Compositions containing reaction products of saccharide polymers combined with amide-based neutral surfactants and fatty acids or fatty acid esters and methods for obtaining said reaction products - Patents.com

Abstract

A composition containing the reaction product of a saccharide polymer with a fatty acid or fatty acid ester is obtained in an aqueous phase in the presence of a hydroxide base and a neutral surfactant. The saccharide polymer contains a dextrin compound or any combination thereof. The neutral surfactant may contain at least one compound having the structure: [C4] TIFF2025501136000013.tif56126 In the structural formula, R 1 is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms; R 2 is C1-C4 appropriately branched alkyl, CH2OH, CH2O(CH2CH2O) x CH2CH2OH (x is 0 or a positive integer), CH(OH)CH2OH, CO2H, or CH2SO3 - and R 3 is H or C1-C4 optionally branched alkyl, R 2 and R 3 are not simultaneously CHOH and H, respectively. The saccharide polymer reaction product may be present in the aqueous phase in a concentration effective to reduce the surface tension of the neutral surfactant.

Description

[Technical field]

[0001] The present invention relates to compositions containing the reaction product of a saccharide polymer and a fatty acid or fatty acid ester combined with an amide-based neutral surfactant, and to a method for obtaining said reaction product. [Background technology]

[0002] Amphiphilic compounds that have both hydrophobic and hydrophilic moieties in their molecular structure are commonly referred to as "surfactants" or "surfactant compounds." Surfactants, due to their molecular structure, tend to reduce the 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 other functions in these applications and others, surfactants may increase the solubility of poorly soluble substances, increase foaming, promote emulsification or demulsification, and / or reduce viscosity in certain cases.

[0003] Various conventional surfactants have drawbacks. Some common synthetic surfactants have poor biodegradability (including slow biodegradation in liquid environments) and / or poor biocompatibility, which can adversely affect consumer and industrial products and processes in which such surfactants are used. In addition, some common surfactants can be expensive, have poor water solubility, and / or be subject to environmental and governmental regulations regarding their use. Some surfactants can exhibit high surface tension values ​​at their critical micelle concentration, which can complicate fluid handling during formulation of consumer and industrial products containing such surfactants. A further drawback associated with conventional surfactants is that the hydrophilic-lipophilic balance (HLB) is fixed by the molecular structure of the particular amphiphilic compound used, and thus may not be suitable for a particular application, even if the surfactant is otherwise chemically compatible with the expected conditions of use.

[0004] As described in US Patent Publication No. 2021 / 0340429, a versatile class of surfactants may be obtained by combining the reaction products of fatty acids and saccharide polymers with alkanolamide neutral surfactants (co-surfactants). The fatty acids and their amounts may be varied to tailor the hydrophilic-lipophilic balance of the surfactant. An example of an alkanolamide neutral surfactant is cocamide diethanolamine (CocoDEA). CocoDEA is suitable for many applications, but its use may be regulated in certain industries. [Brief description of the drawings]

[0005] The following figures are included to illustrate certain aspects of the present disclosure and should not be considered as exclusive embodiments. The disclosed subject matter is capable of considerable modification, permutation, combination, and equivalents in form and function without departing from the scope of the present disclosure.

[0006] [Figure 1] FIG. 2 is a graph plotting the surface tension of the reaction product of maltodextrin and mixed fatty acids with CocoDEA as a co-surfactant as a function of time. [Diagram 2] FIG. 2 is a graph plotting the surface tension as a function of time of the reaction product of maltodextrin and mixed fatty acids combined with a co-surfactant formed from mixed fatty acids and 3-aminopentane. [Diagram 3] FIG. 1 is a graphical plot of surface tension as a function of time for the reaction product of maltodextrin and mixed fatty acids combined with a co-surfactant formed from the mixed fatty acids and 2-(2-aminoethoxy)ethanol. DISCLOSURE OF THEINVENTION

[0007] The present disclosure relates generally to surfactant technology, and more specifically to compositions containing surfactants formed from biologically sourced materials that can provide low surface tension values ​​in an aqueous phase. The compositions may promote microemulsion formation and / or may in some cases be microemulsions themselves.

[0008] As mentioned above, conventional surfactants may exhibit various problems such as high cost, lack of biodegradability, poor biocompatibility, and / or poor solubility, which may limit their application in various applications. Furthermore, there is no easy way to change the hydrophobic-lipophilic balance (HLB) of conventional surfactants, unless one develops a new synthesis of an entirely different chemical. Surface tension (interfacial tension) values ​​are also often high for some types of surfactants as well, which may complicate their handling in various applications and / or hinder their incorporation into various consumer and industrial products. In addition, some types of surfactants, especially anionic surfactants, may interact adversely with components (e.g., salts) that may be present in the fluid. Finally, certain surfactants may be subject to governmental regulations depending on the application.

[0009] Surfactant compositions containing the reaction product of a fatty acid and a saccharide polymer in combination with an alkanolamide neutral surfactant (co-surfactant) are a versatile class of surfactant compounds. Not only can the hydrophilic-lipophilic balance be easily altered by varying the type and amount of fatty acid, but surprisingly low surface tension values ​​can be achieved when the reaction product is present in combination with an alkanolamide neutral surfactant. Specifically, when the reaction product of a fatty acid or fatty acid ester and a saccharide polymer is present in combination with a suitable neutral surfactant, the surface tension may be lower than the surface tension of the neutral surfactant itself at substantially the same concentration. That is, the reaction product of a fatty acid or fatty acid ester and a saccharide polymer may synergistically interact with the neutral surfactant to reduce the surface tension value compared to the neutral surfactant alone at substantially the same concentration. As disclosed in US Patent Application Publication No. 2021 / 0340429, suitable alkanolamide neutral surfactants include cocamide diethanolamine and cocamide diisopropanolamine. While surfactant compositions containing these cosurfactants are suitable in many cases, a broader structural diversity of cosurfactants may be desirable for applications where cocamide diethanolamine and similar compounds cannot be freely used, e.g., due to government regulations.

[0010] The reaction products used in the present disclosure can be produced with adjustable additives (substituents) and amounts thereof to tailor surfactant performance (e.g., adjust HLB) for various applications when combined with an appropriate neutral co-surfactant. The reaction products can be produced by reacting a saccharide polymer, such as a dextran or dextrin compound, with a fatty acid under alkaline conditions, as described in U.S. Patent Application Publication No. 2021 / 0340429.

[0011] In addition, the present disclosure also provides a more convenient source of fatty acid that is reacted with saccharide polymer to form a reaction product according to the disclosure herein. That is, the present disclosure demonstrates that, like fatty acid, fatty acid esters can be reacted with saccharide polymers in an aqueous phase under alkaline conditions in the presence of a suitable co-surfactant to obtain compositions comprising one or more saccharide polymer reaction products that also exhibit low surface tension values ​​in the presence of a suitable co-surfactant. Advantageously, fatty acid esters (including fats and oils, such as glycerol esters of saturated and / or unsaturated fatty acids) can be obtained from less expensive sources than the corresponding free fatty acids or mixtures thereof, thereby making it possible to produce compositions with low surface tension values ​​more inexpensively than starting from the corresponding free fatty acids.

[0012] As used herein, the term "fatty acid" refers to a carboxylic acid having four or more carbon atoms, which is linear and optionally unsaturated. As used herein, the term "fatty acid ester" refers to a compound containing one or more ester moieties, which contains an alcohol component and a fatty acid component. The alcohol component may be a monohydric alcohol or a polyhydric alcohol, such as a diol or triol (e.g., glycerol). The fatty acid may be a linear, saturated or unsaturated fatty acid, examples of which are shown below.

[0013] The present disclosure further provides additional structural diversity of co-surfactants beyond the alkanolamide co-surfactant compounds described in US Patent Application Publication No. 2021 / 0340429. Advantageously, such alternative co-surfactant compounds can still achieve low surface tension values ​​in the compositions described herein. Further structural details are provided below for alternative co-surfactant compounds that may be used in conjunction with the present disclosure.

