Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
  • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
  • C07D213/20—Quaternary compounds thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
• • 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
  • C09K23/12—Sulfonates of aromatic or alkylated aromatic compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
  • C09K8/02—Well-drilling compositions
  • C09K8/38—Gaseous or foamed well-drilling compositions
• • 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

Definitions

• This invention relates to a fluorinated pyridinium cationic compound for use as a surfactant or foaming agent for lowering surface tension in an aqueous medium or solvent medium.
• Fluorinated cationic compounds such as perfluoroalkyl quaternary ammonium derivatives are known in art, which have a saturated perfluoroalkyl terminal chain.
• fluorinated cationic compounds disclosed in U.S. Pat. No. 4,836,958 contain such a perfluoroalkyl terminal chain group having up to 18 carbon atoms.
• Commercially available fluorinated pyridinium cationic surfactants usually contain a saturated perfluoroalkyl terminal chain of at least 8 or more carbons.
• a shorter perfluoroalkyl chain, or one interrupted with a non-fluorinated atom would have decreased performance because the individual perfluoroalkyl chains are not maintained in a parallel configuration.
• fluorinated surfactants having interrupted fluorinated chains while still providing equivalent or even better surface properties compared to those fluorinated surfactants which contain longer uninterrupted fully fluorinated perfluorinated chains.
• a fluorinated pyridinium cationic surfactant having a fluorinated terminal chain interrupted by oxygen provides desirable surface effects in a variety of applications and is particularly useful in oil field and gas field applications.
• the present invention comprises a compound of formula (I)
• Rf is R 1 (CH 2 CH 2 ) n —
• R 1 is a C 7 to C 20 perfluoroalkyl group interrupted by at least one catenary oxygen atom, each oxygen bonded to two carbon atoms,
• n is an integer of 1 to 3
• R is H, C 1 to C 5 linear or branched alkyl, or C 1 to C 5 linear or branched alkoxy.
• the present invention further comprises a method of modifying surface effects of an aqueous medium or solvent medium comprising contacting the medium with a compound of formula (I) as described above.
• surfactant means surface-active agent, which refers to a substance which, even at low concentrations, effectively lowers the surface tension of a medium containing the surfactant by selective adsorption on the interface.
• a surfactant can be a pure chemical compound or a mixture of homologues or different chemical compounds.
• drilling fluids means those liquids that are added to a well or well bore penetrating a subterranean zone containing hydrocarbon or gas prior to or during a drilling operation. Examples can include water, brine, solvent, hydrocarbons, surfactants, oils, kerosene, fracturing fluids, stimulating fluids, oil-based drill muds, clay stabilizers, treatment fluids, and mixtures thereof.
• well fluids as used herein means those liquids that occur in or are added to a well or well bore penetrating a subterranean zone containing hydrocarbon or gas. Examples can include drill fluids, water, brine, solvent, hydrocarbons, surfactants, oils, kerosene, fracturing fluids, stimulating fluids, oil-based drill muds, clay stabilizers, treatment fluids, and mixtures thereof.
• liquid treatment stream or gas treatment stream means a liquid composition or gas composition, or a combination thereof, injected into a well penetrating a subterranean zone containing hydrocarbon or gas, or into a well bore area, in the operation of extracting the hydrocarbon or gas.
• Examples can include steam, drill fluids, well fluids, stimulating fluids, water, brine, solvent, hydrocarbons, surfactants, fracturing fluids, oil-based drill muds, clay stabilizers, treatment fluids, and mixtures thereof.
• the present invention comprises a fluorinated pyridinium cationic compound of the formula (I)
• Rf is R 1 (CH 2 CH 2 ) n —
• R 1 is a C 7 to C 20 perfluoroalkyl group interrupted by at least one catenary oxygen atom, each oxygen bonded to two carbon atoms,
• n is an integer of 1 to 3
• R is H, C 1 to C 5 linear or branched alkyl, or C 1 to C 5 linear or branched alkoxy.
• the perfluoroalkyl group contains at least one oxygen atom, but can contain from 1 to 19 oxygen atoms. Each oxygen atom is catenated between two carbon atoms.
