Industrial Crops and Products, 1 (1993) 89-99 89

0 1993 Elsevier Science PublishersB.V. All rights reserved.0926~6690/93/$05.00

INDCRO PRO44

Utilization of vegetable oils in coatings

Horst Hintze-Brtining
BASF La&e und Farben AG, Miinster, Germany

(Accepted 8 June 19921

Abstract

Hintze-Brtining, H. 1993. Utilization of vegetable oils in coatings. Industr. Crops Products 1: 89-99.

Vegetable oils are common raw materials in the coating industry, especially for alkyd resins. These
are in common use, but in many industrial coating systems they became second choice because of
substitutes based on petrochemical raw materials and which provide an improved technological perform-
ance. In architectural coating systems alkyd resins still play an important role because of their benefits
such as the economical balance, an uncomplicated application and an outstanding appearance of the
films. Water-borne and high solids systems as well as alkyd/acrylic-hybrids will increase their market
share for ecological reasons. Apart from alkyd resins, oils are used as reactive diluents e.g. in printing
inks, and fatty acids are used as educts for a series of specialty products in the coating industry, e.g.,
electric insulation systems.

Vegetable oil; Fatty acid; Alkyd; Resin; High solid; Water reducible; Airdrying; Ageing; Coating

Introduction “oriental lacquer” - an aqueous high solids

Recently the use of renewable raw materials in
the chemical industry has attracted increasing
attention (Gedam and Sampathkumaran,
1986; Gilkes, 1968; Princen, 1977, 1979) as a
result of growing ecological problems, a short-
age of fossil reserves and economic difficulties
in agriculture. In the coating industry there
has been an inverse trend within the last four
decades. Historically, coatings have been
baaed on natural products such as shellac (me-
tabolism product of the shield-louse, Tuchar-
dia lacca) or the tree sap of Rhus vernicifera.
The latter has been the raw material for the
Correspondence:H. Hintze-Bribing, BASF Lacke und
Farben AG, Glasurit-Strasse 1, W-4460 Miinster, Ger-
many
coating which has been used in far eastern
cultures for more than 2000 years. The sap is
converted into a lacquer by fermentation and
conversion of an oil/water- into a waterloil-dis-
persion which results in films which are highly
resistant after application due to an ingenious
physicochemical curing mechanism (Kumano-
tani, 1988).
In Europe, the monk Theophilos reported in
1000 the fabrication of “Leime Vemition” -
obtained by polymerization of linseed oil in the
presence of amber. Together with the use of
minimum (= lead oxide) as pigment and drying
accelerator @a. 1000) and turpentine as
diluent (ca. 1000, islamic invasions) this inven-
tion was the basis for a European coating sys:
tern based on vegetable oils. Originally used for
 1000 tons / year 1000 tons / year
Total Proc &ion Systems
.-~--I eOo

I Powder Coatings

0 0
1976 1988 1989 1990

Source: Statistisches Bundesamt

Total amount: printing inks excluded
World total production (1976): 16.1 million tons

Fig. .. Production statistic for coatings sytems in Germany (former West Germany).

Resin (ALKYD)

Pigmen
dditlves (Thixotropic Agents)
(Thickeners)
(Emulsifiers)
Solvent (Anti Sagging Agents)
(Siccatives)
(Reactive Diluents)

Typical composition of a pigmented coating:

( ) = Components containing Oil / Fatty Acids

Fig. 2. Oiufatty acids as raw materials for coating components.

clerical book painting, it developed into a secu-
lar art by the influence of the “oriental lacquer
art” (brought to Europe by Vasco da Gama, ca.
1599) and reached its climax in 1773 when
Jean Felix Watin published his science of
“L’Art du peintre, doreur et vernisseur”.
The industrial application of coatings was
induced by the spreading of vehicle fabrication,
particularly coaches, around 1809 in England
and Holland. Synthetic resins have been
development since 1885. In 1930 alkyd resins
were introduced into the coating industry. This
type of resin is an oil- or fatty acid modified
polycondensation product of polyols and poly-
carboxylic acids. Due to their versatility, alkyd
resins may be regarded as a milestone in the
industrial application of coatings. Between 1939
and 1950 nearly ah the important synthetic resins
 x
HO
OH

HO OH
0
Pentaerythrltol Phthalic
Anhydride

OH
Pentaerythritol
fi OH
HO

Alkyd - Segment

Rl = Olelc Acid

Synthesisof alkydresinswithfattyacids(one stepreaction)or withtriglycerideas raw material(firststep:

Fia. 3.
tr&sestkrification;
secondstep:polycondensation).

