Electrochimica Acta 50 (2005) 34463452

Effect of some pyrimidinic Shciff bases on the corrosion

of mild steel in hydrochloric acid solution
H. Ashassi-Sorkhabia, , B. Shaabanib , D. Seifzadeha
a

Electrochemistry Laboratory, Physical Chemistry Department, Faculty of Chemistry, Tabriz University, Tabriz, Iran
b Inorganic Chemistry Department, Faculty of Chemistry, Tabriz University, Tabriz, Iran
Received 30 September 2004; received in revised form 19 December 2004; accepted 19 December 2004
Available online 6 February 2005

Abstract
The efficiency of benzylidene-pyrimidin-2-yl-amine (A), (4-methyl-benzylidene)-pyrimidine-2-yl-amine (B) and (4-chloro-benzylidene)pyrimidine-2-yl-amine, as corrosion inhibitors for mild steel in 1 M HCl have been determined by weight loss measurements and electrochemical polarization method. The results showed that these inhibitors revealed a good corrosion inhibition even at very low concentrations.
Polarization curves indicate that all compounds are mixed type inhibitors. The effect of various parameters such as temperature and inhibitor
concentration on the efficiency of the inhibitors has been studied. Activation energies of corrosion reaction in the presence and absence of
inhibitors have been calculated. The adsorption of used compounds on the steel surface obeys Langmuirs isotherm. It appears that an efficient
inhibition is characterized by a relatively greater decrease in free energy of adsorption. Significant correlations are obtained between inhibition
efficiency and quantum chemical parameters using quantitative structureactivity relationship (QSAR) method.
2004 Elsevier Ltd. All rights reserved.
Keywords: Corrosion inhibitors; Langmuirs isotherm; Quantitative structureactivity relationship

1. Introduction
Acid solutions are widely used in industry. The most important areas of application are acid pickling, acid cleaning,
acid rescaling and oil well cleaning [1]. Corrosion inhibitors
are needed to reduce the corrosion rates of metallic materials
in these media. Most of the efficient inhibitors used in industry are organic compounds, which mainly contain oxygen,
sulphur, nitrogen atoms, and multiple bonds in the molecule
through which they are adsorbed on metal surface [2]. Some
Schiff bases have been reported earlier as corrosion inhibitors
for steel [36], copper [7], aluminum [8,9], and zinc [10].
Some research work [11,12] reveal that the inhibition efficiency of Schiff bases is much greater that of corresponding
amines and aldehydes. This may be due to the presence of a
C N group in the molecule.

Corresponding author. Tel.: +98 4113355998; fax: +98 4113340191.

E-mail addresses: habib ashassi@yahoo.com,
ashassi@tabrizu.ac.ir (H. Ashassi-Sorkhabi).
0013-4686/$ see front matter 2004 Elsevier Ltd. All rights reserved.
doi:10.1016/j.electacta.2004.12.019

The aim of the present investigation is to examine the

inhibitive properties of three Schiff base compounds derived
from 2-amino pyrimidin and corresponding aldehydes.
2. Experimental details
2.1. Materials
Schiff base compounds as inhibitors, shown in Fig. 1, were
synthesized from equimolar amounts of 2-amino-pyrimidin
and the corresponding aldehyde through a condensation reaction in ethanol media [13,14].
The chemical composition (wt.%) of the steel specimen
(determined by SPECTROLAB quantometer) is given in
Table 1. The specimens were polished with emery paper no.
4001200 grade. They were cleaned with acetone, washed
with double-distilled water, and finally dried at room temperature before being immersed in the acid solution. The acid
solutions (1 M) were made from analytical grade 37% HCl

H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

3447

Fig. 1. Structures of studied Schiff bases.

and double-distilled water. The concentration range of inhibitor employed was 2 104 to 1 102 M in 1 M HCl.

Weight loss measurements were carried out as it was

shown in literature [15]. The volume of solution was 100 ml.
The steel specimens had a rectangular form (length: 2 cm,
width: 1 cm, thickness: 0.08 cm). A maximum immersion
time was 24 h in the case of inhibited solutions. Solutions
were not stirred. At the end of the tests, the specimens were
carefully washed in acetone, dried and then weighted. The
temperature of solution was fixed thermostatically a desired
value.

trochemical cell was used. The working electrode was prepared from a mild steel sheet, mounted in polyester such that
the area exposed to solution was 1 cm2 . A saturated calomel
electrode (SCE) and a platinum electrode were used as the reference and the counter electrode, respectively. All potentials
are reported versus SCE. In the case of polarization measurements, the potential sweep rate was 2 mV s1 . The immersion
time before measurements was 1 h. The ac impedance measurements were carried out in the frequency range of 10 KHz
to 10 mHz, at the rest potential, by applying 5 mV sine wave
ac voltage. The double layer capacitance (Cdl ) and the charge
transfer resistance (Rt ) were calculated from Nyquist plots as
described elsewhere [15]. All experiments were performed
under atmospheric conditions.

