Synthesis and some surface properties of glycine-based surfactants

Article abstract of DOI:10.1007/s11743-010-1210-y

A new group of anionic surfactants, namely sodium salts of secondary alkanesulfonamidoacetic acid, were synthesized using n-alkanesulfonyl chlorides as starting materials. These surfactants, having the formula: R-SO ₂-NH-CH₂-COONa, with R = C₁₂, C₁₄, C₁₆ and C₁₈, were obtained in a simple way with quantitative yields. Different chain lengths and positional isomers of this new type of surfactants are expected to present differences in surface properties and foamability. The surface properties including critical micelle concentrations and minimal surface tensions γ_min were determined for each prepared surfactant using surface tension measurements with a Wilhelmy plate. Surface excess and minimum area per molecule at the air-water interface were determined for different concentrations at 25 and 50 °C using the Gibbs equation. The foaming power was also determined by the Bartsch method, and the results obtained were compared to those of a commercial surfactant, the linear alkylbenzenesulfonate. The stability of the foam formed was also evaluated. As expected, these surfactants exhibit good surface properties and show good foaming power.

Full text of DOI:10.1007/s11743-010-1210-y

J Surfact Deterg (2011) 14:65–72
DOI 10.1007/s11743-010-1210-y
ORIGINAL ARTICLE
Synthesis and Some Surface Properties of Glycine-Based
Surfactants
Radia Mousli Amel Tazerouti
•
Received: 11 November 2009 / Accepted: 19 April 2010 / Published online: 23 May 2010
Ó AOCS 2010
Abstract A new group of anionic surfactants, namely
sodium salts of secondary alkanesulfonamidoacetic acid,
were synthesized using n-alkanesulfonyl chlorides as
starting materials. These surfactants, having the formula:
R–SO –NH–CH –COONa, with R = C , C , C and
Abbreviations
LAS
CMC
IR
Linear alkylbenzenesulfonates
Critical micelle concentration
Infrared spectroscopy
C
Surface excess
2
2
12
14
16
C , were obtained in a simple way with quantitative
8
Amin
SAS
SDS
Minimum area per molecule
Secondary alkanesulfonates
Sodium dodecyl sulfate
1
yields. Different chain lengths and positional isomers of
this new type of surfactants are expected to present dif-
ferences in surface properties and foamability. The surface
properties including critical micelle concentrations and
minimal surface tensions cmin were determined for each
prepared surfactant using surface tension measurements
with a Wilhelmy plate. Surface excess and minimum area
per molecule at the air–water interface were determined for
different concentrations at 25 and 50 °C using the Gibbs
equation. The foaming power was also determined by the
Bartsch method, and the results obtained were compared to
those of a commercial surfactant, the linear alkylbenzene-
sulfonate. The stability of the foam formed was also
evaluated. As expected, these surfactants exhibit good
surface properties and show good foaming power.
GC–MS Gas chromatography coupled to mass
spectrometry
EI
Electronic impact
PCI
NCI
Positive chemical ionization
Negative chemical ionization
Introduction
It is known that the combination of polar amino acids
(
(
hydrophilic moiety) and non-polar, long-chain compounds
hydrophobic moiety) for building up the amphiphilic
structure has produced molecules with high surface activity
and rapid biodegradation [1]. Anionic surfactants of the
carboxylate group are recommended as detergents, emul-
sifiers, wetting agents, and antistatic agents. Their ability to
inhibit corrosion is related to their adsorption through the
carboxyl radicals [2] and are also used as lubricants [3].
According to the literature [4], the reactions of the primary
isomer of sulfonamide with chlorinated aliphatic acids,
particularly with sodium acetate chloride, allow the prep-
aration of sodium salts of alkanesulfonamidoacetic acid.
