Fatty acid reaction product of dextrin or dextran formulated with a surfactant

Abstract

A composition comprising a neutral surfactant or a reaction product thereof and a reaction product of a sugar polymer and a fatty acid can be obtained in the presence of water and a hydroxide base (optional in the presence of a neutral surfactant), and the sugar polymer comprises dextran, dextrin compounds, or a combination thereof. The reaction product of the sugar polymer and the fatty acid may be present at a concentration effective for lowering the surface tension of the neutral surfactant. Among other factors, depending on the fatty acid retention, the composition may promote emulsification or de-emulsification. Additionally, the composition may promote foam formation under appropriate conditions. A treatment fluid comprising a composition containing a foaming treatment fluid may be introduced into a subsurface formation to perform a treatment operation in which fluid emulsification or de-emulsification may occur. The reaction product may be included in soaps and other personal care products.

Description

Technology Field

[0001] The present invention relates to a fatty acid reaction product of dextrin or dextran formulated with a surfactant. Background Technology

[0002] Amphiphilic compounds possessing both hydrophobic and hydrophilic regions within their molecular structure are generally referred to as "surfactants" or "surfactant compounds." Due to their molecular structure, surfactants tend to lower surface tension at the interface between two components. Surfactants can be found in a wide range of consumer and industrial products, including, for example, soaps, detergents, cosmetics, pharmaceuticals, and dispersants. Surfactants are also commonly used in the oil and gas industry. Among their functions in these and other applications, surfactants can promote the solubility of poorly soluble solids, increase foaming, facilitate emulsification or de-emulsification, and / or, in certain cases, reduce viscosity. Poor biodegradability, including slow biodegradation in liquid environments, and / or poor biocompatibility of some common synthetic surfactants can affect consumer and industrial products and processes that contain these surfactants.

[0003] The recovery of hydrocarbon resources, such as oil and gas, from subsurface formations is often carried out in connection with the introduction of one or more subsurface treatment chemicals into the downhole. As used herein, the terms “treat,” “treat,” “treating,” and their grammatical equivalents refer to any compound, fluid, or combination thereof introduced into a subsurface formation with the aim of achieving a desired function and / or for a desired purpose. Appropriate treatment chemicals may be selected based on specific conditions present or expected to be present in the downhole. Environmental and regulatory issues may also dictate the appropriate treatment chemicals available for use in a specific region. Surfactants are frequently used treatment chemicals in oil fields and can perform various functions.

[0004] Oils and other hydrocarbon resources can often exist in emulsified form in underground formations. De-emulsifiers may be used to release emulsified oils and other hydrocarbon resources to facilitate production and / or post-production processing. It may also be desirable in many cases to prevent the emulsion from forming downholes.

[0005] In other cases, it may be desirable to introduce an emulsifying fluid into the subsurface formation. Alternatively, intended treatment results can be facilitated by using a fluid that advances or promotes emulsifying downholes, inverts existing emulsion downholes, or alters the wetting of surface downholes. In non-limiting examples, the emulsifying fluid may have sufficient viscosity to transport particulates into or from the well, such as propane particulates, drill cuttings, or crosslinking agents. The emulsifying fluid can likewise facilitate the release of hydrocarbon resources bound to the matrix of the subsurface formation by altering surface wetting properties. Microemulsion fluids may be advantageous in many cases due to their optical transparency and ease of handling. Microemulsion fluids can likewise alter surface wetting properties downward or draw hydrocarbon resources into the fluid during production.

[0006] In the aforementioned applications, various types of surfactants may be used in the oil and gas industry to stabilize emulsions or promote the de-emulsification of fluids. In many cases, surfactants capable of promoting emulsification or de-emulsification have completely different chemical structures, and common classes of surfactant compounds cannot be easily adapted to the specific conditions that may exist in downholes. Some common surfactants are expensive, have low water solubility, and may be subject to environmental and / or other government regulations. Additionally, some emulsifiers or de-emulsifiers have high surface tension and interfacial tension values ​​at critical micelle concentrations and may not be easily pumped. These issues can present relevant barriers when formulating consumer and industrial products containing surfactants.

[0007] In addition to being frequently used to promote emulsification or de-emulsification in various industrial and consumer products, surfactants are commonly used to promote foam formation in aqueous fluids. The foaming properties of soaps, detergents, shampoos, and similar consumer products are familiar examples. Foaming fluids are also frequently used in oil and gas production. As used herein, the term "foam" refers to a stabilized dispersion of a large amount of gas in the form of bubbles of various sizes within a relatively small volume of liquid. The term "foam quality" refers to the percentage of gas in the foam volume and can be calculated by dividing the quantity (total foam volume - liquid volume) by the total foam volume. Ionic surfactants are one of the most commonly used types of surfactants for foaming promotion. However, ionic surfactants can lead to incompatibility with other types of substances, such as divalent ions, and some may be subject to regulatory restrictions, particularly when used in large quantities. Furthermore, ionic surfactants can sometimes provide inconsistent foaming performance at high temperatures. Brief explanation of the drawing

[0008] The following drawings are included to illustrate specific aspects of the invention and should not be construed as exclusive embodiments. Substantial modifications, changes, combinations, and equivalents are possible for the subject matter disclosed without departing from the scope of the disclosure. Figures 1a to 1d each show plots of the emulsification rate as a function of time for terero oil emulsified with sample AD. Figures 2a to 2d each show plots of the emulsification rate as a function of time for Wolfcamp A oil emulsified with sample AD. Figures 3a to 3d each show plots of surface tension as a function of concentration for sample AD. Figures 4a through 4d show plots of emulsification rates as a function of time for East Texas Hutcheson #2 oil emulsified with samples E1-E4, F1-F4, G1-G4, and H1-H4. Figure 5 shows a plot of the water emulsification rate at 60 minutes for samples E1-E4, F1-F4, G1-G4 and H1-H4. Figure 6 shows a bar graph of the Hart-DeGeorge foam test performance of the experimental soap formulation and the comparative soap formulation. The experimental soap formulation contains the reaction product of maltodextrin and lauric acid formed in the presence of cocamide diethanolamine, and the comparative soap formulation contains an equal amount of sodium lauryl sulfate, an anionic surfactant commonly used in soaps and personal care products. Specific details for implementing the invention

[0009] The present invention generally relates to surfactant technology, more specifically to compositions having low surface tension capable of emulsifying, de-emulsifying, viscosizing, or foaming a fluid. In some emulsion applications, the composition may form a microemulsion. Various industrial and consumer products comprising foaming or foaming compositions may be formed from the composition.

[0010] As discussed above, emulsion management can be desirable when producing hydrocarbon resources from subsurface formations. In some cases, the presence of an emulsion may be appropriate, for example, to facilitate the transport of solids to or from subsurface formations or to alter the wetting characteristics of the surface within the well. In other cases, it may be advantageous to break up the emulsion to allow for the generation of hydrocarbon resources. Various types of surfactants can be used for these purposes and are found in a wide range of industrial and consumer products. Often, surfactants with significantly different structures are used to facilitate emulsification and de-emulsification. Surface tension (interfacial tension) and interfacial tension values ​​are often high in some types of surfactants, and some may be subject to regulatory restrictions. Furthermore, some types of surfactants, particularly anionic surfactants, can have harmful interactions with components that may be present in the fluid, such as salts.

[0011] Surfactants can also be used to promote the foaming of fluids. In addition to the familiar presence of foam in household and personal care products such as soaps and detergents, foam is frequently used in oil and gas production as a special processing fluid. When used to promote foaming in these and other applications, surfactants can exhibit the same types of problems that occur when promoting emulsification or de-emulsification. Furthermore, ionic surfactants can cause inconsistent foaming performance in certain cases, particularly at higher temperatures and in the presence of specific metal cations.

[0012] The present disclosure provides a biopolymer-based compound that can be produced with tunable adducts to promote emulsification or de-emulsification (e.g., to adjust the hydrophilic-lipophilic balance (HLB)) depending on how the biopolymer is functionalized, including when combined with a suitable neutral surfactant. That is, the present disclosure provides a saccharide polymer comprising a dextran or dextrin compound that reacts with a fatty acid preferably under alkaline conditions and optionally in the presence of a neutral surfactant to provide a reaction product having surfactant-modifying properties and unexpectedly low surface tension values ​​in the presence of a suitable surfactant. Without being limited by theory, the reaction product may comprise at least one fatty ester of the dextran or dextrin compound, which interacts synergistically with the neutral surfactant to provide low surface tension values. Although the components forming the reaction product individually tend to increase surface tension values, when combined together in the reaction product, they can surprisingly lower the surface tension of cocamide diethanolamine (CocoDEA) and similar neutral surfactants, which is likely possible after the additional reaction of its primary alcohol functional group. Similar neutral surfactants capable of acting in a similar manner may include, but are not limited to, other fatty acid amide alkanolamines, such as those formed from palmitic acid and ethanolamine or diethanolamine. Dextrin compounds also have secondary alcohol functional groups as well as primary alcohol functional groups capable of reacting with fatty acids to form the reaction product according to the present invention. The reaction product may be advantageous due to its biological origin, low cost, and ability to provide low surface tension values ​​when present with neutral surfactants. Furthermore, the chain length of the fatty acid component of the reaction product can help to adjust the properties obtained therefrom, including determining whether emulsifying or de-emulsifying performance results in a specific environment.The reaction products of maltodextrin represent a particularly useful class of dextrin-based reaction products.

[0013] Additionally, a reaction product having a sufficiently high hydrophilic-lipophilic balance (HLB) can promote foaming of the formulation, including when combined with one or more suitable surfactants. A combination of a neutral surfactant and the reaction product of the present invention can promote the foaming preparation of an aqueous fluid and can provide a more stable foam than a significant amount of ionic surfactant, including cationic, anionic, or zwitterionic surfactants. A zwitterionic surfactant can optionally be combined with the reaction product to improve foaming performance compared to the reaction product and the neutral surfactant alone. For example, when combined with CocoDEA, other fatty acid amide alkanolamines, or their reaction products, the reaction product formed from maltodextrin and lauric acid can produce a less dense and more stable foam than substantially the same amount of sodium lauryl sulfate (sodium dodecyl sulfate), an anionic surfactant commonly used in personal care products such as soaps and shampoos. Given the biomolecular properties of the reaction products, foaming or foaming formulations comprising one or more reaction products of the present invention may represent a more environmentally friendly approach for formulating soaps and other personal care products.

[0014] In addition to providing foaming or foaming formulations based on neutral surfactant technology, the reaction product of the present disclosure can completely or partially replace government-regulated, expensive surfactants and / or surfactants in various industrial or consumer products. For example, the reaction product of the present invention can effectively replace ethoxylated alcohol neutral surfactants. The reduction in surface tension provided by the reaction product of the present invention in combination with a neutral surfactant can be advantageous when replacing less desirable surfactants.

[0015] Maltodextrin represents a sugar polymer advantageous for use herein in terms of low cost, environmentally friendly characteristics, and relative ease of chemically reacting with fatty acids having a range of chain lengths. Depending on the fatty acid reacting with the maltodextrin, the hydrophobic-lipophilic balance (HLB) of the reaction product may range from about 5 to about 20 or higher, and the HLB value can be calculated using the molecular contributions known herein. Thus, the maltodextrin reaction product can be effective in forming emulsions in substantially aqueous fluids or substantially oily fluids, and is selected based on specific conditions and the type of hydrocarbon resource when a specific fatty acid is present in the downhole for reaction with the maltodextrin or when necessary when formulating a given product. Likewise, such maltodextrin reaction products can promote foaming if the HLB is sufficiently large. In addition to changes in properties due to fatty acid size, maltodextrin is available in various oligomer sizes (e.g., 3–20 glucose monomers, or up to about 25 glucose monomers), which can allow for further adjustment of foaming properties or emulsifiers to be realized. As such, maltodextrin reaction products can offer various benefits and broad applicability for downhole use and other applications where surfactants are commonly used, such as soaps and other personal care products. Dextran reaction products can provide similar benefits and characteristics to maltodextrin reaction products, including the ability to generate low surface tension values, and are formed and used under similar conditions.

