CA2797758A1 - Water-soluble degradable synthetic vinyl polymers and related methods - Google Patents
Water-soluble degradable synthetic vinyl polymers and related methods Download PDFInfo
- Publication number
- CA2797758A1 CA2797758A1 CA2797758A CA2797758A CA2797758A1 CA 2797758 A1 CA2797758 A1 CA 2797758A1 CA 2797758 A CA2797758 A CA 2797758A CA 2797758 A CA2797758 A CA 2797758A CA 2797758 A1 CA2797758 A1 CA 2797758A1
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- water
- group
- vinyl polymer
- degradable synthetic
- soluble degradable
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/10—Aqueous solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
- C09K8/685—Compositions based on water or polar solvents containing organic compounds containing cross-linking agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/882—Compositions based on water or polar solvents containing organic compounds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/887—Compositions based on water or polar solvents containing organic compounds macromolecular compounds containing cross-linking agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/28—Friction or drag reducing additives
Abstract
Of the many embodiments presented herein, one is a subterranean treatment fluid comprising: an aqueous fluid; and a water-soluble degradable synthetic vinyl polymer having a labile link in its backbone. Also provided in one instance is a water-soluble degradable synthetic vinyl polymer with labile group in its backbone made by a redox polymerization, the redox polymerization reaction comprising these reactants: a macroinitiator that comprises a labile link, an oxidizing metal ion, and a vinyl monomer.
Claims (34)
1. A water-soluble degradable synthetic vinyl polymer with a labile group in its backbone made by a redox polymerization, the redox polymerization reaction comprising these reactants:
a macroinitiator that comprises a labile link, an oxidizing metal ion, and a vinyl monomer.
a macroinitiator that comprises a labile link, an oxidizing metal ion, and a vinyl monomer.
2. The water-soluble degradable synthetic vinyl polymer of claim 1 wherein the labile link comprises a labile group chosen from the group consisting of: an ester group, an amide group, a carbonate group, an azo group, a disulfide group, an orthoester group, an acetal group, an etherester group, an ether group, a silyl group, a phosphazine group, a urethane group, an esteramide group, an etheramide group, an anhydride groups, any derivative thereof, and any combination thereof.
3. The water-soluble degradable synthetic vinyl polymer of claim 1 or 2 wherein the labile link is derived from oligomeric or short chain molecules chosen form the group consisting of: a poly(anhydride), a poly(orthoester), an orthoester, a poly(lactic acid), a poly(glycolic acid), a poly(caprolactone), a poly(hydroxybutyrates), a polyphosphazine, a poly(carbonate), a polyacetal, a polyetheresters, a polyesteramides, a polycyanoacrylates, a polyurethane, a polyacrylate, and any derivative, copolymer, or combination thereof.
4. The water-soluble degradable synthetic vinyl polymer of claim 1, 2 or 3 wherein the labile link is derived from a hydrophilic polymeric block comprising at least one compound selected from the group consisting of: a poly(alkylene glycol), a poly(alcohol) made by the hydrolysis of poly(vinyl acetate), poly(vinyl pyrrolidone), a polysaccharide, a chitin, a chitosan, a protein, a poly(amino acid), a poly(alkylene oxide), a poly(amide), a poly(acid), a polyol, and any derivative, copolymer, or combination thereof.
5. The water-soluble degradable synthetic vinyl polymer of claim 1, 2, 3 or 4 wherein the water-soluble degradable synthetic vinyl polymer has a molecular weight in the range of about 500,000 to about 15,000,000.
6. The water-soluble degradable synthetic vinyl polymer of any preceding claim wherein the oxidizing metal ion comprises a metal ion chosen from the group consisting of.
cerium (IV), manganese (III), copper (II), vanadium (V), cobalt (III), chromium(VI), and iron (III).
cerium (IV), manganese (III), copper (II), vanadium (V), cobalt (III), chromium(VI), and iron (III).
