cross-linked with water-soluble MF shows
better water resistance than that with the same amount of EPR, as
seen from Table 1. All of the specimens with MF passed the soak test
at 63 1C for 3 h. No specimen delaminated and the wet strength for
all the specimens was higher than the standard requirement
0.70 MPa. This meant that interior type II plywood could be prepared
with soy adhesive cross-linked with as low as 6% of MF on solid soy
adhesive. But when the test conditions were changed to those of
boiling water cycle, although most of the specimens did not
delaminate, the wet shear strength decreased greatly. Even when
the addition amount of MF increased to 14% of solid soy, the wet
shear strength could not satisfy the relative standard. This meant that
only with MF, the hydrophilic groups in soy adhesive of this paper
could not be totally hidden or reacted with hydrophobic groups. For
wet shear strength in 63 1C water and in boiling water, the effects of
addition amount of MF on wet strength were not clear.
To make use of the high reactivity of EPR and the water
solubility of MF, a hybrid cross-linker EPRMF was used in this
work. As seen from Table 1, the hybrid cross-linker MFEPR
indeed showed the best water resistance. With 10% EPRMF, even
type I plywood could be prepared.
3.2. Effect of hybrid cross-linker EPRMF on the performance
of soy adhesive -based plywood
Hybrid cross-linker EPRMF was proved to be the best cross-
linker for soy-based adhesive as seen from Table 1. To optimize the
proportion of components of hybrid cross-linker and decrease the
addition amount of soy adhesive for plywood, in the hybrid cross-
linker, different amounts of EPR and MF were used for preparation
of plywood (Table 2). As in Table 1, when using hybrid EPRMF as
a cross-linker of soy adhesive, all of the dry shear strength of
plywood specimens cross-linked with different amounts of
EPRMF satised the requirements of the relative standard. In
the soak test, either in 63 1C water for 3 h or in boiling water cycle,
no specimen delaminated. It indicated that soy-based adhesive
cross-linked with EPRMF had good water resistance even with a
very low addition amount of cross-linker, that is, 3.2% EPR and
2.6% MF on solid soy adhesive. In laboratory condition, during the
preparation of plywood, lower addition amount of cross-linker
than 3.2% EPR or 2.6% MF was difcult to handle because of the
Table 1
Effect of different kinds of cross-linker on the performance of soy adhesive-based plywood.
Cross-linker Addition amount
of cross-linker (%)
Dry shear
strength(MPa)
63 1C 100 1C
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
Without cross-linker 0 1.02 100
EPR 6 0.85 0.41 50 100
8 0.80 0.38 50 100
10 0.86 0.39 30 100
12 0.77 0.48 20 100
14 0.85 0.46 20 100
MF 6 0.80 1.03 0 0.47 40
8 1.06 0.80 0 0.51 30
10 0.88 0.94 0 0.51 20
12 0.86 0.92 0 0.52 10
14 1.32 0.94 0 0.52 20
EPRMF 10(55)
n
1.05 0.91 0 0.85 100
n
The weight ratio of solid EPR to MF on the solid weight of soy adhesive was 1:1.
Table 2
Effect of addition amount of cross-linker EPRMF on the performance of soy adhesive-based plywood.
Cross-linker Dry shear
strength (MPa)
63 1C 100 1C
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
3.2%EPR2.6%MF 0.96 0.49 0 0.45 0
3.2%EPR3.9%MF 1.02 0.44 0 0.49 0
3.2%EPR5.1%MF 1.01 0.73 0 0.65 0
3.2%EPR6.4%MF 1.21 0.72 0 0.65 0
6.4%EPR6.4%MF 0.95 1.08 0 0.81 0
6.4%EPR7.7%MF 0.93 0.76 0 0.93 0
H. Lei et al. / International Journal of Adhesion & Adhesives 50 (2014) 199203 201
small amount. When the addition amount of EPR was xed to 3.2%
on solid soy adhesive, with the increase of the addition amount of
MF, the wet shear strength of plywood increased. However, at least
5.1% MF should be used together with 3.2% EPR to get the modied
soy-based adhesive for the preparation of type II plywood. For
type I plywood, the minimum addition amount of cross-linker of
soy based-adhesive was 6.4% MF with 6.4% EPR in Table 2.
Considering the results of Table 1, the total amount of hybrid
cross-linker MFEPR should be 1012.8% for preparation of type I
plywood. The increase of wet shear strength caused by the
increase of addition amount of EPR could also be seen in Table 2.