[0016] A dextrin compound suitable for use in the present invention may comprise 2 to about 20 glucose monomers, or up to about 25 glucose monomers, linked together by α(1,4) glycosidic bonds. At least some of the glucose monomers are C4-C 30 fatty acids or C4-C 20A reaction product can be formed upon contact with a fatty acid salt, such as a salt of a fatty acid, under suitable conditions. Without being limited by theory, at least a portion of the glucose monomer may react to form a fatty ester of the dextrin compound in some embodiments and may optionally exist in combination with an unreacted fatty acid salt in the aqueous phase. When formed, the ester reaction product may be formed at any hydroxyl group of the dextrin compound comprising any combination of primary and / or secondary hydroxyl groups. The hydroxyl group of a neutral surfactant may react under similar conditions.

[0017] Dextran is a saccharide polymer characterized primarily by α(1,6) glycosidic bonds between adjacent glucose monomers, along with a limited number of glucose side chains connected to the main polymer backbone via α(1,3) glycosidic bonds. α(1,3) glycosidic bonds can introduce cross-linking between adjacent saccharide polymer chains. Depending on the biological source, the degree of branching and molecular weight of dextran can vary considerably, and any of these may be used in the present disclosure. At least some of the glucose monomers in dextran are C4-C 30 fatty acids or C4-C 20 A reaction product can be formed upon contact with a fatty acid salt, such as a salt of a fatty acid, under suitable conditions. Without being limited by theory, at least a portion of the glucose monomer may react in some embodiments to form a fatty ester of dextran, optionally present with an unreacted fatty acid salt in the aqueous phase. When formed, the ester reaction product may be formed at any hydroxyl group of dextran.

[0018] In some embodiments, the reaction product of the present disclosure may comprise a dextrin compound having 3 to about 20 glucose monomers covalently bonded by α(1,4) glycosidic bonds, or even about 25 or fewer glucose monomers. Formula 1 below represents the general structure of a dextrin compound having only α(1,4) glycosidic bonds between adjacent glucose monomers, wherein the variable 'a' is a positive integer in the range of 1 to about 18, thereby providing a dextrin backbone having 3 to about 20 glucose monomers. For a dextrin compound containing up to 25 glucose monomers, the variable 'a' may be in the range of 1 to about 23. The terminal glucose units are represented in a closed form, but may also exist in the corresponding reducing sugar form as follows.

[0019]

[0020] Other dextrin compounds may contain only α(1,6) glycosidic bonds or a mixture of α(1,4) and α(1,6) glycosidic bonds, and such dextrin compounds may be suitable for use in forming reaction products. Particularly suitable dextrins may have a molecular weight (e.g., Mn) in the range of about 1200 to about 1400 or about 1100 to about 1500.

[0021] In some or other embodiments, the reaction product may comprise dextran obtained from any suitable source. The structure of the dextran is shown in Formula 2 below, and α(1,3) glycosidic bonds are not shown for clarity. Where these occur, α(1,3) glycosidic bonds may add terminal glucose monomers as side chains to an α(1,6)-linked saccharide polymer backbone, form crosslinks between adjacent α(1,6)-linked saccharide polymer backbones, interfere with an α(1,6)-linked saccharide polymer backbone with α(1,3) glycosidic bonds, or a combination thereof. Depending on the source, up to about 5% of the glucose monomers may be linked by α(1,3) glycosidic bonds. Linking by α(1,3) glycosidic bonds may occur in any of the glucose monomers. The numbering of the single glucose monomers is as shown in Chemical Formula 3 below.

[0022]

[0023] Suitable dextrans may have a molecular weight of about 1200, or about 1400, or about 5000 to about 50,000,000, or about 100,000 to about 20,000,000. As such, variable 'b' may range from about 30 to about 300,000 depending on the specific dextran selected. Particularly suitable dextrans may have a molecular weight (e.g., Mn) in the range of about 1200 to about 1400, or about 1100 to about 1500, or about 100,000 to about 1 million, or about 2 million to about 5 million. Another suitable dextran may have a molecular weight of about 500,000 and an activity level of about 9%.

[0024]

[0025] According to some embodiments of the present invention, the saccharide polymer may include maltodextrin. Maltodextrin can be characterized by its DE (dextrose equivalent) value. The dextrose equivalent is a measure of the amount of reducing sugars (e.g., glucose monomers) present in the saccharide polymer, particularly in dextrin, and is expressed as a percentage of dextrose. The defined dextrose equivalent of functionally non-reducing starch is 0, whereas the dextrose equivalent of dextrose itself is 100. The dextrose equivalent can be calculated by dividing the molecular weight of glucose by Mn and multiplying the result by 100. Higher dextrose equivalent values ​​are characterized by a smaller number of covalently bonded glucose monomers (a higher relative proportion of terminal reducing sugars due to shorter polymer backbone lengths). Maltodextrin suitable for forming a reaction product with one or more fatty acids according to the disclosure of the present invention may have a dextrose equivalent in the range of 3 to about 25 or 3 to about 20. In a more specific embodiment, the dextrose equivalent value of the maltodextrin may be in the range of about 4.5 to about 7.0, or about 7.0 to about 10.0, or about 9.0 to about 12.0.

[0026] Maltodextrin suitable for forming the reaction product may be obtained from starch, specifically from the hydrolysis or thermal decomposition of the amylose component of starch, according to some embodiments. Maltodextrin of Formula 1 may be formed, for example, by the hydrolysis or thermal decomposition of amylose. An alternative suitable dextrin may be obtained from the hydrolysis or thermal decomposition of the amylopectin component of starch, in which case, if the dextrin is obtained through the hydrolysis of the amylopectin side chain, the dextrin may contain α(1,6) glycosidic bonds. Starch capable of subsequently producing dextrin may be obtained from any starch source.

[0027] Accordingly, the reaction product of the present invention may comprise a first reaction component comprising a sugar polymer selected from dextran, dextrin compounds, or any combination thereof, and a second reaction component comprising one or more fatty acids. The reaction product may be obtained in the presence of water and a hydroxide base. Suitable hydroxide bases may include alkali metal hydroxides, such as, for example, sodium hydroxide, potassium hydroxide, or combinations thereof. There may be a stoichiometric excess or stoichiometric deficiency of the hydroxide base for one or more fatty acids. Optionally, the reaction product may be formed in the presence of a neutral surfactant.

[0028] The molar ratio of fatty acids to glucose monomers in the reaction product is mol 지방산 :mole 글루코스 About 0.05 or more or mol based on the monomer 지방산 :mole 글루코스 About 0.08 or more or mol based on the monomer 지방산 :mole 글루코스 About 0.1 or more or molar based on monomer 지방산 :mole 글루코스 Approximately 0.2 or more or molar based on monomers 지방산 :mole 글루코스 Approximately 0.3 moles or more based on monomers or moles 지방산 :mole 글루코스 Approximately 0.4 or more based on monomer, or molar 지방산 :mole 글루코스 Approximately 0.5 or more or mol based on monomers 지방산 :mole 글루코스 Approximately 0.6 or more or mol based on monomers 지방산 :mole 글루코스 Approximately 0.7 or more based on monomers or molar 지방산 :mole 글루코스 About 0.8 or more or mol based on the monomer 지방산 :mole 글루코스Based on the monomer, it may be about 0.9 or greater. Based on the glucose monomer, the maximum ratio of fatty acids to dextrin or dextran in the reaction product may be about 1.0 in most cases. The above ratio may represent the molar ratio of fatty acids reacting with the dextran or dextrin compound. In some cases, one or more hydroxyl groups per glucose monomer may react. At least a portion of the glucose monomer may remain in an unfunctionalized state. If unreacted carboxylic acid is present, it may remain in the reaction product as a free carboxylate salt of a hydroxide base. Thus, the reaction product of the present invention may optionally comprise one or more dextrin fatty esters and / or one or more dextran fatty esters in combination with fatty acid carboxylates (e.g., alkali metal carboxylates) and hydroxide bases (e.g., alkali metal hydroxide bases). The hydroxide base may be present in a molar amount sufficient to react with substantially all fatty acids present to form alkali metal carboxylates. Hydroxide bases can be neutralized with acid or removed by washing, and the reaction products can retain the ability to provide low surface tension.

[0029] The composition of the present invention may include a neutral surfactant and / or a zwitterionic surfactant together with the reaction product. Surprisingly, the reaction product of the present invention can promote a reduction in the surface tension of the neutral surfactant or the zwitterionic surfactant. That is, the reaction product may be present at a concentration effective in lowering surface tension compared to that produced by the neutral surfactant or the zwitterionic surfactant alone at substantially similar concentrations. The neutral surfactant may be useful because its surface tension value is already low. When combined with a sugar polymer during the formation of the reaction product, the alcohol group on the neutral surfactant may also form a reaction product such as a fatty acid.

[0030] Suitable neutral surfactants capable of lowering surface tension in combination with reaction products include cocoamide-based surfactants such as cocamide diethanolamine, cocamide monoethanolamine, cocamide monoisopropanolamine, and cocamide diisopropanolamine. Cocamide diethanolamine (CocoDEA) may be a suitable neutral surfactant for use in the present invention. Other suitable neutral surfactants include additional fatty acid amide alkanolamines such as palmitate amide diethanolamine or monoethanolamine. In the compositions of the present invention, such neutral surfactants may be present at a concentration of about 20% by weight or less, or about 10% by weight or less, or about 5% by weight or less, for example, about 1% by weight to about 10% by weight, or about 3% by weight to about 8% by weight.

[0031] Betaine surfactants are a type of zwitterionic surfactant. Since the net charge of zwitterionic surfactants is zero, they may also be considered to constitute neutral surfactants in this specification. Zwitterionic surfactants, such as cocamidopropyl betaine, may also be present in the compositions of the present invention in some cases alone or together with neutral surfactants, particularly when producing effervescent formulations containing reaction products. Zwitterionic surfactants can likewise lower surface tension when combined with reaction products.

[0032] Once formed, the pH of the reaction product disclosed herein may be in the range of about 1 to about 14, e.g., about 1 to about 5, or about 5 to about 7, or about 7 to about 9, or about 9 to about 14. In some cases, lower surface tension values ​​may be realized as the pH decreases. Reduced surface tension may also be realized in the presence of dissolved salts such as potassium chloride.

[0033] The reaction product of the present invention, which may comprise formed by the reaction of one or more fatty acids with a dextrin compound and / or dextran, may be prepared by a method comprising the steps of: heating a sugar polymer comprising dextran, a dextrin compound (e.g., comprising 3 to about 20 glucose monomers linked together with α(1,4) glycosidic bonds, or even about 25 or fewer glucose monomers), or any combination thereof, a fatty acid, and a hydroxide base in water; obtaining a reaction product of the sugar polymer and the fatty acid in the aqueous phase; and combining the reaction product with a neutral surfactant or optionally a reaction product thereof, such as a cocamide-based surfactant or a zwitterionic surfactant, in the aqueous phase. The reaction product may be combined with the neutral surfactant or the zwitterionic surfactant in an amount effective for reducing surface tension compared to the surfactant alone at the same concentration. Any reaction product of a dextran or dextrin compound may constitute a suitable sugar polymer for forming a composition having low surface tension. Heating may be performed at a temperature of about 100°C or less, such as about 50°C to about 80°C, or about 60°C to about 70°C, or about 50°C to about 60°C.

[0034] The reaction product may be formed in the presence of a neutral surfactant or a zwitterionic surfactant, or the neutral surfactant or zwitterionic surfactant may be combined after the formation of the reaction product is complete. For example, the reaction product may be redissolved in an aqueous solution containing a neutral surfactant or a zwitterionic surfactant after precipitation. In some embodiments, the reaction product may be formed in the presence of a neutral surfactant or combined with a neutral surfactant due to the low surface tension value that can be obtained. If present during the formation of the reaction product, a reaction product of a neutral surfactant having a hydroxyl group may be formed.

[0035] When a neutral surfactant is used, the surface tension value of the composition may be about 40 dynes / cm or less, or about 38 dynes / cm or less, or about 36 dynes / cm or less, or about 34 dynes / cm or less, or about 32 dynes / cm or less, or about 30 dynes / cm or less, or about 28 dynes / cm or less. Surface tension may be largely influenced by the amount of neutral surfactant present, and the selected amount of neutral surfactant is chosen to provide a desired degree of surfactant applicable to a given use. In the selected amount of neutral surfactant, the reaction product may be present in an amount sufficient to lower the surface tension compared to the surface tension otherwise obtained for the surfactant alone at substantially the same concentration. The corresponding surface tension value for the composition may be about 10 dynes / cm or less.

