WO2011018604A1 - Hydrophobically and cationically modified relative permeability modifiers and associated methods - Google Patents
Hydrophobically and cationically modified relative permeability modifiers and associated methods Download PDFInfo
- Publication number
- WO2011018604A1 WO2011018604A1 PCT/GB2010/001448 GB2010001448W WO2011018604A1 WO 2011018604 A1 WO2011018604 A1 WO 2011018604A1 GB 2010001448 W GB2010001448 W GB 2010001448W WO 2011018604 A1 WO2011018604 A1 WO 2011018604A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrophobically
- relative permeability
- alkyl
- cationically modified
- hydrophilic polymer
- Prior art date
Links
Classifications
-
- 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
- C09K8/50—Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls
- C09K8/504—Compositions based on water or polar solvents
- C09K8/506—Compositions based on water or polar solvents containing organic compounds
- C09K8/508—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
Definitions
- the present invention relates to subterranean treatments and, more particularly, in one or more embodiments, to introducing a hydrophobically and cationically modified relative permeability modifier into a subterranean interval to reduce the effective permeability of the subterranean interval to aqueous-based fluids.
- Hydrophobically modified polymers have recently been used as relative permeability modifiers. Hydrophobically modified polymers may also be used in operations to assist in leak off control, clay stabilization, fines control, cement fluid loss control, and the diversion of treatment fluids. However, under certain pH and temperature conditions (e.g., at temperatures above 140°F (60 0 C) and at pH's above 7) these polymers may precipitate out of solution limiting their effectiveness as relative permeability modifiers.
- the present invention relates to subterranean treatments and, more particularly, in one or more embodiments, to introducing a hydrophobically and cationically modified relative permeability modifier into a subterranean interval to reduce the effective permeability of the subterranean interval to aqueous-based fluids.
- the present invention includes a method of introducing a hydrophobically and cationically modified relative permeability modifier into a portion of a subterranean formation, wherein the hydrophobically and cationically modified relative permeability modifier comprises a hydrophilic polymer backbone with a hydrophobic modification and a cationic modification.
- the present invention provides a method of improving the stability of a relative permeability modifier comprising: providing a relative permeability modifier that comprises a hydrophilic polymer backbone with a hydrophobic modification; and incorporating at least one cationic compound onto the hydrophilic polymer backbone to form a hydrophobically and cationically modified relative permeability modifier.
- the present invention includes a treatment fluid comprising a hydrophobically and cationically modified relative permeability modifier that comprises a hydrophilic polymer backbone with a hydrophobic modification and a cationic modification.
- the present invention relates to subterranean treatments and, more particularly, in one or more embodiments, to introducing a hydrophobically and cationically modified relative permeability modifier into a subterranean interval to reduce the effective permeability of the subterranean interval to aqueous-based fluids.
- Embodiments of the present invention relate to using a hydrophobically and cationically modified relative permeability modifier to treat a subterranean formation, or an interval or portion thereof.
- relative permeability modifier refers to a water-soluble polymer comprising a hydrophilic polymer backbone that selectively reduces the effective permeability of at least a portion of a subterranean formation to aqueous-based fluids.
- hydrophobically modified “hydrophobic modification,” and the like refer to the incorporation into the hydrophilic polymer backbone of at least one hydrophobic group, wherein the alkyl chain length is about 4 to about 22 carbons.
- the terms “cationically modified,” “cationic modification,” and the like refer to the incorporation of at least one cationic group or a cationic forming group that comprises a short chain alkyl group, wherein the alkyl chain length is about 1 to about 3 carbons.
- the term “hydrophobically and cationically modified relative permeability modifier” refers to a relative permeability modifier that has both a hydrophobic modification and a cationic modification.
- the hydrophobically and cationically modified relative permeability modifier may form a hydrated or hydratable film or a mono- or multi-layered adsorbed hydrated or hydratable polymer layer on a well bore surface and/or around an oil droplet in a pore space, including pore throats in the interval of the subterranean formation, thereby decreasing water permeability.
- the hydrophobically and cationically modified relative permeability modifier may also be used to divert treatment fluids, for example, to less permeable portions of the formation.
- the hydrophobically and cationically modified relative permeability modifier may also be used in cementing operations, fracturing operations, and drilling operations and also may be used as a spacer fluid.
- suitable hydrophobically and cationically modified relative permeability modifiers may be any of a variety of water soluble polymers that are both hydrophobically modified and cationically modified and are capable of selectively reducing the effective permeability of a formation to aqueous-based fluids without a comparable reduction of the formation's effective permeability to hydrocarbons. While the hydrophobically and cationically modified relative permeability modifiers suitable for use in the present invention may have hydrophobic groups incorporated into the hydrophilic polymer structure, they should remain water soluble.
- water soluble refers to at least about 0.0001 weight percent soluble in water. In certain embodiments, the water-soluble polymer is at least about 0.45 weight percent soluble in distilled water at room temperature. In certain embodiments, the water-soluble polymer is at least about 0.6 weight percent soluble in distilled water at room temperature.
- the hydrophobically and cationically modified relative permeability modifiers of the present invention have a cationic charge as a result of a cationic modification.
- the cationic charge in the polymer is independent of the pH of the fluid comprising the relative permeability modifier.
- the cationic modification comprises a quaternized nitrogen, and not a protonated amine as would be the case if an amine is contacted with a Bronsted acid or a Lewis acid reacted amine. Therefore, the cationic charge is not because acidification or protonation of an amine.
- Examples of hydrophobically and cationically modified relative permeability modifiers may comprise a hydrophilic polymer backbone, at least one hydrophobic modification, and at least one cationic modification.
- the hydrophobic modification comprises a hydrophobic branch comprising an alkyl chain of about 4 to about 22 carbons and the cationic modification comprises a cationic group or cationic forming group comprising an alkyl chain of about 1 to about 3 carbons.
- the hydrophobic branch may have an alkyl chain length of about 7 to about 22 carbons.
- the hydrophobic branch may have an alkyl chain length of about 12 to about 18 carbons.
- the cationic group or cationic forming group may have an alkyl chain length of about 1 , 2, or 3 carbons.
- the hydrophobically and cationically modified relative permeability modifiers may comprise a polymer backbone that comprises polar heteroatoms.
- the polar heteroatoms present within the polymer backbone of the hydrophobically and cationically modified relative permeability modifiers include, but are not limited to, oxygen, nitrogen, sulfur, or phosphorous.
- Hydrophobically and cationically modified relative permeability modifiers suitable for use in the present invention may be synthesized utilizing any suitable technique.
- suitable hydrophobically and cationically modified relative permeability modifiers may be synthesized by the hydrophobic modification and the cationic modification of a hydrophilic polymer via a reaction with a hydrophobic compound and a cationic compound.
- the term "cationic compound" includes not only cationic compounds, but cationic forming compounds.
- suitable hydrophobically and cationically modified relative permeability modifiers may be a reaction product of a reaction comprising a hydrophilic polymer, a hydrophobic compound, and a cationic compound.
- the hydrophobically and cationically modified relative permeability modifiers may be prepared by reacting a reaction product formed from a reaction of a hydrophilic polymer with a hydrophobic compound, with a cationic compound.
- the hydrophobically and cationically modified relative permeability modifiers may be prepared by reacting a reaction product formed from a reaction of a hydrophilic polymer with a cationic compound, with a hydrophobic compound.
- the hydrophobically and cationically modified relative permeability modifiers may be prepared from a polymerization reaction comprising a hydrophilic monomer, a hydrophobically modified hydrophilic monomer, and a cationic monomer.
- the hydrophobically and cationically modified relative permeability modifiers may be pre-reacted before they are placed into the well bore.
- the hydrophobically and cationically modified relative permeability modifiers may be prepared by an appropriate in situ reaction. Hydrophobically modified polymers and methods for their preparation are described in more detail in U.S. Pat. Nos. 6,476,169 and 7,117,942, the disclosures of which are incorporated herein by reference. Those of ordinary skill in the art, with the benefit of this disclosure, will be able to determine other suitable methods for the synthesis of suitable hydrophobically and cationically modified relative permeability modifiers.
- hydrophobically and cationically modified relative permeability modifiers suitable for use in the present invention may be synthesized by the reaction of a hydrophilic polymer with a hydrophobic compound and a cationic compound.
- Hydrophilic polymers suitable for forming the hydrophobically and cationically modified relative permeability modifiers of the present invention should be capable of reacting with hydrophobic compounds and cationic compounds.
- hydrophilic polymers include, homo-, co-, or terpolymers such as, but not limited to, polyacrylamides, polyvinylamines, poly(vinylamines/vinyl alcohols), alkyl acrylate polymers, alkylamino acrylate or alkylamino alkylacrylate polymers in general, and combinations thereof.
- alkyl acrylate polymers, polyacrylamides, and alkylamino acrylate polymers and alkylaminoalkyl acrylate polymers include polydimethylaminoethyl methacrylate, polydimethylaminopropyl methacrylamide, poly(acrylamide/dimethylaminoethyl methacrylate), poly(methacrylic acid/dimethylaminoethyl methacrylate), poly(2-acrylamido-2-methyl propane sulfonic acid/dimethylaminoethyl methacrylate), poly(acrylamide/dimethylaminopropyl methacrylamide), poly (acrylic acid/dimethylaminopropyl methacrylamide), poly(methacrylic acid/dimethylaminopropyl methacrylamide), and combinations thereof.
