Polyacrylamide and its derivatives for oil recovery


Table 4  Summary of some typical co-monomers to modify the PAMs. Structure



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Polyacrylamide and its derivatives for oil recovery

Table 4 
Summary of some typical co-monomers to modify the PAMs.
Structure 
Initiator 
Surfactant 
Comments 
Ref. 
Solution polymerization 
 
K2S2O8TEMED/ 
(N,N,N,N-
tetramethylethylenediamin
e) 
Zwitterionic sulfobetaine 
polymer 
[68] 
 
(NH4)2S2O8 

Through this method, the 
production is pure 
without surfactants. 
[69] 


63
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
 
K2S2O8 
SDS 
Good resistance to aging 
due to simultaneous 
incorporation of bulky 
side groups 
[77] 
 
(NH
4
)
2
S
2
O
8
and sodium 
metabisulfite 

Thermally stable at 
120 °C at least for a 
period of 1 month. 
[127] 
 
 
 
 
 
*
C
N
H
3
C
CH
3
O
NH
C
CH
2
O
CH
3
H
3
C
S
O
O
ONa


64
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
 
K
2
S
2
O
8
without extra 
surfactant added; 
AIBN with extra 
surfactant added. 
Cationic 
surfactant 
Microblocky structures; 
[34] 
C
NH
2
O
CH
2
CH
2
N
CH
3
H
3
C
CH
3
Br
12
C
NH
2
O
CH
2
N
CH
2
CH
3
H
3
C
CH
3
Cl
11
 
AIBN 
Polymerizable 
surfactant 
Hydrophobically 
modified polyacrylamide 
[351] 
 
 
 
 
 
 
 
C
NH
2
C
NH
CH
2
N
C
12
H
25
O
O
CH
3
H
3
C
*
Br


65
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
C
C
NH
2
ONa
O
O
O
O
O
OH
10
 
(NH
4
)
2
S
2
O
8
–NaHSO
3
O
O
O
OH
10
Self-polymerizable 
surfactant; the copolymer 
solution showed a good 
ability to emulsify 
organic components. 
[352] 
Telechelic Structure: 
O
O
O
O
CN
CN
NH
2
NH
11
11
O
O
n
Multisticker Structure: 
OH
OH
O
CN
CN
O
NH
2
NH
N
O
O
O
5
5
n
 
Azobis(4-cyanopentanoic 
acid) (ACVA) 
SDS 
Three different types of 
associative watersoluble 
polymers were prepared by 
a free radical solution 
polymerization. (telechelic, 
multisticker and combined 
polymers) 
[162] 


66
Table 4 
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
Combined structure:
O
O
O
CN
CN
O
NH
2
NH
N
O
O
O
5
5
n
11
11
 
C
C
CH
2
NH
2
ONa
O
CH
2
CH
2
O
R
O
O
n
 
K
2
S
2
O
8
/NaHSO
3

Comb-shaped 
[29] 
C
NH
2
CH
2
O
C
ONa
O
O
 
K
2
S
2
O
8
/NaHSO
3

Inclusion property. 
[184] 
 


67
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
C
NH
2
C
NH
CH
2
N
CH
2
SO
3
Na
O
O
CH
3
H
3
C
Cl
3
3
C
NH
2
C
NH
C
CH
2
SO
3
Na
O
O
CH
3
H
3
C
 
K
2
S
2
O
8

zwitterionic 
polyacrylamide 
[185] 
 
 
 
 


68
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
N
C
NH
2
CH
2
SO
3
O
3
 
K
2
S
2
O
8
/NaHSO
3
zwitterionic 
polyacrylamide 
[191] 
C
NH
2
C
ONa
C
NH
CH
2
CH
2
N
C
12
H
25
H
3
C
CH
3
O
O
O
Br
 
2,2’-Azobis[2-(2-
imidazolin-2-yl)propane] 
dihydrochloride (VA-044) 

Hydrophobically 
associating 
[196] 
PAM-Al(OH)
3
 hybrid polymer 
(NH
4
)
2
S
2
O
8
/NaHSO
3

Hybrid PAM 
[24, 206] 
 
 
 


69
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.) 
 
Micellar Co-Polymerizaton 
 
K
2
S
2
O
8
Sodium 
Dodecyl 
Benzene 
Sulfonate(SDB
S), 
cetyltrimethyla
mmonium 
bromide 
(CTAB) 
Tree-like structure will 
form with increasing 
NaCl concentration, 
[70] 
 
K
2
S
2
O
8
/ NaHSO
3

Amphiphilic 
polyacrylamide 
[78] 
 
Hydrophobic Synthesized 
initiator with a long linear 
chain (C16) 
SDS 
Combined thermally 
insensitive polymer 
[79]


70
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
C
C
NH
2
O
CH
2
N
CH
2
CH
3
O
O
H
3
C
CH
3
Cl
15
2
 
V-50 (2,2-azobis(2-
amidinopropane)dihydroch
loride) 
C
O
CH
2
N
CH
2
CH
3
O
CH
3
Cl
15
2
H
3
C

SDS 
Ionic modified polymer 
[81] 
C
NH
2
O
C
CH
3
H
3
C
CH
3
 
K
2
S
2
O
8
SDS 
Hydrophobic acrylamide-
modified copolymers;
good anti-aging property 
in brine solutions at 80°C 
[147] 
 
