4

Melamine–Formaldehyde Resin

4.1 Introduction
Melamine-based resins belong to the class of aminoplastic resins and are
made by the reaction of formaldehyde either with mainly melamine, or
employing urea, phenol, or other components as co-monomers. Melamine
adhesives are predominantly used as adhesives for wood panel products
such as particleboards, medium-density fiberboard (MDF), oriented
strand board (OSB), plywood, blockboards, and others. Melamine-based
adhesives are also used for the production of paper laminates. In rare cases,
the resins and panels are also used in the furniture industry.
For most applications as wood adhesives, melamine resins are in liquid
form. For special applications, powdered (spray dried) types are used. The
resins consist of linear or branched oligomeric and polymeric molecules
in an aqueous solution, and sometimes partly as a dispersion of molecules
in an aqueous phase. The resins show a thermosetting behavior, leading to
three-dimensional hardened networks.

4.2 Chemistry
Melamine is a 1,3,5-amino substituted triazine derivative, industrially pre-
pared by cyclic condensation of three urea molecules and possessing the
following structure:

NH2

C
N N
H2N C C NH2
N
Melamine

R. N. Kumar and A Pizzi. Adhesives for Wood and Lignocellulosic Materials, (101–113) © 2019
Scrivener Publishing LLC

101
102 Adhesives for Wood and Lignocellulosic Materials

The reaction between melamine and formaldehyde is similar to that of

urea.
As can be noticed in the above structure, the melamine molecule con-
tains three primary amine groups, each of which has the potential of react-
ing with two moles of formaldehyde forming up to a hexa-substituted
product if the molar ratio F/M is high enough. Because of the significantly
higher reactivity than urea of the amino groups of melamine towards sub-
stitution with formaldehyde, the melamine resins show the ability to form
polymer structures with a much higher cross-link density compared to UF
resins [1].

4.2.1 Formation of Methylolmelamine

Under slightly alkaline conditions, melamine reacts with formaldehyde to
form methylol derivatives with up to six methylol groups per molecule.
Initial reaction between the monomers (usually at temperatures in excess
of 80°C, in aqueous solution, and a slightly alkaline environment) gives
methylolmelamines. With M:F ratios of 1:2 to 1:3, dimethylolmelamine is
formed. Decreasing the M:F ratio to 1:8 will give hexamethylolmelamines,
in which all of the NH2 groups are converted to methylol. These are often
used as cross-linkers in reactions with other resins, like acrylates or polyes-
ters. The methylol derivatives so formed can be presented by the following
structures:

NH2 NH2

C 2 CH2O C
N N N N
H2N C C NH2 HOCH2-HN CC NH-CH2OH
N N
Melamine Dimethylol melamine

Similarly, depending on the ratio of formaldehyde to melamine,

trimethylolmelamine and up to hexamethylolmelamine are formed:

HO-CH2 CH2OH
N
NH-CH2OH
C
C HO-CH2 N N CH2OH
N N N
N C C
HOCH2-HN C C NH-CH2OH HO-CH2
N CH2OH
N
Trimethylol melamine Hexamethylol melamine
 Melamine–Formaldehyde Resin 103

NH2 NH2

C C
N N N N
H 2N C C OH HO C C OH
N N
Ammeline Ammelide

OH

C
N N
HO C C OH
N
Cyanuric acid

Figure 4.1 Ammeline, ammelide, and cyanuric acid.

Pure MF resins are usually prepared by the reaction of melamine with

formaldehyde in an aqueous solution, yielding a precondensate consisting
of a mixture of different monomeric as well as short linear and branched
oligomeric species. These reactions are controlled by the following param-
eters: temperature, duration of condensation, pH, as well as the order and
time course of heating and reagent addition. Usually, all types of methylo-
lated melamine species together with oligomeric parts (usually more than
six melamine residues are linked from the beginning of the reaction) are
present in the reaction mixture [2].
At the condensation stage, attention must be paid to the formation
of hydrolysis products of the melamine before preparation starts. The
hydrolysis products of melamine are obtained when the amino groups of
melamine are gradually replaced by hydroxyl groups. Complete hydrolysis
produces cyanuric acid (Figure 4.1) [1].
Ammeline and ammelide can be regarded as partial amides of cyanuric
acid. They are acid and have no use in resin production. They are very
undesirable by-products of the manufacture of melamine because of their
catalytic effect in the subsequent MF resin production, due to their acidic
nature. If present, both must be removed from crude melamine by an alkali
wash and/or crystallization of the crude melamine [1].