- a hydrophilic polymer suitable for use in the present invention may comprise a polymer backbone that contains a reactive amino group in the polymer backbone or as a pendant group, wherein the reactive amino group is capable of reacting with a hydrophobic compound and/or a cationic compound.
- a suitable hydrophilic polymer may comprise a dialkyl amino pendant group.
- a suitable hydrophilic polymer may comprise a dimethyl amino pendant group and a monomer comprising dimethylaminoethyl methacrylate or dimethylaminopropyl methacrylamide.
- a suitable hydrophilic polymer may be formed from monomers containing amine groups in about 20-100 mole % of the monomers.
- a suitable hydrophilic polymer may comprise a polymer backbone comprising polar heteroatoms, wherein the polar heteroatoms present within the polymer backbone of the hydrophilic polymer includes oxygen, nitrogen, sulfur, or phosphorous.
- Suitable hydrophilic polymers that comprise polar heteroatoms within the polymer backbone include homo-, co-, or terpolymers, such as, but not limited to, celluloses, chitosans, polyamides, polyetheramines, polyethyleneimines, polyhydroxyetheramines, polylysines, polysulfones, gums, starches, and combinations thereof.
- the starch is a cationic starch.
- a suitable cationic starch may be formed by reacting a starch, such as corn, maize, waxy maize, potato, tapioca, or the like, with the reaction product of epichlorohydrin and trialkylamine.
- Suitable hydrophobic compounds that are capable of reacting with the hydrophilic polymers include alcohols, amines, epoxides, alkyl halides, sulfonates, sulfates, organic acids, and organic acid derivatives that comprise an alkyl chain length of from about 4 to about 22 carbons.
- suitable organic acids and derivatives thereof include, but are not limited to, acid anhydrides, esters, imides, acid halides and amides of carboxylic acids that comprise an alkyl chain length of from about 4 to about 22 carbons.
- the hydrophobic compounds may have an alkyl chain length of from about 7 to about 22 carbons.
- the hydrophobic compounds may have an alkyl chain length of from about 12 to about 18 carbons.
- the reaction between the hydrophobic compound and hydrophilic polymer may result in the quaternization of at least some of the hydrophilic polymer amino groups with an alkyl halide, wherein the alkyl chain length is from about 4 to about 22 carbons.
- Suitable cationic compounds that are capable of reacting with the hydrophilic polymers include alcohols, amines, epoxides, alkyl halides, sulfonates, sulfates, organic acids, and organic acid derivatives that comprise an alkyl chain length of from about 1 to about 3 carbons.
- suitable organic acids and derivatives thereof include, but are not limited to, acid anhydrides, esters, imides, acid halides and amides of carboxylic acids that comprise an alkyl chain length of from about 1 to about 3 carbons.
- the cationic compounds may have an alkyl chain length of 1, 2, or 3 carbons.
- the reaction between the cationic compound and hydrophilic polymer may result in the quaternization of at least some of the hydrophilic polymer amino groups with an alkyl halide, wherein the alkyl chain length is from about 1 to about 3 carbons.
- suitable cationic compounds include aminoethyltrimethylammonium halides, 2-chloro- or 2- bromoethyltrimethylammonium halide, 3-chloro- or 3-bromopropyl trimethylammonium halide and a reaction product of trialkylamine, for example trimethylamine, with epichlorohydrin.
- a cationic modification and/or a hydrophobic modification may be incorporated into the hydrophilic polymer backbone by quaternizing amine groups located in the hydrophilic polymer backbone.
- hydrophobic compounds may be present in the hydrophilic polymer structure in an amount sufficient to quaternize up to and including about 10% of the amine groups.
- hydrophobic compounds may be present in the hydrophilic polymer structure in an amount sufficient to quaternize about 1% to about 5% of the amine groups.
- cationic compounds may be present in the hydrophilic polymer structure in an amount sufficient to quaternize up to and including about 50% of the amine groups.
- the cationic compounds may be present in the hydrophilic polymer structure in an amount sufficient to quaternize about 1% to about 20% of the amine groups. In other embodiments, the cationic compounds may be present in the hydrophilic polymer structure in an amount sufficient to quaternize about 5% to about 10% of the amine groups.
- Suitable hydrophobically and cationically modified relative permeability modifiers include a polymer that has been hydrophobically modified with an alkyl group present on an amino group (in the polymer backbone or as a pendant group) in quaternized form and has been cationically modified with an alkyl group present on an amino group (in the polymer backbone or as a pendant group) in quaternized form.
- an alkyl group may be present on a dialkyl amino pendant group in quaternized form.
- the dialkyl amino pendant group comprises a dimethyl amino pendant group.
- hydrophobically and cationically modified relative permeability modifier includes a poly(dimethylaminoethylmethacrylate) or poly(dimethylaminopropylmethacrylamide) that has been hydrophobically modified with an alkyl group with 4 carbons to 22 carbons (e.g., 4 carbons, 6, carbons, 8 carbons, 10 carbons, 12 carbons, 14 carbons, 16 carbons, 18 carbons, 20 carbons, 22 carbons, etc.) on a dimethylamino group and has been cationically modified with an alkyl group with 1 to 3 carbons on another dimethylamino group.
- an alkyl group with 4 carbons to 22 carbons e.g., 4 carbons, 6, carbons, 8 carbons, 10 carbons, 12 carbons, 14 carbons, 16 carbons, 18 carbons, 20 carbons, 22 carbons, etc.
- suitable hydrophobically and cationically modified relative permeability modifiers also may be prepared from a polymerization reaction comprising a hydrophilic monomer, a hydrophobically modified hydrophilic monomer, and a cationic monomer.
- suitable hydrophobically and cationically modified relative permeability modifiers may be prepared by first polymerizing a hydrophilic polymer and a hydrophobically modified hydrophilic monomer, and then reacting the resulting polymer with a cationic compound or a cationic monomer.
- suitable hydrophobically and cationically modified relative permeability modifiers may also be prepared by first polymerizing a hydrophilic monomer and cationic monomer, and then reacting the resulting polymer with a hydrophobic compound or hydrophobic monomer.
- Suitable hydrophobically and cationically modified relative permeability modifiers synthesized from the polymerization reactions may have estimated molecular weights in the range of from about 100,000 to about 10,000,000.
- the mole ratios of the hydrophilic monomer(s) to the hydrophobically modified hydrophilic monomer(s) and the cationically modified hydrophilic monomer(s) may be in the range of from about 99.98 to 90:10.
- hydrophilic monomers may be used to form the hydrophobically and cationically modified relative permeability modifiers useful in the present invention.
- suitable hydrophilic monomers include, but are not limited to, acrylamide, 2-acrylamido-2-methyl propane sulfonic acid, N,N-dimethylacrylamide, vinyl pyrrolidone, dimethylaminoethyl methacrylate, acrylic acid, dimethylaminopropylmethacrylamide, vinyl amine, vinyl acetate, methacrylamide, hydroxyethyl acrylate, vinyl sulfonic acid, vinyl phosphonic acid, methacrylic acid, vinyl caprolactam, N-vinylformamide, N,N-diallylacetamide, itaconic acid, and styrene sulfonic acid, and combinations thereof.
- hydrophobically modified hydrophilic monomers also may be used to form the hydrophobically and cationically modified relative permeability modifiers useful in the present invention.
- suitable hydrophobically modified hydrophilic monomers include, but are not limited to, alkyl acrylates, alkyl methacrylates, alkyl acrylamides, alkyl methacrylamides, wherein the alkyl groups have from about 4 to about 22 carbon atoms. In another embodiment, the alkyl groups have from about 7 to about 22 carbons. In another embodiment, the alkyl groups have from about 12 to about 18 carbons.
- the hydrophobically modified hydrophilic monomer comprises 2-ethylhexyl methacrylate, or hexadecyl methacrylamide.
- the hydrophobically modified hydrophilic monomers may be cationic. Examples of cationic hydrophobically modified hydrophilic monomers include, alkyl dimethylammoniumethyl methacrylate halides, and alkyl dimethylammoniumpropyl methacrylamide halides.
- Such monomers include, octadecyldimethylammoniumethyl methacrylate bromide, hexadecyldimethylammoniurnethyl methacrylate bromide, and hexadecyldimethylammoniumpropyl methacrylamide bromide.
- a variety of cationic monomers also may be used to form the hydrophobically and cationically modified relative permeability modifiers useful in the present invention.
- suitable cationic monomers include, but are not limited to, dimethyldiallyl ammonium halide, trimethylammoniumethyl methacrylate halide, trimethylammoniumpropyl methacrylamide halide, methacrylamidoethyltrimethyl ammonium halide, quaternary salt derivatives of acrylamide and quaternary salt derivatives of acrylic acid and combinations thereof.
- the mole ratio of cationic modifications to hydrophobic modifications present in the hydrophobically and cationically modified relative permeability modifiers may be in the range of from about 1:1 to about 50:1. In other embodiments, the mole ratio of cationic modifications to hydrophobic modifications present in the hydrophobically and cationically modified relative permeability modifiers may be in the range of from about 2:1 to about 20:1. In other embodiments, the mole ratio of cationic modifications to hydrophobic modifications present in the hydrophobically and cationically modified relative permeability modifiers may be in the range of from about 5:1 to about 10:1.