2.3. Electrochemical studies

2.4. Quantum chemical study

Electrochemical experiments were carried out using an

Autolab, Potentiostat-Galvanostat. A three-electrodes elec-

Quantum chemical parameters for inhibitors, obtained using the AM1 semi empirical quantum chemical approach,
were correlated with their experimental inhibition efficiencies. The following quantum chemical indices were considered: the energy of the highest occupied molecular orbital
(EHOMO ), the energy of the lowest unoccupied molecular orbital (ELUMO ), and the dipole moment ().

2.2. Weight loss measurements

Table 1
Chemical composition of used mild steel specimen (wt.%)
C
Si
Mn
P
S
Cr
Ni
Mo
V
Cu
Nb
Ti
Al
Co
W
Pb
Mg
Sb
Sn
As
B
Fe

0.002
1.380
0.203
0.033
0.009
0.055
0.022
0.019
0.002
0.061
0.001
0.003
0.365
0.002
0.010
0.001
0.001
0.001
0.001
0.014
0.001
97.810

3. Results and discussion

3.1. Linear polarization
Figs. 24 present polarization curves for mild steel electrode in 1 M HCl, in the presence and absence of Schiff bases
at various concentrations. Both cathodic and anodic reactions
on mild steel electrode were inhibited in the presence of studied compounds. The Schiff bases affected cathodic reaction
more than anodic reaction. This result suggests that the addition of inhibitors retards the hydrogen evolution reaction [1].
Electrochemical corrosion parameters, i.e., corrosion potential (Ecorr ), cathodic and anodic Tafel slopes and corrosion
current (Icorr ), obtained by extrapolation of the Tafel lines,
are given in Table 2.

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H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

Fig. 2. Polarization curves for mild steel in 1 M HCl in the presence of Schiff
base A at different concentrations.

Fig. 4. Polarization curves for mild steel in 1 M HCl in the presence of Schiff
base C at different concentrations.

The obtained values of p are given in Table 3. These

results show that all used Schiff base compounds act as
effective inhibitors. Corrosion inhibition increases when
the inhibitor concentration increases. Maximum inhibition efficiency (99.3%) was obtained at a concentration of
1 102 M in the case of C compound.
3.2. Electrochemical impedance spectroscopy (EIS)
Figs. 57 show a typical set of Nyquist plots for mild steel
in 1 M HCl in the absence and presence of Schiff bases at
various concentrations. It is apparent from these plots that
the impedance response of mild steel in uninhibited HCl has
Fig. 3. Polarization curves for mild steel in 1 M HCl in the presence of Schiff
base B at different concentrations.

Table 3
The percentage inhibition efficiency obtained from polarization studies

The inhibition efficiency, p , was calculated from the following equation [16]

Concentration

p = [( Io I)/Io ] 100

0.0002
0.001
0.005
0.01

(1)

where Io and I are the corrosion current densities without and

with an inhibitor, respectively.

Inhibitor efficiency
A

84.8
97.0
97.6
98.7

63.2
96.4
98.1
98.9

75.4
97.5
98.6
99.3

Table 2
Electrochemical corrosion parameters for mild steel in 1 M HCl in the absence and presence of Schiff bases at various concentrations
ba (mV/dec)

bc (mV/dec)

RP ( cm2 )

Icorr (A cm2 )

Inhibitor

Concentration (M)

Ecorr (mV)

Blank

429

98

142

0.0002
0.001
0.005
0.01

420
419
475
488

55
65
205
89

109
79
158
98

31
79
158
98

5.1 104
1.0 104
8.2 105
4.4 105

0.0002
0.001
0.005
0.01

441
443
479
489

78
50
92
104

154
76
97
95

18
107
328
596

1.2 103
1.2 104
6.2 105
3.6 105

0.0002
0.001
0.005
0.01

532
479
445
437

62
77
128
270

133
81
120
196

22
204
560
2121

8.3 104
8.4 105
4.8 105
2.3 105

7.49

3.4 103

H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

Fig. 5. Nyquist plots for mild steel in 1 M HCl in the presence of Schiff base
A at different concentrations.