4.2.2 Condensation of Methylolmelamines

On heating, methylolmelamines condense to form resinous products,
which become increasingly hydrophobic until eventually a gel is formed.
104 Adhesives for Wood and Lignocellulosic Materials

The rate of resinification is strongly dependent on pH. An increase or

decrease from the pH level of 10 to 10.5 of liquid resin stability results in
considerable increase in the reaction rate. The chain extension occurring
during condensation can be represented as follows:

(a) Methylol-amine condensation methylene link is formed

R-NH-CH2OH + H2N-R R-NH-CH2-NH-R + H2O

(b) Condensation between two methylol groups Ether linkage is formed

R-NH-CH2OH + HO-CH2-NH-R R-NH-CH2-O-CH2-NH-R + H2O

(c) Condensation between methylol group and imino hydrogen

R-NH-CH2
R-NH-CH2OH + HO-CH2-NH-R
R-N-CH2OH + H2O

(d) Ether link is broken with evolution of CH2O and water and formation of mehylene

R-NH-CH2OH + HO-CH2-NH-R' R-NH-CH2-NH-R + H2O + CH2O

4.2.3 Cross-Linking
Conversion of liquid melamine–formaldehyde resin to a solid network
takes place by heating. The rate of cross-linking can be increased by the
addition of an acid or a salt, but for several applications, the rate of cure is
adequate without the addition of acids. Resin curing proceeds through the
participation of methylol groups and amino hydrogen in the same manner
as shown in Section 4.2.2 above. A simplified schematic structure of the
cured melamine formaldehyde resin is given below: The structure empha-
sizes the importance that there are many ether bridges besides unreacted
methylol groups and methylene bridges [1, 3]. This is because in curing
MF resins at temperatures up to 100°C, no substantial amounts of formal-
dehyde are liberated. Only small quantities are liberated during curing up
to 150°C. However, UF resins curing under the same conditions liberate a
great deal of formaldehyde.
 Melamine–Formaldehyde Resin 105

N N N
C C NH CH2 NH C C NH CH2 CH2 NH C C NH
N N N N N N
C C C

NH NH NH

CH2 CH2

O O

CH2 CH2

N CH2OH NH

C C
N N N N
N
C C NH CH2 NH C C NH CH2 O CH2 NH C C NH
N N
N N
C

NH CH2OH

CH2

NH

C
N N
NH C C
N

4.3 Melamine–Urea–Formaldehyde (MUF) Resin

MUF resins are widely used in the wood working industry as adhesives
for the production of wood-based panels, namely, particleboard, ply-
wood, and various fiber boards. These resins are the products of the reac-
tion of urea and melamine with formaldehyde. The resin is set or cured
with a hardener such as ammonium salts or acids. A urea–formaldehyde
resin with a high melamine content is described in reference [4]. The
resin contained 9.5% to 34.4% melamine by weight. The resin had a shelf
life of less than 1 day [4]. Usable formulations are also disclosed in the
scientific literature [1, 5].
US Patents 4,536,245, 5,162,462, 4,603,191, and 5,008,365 have dis-
closed significant details of condensation of MUF resins [6–9].
106 Adhesives for Wood and Lignocellulosic Materials

US Patent 5,162,462 [7] describes a method for preparing aminoplast

resin based on 2-ureido-4,6-diaminotriazine-1,3,5. The resulting resin is
reported to have very low formaldehyde emission.