- hydrophobically and cationically modified relative permeability modifiers examples include, but are not limited to:
- hydrophobically and cationically modified relative permeability modifiers may be present in a permeability modifying fluid introduced into a subterranean formation.
- Treatment fluids comprising hydrophobically and cationically modified relative permeability modifiers will be referred to herein as "permeability modifying fluids.”
- permeability modifying fluids Sufficient concentrations of hydrophobically and cationically modified relative permeability modifiers should be present in these permeability modifying fluids to provide the desired level of permeability modification.
- hydrophobically and cationically modified relative permeability modifiers may be present in these permeability modifying fluids in an amount in the range of from about 0.02% to about 10% by weight of the permeability modifying fluid.
- hydrophobically and cationically modified relative permeability modifiers may be present in these permeability modifying fluids in an amount in the range of from about 0.05% to about 1.0% by weight of the permeability modifying fluid.
- hydrophobically and cationically modified relative permeability modifiers may be provided in a concentrated aqueous solution prior to its combination with the other components necessary to form the permeability modifying fluids.
- the permeability modifying fluids generally also comprise water.
- the water included in the permeability modifying fluid may include freshwater, saltwater (e.g., water containing one or more salts dissolved therein), brines (e.g., natural or produced brines), seawater, or another other aqueous fluid that does not undesirably effect the other components in the permeability modifying fluid.
- compositions disclosed herein may be used to treat an interval of a subterranean formation penetrated by a well bore.
- the interval may represent an interval that has been identified for treatment with a hydrophobically and cationically modified relative permeability modifier to reduce the effective permeability of the interval to aqueous-based fluids, in accordance with present embodiments.
- the interval may be any interval of a subterranean formation suitable for treatment.
- embodiments of the present invention may be applicable for the treatment of both production and injection wells. Additionally, embodiments of the present invention also may be suitable for cased well bores or openhole well bores.
- the interval may be contacted with a hydrophobically and cationically modified relative permeability modifier.
- the hydrophobically and cationically modified relative permeability modifier may be present in a permeability modifying fluid introduced into the interval.
- the near well bore portion of the interval is contacted with the hydrophobically and cationically modified relative permeability modifier.
- the "near well bore portion" of a formation generally refers to the portion of a subterranean formation surrounding a well bore.
- the "near well bore portion" may refer to the portion of the formation surrounding a well bore and having a depth of penetration of from about 7 (2.1 m) to about 10 feet (3 m).
- any suitable technique may be used for introduction of the permeability modifying fluid into the interval, for example, bull heading, coil tubing, jointed pipe (e.g., with straddle packers, pinpoint injection tools, etc.) or any other suitable technique may be used.
- the permeability modifying fluid may be introduced into the interval at matrix flow rates.
- Example flow rates for the permeability modifying fluid are in the range of from about 0.25 barrels to about 3 barrels per minute. However, those of ordinary skill in the art will appreciate that these flow rates are merely examples, and embodiments of the present invention are applicable to flow rates outside these ranges.
- the permeability modifying fluids of the present invention may be used in a variety of well operations, including fracturing operations, cementing operations, drilling operations, and may also be used as spacer fluids.
- the permeability modifying fluids of the present invention may be used in a fracturing operation.
- the present invention provides a method of fracturing a subterranean formation penetrated by a well bore, the method comprising introducing a fracturing fluid comprising a permeability modifying fluid into the well bore at or above a pressure sufficient to create or enhance at least one fracture in the subterranean formation.
- Introducing the fracturing fluid into the well bore may be accomplished by using any fracturing equipment known in the art.
- the permeability modifying fluids of the present invention may be used in a drilling operation.
- the present invention provides a method of drilling a portion of a well bore comprising the steps of providing a drilling fluid that comprises a permeability modifying fluid and drilling the well bore. Drilling the well bore may be accomplished by using drilling equipment, such as a drill string and a drill bit, along with the drilling fluid. Drilling operations may include any suitable technique for forming a well bore that penetrates a subterranean formation. Examples of suitable techniques for forming a well bore may include, but are not limited to, rotary drilling and cable-tool drilling. Other techniques for forming a well bore may be used, but generally to a lesser extent.
- Rotary drilling operations typically involve attaching a drill bit on a lower end of a drill string to form a drilling tool and rotating the drill bit along with the drill string into a subterranean formation to create a well bore through which subsurface formation fluids may be produced. As the drill bit penetrates the subterranean formation, additional joints of pipe may be coupled to the drill string. In another method of drilling, coiled tubing may be used instead of jointed pipe and the drill bit may be rotated using a downhole motor.
- the permeability modifying fluids of the present invention may be used in a cementing operation.
- the cementing operation may be a primary cementing operation.
- the present invention provides a method comprising providing a cement composition that comprises a hydrophobically and cationically modified relative permeability modifier, introducing the cement composition to a subterranean well bore; and allowing the cement composition to set therein.
- the cement composition may be pumped into the annular space between the walls of a well bore and the exterior surface of the pipe string disposed therein.
- the cement composition may be permitted to set in the annular space, thereby forming an annular sheath of hardened substantially impermeable cement therein that substantially supports and positions the pipe string in the well bore and bonds the exterior surfaces of the pipe string to the walls of the well bore.
- the cement composition may be used in remedial cementing operations such as plugging highly permeable zones or fractures in well bores, plugging cracks in holes in pipe strings, and the like.
- spacer fluid compositions comprising a permeability modifying fluid of the present invention are provided.
- the spacer fluid may be utilized as a buffer between two fluids during subterranean operations.
- a spacer fluid may be pumped into a well bore between a first fluid and a second fluid.
- the first fluid should be displaced with the spacer fluid
- the spacer fluid should be displaced with the second fluid.
- the spacer fluids should be compatible with the fluid that it is displacing and the second fluid that is displacing the spacer fluid, in that there should be no undesirable interactions between the spacer fluid and the first or the second fluid.
- the first fluid may be any fluid that the spacer fluid should displace, such as drilling fluids.
- the second fluid may be any fluid desired to be introduced into the well bore, such as cement compositions, drilling fluids, completion brines, and the like.
- the second fluid may be a drilling fluid. It is believed that during normal leak off from the spacer fluids of the present invention into the subterranean formation, the hydrophobically and cationically modified relative permeability modifier, among other things, may attach to surfaces within the subterranean formation.
- the presence of the hydrophobically and cationically modified relative permeability modifiers in the subterranean formation may reduce the permeability of the treated sections of the subterranean formation to aqueous-based fluids (e.g., water) with little or no reduction in the permeability of the subterranean formation with respect to hydrocarbons. This may reduce the subsequent problems associated with water flowing into the well bore from the subterranean formation.
- aqueous-based fluids e.g., water
- a hydrophobically and cationically modified relative permeability modifier was prepared.
- the first fluid comprised a 2000 ppm solution of polydimethylaminoethyl methacrylate ("polyDMAEMA”) reacted with 5 mole % hexadecyl bromide (“C 16Br").
- polyDMAEMA polydimethylaminoethyl methacrylate
- C 16Br polydimethylaminoethyl methacrylate
- a second fluid comprising a hydrophobically and cationically modified relative permeability modifier was prepared.
