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POLYMERS FOR ADVANCED TECHNOLOGIES

Polym. Adv. Technol. 11, 4856 (2000)

Surface Activity and Thermodynamic


Properties of Water-soluble Polyester
Surfactants Based on 1,3Dicarboxymethoxybenzene Used for
Enhanced Oil Recovery
A. M. Al-Sabagh*

Egyptian Petroleum Research Institute (EPRI), Nasr City 11727, Cairo, Egypt

ABSTRACT W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W
The surface activity and thermodynamic properties for
eight low molecular weight nonionic co-polyester (PE)
surfactants have been investigated. Surface and interfacial tensions (IFT) of surfactants in aqueous solutions
were measured using the spinning drop technique. From
these measurements, the critical micelle concentration
(CMC), the surface pressure at CMC (YCMC), the
maximum surface concentration (max), the minimum
area/molecule at the aqueous solution/air interface
(Amin), the effectiveness of surface tension reduction
(PCMC), the alkane carbon number (nmin) and the IFT at
nmin (Ymin) were determined. The thermodynamic
parameters of micellization (DGmic, DHmic and DSmic)
and of adsorption (DGad, DHad and DSad) for these
polymeric surfactants were also calculated. Structural
effects on micellization and adsorption are discussed in
terms of these parameters. The results show that the DGad
values were more negative than DGmic values for these
compounds, so that they favored adsorption before the
micellization process. They exhibited IFT in the order of
103 to 104 mN/m against the thin alkane carbon
number range 69. This range seemed to be prefered for
* Correspondence to: A. M. Al-Sabagh, Egyptian Petroleum
Research Institute (EPRI), Nasr City 11727, Cairo, Egypt.

CCC 10427147/2000/01004809 $17.50


Copyright 2000 John Wiley & Sons, Ltd.

enhanced oil recovery. Copyright 2000 John Wiley &


Sons, Ltd.
KEYWORDS: polymeric surfactants; thermodynamic;
micellization; adsorption; enhanced oil recovery; polyester surfactants

INTRODUCTION W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W
For economic considerations and other factors,
laboratory evaluation studies should precede field
applications of any effective formulation of surfactant systems to be used for enhanced oil recovery
(EOR). Extensive work has been done to evaluate
most of the commercially available monomeric
surfactants for EOR applications. Polymeric surfactants as EOR agents have appeared in the technical
and patent literature [15]. Only a few of these
polymeric surfactants have been extensively studied. However, little reliable information on the
surface and thermodynamic properties of wellcharacterized, highly purified compounds of this
type is available [69]. In polymeric ethoxylated
compounds a generalized formula is often used
since a well-characterized structure is not possible.
The data on ethoxylated surfactants are even more
Received 28 June 1999
Revised 15 September 1999
Accepted 26 September 1999

Water-soluble Polyester Surfactants / 49

FIGURE 1. Generalizing formula for the investigated polyesters.

sparse than for conventional ethoxylated ones.


Moreover, considerable confusion concerning the
surface, chemical and colloidal properties of polymeric surfactants is reported in the literature [10
13]. In the micelle polymer flooding process, the
injected water contains such an amount of an
appropriate polymeric surfactants to (IFT) substantially reduce the oilwater interfacial tensior [14].
The polymeric surfactants have been described in
application EOR by some investigators [15, 16].
The role of low IFT in EOR has been recognized
in numerous investigations of both experimental
and theoretical character [17, 18]. The equivalent
alkane carbon number related to IFT for polymeric
surfactants in EOR has been studied [19]. In this
study, a laboratory evaluation of thermodynamic
parameters of micellization and adsorption for
some water-soluble polyester surfactants, based
on phthalic or maleic anhydride, has been carried
out. The study was extended to evaluate them via
interfacial tension behavior. This study necessitates
thermodynamic and IFT data for these compounds
to predict their general trend in a micellar flooding
process.