[0036] In forming the reaction product of the present disclosure, the method of the present disclosure may comprise the steps of combining a fatty acid, a hydroxide base, and a neutral surfactant and / or a zwitterionic surfactant in water to form a mixture, and heating the mixture until the fatty acid is dissolved and a homogeneous mixture is formed. Subsequently, the method may comprise combining a sugar polymer with the homogeneous mixture and continuing to heat until a reaction product is formed to a sufficient degree. The resulting aqueous mixture may be used directly in further applications by optionally concentrating or diluting and then further combining it with additional components for a specific formulation. Formulations and products in which the aqueous mixture of the reaction product may be used are discussed below. In some cases, the aqueous mixture may at least partially replace another surfactant in a specific formulation, such as a charged surfactant. In other cases, the aqueous mixture may at least partially replace an ethoxylated alcohol surfactant in a formulation.

[0037] A fatty acid suitable for use in forming the reaction product of the present invention may be selected to provide a reaction product having an HLB value range, for example, about 5 to about 20. The fatty acid is C4 to about C 30 , or about C4 to about C 20 , or about C6 to about C 18 , or about C8 to about C 24 The size may be within a range. Suitable fatty acids for forming the reaction product according to the disclosure of the present invention may be straight-chain or branched, and saturated or unsaturated. Exemplary fatty acids suitable for forming the reaction product of the present invention are, for example, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pellavonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melisic acid, crotonic acid, cervonic acid, linoleic acid, linolerid acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, saphenic acid, vacsenic acid, folic acid, oleic acid, pinolenic acid, stearidonic acid, eleostearic acid, elaidic acid, elaidic acid, It includes gondoic acid, gadolic acid, erucic acid, eicosenic acid, eicosadienkoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, nervonic acid, mitic acid, adrenergic acid, etc. and combinations thereof. Lauric acid or a combination of lauric acid and myristic acid may be an example of a suitable acid. Any branched variant of the fatty acid may also be suitably used to form the reaction product of the present invention.

[0038] The method of the present disclosure may further comprise the step of inducing foam formation in an aqueous phase after obtaining the reaction product, optionally further mixing the reaction product with water and / or adding additional components. Inducing foam formation in the aqueous phase may occur by stirring or blending in the presence of gas, gas foaming through the aqueous phase, or any combination thereof, by stirring the aqueous phase in the presence of gas. Neutral surfactants and / or zwitterionic surfactants may be present with the reaction product during foam formation.

[0039] Gases suitable for forming foams in the presence of reaction products are not considered to be particularly limited. Gases suitable for foam formation may include, but are not limited to, air, nitrogen, carbon dioxide, helium, natural gas, or any combination thereof. In some cases, aerosol propellants may also be used.

[0040] A foam formed according to the disclosure of the present invention may have a foam quality of about 10% or more, or about 20% or more, or about 30% or more, or about 40% or more, or about 50% or more, or about 60% or more, or about 70% or more, or about 80% or more, or about 90% or more. The upper limit of the foam quality may be about 99%, or about 95%, or about 90%, or about 80%, or about 70%, or about 60% or about 50%.

[0041] The foaming or foaming formulation of the present invention may comprise an aqueous phase comprising an aqueous carrier fluid, which is described in more detail below. The foaming formulation (foam) is a composition in which a gas has already been introduced to form foamed bubbles. That is, the foaming formulation may comprise a gas and an aqueous fluid comprising the composition described herein mixed with the gas as a plurality of bubbles. In contrast, the foaming formulation is a composition suitable for forming a foam once a gas is introduced, but does not yet form foam bubbles.

[0042] In addition to the reaction products of the present disclosure, the foaming or foaming formulation may further comprise one or more additional surfactants that may be cationic, anionic, zwitterionic, neutral, or any combination thereof. The foaming or foaming formulation may also contain additional ingredients found in soaps and other personal care products, examples of which will be familiar to those skilled in the art. Further disclosures regarding industrial and consumer products comprising personal care products and foaming variants thereof in which the compositions described herein may be present are discussed in more detail below.

[0043] The reaction product may be provided, supplied, mixed, or stored in solid or liquid form. The liquid form may be placed in a suitable fluid phase, such as an aqueous phase, which may be emulsified or non-emulsified depending on the specific formulation and intended use. Additionally, the aqueous phase may be foamed in some cases. Unless otherwise indicated, the terms “fluid” and “fluid phase” as used herein refer to both liquids and gels, including solutions, emulsions, and suspensions of the reaction product containing foam. A composition comprising the reaction product of the present invention may include an aqueous carrier fluid. Suitable aqueous carrier fluids may include, for example, fresh water, acidified water, seawater, brine (i.e., saturated salt solution), or aqueous salt solution (i.e., unsaturated salt solution). Water-miscible organic cosolvents, such as ethanol or ethylene glycol, may be present with the aqueous carrier fluid in some embodiments. Suitable aqueous carrier fluids may be present during the formation of the reaction product, or the aqueous carrier fluids may be introduced into the reaction product after its formation.

[0044] Underground processing work

[0045] The reaction product of the present invention, comprising that formed from maltodextrin, other dextrin compounds, or dextran, may be formulated into a subsurface treatment fluid. The treatment fluid may be used in various subsurface treatment operations to promote or facilitate desired results within subsurface formations. As used herein, the term “treatment fluid” means any fluid used in a subsurface treatment operation in connection with achieving a desired function and / or desired purpose. Unless otherwise specified, the use of the term “treatment fluid” does not imply a specific action by the treatment fluid or its components. Exemplary treatment operations that may be facilitated by the use of the reaction product of the present disclosure include, but are not limited to, drilling operations, stimulating operations, production operations, purification operations, sand control operations, etc., which may include, for example, crushing operations, gravel paving operations, acidification operations, descaling operations, consolidation operations, renovation operations, cleaning operations, diversion operations, etc. Such treatment operations may be characterized by emulsification, de-emulsification, changes in downhole surface wetting properties, or combinations thereof.

[0046] As used herein, the term "drilling operation" refers to the process of forming an oil well in an underground formation. As used herein, the term "drilling fluid" refers to the fluid used to drill the oil well.

[0047] As used herein, the term “stimulation work” refers to activities performed within a well to increase production from the well. As used herein, the term “stimulation fluid” refers to a fluid used in a downhole during stimulation activities to increase the production of hydrocarbon resources from subsurface formations. In some cases, the stimulation fluid may include fracturing fluid or acidification fluid.

[0048] As used herein, the terms “cleaning operation” or “damage control operation” refer to any operation to remove foreign material from a well to increase production. As used herein, the terms “cleaning fluid” or “damage control fluid” refer to a fluid used to remove unwanted material from a well that blocks the flow of a desired fluid. In one example, the cleaning fluid may be an acidified fluid for removing material formed by one or more drilling processes. In another example, the cleaning fluid may be used to remove a filter cake on the well wall. For example, the reaction product of the present invention may promote the release of hydrocarbon resources from a subsurface formation to facilitate well cleaning by altering surface wetting properties. In another embodiment, a treatment fluid containing the reaction product of the present invention may be introduced into a subsurface formation in an emulsified form and may undergo subsequent destruction (de-oiling) internally to promote a desired action within the subsurface formation. In another embodiment, the treatment fluid may promote the de-oiling of fluid downholes, such as emulsified hydrocarbon resources.

[0049] As used herein, the term "fracturing operation" refers to a high-pressure operation that creates or expands multiple flow channels within a subsurface formation. As used herein, the term "fracturing fluid" refers to a viscous fluid used in conjunction with the fracturing operation. Multiple propane particles may be present in the fracturing fluid to keep the flow channels created or expanded in the fracturing operation open.

[0050] As used herein, the term “cleaning operation” refers to any operation designed to maintain, increase, or restore a specific rate of production from a well, which may include a stimulation operation or a cleanup operation. As used herein, the term “cleaning fluid” refers to any fluid used in conjunction with a cleanup operation.

[0051] As used herein, the term “acidification operation” refers to any operation designed to remove acid-soluble material from a well, such as acid-soluble material constituting at least part of a strata. As used herein, the term “acidification fluid” means a fluid used during an acidification operation. Inorganic or organic acids, such as hydrochloric acid or hydrobromide, may be present in a composition used to acidify carbonate strata, whereas hydrofluoric acid may be present in a composition used to acidify silicate strata.

[0052] As used herein, the term "spotting fluid" refers to a fluid designed for the local treatment of subsurface formations. In one example, the spotting fluid may comprise a loss-of-circulation material for treating specific sections of a well, such as sealing cracks in the well and preventing sagging. In another example, the spotting fluid may comprise a water control material or material designed to remove stuck parts of drilling or extraction equipment.

[0053] As used herein, the term "completion fluid" refers to a fluid used during the completion phase of a well, comprising a cementing composition and a cementing fluid.

[0054] The term "cementing fluid" as used herein refers to a fluid used during cementing operations within the wellbore of a well.

[0055] The reaction product of the present disclosure can also be used in conjunction with enhanced oil recovery (EOR) operations. When used in conjunction with EOR operations, the reaction product of the present invention can change surface wetting within subsurface formations to facilitate the recovery of hydrocarbon resources therefrom.

[0056] In any of the aforementioned processing operations, the processing fluid may be foamed. For example, foamed fracturing fluid may be advantageous for delivering propane particulates to a location within the well compared to viscous processing fluid. When foamed, the processing fluid may have a foam quality in the range of about 1% to about 99%.

[0057] The reaction product of the present disclosure may be present in any of the treatment fluids discussed above. The treatment fluid of the present disclosure may be characterized by a reaction product concentration of about 0.1 gpt (gallons per 1,000 gallons) to about 10 gpt, or about 0.1 gpt to about 1 gpt, or about 0.2 gpt to about 0.5 gpt. These concentrations correspond to volume / volume percentages in the range of about 0.01% to about 1%, or about 0.01% to about 0.1%, or 0.02% to about 0.05%. The selected concentration may vary depending on specific requirements for a specified treatment operation and / or specific subsurface conditions occurring in a downhole. In some examples, the reaction product may also be present at a concentration effective for lowering surface tension for neutral surfactants and / or zwitterionic surfactants present in the treatment fluid.

[0058] The processing fluid containing the reaction product of the present invention may optionally further include any number of additives that can be used in the oilfield service industry. Exemplary additives that may be present in the processing fluid together with the reaction product of the present invention include, for example, surfactants, viscosizing agents, gelling agents, gel stabilizers, antioxidants, polymer degradation prevention additives, relative permeability modifiers, scale inhibitors, corrosion inhibitors, chelating agents, foaming agents, defoaming agents, emulsifiers, de-emulsifying agents, iron control agents, propane or other particulates, particulate converters, salts, acids, fluid loss control additives, gases, catalysts, other clay modifiers, dispersants, coagulants, scavengers (e.g., H2S scavengers, CO2 scavengers, or O2 scavengers), lubricants, barriers, friction reducers, crosslinking agents, extenders, solubilizers, pH adjusters (e.g., buffers), hydrate inhibitors, solidification agents, fungicides, catalysts, etc., and combinations thereof. Suitable examples of these additives will be familiar to those skilled in the art.

[0059] Other products

[0060] Compositions of the present invention comprising reaction products of dextrin compounds, dextrans, or fatty acids and any combination thereof may be formulated into a wide range of industrial or consumer products where surfactants may be used. Personal care products may represent a beneficial class of products where the compositions of the present disclosure may be present, considering the relative positive nature of the biomolecules present in the compositions disclosed herein. Exemplary industrial and consumer products where the compositions may be present are further provided below.

[0061] An adjuvant is a composition used together with an active substance to enhance the efficacy or potency of the active substance. In non-limiting examples, the active substance may be a pharmaceutical compound, a personal care compound, or an agricultural compound.

[0062] The composition of the present disclosure (e.g., a dextrin compound as specified above combined with a neutral surfactant or a zwitterionic surfactant, or a reaction product of dextran and a fatty acid) may be present in an adjuvant composition in which various types of surfactants may be used. The composition of the present disclosure may replace the surfactant used in the adjuvant composition or may be used in combination with a surfactant already present in the adjuvant composition. Within the adjuvant composition, the composition may be present in an amount of about 0.01 wt% to about 20 wt%, or about 0.1 wt% to about 10 wt%, or about 1 wt% to about 15 wt%, or about 5 wt% to about 20 wt% of the total adjuvant composition.

[0063] The active compound may be present in the adjuvant composition, or the adjuvant composition may be administered separately from the active compound. If administered separately, the adjuvant composition may be administered before or after the active compound.