- the second fluid comprised a 2000 ppm solution of polyDMAEMA reacted with 5 mole % C 16Br and 5 mole % propyl iodide ("C3I"). Both of these fluids were then heated to approximately 150°F (66°) at pH of 8.6. It was observed that the polyDMAEMA + C16Br present in the first fluid precipitated out of solution, while the polyDMAEMA + C 16Br + C3I present in the second fluid remained in solution.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2010283625A AU2010283625B2 (en) | 2009-08-10 | 2010-07-29 | Hydrophobically and cationically modified relative permeability modifiers and associated methods |
EP10739671.5A EP2464708B1 (en) | 2009-08-10 | 2010-07-29 | Hydrophobically and cationically modified relative permeability modifiers and associated methods |
MX2012001536A MX2012001536A (en) | 2009-08-10 | 2010-07-29 | Hydrophobically and cationically modified relative permeability modifiers and associated methods. |
CA2768594A CA2768594C (en) | 2009-08-10 | 2010-07-29 | Hydrophobically and cationically modified relative permeability modifiers and associated methods |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/538,203 | 2009-08-10 | ||
US12/538,203 US8420576B2 (en) | 2009-08-10 | 2009-08-10 | Hydrophobically and cationically modified relative permeability modifiers and associated methods |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011018604A1 true WO2011018604A1 (en) | 2011-02-17 |
Family
ID=42751824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2010/001448 WO2011018604A1 (en) | 2009-08-10 | 2010-07-29 | Hydrophobically and cationically modified relative permeability modifiers and associated methods |
Country Status (7)
Country | Link |
---|---|
US (2) | US8420576B2 (en) |
EP (1) | EP2464708B1 (en) |
AR (1) | AR077607A1 (en) |
AU (1) | AU2010283625B2 (en) |
CA (1) | CA2768594C (en) |
MX (1) | MX2012001536A (en) |
WO (1) | WO2011018604A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015042489A1 (en) * | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Method of using surface modifying metallic treatment agents to treat subterranean formations |
US9562188B2 (en) | 2013-09-20 | 2017-02-07 | Baker Hughes Incorporated | Composites for use in stimulation and sand control operations |
US9701892B2 (en) | 2014-04-17 | 2017-07-11 | Baker Hughes Incorporated | Method of pumping aqueous fluid containing surface modifying treatment agent into a well |
US9822621B2 (en) | 2013-09-20 | 2017-11-21 | Baker Hughes, A Ge Company, Llc | Method of using surface modifying treatment agents to treat subterranean formations |
US10047280B2 (en) | 2013-09-20 | 2018-08-14 | Baker Hughes, A Ge Company, Llc | Organophosphorus containing composites for use in well treatment operations |
US10227846B2 (en) | 2013-09-20 | 2019-03-12 | Baker Hughes, A Ge Company, Llc | Method of inhibiting fouling on a metallic surface using a surface modifying treatment agent |
US10472555B2 (en) | 2016-04-08 | 2019-11-12 | Schlumberger Technology Corporation | Polymer gel for water control applications |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9018140B2 (en) * | 2012-05-18 | 2015-04-28 | Halliburton Energy Services, Inc. | Methods for stabilizing water-sensitive clays |
US9169430B2 (en) | 2012-10-30 | 2015-10-27 | Ecolab Usa Inc. | Chemical treatment method and additive used to treat fines migration and flow through porous media |
US20150315456A1 (en) * | 2012-12-03 | 2015-11-05 | Schlumberger Technology Corporation | Methods for treating a subterranean well |
CN104109241B (en) * | 2013-04-17 | 2019-01-11 | 复旦大学附属肿瘤医院 | The polyethyleneimine and its preparation method and application of covalent hydrophobic modification |
US9441151B2 (en) | 2013-05-14 | 2016-09-13 | Halliburton Energy Serives, Inc. | Wellbore servicing materials and methods of making and using same |
US9475976B2 (en) | 2013-05-20 | 2016-10-25 | Halliburton Energy Services, Inc. | Methods and compositions of improving wellbore cleanout treatments |
WO2015030721A1 (en) | 2013-08-27 | 2015-03-05 | Halliburton Energy Services, Inc. | Acid diversion treatments in injection wells using permeability modifiers |
CA2926195C (en) | 2013-10-30 | 2018-06-05 | Halliburton Energy Services, Inc. | Vulcanized oil and water swellable particulate composite compositions |
US9670397B2 (en) | 2014-02-21 | 2017-06-06 | Halliburton Energy Services Inc. | Amido-functionalized gemini surfactant for fluid control in subterranean formations |
US10160899B2 (en) | 2014-05-15 | 2018-12-25 | Halliburton Energy Services, Inc. | Method of treating water-swellable minerals in a subterranean formation with a stabilizing compound with a cationic group and hydrophobic portion |
BR112016025881B1 (en) * | 2014-06-27 | 2022-03-03 | Halliburton Energy Services, Inc | Method to decrease water permeability within an underground formation |
WO2016126233A1 (en) | 2015-02-02 | 2016-08-11 | Halliburton Energy Services, Inc. | Deactivation and activation of permeability modifiers for use in subterranean formation operations |
US10563491B2 (en) * | 2015-02-25 | 2020-02-18 | Halliburton Energy Services, Inc. | Mitigating water inclusion in downhole pumps |
US10815766B2 (en) | 2015-02-27 | 2020-10-27 | Schlumberger Technology Corporation | Vertical drilling and fracturing methodology |
MX2017009871A (en) | 2015-03-05 | 2017-11-15 | Halliburton Energy Services Inc | Sulfonated relative permeability modifiers for reducing subterranean formation water permeability. |
US9869170B2 (en) | 2015-03-17 | 2018-01-16 | Halliburton Energy Services, Inc. | Methods of controlling water production in horizontal wells with multistage fractures |
EP3510245A4 (en) | 2016-09-12 | 2020-05-13 | Services Pétroliers Schlumberger | Attaining access to compromised fractured production regions at an oilfield |
CN108117621B (en) * | 2016-11-30 | 2020-12-11 | 中国石油化工股份有限公司 | Tackifying calcium salt resistant polymer filtrate reducer and preparation method thereof |
EP3565950A4 (en) | 2017-01-04 | 2020-08-26 | Services Pétroliers Schlumberger | Reservoir stimulation comprising hydraulic fracturing through extended tunnels |
US10544080B2 (en) | 2017-06-14 | 2020-01-28 | Chevron Phillips Chemical Company Lp | Continuous process for the conversion of olefins and carbon dioxide to acrylates via solution phase reactor |
US11486214B2 (en) | 2017-07-10 | 2022-11-01 | Schlumberger Technology Corporation | Controlled release of hose |
US11203901B2 (en) | 2017-07-10 | 2021-12-21 | Schlumberger Technology Corporation | Radial drilling link transmission and flex shaft protective cover |
EP3735450A1 (en) * | 2018-01-02 | 2020-11-11 | Saudi Arabian Oil Company | Composition of encapsulated chemical additives and methods for preparation of the same |
EP3533854B1 (en) | 2018-03-01 | 2022-05-04 | Momentive Performance Materials Inc. | Method of inhibiting water penetration into oil- and gas- producing formations |
US11193332B2 (en) | 2018-09-13 | 2021-12-07 | Schlumberger Technology Corporation | Slider compensated flexible shaft drilling system |
CN110964148A (en) * | 2019-12-18 | 2020-04-07 | 陕西科技大学 | Fluorine-containing hydrophobic associated cationic polyacrylamide flocculant and preparation method thereof |
US11408240B2 (en) | 2020-02-04 | 2022-08-09 | Halliburton Energy Services, Inc. | Downhole acid injection to stimulate formation production |
US11781413B2 (en) | 2020-02-04 | 2023-10-10 | Halliburton Energy Services, Inc. | Downhole acid injection to stimulate formation production |
US11608461B2 (en) | 2020-09-29 | 2023-03-21 | Halliburton Energy Services, Inc. | Conformance for carbonate formations |
US20240002717A1 (en) * | 2022-06-29 | 2024-01-04 | Saudi Arabian Oil Company | Switchable polymers that reduce water production in a hydrocarbon-producing well |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020019318A1 (en) * | 2000-04-21 | 2002-02-14 | Harris William Franklin | Suspensions of water soluble polymers in surfactant free non-aqueous solvents |
US6476169B1 (en) | 2000-09-28 | 2002-11-05 | Halliburton Energy Services, Inc. | Methods of reducing subterranean formation water permeability |
US20040180795A1 (en) * | 2002-11-21 | 2004-09-16 | Changming Su | Electropositive production well treating fluid and method of preparing the same |
US20040229757A1 (en) * | 2003-05-16 | 2004-11-18 | Eoff Larry S. | Methods and compositions for reducing the production of water and stimulating hydrocarbon production from a subterranean formation |
US20050178549A1 (en) * | 2004-02-18 | 2005-08-18 | Eoff Larry S. | Methods of reducing the permeabilities of horizontal well bore sections |
