Characterization of Acrylamide Polymers for Enhanced

Oil Recovery

Anupom Sabhapondit,1 Arun Borthakur,1 Inamul Haque2

1
Regional Research Laboratory, Jorhat, 785006, Assam, India
2
Dibrugarh University, Dibrugarh, 786004, Assam, India

Received 16 July 2001; accepted 22 April 2002

ABSTRACT: Four different copolymers, of acrylamide and thermogravimetry thermograms because of the elimination of
acrylic acid, acrylamide and 2-acrylamido-2-methyl propane gases such as CO2, SO2, CO, and NH3. The replacement of the
sulfonic acid, N,N-dimethylacrylamide and acrylic acid, and acrylate group with a sulfonate group produced polymers that
N,N-dimethylacrylamide and 2-acrylamido-2-methyl propane were more compatible with brine, whereas the replacement of
sulfonic acid (sodium salts), were prepared. The copolymers acrylamide with a more hydrophobic group such as N,N-
were characterized by their intrinsic viscosities and monomer dimethylacrylamide produced a more shear-resistant polymer.
ratios and with IR, 1H-NMR, and X-ray diffraction (XRD) spec- A N,N-dimethylacrylamide-co-sodium-2-acrylamido-2-methyl
troscopy. No crystallinity was observed by differential thermal propane sulfonate copolymer was better with respect to ther-
analysis, and this was well supported by XRD. All the poly- mal stability when the polymer solution was aged at 120°C for
mers showed low decomposition temperatures. A number of a period of 1 month. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci
decomposition temperatures were observed in differential 87: 1869 –1878, 2003

INTRODUCTION cause the ONH2 group is hydrolyzed at 80 –90°C: this

leads to the formation of a solution of very low vis-
With increasing worldwide demands on the energy
cosity under reservoir conditions.8 If the hydrogens of
sector, polymers have gained immense importance as
the amide group are replaced by methyl groups, this
enhanced oil recovery agents among oilfield chem-
ists.1–3 Enhanced oil recovery is going to play a crucial effect should practically be eliminated. Moreover,
role in the production of petroleum, which is so vital polymers containing OSO⫺ 3 groups are expected to

for the development of any country. Although the offer higher stability in solution, on account of their
consumption of crude oil has increased sharply in stronger hydrogen bonding, than polymers containing
recent years, there is a decline in oil reservoirs. In this OCO⫺ 2 groups. Therefore, sodium-2-acrylamido-2-
context, designing a suitable agent for the tertiary methyl propane sulfonate (AMPS) should be more
recovery of oil from high-temperature reservoirs with suitable than sodium acrylate (AA) as a comonomer
high-density brine fluid is considered a challenging with substituted acrylamide (AM). Also, OSO⫺ 3
job for chemists. Although polyacrylamide, especially should help with the water solubility of the polymer
partially hydrolyzed polyacrylamide, is considered more than OCO⫺ 2 because of the former’s stronger
the best mobility control agent in surfactant–polymer hydrophilicity.
and polymer-augmented water flooding processes, it From a rheological point of view, the presence of
is not suitable for high-temperature reservoirs some hydrophobic groups such as OCH3, along with
(⬎90°C) with high-density brine fluids.4 – 6 The ideal hydrophilic groups, may help with shear resistance.9
candidate for the enhanced recovery of oil from such Again, the presence of bulky side chains should assist
reservoirs should have long-term thermal stability un- in the retention of a comparatively higher solution
der the reservoir conditions of temperature and salin- viscosity after the reduction of the solution viscosity
ity.7 Moreover, it should be cost-effective. by salt than that obtained with smaller side chains.
Substituted polyacrylamides, or polyacrylamides Keeping in mind all these points, we selected and
copolymerized with a suitable monomer, can yield a prepared in our laboratory four different copolymers of
better product that may be thermally stable at least for AM or substituted AM. The copolymers were character-
a period. Polyacrylamide is not thermally stable be- ized by potentiometry, IR, 1H-NMR, X-ray diffraction
(XRD), thermogravimetry, and intrinsic viscosities. The
copolymers were poly(acrylamide-co-sodium acrylate)
Correspondence to: A. Borthakur.
(AM–AA), poly(acrylamide-co-sodium-2-acrylamido-2-
Journal of Applied Polymer Science, Vol. 87, 1869 –1878 (2003) methyl propane sulfonate) (AM–AMPS), poly(N,N-di-
© 2003 Wiley Periodicals, Inc. methylacrylamide-co-sodium acrylate) (NNDAM–AA),
1870 SABHAPONDIT, BORTHAKUR, AND HAQUE