The primary isomer of sodium salt of alkanesulfonamido-
acetic acid is described in the literature as an excellent
emulsifying agent for oils and waxes, giving stable
Keywords Alkanesulfonamidoacetic acid surfactants ꢀ
Surface tension ꢀ Critical micelle concentration ꢀ
Foam power ꢀ Foam stability
R. Mousli ꢀ A. Tazerouti (&)
Laboratory of Applied Organic Chemistry, Faculty of Chemistry,
University of Sciences and Technology Houari Boum e´ di e` ne
(USTHB), BP 32 El Alia, Bab Ezzouar, 16111 Algiers, Algeria
e-mail: ameltazerouti@gmail.com
R. Mousli
Centre de Recherche Scientifique et Technique en Analyses
Physico-Chimiques, BP 248, Algiers 16004, Algeria
1
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J Surfact Deterg (2011) 14:65–72
emulsions in hard water. It possesses a great specific affinity
for metal surfaces, and inhibits corrosion [5]. It is particu-
larly useful, also in the preparation of the lubricating
emulsions used for the drawing of wire from steel and the
non-ferrous metals [6], and as flotation agents [7]. To avoid
several steps, e.g., to prepare the sulfonamide RSO NH , its
[99% pure). The alkanesulfonyl chlorides were then
derivatized into the corresponding sulfonamides with N,N-
diethylamine using Berthold method, and then analysed by
GC–MS using EI mode, PCI and NCI mode. The gas
chromatograph, a Hewlett-Packard Model 6890 was cou-
pled to a Hewlett-Packard Model 5973 mass spectrometer.
The column used was HP5 MS, a poly (5% diphenyl/95%
dimethylsiloxane) capillary column 30 m 9 0.25 mm I.D.,
0.25 lm film thickness (Hewlett-Packard). The N,N-di-
ethylsulfonamide derivatives can either be detected by EI
(70 eV) or by chemical ionization (CI) techniques. The ion
source was run under positive (PCI) and negative (NCI)
conditions using methane as reagent gas. All other chem-
icals were of commercial origin (Fluka), and were used
without further purification. Distilled water was used for
preparing solutions.
2
2
sodium salt, and then to react it with sodium acetate chloride,
we reported in a previous paper the synthesis of dodecane-
sulfonamides in only one step using an amino acid [8]. As an
extension of these studies, we present here the synthesis of a
new series of sulfonamide surfactants, using alkanesulfonyl
chlorides RSO Cl as starting materials obtained by photo-
2
sulfochlorination (where R is C , C , C , and C ) and
18
1
2
14
16
well identified by gas chromatography coupled to mass
spectrometry (GC–MS) in electronic impact (EI) and posi-
tive chemical ionization (PCI) and negative chemical ioni-
zation (NCI) modes. These alkanesulfonyl chlorides, a
mixture of secondary isomers, reacted with glycine in
presence of sodium hydroxide giving anionic surfactants
with general formula R–SO –NH–CH –COONa. Some of
Synthesis of Sodium Salts of Alkane-
1-Sulfonamidoacetic Acid
2
2
surface properties of aqueous solutions of this new type of
sulfonamide surfactants were investigated using surface
tension measurements as critical micelle concentrations
A total of 5.58 mmol of glycine was treated with 15 mL of
10% NaOH. Then, a solution of 1.86 mmol of alkane-1-sul-
fonyl chloride (C –C ) in 10 mL of dichloromethane was
1
2
18
(
CMC), minimum area per molecule (Amin) at the air–water
added drop by drop, under magnetic agitation at 0 °C. At the
end of the addition, the mixture was heated to reflux for 1 h.
The mixture was cooled, and filtered and a white solid was
recovered. Theproductswerethenpurifiedbyrecrystallization
in petroleum ether, to produce the following salt derivatives:
interface and surface excess (C) were investigated for dif-
ferent concentrations at 25 and 50 °C. The foaming power
was also determined by the Bartsch method [9], and the
results obtained were compared to those of a commercial
surfactant, the linear alkylbenzenesulfonate. The stability of
the foam formed was also evaluated. As expected, these
surfactants had good surface-active properties as anionic
surfactants, and showed good foaming power. The effect of
changes in molecular structure (position isomers) and chain
length on their surface properties behaviour was examined,
and compared to that of a commercial anionic surfactant.