EXPERIMENTAL W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W
Eight low molecular weight water-soluble polyester surfactants were prepared by reacting resercinol
with
chloroacetic
acid;
the
1,3dicarboxymethoxybenzene was precipitated with
dilute HCl. The polyesters were prepared by the
Copyright 2000 John Wiley & Sons, Ltd.

reaction of 1,3-dicarboxymethoxybenzene with


phthalic or maleic anhydryde respectively in the
presence of tetraethylene glycol. The obtained
polyesters were condensed with polyethylene
glycol of molecular weight 400, 600, 1000 and
2000. The preparation and characterization of these
compounds have been described previously [19].
Generalized formula of these surfactant groups is
shown in Fig. 1, and some characterization is given
in Table 1.
The surface tension for these surfactants was
measured at 20, 30, 40 and 50 C, and the interfacial
tension was measured at 50 C using spinning drop
tensiometer (SDT Kruss model SITE 04).

RESULTS AND DISCUSSION W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W


The critical micelle concentrations (CMCs) of the
polyester surfactants at 20, 30, 40 and 50 C were
determined by plotting the surface tension (Y)
versus ln C (soluble concentration). The CMC
values were determined from the abrupt change
in the slope of Y versus ln C plot. These values are
listed in Table 1.
Generally, an increasing number of ethylene
oxide (EO) units increases the CMC [2023].
Increasing EO increases hydrophilicity, which
increases solubility of the surfactant in water. Such
improved solubility lowers the tendency for surfactants to form micelles in water and increases the
CMC. In the present work the data in Table 1 are
consistent with this behavior for the polyester
Polym. Adv. Technol., 11, 4856 (2000)

50 / Al-Sabagh
TABLE 1. Some Characterizations of the Investigated Polyester Surfactants

CMC  104 (mol/dm3)


Molecular
weight

No. of
HLB
ethylene
oxide (n)

nn Ymin
(mN/
m)  103

20 C 30 C 40 C 50 C

Resorcinol phthalic PE(P)13


anhydride-diol(PEG-400)

1920

13

6.3

4.0

230 225 220 210

Resorcinol phthalic PE(P)17.6


anhydride-diol(PEG-600)

2320

17.6

6.8

1.0

235 230 226 219

Resorcinol phthalic PE(P)26.7


anhydride-diol(PEG-1000)

3120

26.7

7.7

0.4

224 236 230 225

Resorcinol phthalic PE(P)49.6


anhydride-diol(PEG-2000)

5120

49.6

8.6

0.9

250 240 235 230

Resorcinol maleic
anhydride-diol(PEG-400)

PE(M)13

1824

13

6.6

8.0

290 281 273 264

Resorcinol maleic
anhydride-diol(PEG-600)

PE(M)17.6

2224

17.6

7.2

1.0

314 290 280 272

Resorcinol maleic
anhydride-diol(PEG-1000)

PE(M)26.7

3024

26.7

7.9

0.6

332 305 294 286

Resorcinol maleic
anhydride-diol(PEG-2000)

PE(M)49.6

5024

49.6

8.8

0.8

339 324 302 290

Polymeric
polyester
surfactant

Designation

PE = polyester; (P) = polyester based on phthalic anhydride; (M) = polyester based on maleic anhydride;
diol = tetraethylene glycol; PEG = polyethylene glycol.

surfactant PE(P)n or PE(M)n (n = 13, 17.6, 26.7 and


49.6, respectively). From the data in Table 1, it can
be seen that the general trend is a continuous
increase in CMC with an increase of the number of

EO units and hydrophiliclipophilic balance (HLB)


as shown in Figs 2 and 3. This behavior is consistent
with previous data [24, 25]. From Table 1 it is noted
also that increasing the temperature from 20 to

TABLE 2. Surface Excess, Area/Molecule and Effectiveness for the Polyester Surfactants
max (mol/cm2  1010)

Amin (nm2  100)

PCMC (m N/m)