[0014] Without being limited by theory, the reaction product produced from the saccharide polymer and the fatty acid or fatty acid ester may include at least one fatty acid ester saccharide polymer formed from the reaction between the saccharide polymer (e.g., a dextran or dextrin compound) and the fatty acid component of the fatty acid or fatty acid ester, which may then synergistically interact with a neutral cosurfactant to provide low surface tension values. To form the fatty acid ester saccharide polymer, the fatty acid ester may be first hydrolyzed under alkaline conditions to produce a fatty acid component or a salt form thereof, which may then be reacted with the saccharide polymer to form at least one fatty acid ester saccharide polymer reaction product. Alternatively, the fatty acid ester may be directly transesterified with the saccharide polymer to form at least one fatty acid ester saccharide polymer reaction product. In contrast, a free fatty acid or a salt form thereof may be directly reacted with the saccharide polymer to form the saccharide polymer reaction product described herein. In the present disclosure, any one or more of the primary alcohol functional groups or secondary alcohol functional groups on the glucose monomer units of the saccharide polymer may undergo reaction to form a fatty acid ester saccharide polymer reaction product. In the process of forming the fatty acid ester saccharide polymer reaction product, the alcohol component of the fatty acid ester may be released into the aqueous phase during the formation of the fatty acid ester saccharide polymer reaction product. The alcohol component may remain with the fatty acid ester saccharide polymer reaction product in the aqueous phase or may be at least partially removed therefrom. Advantageously and surprisingly, the alcohol component released into the aqueous phase does not significantly affect the low surface tension values ​​achievable when at least one saccharide polymer reaction product and a neutral cosurfactant are present together. The alcohol component released into the aqueous phase (e.g., glycerol) may aid in the solubilization of other components of the composition and / or other components mixed with the composition to produce various consumer and industrial products.Optionally, additional glycerol may be mixed into the compositions including those made from free fatty acids or those made from fatty acid esters without significantly affecting the resulting surface tension values.

[0015] Additionally, compositions of the present disclosure that include reaction products with sufficiently high HLB values ​​may promote rapid foaming of aqueous fluids and may provide more stable foams than those provided by equivalent mass amounts of ionic surfactants, including cationic, anionic, or zwitterionic surfactants. Amphoteric surfactants may be optionally combined with compositions of the present disclosure to improve foaming performance compared to that achievable with the saccharide polymer reaction products and neutral surfactants alone. Suitable amphoteric surfactants include betaines and sultaines. Surprising benefits beyond improved foaming performance may be obtained in some cases when an amphoteric surfactant is also present. Given the biomolecular nature of the saccharide polymer reaction products, foaming or effervescent formulations containing one or more reaction products of the present disclosure may be a more environmentally conscious approach to formulating soaps and other personal care products that are intended to foam.

[0016] In addition to obtaining foaming or effervescent formulations based at least in part on neutral surfactant technology, the composition of the present disclosure may fully or partially replace more expensive surfactants and / or surfactants subject to government regulation in various industrial or consumer products.For example, the composition of the present disclosure may be an effective substitute for ethoxylated alcohol neutral surfactants.The reduction in surface tension provided by the composition described herein may also be advantageous when replacing less desirable surfactants, especially when the less desirable surfactants tend to increase surface tension values.

[0017] Thus, the reaction products of the present disclosure may be advantageous because they are bio-derived, low cost, and can reduce surface tension values ​​when present in combination with a suitable neutral co-surfactant. For example, the reaction products of maltodextrin are a particularly useful class of dextrin-based reaction products because this saccharide polymer is low cost and has a convenient molecular weight range. A variety of fatty acids with a range of molecular weights may be used to produce reaction products with a range of HLB values. Furthermore, many fats, oils, and similar glycerol esters can serve as convenient and inexpensive sources for the fatty acid esters used in forming the reaction products described herein, or the fatty acids derived therefrom. Similarly, the fats, oils, and similar glycerol esters and amounts thereof may be selected to facilitate tailoring of surfactant properties, such as, for example, modifying HLB values ​​and / or determining whether they provide emulsifying or demulsifying performance in a particular situation.

[0018] Maltodextrin represents an advantageous saccharide polymer for use in the present disclosure due to its low cost, environmentally friendly nature, and its relatively easy chemical reaction with a variety of free fatty acids or fatty acids derived from fatty acid esters (e.g., glycerol esters). Depending on the fatty acid reacted with the maltodextrin, the hydrophobic-lipophilic balance (HLB) of the reaction product may range from about 5 to about 20 or more, where known molecular contributions may be used to calculate the HLB value. Thus, the maltodextrin reaction product may be effective in forming emulsions in substantially aqueous or substantially oily fluids, and the particular fatty acid or fatty acid ester and the amount thereof are selected for reaction with the maltodextrin based on the particular conditions expected to be present in a given application.

[0019] In addition to the variation in properties provided by fatty acid size, maltodextrins can be used in a range of oligomer sizes (e.g., 3-20 glucose monomers, or up to about 25 glucose monomers) that allow for further tailoring of properties. Thus, maltodextrin reaction products may offer numerous advantages and broad applicability in a variety of applications and formulations where surfactants are commonly used, such as soaps and other personal care products. Dextran reaction products may offer similar advantages and characteristics to maltodextrin reaction products, such as the ability to achieve lower surface tension values.

[0020] Maltodextrins and other dextrin compounds suitable for use in the present disclosure may contain from 2 to about 20 glucose monomers, or up to about 25 glucose monomers, linked by α(1,4) glycosidic linkages. At least a portion of the glucose monomers are fatty acids or fatty acid esters (fatty acid salts derived therefrom, e.g., C4-C 30 Fatty Acids or C4-C 20 The fatty acid ester dextrin reaction products may form when contacted under suitable conditions with a fatty acid salt (including a salt of a fatty acid). Without being limited by theory, at least a portion of the glucose monomers in the dextrin compound may react to form a fatty acid ester dextrin compound, which may be present in the aqueous phase in combination with unreacted fatty acid salts, if desired. When formed, the fatty acid ester dextrin reaction products may occur at any hydroxyl group of the dextrin compound, including any combination of primary and / or secondary hydroxyl groups. Hydroxyl groups of neutral surfactants may undergo similar esterification reactions under the same reaction conditions.

[0021] Dextran is a saccharide polymer characterized by having predominantly α(1,6) glycosidic linkages between adjacent glucose monomers, with a limited number of glucose side chains attached to the polymer backbone via α(1,3) glycosidic linkages. The α(1,3) glycosidic linkages may introduce crosslinks between adjacent saccharide polymer chains. Depending on the biological source, the degree of branching and molecular weight of dextran may vary widely, any of which may be used in the present disclosure. At least a portion of the glucose monomers in dextran are branched with a fatty acid or fatty acid ester (a fatty acid salt derived therefrom, e.g., C4-C 30 Fatty Acids or C4-C 20 When the glucose monomers are contacted with the fatty acid salts (including salts of fatty acids) under suitable conditions, a reaction product may form. Without being limited by theory, in some embodiments, at least a portion of the glucose monomers may react to form fatty acid ester dextran, which may be present in the aqueous phase in combination with unreacted fatty acid salts, if desired. When formed, the fatty acid ester dextran reaction product may occur at any hydroxyl group of the dextran.

[0022] In some embodiments, the reaction products of the present disclosure may include dextrin compounds having 3 to about 20 glucose monomers, or up to about 25 glucose monomers, covalently linked by α(1,4) glycosidic bonds. The following formula (I) shows the general structure of dextrin compounds having only α(1,4) glycosidic bonds between adjacent glucose monomers, where the variable "a" is a positive integer ranging from 1 to about 18, thus providing 3 to about 20 glucose monomers in the dextrin backbone. For dextrin compounds containing up to 25 glucose monomers, the variable "a" may range from 1 to about 23. Although the terminal glucose units are shown in closed form, they may also be present in the corresponding reducing sugar (open chain or acyclic) form.

[0023] [ka]

[0024] Other dextrin compounds may contain only α(1,6) glycosidic linkages or a mixture of α(1,4) and α(1,6) glycosidic linkages, and such dextrin compounds may also be suitable for use in forming the reaction products of the present application. 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.

[0025] In some or other embodiments, the reaction product may include dextran obtained from any suitable source. The structure of dextran is shown below in Formula 2, but for clarity, the α(1,3) glycosidic linkages are not shown. The α(1,3) glycosidic linkages, when they occur, may be added as side chains of terminal glucose monomers to the α(1,6)-linked saccharide polymer backbone, may form crosslinks between adjacent α(1,6)-linked saccharide polymer backbones, may interrupt the α(1,6)-linked saccharide polymer backbones with α(1,3) glycosidic linkages, or any combination thereof. Depending on the source, up to about 5% of the glucose monomers may be linked by α(1,3) glycosidic linkages. Linkage by α(1,3) glycosidic linkages may occur on any glucose monomer. The numbering of the single glucose monomers is shown below in Formula 3.