• Preferred compounds of formula (I) are those wherein n is 1 or 2. Also preferred are those wherein the perfluoroalkyl contains 1 to 15 oxygen atoms, more preferably 1 to 10 oxygen atoms, and more preferably 1 to 5 oxygen atoms, and even more preferred 1 to 3 oxygen atoms. Other preferred embodiments of formula (I) are those wherein R is hydrogen, methyl, ethyl, methoxy or ethoxy.
• the compounds of formula (I) are prepared by the reaction of a pyridine with a fluorinated iodide followed by reaction of the resulting product with an arylsulfonic acid, typically in a solvent such as alcohol.
• a fluorinated iodides such as compound C 3 F 7 O(CF 2 CF 2 ) 3 CH 2 CH 2 I
• a fluorinated ether iodide such as C 3 F 7 O(CF 2 CF 2 ) 3 I
• the resulting product of C 3 F 7 O(CF 2 CF 2 ) 3 CH 2 CH 2 I then is then contacted with pyridine under nitrogen.
• the reaction is allowed to reflux at about 80° C. for several hours, for example 20 hours.
• the product is isolating using conventional techniques.
• the above product C 3 F 7 O(CF 2 CF 2 ) 3 CH 2 CH 2 N + (C 5 H 5 )I ⁇ typically in an alcohol solvent, is then contacted under an inert gas, such as nitrogen, with heating to about 60° C. with a solution of arylsulfonic acid, such as p-toluenesulfonic acid in alcohol.
• the temperature is maintained for several hours, for example 80 hours until CH 3 I can no longer be detected by GC in the distillate, while additional alcohol is added periodically to replenish the distilled solvent.
• the alcohol is then evaporated off to yield the product as C 3 F 7 O(CF 2 CF 2 ) 3 CH 2 CH 2 N + (C 5 H 5 ) ⁇ -CH 3 C 6 H 4 SO 3 ⁇ which is characterized by NMR.
• the resulting product is then usually dissolved in methanol to obtain a 50% solution, and neutralized to a pH of 5.5 ⁇ 0.5 with 3.5% NaOH aqueous solution.
• the surfactants comprising the fluorinated pyridinium cationic compounds of formula (I) are suitable for use in many applications, such as in coatings, oil/gas fields, fire fighting, polymerization, surface treatment and protection, agriculture, textiles, carpet, hard surface treatment and protections such as in flooring, stone and tiles, photovoltaic materials, and in automotive, herbicides, printing, paper and leather industries.
• the compound of formula (I) is useful as a surfactant to affect the surface tension or other surface properties of an aqueous medium or solvent medium.
• Suitable media include water, a coating composition, latex, polymer, floor finish, fire fighting agent, ink, emulsifying agent, foaming agent, release agent, repellency agent, flow modifier, film evaporation inhibitor, wetting agent, penetrating agent, cleaner, grinding agent, electroplating agent, corrosion inhibitor, etchant solution, soldering agent, dispersion aid, microbial agent, pulping aid, rinsing aid, polishing agent, personal care composition, drying agent, antistatic agent, floor polish, or bonding agent.
• This embodiment is useful to affect the surface tension and other surface properties of the medium, or of a substrate to which the medium is applied.
• Types of surface behavior which can be altered using the compound of the present invention include, for example, wetting, penetration, spreading, leveling, flowing, emulsifying, dispersing, repelling, releasing, lubricating, etching, bonding, and stabilizing.
• the above fluorinated pyridinium cationic compounds of Formula (I) are suitable for use as surfactants to lower surface tension in a medium.
• the resulting surface tension values in a medium are less than about 25 milli-newtons per meter, preferably less than about 20 milli-newtons per meter, more preferably less than about 19 milli-newtons per meter at a concentration of the surfactant of less than about 0.5% by weight. Often such reduced surface tension is obtained at a concentration of less than about 0.2% by weight, or less than about 0.1% by weight.
• the surfactant is characterized by its efficiency in lowering the surface tension at low concentrations by selective adsorption on the interface determined by the amphiphilic nature of the surfactant.
• amphiphilic means attraction to two different kinds of media.
• Surfactants usually comprise a water-soluble hydrophilic part and a water-insoluble hydrophobic part.
• the present invention further comprises a method of modifying surface effects of an aqueous medium or solvent medium comprising contacting the medium with a compound of formula (I).
• a compound of formula (I) is lowering surface tension of a medium by contacting the medium with a fluorinated pyridinium cationic compound of formula (I).