[0064] Examples of suitable additional components that may be present in an adjuvant composition containing the reaction product of the present disclosure include other surfactants, defoaming compounds, particulates, metal oxides (e.g., silica, alumina, titania, zirconia, etc.), electrolytes, salts, organic solvents, wetting agents, dispersants, emulsifiers, de-emulsifying agents, penetrating agents, preservatives, coloring agents, acids, bases, buffers, chelating agents, viscosizing agents, thixotropic agents, stabilizers, film-forming agents, plasticizers, preservatives, antioxidants, etc., and any combination thereof. Other surfactants that may be present in the adjuvant composition are not particularly limited and may include any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0065] A foaming agent is a composition in which a large amount of gas is stabilized in the form of bubbles of various sizes within a relatively small volume of liquid, or a composition capable of forming a foam upon the appropriate introduction of gas (a foaming formulation).

[0066] The composition of the present disclosure (e.g., a dextrin compound as specified above combined with a neutral surfactant and a zwitterionic surfactant, or a zwitterionic surfactant in the case of forming a foam with a reaction product of dextran and a fatty acid) may be present in the blowing agent, and various types of surfactants may be used. The composition of the present disclosure may replace the surfactant used in the blowing agent or may be used together with a surfactant already present in the blowing agent. In the blowing agent, the composition may be present in an amount of about 0.01% by weight to about 20% by weight of the total blowing agent, or about 0.1% by weight to about 10% by weight, or about 1% by weight to about 15% by weight, or about 5% by weight to about 20% by weight.

[0067] The blowing agent may contain any combination of cationic surfactants, anionic surfactants, zwitterionic surfactants, or neutral surfactants. The composition disclosed herein may be present in the blowing agent with any cationic surfactant, anionic surfactant, zwitterionic surfactant, neutral surfactant, or any two or more of these surfactants. Alternatively, the composition disclosed herein may replace all or part of any one or more of these surfactants in the blowing agent. For example, the composition of the present invention may replace an anionic surfactant used with a zwitterionic surfactant in the blowing agent. That is, the composition may be present in the blowing agent with one or more zwitterionic surfactants. The composition may replace a sulfosuccinate surfactant or may be used with a sulfosuccinate surfactant, for example, in some blowing agent embodiments.

[0068] Examples of suitable additional components that may be present in a foaming agent containing the reaction product of the present disclosure include, but are not limited to, other surfactants, amines (any one or combination of primary amines, secondary amines, and tertiary amines), diethanolamine, triethanolamine, ethoxylated amines and amidoamines, amine oxides, solvents, water, salts, skin conditioners (e.g., ethylhexylglycerin, hydroxyethylurea, urea, panthenol, glycerin, isopropyl myristate, propylene glycol, tocopheryl acetate and polyquaternium-11), humectants, liquefied gases, supercritical gases, acids, bases, salts, buffers, chelating agents, etc. Suitable examples of these additional components will be familiar to those skilled in the art. Other surfactants that may be included in the foaming agent are not particularly limited and may include any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0069] Hard surface cleaners are compositions that can be used to remove various substances from surfaces such as glass, metal, plastic, stone, concrete, etc. Hard surfaces that can be cleaned with hard surface cleaners include, for example, windows, countertops, appliances, floors, driveways, toilets, showers and bathtubs, sinks, etc. The substances that can be removed from these types of hard surfaces and others are extensive and include, but are not limited to, dust, grease, soap residue, limescale, and similar hard water deposits.

[0070] The composition of the present disclosure (e.g., a dextrin compound as specified above combined with a neutral surfactant or a zwitterionic surfactant, or a reaction product of a dextran and a fatty acid) may be present in a hard surface cleaner in which various types of surfactants may be used. The composition of the present disclosure may replace the surfactant used in the hard surface cleaner or may be used in combination with a surfactant already present in the hard surface cleaner. In the hard surface cleaner, the composition may be present in an amount of about 0.01% by weight to about 20% by weight, or about 0.1% by weight to about 10% by weight, or about 1% by weight to about 15% by weight, or about 5% by weight to about 20% by weight of the total hard surface cleaner.

[0071] Examples of suitable additional components that may be present in a hard surface cleaner containing the reaction product of the present invention include, but are not limited to, other surfactants, foaming compounds, defoaming compounds, salts such as alkali metal carbonates, organic solvents such as glycols or glycol ethers, wetting agents, dispersants, emulsifiers, de-emulsifiers, coloring agents, acids, bases, buffers, chelating agents, anti-striping agents, alkanolamines, etc. (including any combination thereof) and any combination thereof. Other surfactants that may be present in the hard surface cleaner are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0072] Skin creams and lotions are compositions that can moisturize or otherwise improve the appearance of the skin. Skin creams and lotions include gel formulations for application to the skin and may have a higher viscosity than creams or lotions.

[0073] The composition of the present disclosure (e.g., a dextrin compound as specified above combined with a neutral surfactant or a zwitterionic surfactant, or a reaction product of a dextran and a fatty acid) may be present in skin creams and lotions where a surfactant may be used. The composition may replace a surfactant used in a skin cream or lotion, or may be used in combination with a surfactant already present in a skin cream or lotion. In a skin cream or lotion, the composition may be present in an amount of about 0.01% to about 20% by weight, or about 0.1% to about 10% by weight, or about 1% to about 15% by weight, or about 5% to about 20% by weight of the total skin cream or lotion.

[0074] Examples of suitable additional ingredients that may be present in the skin cream or lotion disclosed herein include other surfactants, emulsifiers, essential oils, waxes, fats, solvents, viscosizing agents, monoalcohols, diols, polyols, diol and polyol ethers, milk proteins, emollients, humectants, skin conditioners, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, lubricants, anti-wrinkle agents, moisturizers, radical inhibitors and other antioxidants, vitamin A, vitamin E, ceramides, fatty acids, fatty esters, fatty alcohols, hyaluronic acid, sodium pyroglutamate, glycerin, aloe vera, fragrances, coloring agents, preservatives, sunscreens, etc., and any combination thereof. Other surfactants that may be present in the skin cream and lotion are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants. The reaction product can replace at least a portion of one or more existing surfactants in the skin cream or lotion, or supplement the amount of one or more existing surfactants in the skin cream or lotion.

[0075] Body washes and shampoos are cleansing compositions formulated for application to the skin or hair. Liquid soaps for more generalized personal cleansing have a composition similar to some body washes and shampoos and can be manufactured with many of the same ingredients.

[0076] The composition of the present disclosure (e.g., a dextrin compound as specified above combined with a neutral surfactant or a zwitterionic surfactant, or a reaction product of a dextran and a fatty acid) may be present in a body wash, shampoo, or liquid soap in which a surfactant may be used. The composition of the present disclosure may replace a surfactant used in a body wash, shampoo, or liquid soap, or may be used in combination with a surfactant already present in a body wash, shampoo, or liquid soap. In a body wash, shampoo, or liquid soap, the composition may be present in an amount of about 0.01% to about 20% by weight, or about 0.1% to about 10% by weight, or about 1% to about 15% by weight, or about 5% to about 20% by weight of the total body wash, shampoo, or liquid soap.

[0077] Examples of suitable additional ingredients that may be present in the body wash, shampoo, or liquid soap disclosed herein include, but are not limited to, other surfactants, conditioners, amidoamines, fragrances, colorants, essential oils, foaming agents, wetting agents, fatty acids, fatty esters, fatty alcohols, waxes, biocides, soaps, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, pearlizing agents, thickeners, moisturizers, antioxidants, sunscreens, etc. Exemplary examples of body wash, shampoo, and liquid soap may include water, an effective amount of composition, optionally another surfactant, 0-4% pearlizing agent, 0-1% suspension aid, 0-2% fragrance, 0-0.25% chelating agent, 0-1% preservative, 0-2% colorant, and 0-25% conditioner. Other surfactants that may be present in body wash, shampoo and liquid soap are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0078] Sunscreen is a substance that can be applied to the skin to protect against the sun. Sunscreen can be formulated as a "stick" type cream or a suitable wax base for application to the skin.

[0079] The composition of the present disclosure (e.g., a reaction product of a fatty acid and a dextrin or dextran as specified above combined with a neutral surfactant or a zwitterionic surfactant) may be present in a sunscreen where a surfactant may be used. The composition of the present disclosure may replace a surfactant used in the sunscreen or may be used in combination with a surfactant already present in the sunscreen. In the sunscreen, the composition may be present in an amount of about 0.01% by weight to about 20% by weight of the total sunscreen, or about 0.1% by weight to about 10% by weight, or about 1% by weight to about 15% by weight, or about 5% by weight to about 20% by weight.

[0080] Examples of suitable additional ingredients that may be present in the sunscreen include other surfactants, conditioners, titanium dioxide, zinc oxide, organic UV absorbers, film-forming agents, solvents, aerosol propellants, waxes, fats, oils, humectants, fragrances, colorants, essential oils, fatty acids, fatty esters, fatty alcohols, preservatives, acids, bases, buffers, chelating agents, thickeners, insecticides, skin conditioners, etc., and any combination thereof. Other surfactants that may be present in the sunscreen are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0081] Organic UV absorbers that may be present in the sunscreen together with the composition include para-aminobenzoic acid, avobenzone, cinoxate, dioxybenzone, homosalate, menthyl anthranilate, octyl salicylate, oxybenzone, Padimate O, phenylbenzimidazole sulfonic acid, sulysobenzone, trollamine salicylate, diethanolamine methoxycinnamate, digalloy trioleate, ethyl dihydroxypropyl PABA, glyceryl aminobenzoate, lawson containing dihydroxyacetone, red petrolatum, ethylhexyl triazone, dioctyl butamido triazone, benzylidene malonate polysiloxane, terephthalylidene dicamphorsulfonic acid, disodium phenylsulfonic acid, disodium phenylsulfonic acid diethylaminohydroxybenzoyl hexyl benzoate, and bis diethylaminohydroxybenzoyl Benzoate, bis-benzoxazoyphenyl ethylhexyliminotriazine, drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutylphenol and bis-ethylhexyloxyphenol methoxyphenyltriazine, 4-methylbenzylidene camphor, isopentyl 4-methoxycinnamate, phenylbenzimidazole sulfonate, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-(2-beta-glucopyrano-siloxy)propoxy-2-hydroxybenzophenone and bis-sodium phenylene-1,4-bis(2-benzimidazyl)-3,3'-5,5'-tetrasulfonate, 2-ethylhexyl-p-methoxycinnamate, 4-tert-4'-methoxydibenzoylmethane, octocrylene, 2,4-bis-[{4-(2-ethylhexyloxy)-2-hydroxy}-phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine, methylene bis-benzotriazolyl tetramethylbutylphenol, 2,4,6-tris-[4-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, diethylaminohydroxybenzoyl hexyl benzoate, oxybenzone and dihydroxy dimethoxy benzophenone, and mixtures thereof, but are not limited thereto.

[0082] Other organic UV absorbers suitable for inclusion in sunscreens include, but are not limited to, bis-resorcinyl triazine; benzimidazole derivatives; 4-methylbenzylidene camphor; benzoylpiperazine derivatives; benzoxazole derivatives; diarylbutadiene derivatives; phenylbenzotriazole derivatives; benzylidene malonate; TEA-salicylate; imidazoline derivatives; naphthalate; merocyanine derivatives; aminobenzophenone derivatives; dibenzoylmethane derivatives; β,β-diphenylacrylate derivatives; camphor derivatives; salicylate derivatives; anthranilate derivatives; and benzalmalonate derivatives.

[0083] In addition to formulations in which the sunscreen is alone, the composition of the present invention may be present in sunscreens included in other products such as lotions, colognes, cosmetics, body washes, and shampoos.

[0084] Hair gel and hair spray are formulations that can be used to hold hair in place or, optionally, to detangle hair. Hair spray is in the form of an aerosol, whereas gel is a high-viscosity liquid that can be applied by hand.

[0085] The composition of the present disclosure (e.g., a reaction product of a fatty acid and a dextrin or dextran as specified above combined with a neutral surfactant or a zwitterionic surfactant) may be present in hair sprays and hair gels where a surfactant may be used. The composition of the present disclosure may replace a surfactant used in a hair spray or hair gel, or may be used in combination with a surfactant already present in a hair spray or hair gel. In a hair spray or hair gel, the composition may be present in an amount of about 0.01% by weight to about 20% by weight, or about 0.1% by weight to about 10% by weight, or about 1% by weight to about 15% by weight, or about 5% by weight to about 20% by weight of the total hair gel or hair spray.