US20050230116A1 (en) * | 2004-04-15 | 2005-10-20 | Eoff Larry S | Methods and compositions for use with spacer fluids used in subterranean well bores |
US7117942B2 (en) | 2004-06-29 | 2006-10-10 | Halliburton Energy Services, Inc. | Methods useful for controlling fluid loss during sand control operations |
Family Cites Families (209)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2278838A (en) * | 1940-03-11 | 1942-04-07 | Petrolite Corp | Composition of matter and process for preventing water-in-oil type emulsions resulting from acidization of calcareous oil-bearing strata |
US2689244A (en) | 1950-06-23 | 1954-09-14 | Phillips Petroleum Co | Process for production of chitin sulfate |
US2670329A (en) * | 1950-08-03 | 1954-02-23 | Phillips Petroleum Co | Drilling muds and methods of using same |
US2910436A (en) | 1953-10-02 | 1959-10-27 | California Research Corp | Method of treating wells with acid |
US2863832A (en) | 1954-05-14 | 1958-12-09 | California Research Corp | Method of acidizing petroliferous formations |
US2843573A (en) * | 1955-03-21 | 1958-07-15 | Rohm & Haas | New quaternary ammonium compounds in which the nitrogen atom carries an alkoxymethyl group |
US3065247A (en) | 1955-11-23 | 1962-11-20 | Petrolte Corp | Reaction product of epoxidized fatty acid esters of lower alkanols and polyamino compounds |
US2877179A (en) * | 1956-03-26 | 1959-03-10 | Cities Service Res & Dev Co | Composition for and method of inhibiting corrosion of metals |
US2819278A (en) * | 1956-05-09 | 1958-01-07 | Petrolite Corp | Reaction product of epoxidized glycerides and hydroxylated tertiary monoamines |
US3008898A (en) | 1959-06-26 | 1961-11-14 | Cities Service Res & Dev Co | Method of inhibiting corrosion |
US3052298A (en) | 1960-03-22 | 1962-09-04 | Shell Oil Co | Method and apparatus for cementing wells |
US3258428A (en) * | 1960-08-04 | 1966-06-28 | Petrolite Corp | Scale prevention |
US3251778A (en) * | 1960-08-04 | 1966-05-17 | Petrolite Corp | Process of preventing scale |
US3265512A (en) | 1960-08-04 | 1966-08-09 | Petrolite Corp | Corrosion inhibition |
US3271307A (en) | 1960-08-04 | 1966-09-06 | Petrolite Corp | Oil well treatment |
US3215199A (en) | 1963-02-21 | 1965-11-02 | Shell Oil Co | Acidizing oil formations |
DE1468014A1 (en) * | 1964-01-29 | 1969-01-09 | Henkel & Cie Gmbh | Process for the preparation of hydroxyalkyl ethers of galactomannans |
US3297090A (en) * | 1964-04-24 | 1967-01-10 | Shell Oil Co | Acidizing oil formations |
US3307630A (en) * | 1964-06-12 | 1967-03-07 | Shell Oil Co | Acidizing oil formations |
US3251415A (en) * | 1965-04-01 | 1966-05-17 | Exxon Production Research Co | Acid treating process |
US3404114A (en) | 1965-06-18 | 1968-10-01 | Dow Chemical Co | Method for preparing latexes having improved adhesive properties |
US3434971A (en) * | 1965-08-25 | 1969-03-25 | Dow Chemical Co | Composition and method for acidizing wells |
US3347789A (en) | 1966-03-04 | 1967-10-17 | Petrolite Corp | Treatment of oil wells |
US3451818A (en) * | 1966-04-19 | 1969-06-24 | Polaroid Corp | Composite rollfilm assembly for use in the diffusion transfer process |
US3382924A (en) * | 1966-09-06 | 1968-05-14 | Dow Chemical Co | Treatment of earthen formations comprising argillaceous material |
US3336980A (en) | 1967-02-09 | 1967-08-22 | Exxon Production Research Co | Sand control in wells |
US3441085A (en) * | 1967-09-07 | 1969-04-29 | Exxon Production Research Co | Method for acid treating carbonate formations |
US3489222A (en) * | 1968-12-26 | 1970-01-13 | Chevron Res | Method of consolidating earth formations without removing tubing from well |
US3601194A (en) | 1969-07-14 | 1971-08-24 | Union Oil Co | Low fluid loss well-treating composition and method |
US3647567A (en) * | 1969-11-28 | 1972-03-07 | Celanese Coatings Co | Post-dipping of acidic deposition coatings |
US3647507A (en) * | 1970-01-07 | 1972-03-07 | Johnson & Johnson | Resin composition containing a polyacrylic acid-polyacrylamide copolymer and method of using the same to control resin composition |
US3910862A (en) | 1970-01-30 | 1975-10-07 | Gaf Corp | Copolymers of vinyl pyrrolidone containing quarternary ammonium groups |
DE2250552A1 (en) | 1970-01-30 | 1974-04-18 | Gaf Corp | Filmogenic quat ammonium copolymers - use as hair fixatives ,in textile treatments etc |
US3689468A (en) | 1970-12-14 | 1972-09-05 | Rohm & Haas | Unsaturated quaternary monomers and polymers |
US3689418A (en) | 1971-01-18 | 1972-09-05 | Monsanto Co | Detergent formulations |
US3708013A (en) * | 1971-05-03 | 1973-01-02 | Mobil Oil Corp | Method and apparatus for obtaining an improved gravel pack |
US3709298A (en) * | 1971-05-20 | 1973-01-09 | Shell Oil Co | Sand pack-aided formation sand consolidation |
US3744566A (en) * | 1972-03-16 | 1973-07-10 | Calgon Corp | Secondary oil recovery process |
US4052345A (en) | 1973-12-17 | 1977-10-04 | Basf Wyandotte Corporation | Process for the preparation of polyurethane foams |
US3902557A (en) | 1974-03-25 | 1975-09-02 | Exxon Production Research Co | Treatment of wells |
US3943060A (en) * | 1974-07-26 | 1976-03-09 | Calgon Corporation | Friction reducing |
US4299710A (en) | 1975-05-30 | 1981-11-10 | Rohm And Haas Company | Drilling fluid and method |
US3983941A (en) | 1975-11-10 | 1976-10-05 | Mobil Oil Corporation | Well completion technique for sand control |
US4052343A (en) | 1975-11-10 | 1977-10-04 | Rohm And Haas Company | Crosslinked, macroreticular poly(dimethylaminoethyl methacrylate) ion-exchange resins and method of preparation by aqueous suspension polymerization using trialkylamine phase extender |
US4366072A (en) | 1976-08-13 | 1982-12-28 | Halliburton Company | Oil well treating method and composition |
CA1103008A (en) | 1976-08-13 | 1981-06-16 | Homer C. Mclaughlin | Treatment of clay formations with organic polycationic polymers |
US4366073A (en) | 1976-08-13 | 1982-12-28 | Halliburton Company | Oil well treating method and composition |
US4366071A (en) | 1976-08-13 | 1982-12-28 | Halliburton Company | Oil well treating method and composition |
US4374739A (en) * | 1976-08-13 | 1983-02-22 | Halliburton Company | Oil well treating method and composition |
US4366074A (en) | 1976-08-13 | 1982-12-28 | Halliburton Company | Oil well treating method and composition |
JPS6024122B2 (en) * | 1977-01-05 | 1985-06-11 | 三菱化学株式会社 | Method for producing bead-like polymer |
US4142595A (en) * | 1977-03-09 | 1979-03-06 | Standard Oil Company (Indiana) | Shale stabilizing drilling fluid |
US4129183A (en) | 1977-06-30 | 1978-12-12 | Texaco Inc. | Use of organic acid chrome complexes to treat clay containing formations |
US4152274A (en) * | 1978-02-09 | 1979-05-01 | Nalco Chemical Company | Method for reducing friction loss in a well fracturing process |
US4337828A (en) * | 1978-06-19 | 1982-07-06 | Magna Corporation | Method of recovering petroleum from a subterranean reservoir incorporating polyepoxide condensates of resinous polyalkylene oxide adducts and polyether polyols |
US4158521A (en) * | 1978-06-26 | 1979-06-19 | The Western Company Of North America | Method of stabilizing clay formations |
US4460627A (en) | 1978-09-28 | 1984-07-17 | Halliburton Company | Polymeric well treating method |
US4532052A (en) | 1978-09-28 | 1985-07-30 | Halliburton Company | Polymeric well treating method |
US4228277A (en) | 1979-02-12 | 1980-10-14 | Hercules Incorporated | Modified nonionic cellulose ethers |
US4306981A (en) | 1979-10-05 | 1981-12-22 | Magna Corporation | Method for breaking petroleum emulsions and the like comprising resinous polyalkylene oxide adducts |
US4552670A (en) | 1979-10-15 | 1985-11-12 | Diamond Shamrock Chemicals Company | Amphoteric water-in-oil self-inverting polymer emulsion |
US4814096A (en) * | 1981-02-06 | 1989-03-21 | The Dow Chemical Company | Enhanced oil recovery process using a hydrophobic associative composition containing a hydrophilic/hydrophobic polymer |
US4393939A (en) * | 1981-04-20 | 1983-07-19 | Halliburton Services | Clay stabilization during oil and gas well cementing operations |
US4401789A (en) | 1981-07-14 | 1983-08-30 | Halliburton Company | Enhanced oil recovery methods and systems |
US4439334A (en) * | 1981-07-14 | 1984-03-27 | Halliburton Company | Enhanced oil recovery methods and systems |
US4395340A (en) * | 1981-07-14 | 1983-07-26 | Halliburton Company | Enhanced oil recovery methods and systems |
US4441556A (en) * | 1981-08-17 | 1984-04-10 | Standard Oil Company | Diverter tool and its use |
US4536297A (en) | 1982-01-28 | 1985-08-20 | Halliburton Company | Well drilling and completion fluid composition |
US4440649A (en) * | 1982-01-28 | 1984-04-03 | Halliburton Company | Well drilling and completion fluid composition |