[0026] [ka]

[0027] Suitable dextrans may have a molecular weight of about 1200, about 1400, about 5000 to about 50,000,000, or about 100,000 to about 20,000,000. Thus, the variable "b" may range from about 30 to about 300,000, depending on the particular dextran selected. Particularly suitable dextrans may have a molecular weight (e.g., Mn) in the range of about 1200 to about 1400, about 1100 to about 1500, about 1000 to about 100,000, about 100,000 to about 1,000,000, about 2,000,000 to about 5,000,000, or about 5,000,000 to about 50,000,000. Another suitable dextran may have a molecular weight of about 500,000 and an activity level of about 9%.

[0028] [ka]

[0029] The saccharide polymer may comprise maltodextrin according to some embodiments of the present disclosure. Maltodextrin may be characterized by its dextrose equivalent (DE) value. Dextrose equivalent is a measure of the amount of reducing sugar (e.g., glucose monomer) present in a saccharide polymer (especially dextrin) and is expressed as a percentage of dextrose. Dextrose itself has a dextrose equivalent of 100, whereas starch, which is functionally non-reducing, is defined as having a dextrose equivalent of 0. Dextrose equivalent may be calculated by dividing the molecular weight of glucose by Mn and multiplying the result by 100. A higher dextrose equivalent value is characteristic of a smaller number of covalently attached glucose monomers (a higher relative proportion of terminal reducing sugars due to a shorter polymer backbone length). Maltodextrins suitable for forming reaction products with one or more fatty acids or one or more fatty acid esters described in the present disclosure may exhibit a dextrose equivalent value ranging from 3 to about 25, or from 3 to about 20. In more specific embodiments, the dextrose equivalent value of the maltodextrin may range from about 4.5 to about 7.0, or from about 7.0 to about 10.0, or from about 9.0 to about 12.0.

[0030] According to some embodiments, maltodextrins suitable for forming the reaction product may be obtained from hydrolysis or pyrolysis of starch, specifically the amylose component of starch. For example, maltodextrins having the formula 1 may be formed by hydrolysis or pyrolysis of amylose. Alternatively, suitable dextrins may be obtained from hydrolysis or pyrolysis of the amylopectin component of starch, in which case the dextrin may contain α(1,6) glycosidic linkages if the dextrin is obtained by hydrolysis of amylopectin side chains. Starch that may provide the dextrin may be obtained from any starch source.

[0031] Thus, the reaction product of the present disclosure may contain an aqueous phase, a neutral surfactant or reaction product form thereof, and a reaction product of a saccharide polymer with a fatty acid or fatty acid ester, where the saccharide polymer contains a dextran, a dextrin compound, or any combination thereof, and where the reaction product of the saccharide polymer with a fatty acid or fatty acid ester and the reaction product form of the neutral surfactant, if present, is formed in the presence of a hydroxide base (e.g., under aqueous alkaline conditions).

[0032] The neutral surfactant may contain at least one compound having a structure defined in Formula 4.

[0033] [ka]

[0034] Referring to Chemical Formula 4, R 1 R is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms, which may be linear or, where appropriate, branched. 1 The hydrocarbyl group defining R may be derived from a fatty acid (or mixture of fatty acids) used to form the neutral surfactant of formula (IV), as described in more detail below. In a more specific embodiment, R 1 is a branched or unbranched C4-C 30 an alkyl group (preferably unbranched) or a branched or unbranched C4-C 30 The alkyl group may be an alkenyl group (preferably unbranched) and contains one or more double bonds, preferably cis double bonds. That is, R 1 unsaturated linear C4-C 30 R may be an alkyl group. 2 and R 3 is R 1 It may also be introduced from a primary amine compound that is condensed with a fatty acid containing R to form an amide bond. 2 and R 3may be H or an optionally substituted hydrocarbyl group, preferably an optionally branched optionally substituted alkyl group (including branched or unbranched alkyl groups with optional side chain heteroatom substitution or heteroatom substitution within the alkyl chain), with the proviso that R 2 and R 3 is an optionally substituted hydrocarbyl group, and the optionally substituted hydrocarbyl group is not hydroxymethyl or 1-hydroxyethyl. 2 is C1-C4 appropriately branched alkyl, CH2OH, CH2O(CH2CH2O) x CH2CH2OH (x is 0 or a positive integer, preferably x is 0, 1, 2, 3, or 4, more preferably 0, 1, 2, or 3, and even more preferably 0, 1, or 2), CH(OH)CH2OH, CO2H, or CH2SO3 - and R 3 is H or C1-C4 optionally branched alkyl. R 2 and R 3 are not simultaneously CH2OH and H, respectively. That is, R 2 and R 3 The primary amine used to introduce R is not ethanolamine. 2 is C1-C4 appropriately branched alkyl, CH2OH, CH2O(CH2CH2O) x CH2CH2OH (x is 0 or a positive integer, preferably, x is 0, 1, 2, 3, or 4, more preferably, x is 0, 1, 2, or 3, and even more preferably, x is 0, 1, or 2), or CH(OH)CH2OH, R 3 is H or C1-C4 optionally branched alkyl, provided that R 2 and R 3 are not simultaneously CH2OH and H, respectively.

[0035] Still referring to Formula 4, in some embodiments, R 2 and R 3is not simultaneously C1-C4 appropriately branched alkyl, or R 2 and R 3 are not simultaneously C1-C4 optionally branched alkyl and H, respectively.

[0036] Examples of fatty acids (or fatty acid components within fatty acid esters) that may be suitable for forming the reaction products of the present disclosure include, for example, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelabonic 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, benzoic ... acid), behenic acid, triosylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melissic acid, crotonic acid, cervonic acid, linoleic acid, linolelaidic acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, sapienic acid, vaccenic acid, paulic acid, oleic acid, pinoleic acid, stearidonic acid, eleostearic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, eicosenoic acid, eicosadienoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, nervonic acid, mead acid, adrenic acid, and the like, and any combination thereof.

[0037] The fatty acid ester has at least one alcohol component and at least one fatty acid component (one or more of the fatty acids listed above) that may be liberated under the alkaline conditions used to form the saccharide polymer reaction product. Suitable fatty acid esters for forming the reaction product are not believed to be particularly limited, provided that the fatty acid ester undergoes effective hydrolysis to release the alcohol component and one or more fatty acid components of the fatty acid ester (or the fatty acid ester that undergoes direct transesterification). Suitable fatty acids derived from the fatty acid esters for forming the reaction products of the present disclosure may be selected (by selection of an appropriate fatty acid ester containing one or more desired fatty acids) to result in a reaction product having an HLB value in a range, such as an HLB value of about 5 to about 20. Exemplary types of fatty acid esters are shown below. Fatty acids derived from fatty acid esters range from about 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 fatty acids suitable for forming the reaction product according to the disclosure herein may be saturated or unsaturated. Preferably, at least one unsaturated fatty acid, such as oleic acid, linoleic acid or linolenic acid, may be present in the reaction product, since the fatty acid ester may be sourced from a vegetable or animal oil, as further described below.

[0038] In some embodiments, the fatty acid ester used to form the reaction product may contain a glycerol ester. The glycerol ester may be subjected to alkaline hydrolysis to liberate glycerol as the alcohol component, and up to three fatty acid components per glycerol alcohol component may be liberated to undergo reaction with the saccharide polymer according to the disclosure herein. According to some embodiments of the present disclosure, the fatty acid components released from the glycerol ester may be the same or different, and / or at least one unsaturated fatty acid may be present in the fatty acid component. Thus, the compositions described herein may further include glycerol, especially when the composition includes a reaction product formed from a glycerol fatty acid ester.

[0039] Glycerol esters suitable for forming the reaction products according to the disclosure herein are not believed to be particularly limited and may include any vegetable oil, animal oil, vegetable fat, animal fat, or any combination thereof that contains one or more desired fatty acids. The glycerol esters may undergo hydrolysis or transesterification reactions in the course of forming the reaction products with the saccharide polymers. Suitable glycerol esters may be present in vegetable or animal sources such as soybean oil, grape seed oil, olive oil, palm oil, rice bran oil, safflower oil, corn oil, coconut oil, sunflower seed oil, canola oil, rapeseed oil, peanut oil, cottonseed oil, hazelnut oil, tea seed oil, linseed oil, sesame oil, acai oil, almond oil, beech nut oil, Brazil nut oil, cashew oil, macadamia nut oil, pecan oil, pine nut oil, pistachio oil, walnut oil, pumpkin seed oil, apricot oil, avocado oil, grapefruit oil, lemon oil, orange oil, mango oil, flax seed oil, fish oil, cocoa butter, hemp seed oil, castor oil, tall oil, beef tallow, buffalo tallow, sheep tallow, goat tallow, duck tallow, pork tallow, poultry tallow, and any combination thereof.

