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Journal of Surfactants and
Detergents
ISSN 1097-3958
Volume 18
Number 3
J Surfact Deterg (2015) 18:529-535
DOI 10.1007/s11743-014-1662-6
Synthesis and Characterization of
Cationic Surfactants Based on N-
Hexamethylenetetramine as Active
Microfouling Agents
Rafat M. Mohareb, Abdelfatah
M. Badawi, Mahmoud R. Noor El-
Din, Nesreen A. Fatthalah & Marian
R. Mahrous
1 23
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ORIGINAL ARTICLE
Synthesis and Characterization of Cationic Surfactants Based
on N-Hexamethylenetetramine as Active Microfouling Agents
Rafat M. Mohareb • Abdelfatah M. Badawi •
Mahmoud R. Noor El-Din • Nesreen A. Fatthalah •
Marian R. Mahrous
Received: 16 January 2014 / Accepted: 10 December 2014 / Published online: 3 January 2015
Ó AOCS 2014
Abstract Four cationic surfactants of quaternary hex-
ammonium silane chloride based on hexamethylenetetra-
mine and alkyl chloride were synthesized. The chemical
structures of the prepared cationic surfactants were eluci-
dated using Fourier transform infrared (FT-IR) spectros-
copy and mass spectrometry analysis. The surface and
thermodynamic properties of the prepared surfactants were
also studied. The performance of these cationic surfactants
as microfouling agents against two strains of Gram-nega-
tive bacteria, namely, Pseudomonas aeruginosa and
Escherichia coli, and two strains of Gram-positive bacteria,
namely, Staphylococcus aureus and Bacillus subtilis, were
evaluated as antimicrobial agents. The results showed that
the maximum antimicrobial activity was detected for N-
hexamethylenetetramine-N-ethyl silane ammonium tri-
chloride (Ah). The maximum and minimum antimicrobial
activities were 73 and 60 % against S. aureus and E. coli,
respectively, at a concentration of 5 mg/l, pH 7, and 37 °C.
Keywords Microbial fouling Á Quaternary
hexammonium silane Á Cationic surfactants Á Antimicrobial
activity
Introduction
One of the most important problems facing the marine
industries is biofouling, which affects underwater infra-
structure components such as electrical cables, petroleum
pipelines, fishing nets, etc. [1]. Microbes, bacteria, micro-
algae, and higher microorganisms, e.g., aquatic fungi, infu-
soria, rotifers, etc., live and multiply on the surfaces of
pipelines immersed in water, refrigerators, and heat
exchangers, inside flameless heating equipment in the pre-
sence of aqueous media, and in systems for biochemical
treatment of wastewaters. Heat and mass exchange worsen
sharply, thermal power consumption increases, output and
passability decrease, accidents occur in manufacturing units,
and corrosion of metal surfaces intensifies as a result of
biological fouling of this equipment [2]. Marine microor-
ganisms like Escherichia sp., Staphylococcus sp., and
Pseudomonas sp. are known to be effective in the biofouling
process [3]. Moreover, Pseudomonas sp., the most prevalent
in the water and seawater industries, have been implicated in
the corrosion process of stainless and mild steels, and alu-
minum alloys in marine habitats. In industrial settings of
cooling-water towers, water pipelines, membrane unit, and
food-processing plants, the unwanted biofilms of Staphylo-
coccus aureus and Staphylococcus epidermidis are respon-
sible for fouling [4]. The most widely practiced approach to
the minimization of biofilms in industrial water systems is by
way of chemical treatment focusing either on the reduction
of microbial numbers using biocides, or their removal using
either synthetic dispersants or enzymes [5]. Different types
Electronic supplementary material The online version of this
article (doi:10.1007/s11743-014-1662-6) contains supplementary
material, which is available to authorized users.
R. M. Mohareb
Department of Chemistry, Faculty of Science, Cairo University,
Giza, Egypt
A. M. Badawi Á M. R. Noor El-Din (&) Á N. A. Fatthalah
Egyptian Petroleum Research Institute, 1 Ahmed El- Zomor St.,
Nasr 11727, Cairo, Egypt
e-mail: mrned04@yahoo.com
M. R. Mahrous
Science and Technology Center of Excellence, Cairo, Egypt
123
J Surfact Deterg (2015) 18:529–535
DOI 10.1007/s11743-014-1662-6
Author's personal copy
of surfactants can act as antimicrobial agents by interaction
with a microorganism’s cellular membranes [6, 7]. However,
the surfactants are easily adsorbed at liquid–solid interfaces
and can protect different surfaces from microorganism
adhesion by forming protective coated surfaces [8].
The first use of cationic surfactants in the field of anti-
bacterial resistance was recorded by Domagk in 1935 [9] and
since that date, hundreds of new cationic surfactants have
been synthesized and used as germicides and/or fungicides
[10]. Alkyl pyridinium, alkyl trimethylammonium halides
and hexamine derivatives, and 1-(3-chloroallyl)-3,5,7-triaza-
1-azoniaadamantane chloride are the most widely com-
pounds used in the field of biofouling resistance [10, 11].
Also, quaternary ammonium compounds (QACs) are com-
monly used as effective biocidal agents, as they have superior
properties compared to known antibacterial agents such as
better membrane penetration, excellent environmental sta-
bility, lower toxicity, higher corrosion inhibition effect, and
lower skin irritation [12–16]. QACs have a broad spectrum of
antimicrobial activity against both Gram-positive and Gram-
negative bacteria [17]. As QACs are positively charged
cations, their mode of action is related to their attraction to
negatively charged materials such as bacterial proteins [18].
The objective of the present work was to synthesize a new
series of cationic silicon-based quaternary hexammonium
surfactants for use as microfouling agents. These surfactants
were prepared by condensing an amine (containing a triva-
lent nitrogen) with alkyl silicon mono-, di-, and trichlorides.
The efficiency of the prepared surfactants as microfouling
agents against three strains of bacteria was investigated. In
addition, the effect of surface and thermodynamic parameters
on the efficiency of the synthesized surfactants was studied.
Experimental
Materials
Analytical grades of hexamethylenetetramine, trichloroeth-
ylsilane, trichlorohexylsilane, dichlorodiethylsilane, and
chlorotriethylsilane were purchased from Sigma–Aldrich
Co., UK. Technical grade dimethylformamide (DMF) was
obtained from Fluka, Germany. Deionized water was uti-
lized in all experiments.
Method
Synthesis of Quaternization
of Hexamethylenetetramine
A 0.1-mol sample of each silane, namely, trichlorohex-
ylsilane, trichloroethylsilane, dichlorodiethylsilane, and
chlorotrimethylsilane, was reacted with hexamethylenetet-
ramine (0.3, 0.3, 0.2, and 0.1 mol, respectively; the number
of moles of hexamethylenetetramine was chosen on the
basis of the number of chlorine groups in the silane). At the
beginning of each reaction, the hexamethylenetetramine
was dissolved in 40 ml of hot DMF and then treated with
the silane in a 500-ml flask fitted with a Dean-Stark trap
equipped with a condenser and continuously stirred at
400 rpm for 8 h. The reaction mixture was cooled and
filtrated. The precipitate was washed with acetone. The
solvent was evaporated using an evaporator. Each of the
prepared surfactant was washed twice with acetone and left
in room temperature for drying until constant weight. The
chemical structure of the synthesized quaternary hexam-
monium chloride surfactants is shown Fig. 1.
Chemical Conformation
The chemical structures of the prepared surfactants were
confirmed using Fourier transform infrared (FT-IR) spec-
troscopy (Thermoscientific, Nicolet iS10 FT-IR, USA) and
mass spectrometry analysis (Alpha Omega Technologies,
Inc., Brielle, NJ).