Ia1: sodium salt of dodecane-1-sulfonamidoacetic acid;
Ib1: sodium salt of tetradecane-1-sulfonamidoacetic acid;
Ic1: sodium salt of hexadecane-1-sulfonamidoacetic acid,
Id1: sodium salt of octadecane-1-sulfonamidoacetic acid.
Theyieldsobtainedwerequantitativelyhigh(Table 1). The
FTIR spectra (a Perkin Elmer Paragon 500) of these com-
pounds showed definite frequency bands that corresponded to
the presence of various functional groups (Table 1).
Experimental Procedures
Synthesis of Secondary Sodium Salts
of Alkanesulfonamidocetic Acid
Materials
As described elsewhere in more detail [10, 11], n-alka-
nesulfonyl chlorides (RSO Cl) were prepared by photo-
The applied conditions were similar to those used for the
synthesis of the primary sodium salt of dodecanesulfona-
midoacetic acid. Here, the starting materiel is a mixture of
2
sulfochlorination with sulfuryl chloride (Fluka, [97%
pure). n-dodecane, n-tetradecane, n-hexadecane, and
n-octadecane (Fluka, [99% pure) were converted in the
pure phase, respectively, to a mixture of primary and sec-
ondary position isomers of dodecanesulfonyl chlorides,
tetradecanesulfonyl chlorides, hexadecanesulfonyl chlo-
rides, and octadecanesulfonyl chlorides [11, 12]. Alkane-1-
sulfonyl chlorides were prepared by using the Grignard
reagent and chloro-1-dodecane, chloro-1-tetradecane,
chloro-1-hexadecane, and chloro-1-octadecane (Fluka,
Table 1 Yields and I.R. data of sodium salts of primary and sec-
ondary alkanesulfonamidoacetic acid
I.R. band
I
a1
I
b1
I
c1
I
d1
I
a
I
b
I
c
I
d
-1 -1
335 cm , 1175 cm (–SO
-1
335 cm (N–H)
1
3
1
2
–NH) ?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
?
-
1
-1
659.8 cm , 1592 cm (COO)
-
?
Yield (%)
88 79 86 88 85 75 87 89
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J Surfact Deterg (2011) 14:65–72
67
primary and secondary alkanesulfonyl chlorides obtained
foaming power and the stability of the surfactant foam. For
all the products, we determined the foaming power, as the
height of the measured foam immediately after agitation
for every concentration, and the stability of the foam from
the evolution of the foam height versus time [13]. For
estimating foam stability, some workers have measured the
height of foam produced immediately after the mechanical
agitation has stopped and after 1 min [13]. Others have
expressed the foam volume or height to decay to one half
of initial height [9, 14]. To avoid long lasting measure-
from the photosulfochlorination of n-alkanes (C –C ). A
1
2
18
white solid was recovered and the purification of all
compounds was realised by recrystallisation in petroleum
ether, to produce the following salt derivatives:
Ia: secondary sodium salts of dodecanesulfonamidoace-
tic acid;
Ib: secondary sodium salts of tetradecanesulfonamidoa-
cetic acid;
Ic: secondary sodium salts of hexadecanesulfonamidoa-
ments of decay of the foam height, the R parameter was
5
cetic acid;
proposed. It represents the quotient of the foam height after
Id: secondary sodium salts of octadecanesulfonamidoa-
cetic acid.
5
min to the initial foam [9, 15–17]. So the initial foam
height, h , after 5 min were measured for all surfactants.
5
The yields were high (Table 1), and the FTIR spectra of
these compounds showed definite frequency bands that
corresponded to the presence of various functional groups
The residual foam ratio R % was calculated as follows:
5
R5 ¼ ðh5=h0Þ ꢁ 100
(
Table 1).
Results and Discussion
Surface Tension Measurements
The schematic routes of the synthesis of primary and sec-
ondary R–SO –NH–CH –COONa are presented in
Surface tension measurements were performed for freshly
prepared solutions of sulfonamide derivatives in the con-
2
2
Scheme 1.