[0040] Soybean oil, for example, contains a mixture of saturated and unsaturated fatty acids, primarily palmitic, stearic, oleic, linoleic, and linolenic acids, with the majority of fatty acids available from soybean oil consisting of monounsaturated and polyunsaturated fatty acids (oleic, linoleic, and linolenic). Palm oil contains about 50% saturated fatty acids (palmitic, stearic, and myristic acids) and about 50% unsaturated fatty acids (oleic, linoleic, and linolenic acids). Coconut oil contains mainly saturated fatty acids (caprylic, capric, lauric, myristic, palmitic, and stearic acids) and less than 10% unsaturated fatty acids (oleic and linoleic acids).

[0041] When glycerol esters are used as a direct (in situ) source of fatty acid for forming the reaction product of the present disclosure, glycerol may be present in the compositions described herein. Optionally, glycerol may be at least partially removed from the aqueous phase of the composition, if desired. Otherwise, the amount of glycerol present in the composition may be determined by the amount of glycerol esters present in forming the reaction product. For example, C8-C 24In the case of glycerol esters containing fatty acids, the weight percentage of glycerol in the glycerol esters may range from about 7% to about 17% by weight, based on the total weight of the glycerol esters. Thus, the corresponding weight percentage of glycerol in the composition containing the reaction product may range from about 7.5% to about 20% by weight, as measured relative to the fatty acids derived from glycerol upon alkaline hydrolysis. Alternatively, since each glycerol ester may release one glycerol molecule upon complete hydrolysis, the weight percentage of glycerol in the composition may be substantially equal, by mass, to the weight percentage of the glycerol esters present in the reaction mixture, relative to the entire composition. However, it should be understood that additional glycerol may be added to the composition beyond that liberated upon conversion of the glycerol fatty acid esters to the reaction products formed from the saccharide polymers, or that additional glycerol may be added to the composition containing the reaction products prepared directly from the fatty acids.

[0042] Suitable hydroxide bases may include, for example, alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, or any combination thereof. There may be a stoichiometric excess or stoichiometric deficiency of the hydroxide base relative to the amount of fatty acid ester or fatty acid.

[0043] In the reaction product, the molar ratio of fatty acid or fatty acid derived from fatty acid ester to glucose monomer is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.05 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.08 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on about 0.1 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on about 0.2 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on about 0.3 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.4 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸: Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.5 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.6 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー Based on approximately 0.7 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or greater than about 0.8 based on moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー The maximum ratio of fatty acid to dextrin or dextran in the reaction product may be about 1.0 based on glucose monomers in most cases, although molar ratios greater than 1.0 are within the scope of the present disclosure. Thus, in some embodiments, the molar ratio of fatty acid to glucose monomers in the reaction product is about 0.05 molar or more. 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 1.0 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.05 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.8 moles脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.1 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.2 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Moleサッカライドポリマー中のグルコースモノマー ~ approx. 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole グルコースモノマー ~ approx. 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.3 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.4 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.4 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.4 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.4 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー or about 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー ~ approx. 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー The ratio may range from 0.1 to 0.5. The aforementioned ratios may represent the molar ratio of fatty acids (or fatty acids contained within fatty acid esters) reacted with the dextran or dextrin compound. One or more hydroxyl groups per glucose monomer may react, in some cases, especially at a molar ratio of 1.0 or more. At least a portion of the glucose monomers may remain unfunctionalized, especially at low molar ratios. Unreacted fatty acids, if present, may remain in the reaction product as fatty acid salts of hydroxide bases. Any hydroxyl groups may undergo functionalization.

[0044] Thus, the reaction product of the present disclosure may contain one or more fatty acid ester dextrins and / or one or more fatty acid ester dextran, optionally in further combination with a fatty acid salt (e.g., an alkali metal carboxylate), and / or a hydroxide base (e.g., an alkali metal hydroxide base). The hydroxide base may be present in at least a molar amount sufficient to react with at least a portion of the fatty acid ester to promote its hydrolysis and convert the fatty acid component of the fatty acid ester to a fatty acid salt (e.g., an alkali metal carboxylate). Alternatively, the hydroxide base may be present in a molar amount sufficient to form a fatty acid salt (e.g., an alkali metal carboxylate) when forming the reaction product directly from the free fatty acid. The alcohol component released from the fatty acid ester after hydrolysis may be present in combination with any reaction product as well. The hydroxide base may be neutralized with an acid or removed by washing, and the composition containing the reaction product may maintain a low surface tension after neutralization or washing. The alcohol component, if present, may likewise be at least partially removed from the composition, if desired, for example by distillation or solvent extraction.

[0045] Alternatively, other saccharide polymers may be used to form the reaction product in the composition disclosed herein.Other saccharide polymers that may be used in this regard include, but are not limited to, glycogen, guar, xanthan, welan, scleroglucan, chitosan, schizophyllan, levan, pectin, inulin, arabinoxylan, pullulan, gellan, carrageenan, chitin, cellulose, starch, or combinations thereof.Saccharide polymer fragments obtained from the above and containing about 3 to about 25 monomers per fragment may also be used to form the reaction product disclosed herein.

[0046] In some embodiments and preferably, the reaction products of the present disclosure may facilitate reducing the surface tension of the neutral surfactant identified above in Formula 4. That is, the reaction products may be present in a concentration effective to reduce the surface tension compared to the surface tension provided by a substantially comparable concentration of the neutral surfactant alone in the aqueous phase.

[0047] Neutral surfactants suitable for use in the present disclosure may be obtained by condensation of a fatty acid with a primary amine. Condensation of a fatty acid with an amine may be performed by heating the fatty acid and the amine, preferably neat, until water evolution is complete. Alternatively, a peptide coupling agent may be used. The fatty acid used to form the neutral surfactant may be any straight chain, saturated or unsaturated fatty acid. Exemplary fatty acids may include any of the same fatty acids identified above that may be used to form reaction products with saccharide polymers in accordance with the disclosure herein. Exemplary primary amines that may be reacted with a fatty acid to form a neutral surfactant include, but are not limited to, k-taurine, glycine, serine, isoserine, valinol, serinol, isoserinol, 2-(2-aminoethoxy)ethan-1-ol, 2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol, and 2-(2-(2-propoxyethoxy)ethoxy)ethan-1-amine.

[0048] In the compositions of the present disclosure, such neutral surfactants may be present in a concentration of about 20% by weight or less, about 10% by weight or less, or about 5% by weight or less, for example, from about 1% to about 10% by weight, or from about 3% to about 8% by weight, based on the total weight of the composition.

[0049] Once formed, a composition comprising a reaction product disclosed herein may have a pH in the range of about 1 to about 14, such as about 1 to about 5, about 5 to about 7, about 7 to about 9, or about 9 to about 14. After forming a reaction product according to the disclosure herein, the pH may be increased or decreased as needed. A reduction in surface tension value may result in a decrease in pH in some cases. A reduction in surface tension may also result in the presence of dissolved salts (e.g., potassium chloride).

[0050] The reaction products of the present disclosure, which may include those formed by the reaction of one or more fatty acids or one or more fatty acid esters with a dextrin compound and / or dextran, may be prepared by a process that includes heating a saccharide polymer containing dextran, a dextrin compound (e.g., a dextrin compound containing from 3 to about 20 glucose monomers or up to about 25 glucose monomers linked together by α(1,4) glycosidic linkages, such as maltodextrin), or any combination thereof, a fatty acid or fatty acid ester, a neutral surfactant, and a hydroxide base in an aqueous phase; and obtaining a reaction product of the saccharide polymer and the fatty acid ester in the aqueous phase. The neutral surfactant may have a structure defined by Formula 4, where the variable R 1 ~R 3 is further specified as above. The aqueous phase may further include glycerol, which may be derived from the fatty acid ester used to form the reaction product, and / or additional glycerol may be added separately to the reaction product. The reaction product may be present in the aqueous phase at a concentration effective to reduce the surface tension of the neutral surfactant, as measured relative to a comparable concentration of the neutral surfactant alone in the aqueous phase. For example, a 5% by weight aqueous solution of a neutral surfactant may have a higher surface tension than a composition comprising 5% by weight of a neutral surfactant in combination with a surface tension reducing amount of a reaction product of the present disclosure. Any of the reaction products of dextran or dextrin compounds may constitute saccharide polymers suitable for forming compositions with low surface tension. Heating may be performed at a temperature of about 100°C or less, for example, from about 50°C to about 80°C, from about 60°C to about 70°C, or from about 50°C to about 60°C.