Evaluation of the Synthesized Surfactants
as Microfouling Agents
The antimicrobial activity of each of the synthesized cat-
ionic surfactant, namely, N-hexamethylenetetramine-N-
ethylsilane ammonium trichloride (Ah), N-hexamethy-
lenetetramine-N-diethylsilane ammonium dichloride (Dh),
N-hexamethylenetetramine-N-triethylsilane ammonium
chloride (Ch), and N-hexamethylenetetramine-N-hexylsi-
lane ammonium trichloride (Bh), was evaluated as a
microfouling agent against four bacterial strains: Pseudo-
monas aeruginosa ATCC 10145, Escherichia coli ATCC
23282 (Gram-negative bacteria), and Staphylococcus aureus
ATCC 29737, Bacillus subtilis NCTC 10400 (Gram-positive
bacteria) using both the agar well diffusion method and
minimum inhibitory concentration (MIC) test [19, 20].
Agar Well Diffusion Method
The agar well diffusion method depends on the diffusion of
the prepared surfactants through a layer of solidified agar
that inhibits the growth of the microorganism in an area or
zone around the hole containing the antibiotic solution. In
this assay, the size of the inhibition zone and the dose of
the surfactants assayed are correlated. In this study, the
antimicrobial susceptibility was tested on solid (agar–agar)
media. The medium was inoculated with the tested
microorganisms separately and poured into sterilized Petri
dishes (20 ml/dish). The agar medium was punched using a
530 J Surfact Deterg (2015) 18:529–535
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sterile cork borer to make five holes of 10 mm. For each
surfactant, a stock solution was prepared at a concentration
of 5 mg/ml. About 100 ll of each stock solution was added
using a sterile micropipette into four holes and allowed to
diffuse at 4 °C for 2 h and then incubated at 37 °C for
24 h. The fifth hole was filled with control solution (which
has no surfactant). The negative control was DMF that
showed no antimicrobial activity against the tested
microorganisms. The diameter of the inhibition zone
(millimeters) was measured. The previously step was
repeated twice for each surfactant and the average values
were recorded [20].
Minimum Inhibitory Concentration (MIC) Test
In microbiology, MIC is defined as the lowest concentra-
tion of an antimicrobial that inhibits the visible growth of a
microorganism after overnight incubation [21]. Serial
dilutions of the four tested compounds were prepared in
macrodilution tubes at a range of concentrations (dilution
N
N
N
N
RSiCl(x)
Hexamethylenetetramine
(C6H12N4)
where R=2 or 3 molecules of ethyl group
R
=1 molecule of ethyl or hexyl group
x=1, 2 or 3
Si Cl
Si
N4C6H12
C2H5
Cl
Si
R
C2H5
C2H5C2H5
C2H5
or
R
SiCl(x)
N-hexamethylene tetramine -N-
diethyl silane ammonium dichloride
(Dh)
N-hexamethylene tetramine-N-
triethyl silane ammonium chloride
(Ch)
N-hexamethylene tetramine -N-alkylsilane ammonium trichloride
(Ah and/or Bh)
Alkyl silicon chloride
+2
-2
+1
-1
N4C6H12
N4C6H12
+3
Cl
-3
N4C6H12
N4C6H12
H12C6N4
Fig. 1 Chemical structure of
the synthesized quaternary
hexammonium chloride
surfactants
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factor ranging from 1/2 to 1/64). Bacterial suspensions
were adjusted to the logarithmic growth phase to match the
turbidity of a 0.5 McFarland standard, yielding approxi-
mately 108
CFU/ml. The same amounts of bacteria were
added to all tubes and the tubes were incubated at 37 °C for
24 h. Each tube was examined for growth and compared to
the control. Bacterial suspension added to a tube filled with
nutrient broth without each of the tested compounds was
used as a positive growth control. A tube not containing
nutrient broth was used as a negative growth control. The
absence of growth was defined as antibacterial activity.
Surface Tension Measurements (c)
The surface tension (c) of the prepared cationic surfactants
at 25 °C was measured using a Du Nou¨y tensiometer
(Kruss-K6 type) by applying the platinum ring technique.
The surface tension of each surfactant was measured three
times within a 3-min interval between each reading [22].
The critical micelle concentration (cmc) was determined
from the abrupt change in the slope of surface tension
(ccmc) versus logarithm of the concentration curve (ln C).
From the slope of a plot of c versus ln C, the maximum
surface excess concentration (Cmax) and the minimum
surface area per surfactant (Amin) were calculated. Also, the
thermodynamics parameters of adsorption and micelliza-
tion Gibbs free energies, such as Gibbs free energy of
adsorption (DGads) and the Gibbs free energy of micelli-
zation (DGmic), for the prepared surfactants were calculated
by utilization of Gibb’s adsorption equations [23].
Results and Discussion
Characterization of Quaternary Hexammonium Silane
Compounds
The prepared surfactants (Ah, Bh, Dh, and Ch) were
characterized using both FT-IR spectroscopy and mass
spectrometry analysis and the biological activities are
discussed in the following section.
FT-IR Spectroscopic and Mass Spectrum Analyses
The structures of the prepared quaternary hexammonium
silane chloride compounds (Ch and Ah) were elucidated by
FT-IR. The FT-IR spectrum in Fig. S2 is dominated by a
Si–N peak around 900 cm-1
, a Si–C peak at 1,010 cm-1
,
and a C–N peak around 2,350 cm-1
. Figure S3 shows that
the peak intensity at 900 cm-1
is larger in compounds with
higher Si–N content and increases as the extent of hexa-
methylenetetramine increases. This band indicates that
more than one molecule of N-hexamethylenetetramine was
introduced. Also, the decrease of the peak intensity at
1,010 cm-1
indicates that the prepared compound contains
more than one ethyl group. The chemical structures of the
quaternary hexammonium silane compounds were also
confirmed by mass spectrometry (Fig. S2–S4; Table S1 in
supplementary information).
Biological Activity of the Synthesized Surfactants
The synthesized compounds (Ah, Dh, Ch, and Bh) were
evaluated for their microfouling action against P. aerugin-
osa and E. coli as Gram-negative and S. aureus and B.
subtilis as Gram-positive bacteria (Fig. 2). Commonly,
Gram-negative bacteria are resistant towards antibacterial
substances owing to the presence of lipopolysaccharide
molecules in their outer membrane, acting as a barrier to the
penetration of numerous antibiotic molecules which are
related to the enzymes in the periplasmic space that are able
to break down the molecules introduced from outside [24–
26]. By inspection of the data in Fig. 2, the efficiency of the
prepared cationic surfactants is in the order Bh [ Ch =
Dh [ Ah for E. coli, and Ah = Bh [ Ch = Dh for
P. aeruginosa. Also, the maximum inhibition zone was
afforded by Bh surfactant for both organisms. This may be
attributed to the effect of the number of alkyl groups for Ah,
Ch, and Dh and to the length of Bh surfactant on its
adsorption onto the bacterial cell wall. However, the results
show that Ch and Dh have lower inhibition (inhibition
zone = 20 cm) efficiency against P. aeruginosa than that
of Ah (inhibition zone = 24 cm) and this may be attributed
to the number of alkyl groups. Also, the results show that Bh
surfactant have a high inhibition zone (3.5 cm) comparing
with Dh, Ch, and Ah; this may be attributed to the effect of
alkyl group length. Regarding Gram-positive bacteria, the
highest antimicrobial activity against S. aureus was affor-
ded by Ah surfactant (Fig. 2). As a result of the structure of
the cell wall of Gram-positive bacteria, which consists of
0
5
10
15
20
25
30
35
40
45
50
+ve control Ah Bh Ch Dh
Surfactant
Inhibitionzone(mm)
Pseudomonas aeruginosa
Escherichia coli
Staphylococcus aureus
Bacillus subtilis
Fig. 2 Antimicrobial activity of the tested surfactants against
microbiofouling Gram-negative and Gram-positive bacteria (using
three repeated readings and Excel software)
532 J Surfact Deterg (2015) 18:529–535
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several layers of peptidoglycan and molecules of tei-
choic acid that are perpendicular to the peptidoglycan
sheets, it is probable that the positive charge of the qua-
ternary hexammonium compounds causes the simple
adsorption to the cell wall surface via electrostatic inter-
action between the N?
group of the surfactant and the
COO-
of teichoic acid. Accordingly, carboxypeptidase
enzyme was blocked and caused destruction by increasing
the permeability or ‘‘leakiness’’ of the lipid cell membrane.