Fig. 7. Nyquist plots for the mild steel in 1 M HCl in the presence of Schiff
base C at different concentrations.

significantly changed after the addition of Schiff bases in to

the corrosive solutions. The results described below can be
interpreted in terms of the equivalent circuit of the electrical
double layer shown in Fig. 8 which has been used previously to model the iron/acid interface [17]. The capacitance
(Cdl ) and the charge transfer resistance (Rt ) were calculated
from Nyquist plots [15]. In the case of the electrochemical
impedance spectroscopy, the inhibition efficiency is calculated using the charge transfer resistance as follow [15]:
z (%) = [(Rt(inh) Rt )/Rt(inh) ] 100

(2)

where Rt and Rt(inh) are the charge transfer resistance values

without and with inhibitor, respectively.
The electrochemical parameters derived from the Nyquist
plots and the inhibition efficiencies z are given in Table 4.
As can be seen from Figs. 57, the Nyquist plots are not

3449

Fig. 8. Equivalent circuit of the studied system.

perfect semicircles as expected from the theory of EIS for

the assumed equivalent circuit, and this difference can be explained as follows. The Nyquist plots obtained in the real
system represent a general behavior where the double layer
on the interface of metal/solution does not behave as a real
capacitor. On the metal side, electrons control the charge distribution whereas on the solution side it is controlled by ions.
Since ions are much larger than the electrons, the equivaTable 4
Electrochemical impedance parameters for mild steel in 1 M HCl in the
presence and absence of Schiff bases at different concentrations, at 25 C

Fig. 6. Nyquist plots for the mild steel in 1 M HCl in the presence of Schiff
base B at different concentrations.

Cdl (F/cm2 )

z (%)

349

18
60
159
166

157.9
72.6
38.8
34.9

54.8
79.2
88.9
90.0

1.3
1.2
1.2
1.8

46
88
164
248

70.0
68.9
53.9
25.3

79.9
80.3
84.6
92.8

1.3
1.3
1.3
2.3

34
98
204
397

97.8
48.4
31.6
14.6

71.8
86.1
90.9
95.8

Inhibitor

Cinh (M)

Rs ( cm2 )

Blank

1.3

0.0002
0.001
0.005
0.01

1.4
1.2
1.4
1.1

0.0002
0.001
0.005
0.01

0.0002
0.001
0.005
0.01

Rt ( cm2 )

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H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

lent ions to the charge on the metal will occupy quite a large
volume on the solution side of the double layer [18]. It can
be obtained from Table 4 that, the capacitance of electrical
double layer (Cdl ) decreases in the presence of inhibitors. Decrease in the Cdl , which can result from a decrease in local
dielectric constant and/or an increase in the thickness of the
electrical double layer, suggests that the inhibitor molecules
act by adsorption at the metal/solution interface [12,19].
The inhibition efficiency follows the order:
C>B>A
As known, some atoms, such as O and N atoms of Schiff
bases, which have unoccupied orbitals, so exhibit a tendency
to obtain electrons. The electrons in the d orbitals can easily
be offered because their applied force is small. If an inhibitor
does not only offer electrons to un occupied d orbitals of
metals, but it can also accept the electrons in d orbitals of
metallic steel by using their antibond orbital to form stable
chelate, then it may be considered an as excellent inhibitor
[20]. The presence the electron donating groups on the Schiff
bases structure (such as Cl and CH3 ) increases the electron
density on the nitrogen of the C N group, resulting high
inhibition efficiency. Among the compounds investigated in
the present study, C has been found to give the best performance as corrosion inhibitor. This can be explained on the
basis of the presence of chloride group on the benzene ring.
3.3. Weight loss measurements
The values of inhibition efficiency and corrosion rate obtained from weight loss method at different concentrations of
inhibitors at 25 C are summarized in Table 5.
It has been found that all of these compounds inhibit the
corrosion of mild steel in HCl solution at all concentrations
used in this study. It has also been observed that the inhibition efficiency for all of these compounds increases with the

Fig. 9. Langmuirs isotherm for adsorption of Schiff bases on the steel surface.

