Utilization Soya Bean Fatty Acid for Synthesis of Alkyd Resin and Comparation of

Properties with Other Vegetable Oils

H. Aghaie 1, A.R. Ilkhani 1*, S. M. Sadat Choobeh1
1. Department of Chemistry, Science and Research Branch, Islamic Azad University,
Tehran, Iran(ilkhaniali@yahoo.com)
ABSTRACT
In this study, alkyd resin was synthesized rate of decreasing of resins acid value and
increasing of viscosity of resin were measured. FTIR spectroscopy, GPC method and
different viscosity measurements employed to determination properties of product.
FTIR spectroscopy was employed for identify of structure of resin and gel permeation
chromatography (GPC) was used for determination of number average molecular
weight (Mn) and polydispersity (PDI). Finally fatty acids composition of vegetable oil
such as Coconut, Castor, Linseed, Palm, Sunflower and Tung oils have compared with
Soya bean oil.
Keywords: Alkyd resin synthesis; Soya bean fatty acid; Unsaturated hydroxylated
Polyester; Unsaturated vegetable oil

INTRODUCTION
Alkyd resins are major important
binders which they are the largest
volume base of coatings and paints
especially for decorative applications
[1]. The term alkyd is derived from two
parts "al" which referred prefix
abbreviation of alcohol and "kyd" which
referred suffix abbreviation of acid and
they are the products of the
esterification of polybasic acids and
polyhydric alcohols [2].
Alkyd resins are using for decorative
painting applications more than other
binders because of lower cost; low price
of alkyd resins related to inexpensive
raw material, easy manufacturing and
high solubility of resin in less expensive

solvents. Alkyd resins not only are used

in decorative paints but also mainly are
applied in air drying and stoving paints,
inks, machine toll finishes and clear,
matt and semi matt varnishes of wood
furniture[3].
The
unsaturated
hydroxylated
polyesters resins which they have
modified with vegetables, marine oils or
their fatty acid called alkyd resins [1],
therefore alkyd resins are main product
of poly condensation reactions between
poly carboxylic acids and poly alcohol
in present fatty acids or vegetable oils
[2]. This kind of reaction had obtained
by following formula:
::

Poly carboxylic acids + Poly alcohols + Fatty acids, Vegetable oils Alkyd Resin + H2O

Poly alcohols which mainly are using

for
condensational
polymerization
reactions of alkyd resins content
Ethylene glycol, propylene glycol,
aromatic poly basic acids and aliphatic
poly basic acids; for preparation of
alkyd binders usually are employing
aromatic poly carboxylic acids such as
phthalic anhydride, isophthalic acid; but
cycloaliphatic anhydrides such as,
hexahydrophthalic
anhydride,
also
malic anhydride are using for alkyd
resins esterification reactions [3-4].
Suitable chose of types of poly basic
acids and poly alcohols in reaction not
only will prevent of gelation of alkyd
resins reaction but also will give chance
to easy control of process of
polymerization of alkyd resins to
operator. Benzoic acid and others mono

diethylene glycol and pentaerythritol.

Inaddition poly carboxylic acids are
using for alkyd resins reactions divided
to
two
different
branches,
basic carboxylic acid are used for alkyd
resins formulation including high
functionality system to act as chain
stopper [5].
Indeed alkyd resins formula is
modified with varying amounts of fatty
acids with the exception of rosin, almost
all of these monobasic fatty acids are
derived from the vegetable drying,
semidrying oils or marine semidrying
oils which these are glycerol esters of
their acids. The important and famous
vegetable drying and semi drying
vegetable oils composition which they
usually have used for alkyd resin have
shown Table 1.

