CA2797758A1 - Water-soluble degradable synthetic vinyl polymers and related methods - Google Patents
Water-soluble degradable synthetic vinyl polymers and related methods Download PDFInfo
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- 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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- Prior art keywords
- water
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- vinyl polymer
- degradable synthetic
- soluble degradable
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- 229920002554 vinyl polymer Polymers 0.000 title claims abstract 36
- 238000000034 method Methods 0.000 title claims 13
- 239000012530 fluid Substances 0.000 claims abstract 20
- 239000000178 monomer Substances 0.000 claims abstract 6
- 229910021645 metal ion Inorganic materials 0.000 claims abstract 5
- 238000007717 redox polymerization reaction Methods 0.000 claims abstract 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract 5
- 230000001590 oxidative effect Effects 0.000 claims abstract 4
- 239000000376 reactant Substances 0.000 claims abstract 2
- -1 poly(anhydride) Polymers 0.000 claims 29
- 239000000839 emulsion Substances 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 239000003431 cross linking reagent Substances 0.000 claims 3
- 239000000693 micelle Substances 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 238000006731 degradation reaction Methods 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims 1
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 229920002101 Chitin Polymers 0.000 claims 1
- 229920001661 Chitosan Polymers 0.000 claims 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 229930182556 Polyacetal Natural products 0.000 claims 1
- 229920000954 Polyglycolide Polymers 0.000 claims 1
- 229920001710 Polyorthoester Polymers 0.000 claims 1
- 125000004036 acetal group Chemical group 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical group 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- 125000005587 carbonate group Chemical group 0.000 claims 1
- ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical compound [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000002228 disulfide group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- ZAFFWOKULJCCSA-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;trimethylazanium;chloride Chemical compound [Cl-].C[NH+](C)C.CCOC(=O)C(C)=C ZAFFWOKULJCCSA-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000013505 freshwater Substances 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- BGQJNGISTPIALH-UHFFFAOYSA-N n,n-bis(prop-2-enyl)acetamide Chemical compound C=CCN(C(=O)C)CC=C BGQJNGISTPIALH-UHFFFAOYSA-N 0.000 claims 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 1
- IFVGFQAONSKBCR-UHFFFAOYSA-N n-[bis(aziridin-1-yl)phosphoryl]pyrimidin-2-amine Chemical group C1CN1P(N1CC1)(=O)NC1=NC=CC=N1 IFVGFQAONSKBCR-UHFFFAOYSA-N 0.000 claims 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims 1
- 125000002092 orthoester group Chemical group 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 238000001782 photodegradation Methods 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 1
- 229920001308 poly(aminoacid) Polymers 0.000 claims 1
- 229920000747 poly(lactic acid) Polymers 0.000 claims 1
- 239000002745 poly(ortho ester) Substances 0.000 claims 1
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229920001610 polycaprolactone Polymers 0.000 claims 1
- 229920002721 polycyanoacrylate Polymers 0.000 claims 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 229920006324 polyoxymethylene Polymers 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 229920002689 polyvinyl acetate Polymers 0.000 claims 1
- 239000011118 polyvinyl acetate Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002455 scale inhibitor Substances 0.000 claims 1
- 239000013535 sea water Substances 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
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- 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
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- 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
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- 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
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- 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
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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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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 |
|---|---|---|---|
| US12/771,973 | 2010-04-30 | ||
| US12/771,961 | 2010-04-30 | ||
| 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 |
| 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 |
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| AU (1) | AU2011247059B9 (en) |
| CA (1) | CA2797758C (en) |
| MX (1) | MX346398B (en) |
| WO (1) | WO2011135313A1 (en) |
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| NO20073821L (en) | 2006-07-21 | 2008-01-22 | Akzo Nobel Chemicals Int Bv | Inoculated low molecular weight copolymers |
| NO20073834L (en) | 2006-07-21 | 2008-01-22 | Akzo Nobel Chemicals Int Bv | Sulfonated graft copolymers |
| CN102549034B (en) | 2009-07-31 | 2014-12-10 | 阿克佐诺贝尔股份有限公司 | Hybrid copolymer compositions for personal care applications |
| IN2014DN03123A (en) | 2011-11-04 | 2015-05-22 | Akzo Nobel Chemicals Int Bv | |
| 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. |
| CN117402349B (en) * | 2022-07-15 | 2025-09-02 | 中石化石油工程技术服务有限公司 | A nano-plugging fluid loss reducer and its preparation method and application |
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| 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 |
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- 2011-04-28 EP EP11720827A patent/EP2563820A1/en not_active Withdrawn
- 2011-04-28 AU AU2011247059A patent/AU2011247059B9/en not_active Ceased
- 2011-04-28 WO PCT/GB2011/000670 patent/WO2011135313A1/en not_active Ceased
- 2011-04-28 MX MX2012012575A patent/MX346398B/en active IP Right Grant
- 2011-04-28 CA CA2797758A patent/CA2797758C/en not_active Expired - Fee Related
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| EP2563820A1 (en) | 2013-03-06 |
| WO2011135313A1 (en) | 2011-11-03 |
| AU2011247059A1 (en) | 2012-10-11 |
| AU2011247059B2 (en) | 2013-12-12 |
| CA2797758C (en) | 2015-06-23 |
| MX346398B (en) | 2017-03-16 |
| MX2012012575A (en) | 2012-12-17 |
| AU2011247059B9 (en) | 2014-01-09 |
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