The blocking of carboxypeptidase enzymes also blocks cell
wall synthesis [27]. The number of alkyl groups is another
important factor affecting the surfactant performance. As a
result, the antimicrobial activities of the prepared surfac-
tants decreased as the number of alkyl groups increased as
follows: Ah [ Dh [ Ch [ Bh. This may be attributed to
the increase in the molecules’ lipophilicity as a result of the
presence of more hydrophobic chains; this increases the
time for attacking of the cell wall by N?
(hindrance effect)
and crossing it to the cell membrane (see Scheme 1 in
supplementary information) [26]. From the data illustrated
in Fig. 2, it is clear that the Gram-negative bacteria are
more resistant to the prepared surfactants than Gram-posi-
tive bacteria. The results show that P. aeruginosa exhibited
the minimum antibacterial activity compared to other
Gram-positive bacteria strains. This may be attributed to the
effect of bacterial cell wall structure (double membrane
structure). As a result of the presence of the outer mem-
brane, the adsorption of QACs on the cytoplasm membranes
will be decreased [12].
MIC Values
It is well known that the lower MIC values of the tested
surfactants give the higher antimicrobial activity [28]. The
MICs of Ah for P. aeruginosa and E. coli (Gram negative)
and S. aureus and B. subtilis (Gram positive) strains are
shown in Table S2 (in supplementary information). Results
show that the MIC value of Bh is the most effective
compound against both E. coli (0.75 mg/l) and P. aeru-
ginosa (0.75 mg/l) comparing with the other tested sur-
factants. On the other hand, it is noticed that Ah have the
lowest MIC value of 0.37 and 0.75 mg/l for S. aureus and
B. subtilis, respectively. The obtained results from the
measurements of biological activity are in a good agree-
ment and consistent with these obtained by MICs values
for all tested surfactants.
Surface Active and Thermodynamic Properties
of the Prepared Cationic Surfactants
The surface properties of the prepared surfactants including
the cmc, the values of surface tension at the cmc (ccmc), the
maximum surface pressure (pcmc), the maximum surface
excess concentration at surface saturation ‘‘effectiveness’’
(Ccmc), and the minimum surface area per surfactant mole-
cule (Acmc) are listed in Table 1 and illustrated in Fig. 3.
From the obtained results, it is obvious that the surface ten-
sion (ccmc) was decreased of 37, 39, and 41 mNm-1
for Ah,
Dh, and Ch, respectively by increasing the ethyl group. This
refers to increasing the hydrophobicity of molecules [29].
Regarding the surface parameters and antimicrobial activity
listed in Table 1 and Fig. 2, it was found that compound Ah
possessed the lowest surface tension (ccmc) of 37 mNm-1
as
well as the highest antimicrobial activity towards S. aureus
bacteria compared with Dh and Ch surfactants. This could be
explained because Ah surfactant contains three quaternary
hexammonium groups reflecting its high lipophilicity that
facilitates its penetration into the Gram-positive bacteria cell
wall by adsorption of N?
onto the negatively charged
receptors of the bacterial cell wall. Also, from Table 1 and
Fig. 2, it was found that the lowest surface tension (ccmc) of
35 mN m-1
and the minimum antimicrobial activity were
obtained with Bh in comparison with Ch, Dh, and Ah sur-
factants against S. aureus. Increasing the length of the
hydrophobic group in Bh leads to a decrease in the solubility
of the surfactant in water. Meanwhile, the surfactants mol-
ecules at the interface become more close each to other (on
parole the area occupied by hydrophilic group at the interface
allow it), which in turn leads to disruption of the absorption
of the surfactant on the surface [30]. Accordingly, an
increase in the alkyl chain length (hexyl group) followed by
an increase in the hydrophobic interaction, which in turn
‘‘sucks’’ the molecule further into the membrane, is followed
by growing destabilization of membrane fluid and hence
decreases the concentration that destroys the cell. Concern-
ing the more resistant Gram-negative bacteria which have
very thick cell membranes, compound Bh showed the
highest antibacterial activity. Compound (Bh) has the lowest
cmc, 0.977 9 10-3
mol dm-3
, indicating its highest surface
activity that might facilitate its penetration through the
bacterial cell membrane, which results in increasing the
repulsion between the polar atom (N?
) of Bh and the non-
polar cell wall of the tested bacteria so that the molecules
tend to aggregate via the alkyl chain (Bh has the bulkiest
alkyl chain) on the cell wall surface at low concentration
[31]. Accordingly, the high resistance of Gram-negative
bacteria might reflect their abilities to minimize the antimi-
crobial activities of the tested compounds. Generally, the
accumulation of the surfactants at the interface was descri-
bed by minimum surface excess (Cmax) values. The data in
Table 1 shows that a decrease of the hydrophilic moiety of
the surfactant molecules decreases the Cmax. Therefore, the
surface excess concentration of the prepared cationic sur-
factants was decreased by decreasing the hydrophilic group.
This means that the possibility of the surfactant becoming
more soluble in water would be decreased. As a result of the
J Surfact Deterg (2015) 18:529–535 533
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decreasing of the Cmax values, the area at the interface for
each surfactant molecule will be increased [30]. The mini-
mum surface area occupied by each surfactant molecule at
the air–water interface (Amin) was calculated and was
affected by the presence of the polar and/or charged groups
[30]. Also (for cationic surfactants), the competition between
van der Waals forces among aliphatic chains and repulsive
interactions (electrostatic or hydration) between polar head
groups impacts on the resulting value of Amin [32]. That is the
reason for the lower Amin value of Bh compared to those of
Ah, Dh, and Ch. The standard free energies of micellization
(DGmic) and adsorption (DGad) of the synthesized surfactants
were calculated and the results are listed in Table 1. From the
obtained data of DGmic, it can be concluded that the micel-
lization process is spontaneous because DGmic  0. Gener-
ally, DGad is lower than DGmic values. This indicates that
these surfactants favor adsorption more than micellization.
Obviously, this favorability of adsorption is attributed to
interaction forces between hydrophobic chains and the polar
medium and that are minimum value the surfactant
molecules are situated at the air/water interface. Thus,
the maximum -DGad (-20.33 kJ/mol) was obtained by
(Ah) that exhibited the maximum inhibition efficiency for
Gram-positive bacteria.
Conclusion
Four cationic surfactants (Ah, Dh, Ch, and Bh) were syn-
thesized and their antimicrobial activity against two strains
of Gram-negative and two strains of Gram-positive bacte-
ria were studied. The antimicrobial activity was found to
increase with increasing the hydrophilic group of the pre-
pared surfactants Ah, Dh, and Ch towards Gram-positive,
whereas the most effective parameter affecting the activity
of the surfactant Bh against Gram-negative bacteria is the
chain length of the cationic surfactant. The results also
show that the surface tension of the surfactants has a sig-
nificant effect on the antimicrobial activity for Gram-neg-
ative and Gram-positive bacteria.
References
1. Yebra DM, Kiil S, Dam JK (2004) Antifouling technology—past,
present and future steps towards efficient and environmentally
friendly antifouling coatings. Prog Org Coat 50:75–104
2. Goncharov VI, Smolin VN (2007) Biofouling of equipment in
waste treatment systems. Chem Technol Fuels Oils 43:252–253
3. Lee AK, Newman DK (2003) Microbial iron respiration: impacts
on corrosion processes. Appl Microbiol Biotechnol 62:134–139
4. Jass J, Walker JT (2000) Biofilms and biofouling. In: Walker JT,
Surman S, Jass J (eds) Industrial biofouling: detection, prevention
and control. Wiley, New York, pp 1–12
5. Cloete TE, Jacobs L, Brozel VS (1998) The chemical control of
biofouling in industrial water systems. Biodegradation 9:23–37
6. Shirai A, Sumitomo T, Kurimoto M, Maseda H, Kourai H (2009)
The mode of the antifungal activity of gemini-pyridinium salt
against yeast. Biocontrol Sci 14:13–20
7. Hoque J, Akkapeddi P, Yarlagadda V, Uppu DS, Kumar P,
Haldar J (2012) Cleavable cationic antibacterial amphiphiles:
synthesis, mechanism of action, and cytotoxicities. Langmuir
28:12225–12234
8. McCarron PA, Donnelly RF, Marouf W, Calvert DE (2007) Anti-
adherent and antifungal activities of surfactant-coated poly(eth-
ylcyanoacrylate) nanoparticles. Int J Pharm 340:182–190
9. Domagk G (1935) Dtsch Med Wochenschr 24:829–832
10. Klarmann W (1946) Soap Sanit Chemicals 22:125
11. Brunt KD (1987) In: Hill HC (ed) Biocides for the oil industry.
Wiley, New York, pp 201–207
Table 1 Surface active properties and thermodynamic parameters of the synthesized cationic surfactants
Surfactant Cmca
(mol dm-3
910-3
)
ccmc
a
(mN m-1
)
pcmc
b
(mNm-1
)
Cmax
b
(mol/cm-2
9 1010
)
Amin
b
(nm2
/molecule)
DGmic
b
(kJ/mol)
DGad
b
(kJ/mol)
Ah 1.01 37 35 1.03 160.68 -16.94 -20.33
Dh 1.43 39 33 1.06 156.40 -16.22 -19.33
Ch 2.15 41 31 1.09 151.79 -15.21 -18.00
Bh 0.977 35 37 1.11 149 -17.17 -20.49
a
Values reflect the precision of the tensiometer
b
Values reflect the precision of the Excel software
30
35
40
45
50
55
60
65
-14-12-10-8-6-4-2
ln c, mol dm-3
γ,mNm-1
Ah
Dh
Ch
Bh
Fig. 3 c–ln C adsorption isotherm for prepared cationic surfactants
(using three repeated readings and Excel software)
534 J Surfact Deterg (2015) 18:529–535
123
Author's personal copy
12. Rozga-Wijas K, Mizerska U, Fortuniak W, Chojnowski J, Hałasa
R, Werel W (2007) Quaternary ammonium salts (QAS) modified
polysiloxane biocide supported on silica materials. J Inorg Or-
ganomet Polym 17:605–613
13. Dizman B, Elasri MO, Mathias LJ (2006) Synthesis and anti-
bacterial activities of water-soluble methacrylate polymers con-
taining quaternary ammonium compounds. J Polym Sci Part A
Polym Chem 44:5965–5973
14. Kugler R, Boulossa O, Rondelez F (2005) Evidence of a charge-
density threshold for optimum efficiency of biocidal cationic
surfaces. Microbiol 151:1341–1348
15. Arnt L, Nusslein K, Tew GN (2004) Nonhemolytic abiogenic
polymers as antimicrobial peptide mimics. J Polym Sci Part A
Polym Chem 48:3860–3864
16. Gabrielska J, Sarapuk J, Przestalski S, Wroclaw P (1994) Tenside
Surfact Deterg 31:296
17. Kawabata N, Nishiguchi M (1988) Antibacterial activity of sol-
uble pyridinium-type polymers. Appl Environ Microbiol
54:2532–2535
18. Caillier L, de Givenchy ET, Levy R, Vandenberghe Y, Ge´ribaldi
S, Guittard F (2009) Synthesis and antimicrobial properties of
polymerizable quaternary ammoniums. Eur J Med Chem
44:3201–3208
19. Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken HR
(1995) Manual of clinical microbiology, 6th edn. ASM Press,
Washington, pp 15–18
20. Olurinola PF (1996) A laboratory manual of pharmaceutical
microbiology. Idu, Abuja, pp 69–105
21. Kaya O, Akc¸am F, Yaylı G (2012) Investigation of the in vitro
activities of various antibiotics against Brucella melitensis
strains. Turk J Med Sci 42:145–148
22. Noor El-Din MR, Al-Sabagh AM, Hegazy MA (2012) Study of
the inhibition efficiency for some novel surfactants on the carbon
steel (Type H-11) pipelines in 0.5 M HCl solution by potentio-
dynamic technique. J Dispersion Sci Technol 33:1444–1451
23. Sayem Alam M, Asit BM (2012) Thermodynamic studies on
mixed micellization of amphiphilic drug amitriptyline hydro-
chloride and nonionic surfactant Triton X-100. J Mol Liq
168:75–79
24. Pavlikova-Moricka M, Lacko I, Devinsky F, Masarova L, Mily-
narcik D (1994) Quantitative relationships between structure and
antimicrobial activity of new ‘‘soft’’ bisquaternary ammonium
salts. J Folia Microbiol (Praha) 39:176–180
25. Nikaido H (1996) Outer membrane. In: Neidhardt FC (ed)
Escherichia coli and Salmonella typhimurium, cellular and
molecular biologym. American Society for Microbiology Press,
Washington, DC
26. Gao Y, van Belkum MJ, Stiles ME (1999) The outer membrane
of Gram negative bacteria inhibits antibacterial activity of bro-
chocin-C. Appl Environ Microbiol 65:4329–4333
27. Badawi AM, Hafiz AA (2007) Synthesis and immunomodulatory
activity of some novel amino acid germinates. J Iran Chem Soc
4:107–113
28. Argyropoulou I, Geronikaki A, Paola V, Zani F (2009) Synthesis
the biological evalution of sulfonamide thiazole and benzothia-
zole deriviatives as antimicrobial agents. Arkivoc 4:89–102
29. Santhakumar K, Kumaraguru N, Arumugham MN, Arunachalam
S (2006) Metallomicelles of Co(III) coordination complexes-
synthesis, characterization and determination of CMC values.
Polyhedron 25:1507–1513
30. Rosen MJ (2004) Surfactants and interfacial phenomena, 3rd edn.
Wiley, New York
31. Badawi AW, El-Bayouki KhA, Zakria VR (1985) Acetanilide
sulphonyl hydrazides and hadrazones of biological activity.
Oriental J Chem 1:78
32. Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd
edn. Wiley, New York
Rafat M. Mohareb is a professor of pharmaceutical organic
chemistry. He was awarded a Fulbright fellowship, USA in 1999,
and an Alexander von Humboldt fellowship, Germany, in 1987–1989.
His research interests include the synthesis and SAR of newly
synthesized heterocyclic compounds.
Abdelfatah M. Badawi is a professor of applied organic chemistry at
the Egyptian Petroleum Research Institute (Applied Surfactant
Laboratory) and is General Secretary for the International Society
of Therapeutic, Experimental and Clinical Research (Bastia, France).
He received his undergraduate training in chemistry at Cairo
University, Ph.D. in applied chemistry from Azhar University, and
D.Sc. degree in applied organic chemistry at Toronto University. He
has been a visiting professor at Arkansas University for Medical
Sciences (USA). He has participated in the research of applied
surfactant, metallosurfactant chemistry, and nanotechnology. His
research interests are in the areas of both environmental chemistry
and medicinal chemistry with special emphasis on antitumor agents.
His current research involves investigations on metal-based drugs.
Additional interests include the development of biocides and inves-
tigation of nanotechnology for destruction of both environmental
pollutants and tumors.
Mahmoud R. Noor El-Din received his Ph.D. from the Faculty of
Science, Ain Shams University, Cairo, Egypt. He is currently an
associate professor of applied organic chemistry at the Petroleum
Applications Department, Egyptian Petroleum Research Institute
(EPRI), Cairo, Egypt, with research interests in the synthesis of new
surfactants and their applications in petroleum industries. He is
working on the formulation of mini, micro, and nanoemulsions for
different applications. He has 10 years of experience as a researcher
in the Chemical Services and Development Centre (CSDC), EPRI,
Cairo, Egypt.
Nesreen A. Fatthalah received her Ph.D. from the Women’s College
for Science, Ain Shams University, Cairo, Egypt. She is currently a
researcher of marine environmental biotechnology, at the Petroleum
Biotechnology Lab, Processes Development Department, Egyptian
Petroleum Research Institute (EPRI), Cairo, Egypt, with research
interests in biofouling and biocorrosion and their control and
mitigation including biological, chemical, and paints and coatings
with green technology and their applications in petroleum industries.