Coconut
oil

Castor
oil

Linseed
oil

Palm
oil

Sunflower
oil

Soya Bean
oil

Tung
oil

Caprylic
Capric
Lauric
Myristic
Palmitic
Stearic
Oleic
Ricinolic
Linoleic
Linolenic
Eleostearic
Licanic
Iodine
Value

C8H16O2
C10H20O2
C12H22O2
C14H28O2
C16H32O2
C18H36O2
C18H34O2
C18H34O2
C18H34O2
C18H30O2
C18H30O2
C18H30O2

0
0
0
0
0
0
1
1
2
3
3
3

--------

----

6
6
44
18
11
6
7
---2
---------7.510.5

------------2
1
7
87
3
---------8191

------------6
4
22
---16
52
------155136

---------1
48
4
38
---9
---------44 54

------------11
6
29
---52
2
------120141

------------11
4
25
---51
9
------120141

------------4
1
8
---4
3
80
---160175

Molecular
formula

Fatty acid

Double
bond

Table 1: fatty acid composition of some important vegetable oils

Tab 2: Classification of alkyd resins based on length of oil and properties of resins.
Variations in the amounts and types of
components special for fatty acids given
enormous varieties of alkyd resins with
different mechanical and reological

properties, thus alkyd resins are often

classified with the oil type, the oil
length and application. Tab.2 show
classification of alkyd resins based on

Parameter
of Resins
Length of
Oil
% Fatty
Acid
% Phethalic
Anhydride
Suitable
Solvent
% Solid of
Resin
Preparation
of Film

Short
Oil
25-47

Classification of Alkyd Resins Based on Length of Oil

Medium
Medium
Long
Long
Very Long
Short Oil
Oil
Medium Oil
Oil
Oil
43-47
47-56
53-56
56-74
74-85

30-39

40-45

45-50

50-55

55-70

70-80

38-50

36-38

33-36

30-33

20-30

10-20

Aromatic

Aromatic

Aliphatic

Aliphatic

Aliphatic

Aliphatic

45-50

50

50-55

60

60-70

70-100

Thermoset
High
Temperature

Thermoset
High-Low
Temperature

Thermoset
Low
Temperatur

Thermoplast

Thermoplast

Thermoplast

different items such as length of oil,

percentage of fatty acids and phethalic
anhydride which they used in
EXPERIMENTAL
The experimental materials have used
for experimental tests such as titrations
and
others
test
which
exact
measurement of values were important
of them and industrial materials have
used for synthesis of alkyd resins
because of industrial aims.
Potassium
hydroxide,
Potassium
dichromate,
Potassium
iodide,
Potassium
hydrogen
phthalate,
Bromine, Chloroform, Acetic acid,
Phenolphthalein, Iodine, Isopropyl
alcohol and Sodium tiosulphate have
used as experimental materials and all
this material had produced by Merk
company.
Industrials materials have utilized for
syntheses of resins, content: Soya fatty
acid from Paxan Company of Iran, titer
point 23 C and Iodine number 123 mg
KOH/g fatty acid, Phetalic anhydride
from IG. Petrochemical Company of
India, melting point 133 C and acid
number 391 mg KOH/g fatty acid,
maleic anhydride from USP Technology
Group of Taiwan, melting point 54 C
and acid number 522 mg KOH/g fatty
acid, Glycerin from EVYAP Company
from Turkey, purity percent 99.5%,

formulation of resins and

properties of alkyd resin [5-7].

other

Pentaerythritol from Koninda Canada,

melting point 248 C, White sprit
solvent from Petrochemical Company
of Iran, boiling point149 C, Toluene
from Petrochemical Company of Iran,
boiling point 111 C have used.
Equipments as have used in this work,
classified to three sections: glass
equipments which they applied for
titrations .Equipments as applied for
producing process of alkyd resin and
tests for control the products during the
process and after finishing. These are:
Ben
marry
thermostat
NLW-8,

sensitivity 0.1 C; Glass separator,

sensitivity 0.1 M; Blender Heidolph
model RZR2020, 80-2000 cycle per
minute; Stanlees steel turbine agitator;
Glass reactor, volume

2Liter; Glass condenser, length 70 cm

length; Gardner viscometer model MT,
BYK Company of Germany; Gardner
color meter model MT, BYK Company
of Germany; Electrical melting pointer,
Tebazma Company of Iran; Electrical
heater up to 350 C, sensitivity 1 C.