such as ureas, acrylics, urethanes, melamines,
polyvinylics, unsaturated polyesters and epo-
xies were developed. The market share for
alkyd-based coatings in the 1990s has there-
fore diminished to ca. 20% (Fig. 1).
The composition of a typical (pigmented)
coating is shown in Figure 2. The main portion
is given by the resin, which is the film-forming
agent, followed by the pigment and the solvent.
The latter may consist of a drying oil (e.g. linseed
or soybean oil) as reactive diluent, e.g. printing
inks, In addition, oils and/or fatty acids are often
basic raw materials for emulsifiers and addi-
tives such as thixotropic agents, thickeners,
siccatives and others. The most important
parts of a coating are the resin and its solvent.
They determine whether the coating is water-
borne, whether it is air-drying at ambient or
higher temperatures, and whether it is applied
by brushing, rolling, spraying or with bars.
Alkyd Resins
Alkyd resins can be regarded as oil- or fatty
acid modified condensation polymers as well as
oils which are modified by means of polyols and
polycarboxylic acids. The latter view is more
striking because it reflects the historical evolu-
tion of alkyds which became efficient by the
improved industrial synthesis of phthalic an-
hydride (naphthalene oxidation with vana-
dium oxide catalysts, BASF 1916) and polyols
like pentaerythritole (acetaldehyde and forma-
ldehyde and their precursors ethanol and
methanol. Currently ca. 260 006 t/year penta-
erythritole worldwide, ca. 90% of US produc-
 n
H H Co<*Y+ar H 0’
+ o-5” - H o-d . n
+ .o’
heat
Diallylic Moiety Oxygen Hydroperoxlde Alkoxlradlcal Hvdroxlradlcal
of Fatty Acid

Conjugated Double Bounds

from lsomerlzed Fatty Acids

Fatty Acid Moletles Crossllnked H o

by an Allyllc Ether Group & . /

V\ H3c--o

“19’“’ Hydroxifunctlonal
Alkyd LJ
A A
n,c,o_J$po,C",
+ K"-ALKYD Acid Catalyst
?? 14,qo_JN~Oo,c”. + won 1

Heat Methanol
0) Lo 0) Lo
&f &I, &i, An,

Hexamethoxhnelsmlne Condensation Product

Fig. 4. Crosslinking of alkyd molecules by autoxidation (curing at ambient temperature) and by transetherification
with melamine resins (curing at elevated temperatures).

tion, is used as alkyd raw material (Indus-
trielle Organische Chemie, 1988). The chemis-
try of alkyd synthesis and an idealized struc-
ture of an alkyd chain segment is shown in
Figure 3. Oils are modified with polyols by
transesterification followed by polycondensa-
tion with phthalic anhydride. With fatty acids
polyesterification yields the alkyd in a one-step
synthesis. In practice, both routes may be com-
bined which extends the facilities to select from
a broad fatty .acid portfolio under economical
and technological aspects. The choice of fatty
acids and thereby the degree: of:olefinic unsat-
uration (expressed as Jodine value) as well as
the amount of fatty acid, used in the alkyd
synthesis (expressed as oil length = % triglyc-
eride) mainly determine the physical and
chemical features of the alkyd. This is il-
lustrated in Figure 5, which also shows the
most important composition area for coating
applications. Curing of the applied coating oc-
curs by crosslinking of alkyd-chains by air-dry-
ing (autoxidation of fatty acid moieties (Han-
cock and Leeves, 1989a-c; Marshall et al.,
1987; Vaes, 1988)) and/or by reactions of re-
sidual OH-groups with crosslinkers, e.g.
melamines (Fig. 4). The latter mechanism is
restricted to forced drying conditions (80-
200°C) and can be combined with the autoxida-
tion by an appropriate choice of fatty acids. The
most important fatty acids and their sources
are listed in Table 1. For high air-drying rates
linoleic acid in combination with conjugated
linoleic unsaturation is preferred. Linolenic
acid and eleostearic acid, which are known to
exhibit excellent autoxidation rates, suffer
from other disadvantages which will be dis-
cussed later.
 93

Jodine Value [mg J2 I g]

dryiWbY *w ~____________ -.-
autoxidation i,
A

common range

physical
drying
% oil incorporated in a
polyester backbone

Fig. 5. Common range of alkyd features determining the physical (weight % triglyceride) and chemical (Jodine value)
properties of the coating.