She is working on biofouling control in heat exchangers using bio-
based nanocoating. She attended different workshops on plasma
applications in the coatings industry. She has 13 years of experience
as a biologist in the Petrochemicals Department, EPRI, Cairo, Egypt
and 5 years as an assistant researcher and 4 years as a researcher in
the Petroleum Biotechnology Lab, Processes Development Depart-
ment, EPRI, Cairo, Egypt.
J Surfact Deterg (2015) 18:529–535 535
123
Author's personal copy

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Synthesis and Characterization of Cationic Surfactants Based (1)

  • 1. 1 23 Journal of Surfactants and Detergents ISSN 1097-3958 Volume 18 Number 3 J Surfact Deterg (2015) 18:529-535 DOI 10.1007/s11743-014-1662-6 Synthesis and Characterization of Cationic Surfactants Based on N- Hexamethylenetetramine as Active Microfouling Agents Rafat M. Mohareb, Abdelfatah M. Badawi, Mahmoud R. Noor El- Din, Nesreen A. Fatthalah & Marian R. Mahrous
  • 2. 1 23 Your article is protected by copyright and all rights are held exclusively by AOCS. This e- offprint is for personal use only and shall not be self-archived in electronic repositories. If you wish to self-archive your article, please use the accepted manuscript version for posting on your own website. You may further deposit the accepted manuscript version in any repository, provided it is only made publicly available 12 months after official publication or later and provided acknowledgement is given to the original source of publication and a link is inserted to the published article on Springer's website. The link must be accompanied by the following text: "The final publication is available at link.springer.com”.
  • 3. ORIGINAL ARTICLE Synthesis and Characterization of Cationic Surfactants Based on N-Hexamethylenetetramine as Active Microfouling Agents Rafat M. Mohareb • Abdelfatah M. Badawi • Mahmoud R. Noor El-Din • Nesreen A. Fatthalah • Marian R. Mahrous Received: 16 January 2014 / Accepted: 10 December 2014 / Published online: 3 January 2015 Ó AOCS 2014 Abstract Four cationic surfactants of quaternary hex- ammonium silane chloride based on hexamethylenetetra- mine and alkyl chloride were synthesized. The chemical structures of the prepared cationic surfactants were eluci- dated using Fourier transform infrared (FT-IR) spectros- copy and mass spectrometry analysis. The surface and thermodynamic properties of the prepared surfactants were also studied. The performance of these cationic surfactants as microfouling agents against two strains of Gram-nega- tive bacteria, namely, Pseudomonas aeruginosa and Escherichia coli, and two strains of Gram-positive bacteria, namely, Staphylococcus aureus and Bacillus subtilis, were evaluated as antimicrobial agents. The results showed that the maximum antimicrobial activity was detected for N- hexamethylenetetramine-N-ethyl silane ammonium tri- chloride (Ah). The maximum and minimum antimicrobial activities were 73 and 60 % against S. aureus and E. coli, respectively, at a concentration of 5 mg/l, pH 7, and 37 °C. Keywords Microbial fouling Á Quaternary hexammonium silane Á Cationic surfactants Á Antimicrobial activity Introduction One of the most important problems facing the marine industries is biofouling, which affects underwater infra- structure components such as electrical cables, petroleum pipelines, fishing nets, etc. [1]. Microbes, bacteria, micro- algae, and higher microorganisms, e.g., aquatic fungi, infu- soria, rotifers, etc., live and multiply on the surfaces of pipelines immersed in water, refrigerators, and heat exchangers, inside flameless heating equipment in the pre- sence of aqueous media, and in systems for biochemical treatment of wastewaters. Heat and mass exchange worsen sharply, thermal power consumption increases, output and passability decrease, accidents occur in manufacturing units, and corrosion of metal surfaces intensifies as a result of biological fouling of this equipment [2]. Marine microor- ganisms like Escherichia sp., Staphylococcus sp., and Pseudomonas sp. are known to be effective in the biofouling process [3]. Moreover, Pseudomonas sp., the most prevalent in the water and seawater industries, have been implicated in the corrosion process of stainless and mild steels, and alu- minum alloys in marine habitats. In industrial settings of cooling-water towers, water pipelines, membrane unit, and food-processing plants, the unwanted biofilms of Staphylo- coccus aureus and Staphylococcus epidermidis are respon- sible for fouling [4]. The most widely practiced approach to the minimization of biofilms in industrial water systems is by way of chemical treatment focusing either on the reduction of microbial numbers using biocides, or their removal using either synthetic dispersants or enzymes [5]. Different types Electronic supplementary material The online version of this article (doi:10.1007/s11743-014-1662-6) contains supplementary material, which is available to authorized users. R. M. Mohareb Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt A. M. Badawi Á M. R. Noor El-Din (&) Á N. A. Fatthalah Egyptian Petroleum Research Institute, 1 Ahmed El- Zomor St., Nasr 11727, Cairo, Egypt e-mail: mrned04@yahoo.com M. R. Mahrous Science and Technology Center of Excellence, Cairo, Egypt 123 J Surfact Deterg (2015) 18:529–535 DOI 10.1007/s11743-014-1662-6 Author's personal copy
  • 4. of surfactants can act as antimicrobial agents by interaction with a microorganism’s cellular membranes [6, 7]. However, the surfactants are easily adsorbed at liquid–solid interfaces and can protect different surfaces from microorganism adhesion by forming protective coated surfaces [8]. The first use of cationic surfactants in the field of anti- bacterial resistance was recorded by Domagk in 1935 [9] and since that date, hundreds of new cationic surfactants have been synthesized and used as germicides and/or fungicides [10]. Alkyl pyridinium, alkyl trimethylammonium halides and hexamine derivatives, and 1-(3-chloroallyl)-3,5,7-triaza- 1-azoniaadamantane chloride are the most widely com- pounds used in the field of biofouling resistance [10, 11]. Also, quaternary ammonium compounds (QACs) are com- monly used as effective biocidal agents, as they have superior properties compared to known antibacterial agents such as better membrane penetration, excellent environmental sta- bility, lower toxicity, higher corrosion inhibition effect, and lower skin irritation [12–16]. QACs have a broad spectrum of antimicrobial activity against both Gram-positive and Gram- negative bacteria [17]. As QACs are positively charged cations, their mode of action is related to their attraction to negatively charged materials such as bacterial proteins [18]. The objective of the present work was to synthesize a new series of cationic silicon-based quaternary hexammonium surfactants for use as microfouling agents. These surfactants were prepared by condensing an amine (containing a triva- lent nitrogen) with alkyl silicon mono-, di-, and trichlorides. The efficiency of the prepared surfactants as microfouling agents against three strains of bacteria was investigated. In addition, the effect of surface and thermodynamic parameters on the efficiency of the synthesized surfactants was studied. Experimental Materials Analytical grades of hexamethylenetetramine, trichloroeth- ylsilane, trichlorohexylsilane, dichlorodiethylsilane, and chlorotriethylsilane were purchased from Sigma–Aldrich Co., UK. Technical grade dimethylformamide (DMF) was obtained from Fluka, Germany. Deionized water was uti- lized in all experiments. Method Synthesis of Quaternization of Hexamethylenetetramine A 0.1-mol sample of each silane, namely, trichlorohex- ylsilane, trichloroethylsilane, dichlorodiethylsilane, and chlorotrimethylsilane, was reacted with hexamethylenetet- ramine (0.3, 0.3, 0.2, and 0.1 mol, respectively; the number of moles of hexamethylenetetramine was chosen on the basis of the number of chlorine groups in the silane). At the beginning of each reaction, the hexamethylenetetramine was dissolved in 40 ml of hot DMF and then treated with the silane in a 500-ml flask fitted with a Dean-Stark trap equipped with a condenser and continuously stirred at 400 rpm for 8 h. The reaction mixture was cooled