 
 


71
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
C
NH
2
O
NH
C
O
C
N
O
CH
H
2
C
CH
2
CH
3
CH
3
H
3
C
CH
3
5
5
 
4,4’-azobis(4-
cyanopentanoic acid) 
(ACVA) 
SDS 
Thermal insensitive 
hydrophobically 
modified polyacrylamide 
[213] 
C
NH
2
O
NH
C
O
C
N
O
CH
2
11
CH
3
CH
2
H
2
C
CH
2
CH
2
CH
3
CH
3
10
10
C
NH
HC
CH
2
CH
3
O
10
H
2
C
SO
3
Na
 
K
2
S
2
O
8
C
NH
HC
CH
2
CH
3
O
10
H
2
C
SO
3
Na
Polymerizable 
surfactants 
[159] 
 
 
 
 
 
 
 


72
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.) 
 
 
 
AMPS 
SDS 
Hydrophobically 
modified polyacrylamide 
[163] 
 
K
2
S
2
O
8
SDS 
Hydrophobically 
associating acrylamide-
modified terpolymers 
containing both cationic 
groups and hydrophobic 
segments 
cationic groups and 
hydrophobic segments 
[164] 
Inverse Emulsion Polymerization 
 
AIBN, BPO, K
2
S
2
O
8
Tween85; 
Span 80 
[84] 
C
NH
2
C
NH
C
CH
2
SO
3
O
O
H
3
C
CH
3
C
C
CH
2
NH
2
O
O
O
CH
2
N
H
3
C
CH
3
CH
3
2
Cl
2
C
NH
2
O


73
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.) 
 
 
K
2
S
2
O
8
/NaHSO
3
R
1
O
O
O
O
O
O
R
2
O
Polymerizable 
surfactants 
[353] 
Living Polymerization
 
MeClPr/CuCl/Me
6
TREN 
as the initiator/catalyst 
system 

Hydrophobically 
modified polyacrylamide 
[92] 
 
C
C
NH
2
O
O
O
O
23
O
O
R
2
R
1
O
H
3
C
Cl
C
O
CH
2
CH
3
C
stat
O
CH
2
CH
3
C
N
O
O
O
H
3
C CH
3
3


74
Table 4
Summary of some typical co-monomers to modify the PAMs. (Cont.)
 
 
Viz.2-chloropropionamide, 
(2-Cl-PA) or 2-
bromopropionamide (2-
Br-PA) and CuX (X ) Cl, 
Br) bipyridine complex 

The ATRP of acrylamide 
is achived achieved in 
glycerol-water medium 
at 130 ͦC using both Cl- 
and Br-based initiating 
system, in presence of 
CuX2 and alkli halides. 
[93] 
 
Stereospecific 
catalyst :Lewis acid 
Y(OTf)
3
or AlCl
3
Initiator:chloroacetic 
acidAcid/CuCl/N,N,N’,N’
-tetramethyl 
ethylenediamine 
(TMEDA) 

Low polydispersity index 
of 1.03 and high tacticity 
with meso content up to
76% at the optimal 
reaction condition. 
[94] 
 
Macroinitiator: PAM-Cl 

Branched high molecular 
weight of PAM. 
[95] 
C
NH
2
O
C
NH
2
O
C
NH
CH
H
3
C
O
CH
3
C
NH
CH
H
3
C
O
CH
3
C
NH
2
O
O
O


75
Table 4 
Summary of some typical co-monomers to modify the PAMs. (Cont.) 
 
 
Halogen-functionalized 
aliphatic polyketones 
[97] 
 
C
NH
C
S
O
C
HN
CH
2
CH
3
O
O
H
3
C
CH
3
O
O
9
Na
 
AIBN 

RAFT; micelle-forming, 
amphiphilic copolymers 
or “polysoaps” 
 
And (Me6TREN)/copper 
halogenide (CuX) as the 
catalyst 

Linear PAM with 
apparent molecular 
weights up to 
>150 000 g/mol and 
dispersities as low as 
1.39. 
[130] 
C
NH
2
O
C
NH
CH
H
3
C
O
CH
3
C
NH
2
O
C
NH
CH
H
3
C
O
CH
3
C
NH
2
O
O
O


76
Table 5 
Preparative Conditions for Cross-linked PAMs.
Monomer/Polymer
MetalIonomer 
Crosslinking Reagents
Initiator
Surfactant
Comments
Ref
Solution polymerization 
 
N-isopropyl 
acrylamide 
(NIPAM); 
acrylamide (AAm); 
crotonic acid; 
itaconic acid; 
aconitic acid; 
N,N-methylene 
bisacrylamide(Bis) 
(NH
4
)
2
S
2
O
8
+
TEMED 

Environmentally 
sensitive hydrogels 
responsive to various 
Stimuli such as 
temperature, pH, 
ionic strength of the 
medium 
[76] 
Polyacrylamide 
N,N-methylene 
bisacrylamide, PEG 
diacrylate 


Preformed particle 
gel(PPG) 
[46, 303-306] 
Polyacrylamide 
N,N-methylene 
bisacrylamide(Bis); 
Bentonite clay. 
Peroxide 
disulfate 

Preformed particle 
gel(PPG) 
[43, 214-218] 

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