3.3. Effect of press procedure on the performance of soy-based
adhesive with hybrid cross-linker EPRMF
Soy adhesives with 6.4%EPR6.4%MF were used for the pre-
paration of plywood in the laboratory. Effects of press temperature
and press time on the performance of plywood with soy-based
adhesive are shown in Table 3. The results show that even with
press temperature 120 1C, type II plywood could be obtained. With
press temperature 140 1C, the water resistance of plywood was
good enough to meet the requirement of type I plywood and did
not show much difference with those when higher temperatures
160 1C and 180 1C were used.
26 min at 160 1C was too short to cure soy adhesive with
EPRMF, which indicated by the poor water resistance shown in
Table 3. With 46 min, the dry shear strength of plywood was
good. This meant that 46 min was enough for curing of soy
adhesive but not enough for its cross-linking. Hot-press time as
long as 8 min may be a problem for the commercialization of the
cross-linked soy adhesive.
3.4. FT-IR analysis of soy adhesive modied with cross-linkers
The FTIR spectra of cured soy-based adhesive, soy6.4% EPR,
soy6.4%MF and soy6.4% EPR6.4%MF are given in Fig. 1. For soy
adhesive without cross-linkers, the broad band observed in the range
of 35003000 cm
1
was assigned to the free and bound OH and N
H groups. The absorption bands of amide, the characteristic group of
protein, were observed at 1654, 1539, and 1238 cm
1
, which were
assigned to CQO stretching, NH bending, CN stretching and NH
bending vibration, respectively. The COO and CNH
2
absorptions
were seen at 1390 and 1058 cm
1
, respectively. The main difference
between spectra of soy adhesive with or without EPR came from the
absorptions at 1249 and 833 cm
1
, which were assigned to COC
stretching. There were three possibilities for the COC stretching:
(1) epoxy ether; (2) phenolOC; and (3) the resulting ether from the
reaction between epoxy and OH of soy protein [18]. The former two
groups came from EPR itself. The reaction between EPR and OH of
soy protein might be the main reason for the improvement of water
resistance of soy-based adhesives caused by epoxy. However, the
possible reaction between EPR and NH
2
, SH, COOH groups of soy
is not clearly observed in Fig. 1. In soy adhesive cross-linked with MF,
the absorption at 1238 cm
1
got weaker than that in pure soy
adhesive, which might be a result of the reaction between methylol
group of MF resin and NH groups of soy adhesive [11]. The increase
of the absorption at 1539 cm
1
was caused by CQN ring vibration
of melamine. Bending vibration of triazine ring was found at
829 cm
1
.The spectra of soy cross-linked with EPR and MF were
almost the multiplicity of soy adhesive cross-linked by EPR or MF
alone. Although a thorough mechanism on the soy-based mixing
system is still needed, the fact that epoxy and MF could react with
different groups in soy protein might be the main reason for the good
water resistance of soy-based adhesive with hybrid cross-linker. On
one hand, the mixing of epoxy and MF transferred the hydrophilic
groups of soy protein to hydrophobic ones as much as possible.
On the other hand, the epoxy was used as less as possible to avoid
aggregation and the large increase of viscosity.
4. Conclusions
To develop a soy-based adhesive with good water resistance
and acceptable cost, it was modied with cross-linkers, namely,
EPR, MF and their mixture EPRMF in this paper. All the three
Table 3
Effect of press procedure on the performance of soy adhesive-based plywood.
Press variable Dry shear
strength (MPa)
63 1C 100 1C
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
Wet shear
strength (MPa)
Number of specimens failed
in the soak test/total specimens (%)
Press temperature (1C)
120 1.12 0.84 0 0.61 0
140 0.94 1.03 0 0.83 0
160 0.95 1.08 0 0.81 0
180 0.85 1.12 0 0.76 0
Press time (min)
2 0.45 100 100
4 0.83 100 100
6 0.89 100 100
8 0.95 1.08 0 0.81 0
4000 3500 3000 2500 2000 1500 1000 500
Wave numbers/cm
-1
Fig. 1. FT-IR of the soy adhesive with or without cross-linker: (a) soy adhesive;
(b) soy6.4%EPR; (c) soy6.4%MF; and (d) soy6.4%EPR6.4%MF.
H. Lei et al. / International Journal of Adhesion & Adhesives 50 (2014) 199203 202
cross-linkers improved the water resistance of soy-based adhesive
more or less. The soy-based adhesive cross-linked with hybrid
cross-linker EPRMF showed the best water resistance. With
press temperature 160 1C and press time 8 min, type II and even
type I plywood could be prepared when 6.4%EPR6.4%MF was
used as the cross-linker of soy-based adhesive. FT-IR indicated that
the great improvement of water resistance of soy-based adhesive
modied with EPR and MF might be caused by the reaction
between epoxy and OH, and that between MF and NH.
Acknowledgments
This research was supported by the National Natural Science
Foundation of China (31170530) and New Century Excellent
Talents of Ministry of Education of China (NCET-10-0972).
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