US4447342A (en) * | 1982-04-19 | 1984-05-08 | Halliburton Co. | Method of clay stabilization in enhanced oil recovery |
US4604216A (en) | 1982-10-19 | 1986-08-05 | Phillips Petroleum Company | Drilling fluids |
DE3400164A1 (en) * | 1983-01-14 | 1984-07-19 | Sandoz-Patent-GmbH, 7850 Lörrach | LIQUID LOSS REDUCING ADDITIVES FOR PUNCHING LIQUIDS |
US5186257A (en) * | 1983-01-28 | 1993-02-16 | Phillips Petroleum Company | Polymers useful in the recovery and processing of natural resources |
US4499214A (en) * | 1983-05-03 | 1985-02-12 | Diachem Industries, Inc. | Method of rapidly dissolving polymers in water |
US4554081A (en) | 1984-05-21 | 1985-11-19 | Halliburton Company | High density well drilling, completion and workover brines, fluid loss reducing additives therefor and methods of use |
GB8413716D0 (en) | 1984-05-30 | 1984-07-04 | Allied Colloids Ltd | Aqueous well fluids |
US4536303A (en) | 1984-08-02 | 1985-08-20 | Halliburton Company | Methods of minimizing fines migration in subterranean formations |
US4563292A (en) * | 1984-08-02 | 1986-01-07 | Halliburton Company | Methods for stabilizing fines contained in subterranean formations |
US4627926A (en) | 1984-09-19 | 1986-12-09 | Exxon Research And Engineering Company | Thermally stable borehole fluids |
US4536305A (en) | 1984-09-21 | 1985-08-20 | Halliburton Company | Methods for stabilizing swelling clays or migrating fines in subterranean formations |
US4608139A (en) | 1985-06-21 | 1986-08-26 | Scm Corporation | Electrocoating process using shear stable cationic latex |
US4619776A (en) | 1985-07-02 | 1986-10-28 | Texas United Chemical Corp. | Crosslinked fracturing fluids |
US4992182A (en) | 1985-11-21 | 1991-02-12 | Union Oil Company Of California | Scale removal treatment |
US4730028A (en) * | 1986-03-28 | 1988-03-08 | Exxon Research And Engineering Company | Process for preparing hydrophobically associating terpolymers containing sulfonate functionality |
US4662448A (en) * | 1986-04-25 | 1987-05-05 | Atlantic Richfield Company | Well treatment method using sodium silicate to seal formation |
US4959432A (en) | 1986-05-19 | 1990-09-25 | Union Carbide Chemicals And Plastics Company Inc. | Acid viscosifier compositions |
US4693639A (en) | 1986-06-25 | 1987-09-15 | Halliburton Company | Clay stabilizing agent preparation and use |
US4737295A (en) | 1986-07-21 | 1988-04-12 | Venture Chemicals, Inc. | Organophilic polyphenolic acid adducts |
US4828725A (en) * | 1986-10-01 | 1989-05-09 | Air Products And Chemicals, Inc. | Completion fluids containing high molecular weight poly(vinylamines) |
US4856590A (en) | 1986-11-28 | 1989-08-15 | Mike Caillier | Process for washing through filter media in a production zone with a pre-packed screen and coil tubing |
US4702319A (en) | 1986-12-29 | 1987-10-27 | Exxon Research And Engineering Company | Enhanced oil recovery with hydrophobically associating polymers containing sulfonate functionality |
US4870167A (en) | 1987-03-02 | 1989-09-26 | Hi-Tek Polymers, Inc. | Hydrophobically modified non-ionic polygalactomannan ethers |
US4828726A (en) * | 1987-09-11 | 1989-05-09 | Halliburton Company | Stabilizing clayey formations |
US5071934A (en) | 1987-12-21 | 1991-12-10 | Exxon Research And Engineering Company | Cationic hydrophobic monomers and polymers |
IT1224421B (en) | 1987-12-29 | 1990-10-04 | Lamberti Flli Spa | MODIFIED GALATTOMANNANS AND REALIVE PREPARATION PROCEDURE |
US4941537A (en) | 1988-02-25 | 1990-07-17 | Hi-Tek Polymers, Inc. | Method for reducing the viscosity of aqueous fluid |
US5248665A (en) | 1988-03-14 | 1993-09-28 | Shell Oil Company | Drilling fluids comprising polycyclic polyether polyol |
NO893150L (en) | 1988-08-15 | 1990-02-16 | Baroid Technology Inc | PROCEDURE FOR DRILLING A DRILL IN EARTH AND DRILL FOR USE IN THE PROCEDURE. |
US4973641A (en) | 1988-11-18 | 1990-11-27 | National Starch And Chemical Investment Holding Corporation | Polysaccharide graft copolymers containing reactive aminoethyl halide group |
US4917186A (en) | 1989-02-16 | 1990-04-17 | Phillips Petroleum Company | Altering subterranean formation permeability |
US5160642A (en) | 1990-05-25 | 1992-11-03 | Petrolite Corporation | Polyimide quaternary salts as clay stabilization agents |
US5105886A (en) * | 1990-10-24 | 1992-04-21 | Mobil Oil Corporation | Method for the control of solids accompanying hydrocarbon production from subterranean formations |
US5256651A (en) | 1991-01-22 | 1993-10-26 | Rhone-Poulenc, Inc. | Hydrophilic-hydrophobic derivatives of polygalactomannans containing tertiary amine functionality |
US5099923A (en) | 1991-02-25 | 1992-03-31 | Nalco Chemical Company | Clay stabilizing method for oil and gas well treatment |
US5197544A (en) * | 1991-02-28 | 1993-03-30 | Halliburton Company | Method for clay stabilization with quaternary amines |
US5097904A (en) * | 1991-02-28 | 1992-03-24 | Halliburton Company | Method for clay stabilization with quaternary amines |
US5146986A (en) | 1991-03-15 | 1992-09-15 | Halliburton Company | Methods of reducing the water permeability of water and oil producing subterranean formations |
US5244042A (en) | 1991-05-07 | 1993-09-14 | Union Oil Company Of California | Lanthanide-crosslinked polymers for subterranean injection |
US5208216A (en) * | 1991-06-13 | 1993-05-04 | Nalco Chemical Company | Acrylamide terpolymer shale stabilizing additive for low viscosity oil and gas drilling operations |
US5908814A (en) * | 1991-10-28 | 1999-06-01 | M-I L.L.C. | Drilling fluid additive and method for inhibiting hydration |
US5424284A (en) * | 1991-10-28 | 1995-06-13 | M-I Drilling Fluids Company | Drilling fluid additive and method for inhibiting hydration |
FR2686892B1 (en) | 1992-01-31 | 1995-01-13 | Inst Francais Du Petrole | PROCESS FOR INHIBITING REACTIVE CLAY FORMATIONS AND APPLICATION TO A DRILLING FLUID. |
US5759962A (en) * | 1992-01-31 | 1998-06-02 | Institut Francais Du Petrole | Method for inhibiting reactive argillaceous formations and use thereof in a drilling fluid |
DK0577931T3 (en) * | 1992-04-10 | 1999-02-01 | Clariant Gmbh | Process for reducing or completely adjusting the water influx through oil and / or oil extraction wells |
US5271466A (en) | 1992-10-30 | 1993-12-21 | Halliburton Company | Subterranean formation treating with dual delayed crosslinking gelled fluids |
US5387675A (en) | 1993-03-10 | 1995-02-07 | Rhone-Poulenc Specialty Chemicals Co. | Modified hydrophobic cationic thickening compositions |
CA2151152C (en) * | 1993-11-19 | 1999-08-10 | Kevin W. Smith | Method of treating shale and clay in hydrocarbon formation drilling |
US5643460A (en) | 1994-01-14 | 1997-07-01 | Nalco/Exxon Energy Chemicals, L. P. | Method for separating oil from water in petroleum production |
FR2716928B1 (en) | 1994-03-03 | 1996-05-03 | Inst Francais Du Petrole | Water-based process and fluid using hydrophobically modified cellulosic derivatives as a filtrate reducer. |
US5445223A (en) | 1994-03-15 | 1995-08-29 | Dowell, A Division Of Schlumberger Technology Corporation | Delayed borate crosslinked fracturing fluid having increased temperature range |
FR2719601B1 (en) * | 1994-05-04 | 1996-06-28 | Inst Francais Du Petrole | Water-based process and fluid for controlling the dispersion of solids. Application to drilling. |
FR2719600B1 (en) * | 1994-05-04 | 1996-06-14 | Inst Francais Du Petrole | Process and fluid used in a well - Application to drilling. |
US5681796A (en) | 1994-07-29 | 1997-10-28 | Schlumberger Technology Corporation | Borate crosslinked fracturing fluid and method |
US5566760A (en) | 1994-09-02 | 1996-10-22 | Halliburton Company | Method of using a foamed fracturing fluid |
US5646093A (en) | 1994-09-13 | 1997-07-08 | Rhone-Poulenc Inc. | Modified polygalactomannans as oil field shale inhibitors |
FR2729181A1 (en) * | 1995-01-10 | 1996-07-12 | Inst Francais Du Petrole | WATER-BASED PROCESS AND FLUID USING HYDROPHOBICALLY MODIFIED GUARS AS A FILTRATE REDUCER |
GB9510396D0 (en) * | 1995-05-23 | 1995-07-19 | Allied Colloids Ltd | Polymers for drilling and reservoir fluids and their use |
US5704426A (en) * | 1996-03-20 | 1998-01-06 | Schlumberger Technology Corporation | Zonal isolation method and apparatus |
US5735349A (en) * | 1996-08-16 | 1998-04-07 | Bj Services Company | Compositions and methods for modifying the permeability of subterranean formations |
US5964295A (en) | 1996-10-09 | 1999-10-12 | Schlumberger Technology Corporation, Dowell Division | Methods and compositions for testing subterranean formations |
US6435277B1 (en) | 1996-10-09 | 2002-08-20 | Schlumberger Technology Corporation | Compositions containing aqueous viscosifying surfactants and methods for applying such compositions in subterranean formations |