Surfactant

20 C

30 C

40 C

50 C

20 C

30 C

40 C

50 C

20 C

30 C

40 C

50 C

PE(P)13
PE(P)17.6
PE(P)26.7
PE(P)49.6
PE(M)13
PE(M)17.6
PE(M)26.7
PE(M)49.6

0.83
0.81
0.79
0.77
1.14
1.04
1.03
1.00

0.75
0.77
0.76
0.74
1.09
0.99
0.97
0.97

0.76
0.74
0.73
0.71
1.03
0.96
0.94
0.92

0.72
0.70
0.68
0.68
0.95
0.91
0.89
0.88

0.200
0.205
0.210
0.216
0.146
0.159
0.161
0.166

0.210
0.216
0.218
0.224
0.152
0.167
0.171
0.174

0.218
0.224
0.227
0.234
0.161
0.173
0.177
0.180

0.230
0.237
0.244
0.264
0.175
0.182
0.187
0.189

38.5
37.5
35.0
33.5
37.0
35.5
33.0
31.5

38.0
37.0
34.5
32.0
35.0
34.0
32.0
30.0

37.0
36.0
34.0
31.5
34.0
33.0
31.5
29.0

36.0
35.0
33.5
30.0
33.0
32.0
30.0
28.0

Copyright 2000 John Wiley & Sons, Ltd.

Polym. Adv. Technol., 11, 4856 (2000)

Water-soluble Polyester Surfactants / 51

FIGURE 3. (B) CMC versus n; (C) DGmic versus n, and (D)


DGad versus n for PE(M)n.

50 C leads to a decrease in CMC for both polyester


based on phthalic or maleic anhydride (PE(P)n or
PE(M)n).
The maximum surface excess concentration
(max) in mol/dm2 was calculated from the
relationship:


1
Y
1
max
RT d ln C T

FIGURE 2. 2 (A) and 3(A): HLB versus n; (B) CMC versus


n; (C) DGmic versus n, and (D) DGad versus n for PE(P)n.

Copyright 2000 John Wiley & Sons, Ltd.

(where R = Gas Constant (8.314) and T = T+273(K)).


The max values in Table 2 were used to
calculate the minimum area/molecule (Amin in
nm2/molecule) at the aqueousair interface using
the relationship:
Polym. Adv. Technol., 11, 4856 (2000)

52 / Al-Sabagh
TABLE 3. Thermodynamic Parameters of Micellization and Adsorption for the Polyester Surfactants Based on Phthalic (P)
and Maleic (M) Anhydrid

Surfactant
PE(P)13

PE(P)17.6

PE(P)26.7

PE(P)49.6

PE(M)13

PE(M)17.6

PE(M)26.7

PE(M)49.6

Temp.
( C)

DGmic
(kJ/mol)

DHmic
(kJ/mol)

20
30
40
50

9.19
9.24
9.30
9.41

1.65
1.97
2.28
2.54

20
30
40
50
20
30
40
50

9.14
9.19
9.23
9.31
9.05
9.13
9.19
9.24

2.58
2.93
3.29
3.61
5.89
6.32
6.77
7.23

20
30
40
50

9.05
9.10
9.15
9.20

8.59
8.84
9.05
9.28

20
30
40
50

8.62
8.70
8.77
8.85

3.10
3.42
3.75
4.07

20
30
40
50

8.43
8.58
8.71
8.78

5.34
5.66
6.00
6.40

20
30
40
50

8.30
8.42
8.59
8.66

6.94
7.34
7.69
8.14

20
30
40
50

8.24
8.34
8.53
8.63

9.63
10.14
10.56
11.07

DSmic
(kJ/mol K)
0.037

0.040

0.051

0.060

0.040

0.047

0.052

0.061

DGad
(kJ/mol)

DHad
(kJ/mol)

14.20
14.50
14.85
15.00

18.41
19.27
20.27
21.14

14.00
14.25
14.45
14.65
13.68
14.07
14.12
14.35

21.30
22.36
23.47
24.45
24.61
25.73
26.85
27.83

13.35
13.66
14.17
15.00

27.67
28.76
29.65
30.34

11.87
11.90
12.07
12.33

32.08
33.55
34.80
36.12

11.83
11.99
12.15
12.29

37.98
39.52
39.36
40.92

11.50
11.72
11.95
12.04

38.31
39.79
41.26
42.87

12.00
12.35
12.51
12.90

44.39
45.79
47.29
48.97

DSad
(kJ/mol K)
0.11

0.12

0.13

0.14

0.15

0.17

0.18

0.18

Thermodynamic Parameters of Micellization


Amin

1016
N

where N is Avogadro's number.


