# US 11,441,065 B2 · Combination of a sulfonated surfactant composition and star macromolecules

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- Number: US 11,441,065 B2
- Document ID: US11441065B2
- Status: Granted
- Kind: B2
- Application number: 16/338,864
- Filed: 2017-10-03
- Published: 2021-09-16
- Granted: 2022-09-13
- Earliest claimed: 2016-10-04
- Assignees: Pilot Polymer Technologies, Inc.
- Applicants: Pilot Polymer Technologies, Inc.
- Inventors: Yuanxi Liao; Patrick McCarthy; Liang Huang; Donald Bogus
- Web page: https://patentgrep.com/patent/US11441065B2

## CPC

- C08F 20/18: with acrylic or methacrylic acids
- C09K 8/588: characterised by the use of specific polymers {(polymeric surfactants C09K8/584)}
- C08F 293/005: {using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent}
- C08K 5/36: Sulfur-, selenium-, or tellurium-containing compounds {(C08K5/0091 takes precedence)}
- C09K 8/584: characterised by the use of specific surfactants
- C11D 1/22: derived from aromatic compounds
- C11D 1/24: containing ester or ether groups directly attached to the nucleus
- C11D 3/3788: {Graft polymers}
- C08F 2438/01: Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

The present invention relates to a composition comprising at least one sulfonated surfactant composition and one or more multi-arm star macromolecules having a core and a plurality of polymeric arms, and methods of preparing and using the same. In one aspect of the invention, this composition is capable of increasing the viscosity, and/or temperature-stability to an aqueous system.

## Claims

### Claim 1

A composition comprising at least one sulfonated surfactant composition and one or more star macromolecules having a core and a plurality of polymeric arms, wherein:
a) at least one polymeric arm of the plurality of polymeric arms is a hydrophilic polymeric arm;
b) at least one polymeric arm of the plurality of polymeric arms is a copolymeric arm, wherein the at least one copolymeric arm:
1) comprises a longer hydrophilic segment proximal to the core and a shorter hydrophobic segment distal to the core; and
2) has a greater degree of polymerization than the at least one hydrophilic polymeric arm; and
wherein the at least one sulfonated surfactant composition comprises a disulfonated surfactant composition represented by Formula II or Formula III:
wherein:
R1 —represents a hydrogen, or a linear or branched C6-C24 alkyl;
R2 —represents a hydrogen, or a linear or branched C6-C24 alkyl;
R3 —represents a hydrogen, or a linear or branched C6-C24 alkyl;
M—represents an alkali metal, an ammonium represented by N(R4)4, or an aminoalcohol, or SO3M is SO3H; wherein R4 independently represents a hydrogen, or a linear or branched C3-C6 alkyl;
m—represents an integer of 1 or 2; and
n—represents an integer of 0 or 1; and
wherein at least one and no more than two of R1, R2, and R3, represents a linear or branched C6-C24 alkyl.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the composition is a gel or a fluid.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the composition is used as an oilfield chemical.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the at least one sulfonated surfactant composition comprises any mixture of any number of the following: C10 (Linear) Sodium Diphenyl Oxide Disulfonate, C16 (Linear) Sodium Diphenyl Oxide Disulfonate, C6 (Linear) Diphenyl Oxide Disulfonic Acid, C12 (Branched) Sodium Diphenyl Oxide Disulfonate, C12 (Branched) Diphenyl Oxide Disulfonic Acid, and C12 (Branched) Diphenyl Oxide Disulfonic Acid.

### Claim 5 (depends on 1)

The composition of claim 1, wherein when 1.0 wt. % of the star macromolecule and 0.3 wt. % of the at least one sulfonated surfactant composition forms a homogeneous gel and has a dynamic viscosity of at least 50 cP at a shear rate of 100 s−1 at 75° F., according to the Surfactant with KCl Compatibility Test.

### Claim 6 (depends on 1)

The composition of claim 1, wherein when 1.0 wt. % of the star macromolecule and 0.3 wt. % of the at least one sulfonated surfactant composition forms a homogeneous gel and has a dynamic viscosity of at least 50 cP at a shear rate of 100 s−1 at 75° F., according to the Surfactant with KCl Compatibility Test, and has a Dynamic Viscosity at 200° F. that is at least 50% relative to the viscosity of the gel at 75° F., according to the Temperature Stability Test.