NH-C-NH2

C
N N
H2N C C NH2
N
2-ureido-4,6-diaminotriazine 1,3,5

2-ureido-4,6-diaminotriazine-1,3,5 is prepared by reacting melamine

and urea in all molar ratios in dimethyl formamide, the reaction being
maintained at reflux temperature for at least 6 h and washing the resulting
solution with an alkaline solution.
US Patent No. 5,681,917 discloses a method for preparing a MUF resin
of low formaldehyde content [10]. The resin has a formaldehyde-to-urea
ratio of 0.5:1 to 1.1:1.
US Patent 6,723,825 B2 relates to a liquid MUF resin that is stable for
a period of up to 4 weeks [11]. The relevant details have been discosed in
this patent.

4.3.1 Liquid MUF Resin Preparation

The resin is prepared by taking 955 g of non-methanol-stabilized formalin
of concentration 44% in a reaction vessel. The pH is adjusted to 8.0 to 8.5
using 1.1 g of 20% sodium hydroxide solution. The contents were heated to
50°C and after about 30 min, 423 g of urea was added. The temperature was
raised to 90°C and held for 15 min. The contents were cooled to 85°C and
pH was reduced to 4.9 to 5.1 using about 1.1 g of 10% formic acid. The
viscosity was monitored using a Brookfield cone plate viscometer at 25°C
using spindle # 42 and a shear rate of 10 rpm with 1-ml samples. Once the
viscosity reached 200 to 280 cps, the kettle was cooled to 60°C and the pH
increased to 8.4 to 8.8 with about 0.75 g of 20% sodium hydroxide solution.
A second formalin (610 g) was added to the mixture, and the pH was
adjusted to 8.5 to 8.8 with about 1.1 g of 20% sodium hydroxide solution.
Melamine (567 g) was then added, followed by 60 g of methanol. The pH
was then increased to 9.8 to 10.2 with about 1.1 g of 20% sodium hydroxide
solution. The mixture was then heated to 85°C and the 25°C hydrophobic
test was conducted. The hydrophobic test was performed by removing a
 Melamine–Formaldehyde Resin 107

25-g sample of resin from the mixture and titrating the resin with distilled
water at 25°C to a hydrophobic cloudy end point. The volume of distilled
water is measured and the test repeated until the range is 22 to 25 ml/25 g
of the resin. The hydrophobic test provides an indication that the desired
viscosity has almost been reached. Once the hydrophobic end point was
reached, the viscosity of the mixture was monitored until it reached a
value of 200 to 280 cps. The mixture was then cooled to 25°C, the pH was
adjusted to 9.2 to 9.5 with about 0.35 g of 20% sodium hydroxide solution,
and the resin was filtered.

4.3.2 Phenol–MUF (PMUF) Resins

Most wood adhesives used for the production of wood panel products at
present are based on urea–formaldehyde resins that do not have acceptable
weatherability. Although melamine resins are increasingly used to meet
higher requirements for bond strength and moisture resistance, they were
thought to be not completely suitable for preparing weatherproof adhe-
sive joints. Weatherproof wood joints have been produced in the past
only with phenolic resins capable of alkaline cure; however, such joints
are dark in color. Thus, although nowadays really weatherproof melamine
and melamine–urea resins have been developed, there remains a feeling
in the industry for a commercial need for adhesive resins that are clear,
homogeneous, miscible with water, of low viscosity, suitable for easy and
even spraying or blending with wood composites, and stable, and that have
acceptable storage stability and a fast curing rate. They should be consistent
in quality from batch to batch, cure quickly and evenly, and meet the low
formaldehyde emission requirement. These properties are achieved by the
disclosure in European patent EP 0915141 B1 on PMUF resins prepared
by condensing phenol, formaldehyde, melamine, and urea in the sequence
set forth in the patent [12]. Unfortunately, for this type of PMUF adhesives,
resin engineering has progressed so much for MUF resins, which are eas-
ier to produce, to render much less attractive the preparation and use of
PMUF resins [1, 13].
According to PMUF preparation European Patent EP 0915141 B1, it
is imperative to condense formaldehyde with phenol and then condense
melamine with the phenol–formaldehyde condensate before introducing
urea [12]. If this condensing sequence is not observed, a resin will not be
obtained, which can be used to make adhesives with weatherproof quality.
The details of the process are disclosed in the above patent.
In preparing the condensate, formaldehyde and phenol are added to a
reaction vessel and thoroughly mixed. This will take the reaction between
108 Adhesives for Wood and Lignocellulosic Materials