• Examples of other surface behavior alteration include improvements in the properties of surface tension, wetting, penetration, spreading, leveling, flowing, emulsifying, stabilizing of dispersions in liquids, repellency, releasing, lubricating, etching, and bonding.
• the medium is an aqueous liquid or a solvent as detailed above.
• Examples of such applications where low surface tension is required include coating compositions and aqueous and non-aqueous cleaning products, each for glass, wood, metal, brick, concrete, cement, natural and synthetic stone, tile, synthetic flooring, laminates, paper, textile materials, linoleum and other plastics, resins, natural and synthetic rubbers, fibers and fabrics, and paints; polymers; and waxes, finishes, leveling and gloss agents for floors, furniture, shoes, inks, and automotive care.
• Wetting agent applications include wetting agents for compositions containing herbicides, fungicides, weed killers, hormone growth regulators, parasiticides, insecticides, germicides, bactericides, nematocides, microbiocides, defoliants or fertilizers, therapeutic agents, antimicrobials, fluorochemical blood substitutes, textile treatment baths, and fiber spin finishes.
• Applications in personal care products include shampoos, conditioners, creme rinses, cosmetic products for the skin (such as therapeutic or protective creams and lotions, oil and water repellent cosmetic powders, deodorants and antiperspirants), nail polish, lipstick, and toothpaste.
• Further applications include fabric care products (such as stain pretreatments and/or stain removers for clothing, carpets and upholstery), and laundry detergents.
• rinse-aids for car washes and in automatic dishwashers
• oil well treatments including drilling muds and additives to improve tertiary oil well recovery
• extreme pressure lubricants lubricating cutting oil to improve penetration times
• writing inks printing inks
• photography developer solutions emulsions for fighting forest fires
• dry chemical fire extinguishing agents emulsions for fighting forest fires
• aerosol-type fire extinguishers emulsions for fighting forest fires
• thickening agents to form gels for solidifying or encapsulating medical waste
• photoresists developers, cleaning solutions, etching compositions, developers, polishers, and resist inks in the manufacturing, processing, and handling of semiconductors and electronics.
• the surfactants of formula (I) can be incorporated into products that function as antifogging agents for glass surfaces and photography films, and as antistatic agents for magnetic tapes, phonograph records, floppy disks, disk drives, rubber compositions, PVC, polyester film, and photography films, and as surface treatments for optical elements (such as glass, plastic, or ceramics).
• Suitable media include a coating composition, latex, polymer, floor finish, fire fighting agent, water, saline solution, ink, emulsifying agent, foaming agent, release agent, repellency agent, flow modifier, film evaporation inhibitor, wetting agent, penetrating agent, cleaner, grinding agent, electroplating agent, corrosion inhibitor, etchant solution, soldering agent, dispersion aid, microbial agent, pulping aid, rinsing aid, polishing agent, personal care composition, drying agent, antistatic agent, floor polish, or bonding agent.
• the compound of the present invention is useful in gas and oil field applications.
• a hydrocarbon is either a gas or oil product which is produced or recovered from a subterranean zone.
• a well or well bore is drilled and created to penetrate such a hydrocarbon containing subterranean zone.
• the surfactant composition of the present invention is useful to modify and improve the wettability and surface conditions, such as the surface tension of the subterranean formation around the well bore, and is also useful to improve the permeability and flow rate to enhance oil well or gas well recovery and productivity.
• a compound of formula (I) acts as a surfactant or foaming agent for oil field and gas field applications.
• the compound of formula (I) is typically used in an aqueous medium selected from the group consisting of water, saline solution, KCl solution, HCl solution, hydrocarbon, halocarbon, drill fluids, well fluids, liquid treatment stream, gas treatment stream, and a mixture thereof, is used as a surfactant or foaming fluid.
• the compound of formula (I) is useful as an additive in drill fluids, well fluids, and other treatment fluids for subterranean formations, to enhance gas or oil recovery by altering surface tension, wettability, or viscosity of the fluids, oils, condensates, and muds employed or encountered in such operations.
• the surfactant can be used for foaming porous rock or soil medium of a subterranean formation, or for other known well or well bore treatments.
