WO2008089391A1 - Fluorinated surfactants and methods of using the same - Google Patents

Fluorinated surfactants and methods of using the same Download PDF

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Publication number
WO2008089391A1
WO2008089391A1 PCT/US2008/051409 US2008051409W WO2008089391A1 WO 2008089391 A1 WO2008089391 A1 WO 2008089391A1 US 2008051409 W US2008051409 W US 2008051409W WO 2008089391 A1 WO2008089391 A1 WO 2008089391A1
Authority
WO
WIPO (PCT)
Prior art keywords
foam
fluorinated polymeric
polymeric surfactant
nonionic fluorinated
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2008/051409
Other languages
English (en)
French (fr)
Inventor
Patricia M. Savu
Michael J. Sierakowski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to CN2008800026644A priority Critical patent/CN101589076B/zh
Priority to EP08727891.7A priority patent/EP2109631B1/en
Priority to JP2009546530A priority patent/JP2010516451A/ja
Priority to US12/523,361 priority patent/US8176981B2/en
Publication of WO2008089391A1 publication Critical patent/WO2008089391A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09K8/02—Well-drilling compositions
    • C09K8/38—Gaseous or foamed well-drilling compositions
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C08F220/68—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/007—Organic compounds containing halogen
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/26—Sulfonamides
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • 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
    • C09K8/516—Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls characterised by their form or by the form of their components, e.g. encapsulated material
    • C09K8/518—Foams
    • 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
    • C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
    • C09K8/536—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning characterised by their form or by the form of their components, e.g. encapsulated material
    • 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
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
    • 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
    • C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
    • C09K8/604—Polymeric surfactants
    • 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
    • C09K8/70—Compositions for forming crevices or fractures characterised by their form or by the form of their components, e.g. foams
    • C09K8/703—Foams
    • 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
    • C09K8/92—Compositions for stimulating production by acting on the underground formation characterised by their form or by the form of their components, e.g. encapsulated material
    • C09K8/94—Foams
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/904—Process of making fluids or additives therefor
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/91—Earth boring fluid devoid of discrete aqueous phase
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/922—Fracture fluid

Definitions

  • Fluorinated surfactants have been widely used, for example, as foaming agents and leveling agents for many years.
  • the foaming and leveling properties of fluorinated surfactants have made them useful in many industries (e.g., oil and gas and textiles) for many applications (e.g., industrial coatings).
  • R 1 is alkyl of 16 to 24 carbon atoms; and n is an integer from 2 to 11; and forming gas bubbles in the composition to make the foam.
  • nonionic fluorinated polymeric surfactants according to the present invention provide hydrocarbon foams that are more stable than foams comprising analogous nonionic fluorinated polymeric surfactants containing perfluorooctanesulfonamido groups.
  • ionic groups e.g., salts
  • Forming gas bubbles e.g., nitrogen, carbon dioxide, and air
  • a composition comprising a liquid hydrocarbon and a nonionic fluorinated polymeric surfactant according to the present invention
  • Useful mechanical foaming mechanisms include agitating (e.g., shaking, stirring, and whipping) the composition, injecting gas into the composition (e.g., inserting a nozzle beneath the surface of the composition and blowing gas into the composition) and combinations thereof.
  • Coating formulations are typically applied, dried, and optionally heated, leaving the finished product with a solid coating.
  • the addition of fluorinated surfactants according to the present invention may improve the film forming properties of some formulations by improving the ability of the coating to wet the substrate and/or by allowing for even evaporation of solvent (i.e., leveling) during film formation.
  • Examples 8 to 11 were prepared and tested according to the method of Example 1 except using the monomers and amounts shown in Table 2, below, and adding an additional 122 g of ethyl acetate at the end of the reaction time before cooling to room temperature.
  • the results from the foam testing of Examples 8 to 11 are given in Table 2, below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/US2008/051409 2007-01-19 2008-01-18 Fluorinated surfactants and methods of using the same Ceased WO2008089391A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN2008800026644A CN101589076B (zh) 2007-01-19 2008-01-18 氟化表面活性剂及其使用方法
EP08727891.7A EP2109631B1 (en) 2007-01-19 2008-01-18 Fluorinated surfactants and methods of using the same
JP2009546530A JP2010516451A (ja) 2007-01-19 2008-01-18 フッ素化界面活性剤及びその使用方法
US12/523,361 US8176981B2 (en) 2007-01-19 2008-01-18 Fluorinated surfactants and methods of using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US789407P 2007-01-19 2007-01-19
US61/007,894 2007-01-19

Publications (1)

Publication Number Publication Date
WO2008089391A1 true WO2008089391A1 (en) 2008-07-24

Family

ID=39493414

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/051409 Ceased WO2008089391A1 (en) 2007-01-19 2008-01-18 Fluorinated surfactants and methods of using the same

Country Status (5)

Country Link
US (1) US8176981B2 (https=)
EP (1) EP2109631B1 (https=)
JP (1) JP2010516451A (https=)
CN (1) CN101589076B (https=)
WO (1) WO2008089391A1 (https=)