### Claim 7 (depends on 1)

The composition of claim 1, wherein when 2.0 wt. % of the star macromolecule and 5.0 wt. % of the at least one sulfonated surfactant composition forms a homogeneous gel and has a dynamic viscosity of at least 30,000 cP in 5.0 wt. % sulfonated surfactant composition aqueous solution at a shear rate of 0.22 s−1 at 25° C., according to the Surfactant Compatibility Test.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the at least one sulfonated surfactant composition comprises 2-100 wt. % of an anionic sulfonated surfactant.

### Claim 9 (depends on 1)

The composition of claim 1, further comprising a chloride salt.

### Claim 10 (depends on 9)

The composition of claim 9 has a salinity of about 2% or greater.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the moiety represented by SO3M is not SO3H.

### Claim 12 (depends on 1)

The composition of claim 1, wherein M represents an alkali metal.

### Claim 13 (depends on 1)

The composition of claim 1, wherein M represents N(R4)4.

### Claim 14 (depends on 13)

The composition of claim 13, wherein at least one R4 independently represents a hydrogen.

### Claim 15 (depends on 13)

The composition of claim 13, wherein at least one R4 independently represents a linear or branched C3-C6 alkyl.

### Claim 16 (depends on 1)

The composition of claim 1, wherein M represents an aminoalcohol salt.

### Claim 17 (depends on 1)

The composition of claim 1, wherein at least one of the one or more star macromolecules is represented by Formula A:
[(P1)q1−(P2)q2]t−Core−[(P3)q3]r Formula A
wherein:
Core represents a crosslinked polymeric segment;
P1 represents a hydrophobic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;
P2 represents a hydrophilic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;
P3 represents a hydrophilic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;
q1 represents the number of repeat units in P1 and has a value between 1 and 50;
q2 represents the number of repeat units in P2 and has a value between 30 and 2000;
q3 represents the number of repeat units in P3 and has a value between 5 and 2000;
r represents the number of block copolymeric arms covalently attached to the Core;
t represents the number of polymeric arms covalently attached to the Core; and wherein the molar ratio of r to t is in the range of between 40:1 and 2:1.

### Claim 18 (depends on 1)

The composition of claim 1, wherein at least one of the one or more star macromolecules is a surfactant-system thickening macromolecule.

### Claim 19 (depends on 1)

The composition of claim 1, wherein at least one of the one or more star macromolecules is a surfactant-system thickening macromolecule represented by Formula B:
wherein:
Core represents a crosslinked polymeric segment;
P1 independently represents a polymeric segment of a first polymeric arm comprised of monomeric residues of polymerized hydrophilic monomers;
P2 independently represents a further segment of a second polymeric arm comprised of at least one monomeric residue of a polymerized hydrophobic monomer;
P3 independently represents a polymeric segment of the second polymeric arm comprised of monomeric residues of polymerized hydrophilic monomers;
P4 independently represents a polymeric segment of a third polymeric arm comprised of monomeric residues of polymerized hydrophobic monomers;
P5 independently represents a polymeric segment of the third polymeric arm comprised of monomeric residues of polymerized hydrophilic monomers;
q1 independently represents the number of monomeric residues in P1 and has a value between 5 and 2000;
q2 independently represents the number of monomeric residues in P2 and has a value between 1 and 500;
q3 independently represents the number of monomeric residues in P3 and has a value between 10 and 5000;
q4 independently represents the number of monomeric residues in P4 and has a value between 1 and 500;
q5 independently represents the number of monomeric residues in P5 and has a value between 0 and 5000;
r independently represents the number of the first polymeric arms covalently attached to the Core and has a value in the range of from 1 to 1000;
s independently represents the number of the second polymeric arms covalently attached to the Core and has a value in the range of from 1 to 1000;
t independently represents the number of the third polymeric arms covalently attached to the Core and has a value in the range of from 0 to 1000; and
wherein the ratio of r:s, and, if t is not zero, the ratio of r:t, t:s, and r:(s+t), are independently in the range of between 40:1 and 1:40.