• the present invention provides a surfactant or foaming fluid which comprises the fluorinated pyridinium cationic compounds of formula (I) and a medium, wherein the fluorinated pyridinium cationic compound of formula (I) is present at a concentration range of from about 0.001% to about 50% by weight, preferably a range of from about 0.01% to about 30% by weight, and more preferably a range of from about 0.05% to about 20% by weight.
• the present invention further comprises a method of foaming a well fluid to be introduced into a well bore penetrating a hydrocarbon-containing subterranean zone comprising the steps of 1) providing a compound of formula (I) of the present invention, and 2) contacting the compound with compressed air or an inert gas to generate a foamed fluid.
• the present invention further comprises a method of lowering the surface tension within a subterranean formation containing hydrocarbons comprising adding a compound of formula (I) as described above to a medium which is a carrier contacted with the subterranean formation.
• One method of contacting is injection of the carrier or medium into the subterranean formation, for example by using a downhole, well, or well bore.
• the compound of formula (I) is added to a carrier or medium such as a fluid or gas which will be in contact with the subterranean formation during operations to remove oil or gas from the formation.
• Examples include drill fluids, well fluids, stimulation fluids, liquid treatment streams, gas treatment streams, fractionating fluids, clay stabilizers, or other liquids or gases employed when extracting the hydrocarbons from the formation.
• the compounds of the present invention can be used in one or more of a pretreatment stage of injection of a pre-flush of various liquids, or in matrix or stimulation activities; in the main stage in various carrier fluids, or in a soaking of the formation for a specific time period; or in a post treatment stage for displacement operation to achieve better placement of the fluids containing the surfactant composition.
• the compound of the present invention is used in the form of a liquid, emulsion, dispersion, or foaming agent.
• Foaming is a desirable property of the surfactants of the present invention which are used as additives to drill fluids, well fluids, and other fluids in oil and/or gas field applications for enhanced production and recovery.
• the aqueous or solvent based drilling fluids, well fluids, liquid or gas treatment streams, or other carrier compositions which contain the compound of the present invention foam during drilling or well treatment processes, and therefore provide advantages for enhanced production and recovery. Examples of such advantages from the surfactant and foaming properties include aiding in the removal of fines from the well to around the drill-bit and wellbore treatment area, and adjusting the permeability and wettability properties where the fluids contact around the drill-bit and wellbore treatment area.
• the addition of the surfactant of the present invention boosts the foaming properties of the oil/gas well drilling fluids and treatment fluids. If these fines are not efficiently removed, they can result in damage to the drill-bit head, costing time and money to replace or repair.
• the surfactant of the present invention is useful to reduce the viscosity of the hydrocarbon to permit easier extraction.
• Another advantage of contacting a subterranean formation containing hydrocarbons with the fluorinated pyridinium cationic surfactant of the present invention as defined above, is providing a method for stimulating production of hydrocarbons during operations to extract hydrocarbons from a subterranean formation.
• the fluorosurfactant compounds of the present invention are useful as stimulation fluid additives for stimulation activities, such as hydraulic fracturing and acidizing.
• the stable foams of the present invention improve the wetting of the stimulation fluid on the formation surface (rock) to allow for deeper penetration and better stimulation of the well bore region.
• the low surface tension of these additives permit the stimulation fluids to be more efficiently and easily recovered from downhole. As a result, the well will be able to more effectively produce gas and oil.
• the surfactant compounds of the present invention is further useful as an aid to prevent and remedy water blocks or condensate blocks in wells and well bore areas. It is known that water can accumulate near the well bore of an oil or gas well and decrease productivity by decreasing the relative permeability of the oil or gas, which is called water block. In addition liquid hydrocarbons can also accumulate and cause a decrease in productivity in gas wells near or far from the well bore region known as condensate block.
• the compounds of the present invention can be used to help in removal of at least a portion of such accumulations of liquids in a water block or condensate block, or for reducing or preventing the formation of the accumulation of liquids in such blocks.
• the fluorinated pyridinium cationic surfactant of the present invention is useful as a surfactant additive in drill fluids, well fluids and treatment fluids for subterranean formation to alter the wettability and permeability by its surface active properties.
• Such surfactants for example, are used within the porous rock medium of subterranean formation and can result in pressure changes or as foams can block the gas drain paths and result in the oil/gas recovery increases.
• the compound of the present invention provides an advantage in that desirable surface effects are obtained using a surfactant containing a fully fluorinated perfluoroalkyl chain interrupted by oxygen.