Values of Amin are listed in Table 2. It is evident
that Amin decreases with increase in the number of
EO in the molecule in agreement with the relationship observed for other polyoxyethylenated nonionics [26]. The Amin also increase with increase in
temperature, as would be expected from the
increased thermal agitation of the molecules in
the surface film [27].
The effectiveness (PCMC) of surface tension
reduction was measured by the surface pressure
at the CMC [28]. PCMC in these compounds showed
a steady decrease with increase in the number of
EO, as given in Table 2.
Copyright 2000 John Wiley & Sons, Ltd.

Table 3 lists standard free energies, DG0mic enthalpies, DH0mic, and entropies, DS0mic, of micellization for the four nonionic polyester surfactants
investigated based on phthalic or maleic anhydride
respectively (PE(P)n and PE(M)n). DG0mic values
were calculated by use of the relationship:
Gmic RT ln CMC

The DGmic values calculated in this manner at


each of the four temperatures used (20, 30, 40 and
50 C) were plotted against the number of EO in the
molecule and smooth curves were drawn through
data points in Figs 2 and 3. From these four curves,
DHmic and DSmic values were calculated from the
relationship:
Polym. Adv. Technol., 11, 4856 (2000)

Water-soluble Polyester Surfactants / 53

was calculated from the relationship:


Hmic Gmic TSmic

FIGURE 4. Typical surfactant, IFT behaviour of (A): normal


alcohol; (B): branched alcohol (C): NaCl, on nmin for
PE(P)26.7.

Gmic
Smic
T

By using the values for DGmic and DSmic, the DHmic


Copyright 2000 John Wiley & Sons, Ltd.

From the thermodynamic data of micellization


listed in Table 3, one may conclude that micellization process is spontaneous (DGmic < 0). DGmic was
found to become less negative with increasing EO
content in the molecule, which leads to steric
inhibition of micellization [29].
The DSmic values in Table 3 are all positive,
indicating increased randomness in the system
upon transformation of the surfactant molecules
into micelles. The slight increase in the positive
DSmic value with increase in EO in the surfactant
molecule has been observed by other investigations
[30].
The desolvation of the oxyethylene units has
been stated [20, 30, 31] to be the major contributing
factor to the positive entropy of micellization in
polyoxyethylenated nonionics. An alternative explanation is that there is less restriction on the
motion of the surfactant molecule when it is in the
essentially water-free environment of the micelle
than in the aqueous phase. This extends to both the
hydrophobic alkyl chain, which is in a hydrocarbon-like environment in the interior of the
micelle, and the adjacent part of the hydrophilic
polyoxyethylene chain, which is freed (on the only
partially solvated micellar surface) from some of
the restrictions placed upon it by hydrogen bonding to water molecules.
The DHmic values are listed in Table 3 for the
eight investigated polyester surfactants, and are all
positive, in contrast to those of Crook et al. [20], who
report negative DHmic values at 25 C for p-tertPolym. Adv. Technol., 11, 4856 (2000)

54 / Al-Sabagh

[20, 30], indicating that a greater number of hydrogen bonds between polyoxyethylene chain oxygen
and water molecules are broken in the micellization
process as the number of oxyethylene units in the
molecule increases.
Thermodynamic Parameters of Adsorption
Table 3 lists free energies, DGad, enthalpies, DHad
and entropies, DSad, of adsorption DGad values
which were calculated by use of the relationship
Gad RT ln CMC 6:023  101 CMC ACMC 6

FIGURE 5. Typical surfactant, IFT behaviour of (A): normal


alcohol, (B): branched alcohol and (C): NcCl, on nmin for
PE(M)26.7.

octylphenoxypoly (ethenoxyethanols) containing


less than four EO units. The values increase with
increase in the number of EO units in the molecule,
in accordance with the observations of others
Copyright 2000 John Wiley & Sons, Ltd.