7. The water-soluble degradable synthetic vinyl polymer of any preceding claim wherein the macroinitiator comprises a reducing group chosen from the group consisting of:
a hydroxide, an aldehyde, an amine, and an acid.
a hydroxide, an aldehyde, an amine, and an acid.
8. The water-soluble degradable synthetic vinyl polymer of any preceding claim wherein the water-soluble degradable synthetic vinyl polymer degrades by an action chosen from the group consisting of: oxidation, reducing agent, photo-degradation, thermal degradation, hydrolysis, and microbial degradation.
9. The water-soluble degradable synthetic vinyl polymer of any preceding claim wherein the water-soluble degradable synthetic vinyl polymer is crosslinked.
10. The water-soluble degradable synthetic vinyl polymer of any preceding claim wherein the vinyl monomer comprises a monomer chosen from the group consisting of:
acrylamide, vinyl acetate, 2-acrylamido-2-methylpropane sulfonic acid, N,N-dimethylacrylamide, vinyl pyrrolidone, dimethylaminoethyl methacrylate, acrylic acid, dimethylaminopropylmethacrylamide, vinyl amine, vinyl acetate, trimethylammoniumethyl methacrylate chloride, methacrylamide, hydroxyethyl acrylate, vinyl sulfonic acid, vinyl phosphonic acid, vinylbenzene sulfonic acid, methacrylic acid, vinyl caprolactam, N-vinylformamide, diallyl amine, N,N-diallylacetamide, dimethyldiallyl ammonium halide, itaconic acid, styrene sulfonic acid, methacrylamidoethyltrimethyl ammonium halide, quaternary salt derivatives of acrylamide, and quaternary salt derivatives of acrylic acid, alkyl acrylates, alkyl methacrylates, alkyl acrylamides, alkyl methacrylamides alkyl dimethylammoniumethyl methacrylate halides, alkyl dimethylammoniumpropyl methacrylamide halides, any derivative thereof, and any combination thereof.
acrylamide, vinyl acetate, 2-acrylamido-2-methylpropane sulfonic acid, N,N-dimethylacrylamide, vinyl pyrrolidone, dimethylaminoethyl methacrylate, acrylic acid, dimethylaminopropylmethacrylamide, vinyl amine, vinyl acetate, trimethylammoniumethyl methacrylate chloride, methacrylamide, hydroxyethyl acrylate, vinyl sulfonic acid, vinyl phosphonic acid, vinylbenzene sulfonic acid, methacrylic acid, vinyl caprolactam, N-vinylformamide, diallyl amine, N,N-diallylacetamide, dimethyldiallyl ammonium halide, itaconic acid, styrene sulfonic acid, methacrylamidoethyltrimethyl ammonium halide, quaternary salt derivatives of acrylamide, and quaternary salt derivatives of acrylic acid, alkyl acrylates, alkyl methacrylates, alkyl acrylamides, alkyl methacrylamides alkyl dimethylammoniumethyl methacrylate halides, alkyl dimethylammoniumpropyl methacrylamide halides, any derivative thereof, and any combination thereof.
11. A micelle having an outer layer comprising a water-soluble degradable synthetic vinyl polymer with labile group in its backbone and an enclosed chemical.
12. The micelle of claim 11 wherein the enclosed chemical comprises a chemical chosen from the group consisting of. an oxidizer, a chelator, an activator, and an acid-precursor.
13. A micelle according to claim 11 or 12 wherein the water-soluble degradable synthetic vinyl polymer is as defined in any one of claims 1 to 10.
14. An emulsion comprising an external phase, an internal phase, and an emulsion stabilizer that comprises a water-soluble degradable synthetic vinyl polymer with a labile group in its backbone.
15. The emulsion of claim 14 wherein the external phase is oil-based and the internal phase is aqueous-based.
16. The emulsion of claim 14 or 15 wherein the internal phase is oil-based and the external phase is aqueous-based.
17. The emulsion of claim 14, 15 or 16 wherein the emulsion stabilizer is present in an amount in the range of from about 0.025% to about 4% by weight of the external phase.