TABLE I
Synthesis, Composition, and Intrinsic Viscosities of Copolymers

Comonomer Intrinsic
Comonomer in copolymer (wt %)
in reaction viscosity
mixture From From in 0.1M
Comonomer used (wt %) 1
H-NMR potentiometry NaCl at
27°C
Sample A B A B A B A B (dL/g)

1 AM AA 70 30 60.2a 39.8a 64.4 35.6 14.4

2 AM AMPS 70 30 60.3 39.7 66.6 33.4 5.51
3 NNDAM AA 70 30 62.0 38.0 67.8 32.2 5.44
4 NNDAM AMPS 70 30 57.9 42.1 62.8 37.2 4.75
a
Value obtained by correction of the potentiometric data for the gravimetric error (due to the presence of moisture),
determined from TGA.

and poly(N,N-dimethylacrylamide-co-sodium-2-acryl- ized with NaOH (2% solution). The final copolymer
amido-2-methyl propane sulfonate) (NNDAM–AMPS). was isolated by precipitation with acetone and dried
in a vacuum oven for 10 –15 h.
EXPERIMENTAL
Materials Instrumentation
Copolymers of AM and N,N-dimethylacrylamide Kinematic viscosity is measured with an Ubbelohde
(NNDAM) and of acrylic acid (sodium salt) and viscometer (fit with an automatic Schott Gerate AVS
AMPS were prepared in the laboratory. AM, obtained 400 instrument, Germany). Solution viscosity is mea-
from Merck–Schuchardt (Germany), was recrystal- sured with the help of a Brookfield LVTDV II viscom-
lized from a water– ethanol mixture. NNDAM, ob- eter equipped with an Ultra Low (UL) adapter
tained from Aldrich Chemical Co., was exposed over (Stoughton, MA). A rotoviscometer having a maxi-
calcium hydride for about 24 h for the removal of mum shear rate of 1312 s⫺1 is also used in some cases.
stabilizers and was then purified by distillation in Thermogravimetric experiments are performed in a
vacuo. Purified acrylic acid purchased from G. S. Universal V2.5H TA instrument (New Castle, DE) in a
Chemicals (New Delhi, India) was used as received. nitrogen atmosphere at a heating rate of 8°C/min. IR
AMPS, obtained from Merck–Schuchardt, was puri- spectra are taken with a PerkinElmer IR 883 instru-
fied by recrystallization. Ammonium persulfate and ment (Beaconsfield, UK), taking samples in KBr pel-
sodium metabisulfite were obtained from CDH (New lets. 1H-NMR spectra are taken with a Bruker 300-
Delhi, India) and purified by recrystallization. MHz instrument (Fallanden, Switzerland) using TMS
as the reference and D2O as the reference and D2O as
Preparation of the polymers the solvent. Wide-angle XRD are taken in an X-ray
diffractometer, Type JDX-11P3A (JEOL, Tokyo, Japan).
The synthesis of AM copolymers is a well-established
phenomenon.10 Distilled or purified monomers were
dissolved in degassed and distilled water in the ratio
RESULTS AND DISCUSSION
given in Table I to obtain a 12 wt % aqueous solution.
Residual oxygen was removed by nitrogen being bub- The intrinsic viscosities of the copolymers and the
bled through the solution for an hour under constant ratios of the monomers in the copolymers are pre-
stirring at 25°C. To this solution, recrystallized ammo- sented in Table I. 1H-NMR and potentiometric titra-
nium persulfate (0.15 wt % monomer) and sodium tions were used to determine the monomer ratios in
metabisulfite (0.2 wt % monomer) solutions were the copolymers (Table I). The differences between the
added slowly. The reaction was then allowed to occur two results could be rationalized by a consideration of
at 25°C for 6 h. The final solution was clear and highly the moisture contents of the samples (obtained from
viscous. The solution was diluted to 2–3 times its thermogravimetry data shown later in Table IV). The
1
volume. A part of the polymer was then isolated H-NMR and IR data of the samples are presented in
by precipitation with acetone and dried in vacuo for Tables II and Table III, respectively. As expected, both
10 –15 h. the 1H-NMR and IR spectra confirmed the presence of
The acid content in the copolymer was then deter- different monomers in the copolymers. A typical pre-
mined by the potentiometric titration method. The sentation of the 1H-NMR and IR spectra of one of the
remaining part of the reaction mixture was neutral- copolymers is shown in Figure 1(a,b).
CHARACTERIZATION OF ACRYLAMIDE POLYMERS 1871