and filtrated. The precipitate was washed with acetone. The solvent was evaporated using an evaporator. Each of the prepared surfactant was washed twice with acetone and left in room temperature for drying until constant weight. The chemical structure of the synthesized quaternary hexam- monium chloride surfactants is shown Fig. 1. Chemical Conformation The chemical structures of the prepared surfactants were confirmed using Fourier transform infrared (FT-IR) spec- troscopy (Thermoscientific, Nicolet iS10 FT-IR, USA) and mass spectrometry analysis (Alpha Omega Technologies, Inc., Brielle, NJ). Evaluation of the Synthesized Surfactants as Microfouling Agents The antimicrobial activity of each of the synthesized cat- ionic surfactant, namely, N-hexamethylenetetramine-N- ethylsilane ammonium trichloride (Ah), N-hexamethy- lenetetramine-N-diethylsilane ammonium dichloride (Dh), N-hexamethylenetetramine-N-triethylsilane ammonium chloride (Ch), and N-hexamethylenetetramine-N-hexylsi- lane ammonium trichloride (Bh), was evaluated as a microfouling agent against four bacterial strains: Pseudo- monas aeruginosa ATCC 10145, Escherichia coli ATCC 23282 (Gram-negative bacteria), and Staphylococcus aureus ATCC 29737, Bacillus subtilis NCTC 10400 (Gram-positive bacteria) using both the agar well diffusion method and minimum inhibitory concentration (MIC) test [19, 20]. Agar Well Diffusion Method The agar well diffusion method depends on the diffusion of the prepared surfactants through a layer of solidified agar that inhibits the growth of the microorganism in an area or zone around the hole containing the antibiotic solution. In this assay, the size of the inhibition zone and the dose of the surfactants assayed are correlated. In this study, the antimicrobial susceptibility was tested on solid (agar–agar) media. The medium was inoculated with the tested microorganisms separately and poured into sterilized Petri dishes (20 ml/dish). The agar medium was punched using a 530 J Surfact Deterg (2015) 18:529–535 123 Author's personal copy
  • 5. sterile cork borer to make five holes of 10 mm. For each surfactant, a stock solution was prepared at a concentration of 5 mg/ml. About 100 ll of each stock solution was added using a sterile micropipette into four holes and allowed to diffuse at 4 °C for 2 h and then incubated at 37 °C for 24 h. The fifth hole was filled with control solution (which has no surfactant). The negative control was DMF that showed no antimicrobial activity against the tested microorganisms. The diameter of the inhibition zone (millimeters) was measured. The previously step was repeated twice for each surfactant and the average values were recorded [20]. Minimum Inhibitory Concentration (MIC) Test In microbiology, MIC is defined as the lowest concentra- tion of an antimicrobial that inhibits the visible growth of a microorganism after overnight incubation [21]. Serial dilutions of the four tested compounds were prepared in macrodilution tubes at a range of concentrations (dilution N N N N RSiCl(x) Hexamethylenetetramine (C6H12N4) where R=2 or 3 molecules of ethyl group R =1 molecule of ethyl or hexyl group x=1, 2 or 3 Si Cl Si N4C6H12 C2H5 Cl Si R C2H5 C2H5C2H5 C2H5 or R SiCl(x) N-hexamethylene tetramine -N- diethyl silane ammonium dichloride (Dh) N-hexamethylene tetramine-N- triethyl silane ammonium chloride (Ch) N-hexamethylene tetramine -N-alkylsilane ammonium trichloride (Ah and/or Bh) Alkyl silicon chloride +2 -2 +1 -1 N4C6H12 N4C6H12 +3 Cl -3 N4C6H12 N4C6H12 H12C6N4 Fig. 1 Chemical structure of the synthesized quaternary hexammonium chloride surfactants J Surfact Deterg (2015) 18:529–535 531 123 Author's personal copy
  • 6. factor ranging from 1/2 to 1/64). Bacterial suspensions were adjusted to the logarithmic growth phase to match the turbidity of a 0.5 McFarland standard, yielding approxi- mately 108 CFU/ml. The same amounts of bacteria were added to all tubes and the tubes were incubated at 37 °C for 24 h. Each tube was examined for growth and compared to the control. Bacterial suspension added to a tube filled with nutrient broth without each of the tested compounds was used as a positive growth control. A tube not containing nutrient broth was used as a negative growth control. The absence of growth was defined as antibacterial activity. Surface Tension Measurements (c) The surface tension (c) of the prepared cationic surfactants at 25 °C was measured using a Du Nou¨y tensiometer (Kruss-K6 type) by applying the platinum ring technique. The surface tension of each surfactant was measured three times within a 3-min interval between each reading [22]. The critical micelle concentration (cmc) was determined from the abrupt change in the slope of surface tension (ccmc) versus logarithm of the concentration curve (ln C). From the slope of a plot of c versus ln C, the maximum surface excess concentration (Cmax) and the minimum surface area per surfactant (Amin) were calculated. Also, the thermodynamics parameters of adsorption and micelliza- tion Gibbs free energies, such as Gibbs free energy of adsorption (DGads) and the Gibbs free energy of micelli- zation (DGmic), for the prepared surfactants were calculated by utilization of Gibb’s adsorption equations [23]. Results and Discussion Characterization of Quaternary Hexammonium Silane Compounds The prepared surfactants (Ah, Bh, Dh, and Ch) were characterized using both FT-IR spectroscopy and mass spectrometry analysis and the biological activities are discussed in the following section. FT-IR Spectroscopic and Mass Spectrum Analyses The structures of the prepared quaternary hexammonium silane chloride compounds (Ch and Ah) were elucidated by FT-IR. The FT-IR spectrum in Fig. S2 is dominated by a Si–N peak around 900 cm-1 , a Si–C peak at 1,010 cm-1 , and a C–N peak around 2,350 cm-1 . Figure S3 shows that the peak intensity at 900 cm-1 is larger in compounds with higher Si–N content and increases as the extent of hexa- methylenetetramine increases. This band indicates that more than one molecule of N-hexamethylenetetramine was introduced. Also, the decrease of the peak intensity at 1,010 cm-1 indicates that the prepared compound contains more than one ethyl group. The chemical structures of the quaternary hexammonium silane compounds were also confirmed by mass spectrometry (Fig. S2–S4; Table S1 in supplementary information). Biological Activity of the Synthesized Surfactants The synthesized compounds (Ah, Dh, Ch, and Bh) were evaluated for their microfouling action against P. aerugin- osa and E. coli as Gram-negative and S. aureus and B. subtilis as Gram-positive bacteria (Fig. 2). Commonly, Gram-negative bacteria are resistant towards antibacterial substances owing to the presence of lipopolysaccharide molecules in their outer membrane, acting as a barrier to the penetration of numerous antibiotic molecules which are related to the enzymes in the periplasmic space that are able to break down the molecules introduced from outside [24– 26]. By inspection of the data in Fig. 2, the efficiency of the prepared cationic surfactants is in the order Bh [ Ch = Dh [ Ah for E. coli, and Ah = Bh [ Ch = Dh for P. aeruginosa. Also, the maximum inhibition zone was afforded by Bh surfactant for both organisms. This may be attributed to the effect of the number of alkyl groups for Ah, Ch, and Dh and to the length of Bh surfactant on its adsorption onto the bacterial cell wall. However, the results show that Ch and Dh have lower inhibition (inhibition zone = 20 cm) efficiency against P. aeruginosa than that of Ah (inhibition zone = 24 cm) and this may be attributed to the number of alkyl groups. Also, the results show that Bh surfactant have a high inhibition zone (3.5 cm) comparing with Dh, Ch, and Ah; this may be attributed to the effect of alkyl group length. Regarding Gram-positive bacteria, the highest antimicrobial activity against S. aureus was affor- ded by Ah surfactant (Fig. 2). As a result of the structure of the cell wall of Gram-positive bacteria, which consists of 0 5 10 15 20 25 30 35 40 45 50 +ve control Ah Bh Ch Dh Surfactant Inhibitionzone(mm) Pseudomonas aeruginosa Escherichia coli Staphylococcus aureus Bacillus subtilis Fig. 2 Antimicrobial activity of the tested surfactants against microbiofouling Gram-negative and Gram-positive bacteria (using three repeated readings and Excel software) 532 J Surfact Deterg (2015) 18:529–535 123 Author's personal copy