-
2
-5
centration ranges of 10 –10 mol/L using a tensiometer
Prolabo Tensimat-Densimat TD 2000 No. 56867S)
The starting materials, n-alkanesulfonyl chlorides
(RSO Cl where R = C –C ) were purified on a chro-
(
2
12
18
equipped with a platinum Wilhelmy plate. In most cases,
the accuracy of surface tension measurements was
matography column of silica gel and derivatized into
N,N-diethylsulfonamides for their analysis by GC–MS
using the EI mode, the PCI mode and the NCI mode [18,
19]. The isomeric compositions of each of the alka-
±
0.1 mN/m. Measurements of sodium salts of alkane-1-
sulfonamidoacetic acid were done at 50 °C because of their
low solubility at ambient temperature, and measurements
of secondary sodium salts of alkanesulfonamidoacetic acid
were done at 25 °C. CMC values were determined as the
values at the break point of surface tension versus con-
centration plots (logarithmic scale).
nesulfonyl chlorides (RSO Cl), which are about 20%
2
primary isomer versus 80% secondary isomers, were well
determined by GC analysis, by cross injection of each
primary isomer and GC–MS analysis. As examples, the
most important peaks of mass spectra in EI mode charac-
terizing the presence of N,N-diethylsulfonamide group, and
so the sulfonyl group in the molecules for all isomers of
each alkyl chain length from C to C18 were: m/z = 73 for
Foaming Power and Stability
1
2
?
?
To determine the foaming power and the stability of the
foam, the foam height formed from aqueous solutions of
different sulfonamides was measured according to the
Bartsch method [9] at 25 °C for secondary sodium salts of
alkanesulfonamidoacetic acid and at 50 °C for sodium salts
of alkane-1-sulfonamidoacetic acid. Aqueous solutions of
different concentrations containing the surfactant, varying
[HN(CH CH ) ] , m/z = 58 for [CH CH HN = CH ] ,
2 3 2 3 2 2
?
m/z = 122 for [CH CH N(SO H) = CH ] and m/z =
?
137 for [HSO N(CH CH ) ] , the later was present with
3
2
2
2
2
2
3 2
an intensity of 100% for all isomers of each length chain
except for isomers in position 1 and 2 [19]. The surfactants
I , I , I and Id1 corresponding to primary isomers with
a1 b1 c1
-
general formula CH –(CH ) –CH –SO NHCH COO Na ,
?
3
2 n
2
2
2
-
2
from 10 M until the concentration giving just weak foam
were prepared. For this purpose, a mother solution was
prepared and dilutions were made by the addition of dis-
tilled water. The solution was poured into a 100-mL
graduated cylinder. The cylinder containing the solution
was turned up-side down a total of ten times at a rate of one
turn every 2 s. The foam produced (in mm) was measured
immediately and at intervals until there was a weakening of
the foam volume. These data were used to estimate the
and I , I , I and I with general formula CH –(CH ) –
a b c d 3 2 n
-
CH(SO NHCH COO Na )–(CH ) CH corresponding to
?