US5944106A (en) | 1997-08-06 | 1999-08-31 | Halliburton Energy Services, Inc. | Well treating fluids and methods |
US6070664A (en) * | 1998-02-12 | 2000-06-06 | Halliburton Energy Services | Well treating fluids and methods |
AU736803B2 (en) | 1997-08-06 | 2001-08-02 | Halliburton Energy Services, Inc. | Well treating fluids and methods |
US5887653A (en) * | 1997-08-15 | 1999-03-30 | Plainsman Technology, Inc. | Method for clay stabilization |
DE19752093C2 (en) | 1997-11-25 | 2000-10-26 | Clariant Gmbh | Water-soluble copolymers based on acrylamide and their use as cementation aids |
GB2332224B (en) * | 1997-12-13 | 2000-01-19 | Sofitech Nv | Gelling composition for wellbore service fluids |
US6516885B1 (en) * | 1998-02-18 | 2003-02-11 | Lattice Intellectual Property Ltd | Reducing water flow |
GB2335428B (en) | 1998-03-20 | 2001-03-14 | Sofitech Nv | Hydrophobically modified polymers for water control |
US6242390B1 (en) * | 1998-07-31 | 2001-06-05 | Schlumberger Technology Corporation | Cleanup additive |
US6124245A (en) | 1998-10-07 | 2000-09-26 | Phillips Petroleum Company | Drilling fluid additive and process therewith |
US6607035B1 (en) | 1998-12-04 | 2003-08-19 | Halliburton Energy Services, Inc. | Preventing flow through subterranean zones |
US6228812B1 (en) * | 1998-12-10 | 2001-05-08 | Bj Services Company | Compositions and methods for selective modification of subterranean formation permeability |
US6780822B2 (en) | 1998-12-28 | 2004-08-24 | Venture Chemicals, Inc. | Anhydride-modified chitosan, method of preparation thereof, and fluids containing same |
US6562762B2 (en) * | 1998-12-28 | 2003-05-13 | Venture Chemicals, Inc. | Method of and composition for reducing the loss of fluid during well drilling, completion or workover operations |
US6291404B2 (en) | 1998-12-28 | 2001-09-18 | Venture Innovations, Inc. | Viscosified aqueous chitosan-containing well drilling and servicing fluids |
US6358889B2 (en) * | 1998-12-28 | 2002-03-19 | Venture Innovations, Inc. | Viscosified aqueous chitosan-containing well drilling and servicing fluids |
US6656885B2 (en) | 1998-12-28 | 2003-12-02 | Venture Innovations, Inc. | Anhydride-modified chitosan, method of preparation thereof, and fluids containing same |
DE19909231C2 (en) * | 1999-03-03 | 2001-04-19 | Clariant Gmbh | Water-soluble copolymers based on AMPS and their use as drilling aids |
US6187839B1 (en) * | 1999-03-03 | 2001-02-13 | Halliburton Energy Services, Inc. | Methods of sealing compositions and methods |
US6281172B1 (en) | 1999-04-07 | 2001-08-28 | Akzo Nobel Nv | Quaternary nitrogen containing amphoteric water soluble polymers and their use in drilling fluids |
US6209646B1 (en) * | 1999-04-21 | 2001-04-03 | Halliburton Energy Services, Inc. | Controlling the release of chemical additives in well treating fluids |
US6237687B1 (en) * | 1999-06-09 | 2001-05-29 | Eclipse Packer Company | Method and apparatus for placing a gravel pack in an oil and gas well |
GB2351098B (en) * | 1999-06-18 | 2004-02-04 | Sofitech Nv | Water based wellbore fluids |
EP1257587B1 (en) | 1999-07-09 | 2004-06-23 | Dow Global Technologies Inc. | Hydrogenation of unsaturated polymers using divalent diene-containing bis-cyclopentadienyl group iv metal catalysts |
US6283210B1 (en) | 1999-09-01 | 2001-09-04 | Halliburton Energy Services, Inc. | Proactive conformance for oil or gas wells |
US6253851B1 (en) | 1999-09-20 | 2001-07-03 | Marathon Oil Company | Method of completing a well |
FR2804953B1 (en) * | 2000-02-10 | 2002-07-26 | Inst Francais Du Petrole | CEMENT DAIRY HAVING HYDROPHOBIC POLYMERS |
US6609578B2 (en) | 2000-02-11 | 2003-08-26 | Mo M-I Llc | Shale hydration inhibition agent and method of use |
US6767869B2 (en) | 2000-02-29 | 2004-07-27 | Bj Services Company | Well service fluid and method of making and using the same |
US6364016B1 (en) * | 2000-10-26 | 2002-04-02 | Halliburton Energy Services, Inc. | Methods of reducing the water permeability of subterranean formations |
US6627719B2 (en) | 2001-01-31 | 2003-09-30 | Ondeo Nalco Company | Cationic latex terpolymers for sludge dewatering |
US6933381B2 (en) | 2001-02-02 | 2005-08-23 | Charles B. Mallon | Method of preparing modified cellulose ether |
US6359047B1 (en) * | 2001-03-20 | 2002-03-19 | Isp Investments Inc. | Gas hydrate inhibitor |
US6939536B2 (en) | 2001-04-16 | 2005-09-06 | Wsp Chemicals & Technology, Llc | Cosmetic compositions containing water-soluble polymer complexes |
US7056868B2 (en) * | 2001-07-30 | 2006-06-06 | Cabot Corporation | Hydrophobe associative polymers and compositions and methods employing them |
US6601648B2 (en) | 2001-10-22 | 2003-08-05 | Charles D. Ebinger | Well completion method |
US6855672B2 (en) * | 2001-11-07 | 2005-02-15 | Baker Hughes Incorporated | Copolymers useful for gelling acids |
US6695055B2 (en) | 2001-11-15 | 2004-02-24 | Wm. Marsh Rice University | Subterranean formation water permeability reducing methods |
US6497283B1 (en) * | 2001-11-19 | 2002-12-24 | Halliburton Energy Services, Inc. | Well cement additives, compositions and methods |
US6790812B2 (en) | 2001-11-30 | 2004-09-14 | Baker Hughes Incorporated | Acid soluble, high fluid loss pill for lost circulation |
US6626241B2 (en) | 2001-12-06 | 2003-09-30 | Halliburton Energy Services, Inc. | Method of frac packing through existing gravel packed screens |
US6569983B1 (en) * | 2001-12-20 | 2003-05-27 | Ondeo Nalco Energy Services, L.P. | Method and composition for recovering hydrocarbon fluids from a subterranean reservoir |
US6787506B2 (en) | 2002-04-03 | 2004-09-07 | Nalco Energy Services, L.P. | Use of dispersion polymers as friction reducers in aqueous fracturing fluids |
US7741251B2 (en) | 2002-09-06 | 2010-06-22 | Halliburton Energy Services, Inc. | Compositions and methods of stabilizing subterranean formations containing reactive shales |
US7091159B2 (en) | 2002-09-06 | 2006-08-15 | Halliburton Energy Services, Inc. | Compositions for and methods of stabilizing subterranean formations containing clays |
US7008908B2 (en) * | 2002-11-22 | 2006-03-07 | Schlumberger Technology Corporation | Selective stimulation with selective water reduction |
US6846420B2 (en) * | 2002-12-19 | 2005-01-25 | Halliburton Energy Services, Inc. | Process for removing oil from solid materials recovered from a well bore |
US7220708B2 (en) * | 2003-02-27 | 2007-05-22 | Halliburton Energy Services, Inc. | Drilling fluid component |
US6764981B1 (en) | 2003-03-21 | 2004-07-20 | Halliburton Energy Services, Inc. | Well treatment fluid and methods with oxidized chitosan-based compound |
US6981552B2 (en) * | 2003-03-21 | 2006-01-03 | Halliburton Energy Services, Inc. | Well treatment fluid and methods with oxidized polysaccharide-based polymers |
US7007752B2 (en) * | 2003-03-21 | 2006-03-07 | Halliburton Energy Services, Inc. | Well treatment fluid and methods with oxidized polysaccharide-based polymers |
US6962203B2 (en) | 2003-03-24 | 2005-11-08 | Owen Oil Tools Lp | One trip completion process |
US8181703B2 (en) | 2003-05-16 | 2012-05-22 | Halliburton Energy Services, Inc. | Method useful for controlling fluid loss in subterranean formations |
US8251141B2 (en) | 2003-05-16 | 2012-08-28 | Halliburton Energy Services, Inc. | Methods useful for controlling fluid loss during sand control operations |
US20040229756A1 (en) | 2003-05-16 | 2004-11-18 | Eoff Larry S. | Method for stimulating hydrocarbon production and reducing the production of water from a subterranean formation |
US8631869B2 (en) | 2003-05-16 | 2014-01-21 | Leopoldo Sierra | Methods useful for controlling fluid loss in subterranean treatments |
US7182136B2 (en) * | 2003-07-02 | 2007-02-27 | Halliburton Energy Services, Inc. | Methods of reducing water permeability for acidizing a subterranean formation |
US8278250B2 (en) | 2003-05-16 | 2012-10-02 | Halliburton Energy Services, Inc. | Methods useful for diverting aqueous fluids in subterranean operations |
US8091638B2 (en) * | 2003-05-16 | 2012-01-10 | Halliburton Energy Services, Inc. | Methods useful for controlling fluid loss in subterranean formations |
US6978836B2 (en) | 2003-05-23 | 2005-12-27 | Halliburton Energy Services, Inc. | Methods for controlling water and particulate production |
US7036587B2 (en) * | 2003-06-27 | 2006-05-02 | Halliburton Energy Services, Inc. | Methods of diverting treating fluids in subterranean zones and degradable diverting materials |
US7036589B2 (en) * | 2003-08-14 | 2006-05-02 | Halliburton Energy Services, Inc. | Methods for fracturing stimulation |
US7081439B2 (en) | 2003-11-13 | 2006-07-25 | Schlumberger Technology Corporation | Methods for controlling the fluid loss properties of viscoelastic surfactant based fluids |