TABLE 1

Common fatty acids used in coating materials

Fatty acid Main source (oil) Structural features Susceptibility to Main field of application

Saturated (C12-Cl@ Palm/coconut stoving lacquers

elastomers
Oleic acid Soybean/tall stoving lacquers
sunflower/satIlower
9,12-Linoleic acid Soybean&all one activated allylic autoxidation airdrying lacquers
sunflower/safflower group
Linolenic acid Linseed two activated allylic autoxidation airdrying lacquers
groups printing inks
9,11-Linoleic acid 9,lZLinoleic acid two conjugated polymerization airdrying lacquers
dehydrated castor oil C=C-bonds stoving lacquers
Eleostearic acid Tung three conjugated polymerization airdrying lacquers
C-C-bonds
Ricinoleic acid Castor hydroxifunctional dehydration stoving lacquers
pigment grinding
Arachidonic acid Fish highly unsaturated autoxidation airdrying lacquers
Clupanodonic acid C2OlC22

The universal use of alkyds is also proven by
a broad compatibility with other resins and by
the possibilities to modify the OH- and the
olefinic functionality, e.g. styrenated or
urethane-alkyds (Earhart, 1969, Moustafa et
al., 1987; Schneider et al., 1970; Seymour et al.,
1990). However there are some drawbacks of
alkyd-based coatings which are related to in-
herent qualities of the fatty acid unsaturation.
The autoxidation is a rather slow curing mech-
 Fl Glass Transition Temperature
Autoxidation
25 -
0 I
0 5
Acrylic Dispersion
__.__..__.._Alkyd Coating
Fig. 6. Comparison of the ageing of cured films based on alkyd resins (post-curing) and on acrylic dispersions (erosion).
anism compared with other crosslinking reac-
tions, e.g. the 2 K urethane formation. In-
dustrial coating systems which have to be
cured at ambient temperatures must fit the
production cycles to ensure profitability (e.g.
window frame production, car refinishing).
Fast drying systems (2 K isocyanate/polyol-re-
action; acrylic dispersions: fast physical dry-
ing) have increasingly displaced alkyds. Coat-
ing systems which are cured by stoving, e.g.
vehicle OEM coatings, have been the subject of
increasing demands concerning the durability
of the cured films: weatherability, UV-re-
sistance. The lifetime of an alkyd-based film is
restricted by the residual olefinic unsaturation
which leads to further crosslinking. This re-
sults in an increasing brittleness of the film
(increasing glass transition temperature)
which promotes crack formation and delami-
nation of the film. In Figure 6 this is shown
compared with a film based on an acrylic dis-
persion (Holsworth et al.; Newton, 1986;
Schmid, 1987, 1988, 1990). In non-industrial
applications (painters, do-it-yourself) other au-
toxidation byproducts adversely affect the ac-
ceptance of alkyd coatings. These are alde-
hydes which are formed by oxidation of the
olefinic bounds and which are responsible for
the strong smell of cured films and for the
yellowing of white films in the dark (Henglein
I Mechanical Impact
1
I .
Lifetime wears]
and Fiiner, 1962; Link, 1986; Parmentier, 1988).
Environmental demands further oppress the
use of conventional alkyds (which are normally
diluted by 3040% mineral spirits or alkylaro-
matic solvents) in non-industrial applications.
Architectural Coatings
Despite the aforementioned drawbacks, some
alkyd-based coatings play an important role in
architectural applications. These are water-
borne and higher solids coatings (Ackerman,
1991; Chandra, 1990; Larson and Emmons,
1983; Kangas and Jones, 1987; Chen and
Jones, 1988).
High Solids Coatings
High solids coatings are defined as lacquers or
varnishes with an amount of less than 15% by
weight of volatile compounds (normally sol-
vents) (Mulvey and Dannemann, 1989; Ro-
lando, 1989;, High Solids Alkyds, 1987). Con-
ventional solvent-borne coatings normally
contain 30-60 wt % of volatile materials. The
technological challenge is to combine this
higher solids content with a viscosity which
allows brushability, a drying rate that is not
 95

100 Application Viscosity

0 20 40 60 60 100

Non Volatiles [%]

Fig. 7. Viscosity of an alkyd solution as a function of the molecular weight of the alkyd and of the solutions concentration.

, 6 Intensity (=Abundance)
I
14

12

10

6 -n Conventional
4
2

0
2 3 4 5 6 7

log Molecular Weight

Fig. 8. Molecular weight distribution curves for a conventional alkyd and a higher solids alkyds.

significantly slower than in conventional coat-
ings and an appearance of the cured film which
fits the conventional standard. The application
viscosity of ca. 160 mPa s depends on the solids
content and of the molecular weight of the
alkyd (Fig. 7). Therefore, higher solids coatings
can only be realized with alkyds of lower
molecular weights. This can be visualized by a
comparison of the molecular weight distribu-
tion of a higher solids versus a conventional
alkyd (Fig. 8). The higher solids alkyd has a
narrower distribution curve without the area
of higher molecular weights. Figure 9 also
shows two factors which rule the number of
structural units (correlating with the molecu-
lar weight) in a polycondensation polymer: the
degree of educt conversion and the diol/diacid
ratio (Flory, 1936, 1941; Jonason, 1960; Pat-
ton, 1966). Reduction of the educt conversion
would be detrimental to the coating perform-
ance. In consequence all known higher solids
alkyds are designed as molecules with a high
functionality in fatty acids to achieve a high
crosslink density per alkyd molecule. This is
96

Molecular Weight of Expressed by the Number of Structural Units

Number of Structural Units Number of Structural Units
25 25

20;. _.