phenol and formaldehyde to the methylolation state. Sufficient triethanol-

amine is added to raise the pH to 5.6–6.4, preferably 5.8–6.2, and then, with
caustic soda, the pH is increased to 8.5–9.5, preferably about 9.0. Cooling
of the reactor contents is commenced and when a temperature of 40°C or
below is reached, melamine is added with vigorous agitation to ensure that
all of the melamine is wetted.
At this point, the contents of the reactor are heated to 85°–100°C, pref-
erably 93°–95°C, and held at this temperature for 10–45 min, preferably
about 20 min. Condensation of the melamine is considered complete when
the solution becomes clear.
This is followed by the addition of the first portion of urea over a period
of 5–20 min, preferably 7–13 min, while holding the temperature at about
93°–95°C to obtain a polymer of desired chain length. After all of the urea
solubilizes, the reaction is held at 80°–100°C, preferably 87°–89°C, until a
water tolerance of 70–180%, preferably 100–150%, is reached.
The contents of the reactor at this stage are cooled to 45°–50°C and an
additional 0.2–1 mol of urea, preferably 0.65–0.75 mol, is added to react
with excess formaldehyde, with continued cooling to about 25°C. Lastly,
the pH is adjusted with triethanolamine to 7.5–8.5, preferably 8.0–8.4.
Frequently, in these resins, the phenol is not completely reacted. Thus,
the PMUF resin will be a poorer resin than just an equivalent MUF resin.
Reaction of the phenol with the MUF part depends exclusively on the con-
ditions under which the reaction is carried out. If the phenol addition is
done under the incorrect conditions, which is often the case, the phenol
may remain often unutilized and does not contribute to the final resin net-
work [1, 13].
It is then necessary to define the order how the reagents are added to
ensure that the phenol also participate to the strength and characteristics
of the hardened network [1, 13]. Good PMUF resins are produced today
by very reputable companies, but they do not appear to be better than
MUF resins where the phenol has been substituted mole by mole by just
melamine.

4.3.3 Melamine–Formaldehyde Resin Modification

by Acetoguanamine for Post-Formable High-Pressure
Laminate
Compared to the laminates of the usual commercial quality, post-moldable
laminates have the property of being still moldable after heating up. Using
such moldable sheets, it is possible to manufacture furniture compo-
nents with decorative melamine resin surfaces with rounded edges. Main
 Melamine–Formaldehyde Resin 109

applications are for kitchen furniture. The advantages of such sheets are
obvious. By having seamless cover of the edges, penetration of water is
prevented. Several methods were used, e.g., during the hot pressing, the
resin does not cure completely. These sub-cured sheets could be post-
molded well. However, during storage, post-curing takes place and there-
fore the post-moldability is negatively affected or even lost. Unsuccessful
attempts were made to produce suitable resins by addition of plasticiz-
ers that will not react with formaldehyde or the methylol groups of the
melamine resin, e.g., PVC, polyacrylonitrile, and polyvinyl acetate. These,
called external plasticizers, have the defect to migrate to the surface, caus-
ing several technical problems. Subsequently, internal plasticizers, thus
plasticizers reacting and being co-condensed within the resin, were tried.
These modifying agents are built into the structures of the melamine
resin molecule. Acetoguanamine belongs to this category and is the most
effective for this purpose, but also others are sometimes used such as
ε-caprolactam.
CH3