TABLE II
1
H-NMR Data and Interpretation
Sample 1 Sample 2 Sample 3 Sample 4
␦ Interpretation ␦ Interpretation ␦ Interpretation ␦ Interpretation

1.52 OCH2O 1.33 OCOCH3 1.61 OCH2O 1.59 OCOCH3

P P
CH3 CH3

2.08 OCHO 1.53 OCH2O 2.17 OCHO 1.69 OCH2O

P
CAO 1.70 OCH2OSO3O 2.88 CH3 2.27 OCHO
2.94
}
ON
{
CH3
2.27 OCHO 3.01 CH3
3.08
}
3.19
ON
{
CH3

Thermogravimetric analysis (TGA) NNDAM–AA copolymer was not detectable from

DTA [Fig. 1(c)]. There was no indication of a small,
The application of thermogravimetric tools such as
sudden endothermic change in the DTA thermogram
differential thermal analysis (DTA), TGA, and differ-
of the polymer.
ential thermogravimetry (DTG) is very significant in
Tg of a copolymer depends on several factors, phys-
characterizing a polymer.11–14 The data in Table IV
ical and chemical.14,16 –18 Previously, it was thought to
present the thermogravimetry (DTA, TGA, and DTG)
depend on the physical properties of the homopoly-
of all four polymers. In the DTA thermograms, no
mers composed of the comonomers of the copoly-
detectable crystallinity was observed in any of the four
mer.19 The properties include the specific volume, mo-
samples. This observation was also supported by the
lecular cohesive energy, and chain stiffness. Consider-
XRD spectra of the samples, indicating no crystallin-
ing these properties, Fox proposed the following
ity. All the polymer samples had low decomposition
equation:19
temperatures. The glass-transition temperatures (Tg’s)
of the samples were determined from the DTA ther-
mograms.15 As presented in Table IV, Tg of the 1/T gC ⫽ W A /T gA ⫹ W B /T gB

TABLE III
IR Data and Interpretation
Sample 1 Sample 2 Sample 3 Sample 4
⫺1 ⫺1 ⫺1 ⫺1
Peak (cm ) Interpretation Peak (cm ) Interpretation Peak (cm ) Interpretation Peak (cm ) Interpretation