2
2
2 m
3
secondary isomers were obtained in a one-step procedure
(Scheme 1). First, the sodium salt of glycine was obtained
from a convenient reaction of sodium hydroxide and glycine
in ca. 90% yield. In the next reaction step, primary and
secondary alkanesulfonyl chlorides were caused to react
with sodium salt of glycine to give a final sodium salt of alka-
nesulfonamidoacetic acid surfactants. All the synthesized
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J Surfact Deterg (2011) 14:65–72
Scheme 1 Preparation of
sodium salts of primary and
secondary
-
+
2
NH CH
2
COOH + NaOH
2 2
NH CH COO Na
-
+
alkanesulfonamidoacetic acid
CH
3
-(CH
2
)
n
-CH
2
-SO
2
Cl
3 2 n 2 2 2
CH -(CH ) -CH -SO NHCH COO Na
Sodium salts of 1-Alkanesulfonamidoacetic acid
n= 10, 12, 14 and 16
-
+
2 2
NH CH COO Na
-
+
CH
3
-(CH
2
)
n
-CH(SO
2
Cl )-(CH
2
)
m
CH
3
3 2 n 2 2 2 m 3
CH -(CH ) -CH(SO NHCH COO Na )-(CH ) CH
Sodium salts of secondary Alkanesulfonamidoacetic acid
n + m = 9, 11, 13 and 15
compounds were purified by crystallisation in petroleum
ether, leadingtoacrystallinesolidformandtheiryieldsandIR
data are listed in Table 1. The results of the given yield values
may indicate that the reaction is not complete. The purity of
the investigated compounds was confirmed by the absence of
minima neartheCMC in the surface tensionplots. Toestimate
the performance of the novel sulfonamide surfactants, alkyl-
benzenesulfonate (LAS) was used as the reference.
7
0
5
0
5
0
5
0
5
0
5
6
6
5
5
4
4
3
3
2
Id
Ic
Ib
Ia
Surface Properties
-5,5
-5,0
-4,5
-4,0
-3,5
-3,0
-2,5
-2,0
-1,5
-1,0
Surface Tension (c) and Critical Micelle Concentration
Log C
(
CMC)
Fig. 1 Variation of surface tension versus the concentration of
sodium salts of secondary alkanesulfonamidoacetic acid at 25 °C
Variations in surface tension values versus log concentra-
tion values for solutions of sodium salts of secondary
alkanesulfonamidoacetic acid (I , I , I and I ) at 25 °C are
70
65
60
55
50
a
b
c
d
Id1
Ic1
Ib1
Ia1
shown in Fig. 1, and for sodium salts of alkane-1-sulfo-
namidoacetic acid (I , I , I and I ) at 50 °C are rep-
a1 b1 c1
d1
resented in Fig. 2. The air–water surface tension c versus
log of the concentration of sodium alkanesulfonamido
acetate surfactants reveals classic behaviour for surfactants,
a steady decrease in c and a clean break with the absence of
a minimum at the CMC. The CMC and surface tension
values obtained for these investigated surfactants compare
well with those of commercial surfactants reported in
Table 2. As listed in Table 2, the lowest surface tension
4
4
3
3
2
5
0
5
0
5
-5,0
-4,5
-4,0
-3,5
-3,0
-2,5
-2,0
-1,5
values were obtained for surfactants Ia1 and I character-
a
Log C
ized by the less important hydrophobic part in their mol-
ecules, e.g., dodecyl chain, if compared to the other
compounds. In addition, for primary surfactants (Ia1 to Id1),
the surface tension values of their solutions decrease from
C14 to C18 length chains and are low in comparison to those
of I to I , while for secondary compounds surface tension
Fig. 2 Variation of surface tension versus the concentration of
sodium salts of primary alkanesulfonamidoacetic acid at 50 °C
non-polar chains so that the molecules tend to aggregate at
lower concentrations [20]. For secondary surfactants, as c
values vary slightly from I to I , but CMC values decrease
a
d
values seem to be equivalent from C14 to C . So, by
18
b
d
increasing methylene units c decreases for Ib1 to I . This
from I to I , it is probably due to the fact that as micel-
a d
d1
behaviour is known as being due to the fact that increasing
hydrophobic chain length of the molecules leads to a
decrease in the aqueous solubility because of the increase
of the repulsion between the polar medium and the
lization occurs at lower concentrations, minimum surface
tension values are quickly reached than for the primary
compounds. A decrease in CMC values is observed, the
lowest one corresponding to the more hydrophobic
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J Surfact Deterg (2011) 14:65–72
69
Table 2 Surface-active
properties of primary and
secondary sodium salts of
alkanesulfonamidoacetic acid,
and for some reference
compounds
10
2
Compounds
T (°C)
CMC
mol/l)
c CMC
(mN/m)
C 9 10
(mol/cm )
A
min
2
(A /molec)
˚
(
-3
I
I
I
I
I
I
I
I
a1
b1
c1
d1
a
50
50
50
50
25
25
25
25
45
45
8.31 9 10
3.98 9 10
1.77 9 10
3.31 9 10
1.08 9 10
27
33
32
30
31
33
34
33
29
–
1.69
1.53
1.49
1.45
2.28
1.87
1.57
1.3
98.25
108.53
111.44
114.52
72.83
-
-
-
-
3
3
4
2
-
-
3
3
b
2.2 9 10
1.2 9 10
3.01 9 10
1.00 9 10
8.20 9 10
88.80
c
105.76
127.73
66.67
-
-
-
4
3
3
d
SAS [24]
SDS [24]
2.49
3.40
49.00
overcome the repulsion resulting from their presence in the
aqueous medium [21].