[0086] Examples of suitable additional ingredients that may be present in hair spray or hair gel include, but are not limited to, other surfactants, cellulose-based biopolymers, water-soluble polymers, polyalkylene glycols, polyalkylene glycol esters, conditioning agents, skin softeners, humectants, emulsifiers, opacifiers, thickeners, foam stabilizers, viscosity enhancers, sequestering agents, antioxidants, anti-dandruff agents, suspending agents, proteins, fragrances, sunscreens, plant extracts, essential oils, fatty acids, fatty esters, fatty alcohols, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, waxes, oils, aerosol propellants, polyvinylpyrrolidone, polyvinyl acetate, vinyl acetate-crotonic acid copolymers, acrylic acid copolymers, plasticizers, alcohols, etc. Other surfactants that may be present in hair spray and hair gel are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants.

[0087] One or more examples of hair sprays or hair gels may comprise the composition of the present disclosure and one or more of cetearyl alcohol, behentrimonium chloride, cyclopentasiloxane, dimethicone, ethylhexyl isononanoate, behenyl alcohol, meadowfoam seed oil, cyclohexasiloxane, olive fruit oil, Prunus amygdalus dulcis, stearamidopropyl dimethylamine, behentrimonium methosulfate, amodimethicone, panthenol, glycol stearate, ceteth-2, hydroxyethylcellulose, phenoxyethanol, methylparaben, propylparaben, citric acid, mica, titanium dioxide, iron oxide, fragrance, or combinations thereof.

[0088] One or more examples of hair spray or hair gel may comprise the composition of the present invention and one or more cyclomethicone, jojoba ester, dimethicone copolyol, non-fat milk powder, soy protein, stearic acid, capric acid / caprylic acid stearic acid triglyceride, jojoba oil, hybrid sunflower oil, cetearyl alcohol, glyceryl stearate, PEG-40 stearate, aloe vera gel, acrylate / C10-30 alkyl acrylate crosspolymer, propylene glycol, tocopheryl acetate, methylparaben, propylparaben, fragrance, or a combination thereof.

[0089] Cosmetics are formulations that can be used to alter or improve appearance. Exemplary cosmetics include, but are not limited to, lipsticks, blushes, mascaras, foundations, eyeliners, etc. Forms of cosmetics may include, for example, emulsions, creams, gels, dispersions, sticks, etc. Suitable emulsions in cosmetics may include oil-in-water or water-in-oil emulsions.

[0090] The composition of the present disclosure (e.g., a reaction product of a fatty acid and a dextrin or dextran as specified above combined with a neutral surfactant or a zwitterionic surfactant) may be present in various types of cosmetics where surfactants may be used. The composition of the present disclosure may replace surfactants used in cosmetics or may be used in combination with surfactants already present in cosmetics. In cosmetics, the composition may be present in an amount of about 0.01% by weight to about 20% by weight of the total cosmetic, or about 0.1% by weight to about 10% by weight, or about 1% by weight to about 15% by weight, or about 5% by weight to about 20% by weight.

[0091] Examples of suitable additional ingredients that may be present in cosmetics include, but are not limited to, other surfactants, fragrances, preservatives, colorants, UV absorbers, moisture retainers, emulsifiers, gelling agents, oils, thickeners, foam stabilizers, viscosity enhancers, preservatives, sequestering agents, antioxidants, suspending agents, proteins, fragrances, sunscreens, plant extracts, essential oils, fats (e.g., shea butter, mango seed butter, and cocoa seed butter), fatty acids, fat esters, fatty alcohols, biocides, soaps, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, waxes (e.g., myristyl myristate, camellia leaf extract, jojoba, sunflower seed, carnauba wax, candelilla wax, and beeswax), and any combination thereof. Some examples of ingredients that may be present in cosmetics include, for example, higher fatty alcohols such as cetyl alcohol, stearyl alcohol, and behenyl alcohol; It may include higher fatty acids including caprylic acid / capric acid triglycerides, lauric acid, myristic acid, palmitic acid, and stearic acid; hydrocarbons including ceresin; natural oils such as meadowfoam seed oil, sunflower seed oil, macadamia seed oil, green tea seed oil, ginger oil, ginseng oil, coconut oil, olive oil, and camellia oil; esters including phytosteryl / octyldodecyl lauroyl glutamate, isostearyl isostearate, methylheptyl isostearate, dicaprylyl carbonate, and isopropyl palmitate; ethers including dicaprylyl ether; silicone oils including dimethicone, cyclopentasiloxane, cyclohexasiloxane, phenyltrimethicone, trisiloxane, and methyltrimethicone; and hydrocarbons including squalene. Other surfactants that may be present in the cosmetic are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants. The cosmetic of the present invention may be formulated into any suitable form including sticks, creams, powders, gels, etc.

[0092] Deodorants and antiperspirants are formulations that can be used to control body odor. The deodorants and antiperspirants of the present invention may be formulated in the form of a stick, gel, powder, or aerosol.

[0093] The composition of the present disclosure (e.g., a reaction product of a fatty acid and a dextrin or dextran as specified above combined with a neutral surfactant or a zwitterionic surfactant) may be present in and used in deodorants and antiperspirants containing surfactants. The composition of the present disclosure may replace a surfactant used in a deodorant or antiperspirant, or may be used in combination with a surfactant already present in a deodorant or antiperspirant. In a deodorant or antiperspirant, the composition may be present in an amount of about 0.01% to about 20% by weight, or about 0.1% to about 10% by weight, or about 1% to about 15% by weight, or about 5% to about 20% by weight of the total deodorant or antiperspirant.

[0094] Examples of suitable additional ingredients that may be present in the deodorizers or antiperspirants disclosed herein include, but are not limited to, other surfactants, aluminum salts (e.g., alum, aluminum chloride, aluminum chlorohydrate, aluminum-zirconium compounds, aluminum-zirconium tetrachlorohydrexglyces, aluminum-zirconium tetrachlorohydrexglyces), antimicrobial agents, parabens, alcohols, propylene glycol, hexamethylenetetramine, acids, bases, buffers, chelating agents, fragrances, preservatives, coloring agents, hygroscopic agents (desiccant), emulsifiers, gelling agents, oils, thickeners, foam stabilizers, viscosity enhancers, sequestering agents, antioxidants, suspending agents, fragrances, essential oils, fats, fatty acids, fatty esters, fatty alcohols, waxes, etc. Other surfactants that may be present in deodorants and antiperspirants are not particularly limited and may be any one or a combination of cationic, anionic, neutral, or zwitterionic surfactants. The deodorants and antiperspirants of the present disclosure may be formulated in any suitable form including sticks, creams, powders, gels, etc.

[0095] Compositions of the present invention comprising reaction products of dextrin compounds, dextrans, or fatty acids and any combination thereof may also find exemplary uses and formulations outside of personal care spaces. In addition to the aforementioned oilfield applications, compositions of the present invention may be included in applications requiring metal isolation from fluids, such as in foam flotation processes. Foam flotation processes may be performed in various cases, such as mining runoff or water treatment. In such applications, compositions of the present disclosure may replace surfactants used in foam flotation or may be used in conjunction with surfactants already present in the foam flotation process. In a given foam flotation process, the composition may be present in an amount of about 0.01 wt% to about 20 wt%, or about 0.1 wt% to about 10 wt%, or about 1 wt% to about 15 wt%, or about 5 wt% to about 20 wt% of the total foam flotation fluid.

[0096] In some embodiments, the compositions of the present invention may be used in rough and clean circuits to promote clay dispersion, water conditioning, additive reinforcement, and / or emulsification of metal inhibitors such as Mn and Fe. Any conventional blowing agent may be used with the compositions disclosed herein. Suitable blowing agents and details regarding blowing agents will be familiar to those skilled in the art.

[0097] The embodiments disclosed herein include the following:

[0098] A. A composition comprising a reaction product of a sugar polymer with a fatty acid. The composition comprises a reaction product of a sugar polymer and a fatty acid obtained in the presence of water, a hydroxide base, and a neutral surfactant, wherein the sugar polymer comprises dextran, a dextrin compound, or a combination thereof.

[0099] A1. A composition in which the sugar polymer comprises dextran.

[0100] A2. A composition in which the sugar polymer comprises a dextrin compound.

[0101] B. A method for functionalizing polysaccharides. The method comprises the steps of: heating a sugar polymer comprising dextran, a dextrin compound, or any combination thereof, a fatty acid, a hydroxide base, and a neutral surfactant in water; and obtaining a reaction product of the sugar polymer and the fatty acid in an aqueous phase.

[0102] B1. A method in which the sugar polymer comprises dextran.

[0103] B2. A method in which the sugar polymer comprises a dextrin compound.

[0104] C. Method for treating underground. The method comprises the steps of providing a treatment fluid comprising a composition of A, A1 or A2, and introducing the treatment fluid into an underground formation.

[0105] D. Foaming formulation. The foaming formulation comprises the composition of A, A1, or A2.

[0106] D1. Soaps and detergents comprising the foaming formulation of D.

[0107] E. Foaming formulation. The foaming formulation comprises a gas and an aqueous fluid comprising a composition of A, A1, or A2 that is mixed with the gas to form a number of bubbles.

[0108] F. Method for forming a foam. The method comprises the steps of providing an aqueous fluid comprising a composition of A, A1 or A2, and inducing foam formation in the aqueous fluid.

[0109] Examples A, A1, A2, B, B1, B2, C, D, D1, E, and F may have one or more of the following additional elements in any combination.

[0110] Element 1: Sugar polymers contain dextrin compounds, and dextrin compounds contain maltodextrin.

[0111] Factor 2: Maltodextrin has a dextrose equivalent value of about 3 to about 20.

[0112] Factor 3: Maltodextrin has a dextrose equivalent value of about 4.5 to about 7.0.

[0113] Factor 4: Maltodextrin has a dextrose equivalent value of about 9.0 to about 12.0.

[0114] Element 5: Fatty acids contain about 4 to about 30 carbon atoms.

[0115] Factor 6: Fatty acids are butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelavonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melisic acid, crotonic acid, cervonic acid, linoleic acid, linolerid acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, saphenic acid, vacsenic acid, folic acid, oleic acid, pinolenic acid, stearidonic acid, eleostearic acid, elelaidic acid, gondoic acid, gadoleic acid, It includes at least one fatty acid selected from the group consisting of erucic acid, eicosenic acid, eicosadienkoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, nervonic acid, midic acid, adrenergic acid, and combinations thereof.

[0116] Element 7: Neutral surfactants include cocamide diethanolamine.

[0117] Factor 8: The molar ratio of fatty acids to dextrin in the reaction product is mol 지방산 :mole 글루코스 단량체 It is approximately 0.2 or higher based on .

[0118] Factor 8A: The molar ratio of fatty acids to dextrin in the reaction product is mol 지방산 :mole 글루코스 단량체It is approximately 0.05 or higher based on .

[0119] Factor 9: The molar ratio of fatty acids to dextrin in the reaction product is mol 지방산 :mole 글루코스 단량체 Based on, it is approximately 0.35 or higher.

[0120] Element 10: The treatment fluid is emulsified when introduced into the underground formation or is emulsified within the underground formation.

[0121] Element 11: The treatment fluid contains a water-in-oil emulsion.

[0122] Element 12: The treatment fluid contains an oil-in-water emulsion.

[0123] Element 13: The treatment fluid contains a microemulsion when introduced into the underground formation.

[0124] Element 14: The treatment fluid promotes enhanced oil recovery within underground formations.

[0125] Element 14A: The processing fluid is foamed.

[0126] Element 15: The method further comprises the steps of combining a fatty acid, a hydroxide base, and a neutral surfactant in water to form a mixture, heating the mixture until the fatty acid is dissolved and a homogeneous mixture is formed, and combining a sugar polymer with the homogeneous mixture.

[0127] Element 15A: The method further includes the step of stirring an aqueous phase to form a foam.

[0128] Element 16: The foaming formulation comprises a composition.

[0129] Element 17: The effervescent formulation contains soap.

[0130] Element 18: The step of inducing foam formation includes the step of stirring an aqueous fluid to introduce gas therein.