  • 7. several layers of peptidoglycan and molecules of tei- choic acid that are perpendicular to the peptidoglycan sheets, it is probable that the positive charge of the qua- ternary hexammonium compounds causes the simple adsorption to the cell wall surface via electrostatic inter- action between the N? group of the surfactant and the COO- of teichoic acid. Accordingly, carboxypeptidase enzyme was blocked and caused destruction by increasing the permeability or ‘‘leakiness’’ of the lipid cell membrane. The blocking of carboxypeptidase enzymes also blocks cell wall synthesis [27]. The number of alkyl groups is another important factor affecting the surfactant performance. As a result, the antimicrobial activities of the prepared surfac- tants decreased as the number of alkyl groups increased as follows: Ah [ Dh [ Ch [ Bh. This may be attributed to the increase in the molecules’ lipophilicity as a result of the presence of more hydrophobic chains; this increases the time for attacking of the cell wall by N? (hindrance effect) and crossing it to the cell membrane (see Scheme 1 in supplementary information) [26]. From the data illustrated in Fig. 2, it is clear that the Gram-negative bacteria are more resistant to the prepared surfactants than Gram-posi- tive bacteria. The results show that P. aeruginosa exhibited the minimum antibacterial activity compared to other Gram-positive bacteria strains. This may be attributed to the effect of bacterial cell wall structure (double membrane structure). As a result of the presence of the outer mem- brane, the adsorption of QACs on the cytoplasm membranes will be decreased [12]. MIC Values It is well known that the lower MIC values of the tested surfactants give the higher antimicrobial activity [28]. The MICs of Ah for P. aeruginosa and E. coli (Gram negative) and S. aureus and B. subtilis (Gram positive) strains are shown in Table S2 (in supplementary information). Results show that the MIC value of Bh is the most effective compound against both E. coli (0.75 mg/l) and P. aeru- ginosa (0.75 mg/l) comparing with the other tested sur- factants. On the other hand, it is noticed that Ah have the lowest MIC value of 0.37 and 0.75 mg/l for S. aureus and B. subtilis, respectively. The obtained results from the measurements of biological activity are in a good agree- ment and consistent with these obtained by MICs values for all tested surfactants. Surface Active and Thermodynamic Properties of the Prepared Cationic Surfactants The surface properties of the prepared surfactants including the cmc, the values of surface tension at the cmc (ccmc), the maximum surface pressure (pcmc), the maximum surface excess concentration at surface saturation ‘‘effectiveness’’ (Ccmc), and the minimum surface area per surfactant mole- cule (Acmc) are listed in Table 1 and illustrated in Fig. 3. From the obtained results, it is obvious that the surface ten- sion (ccmc) was decreased of 37, 39, and 41 mNm-1 for Ah, Dh, and Ch, respectively by increasing the ethyl group. This refers to increasing the hydrophobicity of molecules [29]. Regarding the surface parameters and antimicrobial activity listed in Table 1 and Fig. 2, it was found that compound Ah possessed the lowest surface tension (ccmc) of 37 mNm-1 as well as the highest antimicrobial activity towards S. aureus bacteria compared with Dh and Ch surfactants. This could be explained because Ah surfactant contains three quaternary hexammonium groups reflecting its high lipophilicity that facilitates its penetration into the Gram-positive bacteria cell wall by adsorption of N? onto the negatively charged receptors of the bacterial cell wall. Also, from Table 1 and Fig. 2, it was found that the lowest surface tension (ccmc) of 35 mN m-1 and the minimum antimicrobial activity were obtained with Bh in comparison with Ch, Dh, and Ah sur- factants against S. aureus. Increasing the length of the hydrophobic group in Bh leads to a decrease in the solubility of the surfactant in water. Meanwhile, the surfactants mol- ecules at the interface become more close each to other (on parole the area occupied by hydrophilic group at the interface allow it), which in turn leads to disruption of the absorption of the surfactant on the surface [30]. Accordingly, an increase in the alkyl chain length (hexyl group) followed by an increase in the hydrophobic interaction, which in turn ‘‘sucks’’ the molecule further into the membrane, is followed by growing destabilization of membrane fluid and hence decreases the concentration that destroys the cell. Concern- ing the more resistant Gram-negative bacteria which have very thick cell membranes, compound Bh showed the highest antibacterial activity. Compound (Bh) has the lowest cmc, 0.977 9 10-3 mol dm-3 , indicating its highest surface activity that might facilitate its penetration through the bacterial cell membrane, which results in increasing the repulsion between the polar atom (N? ) of Bh and the non- polar cell wall of the tested bacteria so that the molecules tend to aggregate via the alkyl chain (Bh has the bulkiest alkyl chain) on the cell wall surface at low concentration [31]. Accordingly, the high resistance of Gram-negative bacteria might reflect their abilities to minimize the antimi- crobial activities of the tested compounds. Generally, the accumulation of the surfactants at the interface was descri- bed by minimum surface excess (Cmax) values. The data in Table 1 shows that a decrease of the hydrophilic moiety of the surfactant molecules decreases the Cmax. Therefore, the surface excess concentration of the prepared cationic sur- factants was decreased by decreasing the hydrophilic group. This means that the possibility of the surfactant becoming more soluble in water would be decreased. As a result of the J Surfact Deterg (2015) 18:529–535 533 123 Author's personal copy
  • 8. decreasing of the Cmax values, the area at the interface for each surfactant molecule will be increased [30]. The mini- mum surface area occupied by each surfactant molecule at the air–water interface (Amin) was calculated and was affected by the presence of the polar and/or charged groups [30]. Also (for cationic surfactants), the competition between van der Waals forces among aliphatic chains and repulsive interactions (electrostatic or hydration) between polar head groups impacts on the resulting value of Amin [32]. That is the reason for the lower Amin value of Bh compared to those of Ah, Dh, and Ch. The standard free energies of micellization (DGmic) and adsorption (DGad) of the synthesized surfactants were calculated and the results are listed in Table 1. From the obtained data of DGmic, it can be concluded that the micel- lization process is spontaneous because DGmic 0. Gener- ally, DGad is lower than DGmic values. This indicates that these surfactants favor adsorption more than micellization. Obviously, this favorability of adsorption is attributed to interaction forces between hydrophobic chains and the polar medium and that are minimum value the surfactant molecules are situated at the air/water interface. Thus, the maximum -DGad (-20.33 kJ/mol) was obtained by (Ah) that exhibited the maximum inhibition efficiency for Gram-positive bacteria. Conclusion Four cationic surfactants (Ah, Dh, Ch, and Bh) were syn- thesized and their antimicrobial activity against two strains of Gram-negative and two strains of Gram-positive bacte- ria were studied. The antimicrobial activity was found to increase with increasing the hydrophilic group of the pre- pared surfactants Ah, Dh, and Ch towards Gram-positive, whereas the most effective parameter affecting the activity of the surfactant Bh against Gram-negative bacteria is the chain length of the cationic surfactant. The results also show that the surface tension of the surfactants has a sig- nificant effect on the antimicrobial activity for Gram-neg- ative and Gram-positive bacteria. References 1. Yebra DM, Kiil S, Dam JK (2004) Antifouling technology—past, present and future steps towards efficient and environmentally friendly antifouling coatings. Prog Org Coat 50:75–104 2. Goncharov VI, Smolin VN (2007) Biofouling of equipment in waste