US7563750B2 (en) | 2004-01-24 | 2009-07-21 | Halliburton Energy Services, Inc. | Methods and compositions for the diversion of aqueous injection fluids in injection operations |
US7114568B2 (en) | 2004-04-15 | 2006-10-03 | Halliburton Energy Services, Inc. | Hydrophobically modified polymers for a well completion spacer fluid |
US7216707B2 (en) * | 2004-06-21 | 2007-05-15 | Halliburton Energy Services, Inc. | Cement compositions with improved fluid loss characteristics and methods of cementing using such cement compositions |
US7273099B2 (en) | 2004-12-03 | 2007-09-25 | Halliburton Energy Services, Inc. | Methods of stimulating a subterranean formation comprising multiple production intervals |
US7398825B2 (en) | 2004-12-03 | 2008-07-15 | Halliburton Energy Services, Inc. | Methods of controlling sand and water production in subterranean zones |
EP1831341A1 (en) * | 2004-12-06 | 2007-09-12 | The Procter and Gamble Company | Fabric enhancing composition |
US20080110624A1 (en) * | 2005-07-15 | 2008-05-15 | Halliburton Energy Services, Inc. | Methods for controlling water and particulate production in subterranean wells |
US7493957B2 (en) * | 2005-07-15 | 2009-02-24 | Halliburton Energy Services, Inc. | Methods for controlling water and sand production in subterranean wells |
US20070114032A1 (en) * | 2005-11-22 | 2007-05-24 | Stegent Neil A | Methods of consolidating unconsolidated particulates in subterranean formations |
US7678742B2 (en) * | 2006-09-20 | 2010-03-16 | Halliburton Energy Services, Inc. | Drill-in fluids and associated methods |
US7678743B2 (en) | 2006-09-20 | 2010-03-16 | Halliburton Energy Services, Inc. | Drill-in fluids and associated methods |
US7687438B2 (en) * | 2006-09-20 | 2010-03-30 | Halliburton Energy Services, Inc. | Drill-in fluids and associated methods |
US20080139411A1 (en) * | 2006-12-07 | 2008-06-12 | Harris Phillip C | Methods of treating subterranean formations using hydrophobically modified polymers and compositions of the same |
US7730950B2 (en) | 2007-01-19 | 2010-06-08 | Halliburton Energy Services, Inc. | Methods for treating intervals of a subterranean formation having variable permeability |
US7934557B2 (en) | 2007-02-15 | 2011-05-03 | Halliburton Energy Services, Inc. | Methods of completing wells for controlling water and particulate production |
-
2009
- 2009-08-10 US US12/538,203 patent/US8420576B2/en active Active
-
2010
- 2010-07-29 MX MX2012001536A patent/MX2012001536A/en active IP Right Grant
- 2010-07-29 AR ARP100102755A patent/AR077607A1/en active IP Right Grant
- 2010-07-29 EP EP10739671.5A patent/EP2464708B1/en active Active
- 2010-07-29 AU AU2010283625A patent/AU2010283625B2/en active Active
- 2010-07-29 CA CA2768594A patent/CA2768594C/en active Active
- 2010-07-29 WO PCT/GB2010/001448 patent/WO2011018604A1/en active Application Filing
-
2012
- 2012-06-27 US US13/534,166 patent/US8623793B2/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020019318A1 (en) * | 2000-04-21 | 2002-02-14 | Harris William Franklin | Suspensions of water soluble polymers in surfactant free non-aqueous solvents |
US6476169B1 (en) | 2000-09-28 | 2002-11-05 | Halliburton Energy Services, Inc. | Methods of reducing subterranean formation water permeability |
US20040180795A1 (en) * | 2002-11-21 | 2004-09-16 | Changming Su | Electropositive production well treating fluid and method of preparing the same |
US20040229757A1 (en) * | 2003-05-16 | 2004-11-18 | Eoff Larry S. | Methods and compositions for reducing the production of water and stimulating hydrocarbon production from a subterranean formation |
US20050178549A1 (en) * | 2004-02-18 | 2005-08-18 | Eoff Larry S. | Methods of reducing the permeabilities of horizontal well bore sections |
US20050230116A1 (en) * | 2004-04-15 | 2005-10-20 | Eoff Larry S | Methods and compositions for use with spacer fluids used in subterranean well bores |
US7117942B2 (en) | 2004-06-29 | 2006-10-10 | Halliburton Energy Services, Inc. | Methods useful for controlling fluid loss during sand control operations |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015042489A1 (en) * | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Method of using surface modifying metallic treatment agents to treat subterranean formations |
US9562188B2 (en) | 2013-09-20 | 2017-02-07 | Baker Hughes Incorporated | Composites for use in stimulation and sand control operations |
US9683431B2 (en) | 2013-09-20 | 2017-06-20 | Baker Hughes Incorporated | Method of using surface modifying metallic treatment agents to treat subterranean formations |
US9822621B2 (en) | 2013-09-20 | 2017-11-21 | Baker Hughes, A Ge Company, Llc | Method of using surface modifying treatment agents to treat subterranean formations |
US10047280B2 (en) | 2013-09-20 | 2018-08-14 | Baker Hughes, A Ge Company, Llc | Organophosphorus containing composites for use in well treatment operations |
RU2670804C2 (en) * | 2013-09-20 | 2018-10-25 | Бейкер Хьюз Инкорпорейтед | Method of using surface modifying metallic treatment agents to treat subterranean formations |
RU2670802C2 (en) * | 2013-09-20 | 2018-10-25 | Бейкер Хьюз Инкорпорейтед | Composites for use in stimulation of oil production and sand control operations |
RU2670802C9 (en) * | 2013-09-20 | 2018-11-26 | Бейкер Хьюз Инкорпорейтед | Composites for use in stimulation of oil production and sand control operations |
RU2670804C9 (en) * | 2013-09-20 | 2018-11-28 | Бейкер Хьюз Инкорпорейтед | Method of using surface modifying metallic treatment agents to treat subterranean formations |
US10227846B2 (en) | 2013-09-20 | 2019-03-12 | Baker Hughes, A Ge Company, Llc | Method of inhibiting fouling on a metallic surface using a surface modifying treatment agent |
US9701892B2 (en) | 2014-04-17 | 2017-07-11 | Baker Hughes Incorporated | Method of pumping aqueous fluid containing surface modifying treatment agent into a well |
US10472555B2 (en) | 2016-04-08 | 2019-11-12 | Schlumberger Technology Corporation | Polymer gel for water control applications |
Also Published As
Publication number | Publication date |
---|---|
US20120264885A1 (en) | 2012-10-18 |
MX2012001536A (en) | 2012-03-29 |
CA2768594C (en) | 2014-03-25 |
CA2768594A1 (en) | 2011-02-17 |
US8623793B2 (en) | 2014-01-07 |
AR077607A1 (en) | 2011-09-07 |
EP2464708A1 (en) | 2012-06-20 |
US20110034351A1 (en) | 2011-02-10 |
AU2010283625A1 (en) | 2012-02-09 |
EP2464708B1 (en) | 2020-06-17 |
US8420576B2 (en) | 2013-04-16 |
AU2010283625B2 (en) | 2013-05-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8623793B2 (en) | Hydrophobically and cationically modified relative permeability modifiers and associated methods | |
US8008235B2 (en) | Permeability-modifying drilling fluids and methods of use | |
US7730950B2 (en) | Methods for treating intervals of a subterranean formation having variable permeability | |
US8387694B2 (en) | Methods for placement of sealant in subterranean intervals | |
US9562423B2 (en) | Acid diversion treatments in injection wells using permeability modifiers | |
US20060283592A1 (en) | Method useful for controlling fluid loss in subterranean formations | |
WO2005003515A1 (en) | Methods of reducing water permeability for acidizing a subterranean formation | |
US8991495B2 (en) | Methods for protecting a hydrocarbon-producing zone of a subterranean formation using a relative permeability modifier | |
CN111594117A (en) | Crosslinking of swellable polymers with PEI | |
CA2933962C (en) | Methods for improving the distribution of a sealant composition in a wellbore and treatment fluids providing the same | |
NO882396L (en) | PROCEDURE FOR REDUCING PERMEABILITY IN HIGH-PERMEABLE ZONES IN OIL AND GAS FORMS. | |
US9458370B2 (en) | Methods for pre-emptively controlling undesirable water production from an oil or gas well | |
US9644130B2 (en) | Reaction products of acrylamide polymers and methods for use thereof as relative permeability modifiers | |
US10337282B2 (en) | Methods and compositions for reducing water production in fractures or voids in subterranean formations | |
US9869170B2 (en) | Methods of controlling water production in horizontal wells with multistage fractures |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10739671 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010283625 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2768594 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2012/001536 Country of ref document: MX |
|
ENP | Entry into the national phase |
Ref document number: 2010283625 Country of ref document: AU Date of ref document: 20100729 Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010739671 Country of ref document: EP |