,5___.
Dlol/Dlacld = 1
,*___

5_.__. _. _.

*I-/ ) ,I,,\1
0 02 0,4 0,6 0,8 1 1 1,l 1,21,91,41,51,61,71,81,9 2
(1 - AN/[COOH]) Dlol / Dlacld

AN = acldnumber of reaction mixture

[COOH] = Initial concentration of dlacld

Fig. 9. Number of structuralunits of an alkyd as a function of the polyol/diacidratio and of the degree of educt conversion.

+ Oiigomers With Higher Molecular Weight

Raw Trimeiiithic Acid High Functionaiity (F=ll)

ProvidesHigh CrceslinkDensii
Di-POntaOryUlritoiO
Low Yoiecuiar Weight
Pentaqthritoie ProvidesLowViiityandLowVCCContent

Fatty Acid (Rl)

Fig. 10. Possible (idealized) structure of a higher solids alkyd.

realized by high polyol/polyacid ratios and priate fatty acid composition is decisive for the
educts with high functionalities, e.g. dipen- performance of the higher solids coating, espe-
taerythritole (Fig. 10). The choice of the appro- cially the drying rate.

Maleated Linseed 011 for Watsrsoluble Resins
fi fCH&,-CO-GLYCEROL
dW +
Llnsaed 011Fatty Acid
200°C I ‘Ene’-Reactlon
I
0 O 0
v_
CH&TO-GLYCEROL
+ NH, -
W8tW
Fig. 11. Sunthetic approaches to water-reducible reins: (a) gl*afting of maleic anhydride on fatty acid unsaturation; (b)
formation of a chromane ring by addition of a resole to a fatty acid.
Water-reducible Alkyds
Aqueous architectural paints are dominated by
acrylic dispersions, but numerous approaches
for water-reducible alkyd coatings have been
described (Hohlein, 1987; Ziickert, 1986). Hy-
brids of acrylic dispersions and water-soluble
alkyds are also known to be advantageous for
wood sealings as they combine the alkyds’ ex-
cellent penetration behaviour with the fast
physical drying of the acrylic dispersion (Gooch
and Hofland, 1991).
Depending on the typo of solubilization and
the molecular weight of the alkyd, either homo-
geneous solutions (low molecular weight, ionic
groups) or- heterogeneous emulsions (high
molecular weight, hydrophilic groups as emul-
sifiers and/or ionic groups) are obtained.
In order to increase the saponification sta-
bility of the hydrophilic group many ap
97
P‘olyethyleneglycol Chalns for Alkyd - Emulsions
,eo
-
Makk Anhydrldo
PolyoxyethykneglycoI - modlfled
Phendresol (hydrqbhllk mokty)
Addltlon product with Alkyd
contalnlng Ekostewk Acid
\
+ NH;
Oh
ALKYD
._
proaches are reported in the literature (includ-
ing patents) where these groups are attached
to fatty .acid moieties by C-C connections.
Figures 11 and 12 show three examples (Engel-
hardt, 1979). The maleated oils are also known
as binders for groundations which are applied
by anodic electrodeposition on metallic sub-
strates used for industrial goods. On the other
hand it is an easy and common route to incor-
porate the potential ionic group into the alkyds
polyester backbone by esterifying trimellitic
anhydride (Patent DE 26 37 167) as shown in
Figure 12.
Specialties
In several industrial systems fatty acids play
an unusual role, e.g. electric insulation fluids
based on a tetrastearate ester of pentaerythri-
tole. The highly purified ester exhibits an out-
98

Methacrylic Acid Contalnlng Copolymer Trimellitic Acid Containing Alkyd

q + +J + nu-”
‘R ‘n
YethactylicEster MathacrylIcAcid Unseed FattyAcid

=
OF0
l-(1 l-

1. Alkyd Synthesis of Copolymer with

Polyols, Dicarboxylic Acid, Fatty Acids

2. Ammonium Formation of the Methacryllc Acid Moiety

Fig. 12. Synthetic approaches to water-soluble alkyds: (a) arafting of methacrylic acid on fatty acid unsaturation; (b)
neutralization of incomplete esterified trimellitic anhydrid~.

TABLE 2 to the polymer backbone (Table 2). This can

easily be achieved by saturated fatty acids or
Physical properties of polyester versus alkyds
their derivatives which are bound to a hydroxy
functional polyester yielding an alkyd resin
Polyester Alkyd Patent DE 36 13 083).

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