-
-
-
-
-
-
-
-
-
-
1,8
2,0
2,2
2,4
2,6
2,8
3,0
3,2
3,4
3,6
I , I , I , I
d
a
b
c
Ia1, Ib1, I , I
c1 d1
Surface Excess (C) and Minimum Surface Area per
Molecule (Amin
)
Gibbs equation is used to calculate the mean area demand
per molecule Amin at the interface from surface tension
measurements. Surface excess concentration C and mini-
mum surface area per molecule Amin values are given in
Table 2 along with data for some reference compounds.
Surface excess concentration (C) can be calculated
according to the following equation:
12
13
14
15
16
17
18
Chain length
C ¼ 1=RT ðdc=d ln CÞ
Fig. 3 Critical micelle concentration as a function of the C chain
length of sodium salts of secondary alkanesulfonamidoacetic acid and
sodium salts of primary alkanesulfonamidoacetic acid
where C is called surface excess, dc is the surface pressure,
and C is the surfactant concentrations. A substance that
lowers the surface energy is thus present in excess at or
near the surface, i.e., when the surface tension decreases
with increasing activity of surfactant, C is positive. As
shown in Table 2, increasing hydrophobic chain length
leads to the complete coverage of the surfactant solution by
adsorbed molecules at lower concentrations. Table 2 shows
that the minimum area per molecule at the aqueous solu-
tion/air interface for the prepared surfactants changes with
the hydrocarbon chain length, and it can be seen that the
longer the alkyl chain, the greater the surface area demand.
This result is not expected as it is well known that the
minimum area occupied by classical ionic surfactants at the
surface of water is determined, in part, by a competition
between Van der Waals forces among hydrocarbon chains
and repulsive interactions (e.g., electrostatic or hydratation)
between polar head groups. Therefore, an increase in
hydrocarbon chain length results in a decrease in the
minimum area per molecule at the surface of aqueous
solution [22]. In Table 2, as Amin increases with hydro-
carbon chain length for the two series of surfactants, this
would be due to the fact that the balance of forces leading
surfactant, e.g., Id1 and I in Fig. 3, which exhibits a linear
d
relationship as shown in Eqs. 1 and 2:
2
I , I , I and I : log CMC = -0.247N–1.9 R = 0.987
a
b
c
d
I , I , I
a1
and I : log CMC = -0.227N–1.87
d1
b1
c1
2
R = 0.977
It is not obvious to draw conclusions here on the iso-
meric effect on CMC values, because of the difference in
temperature measurements. But, if the CMC is considered
to vary slightly by increasing the temperature within a
narrow range of temperature, Table 2 shows that the CMC
values of the secondary isomers are lower than those of the
primary ones, except for Ia1 and I . This could be due to the
a
presence of two tails in secondary isomers because of
the shift of the hydrophilic group to a more central position
in the molecule, as in the case of branched surfactants.