[0051] In the presence of a neutral surfactant, the surface tension value of the composition of the present disclosure may be about 40 dyn / cm or less, about 38 dyn / cm or less, about 36 dyn / cm or less, about 34 dyn / cm or less, about 32 dyn / cm or less, about 30 dyn / cm or less, or about 28 dyn / cm or less. Alternatively, the surface tension value may be reduced by up to about 40%, by up to about 30%, by up to about 20%, by up to about 15%, or by up to about 10% compared to the surface tension of the neutral surfactant alone in the aqueous phase at a comparable concentration. In certain examples, the surface tension value may be reduced by an amount of about 10% to about 25%, by about 10% to about 20%, or by about 15% to about 25%, when measured compared to the surface tension of the neutral surfactant alone in the aqueous phase at substantially the same concentration as the neutral surfactant in the composition including the reaction product.

[0052] In forming the reaction product of the present disclosure, the method of the present disclosure may include combining a fatty acid or fatty acid ester, a hydroxide base, and a neutral surfactant in water to form a mixture, and heating the mixture until the fatty acid or fatty acid ester dissolves (e.g., by undergoing hydrolysis and / or by forming a fatty acid salt) to form a homogeneous mixture. A saccharide polymer may be combined with the fatty acid or fatty acid ester during this process, or the saccharide polymer may be combined with the homogeneous mixture after the homogeneous mixture is formed. Once the saccharide polymer is present in the homogeneous mixture, heating may be continued until a sufficient degree of reaction product is formed. The resulting aqueous phase may be directly utilized for further applications, after being concentrated, neutralized, or diluted as appropriate, or by further combining with additional ingredients targeted for a particular formulation. Formulations and products in which the composition of the present disclosure may be used are discussed below. In some examples, the composition may at least partially replace another surfactant (e.g., a charged surfactant) in a particular formulation. In other examples, the composition may at least partially replace an ethoxylated alcohol surfactant in a formulation.

[0053] The method of the present disclosure may further comprise the step of inducing foam formation in the aqueous phase after obtaining the reaction product in the aqueous phase, optionally after further combining the reaction product with water and / or adding additional ingredients. As used herein, the term "foam" refers to a state in which a large volume of gas is stably dispersed in a relatively small volume of liquid in the form of bubbles of various sizes. Inducing foam formation in the aqueous phase may be performed by stirring the aqueous phase in the presence of gas, such as stirring or mixing in the presence of gas, bubbling gas through the aqueous phase, or any combination thereof.

[0054] The gas suitable for forming bubbles in the presence of the reaction product is not believed to be particularly limited. Gases suitable for forming bubbles may include, but are not limited to, air, nitrogen, carbon dioxide, helium, natural gas, or any combination thereof. Aerosol propellants may also be used in some cases.

[0055] The term "foam quality" refers to the percentage of gas in a foam volume and may be calculated by dividing the total foam volume minus the liquid volume by the total foam volume. Foams formed in accordance with the disclosure herein may have a foam quality of about 10% or more, about 20% or more, about 30% or more, about 40% or more, about 50% or more, about 60% or more, about 70% or more, about 80% or more, or about 90% or more. The upper limit of foam quality may be about 99%, about 95%, about 90%, about 80%, about 70%, about 60%, or about 50%.

[0056] The effervescent or effervescent formulation of the present disclosure may contain an aqueous phase containing an aqueous carrier fluid, which is described in more detail below. An effervescent formulation (foam) is a composition into which gas has already been introduced to form foam bubbles. That is, an effervescent formulation may contain an aqueous fluid containing gas and a composition as described herein in which the gas is mixed together as a plurality of bubbles. In contrast, an effervescent formulation is a composition that is suitable for forming foam after gas is introduced, but in which foam bubbles have not yet formed until gas is introduced.

[0057] In addition to the reaction product of the present disclosure, the foaming or foaming formulation may further contain one or more additional surfactants other than the neutral surfactant that promotes low surface tension. The one or more additional surfactants may be cationic surfactants, anionic surfactants, amphoteric surfactants, neutral surfactants, or any combination thereof. The foaming or foaming formulation may also contain additional ingredients used in soaps and other personal care products, examples of which will be well known to those skilled in the art. Additional disclosure regarding industrial and consumer products, including personal care products and foaming variants thereof, which may include the compositions described herein, is described in more detail below.

[0058] The reaction products may be provided, supplied, mixed, or stored in solid or liquid form. The liquid form may be in a suitable fluid phase (e.g., an aqueous phase), which may be emulsified (including in a microemulsion form) or unemulsified depending on the particular formulation and intended use. The aqueous phase may also be foamed in some cases. As used herein, the terms "fluid" and "fluid phase" refer to both liquids and gels (including foams), including solutions, emulsions, and suspensions of the reaction products, unless otherwise indicated. Compositions including the reaction products of the present disclosure may contain an aqueous carrier fluid. Suitable aqueous carrier fluids may include, for example, fresh water, acidified water, seawater, brine (i.e., a saturated salt solution), or a salt water solution (i.e., a non-saturated salt solution). For example, a water-miscible organic co-solvent, such as ethanol or ethylene glycol, may be present in combination with the aqueous carrier fluid in some embodiments. A suitable aqueous carrier fluid may be present during formation of the reaction product, or alternatively, the aqueous carrier fluid may be introduced after formation of the reaction product. Underground processing

[0059] Recovery of hydrocarbon resources (such as oil and gas) from subterranean formations is often performed in conjunction with the introduction of one or more subterranean treatment chemicals downhole. As used herein, the terms "treat," "treatment," "treating," and grammatical equivalents refer to any compound, fluid, or combination thereof, that is introduced into a subterranean formation to achieve a desired function and / or for a desired purpose. Appropriate treatment chemicals may be selected based on the particular conditions that are present or expected to be present downhole.

[0060] The reaction products of the present disclosure, including reaction products formed from maltodextrin, other dextrin compounds, or dextran, may be formulated as subterranean processing fluids. The processing fluids may be used in various subterranean processing operations to facilitate or promote desired outcomes in subterranean formations. As used herein, the term "processing fluid" refers to any fluid used in a subterranean processing operation that involves achieving a desired function and / or a desired objective. Unless otherwise specified, the use of the term "processing fluid" does not imply any particular action by the processing fluid or its components. Examples of processing operations that may be facilitated by the use of the reaction products of the present disclosure include, but are not limited to, drilling operations, stimulation operations, production operations, remediation operations, erosion control operations, and the like, which may include, for example, fracturing operations, gravel packing operations, acidizing operations, descaling operations, consolidation operations, workover operations, cleanup operations, bypass operations, and the like. Any of these processing operations may feature emulsification, demulsification, modification of surface wetting properties downhole, or any combination thereof.

[0061] As used herein, the term "drilling operation" refers to the process of forming a well bore in a subterranean formation. As used herein, the term "drilling fluid" refers to a fluid used in drilling a well bore.

[0062] As used herein, the term "stimulation operations" refers to actions taken within a wellbore to increase production from the wellbore. As used herein, the term "stimulation fluids" refers to fluids used downhole during stimulation actions to increase production of hydrocarbon resources from a subterranean formation. In some cases, stimulation fluids may include fracturing fluids or acidizing fluids.

[0063] As used herein, the term "cleanup operation" or "damage control operation" refers to any operation to remove foreign material from a wellbore to increase production. As used herein, the term "cleanup fluid" or "damage control fluid" refers to a fluid used to remove unwanted material from a wellbore that blocks the flow of desired fluids. In one example, the cleanup fluid can be an acid treatment fluid to remove material resulting from one or more drilling treatments. In another example, the cleanup fluid can be used to remove filter cake on the wellbore wall. For example, the reaction products of the present disclosure may facilitate the liberation of hydrocarbon resources from the subterranean formation by altering the surface wetting characteristics to facilitate wellbore cleanup. In another embodiment, the treatment fluid containing the reaction products of the present disclosure may be introduced into the subterranean formation in an emulsified form and subsequently broken down (demulsified) therein to facilitate desired action within the subterranean formation. In yet another embodiment, the treatment fluid may facilitate the demulsification of fluids (e.g., emulsified hydrocarbon resources) in the downhole.