treatment systems. Chem Technol Fuels Oils 43:252–253 3. Lee AK, Newman DK (2003) Microbial iron respiration: impacts on corrosion processes. Appl Microbiol Biotechnol 62:134–139 4. Jass J, Walker JT (2000) Biofilms and biofouling. In: Walker JT, Surman S, Jass J (eds) Industrial biofouling: detection, prevention and control. Wiley, New York, pp 1–12 5. Cloete TE, Jacobs L, Brozel VS (1998) The chemical control of biofouling in industrial water systems. Biodegradation 9:23–37 6. Shirai A, Sumitomo T, Kurimoto M, Maseda H, Kourai H (2009) The mode of the antifungal activity of gemini-pyridinium salt against yeast. Biocontrol Sci 14:13–20 7. Hoque J, Akkapeddi P, Yarlagadda V, Uppu DS, Kumar P, Haldar J (2012) Cleavable cationic antibacterial amphiphiles: synthesis, mechanism of action, and cytotoxicities. Langmuir 28:12225–12234 8. McCarron PA, Donnelly RF, Marouf W, Calvert DE (2007) Anti- adherent and antifungal activities of surfactant-coated poly(eth- ylcyanoacrylate) nanoparticles. Int J Pharm 340:182–190 9. Domagk G (1935) Dtsch Med Wochenschr 24:829–832 10. Klarmann W (1946) Soap Sanit Chemicals 22:125 11. Brunt KD (1987) In: Hill HC (ed) Biocides for the oil industry. Wiley, New York, pp 201–207 Table 1 Surface active properties and thermodynamic parameters of the synthesized cationic surfactants Surfactant Cmca (mol dm-3 910-3 ) ccmc a (mN m-1 ) pcmc b (mNm-1 ) Cmax b (mol/cm-2 9 1010 ) Amin b (nm2 /molecule) DGmic b (kJ/mol) DGad b (kJ/mol) Ah 1.01 37 35 1.03 160.68 -16.94 -20.33 Dh 1.43 39 33 1.06 156.40 -16.22 -19.33 Ch 2.15 41 31 1.09 151.79 -15.21 -18.00 Bh 0.977 35 37 1.11 149 -17.17 -20.49 a Values reflect the precision of the tensiometer b Values reflect the precision of the Excel software 30 35 40 45 50 55 60 65 -14-12-10-8-6-4-2 ln c, mol dm-3 γ,mNm-1 Ah Dh Ch Bh Fig. 3 c–ln C adsorption isotherm for prepared cationic surfactants (using three repeated readings and Excel software) 534 J Surfact Deterg (2015) 18:529–535 123 Author's personal copy
  • 9. 12. Rozga-Wijas K, Mizerska U, Fortuniak W, Chojnowski J, Hałasa R, Werel W (2007) Quaternary ammonium salts (QAS) modified polysiloxane biocide supported on silica materials. J Inorg Or- ganomet Polym 17:605–613 13. Dizman B, Elasri MO, Mathias LJ (2006) Synthesis and anti- bacterial activities of water-soluble methacrylate polymers con- taining quaternary ammonium compounds. J Polym Sci Part A Polym Chem 44:5965–5973 14. Kugler R, Boulossa O, Rondelez F (2005) Evidence of a charge- density threshold for optimum efficiency of biocidal cationic surfaces. Microbiol 151:1341–1348 15. Arnt L, Nusslein K, Tew GN (2004) Nonhemolytic abiogenic polymers as antimicrobial peptide mimics. J Polym Sci Part A Polym Chem 48:3860–3864 16. Gabrielska J, Sarapuk J, Przestalski S, Wroclaw P (1994) Tenside Surfact Deterg 31:296 17. Kawabata N, Nishiguchi M (1988) Antibacterial activity of sol- uble pyridinium-type polymers. Appl Environ Microbiol 54:2532–2535 18. Caillier L, de Givenchy ET, Levy R, Vandenberghe Y, Ge´ribaldi S, Guittard F (2009) Synthesis and antimicrobial properties of polymerizable quaternary ammoniums. Eur J Med Chem 44:3201–3208 19. Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken HR (1995) Manual of clinical microbiology, 6th edn. ASM Press, Washington, pp 15–18 20. Olurinola PF (1996) A laboratory manual of pharmaceutical microbiology. Idu, Abuja, pp 69–105 21. Kaya O, Akc¸am F, Yaylı G (2012) Investigation of the in vitro activities of various antibiotics against Brucella melitensis strains. Turk J Med Sci 42:145–148 22. Noor El-Din MR, Al-Sabagh AM, Hegazy MA (2012) Study of the inhibition efficiency for some novel surfactants on the carbon steel (Type H-11) pipelines in 0.5 M HCl solution by potentio- dynamic technique. J Dispersion Sci Technol 33:1444–1451 23. Sayem Alam M, Asit BM (2012) Thermodynamic studies on mixed micellization of amphiphilic drug amitriptyline hydro- chloride and nonionic surfactant Triton X-100. J Mol Liq 168:75–79 24. Pavlikova-Moricka M, Lacko I, Devinsky F, Masarova L, Mily- narcik D (1994) Quantitative relationships between structure and antimicrobial activity of new ‘‘soft’’ bisquaternary ammonium salts. J Folia Microbiol (Praha) 39:176–180 25. Nikaido H (1996) Outer membrane. In: Neidhardt FC (ed) Escherichia coli and Salmonella typhimurium, cellular and molecular biologym. American Society for Microbiology Press, Washington, DC 26. Gao Y, van Belkum MJ, Stiles ME (1999) The outer membrane of Gram negative bacteria inhibits antibacterial activity of bro- chocin-C. Appl Environ Microbiol 65:4329–4333 27. Badawi AM, Hafiz AA (2007) Synthesis and immunomodulatory activity of some novel amino acid germinates. J Iran Chem Soc 4:107–113 28. Argyropoulou I, Geronikaki A, Paola V, Zani F (2009) Synthesis the biological evalution of sulfonamide thiazole and benzothia- zole deriviatives as antimicrobial agents. Arkivoc 4:89–102 29. Santhakumar K, Kumaraguru N, Arumugham MN, Arunachalam S (2006) Metallomicelles of Co(III) coordination complexes- synthesis, characterization and determination of CMC values. Polyhedron 25:1507–1513 30. Rosen MJ (2004) Surfactants and interfacial phenomena, 3rd edn. Wiley, New York 31. Badawi AW, El-Bayouki KhA, Zakria VR (1985) Acetanilide sulphonyl hydrazides and hadrazones of biological activity. Oriental J Chem 1:78 32. Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd edn. Wiley, New York Rafat M. Mohareb is a professor of pharmaceutical organic chemistry. He was awarded a Fulbright fellowship, USA in 1999, and an Alexander von Humboldt fellowship, Germany, in 1987–1989. His research interests include the synthesis and SAR of newly synthesized heterocyclic compounds. Abdelfatah M. Badawi is a professor of applied organic chemistry at the Egyptian Petroleum Research Institute (Applied Surfactant Laboratory) and is General Secretary for the International Society of Therapeutic, Experimental and Clinical Research (Bastia, France). He received his undergraduate training in chemistry at Cairo University, Ph.D. in applied chemistry from Azhar University, and D.Sc. degree in applied organic chemistry at Toronto University. He has been a visiting professor at Arkansas University for Medical Sciences (USA). He has participated in the research of applied surfactant, metallosurfactant chemistry, and nanotechnology. His research interests are in the areas of both environmental chemistry and medicinal chemistry with special emphasis on antitumor agents. His current research involves investigations on metal-based drugs. Additional interests include the development of biocides and inves- tigation of nanotechnology for destruction of both environmental pollutants and tumors. Mahmoud R. Noor El-Din received his Ph.D. from the Faculty of Science, Ain Shams University, Cairo, Egypt. He is currently an associate professor of applied organic chemistry at the Petroleum Applications Department, Egyptian Petroleum Research Institute (EPRI), Cairo, Egypt, with research interests in the synthesis of new surfactants and their applications in petroleum industries. He is working on the formulation of mini, micro, and nanoemulsions for different applications. He has 10 years of experience as a researcher in the Chemical Services and Development Centre (CSDC), EPRI, Cairo, Egypt. Nesreen A. Fatthalah received her Ph.D. from the Women’s College for Science, Ain Shams University, Cairo, Egypt. She is currently a researcher of marine environmental biotechnology, at the Petroleum Biotechnology Lab, Processes Development Department, Egyptian Petroleum Research Institute (EPRI), Cairo, Egypt, with research interests in biofouling and biocorrosion and their control and mitigation including biological, chemical, and paints and coatings with green technology and their applications in petroleum industries. She is working on biofouling control in heat exchangers using bio- based nanocoating. She attended different workshops on plasma applications in the coatings industry. She has 13 years of experience as a biologist in the Petrochemicals Department, EPRI, Cairo, Egypt and 5 years as an assistant researcher and 4 years as a researcher in the Petroleum Biotechnology Lab, Processes Development Depart- ment, EPRI, Cairo, Egypt. J Surfact Deterg (2015) 18:529–535 535 123 Author's personal copy