Then, the water/surfactant molecule interactions increased,
which forced them to the air–water interface at extremely
low concentrations, and micellization of molecules to
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J Surfact Deterg (2011) 14:65–72
to the organization of the sulfonamide surfactants at the
surface of aqueous solutions is, therefore, different from
the balance of forces governing the assembly of classical
surfactants at the surfaces of aqueous solutions [23]. It also
can be seen that Amin values of secondary surfactants are
lower than those of primary surfactants having the same
length chain, even if the measurements are not realised at
the same temperature, which indicates that the molecules
of secondary surfactants are more tightly packed at the air–
water interface than primary ones, which could be due to
the branching character of the secondary isomers of sur-
factants. Thus, size of surfactant segment is shown to be
important in determining the surface area occupied by
surfactant at the interface, both for primary or secondary
isomers.
130
120
1
1
10
00
9
8
7
6
0
0
0
0
50
12
13
14
15
16
17
18
chain length
Fig. 5 Height of the foam formed versus the C chain length of
secondary sodium salts of alkanesulfonamidoacetic acid
Foaming Properties
with the Bartsch methods [13] at certain concentrations, in
-
3
our case at 6 9 10 mol/L. As observed from Fig. 5, the
chain length in the hydrophobic tail has an effect on
foaming power by comparing the isomers (I to I ). I
d
The Bartsch method [25] was used to evaluate the foaming
properties of alkanesulfonamide surfactants, and the foam
evolution and foam stability were determined as a function
of concentration.
a
d
possesses the best micelle-forming ability among the four
surfactants, but a weak foaming power when compared to
the other sulfonamides (Fig. 4), which is probably due to
its weak solubility [26]. It can be emphasized that there is a
maximum amount of foam for the sulfonamide with a chain
Foaming Power
The relationships between the foam height versus the
concentration of secondary sulfonamide surfactants: I , I ,
length of C16 corresponding to the I surfactant, showing a
c
better foaming ability and foam stability than the other
sulfonamide surfactants (Fig. 5). The same behaviour has
been reported by Quack and Trautmann for sodium al-
kanesulfonates (SAS), where the better foam power was
observed for C –C [27].
a
b
I and I , and linear alkylbenzenesulfonate are illustrated in
c
d
Fig. 4. It appears that the secondary sodium salts of alka-
nesulfonamidoacetic acid have good foaming power. The
foam formed by these surfactants can be considered as
steady or metastable or dry [15]. It can also be concluded
that all the surfactants tested here, possess good foaming
power. Figure 5 illustrates the relationships of the foam
height versus the carbon chain length of secondary sodium
salts of alkanesulfonamidoacetic acid, foam build-up by
mechanical action. The height of the foam is measured
1
5
16
Stability of the Foam
The changes in foam height (h) as a function of time (t) are
shown in Figs. 6, 7, 8, 9, 10 for aqueous solutions of I , I ,
a
b
I and I , and of linear alkylbenzenesulfonate. As shown on
c
d
these figures, the general aspect was similar to that
obtained for SDS surfactant with other methods [9], indi-
cating a good foam stability versus time for every con-
centration of the surfactants. It is interesting to note that the
results obtained for all surfactants synthesised show good
surface properties, and good foaming power characterized
by a metastable or dry foam. The foam stability of the
solutions can be more reflected by the residual foam height
ratio R where foams with R = 50% can be considered as
I c
1
1
1
40
20
00
I d
I b
I a
L A S
8
6
4
2
0
0
0
0
0
5
5
metastable, whereas lower values of R indicate foams of
5
low stability [9, 15]. R values of aqueous solutions of I ,
5
a
I , I and I , and LAS were plotted as a function of their
b
c
d
0
,000 0,001 0,002 0,003 0,004 0,005 0,006 0,007 0,008 0,009 0,010 0,011
concentrations. High foam stability was obtained for all
Time (min)
surfactants synthesized (R [ 60%). Secondary sodium
5
salts of dodecanesulfonamidoacetic acid had not only a
Fig. 4 Height of the foam formed versus the concentration of I
, I , and LAS
a b
, I ,
I
d
c
good foam height, but it also exhibited good foam stability.