[0064] As used herein, the term "fracturing operation" refers to a high pressure operation that creates or extends multiple flow paths within a subterranean formation. As used herein, the term "fracturing fluid" refers to a fluid of increased viscosity that is used in conjunction with a fracturing operation. A number of proppant particulates may be present in the fracturing fluid to maintain the flow paths created or extended by the fracturing operation in an open condition.

[0065] As used herein, the term "remediation operation" refers to any operation designed to maintain, increase, or restore a particular production rate from a well, which may include stimulation or cleanup operations. As used herein, the term "remediation fluid" refers to any fluid used in conjunction with a remediation operation.

[0066] As used herein, the term "acid treatment operation" refers to any operation designed to remove acid soluble material from a wellbore (e.g., acid soluble material that comprises at least a portion of a subterranean formation). As used herein, the term "acid treatment fluid" refers to a fluid used during an acid treatment operation. Mineral acids (e.g., hydrochloric acid or hydrobromic acid) or organic acids may be present in compositions used in the acid treatment of carbonate formations, whereas hydrofluoric acid may be present in compositions used in the acid treatment of siliceous formations.

[0067] As used herein, the term "spotting fluid" refers to a fluid designed for localized treatment of a subterranean formation. In one example, the spotting fluid may include a lost circulation agent for treatment of a specific portion of a wellbore, such as to plug fractures and prevent sinking in the wellbore. In another example, the spotting fluid may include a water control material or a material designed to clear plugs in drilling or extraction equipment.

[0068] As used herein, the term "completion fluid" refers to fluids (including cementing compositions and cementing fluids) used during the completion stage of a well.

[0069] As used herein, the term "cementing fluid" refers to a fluid used during cementing operations in the wellbore.

[0070] The reaction products of the present disclosure may also be used in conjunction with enhanced oil recovery (EOR) operations. When used in conjunction with EOR operations, the reaction products of the present disclosure may alter surface wettability within subterranean formations to enhance recovery of hydrocarbon resources from the formations.

[0071] In any of the aforementioned treatment operations, the treatment fluid may be foamed. Foamed fracturing fluids may be advantageous, for example, in transporting proppant particulates into the wellbore, as compared to treatment fluids with increased viscosity. When foamed, the treatment fluid may have a foam quality ranging from about 1% to about 99%.

[0072] The reaction products of the present disclosure may be present in any of the treatment fluids described above. The treatment fluids of the present disclosure may be characterized by a concentration of the reaction products of about 0.1 gpt (per thousand 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 percents ranging from about 0.01% to about 1%, or about 0.01% to about 0.1%, or about 0.02% to about 0.05%. The concentrations selected may vary depending on the specific requirements for a given treatment operation and / or the unique subsurface conditions encountered downhole. In some examples, the reaction products may be present in a concentration effective to reduce the surface tension of neutral and / or amphoteric surfactants also present in the treatment fluid.

[0073] Treatment fluids including the reaction products of the present disclosure may further contain any number of additives that may be used in the oilfield service industry, as appropriate. Examples of additives that may be present in the treatment fluid in combination with the reaction products of the present disclosure include, for example, surfactants, viscosity enhancers, gelling agents, gel stabilizers, antioxidants, polymer degradation inhibitor additives, relative permeability modifiers, scale inhibitors, corrosion inhibitors, chelating agents, foaming agents, defoamers, antifoaming agents, emulsifiers, demulsifiers, iron control agents, proppants or other particulates, particulate diverters, salts, acids, fluid loss control additives, gases, catalysts, other clay control agents, dispersants, flocculants, scavengers (e.g., H2S scavengers, CO2 scavengers, or O2 scavengers), lubricants, breakers, friction reducers, crosslinkers, weighting agents, solubilizers, pH adjusters (e.g., buffers), hydrate inhibitors, caking agents, fungicides, and the like, as well as any combination thereof. Suitable examples of these additives will be known to those skilled in the art. Other Products

[0074] The composition of the present disclosure, which contains the reaction product of dextrin compounds, dextran, or any combination thereof, together with fatty acid or fatty acid ester, can be incorporated into a wide range of industrial or consumer products in which surfactants can be used.In view of the relatively favorable properties of the biomolecules present in the compositions disclosed herein, personal care products can represent the beneficial types of products in which the compositions of the present disclosure can be present.Exemplary industrial and consumer products in which the compositions can be present are further presented below.

[0075] An adjuvant is a composition used in combination with an active agent to increase the effect or potency of the active agent. In non-limiting examples, the active agent may be a pharmaceutical compound, a personal care compound, or an agricultural compound.

[0076] The compositions of the present disclosure (e.g., the dextrin compounds or reaction products of dextran and fatty acids identified above in combination with neutral or amphoteric surfactants) may be present in adjuvant compositions where various types of surfactants may be used. The compositions disclosed herein may replace surfactants used in the adjuvant composition or may be used in combination with surfactants already present in the adjuvant composition. In the adjuvant composition, the compositions may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total adjuvant composition.

[0077] The active compound may be present in the adjuvant composition, or the adjuvant composition may be applied separately from the active compound, in which case the adjuvant composition may be applied before or after the active compound.

[0078] Examples of suitable additional components that may be present in the adjuvant composition comprising the reaction product of the present disclosure include, but are not limited to, other surfactants, antifoam compounds, microparticles, metal oxides (e.g., silica, alumina, titania, zirconia, etc.), electrolytes, salts, organic solvents, wetting agents, dispersants, emulsifiers, demulsifiers, penetrants, preservatives, colorants, acids, bases, buffers, chelating agents, viscosity enhancers, thixotropic agents, stabilizers, film formers, plasticizers, antioxidants, and the like, as well as any combination thereof. Other surfactants that may be present in the adjuvant composition are not particularly limited and may include any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0079] A foaming agent is a composition in which a large volume of gas is stably dispersed in the form of bubbles of various sizes in a relatively small volume of liquid, or a composition in which bubbles can be formed by the appropriate introduction of gas (foamable formulation).

[0080] The compositions of the present disclosure (e.g., the reaction products of dextrin compounds or dextran and fatty acids in combination with neutral or amphoteric surfactants as identified above, including the combination of neutral and amphoteric surfactants in forming foam) may be present in foaming agents where various types of surfactants may be used. The compositions disclosed herein may replace surfactants used in the foaming agent or may be used in combination with surfactants already present in the foaming agent. In the foaming agent, the compositions may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total foaming agent.

[0081] The foaming agent may include any combination of cationic surfactants, anionic surfactants, amphoteric surfactants, or neutral surfactants. The compositions disclosed herein may be present in the foaming agent with any cationic surfactants, anionic surfactants, amphoteric surfactants, neutral surfactants, or any combination of two or more of these surfactants. Alternatively, the compositions disclosed herein may replace all or part of any one or more of these surfactants in the foaming agent. For example, the compositions disclosed herein may replace an anionic surfactant used in combination with an amphoteric surfactant in the foaming agent. That is, the compositions may be present in combination with one or more amphoteric surfactants in the foaming agent. The compositions may, for example, replace or be used in combination with a sulfosuccinate type surfactant in some foaming agent embodiments.

[0082] Examples of suitable additional components that may be present in the foaming agent, including 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, tertiary amines, diethanolamines, triethanolamines, ethoxylated amines, and amidoamines), foam boosters (e.g., amine oxides), solvents, water, salts, skin conditioners (e.g., ethylhexylglycerin, hydroxyethylurea, urea, panthenol, glycerin, isopropyl myristate, propylene glycol, tocopherol acetate, and polyquaternium-11), moisturizers, liquefied gases, supercritical gases, acids, bases, buffers, chelating agents, and the like, and any combination thereof. Suitable examples of these additional components will be known to those skilled in the art. Other surfactants that may be present in the foaming agent are not particularly limited and may include any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0083] Hard surface cleaners are compositions that can be used to remove a variety of materials from surfaces such as glass, metal, plastic, stone, concrete, etc. Hard surfaces that can be cleaned with hard surface cleaners include, for example, windows, counters, appliances, floors, driveways, toilets, showers and bathtubs, sinks, etc. The materials that can be removed from these types of hard surfaces are wide-ranging and include, but are not limited to, dirt, grease, soap scum, limescale and similar hard water deposits.