• compositions of the present invention are advantageous over surfactants containing longer chain perfluoroalkyls or mixtures of homologues of perfluoroalkyls, each no interrupted by oxygen, while providing comparable or superior performance.
• Tetrafluoro ethylene 180 g was introduced to an autoclave charged with C 3 F 7 OCF 2 CF 2 I (600 g), and the reactor was heated at 230° C. for 2 h. The same reaction was repeated twice. The products were combined and isolated by vacuum distillation to provide C 3 F 7 OCF 2 CF 2 CF 2 CF 2 CF 2 CF 2 I (234 g, 18%) b.p. 89 ⁇ 94° C. at 60 mmHg (79.98 ⁇ 10 2 Pascals) based on the recovery of starting material. The product was characterized by NMR below:
• a stock solution was prepared for the highest concentration of fluorosurfactant to be analyzed.
• the concentration of the solutions was by percent active ingredient, weight percent, or fluorine content.
• This stock solution was prepared in deionized water, 2% KCl water, or 15% HCl water depending on the desired oilfield application for which the surface tension was being measured. The stock solution was stirred overnight (for approximately 12 hours) to ensure complete mixing.
• the 2% KCl solution was similar to the salinity of the fracture fluids that are used to hydraulically fracture a well.
• the 15% HCl solution emulated the acidizing stimulation treatment fluid that is used to help dissolve the formation rock in wells.
• the surface tension was measured using a Kruess Tensiometer, K11 Version 2.501 in accordance with instructions with the equipment. The Wilhelmy Plate method was used. A vertical plate of known perimeter was attached to a balance, and the force due to wetting was measured. 10 replicates were tested of each dilution, and the following machine settings were used:
• the test procedure used to evaluate the foaming of fluorosurfactants for oilfield applications was a nitrogen bubble foaming test.
• stock solutions of the testing base solutions were made. These solutions were deionized water, 2% KCl, and 15% HCl.
• Samples of 20 mL of the fluorosurfactant at 0.1% active ingredient in the desired base testing solution were prepared and stirred overnight to ensure complete mixing.
• the sample solution was then added to a 100 mL graduated cylinder (glass). Nitrogen was then bubbled through the solution to produce foam at a rate that filled the cylinder in 20-30 seconds. A fritted glass tube was used to bubble the nitrogen through the solution. When the foam reached the top of the cylinder, the nitrogen was turned off and a timer was started.
• the heights of the foam and liquid in mL were measured after 30 seconds, 5 minutes, 10 minutes, and 15 minutes. A difference of up to 10 mL in foam height is within the variation of this method. Observations of the quality and persistency of the foam were also recorded. At least three repetitions were conducted for each sample test.
• This nitrogen bubbling foam test was used as an indicator of the amount of foam that a sample produced and the persistency of that foam. Higher foam heights which lasted for a longer time indicated superior performance.
• Example 1 The process of Example 1 was employed with the formula C 8 F 17 CH 2 CH 2 I.
• the resulting product C 8 F 17 CH 2 CH 2 N + (C 5 H 5 ) ⁇ -CH 3 C 6 H 4 SO 3 ⁇ was tested for surface tension and foaming using test Methods I and 2. The results are in Tables 1 to 6.
• Example 1 The process of Example 1 was employed using the formula C 6 F 17 CH 2 CH 2 I as a starting material.
• the resulting product C 6 F 17 CH 2 CH 2 N + (C 5 H 5 ) ⁇ -CH 3 C 6 H 4 SO 3 ⁇ was tested for surface tension and foaming using Test Methods 1 and 2. Results are in Tables 1 to 6.
• the normal surface tension of deionized water, 2% KCl aqueous solution and 15% HCl aqueous solution is about 72 dyne/cm (shown in Tables 1 to 3 as 0.000%).
• the fluorosurfactant of the present invention was added at a specified rate, the surface tension of each aqueous solution was reduced significantly. Better performance was obtained at higher levels. According to the results from the test, superior surface tension reduction was seen from the Example 1 of the present invention versus the Comparative Examples A and B.
• Example 1 of the present invention showed excellent initial performance and generally comparable performance over time versus the Comparative Example A.
• Example 1 showed superior performance to Comparative Example B which did not sustain foam over time.

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• 2009
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