[0131] As non-limiting examples, exemplary combinations applicable to A, A1, A2, B, B1, B2, C, D1, E, and F include, but are not limited to, 1, and 2, 3, or 4; 5, or 6, and 2, 3, or 4; 1, and 7; 1, 8, or 9; 2, 3, or 4, and 5, or 6; 2, 3, or 4, and 7; 2, 3, or 4, and 8, or 9; 5, or 6, and 7; 5, or 6, 8, or 9; and 7, and 8, or 9. Any of the above may be additionally combined with one or more of 10 to 18.

[0132] Additional embodiments disclosed herein include the following:

[0133] A'. A composition comprising a reaction product of a sugar polymer with a fatty acid. The composition comprises a neutral surfactant or a reaction product thereof, and a reaction product of a sugar polymer and a fatty acid, wherein the sugar polymer comprises dextran, a dextrin compound, or any combination thereof. The reaction product is present at a concentration effective for lowering the surface tension of the neutral surfactant.

[0134] A1'. A', wherein the sugar polymer comprises dextran.

[0135] A2'. A', wherein the sugar polymer comprises a dextrin compound, preferably maltodextrin.

[0136] B'. A method for functionalizing polysaccharides. The method comprises the steps of: heating a sugar polymer comprising dextran, a dextrin compound, or any combination thereof, a fatty acid, and a hydroxide base in water; obtaining a reaction product of the sugar polymer and the fatty acid in an aqueous phase; and combining a neutral surfactant or a reaction product thereof with the reaction product of the sugar polymer and the fatty acid in the aqueous phase.

[0137] B1'. In B', the sugar polymer comprises dextran, method.

[0138] B2'. In B', the sugar polymer comprises a dextrin compound such as maltodextrin.

[0139] C'. Method for treating an underground structure. The method comprises the steps of providing a treatment fluid comprising the composition of A', A1' or A2', and introducing the treatment fluid into an underground structure.

[0140] D'. Foaming formulation. The foaming formulation comprises the composition of A', A1', or A2'.

[0141] D1'. Soap and detergent comprising the foaming formulation of D'.

[0142] E'. Foaming formulation. The foaming formulation comprises a gas and an aqueous fluid of the A', A1', or A2' composition that is mixed with the gas to form a number of bubbles.

[0143] F'. Method for forming a foam. The method comprises the steps of providing an aqueous fluid comprising a composition of A', A1' or A2', and inducing foam formation in the aqueous fluid.

[0144] G'. A personal care product comprising the reaction product of A', A1' or A2'.

[0145] H'. A composition comprising a neutral surfactant, a hydroxide base, a sugar polymer, and a fatty acid. The sugar polymer comprises dextran, a dextrin compound, or a combination thereof.

[0146] Examples A', A1', A2', B', B1', B2', C', D', D1', E', F', G' and H' may have one or more of the following additional elements in any combination.

[0147] Element 1': Sugar polymers contain dextrin compounds, and dextrin compounds contain maltodextrin.

[0148] Factor 2': Maltodextrin has a dextrose equivalent value of about 3 to about 20.

[0149] Factor 3': Maltodextrin has a dextrose equivalent value of about 4.5 to about 7.0.

[0150] Factor 4': Maltodextrin has a dextrose equivalent value of about 9.0 to about 12.0.

[0151] Element 5': Fatty acids contain about 4 to about 30 carbon atoms.

[0152] Factor 6': Fatty acids are butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelavonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melisic acid, crotonic acid, cervonic acid, linoleic acid, linolerid acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, saphenic acid, vacsenic acid, folic acid, oleic acid, pinolenic acid, stearidonic acid, eleostearic acid, ellaidic acid, gondoic acid, It includes at least one fatty acid selected from the group consisting of gadolic acid, erucic acid, eicosenic acid, eicosadienkoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, nervonic acid, mitic acid, adrenergic acid, and combinations thereof.

[0153] Element 7': A neutral surfactant comprises cocamide diethanolamine or a reaction product thereof, or a neutral surfactant comprises cocamide diethanolamine.

[0154] Element 7A': The reaction product is formed in the presence of a neutral surfactant.

[0155] Factor 8': The molar ratio of fatty acids to dextrin in the reaction product is mol 지방산 :mole 글루코스 단량체 It is approximately 0.2 or higher based on .

[0156] Factor 8A': The molar ratio of fatty acids to dextrin in the reaction product is mol지방산 :mole 글루코스 단량체 It is approximately 0.05 or higher based on .

[0157] Factor 9': The molar ratio of fatty acids to dextrin in the reaction product is mol 지방산 :mole 글루코스 단량체 Based on, it is approximately 0.35 or higher.

[0158] Element 10': The reaction product of the sugar polymer is obtained in the presence of water and a hydroxide base.

[0159] Element 11': The reaction product of the sugar polymer includes the fat ester reaction product.

[0160] Element 12': The treatment fluid is emulsified when introduced into the underground formation or is emulsified within the underground formation.

[0161] Element 13': The treatment fluid contains a water-in-oil emulsion.

[0162] Element 14': The treatment fluid contains an oil-in-water emulsion.

[0163] Element 15': The treatment fluid contains a microemulsion when introduced into the underground formation.

[0164] Element 16': The treatment fluid promotes enhanced oil recovery within underground formations.

[0165] Element 16A': The processing fluid is foamed.

[0166] Element 17': The method comprises the steps of mixing a fatty acid, a hydroxide base, and a neutral surfactant in water to form a mixture, heating the mixture until the fatty acid is dissolved and a homogeneous mixture is formed, and combining a sugar polymer with the homogeneous mixture.

[0167] Element 18A': The method further includes the step of stirring an aqueous phase to form a foam.

[0168] Element 19': The effervescent formulation comprises a composition.

[0169] Element 20': The effervescent formulation contains soap.

[0170] Element 21': Inducing foam formation includes the step of introducing gas by stirring an aqueous fluid.

[0171] As non-limiting examples, exemplary combinations applicable to A', A1', A2', B', B1', B2', C', D', D1', E', F', and G' include, but are not limited to: 1' and 2', 3' or 4'; 5' or 6', and 2', 3' or 4'; 1' and 7' or 7A'; 1', and 8' or 9'; 2', 3' or 4', and 5' or 6'; 2', 3' or 4' and 7' or 7A'; 2', 3' or 4' and 8' or 9'; 5' or 6' and 7' or 7A'; 5' or 6' and 8' or 9'; and 7' or 7A', and 8' or 9'. Any of the aforementioned may be combined with one or more of 10'-21'.

[0172] To better understand the present disclosure, the following examples of various representative embodiments are provided. The following embodiments should not be construed in any way as limiting or defining the scope of the invention.

[0173] Examples

[0174] Comparative Example 1: Acid-catalyzed synthesis of maltodextrin using lauric acid. A solution containing 10 wt% maltodextrin (MALTRIN M100, DE=9.0-12.0, 30% active solution) and 6.18 wt% lauric acid was prepared in DMSO. Five drops of phosphoric acid were added, and the reaction mixture was heated at 110°C for 3 hours. Three volumes of isopropyl alcohol were added to precipitate the reaction product, and the white precipitate was collected by decantation and dried. The product was characterized by FTIR and 1H NMR. The spectral characterization was consistent with the conversion of maltodextrin into the reaction product.

[0175] For surface tension measurement (Table 2), the separated reaction product was redissolved to a concentration of 13.17 wt% in the presence of 5 wt% cocamide diethanolamine (CocoDEA) and 6 wt% sodium dodecylbenzene sulfonate (SDDBS).

[0176] Comparative Example 2: Acid chloride-based reaction of maltodextrin A solution containing 10 wt% maltodextrin (MALTRIN M100, DE=9.0-12.0, 30% active solution) and 6.75 wt% lauroyl chloride was prepared in formamide. A few drops of phosphoric acid were added, and the reaction mixture was heated at 105°C for 2 hours. 3 volumes of isopropyl alcohol were added to precipitate the reaction product, yielding an amber tar-like fluid. The product was analyzed using FTIR and 1 It was characterized by H NMR. The spectral characterization was consistent with the conversion of maltodextrin into reaction products.

[0177] For surface tension measurement (Table 2), the isolated reaction product was redissolved to a concentration of 13.17 wt% in the presence of 5 wt% cocamide diethanolamine (CocoDEA) and 6 wt% sodium dodecylbenzene sulfonate (SDDBS).

[0178] Example 1A: General procedure for the preparation of the reaction product of maltodextrin under basic conditions296.25 g of water, 25.00 g of cocamide diethanolamine (CocoDEA), and 10.00 g of KOH (45% active solution) were combined. The reaction mixture was mechanically stirred and heated to 65°C. Then, 18.75 g of fatty acid and 150.0 g of maltodextrin (MALTRIN M100, Grain Processing Corporation, Muscatine, Iowa; DE=9.0-12.0) as a 30% active solution were added to the reaction mixture. Once the maltodextrin dissolved, heating was stopped and the reaction mixture was stirred until it reached room temperature. The reaction product was used without further processing as described below. Table 1A shows the maltodextrin reaction product synthesized as above and tested in subsequent examples. Caprylic acid is synonymous with octanoic acid, lauric acid is synonymous with dodecanoic acid, and stearic acid is synonymous with octadecanic acid.

[0179] Table 1A Sample fatty acid Fatty acid:maltodextrin molar ratio (as glucose monomers) A butyric acid 0.77 B Caprylic acid 0.47 C Mount Laur 0.34 D stearic acid 0.24

[0180] For all samples except Sample A, a standard synthesis procedure was followed. For Sample A, 27.5 g KOH (45% active) and 278.75 g water were used, and other reaction parameters were kept the same. The calculated molar ratio is assumed to be the total maltodextrin minus the molecular weight of water (18.02 g / mol) from the molecular weight of glucose (180.16 g / mol) = 162.14 g / mol.

[0181] Example 1B: Alternative procedure for the preparation of a reaction product of maltodextrin under basic conditions A solution containing 10 wt% maltodextrin (MALTRIN M100, DE=9.0-12.0, 30% active solution), 6.18 wt% lauric acid, and 1.73 wt% KOH was prepared in water. The reaction mixture was then heated at 65°C for 30 minutes. Three volumes of isopropyl alcohol were added to precipitate the reaction product, and the white precipitate was collected by decantation and dried. The product was analyzed using FTIR and 1It was characterized by H NMR. The spectral characterization was consistent with the conversion of maltodextrin into reaction products. Other fatty acids may react similarly.

[0182] For surface tension measurement (Table 2), the separated reaction product was redissolved to a concentration of 13.17 wt% in the presence of 5 wt% cocamide diethanolamine (CocoDEA) and 6 wt% sodium dodecylbenzene sulfonate (SDDBS). As shown in Table 2, similar surface tension performance was achieved between the reaction products of Example 1A and Comparative Examples 1 and 2.

[0183] Example 2: General procedure for the preparation of the reaction product of dextran under basic conditions The reaction product was formed from dextran in a manner similar to that described above for maltodextrin. The dextran had a molecular weight of 500,000 and an activity in solution of 9%. Table 1B shows the dextran reaction product synthesized as above and tested in subsequent examples. Caprylic acid is synonymous with octanoic acid, lauric acid is synonymous with dodecanoic acid, palmitic acid is synonymous with hexadecanoic acid, and stearic acid is synonymous with octadecanic acid.

[0184] Table 1B Sample fatty acid Fatty acid weight:dextran weight ratio Fatty acid:dextran molar ratio (as glucose monomers) E1 Caprylic acid 1:10 0.11 E2 Caprylic acid 1:5 0.22 E3 Caprylic acid 1:2 0.57 E4 Caprylic acid 1:1 1.13 F1 Mount Laur 1:10 0.081 F2 Mount Laur 1:5 0.16 F3 Mount Laur 1:2 0.41 F4 Mount Laur 1:1 0.81 G1 palmitic acid 1:10 0.063 G2 palmitic acid 1:5 0.13 G3 palmitic acid 1:2 0.32 G4 palmitic acid 1:1 0.63 H1 stearic acid 1:10 0.057 H2 stearic acid 1:5 0.11 H3 stearic acid 1:2 0.28 H4 stearic acid 1:1 0.57

[0185] Characterization of Comparative Examples 1 and 2 related to Example 1B Table 2 summarizes the surface tension values ​​for the reaction products of Comparative Examples 1 and 2 and the reaction product of Example 1B (an alternative formulation under basic conditions) at a concentration of 1 gpt (gallon per 1000 gallons) compared to control samples containing 5 wt% CocoDEA or 5 wt% CocoDEA / 6 wt% SDDBS. Surface tension (ST) measurements were performed at room temperature using a Bolin Scientific Tensiometer. Interfacial tension (IFT) measurements were performed using a hook needle syringe to form a drop of oil in water.