DHad and DSad values listed in Table 3 are obtained


as before from relationships corresponding to eqs
(4) and (5).
The DSad values are all positive and slightly
greater than the DSmic values for the same
compounds. This may reflect the greater freedom
of motion of the hydrophobic section at the planar
air/aqueous solution interface compared with that
in the relatively cramped interior beneath the
convex surface of the micelle. The change in DSad
with increase in the number of EO in the molecule,
on the other hand, approximates to that observed in
DSmic.
This is reasonable, since groups at the micellar
surface would not experience the space restriction
imposed upon groups extending into the interior.
The DHad values are all more positive than DHmic,
indicating that the hydrogen bonds between the
water and the oxygen of EO chain in the surfactant
molecule are broken in the process of adsorption at
airaqueous solution interface more than in the
micellization process.
Polym. Adv. Technol., 11, 4856 (2000)

Water-soluble Polyester Surfactants / 55

The relation between DGad and EO units is


shown in Figs 2 and 3 for PE(P)27.7 and PE(M)27.7
respectively. The values of DGad are all negative
and greater than the negative values of DGmic.
These observations are consistent with data
reported [32], indicating that steric factors inhibit
micellization more than they do adsorption at the
airaqueous solution interface. This behavior of the
investigated polyester surfactants helps to form
stable emulsions as favored for enhanced oil
recovery.
Interfacial Tension Behavior for the Investigated
Polyester Surfactants
From the two groups of polyester surfactants based
on phthalic and maleic anhydride, the PE(P)26.7
and PE(M)26.7 are selected to confirm the general
IFT behavior. The study of IFT in an oil/surface/
water system is greatly facilitated by use of the
alkane model. In this investigation, the crude oil is
replaced by a member of the homologous n-alkane
series which shows IFT behavior identical to that of
crude oil [33], to facilitate evaluation of surfactant
for enhanced oil recovery.
If a surfactant system gives a low IFT against a
crude oil, it also behaves similarly against a
particular alkane equivalent to the crude oil in
terms of its interfacial tension behavior. The data
presented in Table 1 show the values of nmin
(alkane carbon number at which the maximum
reduction of IFT obtained) and Ymin (IFT) at nmin.
The IFT data as shown in Table 1 are situated
between 103 and 104 mN/m and the nmin
between 6 and 9. These results are considered
suitable for enhanced oil recovery in polymeric
flooding [34]. Figures 4 and 5 reveal the effect of the
typical surfactant IFT behavior of normal or
branched alcohol and NaCl on the nmin for
PE(P)26.7 and PE(M)26.7 respectively. When normal alcohols (propanol, butanol and pentanol)
were added to the surfactant solution, a downward
nmin shift was obtained with propanol, accompanied by a decrease in the IFT as shown in segment
A of Figs 4 and 5. This may be because the propanol
is considered a co-surfactant and increases surfactant stability at the interface. Butanol and pentanol
always give nmin upward shifts such as the data
plot for butanol and pentanol in the same segment
A in Figs 4 and 5. These nmin upward shifts with
alcohol may due to increasing hydrophobicity of
alcohol, leading to an increase of solubility of the oil
phase, so that the addition of higher alcohol is
accompanied by an increase in obtained IFT. This
may be indirect evidence that the adsorption of
surfactant at the interface and its nmin are linked in
some way. Segment B in Fig. 3 clears the effect of
branched alcohol (iso-propanol, iso-butanol and
iso-pentanol) on the nmin of PE(P)26.7 and
PE(M)26.7 respectively. The plots show that nmin
are shifted upward, which may be due to miscibility, since the alcohol molecule becomes more
and more oil-like in character as the hydrocarbon
segment becomes larger and more hydrophobic.
Copyright 2000 John Wiley & Sons, Ltd.

Also, the effect of electrolyte (NaCl) concentration


on nmin is shown in Figs 4 and 5, segment C, with no
alcohol addition. The plots show that the electrolyte
concentration causes an upward shift in the
surfactant nmin accompanied with an increase of
IFT [35].

CONCLUSIONS W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W W
The following conclusions are drawn:
(1) The PE(P)n (n = 13, 17.6, 26.7 and 49.6) reduce
the surface and IFT greater than PE(M)n
(n = the same number of ethylene oxide).
(2) The CMC for PE(P)n are smaller than the CMC
for PE(M)n.
(3) All investigated polyester surfactants favor the
adsorption process before the micellization
process.
(4) Both PE(P)n and PE(M)n give minimization of
IFT in range of 103 to 104 mN/m, and nmin
lies between 6 and 9 which favors polymeric
flooding in the area of enhanced oil recovery.

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