Equipment for identification of structure

of resin and viscosities tests, these are:
FTIR spectrometer model BRUKER-IF

548, Gel Chromatographer GPC model

MAXIMA
820
and
Brookfield
viscometer model ST-DIGIT R.

Figure 1: scheme of Alkyd Resin Reactor [5]

Alkyd resin which it synthesized in this study is according fallowing formulation:
Toluene

Glycerin

2.47

13.47

Penta
erythritol
8.05

Acid value(mg KOH/g Resin),

Viscosity(Stock)

RESULTS AND DISCUSSION

Acid value curve of synthesized alkyd
resins (figure2) illuminate that in
condensation polymerization reaction of

Malic
Anhydride
0.86

Phetalic
Anhydride
28.99

Soya Fatty
acid
46.16

alkyd resin acid value of binder has

decreased, also viscosity of alkyd resin
has increased.

60
50
40

Acid value
Viscosity

30
20
10
0
6:00 8:00 9:30 10:50 11:50 12:30 13:20 13:50
Time after start Reflux( hr)

Figure 2: Acid number and Viscosity curve of synthesized long oil alkyd resin at 25C.
For
synthesized
resin
FTIR
spectroscopy have done which it is a
powerful method for evaluation of
chemical structure of organic compound
(figure 3a) for estimated position

functional groups in polymer molecule

of resin.
Determination of distribution of
average molecular weight of alkyd resin
synthesized is very important for

characterizing
of
products.
Gel
Permeation Chromatography (GPC)
have employed for evaluation of
average molecular weight and for
determination of maximum peak of
alkyd resin product. Figure 3b clearly
shows distribution of molecular weight
for alkyd resin synthesized. In gel
chromatographs unit of X axe is
minutes times 10 and unit of Y axe is
volts multiplied on 10-1.

(a)

GPC method not only have used for

determination of distribution of
molecular weight of resins it called
polydispersity (PDI), but also have
applied for determination of numeric
average molecular weight (Mn), weight
average molecular weight (Mw) and
viscosity average molecular weight
(Mv).

(b)

Figure 3: FTIR (a) and GPC (b) spectrums of alkyd resin

CONCLUSION
Viscosity of synthesized alkyd resin
60% in White Sprite at 25C have
measured two different methods;
Brookfield viscometer by spindle R4
have shown 5500 centi poise and
viscosity Ford cup 6 have measured 180
seconds. Determination of distribution of
average
molecular
weight
of
synthesized alkyd resin has shown Mn
12179, Mw and Mv 18666 also PDI,
1.5325 which they are normal range of
alkyd resin properties. Peaks 3503, 1732
and 2926, 2854 cm-1 involve O H
acid and alcohol , C = O ester , CH2
stretching of alkyd resin.
REFERENCES
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Technology, vol.2, 3nd ed, Pishro
Publication, Iran, 1992
2- M.A.Mazandarani, Paint and Resin
Technology, vol.1, 3nd ed, Pishro
Publication, Iran, 1992

3- M. N. S. Kumar , Z. Y. Maimunah,
S. R. S. Abdullah ,Synthesis of Alkyd
Resin from Non-Edible Jatropha Seed
Oil, J. Polym. Environ., vol.18, 2010
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and S.Peter Pappas , Organic Coating
Science and Technology , 2nd ed ,
Wiley Inter science Publication,
Canada ,1999
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Dullius, S. Einloft ,Utilization of palm
oil in the alkyd resin synthesis,
Faculdade de Quimica - Laboratrio de
Organometlicos e Resinas,2005
6- Dutta, N.; Karak, N.; Dolui, S. K.
Prog. Org. Coat., 146-152 , vol.49, 2004
7- T C .Patton Baker, Alkyd Resin
Technology: Formulating Techniques
and Allied Caster Oil Company, InterScience Publication, 1962