18. An emulsion according to claim 14, 15, 16 or 17 wherein the water-soluble degradable synthetic vinyl polymer is as defined in any one of claims 1 to 10.
19. A process for polymerizing one or more vinyl monomers to form a water-soluble degradable synthetic vinyl polymer, the process comprising:
contacting the vinyl monomer with a macroinitiator comprising a labile group and an oxidizing metal ion under redox polymerization conditions to produce a water-soluble degradable synthetic vinyl polymer with a labile group in its backbone.
contacting the vinyl monomer with a macroinitiator comprising a labile group and an oxidizing metal ion under redox polymerization conditions to produce a water-soluble degradable synthetic vinyl polymer with a labile group in its backbone.
20. A process according to claim 19 wherein the water-soluble degradable synthetic vinyl polymer is as defined in any one of claims 1 to 10.
21. A process according to claim 19 or 20 further comprising crosslinking the water-soluble degradable synthetic vinyl polymer in a reaction comprising a crosslinking agent.
22. A process according to claim 21 wherein the crosslinking agent is a metal crosslinking agent.
23. A subterranean treatment fluid comprising:
an aqueous fluid; and a water-soluble degradable synthetic vinyl polymer having a labile link in its backbone.
an aqueous fluid; and a water-soluble degradable synthetic vinyl polymer having a labile link in its backbone.
24. A subterranean treatment fluid according to claim 23 wherein the water-soluble degradable synthetic vinyl polymer is as defined in any one of claims 1 to 10.
25. The subterranean treatment fluid of claim 23 or 24 further comprising an additive chosen from the group consisting of: a corrosion inhibitor, a proppant particulate, an acid, a fluid loss control additive, a surfactant, a breaker, an iron-control inhibitor, a scale inhibitor, and a clay stabilizer.
26. The subterranean treatment fluid of claim 23, 24 or 25 wherein the aqueous fluid comprises a fluid selected from the group consisting of: fresh water, salt water, brine, seawater, and any combinations thereof.
27. The subterranean treatment fluid of any one of claims 23 to 26 wherein the water-soluble degradable synthetic vinyl polymer having a labile link in its backbone is present in an amount in the range of from about 0.01% to about 10% by weight of the aqueous treatment fluid.
28. A method comprising:
providing a treatment fluid comprising a water-soluble degradable synthetic vinyl polymer having a labile link in its backbone; and placing the treatment fluid in a subterranean formation.
providing a treatment fluid comprising a water-soluble degradable synthetic vinyl polymer having a labile link in its backbone; and placing the treatment fluid in a subterranean formation.
29. The method of claim 28 wherein placing the treatment fluid in the subterranean formation is a step in a stimulation treatment, a fracturing treatment, an acidizing treatment, a friction reducing operation, or a completion operation.
30. The method of claim 28 or 29 wherein placing the treatment fluid in a gelled fluid pill.
31. The method of claim 28, 29 or 30 wherein the water-soluble degradable synthetic vinyl polymer having a labile link in its backbone is present in the treatment fluid in an amount of about 0.1% to about10% by weight.
32. The method of claim 28, 29, 30 or 31 wherein placing the treatment fluid in the subterranean formation includes placing the fracturing fluid in a subterranean formation at a pressure sufficient to create or enhance a fracture therein.