3420 (b) N™H and 3440 (b) N™H and O™H 3416 (b) O™H str. 3440 (b) N™H and O™H
O™H str. str str.
2930 (w) C™H str. 2925 (w) C™H str. 2870 (w) C™H str. 2944 (w) C™H str.
1625 (s) C¢O str. of 1° 1678 (s) C¢O str. of 2° 1628 (s) C¢O str. of 3° 1638 (s) C¢O str. of 3°
amide amide amide amide
1596 (s) O™C™O⫺ str. 1647 (s) C¢O str. of 1° 1592 (s) O™C™O¢ str. 1610 (s) C¢O str. of 2°
amide amide
1377 (m) ™CH2™ ben. 1417 (m) ™C™H ben. of 1388 (m) C™H ben. of 1380 (m) C™H ben. of
™CH2™ gem-dimethyl gem-dimethyl
1342 (m) ™C™H ben. 1385 (m) C™H ben. of 1354 (m) C™H ben. of 1348 (m) C™H ben. of
gem-dimethyl ™CH2™ ™CH2™
1065 (w) ™SO3⫺ 1175 (w)
1140 (w) 1034 (m) ™SO3⫺
str: stretching vibration, ben: bending vibration.
1872 SABHAPONDIT, BORTHAKUR, AND HAQUE

Figure 1 (a) 1H-NMR spectra of polymer 2; (b) IR spectra of polymer 2; and (c) DTA, TGA, and DTG thermograms of
polymer 3.
CHARACTERIZATION OF ACRYLAMIDE POLYMERS 1873

Figure 1 (Continued from the previous page)

where TgC, TgA, and TgB are the glass-transition tem- Table IV shows that polymers 1 and 4 had compa-
peratures of copolymer C and homopolymers A and B rable Tg’s, whereas polymer 2 had a lower Tg. How-
(which comprise C), respectively, and WA and WB are ever, these were random copolymers with different
the weight fractions of comonomers A and B in co- monomer compositions. Therefore, it was extremely
polymer C. With this equation, the Tg values of all four difficult to explain their secondary phase-transition
copolymers (Table IV) were calculated. The deviation behavior, such as the glass transition, which depended
from the experimental values can be rationalized by a on several chemical and physical factors. Still, Tg data
consideration of the chemical effects of the func- can indicate the most ordered and stiffest arrangement
tional groups of the comonomers. For copolymers, of macromolecules in sample 4.
Johnston20 proposed a modified equation relating a All four copolymers showed more than one decom-
copolymer’s Tg to its composition. However, this is position temperature in DTG and DTA thermo-
out of the scope of this work and, therefore, is not grams.21 With increasing temperature, there was
discussed. breakage of the bonds in the copolymers, resulting in

TABLE IV
DTA, TGA, and DTG Data

Tg (°C) Decomposition temperature (°C) from DTG peak

(with % weight lost)
Moisture From From Fox
Sample content (wt %) DTA equationa T1 T2 T3 T4 T5

1 12 235 186 246 (8%) 320 (6%) 358 (6%) 369 (7%) 390 (10%)
2 12 205 116 280 (10%) 310 (11%) 376 (24%) 459 (15%) 544 (13%)
3 11 — 116 336 (4%) 381 (24%) 398 (11%) 410 (9%) 463 (6%)
4 8 239 85 238 (3%) 275 (4%) 316 (9%) 360 (24%) 522 (20%)
a
The Tg values of polyamide, poly(sodium acrylate, and poly(N,N-dimethylacrylamide) were obtained from ref. 25
whereas that for poly(sodium-2-acrylamide-2-methylpropane sufonate) was determined from DTA.
1874 SABHAPONDIT, BORTHAKUR, AND HAQUE

Figure 2 (a) NaCl, (b) CaCl2, and (c) MgCl2 䡠 4H2O concentration dependence of the aqueous solution viscosity of a 0.2%
solution of the polymers at 7.32 s⫺1 and 25°C.