increase in concentration. This fact could be expressed that

these compounds acts as adsorption inhibitors. Plotting suitable adsorption isotherm could prove it. In fact, log /(1 )
against log C of Schiff bases gives straight lines with unit
slope (Fig. 9) indicates that adsorption of Schiff bases on
the steel surface follows the Langmuirs adsorption isotherm.
From these results it could be concluded that there is no interaction between the inhibitor molecules adsorbed at the metal
surface [21].
The values of corrosion rate and inhibition efficiency of
Schiff bases at 0.1 M concentration at different temperatures
are given in Table 6. It can be seen that the inhibition efficiency for all of the compounds slightly decreases with increasing temperature from 25 to 43 C. It may be explained
by desorption of adsorbed inhibitor from the steel surface.
The values of activation energy (Ea ) were calculated using
Arrhenius equation [22,23]. The free energy of inhibitor adsorption (Gads ) at 25 C was calculated from the following
equation [21]:
Gads = RT ln(55.5K)

Table 5
Corrosion parameters for mild steel in 1 M HCl in the presence and absence of Schiff bases at different concentrations, obtained from weight loss
measurements at 25 C
Inhibitor

Concentration
(M)

Surface coverage
()

Inhibition efficiency,
w (%)

Blank

0.0002
0.001
0.005
0.01

0.582
0.902
0.961
0.990

58.2
90.2
96.1
99.0

0.0002
0.001
0.005
0.01

0.879
0.967
0.985
0.989

87.9
96.7
98.5
98.9

0.0002
0.001
0.005
0.01

0.679
0.962
0.987
0.994

67.9
96.2
98.7
99.4

(3)

Table 6
Corrosion parameters of mild steel in 1 M HCl in the presence and absence
of 0.01 M of Schiff bases at different temperature, obtained from weight loss
measurements
Inhibitor Temperature Corrosion
Surface
Inhibition
( C)
rate (mg/cm2 h) coverage () efficiency, w (%)
Blank

25
34
43

0.549
0.982
1.220

25
34
43

0.005
0.021
0.049

0.990
0.978
0.960

99.0
97.8
96.0

25
34
43

0.006
0.014
0.045

0.989
0.986
0.963

98.9
98.6
96.3

25
34
43

0.003
0.016
0.029

0.995
0.984
0.976

99.5
98.4
97.6

H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

Table 7
Activation energy (Ea ) of corrosion and free Gibbs energy (Gads ) of Schiff
bases adsorption obtained from weight loss measurements

3451

Table 8
Quantum chemical parameters for used Schiff bases obtained from AM1
method

Inhibitor

Temperature ( C)

Ea (kJ/mol)

Gads (kJ/mol)

Inhibitor

EHOMO (eV)

ELUMO (eV)

E (eV)

(D)

Blank

34.92

25
34
43

79.56

31.53
33.03
34.00

A
B
C

9.3487
9.1665
9.3598

0.9333
0.9132
1.0908

10.2820
10.0797
10.4506

0.580
1.835
2.797

25
34
43

88.97

31.93
32.56
33.52

25
34
43

99.36

32.99
33.98
34.97

where K is given by:

K = /C(1 )

(4)

where is the degree of coverage on the metal surface, C the

concentration of inhibitor in mol l1 and K the equilibrium
constant. The values of the free energy and the activation
energy are given in Table 7.
It was found that, Ea values for inhibited systems are
higher than Ea for uninhibited system. This results that physical adsorption occurred in the first stage, which explains the
nature of organic moleculesmetal interactions. On the other
hand, physical adsorption is related to lower values of the activation energy (3050 kJ mol1 ). So these criteria cannot be
taken as decisive to competitive adsorption with water whose
removal from the surface requires also some activation energy [24]. The low and negative value of Gads indicated the
spontaneous adsorption of inhibitor on the surface of mild
steel [25,26].
3.4. Quantum chemical study
Since the electronic properties can change by an addition of a functional group to the molecule, the inhibitor efficiency can be treated as a controlled property.
The synthesis of better corrosion inhibitors then can be
achieved by controlling electronic properties of a selected
group of Schiff base molecules. In addition, the correlations between the inhibition efficiency and molecular parameters can be used for pre-selection of new inhibitors,
which are, at the moment, taken essentially from empirical knowledges [19]. Quantum structureactivity relationships (QSAR) has been used to study the effect of molecular structure on the inhibition efficiency of the used Shciff
base compounds. Satisfactory correlation has been recorded
between the inhibition efficiency of some inhibitors and
some quantum chemical parameters by other investigators [12,2729]. The calculated quantum chemical indices
(EHOMO = energy of the highest occupied molecular orbital,
ELUMO = energy of the lowest unoccupied molecular orbital
and dipole moment ) of Schiff bases obtained using AM1