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WO2009085904A1 (en) * 2007-12-21 2009-07-09 3M Innovative Properties Company Methods for treating hydrocarbon-bearing formations with fluorinated polymer compositions
WO2010080353A3 (en) * 2008-12-18 2010-10-07 3M Innovative Properties Company Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions
US20100288962A1 (en) * 2007-10-05 2010-11-18 Romain Severac Fluoropolymer
US8258341B2 (en) 2009-07-10 2012-09-04 E.I. Du Pont De Nemours And Company Polyfluorosulfonamido amine and intermediate
US8268186B2 (en) 2009-10-15 2012-09-18 E. I. Du Pont De Nemours And Company Fluorinated amphoteric surfactants
RU2487908C2 (ru) * 2010-09-17 2013-07-20 КЛИАРВОТЕР ИНТЕРНЭШНЛ, ЭлЭлСи Дополнительные поверхностно-активные композиции и способы их изготовления и применения
US8729138B2 (en) 2010-03-25 2014-05-20 E I Du Pont De Nemours And Company Mixture of polyfluoroalkylsulfonamido alkyl amines
US8779196B2 (en) 2010-03-25 2014-07-15 E I Du Pont De Nemours And Company Polyfluoroalkylsulfonamido alkyl halide intermediate
CN104761687A (zh) * 2015-03-20 2015-07-08 成都理工大学 耐温含氟高分子表面活性剂的制备方法
CN104761686A (zh) * 2015-03-20 2015-07-08 成都理工大学 一种含碳氢和碳氟疏水链的高分子表面活性剂的制备方法
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US8629089B2 (en) 2008-12-18 2014-01-14 3M Innovative Properties Company Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions
CN102482568B (zh) 2009-07-09 2013-08-14 3M创新有限公司 用氟化两性化合物处理碳酸盐含烃地层的方法
WO2012088056A2 (en) 2010-12-20 2012-06-28 3M Innovative Properties Company Methods for treating carbonate hydrocarbon-bearing formations with fluorinated amine oxides
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EP2663608A4 (en) 2011-01-13 2014-07-09 3M Innovative Properties Co PROCESSES FOR TREATING SILICOCLASTIC PETROLEASE FORMATIONS USING FLUORINATED AMINE OXIDES
US9222350B2 (en) 2011-06-21 2015-12-29 Diamond Innovations, Inc. Cutter tool insert having sensing device
US9803452B2 (en) 2012-08-31 2017-10-31 Halliburton Energy Services, Inc. Fluorous additives for use in a fluorous-based treatment fluid
US8770287B2 (en) * 2012-10-16 2014-07-08 Halliburton Energy Services, Inc. Defoaming agent compositions and methods of making and using same
WO2014078825A1 (en) 2012-11-19 2014-05-22 3M Innovative Properties Company Composition including a fluorinated polymer and a non-fluorinated polymer and methods of making and using the same
US10106724B2 (en) 2012-11-19 2018-10-23 3M Innovative Properties Company Method of contacting hydrocarbon-bearing formations with fluorinated ionic polymers
US9777170B2 (en) * 2014-02-25 2017-10-03 The Chemours Company Tt, Llc Fluorinated polymer additives derived using hydrophilic chain transfer agents for architectural coatings
US20150252656A1 (en) 2014-03-05 2015-09-10 Aculon, Inc. Methods For Recovering Hydrocarbon Materials From Subterranean Formations
WO2017189388A1 (en) 2016-04-25 2017-11-02 3M Innovative Properties Company Composite particles for curing epoxy resin compositions and curable and cured epoxy resin compositions prepared using the particles
CN113891900A (zh) 2019-05-29 2022-01-04 沙特阿拉伯石油公司 聚合物纳米粒子的流动合成
US11566165B2 (en) 2019-05-30 2023-01-31 Saudi Arabian Oil Company Polymers and nanoparticles for flooding
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US11773715B2 (en) 2020-09-03 2023-10-03 Saudi Arabian Oil Company Injecting multiple tracer tag fluids into a wellbore
CN114621110B (zh) * 2020-12-10 2025-01-21 中石化石油工程技术服务有限公司 一种油基泡沫钻井液用含氟表面活性剂及其制备方法
US11660595B2 (en) 2021-01-04 2023-05-30 Saudi Arabian Oil Company Microfluidic chip with multiple porosity regions for reservoir modeling
US11534759B2 (en) 2021-01-22 2022-12-27 Saudi Arabian Oil Company Microfluidic chip with mixed porosities for reservoir modeling
US12253467B2 (en) 2021-12-13 2025-03-18 Saudi Arabian Oil Company Determining partition coefficients of tracer analytes
US11718780B2 (en) 2021-12-15 2023-08-08 Saudi Arabian Oil Company Foamed scale removal and inhibition method for subterranean formation
US12060520B2 (en) * 2021-12-15 2024-08-13 Aramco Services Company Foamed wettability alteration treatment for deep condensate and water blockage in gas reservoirs
US12000278B2 (en) 2021-12-16 2024-06-04 Saudi Arabian Oil Company Determining oil and water production rates in multiple production zones from a single production well
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