33. The method of any one of claims 28 to 32 wherein the treatment fluid comprises an emulsion.
34. A method according to any one of claims 28 to 33 wherein the water-soluble degradable synthetic vinyl polymer is as defined in any one of claims 1 to 10.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/771,961 US9334338B2 (en) | 2010-04-30 | 2010-04-30 | Water-soluble degradable synthetic vinyl polymers and related methods |
| US12/771,973 US8772205B2 (en) | 2010-04-30 | 2010-04-30 | Water-soluble degradable synthetic vinyl polymers and related methods |
| US12/771,973 | 2010-04-30 | ||
| US12/771,961 | 2010-04-30 | ||
| PCT/GB2011/000670 WO2011135313A1 (en) | 2010-04-30 | 2011-04-28 | Water-soluble degradable synthetic vinyl polymers and related methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2797758A1 true CA2797758A1 (en) | 2011-11-03 |
| CA2797758C CA2797758C (en) | 2015-06-23 |
Family
ID=44860931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2797758A Expired - Fee Related CA2797758C (en) | 2010-04-30 | 2011-04-28 | Water-soluble degradable synthetic vinyl polymers and related methods |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2563820A1 (en) |
| AU (1) | AU2011247059B9 (en) |
| CA (1) | CA2797758C (en) |
| MX (1) | MX346398B (en) |
| WO (1) | WO2011135313A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9321873B2 (en) | 2005-07-21 | 2016-04-26 | Akzo Nobel N.V. | Hybrid copolymer compositions for personal care applications |
| NO20073834L (en) | 2006-07-21 | 2008-01-22 | Akzo Nobel Chemicals Int Bv | Sulfonated graft copolymers |
| US20080020961A1 (en) | 2006-07-21 | 2008-01-24 | Rodrigues Klin A | Low Molecular Weight Graft Copolymers |
| JP2014532791A (en) | 2011-11-04 | 2014-12-08 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | Hybrid dendritic copolymer, composition thereof and method for producing the same |
| US9676995B2 (en) | 2012-06-29 | 2017-06-13 | Baker Hughes Incorporated | Fracturing fluids and methods for treating hydrocarbon-bearing formations |
| US9688904B2 (en) | 2012-06-29 | 2017-06-27 | Baker Hughes Incorporated | Fracturing fluids and methods for treating hydrocarbon-bearing formations |
| US9670398B2 (en) | 2012-06-29 | 2017-06-06 | Baker Hughes Incorporated | Fracturing fluids and methods for treating hydrocarbon-bearing formations |
| US9695353B2 (en) | 2013-03-11 | 2017-07-04 | Baker Hughes Incorporated | Foamed fracturing fluids and methods for treating hydrocarbon bearing formations |
| CN104327278B (en) * | 2014-10-24 | 2017-02-15 | 中海油天津化工研究设计院有限公司 | Hydrophobic associated polymer oil-displacing agent containing chitosan and preparation method of hydrophobic associated polymer oil-displacing agent |
| CN104826614A (en) * | 2015-04-29 | 2015-08-12 | 江南大学 | Preparation method and applications of chitosan derivative absorbent |
| MX2019010536A (en) | 2017-03-06 | 2020-01-30 | Kemira Oyj | Polymer flooding produced water treatment. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7677315B2 (en) * | 2005-05-12 | 2010-03-16 | Halliburton Energy Services, Inc. | Degradable surfactants and methods for use |
| US20080312174A1 (en) * | 2007-06-05 | 2008-12-18 | Nitto Denko Corporation | Water soluble crosslinked polymers |
| US20090105097A1 (en) * | 2007-10-22 | 2009-04-23 | Carlos Abad | Degradable Friction Reducer |
-
2011
- 2011-04-28 WO PCT/GB2011/000670 patent/WO2011135313A1/en active Application Filing
- 2011-04-28 EP EP11720827A patent/EP2563820A1/en not_active Withdrawn
- 2011-04-28 CA CA2797758A patent/CA2797758C/en not_active Expired - Fee Related
- 2011-04-28 AU AU2011247059A patent/AU2011247059B9/en not_active Ceased
- 2011-04-28 MX MX2012012575A patent/MX346398B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AU2011247059B2 (en) | 2013-12-12 |
| EP2563820A1 (en) | 2013-03-06 |
| WO2011135313A1 (en) | 2011-11-03 |
| AU2011247059B9 (en) | 2014-01-09 |
| MX346398B (en) | 2017-03-16 |
| MX2012012575A (en) | 2012-12-17 |
| AU2011247059A1 (en) | 2012-10-11 |
| CA2797758C (en) | 2015-06-23 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| EEER | Examination request |
Effective date: 20121029 |
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| MKLA | Lapsed |
Effective date: 20220301 |
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| MKLA | Lapsed |
Effective date: 20200831 |