[0186] Entry Sample Surface tension at 1 gpt (Da-in / cm) 1 Control group (5 wt% CocoDEA / 6 wt% SDDBS) 31.26 2 Control group (5 wt% CocoDEA) 34.49 3 Comparative Example 1 31.77 4 Comparative Example 2 31.48 5 Example 1B 31.51

[0187] The control samples and comparative / experimental samples contained the same concentration of CocoDEA or CocoDEA / SDDBS. As indicated, the reaction products prepared under basic conditions (Item 5) provided performance similar to that obtained under acidic conditions (Items 3 and 4). In each case, the surface tension was similar to that of the CocoDEA / SDDBS control containing only the surfactant (Item 1). The surface tension values ​​decreased by approximately 10% compared to the CocoDEA-alone control (Item 2). This remarkable result is explained in detail below.

[0188] Emulsion performance of dextrin reaction products Each reaction product prepared as described above in Example 1A was formulated at 0.5 gpt (gallons per 1000 gallons) and 1 gpt and combined with Terero oil or Wolfcamp A oil. Terero oil is an emulsifying oil, and Wolfcamp A oil is a non-emulsifying oil. Subsequently, the mixture of each oil was emulsified, and the degree of emulsification was tracked as a function of time compared to a blank. The blank consisted of each oil without additional emulsifiers. Emulsification was performed at room temperature by hand shaking 50 mL of sample and 50 mL of oil at a rate of approximately 2 times per second for 60 seconds. The emulsion was immediately poured into a graduated cylinder, and the heights of the water layer, oil layer, and remaining emulsion layer were recorded using time-lapse photography. In the case of Wolfcamp A oil, the oil layer and the water layer were assumed to be identical because the oil layer is difficult to distinguish from the emulsion layer. Figures 1a through 1d show plots of the emulsification rate as a function of time for Terero oil emulsified with sample AD, respectively. Figures 2a to 2d each show plots of the emulsification rate as a function of time for Wolfcamp A oil emulsified with sample AD.

[0189] Both oils were initially emulsified in the presence of maltodextrin reaction products, but the emulsions degraded over time, albeit at different rates. Terero oil generally exhibited only slight changes in emulsification behavior in the presence of reaction products formed from carboxylic acids of varying chain lengths. In contrast, for non-digested Wolfcamp A oil, the maltodextrin reaction products sometimes resulted in faster emulsion breakdown than the control group. The results suggest that the maltodextrin reaction products, particularly the specific fatty acids used for functionalization and the amount of reaction products present, can alter the breakdown characteristics of the non-digested Wolfcamp oil itself to varying degrees. These differences in performance may result from changes in the hydrophilic-lipophilic balance. Furthermore, the breakdown characteristics may differ from those of CocoDEA alone, which provides nearly complete breakdown of Wolfcamp oil within approximately 30 minutes at 1 gpt (data not shown).

[0190] Fluid properties of dextrin reaction products Critical Micellar Concentration (CMC) and Surface Tension (ST) measurements were performed at room temperature using a Bolin Scientific tension meter. Figures 3a through 3d show plots of surface tension as a function of concentration for samples AD, respectively. As shown, samples B and C reached the CMC at a reaction product concentration of approximately 0.5 gpt. The surface tension at the CMC was approximately 30 dynes / cm or slightly lower. In contrast, samples A and D tended toward lower surface tension values ​​despite having a higher CMC. Thus, the above emulsion performance measurements were performed above the CMC for at least samples B and C. The surface tension was slightly higher for 0.2 wt% KCl compared to that obtained with tap water.

[0191] The surface tension performance of the individual components of the reaction mixture used to produce Sample C was also compared with the surface tension performance of the reaction product itself. Measurements were performed at 1 gpt and 2 gpt as specified in Table 3 below.

[0192] Entry ingredient ST in 1 gpt (dyne / cm) ST in 2 gpt (Da-in / cm) 1 Maltodextrin (30% active solution) 73.03 72.85 2 Maltodextrin (30% active solution), 1.7% KOH (45% active solution) and 6.18% lauric acid (heated as above) n / d 77.39 3 10% maltodextrin (30% active solution), 5% CocoDEA neutral surfactant solution (heated as above) 49.23 35.89 4 5% CocoDEA neutral surfactant solution (heated as above) 34.49 31.93 5 5% CocoDEA neutral surfactant solution containing 2% KOH (45% active solution) (heated as above) 36.73 35.00 6 5% CocoDEA neutral surfactant solution containing 2.47% lauric acid (heated as above) 39.88 32.99 7 5% CocoDEA neutral surfactant solution (45% active solution) containing 3.75% lauric acid (heated as above) and 2% KOH 36.52 30.40 8 Sample C 28.84 28.59

[0193] As indicated, maltodextrin itself (Item 1) provided a very high surface tension compared to Sample C (Item 8). In the absence of CocoDEA, the surface tension remained very high even in the presence of other components used to form the reaction product (Item 2). 5 wt% CocoDEA provided a much lower surface tension (Item 4), which increased in the presence of maltodextrin (Item 3). When other components used to form the reaction mixture (excluding maltodextrin) were combined with 5 wt% CocoDEA, the surface tension increased slightly compared to the reaction product (Items 4-7). In contrast, when all reaction components were present together in Sample C (Item 8), the surface tension was lower than that of other reaction component combinations tested. The reduced surface tension realized in the presence of the maltodextrin reaction product is particularly surprising considering that maltodextrin itself increases surface tension (Items 3 and 4).

[0194] Tables 4 and 5 show the surface tension performance of sample C at 1 gpt in water and CaCl2 / water, respectively, at various pH values ​​or CaCl2 concentrations. The surface tension of sample C decreased slightly more at more acidic pH values.

[0195] pH (H 2 O) surface tension (Da-in / cm) 1 25.05 4 27.11 7 28.25 10 28.25 14 28.64

[0196] CaCl 2 (weight%) surface tension (Da-in / cm) 0.2 28.06 2 29.27 10 27.17

[0197] Interfacial tension (IFT) measurements were performed using a hook needle syringe to form an oil droplet in water. Measurements were taken using tap water and Wolfcamp A oil and evaluated after 61 hours of equilibration. Table 6 below summarizes the IFT performance of Sample C.

[0198] Concentration (gpt) IFT (Dyne / cm) 0.5 8.57 1 7.51 2 5.48

[0199] Emulsion performance of dextran reaction products Each reaction product prepared as described above was formulated to 1 gpt and combined with East Texas Hutchison Oil #2. Subsequently, each oil mixture was emulsified, and the degree of emulsification was tracked as a function of time compared to a blank. The blank consisted of oil without additional emulsifiers. Emulsification was performed at room temperature by hand shaking 50 mL of sample and 50 mL of oil at a rate of approximately 2 times per second for 60 seconds. The emulsion was immediately poured into a graduated cylinder, and the heights of the water layer, oil layer, and remaining emulsion layer were recorded using time-lapse photography. Figures 4a through 4d show plots of the percentage emulsification rate as a function of time for East Texas Hutchison #2 oil emulsified with samples E1-E4, F1-F4, G1-G4, and H1-H4, respectively.

[0200] Figure 5 shows a plot of the percentage of deemulsified water present after 60 minutes for each dextran reaction product at various weight ratios of fatty acid to dextran. As shown, various dextran reaction products can promote emulsification or deemulsification depending on the amount of fatty acid reacting with a given amount of dextran. Series E sample (caprylic acid) provided minimal emulsification. Series F sample (lauric acid) provided strong emulsification at weight ratios of 1:10 and 1:5, but emulsification decreased significantly at low fatty acid loadings. At weight ratios of 1:1 and 1:2, caprylic acid and lauric acid provided slight emulsification, but some degree of emulsification still occurred for palmitic acid and stearic acid (Series G and Series H samples) at these weight ratios. Overall, the strongest emulsification effect was observed at a weight ratio of 1:5 for all fatty acids except caprylic acid (Series E sample).

[0201] Surface tension of dextran reaction products The surface tension performance of the dextran reaction product was measured at 1 gpt and 2 gpt as specified in Table 7 below.

[0202] Sample ST (dyne / cm) in 1 gpt ST in 2 gpt (Da-in / cm) E1 34.61 30.25 E2 34.07 29.15 E3 32.39 28.87 E4 31.95 29.00 F1 30.49 28.75 F2 29.93 27.93 F3 31.34 27.65 F4 68.20 54.71 G1 33.82 28.25 G2 28.77 27.46 G3 31.51 28.53 G4 45.76 38.04 H1 34.66 28.75 H2 33.06 28.27 H3 38.07 32.13 H4 49.97 40.98

[0203] As described, all dextran reaction products were able to lower the surface tension of CocoDEA at at least some concentrations and fatty acid loadings in a manner similar to that provided by the maltodextrin reaction products described above. At the highest fatty acid loadings (samples F4, G4, and H4), the ability to lower surface tension was significantly reduced. Thus, surface tension was adjustable depending on the molecular weight of the fatty acids and the degree of fatty acid loading.

[0204] Example 3: CocoDEA substituted with betaine surfactantSample C' was prepared in the same manner as Sample C using the procedure of Example 1A and similar reagent ratios, except that CocoDEA was substituted with a betaine (ambiionic) surfactant (SOPALEX 360 BET) and the reaction was carried out at 50°C. Table 8 summarizes the surface tension of the reaction products compared with the betaine surfactant alone.

[0205] Sample ST in 1 gpt (Da-in / cm) ST in 2 gpt (Da-in / cm) Zwitterionic surfactants 71.04 64.9 Sample C' 66.27 55.55

[0206] Replacing the neutral surfactant CocoDEA with the betaine surfactant yielded high surface tension values ​​at each test concentration. The betaine surfactant itself provided relatively high surface tension values. Surprisingly, the reaction product was able to function to somewhat reduce surface tension compared to the betaine surfactant alone.

[0207] Example 4: CocoDEA substituted with an ethoxylated alcohol neutral surfactant Sample C was prepared in the same manner as Sample C using the procedure of Example 1A and similar reagent ratios, except that CocoDEA was substituted with an ethoxylated alcohol neutral surfactant (Tomadol 1-9) and the reaction was carried out at 50°C. Table 9 summarizes the surface tension of the reaction products compared to the ethoxylated alcohol surfactant alone.

[0208] Sample ST in 1 gpt (Da-in / cm) ST in 2 gpt (Da-in / cm) Ethoxylated alcohol surfactant 46.6 39.5 Sample C" 47.4 41.9

[0209] Ethoxylated alcohol surfactants provided much higher surface tension values ​​at each test concentration than CocoDEA at similar concentrations. The reaction product combined with ethoxylated alcohol surfactants provided surface tension similar to that of ethoxylated alcohol surfactants alone.

[0210] Example 5: Reduced CocoDEA ConcentrationSample C"' was prepared in the same manner as Sample C above using the procedure of Example 1A and similar reagent ratios, except that the CocoDEA concentration was reduced to 1 / 5 (i.e., 1 wt%) of the concentration used above. Table 10 summarizes the surface tension of the reaction product compared to the reduced concentration CocoDEA surfactant solution alone.

[0211] Sample ST in 1 gpt (Da-in / cm) ST in 2 gpt (Da-in / cm) CocoDEA at 1 / 5 concentration 71.96 67.87 Sample C"' 65.84 59.05

[0212] Lowering the concentration of CocoDEA significantly increased the surface tension value. Although 5 wt% CocoDEA was present, the reaction product still reduced the surface tension compared to CocoDEA itself.

[0213] Foaming performance of dextrin reaction products Sample 1C (reaction product of maltodextrin and lauric acid) was processed into a soap formulation having the following composition: 61.1 wt% deionized water, 20.9 wt% maltodextrin / lauric acid reaction product (combined with the aqueous mixture prepared as above), 7.5 wt% cocamidopropyl betaine, 0.5 wt% glycerin, and 10.0 wt% SOPALTERIC CS (sodium cocoamphohydroxypropylsulfonate, Southern Chemical and Textile). To evaluate foaming performance side-by-side, a comparative soap formulation having the following composition was prepared: 20 wt% sodium lauryl sulfate solution in 30 wt% water, 5 wt% cocamidopropyl betaine, 0.5 wt% glycerin, 0.8 wt% NaCl, and balanced deionized water. The soap formulation contained approximately equal amounts of the maltodextrin / lauric acid reaction product and sodium lauryl sulfate.