1
23

J Surfact Deterg (2011) 14:65–72
71
100
70
9
8
7
6
5
4
3
2
0
0
0
0
0
0
0
0
6
5
4
0
0
0
0,006 M
0
0
,002 M
,0006 M
0,0003 M
,0002 M
0
30
0
0
0
0
0
,01 M
,008 M
,006 M
,004 M
,002 M
2
0
10
0
0
50
100
150
200
250
0
50
100
150
200
250
Time (min)
Time (min)
Fig. 6 Variation of the height of the foam versus the time for the
secondary sodium salts of dodecanesulfonamidoacetic acid
Fig. 9 Variation of the height of the foam versus the time for the
secondary sodium salts of octadecanesulfonamidoacetic acid
1
1
1
40
20
00
0.01 M
0
0
,01 M
,009 M
0
0
0
0
.009 M
.008 M
.007 M
.006 M
0,008 M
0
0
0
,007 M
,006 M
,005 M
70
80
60
40
20
0
6
0
50
4
0
50
100
150
200
250
0
50
100
150
200
250
Time (min)
Time (min)
Fig. 10 Variation of the height of the foam versus the time for the
linear alkylbenzenesulfonate
Fig. 7 Variation of the height of the foam versus the time for the
secondary sodium salts of tetradecanesulfonamidoacetic acid
1
1
1
40
20
00
respectively. Consequently, the foams formed were stable
(metastable or dry).
c = 0,006
c = 0,003
c = 0,0012
c = 0,0008
c = 0,0006
Thus, the application of these molecules in commercial
processes could allow us to dramatically reduce the con-
centration of surface active materials used for the same level
of performance. These surfactants have a greater capacity to
associate themselves, forming aggregates, compared to
those of ordinary surfactants. This suggests that the intro-
duction of a sulfonamidoacetate group as a hydrophilic part
of the amphiphile (position isomers) promises environ-
mentally acceptable anionic surfactants in view of their high
performance, especially their foaming power.
8
6
4
2
0
0
0
0
0
0
50
100
150
200
250
Time (min)
Fig. 8 Variation of the height of the foam versus the time for the
secondary sodium salts of hexadecanesulfonamidoacetic acid
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Author Biographies
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2. Fekarcha L, Tazerouti A, Results not yet published
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properties of surfactants derived from natural products. Part 2:
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Radia Mousli earned her Organic Chemistry M.Sc. from the
University of Sciences and Technology Houari Boum e´ di e` ne, Algiers,
Algeria (2006). She is now a Ph.D. student at the same University.
Her research interests are anionic surfactants, sulfonamide deriva-
tives, their synthesis, properties and applications.
1
1
1
4. Schick MJ, Beyer EA (1963) Foaming properties of non-ionic
detergents. J Am Oil Chem Soc 4:66–68
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tative characterization of foam behaviour. Polym Int 52:536–541
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surfactants. 7. Synergism in foaming and its relation to other
types of synergism. J Am Oil Chem Soc 65:663–668
7. Tamura T, Kaneko Y, Ohyama M (1995) Dynamic surface
tension and foaming properties of aqueous polyoxyethylene
n-dodecyl ether solutions. J Colloid Interf Sci 173:493–499
8. Assassi N, Tazerouti A, Canselier JP (2005) Analysis of chlori-
nated, sulfochlorinated and sulphonamide derivatives of
Amel Tazerouti received her Organic Chemistry M.Sc. (1988) and
Ph.D. (1994) from the University of Sciences and Technology Houari
Boumediene, Algiers, Algeria. During her doctorate, she joined the
Department of Chemistry, Catholic University of Louvain, Louvain-
La-Neuve, Belgium, in 1991 on a Belgium fellowship for 1 year. She
is currently Professor and Director of the Laboratory of Applied
Organic Chemistry, Faculty of Chemistry, University of Sciences and
´ `
1
1
Technology Houari Boumediene, Algiers, Algeria. Her main research
´ `
fields are synthesis and properties of surfactants and their mixtures.
n-tetradecane by gas chromatography/mass spectrometry.
Chromatogr A 1071:71–75
J
1
23