the elimination of different types of gases, such as tion of absorbed moisture. The values of the moisture
CO2, SO2, CO, and NH3. Five different decomposition content (Table IV) support the deviation of the mono-
temperatures, indicated by DTG peaks along with the mer composition data determined potentiometrically
weight percentage lost, were considered for the eval- from those data obtained from 1H-NMR. It can be
uation of the thermal behavior of the copolymers (Ta- observed in Table IV that all the decomposition tem-
ble IV). Before proceeding to a higher temperature in peratures of AM–AMPS decreased on the replacement
thermogravimetric experiments, each sample was of AM with NNDAM. However, all the decomposition
heated to 150°C at a uniform heating rate and kept temperatures of AM–AA increased on the replace-
there isothermally for 5 min for the complete elimina- ment of AM with NNDAM.
CHARACTERIZATION OF ACRYLAMIDE POLYMERS 1875

Figure 2 (Continued from the previous page)

Rheological behavior consideration of the polyelectrolyte behavior of the

copolymers in brine-free water. With an increasing
Effect of the brine concentration on the cation concentration in the solution, the stretched
solution viscosity
polyelectrolyte chain started shrinking because of a
It can be observed in Figure 2(a– c) that the effect of reduction in intra-anionic electrostatic repulsion. At
Ca2⫹ and Mg2⫹ was much stronger than that of Na⫹ a certain salt concentration, the amount of cations
in reducing the solution viscosity of all four copol- present was sufficient to complete the shrinking,
ymer solutions. In each case, the viscosity decreased making the copolymer behave like a nonelectro-
to a certain concentration of added salt and then lyte.22 Therefore, beyond that salt concentration, the
remained constant, even on the addition of more addition of salt could not reduce the viscosity more,
salts to the solution. This can be explained by a and this is typical of a nonelectrolyte.

Figure 3 Shear rate dependence of the apparent viscosity of a 0.8% aqueous solution of the polymers at 25°C (logarithmic
scale).
1876 SABHAPONDIT, BORTHAKUR, AND HAQUE

TABLE V The values of n (⬍1) supported non-Newtonian thix-

Power-Law Constants for Copolymers at 25°C otropic behavior, whereas the values of K (decreasing
(Polymer Concentration ⴝ 0.8%)
from polymer 1 to polymer 4) indicated the higher
Power-law apparent viscosity of a solution of an identical poly-
constant Sample 1 Sample 2 Sample 3 Sample 4 mer concentration.23 It may be mentioned that a
K (mPa sn) 8454.73 4704.35 2795.76 1537.45 higher apparent viscosity in a brine-free aqueous so-
n 0.2336 0.2795 0.4065 0.4342 lution of a polyelectrolyte is of no importance if it has
a lower relative resistance factor in brine water than
another polyelectrolyte of a lower apparent viscosity
Except for polymer 1, the minimum viscosity ob- in brine-free water with a higher relative resistance
tained by the addition of salt was comparable for all factor in brine water.24
three cations: Ca2⫹, Mg2⫹, and Na⫹. However, for It can observed from Figure 3 that polymer 1 was
polymer 1, the solution viscosity decreased to a larger more shear-sensitive than the other polymers. In fact,
extent in the presence of bivalent cations than in the polymer 4 was more shear-resistant than the other
presence of monovalent cations. This can be explained polymers. The shear resistance of polymer 2 was com-
by the fact that polymer 1 formed complexes with the parable to that of polymer 1, whereas the shear resis-
bivalent ions, which were precipitated consequently tance of polymer 3 was comparable to that of polymer
on further addition. However, no precipitation was 4. This may support the fact that the presence of
observed with the addition of excess bivalent ions in hydrophobic groups in polymers 3 and 4 could con-
the other three polymer solutions. Because of the re- tribute to the shear resistance of aqueous polymer
placement of OCO⫺ ⫺
2 by OSO3 in polymers 2 and 4, solutions.
the polymer solutions were compatible with bivalent In another experiment, all four polymer solutions
ions. Although OCO⫺ 2 was present in polymer 3, the were continuously sheared at a constant shear rate for
bulky N,N-dimethyl group was responsible for the a long period of time. After the withdrawal of shear,
compatibility of the polymer solution with bivalent the polymer solutions were allowed to stand for a
ions. period. All the polymer solutions exhibited time-de-
pendent thixotropic behavior under shear (Fig. 4).
Polymers 2– 4 partially regained viscosity after aging
Effect of the shear on the solution viscosity
for some time after the withdrawal of shear. However,
It is apparent from Figure 3 that all the copolymer the viscosity of polymer 1 decreased further, even
solutions showed non-Newtonian shear-thinning be- after the withdrawal of shear, and never gained vis-
havior obeying a power law (Table V), at least within cosity again. When the polymer solution was contin-
the experimental range of the shear rate (1–1312 s⫺1). uously sheared at a constant shear rate, the intramac-