[0084] The compositions of the present disclosure (e.g., the dextrin compounds or reaction products of dextran and fatty acids identified above in combination with neutral or amphoteric surfactants) may be present in hard surface cleaners where various types of surfactants may be used. The compositions disclosed herein may replace surfactants used in hard surface cleaners or may be used in combination with surfactants already present in the hard surface cleaner. In hard surface cleaners, the compositions may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total hard surface cleaner.

[0085] Examples of suitable additional components that may be present in hard surface cleaners including the reaction products of the present disclosure include, but are not limited to, other surfactants, foaming compounds, antifoam compounds, salts (e.g., alkali metal carbonates), organic solvents (e.g., glycols or glycol ethers), wetting agents, dispersants, emulsifiers, demulsifiers, colorants, acids, bases, buffers, chelating agents, anti-streaking agents, alkanolamines, and the like, as well as any combination thereof. Other surfactants that may be present in the hard surface cleaners are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0086] Skin creams and lotions are compositions that may moisturize or improve the appearance of the skin. Skin creams and lotions include gels formulated for application to the skin, which may have a higher viscosity than creams or lotions.

[0087] The compositions of the present disclosure (e.g., the dextrin compounds or reaction products of dextran and fatty acids identified above in combination with neutral or amphoteric surfactants) may be present in skin creams and lotions where surfactants may be used. The compositions may replace surfactants used in the skin cream or lotion or may be used in combination with surfactants already present in the skin cream or lotion. In the skin cream or lotion, the compositions may be present in an amount of about 0.01% to about 20%, about 0.1% to about 10%, about 1% to about 15%, or about 5% to about 20% by weight of the total skin cream or lotion.

[0088] Examples of suitable additional ingredients that may be present in the skin creams or lotions disclosed herein include, but are not limited to, other surfactants, emulsifiers, essential oils, waxes, fats, solvents, viscosity enhancers, monoalcohols, diols, polyols, diol ethers and polyol ethers, milk proteins, emollients, moisturizers, skin conditioners, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, lubricants, wrinkle removers, moisturizers, radical inhibitors and other antioxidants, vitamin A, vitamin E, ceramides, fatty acids, fatty acid esters, fatty alcohols, hyaluronic acid, sodium pyroglutamic acid, glycerin, aloe vera, fragrances, colorants, sunscreens, and the like, and any combination thereof. Other surfactants that may be present in the skin creams and lotions are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants. The reaction product may replace at least a portion of one or more existing surfactants in the skin cream or lotion, or may supplement the amount of one or more existing surfactants in the skin cream or lotion.

[0089] Personal washes and shampoos are cleansing compositions formulated for application to the skin or hair. Liquid soaps for more generalized personal cleansing are similar in composition to some personal washes and shampoos and may be formulated using many of the same ingredients.

[0090] The compositions of the present disclosure (e.g., the dextrin compounds or dextran and fatty acid reaction products identified above in combination with neutral or amphoteric surfactants) may be present in body washes, shampoos, and liquid soaps where surfactants may be used. The compositions disclosed herein may replace surfactants used in body washes, shampoos, or liquid soaps, or may be used in combination with surfactants already present in the body washes, shampoos, or liquid soaps. In the body washes, shampoos, or liquid soaps, the compositions may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total body wash, shampoo, or liquid soap.

[0091] Examples of suitable additional ingredients that may be present in the personal wash, shampoo, or liquid soap disclosed herein include, but are not limited to, other surfactants, conditioners, amidoamines, fragrances, colorants, essential oils, foaming agents, humectants, fatty acids, fatty acid esters, fatty alcohols, waxes, biocides, soaps, preservatives, acids, bases, buffers, chelating agents, thickeners, vitamins, pearling agents, viscosity enhancers, moisturizers, antioxidants, sunscreens, and the like, as well as any combination thereof. Illustrative personal washes, shampoos, and liquid soaps may contain water, an effective amount of the composition (optionally further combined with another surfactant), 0-4% pearling agent, 0-1% suspending 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 personal washes, shampoos, and liquid soaps are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0092] Sunscreens are substances that can be applied to the skin to protect it from the sun. Sunscreens may be formulated as creams or in "stick" form with a suitable wax base for application to the skin.

[0093] The compositions of the present disclosure (e.g., dextrin (dextrin compound) or reaction product of dextran and fatty acid ester, as identified above, in combination with a neutral or amphoteric surfactant) may be present in sunscreens where surfactants may be used. The compositions disclosed herein may replace surfactants used in the sunscreen or may be used in combination with surfactants already present in the sunscreen. In the sunscreen, the compositions may be present in an amount of about 0.01% to about 20%, about 0.1% to about 10%, about 1% to about 15%, or about 5% to about 20% by weight of the total sunscreen.

[0094] Examples of suitable additional ingredients that may be present in the sunscreen include, but are not limited to, other surfactants, conditioners, titanium dioxide, zinc oxide, organic UV absorbers, film formers, solvents, aerosol propellants, waxes, fats, oils, moisturizers, fragrances, colorants, essential oils, fatty acids, fatty acid esters, fatty alcohols, preservatives, acids, bases, buffers, chelating agents, thickeners, insect repellents, skin conditioners, and the like, as well as any combination thereof. Other surfactants that may be present in the sunscreen are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0095] Organic UV absorbers that may be present in the sunscreen in combination with the composition include, but are not limited to, para-aminobenzoic acid, avobenzone, cinoxate, dioxybenzone, homosalate, menthyl anthranilate, octyl salicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid, sulisobenzone, trolamine salicylate, diethanolamine methoxycinnamate, digalloyl trioleate, diisobenzoxane ... trioleate), ethyl dihydroxypropyl PABA, glyceryl aminobenzoate, dihydroxyacetone containing lawsone, red petrolatum, ethylhexyl triazone, dioctyl butamide triazone, benzylidene malonate polysiloxane, terephthalidene dicamphor sulfonic acid, disodium phenyl dibenzimidazole tetrasulfonate, diethylamino hydroxybenzoyl hexyl benzoate, bis diethylamino hydroxybenzoyl benzoate, bis benzoxazolyl phenyl ethylhexyl imino triazine, drometrizole trisiloxane xanthane, methylene bisbenzotriazolyl tetramethylbutylphenol, and bisethylhexyloxyphenol methoxyphenyl triazine, 4-methylbenzylidene camphor, 4-methoxycinnamate isopentyl, phenylbenzimidazole sulfonate, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-(2-β-glucopyrano-siloxy)propoxy-2-hydroxybenzophenone, and bis-sodium phenylene-1,4-bis(2-benzimidazyl)-3,3'-5,5'-tetrasulfonate. 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-triazine5-triazine), methylene bis-benzotriazolyl tetramethylbutylphenol, 2,4,6-tris-[4-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, diethylamino hydroxybenzoyl hexyl benzoate, oxybenzone, and dihydroxydimethoxybenzophenone, and mixtures thereof.

[0096] Still other organic UV absorbers that may be 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; naphthalates; merocyanine derivatives; aminobenzophenone derivatives; dibenzoylmethane derivatives; β,β-diphenylacrylate derivatives; camphor derivatives; salicylate derivatives; anthranilate derivatives; and benzalmalonate derivatives.

[0097] In addition to formulations that are sunscreens alone, the compositions of the present disclosure may be present in sunscreens that are incorporated into other products (e.g., lotions, colognes, cosmetics, personal washes, shampoos, and the like).

[0098] Hair gels and hair sprays are preparations that can be used to hold hair in place or, if desired, to detangle hair. Hair sprays are in aerosolized form, while hair gels are thick fluids that can be applied by hand.

[0099] The compositions of the present disclosure (e.g., the reaction products of dextrin (dextrin compounds) or dextran and fatty acid esters, as identified above, in combination with neutral or amphoteric surfactants) may be present in hair sprays and hair gels where surfactants may be used. The compositions disclosed herein may replace surfactants used in hair sprays or hair gels, or may be used in combination with surfactants already present in the hair spray or hair gel. In hair sprays or hair gels, the compositions may be present in an amount of about 0.01% to about 20%, about 0.1% to about 10%, about 1% to about 15%, or about 5% to about 20% by weight of the total hair gel or hair spray.

[0100] Examples of suitable additional ingredients that may be present in hair sprays or hair gels include, but are not limited to, other surfactants, cellulosic biopolymers, water soluble polymers, polyalkylene glycols, polyalkylene glycol esters, conditioning agents, emollients, moisturizers, emulsifiers, opacifiers, thickening agents, foam stabilizers, viscosity enhancers, sequestering agents, antioxidants, antidandruff agents, suspending agents, proteins, fragrances, sunscreens, plant extracts, essential oils, fatty acids, fatty acid 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, and the like, and any combination thereof. Other surfactants that may be present in hair sprays and hair gels are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants.