[0214] The foaming performance of the experimental soap formulation was analyzed by comparing it with a control soap formulation using the Hart-DiGeorge Foam Test. Briefly, the Hart-DiGeorge Foam Test utilizes a wire screen placed between a funnel and a graduated cylinder. A fixed volume of foaming mixture is placed into the funnel, and the time required for the wire screen (850 μm mesh size) to be exposed is measured. The liquid level in the graduated cylinder is also measured multiple times. Therefore, foams with lower density are characterized by requiring a longer time to expose the wire screen, and a smaller amount of liquid collected in the graduated cylinder indicates a more stable foam.

[0215] To perform the Heart-DiGeorge foam test with the experimental and comparative soap formulations, a 1% active solution of each soap formulation was prepared in separate portions of 200 mL of deionized (soft) water at 25°C. The following solutions were mixed at high speed in a mixer for 1 minute. After blending was complete, the resulting foam was transferred to a funnel. The time required for the wire mesh to be exposed was measured. Additionally, the liquid level in the graduated cylinder was recorded at 1, 2, 3, 4, 5, and 14 minutes. Table 11 summarizes the Heart-DiGeorge foam test performance of the experimental and comparative soap formulations.

[0216] Comparison of soap formulations Experimental soap formulation Wire time (s) 98 91 Liquid volume - 1 min. (mL) 1 1 Liquid volume - 2 min. (mL) 1 1 Liquid volume - 3 min. (mL) 1 1 Liquid volume - 4 min. (mL) 25 1 Liquid volume - 5 min. (mL) 30 1 Liquid volume - 14 min. (mL) 125 105

[0217] Wire time data and liquid volume data are shown in the bar graph in Fig. 6. As presented, the experimental and comparison soap formulations exhibit similar foam densities by providing similar wire time performance at substantially equivalent surfactant concentrations. In contrast, the experimental soap formulation provided superior foam, as evidenced by the lower liquid volume collected in the graduated cylinder.

[0218] Replacement of ethoxylate alcohol surfactants . Under the general conditions specified above, maltodextrin in the presence of CocoDEA (C 12fatty acids) and myristic acid (C 14 A reaction product was formed by reacting a mixture of fatty acids. The reaction product was an opaque fluid, and no precipitation was observed. Similar to the specific data above, the reaction product did not provide significant emulsification of the crude oil. The reaction product was formulated at a standard concentration (sample BB), as well as at half the standard concentration and twice the standard concentration (samples AA and CC, respectively). The surface tension, interfacial tension, and contact angle values ​​for these fluids are specified in Table 12 below.

[0219] The surface tension, in-face tension, and contact angle values ​​for three dielectric friction reducing fluids containing ethoxylated alcohol surfactants are also shown in Table 12 (Dielectric Fluids 1-3).

[0220] The ethoxylated alcohol surfactants in dielectric friction reducing fluids 1-3 were replaced with an equivalent amount of reaction product obtained from the dual-concentration sample CC. The surface tension, in-plane tension, and contact angle values ​​for the modified dielectric friction reducing fluids are specified in Table 12. The modified dielectric fluids are designated as dielectric fluids 1', 2', and 3', respectively.

[0221] Sample Concentration (gpt) Surface tension (dynes / cm) Interfacial tension (dynes / cm) Contact angle (°) AA 1 28.1 1.4 20.3 2 28.0 0.6 n / d BB 1 32.7 3.4 27.2 2 29.8 1.8 n / d CC 1 40.2 7.0 39.8 2 32.8 3.8 n / d Dielectric Fluid 1 1 31.66 2.02 31.3 2 29.45 1.11 n / d Dielectric Fluid 2 1 33.96 3.17 33.7 2 30.60 2.06 n / d Dielectric Fluid 3 1 30.45 1.85 30.8 2 28.76 0.98 n / d Dielectric fluid 1' 1 28.25 0.36 29.6 2 27.79 0.27 n / d Dielectric Fluid 2' 1 30.06 0.74 33.2 2 28.14 0.56 n / d Dielectric Fluid 3' 1 28.98 0.41 28.9 2 27.79 0.30 n / d

[0222] As shown in Table 12, replacing the ethoxylated alcohol surfactant of oilfield fluid 1-3 with the reaction product of the present invention provides significantly lower surface tension and interfacial tension values ​​in each case. Surprisingly, the surface tension and interfacial tension values ​​were much lower than those of the sample CC reaction product itself. Furthermore, the friction reduction properties of dielectric fluid 1'-3' were not significantly altered from the original dielectric fluid 1-3 (data not shown).

[0223] Unless otherwise indicated, all numbers representing quantities, etc. in this specification and the related claims should be understood as being modified by the term "approximately" in all cases. Accordingly, unless otherwise indicated, the numerical parameters described in the following specification and the appended claims are approximations that may vary depending on the desired characteristics to be obtained by embodiments of the present invention. At a minimum, without attempting to limit the application of the equivalence principle to the claims, each numerical parameter should be interpreted by applying general rounding techniques in light of at least the number of reported significant figures.

[0224] One or more exemplary embodiments including various features are presented herein. For clarity, not all functions of a physical implementation are described or shown in this application. It is understood that in the development of physical embodiments including embodiments of the present invention, numerous implementation-specific decisions must be made to achieve the developer's objectives, such as system-related, business-related, government-related, and other compliances, and that these may vary depending on the implementation and at the time. While the developer's efforts may be time-consuming, such efforts will nevertheless be routine work for those skilled in the art who benefit from this disclosure.

[0225] Although various systems, compositions, tools, and methods are described herein in terms of "comprising" various components or steps, systems, compositions, tools, and methods may also be "essentially composed" or "composed" of various components or steps.

[0226] As used herein, the phrase “at least one” preceding a series of items with the terms “and” or “or” to separate any item modifies the list as a whole, rather than each member of the list (i.e., each item). The phrase “at least one of” allows for the meaning of including at least one of any one of the items and / or at least one of any combination of items and / or at least one of each item. For example, the phrases “at least one of A, B and C” or “at least one of A, B or C” mean A only, B only, or C only; a combination of A, B and C; and / or refer to at least one of A, B and C.

[0227] Accordingly, the disclosed systems, compositions, tools, and methods are well adapted to achieve the purposes and advantages mentioned, as well as unique ones. The specific embodiments disclosed above are merely illustrative, and the teachings of this disclosure may be modified and practiced in a manner that is obvious to those skilled in the art and has the benefit of the teachings of this disclosure, but differs, but is equivalent. Furthermore, no limitation is placed on the details of the structures or designs depicted herein other than those described in the claims below. Accordingly, it is evident that the specific exemplary embodiments disclosed above may be altered, combined, or modified, and that all such variations are considered within the scope of the invention. The systems, compositions, tools, and methods disclosed herein by example may be suitably practiced in the absence of any elements not specifically disclosed herein and / or any elements disclosed herein. Although systems, compositions, tools, and methods are described using terms such as "comprising," "containing," or "comprising" various components or steps, systems, tools, and methods may also be "essentially composed" or "composed" of various components and steps. All numbers and scopes disclosed above may vary to some degree. Whenever a numerical range having lower and upper limits is disclosed, any number and included range within the range are specifically disclosed. In particular, all ranges of values ​​disclosed herein (in the form, “about a to about b” or equivalently “about a to b” or equivalently “about ab”) are to be understood as follows: all numbers and ranges included in the broader range of values ​​are specified. Furthermore, terms in the claims have a plain and general meaning unless explicitly and clearly defined otherwise by the patent holder. Additionally, the indefinite articles “a” or “an” used in the claims are defined to mean one or more of the elements introduced herein. In the event of a conflict in the use of a word or term in this specification and in one or more patents or other documents incorporated by reference herein, the definition consistent with this specification shall be adopted.

Claims

Claim 1 A composition comprising a neutral surfactant or a reaction product thereof; and a reaction product of a sugar polymer and a fatty acid; wherein the sugar polymer comprises dextran, a dextrin compound, or a combination thereof, and the reaction product of the sugar polymer and the fatty acid lowers the surface tension of the neutral surfactant compared to that produced by the neutral surfactant alone at the same concentration in the composition, and mol 지방산 :mole 글루코스 단량체 A composition in which the molar ratio of fatty acids to sugar polymers in the reaction product is 0.2 or higher based on [the above]. Claim 2 A composition according to claim 1, wherein the sugar polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin. Claim 3 A composition according to claim 1, wherein the fatty acid comprises 4 to 30 carbon atoms and is a straight chain. Claim 4 In claim 1, the fatty acid is butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pellavonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melisic acid, crotonic acid, cervonic acid, linoleic acid, linolerid acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, saphenic acid, vacsenic acid, folic acid, oleic acid, pinolenic acid, stearidonic acid, eleostearic acid, elelaidic acid, gondoic acid, A composition comprising one or more fatty acids selected from the group consisting of gadoleic acid, erucic acid, eicosadienkoic acid, eicosatrienoic acid, nervonic acid, mitic acid, adrenergic acid, and combinations thereof. Claim 5 A composition according to claim 1, wherein the neutral surfactant comprises a fatty acid amide alkanolamine or a reaction product thereof. Claim 6 In claim 5, the neutral surfactant comprises cocamide diethanolamine or a reaction product thereof, in a composition. Claim 7 In paragraph 1, mol 지방산 :mole 글루코스 단량체 A composition in which the molar ratio of fatty acids to sugar polymers in the reaction product is 0.2 to 1.0 based on the above. Claim 8 A composition according to claim 1, wherein the reaction product of the sugar polymer is obtained in the presence of water and a hydroxide base. Claim 9 A composition according to claim 1, wherein the reaction product of the sugar polymer comprises a fat ester reaction product. Claim 10 The composition of claim 1, wherein the composition further comprises a zwitterionic surfactant. Claim 11 A foaming formulation, foam, personal care product, or processing fluid comprising the composition of claim 1. Claim 12 A step of heating a sugar polymer, a fatty acid, and a hydroxide base in water, wherein the sugar polymer comprises dextran, a dextrin compound, or any combination thereof; a step of obtaining a reaction product of the sugar polymer and the fatty acid in an aqueous phase; and a step of combining a neutral surfactant or a reaction product thereof with the reaction product of the sugar polymer and the fatty acid in the aqueous phase, wherein mol 지방산 :mole 글루코스 단량체 A method in which the molar ratio of fatty acids to sugar polymers in the reaction product is 0.2 or higher based on [the reference value]. Claim 13 In claim 12, the sugar polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin. Claim 14 In claim 12, the above fatty acid comprises 4 to 30 carbon atoms and is a straight chain. Claim 15 In claim 12, the method wherein the neutral surfactant comprises a fatty acid amide alkanolamine or a reaction product thereof. Claim 16 In claim 15, the method comprises a neutral surfactant comprising cocamide diethanolamine or a reaction product thereof. Claim 17 In Paragraph 12, mol 지방산 :mole 글루코스 단량체 A method in which, based on, the molar ratio of fatty acids to sugar polymers in the reaction product is 0.2 to 1.

0. Claim 18 In claim 12, the reaction product of the sugar polymer and fatty acid is formed in the presence of a neutral surfactant. Claim 19 A method according to claim 18, further comprising the steps of: forming a mixture by combining a fatty acid, a hydroxide base, and a neutral surfactant in water; heating the mixture until the fatty acid is dissolved and a homogeneous mixture is formed; and combining a sugar polymer with the homogeneous mixture. Claim 20 A method according to claim 12, further comprising the step of stirring an aqueous phase to form foam. Claim 21 A method comprising the steps of: providing a treatment fluid comprising the composition of claim 1; and introducing the treatment fluid into an underground formation. Claim 22 delete Claim 23 delete Claim 24 delete Claim 25 delete Claim 26 delete Claim 27 delete Claim 28 delete Claim 29 delete Claim 30 delete Claim 31 delete Claim 32 delete Claim 33 delete Claim 34 delete Claim 35 delete Claim 36 delete Claim 37 delete Claim 38 delete Claim 39 delete Claim 40 delete Claim 41 delete Claim 42 delete Claim 43 delete Claim 44 delete Claim 45 delete Claim 46 delete Claim 47 delete Claim 48 delete Claim 49 delete Claim 50 delete Claim 51 delete Claim 52 delete

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