N N

H2N N NH2

Acetoguanamine

Kuchler et al. [14] found that acetoguanamine is particularly suitable

as the modifying agent for melamine formaldehyde resin to improve the
post-moldability of high-pressure laminates made therefrom. Another
modifying agent used in this study was diethylene glycol or digly-
col. Seeholzer reported that acetoguanamine improved the elasticity of
melamine resins [15]. By condensing acetoguanamine together with
melamine resin, the resin remains plastic and formable over prolonged
periods of time. Seeholzer further found that diethylene glycol had a syn-
ergistic effect with the acetoguanamine and reduced cured cracking [15].
Paper laminates impregnated by melamine-based resins can today be
prepared in two different ways [1]: (1) either by double impregnating bath
machines in which the paper passes first in a cheaper UF resin solution
and then in a second bath of a more expensive MF resin, thus producing a
paper core impregnated of UF resin and surfaced with MF resin; (2) or in
single bath machines where either a traditional MF resin is impregnated,
110 Adhesives for Wood and Lignocellulosic Materials

this being more expensive, or a cheaper MUF resin of a relatively high

level of melamine. Both approaches are aimed to decrease the proportion
of expensive melamine without altering the impregnated paper approach.

4.3.4 MUF Adhesive Resins of Upgraded Performance

Decreasing the proportion of melamine in MUF resins at equal perfor-
mance has been a recent trend. This can be done by a number of different
approaches. These are as follows: (1) the use of melamine salts as additives
to UF resins, also performing, in this approach, the function of hardeners.
The proportion of melamine can then be decreased to 10% for an effect
normally obtained by 30% of melamine in the resin [16–19]. The mech-
anism by which addition of melamine salts to a UF adhesive is so much
more effective has been determined [16, 20]. Exposure to the weather of
panels prepared with this adhesive approach has confirmed the laboratory
results concerning the performance of these panel adhesives [18, 21].
(2) The progress in melamine and urea adhesive formulations has
caused that the postulate that degradation induced in the curing of these
resins by an excessively long panel press time at high temperature occurs
during board manufacture is no longer valid. The lower resin molar ratios
used today to counterbalance and decrease formaldehyde emission has led
to much slower curing resins, thus rendering questionable the industrial
practice of rapidly cooling the panels once out of the hot press to avoid the
degradation of the adhesive hardened network [22, 23]. This is so, as the
adhesives holding the boards together are not completely cured once com-
ing out of the hot press, with an estimate of around 70% only of possible
maximum cure. This means that while some cooling is still necessary once
the panels come out of the hot press, this can be reduced to just maintain
the panels at a hotter temperature than what is done in the past and thus
obtain a better strength at a shorter press time. Models defining the more
apt post-curing strategies have been determined [22].
(3) The sequence of manufacture of these MUF resins determines that
the chemical species produced are very different, and at minimum, their
relative proportions are also very different, causing also marked differences
in the cross-linked network induced by their hardening. For example, one
can prepare MUF resins according to the classical, traditional, sequential
addition of reagents, but also MUF resins according to nontraditional,
nonsequential formulation approaches. These two approaches have been
shown to produce very different resins [24]. Nonsequential MUF resin
formulations have only relatively recently been started to be investigated
for their potential in markedly decreasing the proportion of the expensive
 Melamine–Formaldehyde Resin 111

melamine while maintaining resin performance. Such approaches are

based on additives having special effects. The main additives, used in 1% to
5% on resin solids, for this approach are the so-called acid anion-stabilized
iminomethylene basis [25–28] that can be prepared in a couple of different
ways such as reacting formaldehyde and ammonia [25–28] or by stabiliz-
ing the decomposition of hexamine to prepare the so-called “hexamine
sulfate” [29]. These approaches do achieve marked decreases in melamine
content at equal resin performance. For example, the strong effect on MUF
adhesives of the so-called “hexamine sulfate” was found to be due to the
strong buffering and stabilizing effect induced by the additive during adhe-
sive curing [26–28].

4.3.5 Cold-Setting MUF Adhesives

MUF cold-setting wood adhesives for glulam and fingerjointing are also
used especially in Europe. They are considered for use as protected exterior
structural applications and their clear bondline renders them particularly
acceptable from a visual, aesthetic point of view. The positive evolution
in their formulation and the forever-improving performance render them
today comparable to classical PRF adhesives [30], these latter being still
preferred in North America while the former are preferred in Europe.

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Wiley & Sons, New York, 1965.
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 Melamine–Formaldehyde Resin 113

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