IP Library Granted Patent US 10,556,975
Granted Patent B2
US 10,556,975 · App. 15/663,026 · Granted Feb 11, 2020

Aqueous polymerization of thermoresponsive flocculants

Inventor: Paula Delgado (Bartlesville, OK)
Assignee: Phillips 66 Company
C08F20/36C02F1/56C08F20/56C08F220/34C08F220/56
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Quick Facts
Patent No.
US 10,556,975
App. No.
15/663,026
Granted
Feb 11, 2020
Kind
B2
Abstract

A method of forming a thermoresponsive polymer. The method begins by forming a monomer solution by mixing and an optional water soluble monomer in the presence of an aqueous solution. An initiator is then added to the monomer solution to form a thermoresponsive polymer. In this method, R1 can be independently selected from the group consisting of H and alkyl groups; Y can be selected from the group consisting of O, N and S; R2 and R3 can be independently selected from the group consisting of H, alkyl, olefinic, heterocyclic, aromatics, halogens, ammonium salts, nitroxides, nitrates, nitrites, amines, amides, carboxylic acidsacyl chlorides, esters, ethers, alcohols, nitriles, phosphates, phosphonates, sulfates, sulfonates, sulfides, sulfites, thiols, and combinations thereof; and X are methylene groups from about 0 to about 20 carbons.

Claims (49)

1. A method comprising:

forming a monomer solution by mixing formula

and a water soluble monomer in the presence of an aqueous solution;

adding an initiator to the monomer solution to form a thermoresponsive polymer, wherein:

R1 is independently selected from the group consisting of H and alkyl groups;

R2 and R3 are independently selected from the group consisting of H, alkyl, olefinic, aromatics, heterocyclic, halogen, ammonium, nitroxides, nitrates, nitrite amides, amines, esters, ethers, carboxylic acids, acyl chlorides, alcohols, nitriles, phosphates, phosphonates, sulfates, sulfonates, sulfide, sulfite, thiol, and combinations thereof;

Y is selected from the group consisting of O, N and S;

X are methylene groups containing from about 0 to about 20 carbons, and

wherein the aqueous solution is an aqueous salt solution.

2. The method of claim 1 , wherein the water soluble monomer is selected from the group consisting of: monofunctional acrylic monomers, multifunctional acrylic monomers, monofunctional vinyl monomers, multifunctional vinyl monomers and combinations thereof.

3. The method of claim 1 , wherein monomer solution is heated to a temperature greater than 50° C.

4. The method of claim 1 , wherein monomer solution is heated to a temperature greater than 85° C.

5. The method of claim 1 , wherein the initiator is an addition-type initiator.

6. The method of claim 1 , wherein the initiator is selected from the group consisting of: azo initiators, peroxide initiators, persulfate initiators and combinations thereof.

7. The method of claim 6 , wherein the peroxide initiator is selected from the group consisting of: persulfate salts, hydrogen peroxide, alkyl peroxide, alkyl peroxyesters, peroxydicarbonates, hydroperoxides and combinations thereof.

8. The method of claim 6 , wherein the azo initiator is selected from the group consisting of: 4,4′-azobis(4-cyanovaleric acid), 4,4′-azobis-(4-cyanopentanoic acid), 2,2′-azobis(2-methylpropionamidine)dihydrochloride, 2,2′-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, 2,2′-azobis[N-(2-carboxyethyl)-2-methylpropionamidine] tetrahydrate, 2,2′-azobis[2-(2-imidazolin-2-yl)propane], 2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2′-azobis-(2-amidinopropane)dihydrochloride, 2,2′-azobis(N,N′-dimethylene isobutyramidine) dihydrochloride, 2,2′-zobis(N,N′-dimethylene isobutyramidine), 2,2′-azobis-(isobutyramide)dehydrate, 2,2′-azobis-(N-ethylamidinopropane hydrochloride), 2,2′-azobis-(N,N′-dimethyleneamidinopropane hydrochloride), 2,2′-azobis(2-propane-2-carboxylic acid), 2,2′-azobis-(2-methyl-N-(2-hydroxyethyl))propionamide, 2,2′-azobis-[2-methyl-N-(1,1-bis(hydroxymethyl)]propionamide, 2,2′-azobis-[2-methyl-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)]propionamide and combinations thereof.

9. The method of claim 1 , wherein the initiator is azobis(2-methylpropionamidine) dihydrochloride.

10. The method of claim 1 , wherein the water soluble monomer is acrylamide.

11. The method of claim 1 , wherein the mixing of monomer solution occurs at an elevated temperature.

12. The method of claim 11 , wherein the elevated temperature is greater than 50° C.

13. The method of claim 1 , wherein the thermoresponsive polymer is water soluble.

14. The method of claim 1 , wherein the thermoresponsive polymer has an average molecular weight greater than 50,000.

15. A method comprising:

forming a monomer solution by mixing formula

and a water soluble monomer in the presence of an aqueous solution;

adding an initiator to the monomer solution to form a thermoresponsive polymer, wherein:

R1 is independently selected from the group consisting of H and alkyl groups;

R2 and R3 are independently selected from the group consisting of H, alkyl, olefinic, aromatics, heterocyclic, halogen, ammonium, nitroxides, nitrates, nitrite amides, amines, esters, ethers, carboxylic acids, acyl chlorides, alcohols, nitriles, phosphates, phosphonates, sulfates, sulfonates, sulfide, sulfite, thiol, and combinations thereof;

Y is selected from the group consisting of O, N and S;

X are methylene groups containing from about 0 to about 20 carbons, and

wherein the aqueous solution is brackish water.

16. A method comprising:

forming a monomer solution by mixing formula

and a water soluble monomer in the presence of an aqueous solution;

adding an initiator to the monomer solution to form a thermoresponsive polymer, wherein:

R1 is independently selected from the group consisting of H and alkyl groups;

R2 and R3 are independently selected from the group consisting of H, alkyl, olefinic, aromatics, heterocyclic, halogen, ammonium, nitroxides, nitrates, nitrite amides, amines, esters, ethers, carboxylic acids, acyl chlorides, alcohols, nitriles, phosphates, phosphonates, sulfates, sulfonates, sulfide, sulfite, thiol, and combinations thereof;

Y is selected from the group consisting of O, N and S;

X are methylene groups containing from about 0 to about 20 carbons, and

wherein the aqueous solution is saline water.

17. A method comprising:

forming a monomer solution by mixing formula

and a water soluble monomer in the presence of an aqueous solution;

adding an initiator to the monomer solution to form a thermoresponsive polymer, wherein:

R1 is independently selected from the group consisting of H and alkyl groups;

R2 and R3 are independently selected from the group consisting of H, alkyl, olefinic, aromatics, heterocyclic, halogen, ammonium, nitroxides, nitrates, nitrite amides, amines, esters, ethers, carboxylic acids, acyl chlorides, alcohols, nitriles, phosphates, phosphonates, sulfates, sulfonates, sulfide, sulfite, thiol, and combinations thereof;

Y is selected from the group consisting of O, N and S;

X are methylene groups containing from about 0 to about 20 carbons, and

wherein the aqueous solution is brine water.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2017
From: DELGADO, PAULA; PALKAR, AMIT
To: PHILLIPS 66 COMPANY
Reel/Frame 043762/0405 →
Continuity (2)
Provisional Application 62393900 · Sep 13, 2016
Related Publication 20180072825A1 · Mar 15, 2018