semi empirical quantum chemical approach are shown in

Table 8.
The average values of inhibition efficiency (m ), obtained
using three experimental methods (EIS, linear polarization
and weight loss) were used for QSAR modeling (Table 9).
Linear and non-linear QSAR models have been used in this
case.
Not only the electron of the Schiff bases enter unoccupied orbitals of iron, but the * orbital can also accept the
electrons of d orbitals of metallic iron to form feed back bonds
[12]. In order to prove the forming of feed back bonds, a linear
regression analysis was performed on the average inhibition
efficiency versus the HOMO energy (EH ) and LUMO energy
(EL ) of the Schiff bases A, B, C, and the following equation
was obtained.
(%) = 3.362 EHOMO 7.094ELUMO + 122.761

(5)

Inhibition efficiency increases with increasing values of

EHOMO . The results seem to indicate that charge transfer
from the inhibitor takes place during the adsorption on the
metal surface. Increasing values of the EHOMO may facilitate adsorption (and therefore inhibition) by influencing the
transport process through the adsorbed layer. EHOMO is often
associated with the electron donating ability of a molecule.
Therefore, the energy of the lowest unoccupied molecular orbital (ELUMO ) indicates the ability of the molecules to accept
electrons. The lower value of ELUMO , the more probable, that
the molecule would accept electrons [12,18].
The coefficients of EH (positive) and EL (negative) prove
that the main aspect of the forming of feed back bonds is the
ability of the inhibitors to offer electrons, so the inhibition
Table 9
Inhibition efficiency obtained from different methods and their average
Inhibitor

Cinh

Hw (%)

p (%)

z (%)

m (%)

0.0002
0.001
0.005
0.01

58.2
90.2
96.1
99.0

84.8
97.0
97.6
98.7

54.8
79.2
88.9
90.0

65.9
88.8
94.2
95.9

0.0002
0.001
0.005
0.01

87.9
96.7
98.5
98.9

63.2
96.4
98.1
98.9

79.9
80.3
84.6
92.8

77.1
91.1
93.7
96.9

0.0002
0.001
0.005
0.01

67.9
96.2
98.7
99.4

75.4
97.5
98.6
99.3

71.8
86.1
90.9
95.8

77.8
93.3
96.1
98.2

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H. Ashassi-Sorkhabi et al. / Electrochimica Acta 50 (2005) 34463452

Fig. 10. Correlation between the experimental inhibition efficiency (obtained from LP, EIS and weight loss methods) and the calculated inhibition
efficiency (obtained from QSAR).

efficiency values of the three Schiff bases follow the order:

C>B>A
The non-linear equation was used to correlate all quantum
chemical parameters (EH , EL , ) and inhibitor concentration (Cinh ) with the experimental inhibition efficiencies. The
non-linear model proposed by Lukovits et al. [30] for the interaction of corrosion inhibitors with metal surface in acidic
solutions has been used in this part of the study. The following proposed relation between inhibition efficiency, and
quantum chemical index was used:
(%) = (Axj + B)Ci /(1 + (Axj + B)Ci )

(6)

where A and B are the regression coefficients to be determined by regression analysis; xj a quantum chemical index
characteristic of molecule j; Ci denotes the concentration in
an experiment i. In this case, xj is constructed, as a composite
index of quantum chemical parameters; EHOMO , ELUMO and
. Following equation is obtained for the three compounds.
(%) =

(AEHOMO + BELUMO + C D)Cinh

1 + (AEHOMO + BELUMO + C D)Cinh

(7)

where A, B, C, D are 526.325, 977.031, 107.937 and

2150.147, respectively. The plot of the experimental and the
calculated inhibition efficiency of compound A, B, and C is
presented in Fig. 10. Highly significant multiple correlation
coefficient (R2 ) between experimental and calculated efficiencies was obtained.

4. Conclusion
1. All examined Schiff base compounds act as good corrosion inhibitor in HCl media.
2. These compounds inhibit both anodic and cathodic reaction by adsorption on the steel surface.

3. Corrosion inhibition of used compounds increases when

their concentration increases.
4. Substitution of Cl and CH3 group on the benzene ring
increases the inhibition efficiency.
5. Corrosion inhibition decreases when the temperature increases.
6. Adsorption of Schiff bases on the steel surface is spontaneous and obeys the Langmuirs isotherm.
7. Results obtained from all applied experimental methods
are in good agreement.
8. Inhibition efficiency of Schiff bases increases when
the HOMO energy increases and the LUMO energy
decreases.
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