Figure 4 Time-dependent hysteresis loop for a 0.02% aqueous solution under dynamic (dashed lines; constant shear rate
⫽ 36.72 s⫺1) and static (bold lines) conditions at 30°C.
CHARACTERIZATION OF ACRYLAMIDE POLYMERS 1877

Figure 5 Time-dependent hysteresis loop for polymer 4 (0.02%) in a 0.01% NaCl solution under dynamic (dashed line;
constant shear rate ⫽ 36.72 s⫺1) and static (bold line) conditions at 36.72 s⫺1 and 30°C.

roion interaction between the charged ions progres- shearing and, therefore, the reduction in viscosity on
sively diminished, showing a reduction in the shearing. Experimentally, it was verified for polymer 4
hydrodynamic volume of the polymer and causing a (Fig. 5): a slight decrease in viscosity occurred tempo-
decrease in the apparent viscosity with time. If the rarily, but the viscosity was regained fully after the
polymer solution was sheared for a long period, the withdrawal of shear.
rate of the reformation of the structure of the polymer
could increase with time as the possibility of new
structural linkages increased.23 After a certain period, Effect of high-temperature aging on the
solution viscosity
a dynamic equilibrium was reached, beyond which
only the equilibrium viscosity was observed. Among The thermal stability of the polymer solutions were
polymers 2– 4, the amount of viscosity regained was studied by aging at 120°C under a nitrogen atmo-
highest in 4, less in 3, and least in 2; this order may sphere for a period of 1 month. It can be observed
also support the contribution of the hydrophilic group from Table VI that polymer solutions of comparable
to shear resistance. In addition, the stronger hydrogen concentrations differed in their stability. Polymer 1
bonding ability of the OSO⫺ 3 group should have lost efficacy very fast. The replacement of the AA
helped with the reformation of the structures in poly- group of polymer 1 by AMPS in polymer 2 improved
mers 2 and 4 during shearing, which should have been the stability slightly but not sufficiently. The same
less in polymers 1 and 3 because they had the OCO⫺ 2 extent of improvement was obtained by the replace-
group instead of OSO⫺ 3. ment of the other monomer, AM, by NNDAM in
In the presence of brine, the macroions shrank and polymer 3. This showed that monomers AA and AM
became more like spheres than a stretched chain. This were equally responsible for the low thermal stability
helped in resisting the deformation of the structure on of the copolymers. For a further improvement in the

TABLE VI
Effect of High-Temperature Aging on Solution Viscosity
Solution viscosity (cp) at 1312 s⫺1 and 25°C after aging at 120°C for
Sample no 0 1 4 6 8 10 15 20 25 30
(in 0.8% aqueous solution) days day days days days days days days days days

1 39.2 8.0 7.0 — — — — — — —

2 31.6 12.3 7.5 6.0 — — — — — —
3 28.0 15.1 8.0 6.0 — — — — — —
4 29.9 26.5 23.9 22.0 21.6 21.0 19.8 19.6 19.4 19.3
1878 SABHAPONDIT, BORTHAKUR, AND HAQUE

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placed by NNDAM and AMPS, respectively, in poly- 3769.
5. Borchardt, J. K. In Encyclopedia of Polymer Science and Tech-
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2000, 32, 133.
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