[0101] One or more examples of hair sprays or hair gels may contain the compositions of the present disclosure and one or more of cetearyl alcohol, behentrimonium chloride, cyclopentasiloxane, dimethicone, ethylhexyl isononanoate, behenyl alcohol, meadowfoam oil, cyclohexasiloxane, olive fruit oil, almond oil, stearamidopropyl dimethylamine, behentrimonium methosulfate, amodimethicone, panthenol, glycol stearate, ceteth-2, hydroxyethylcellulose, phenoxyethanol, methylparaben, propylparaben, citric acid, mica, titanium dioxide, iron oxides, fragrance, or any combination thereof.

[0102] One or more examples of hair sprays or hair gels may contain the compositions of the present disclosure and one or more of cyclomethicone, jojoba esters, dimethicone copolyol, nonfat dry milk, soy protein, stearic acid, caprylic / capric / stearic triglyceride, jojoba oil, hybrid sunflower oil, cetearyl alcohol, glyceryl stearate, PEG-40 stearate, aloe vera gel, acrylates / C10-30 alkyl acrylates crosspolymer, propylene glycol, tocopheryl acetate, methylparaben, propylparaben, fragrance, or any combination thereof.

[0103] Cosmetics are preparations that can be used to change or improve appearance. Examples of cosmetics include, but are not limited to, lipstick, blusher, mascara, foundation, eyeliner, etc. Forms of cosmetics can include, for example, emulsions, creams, gels, dispersions, sticks, etc. Suitable emulsions in cosmetics can include oil-in-water or water-in-oil emulsions.

[0104] The compositions of the present disclosure (e.g., the reaction products of dextrin (dextrin compounds) or dextran and fatty acid esters, as identified above, in combination with neutral or amphoteric surfactants) may be present in various types of cosmetics where surfactants may be used. The compositions disclosed herein may replace surfactants used in cosmetics or may be used in combination with surfactants already present in the cosmetics. In cosmetics, the compositions may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total cosmetic.

[0105] Examples of suitable additional ingredients that may be present in the cosmetic include, but are not limited to, other surfactants, fragrances, preservatives, colorants, UV absorbers, moisture retaining agents, emulsifiers, gelling agents, oils, thickeners, foam stabilizers, viscosity enhancers, sequestering agents, antioxidants, suspending agents, proteins, fragrances, sunscreens, plant extracts, essential oils, fats (e.g., shea butter, mango seed butter, and cocoa butter), fatty acids, fatty acid esters, fatty alcohols, biocides, soaps, acids, bases, buffers, chelating agents, thickeners, vitamins, waxes (e.g., myristyl myristate, tea leaf extract, jojoba, sunflower seed, carnauba wax, candelilla wax, and beeswax), and the like, and any combination thereof. Some examples of ingredients that may be present in the cosmetic product may include, for example, fatty higher alcohols such as cetyl alcohol, stearyl alcohol, and behenyl alcohol; higher fatty acids, including caprylic / capric triglyceride, lauric acid, myristic acid, palmitic acid, and stearic acid; hydrocarbons, including ceresin; natural oils, including meadowfoam oil, sunflower seed oil, macadamia seed oil, green tea seed oil, ginger oil, ginseng oil, coconut oil, olive oil, and camellia oil; esters, including di(phytosteryl / octyldodecyl) lauroyl glutamate, isostearyl isostearate, methylheptyl isostearate, dicaprylyl carbonate, and isopropyl palmitate; ethers, including dicaprylyl ether; silicone oils, including dimethicone, cyclopentasiloxane, cyclohexasiloxane, phenyl trimethicone, trisiloxane, and methyl trimethicone; and hydrocarbons, including squalane. Other surfactants that may be present in the cosmetic product are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants. The cosmetic product of the present disclosure may be formulated in any suitable form, including sticks, creams, powders, gels, etc.

[0106] Deodorants and antiperspirants are formulations that can be used to control body odor. The deodorants and antiperspirants of the present disclosure may be formulated in stick, gel, powder or aerosolizable form.

[0107] The compositions of the present disclosure (e.g., the reaction products of dextrin (dextrin compounds) or dextran and fatty acid esters, as identified above, in combination with neutral or amphoteric surfactants) may be present in deodorants and antiperspirants where surfactants may be used. The compositions disclosed herein may replace surfactants used in the deodorant or antiperspirant, or may be used in combination with surfactants already present in the deodorant or antiperspirant. In the deodorant or antiperspirant, the compositions may be present in an amount of about 0.01% to about 20%, about 0.1% to about 10%, about 1% to about 15%, or about 5% to about 20% by weight of the total deodorant or antiperspirant.

[0108] Examples of suitable additional ingredients that may be present in the deodorants or antiperspirants disclosed herein include, but are not limited to, other surfactants, aluminum salts (e.g., alum, aluminum chloride, aluminum chlorohydrate, aluminum-zirconium compounds, and aluminum-zirconium tetrachlorohydrexglycine), antimicrobials, parabens, alcohols, propylene glycol, hexamethylenetetramine, acids, bases, buffers, chelating agents, fragrances, preservatives, colorants, moisture absorbents (desiccant), emulsifiers, gelling agents, oils, thickeners, foam stabilizers, viscosity enhancers, sequestering agents, antioxidants, suspending agents, fragrances, essential oils, fats, fatty acids, fatty acid esters, fatty alcohols, waxes, and the like, and any combination thereof. Other surfactants that may be present in the deodorants and antiperspirants are not particularly limited and may be any one or combination of cationic, anionic, neutral, or amphoteric surfactants. The deodorants and antiperspirants of the present disclosure may be formulated in any suitable form, including sticks, creams, powders, gels, and the like.

[0109] The compositions of the present disclosure containing the reaction product of a dextrin compound, dextran, or any combination thereof with a fatty acid ester may find exemplary uses and formulations outside the personal care area as well. In addition to the oil field applications described above, the compositions of the present disclosure may be incorporated into applications where metal sequestration from a fluid is required (e.g., during a froth flotation process). Froth flotation processes may be performed in a variety of cases, such as mining effluent treatment or water treatment. In such applications, the compositions of the present disclosure may replace surfactants used in froth flotation or may be used in combination with surfactants already present in the froth flotation process. In a given froth flotation process, the composition may be present in an amount of about 0.01% to about 20% by weight, about 0.1% to about 10% by weight, about 1% to about 15% by weight, or about 5% to about 20% by weight of the total froth flotation fluid.

[0110] In some examples, the compositions of the present disclosure may be utilized in rougher and cleaner circuits to aid in the dispersion of clay, water conditioning, additive enhancement, and / or emulsification of metal inhibitors (e.g., Mn and Fe). Any conventional foaming agent may be utilized in combination with the compositions disclosed herein. Details regarding suitable foaming agents and foaming agents will be well known to those skilled in the art.

[0111] Embodiments disclosed herein include:

[0112] A. A composition comprising a saccharide polymer reaction product with a fatty acid or fatty acid ester, the composition comprising: an aqueous phase; a neutral surfactant or reaction product thereof, the neutral surfactant comprising at least one compound having the structure:

[0113] [ka]

[0114] In the structural formula: R 1is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms; R 2 is C1-C4 appropriately branched alkyl, CH2OH, CH2O(CH2CH2O) x CH2CH2OH, CH(OH)CH2OH, CO2H, or CH2SO3 - ;R 3 is H or C1-C4 optionally branched alkyl; R 2 and R 3 are not simultaneously CHOH and H, respectively, and x is 0 or a positive integer; and a reaction product of a saccharide polymer and a fatty acid or fatty acid ester, wherein the saccharide polymer comprises a dextran, a dextrin compound, or any combination thereof, and the reaction product of the saccharide polymer and the fatty acid or fatty acid ester and the reaction product form of the neutral surfactant, when present, are formed in the presence of a hydroxide base.

[0115] A1. The composition of A, wherein the saccharide polymer comprises dextran.

[0116] A2. The composition of A, wherein the saccharide polymer comprises a dextrin compound.

[0117] B. A method for functionalizing a saccharide polymer, the method comprising: heating a saccharide polymer, a fatty acid or fatty acid ester, a neutral surfactant, and a hydroxide base in an aqueous phase, wherein the saccharide polymer contains a dextran, a dextrin compound, or any combination thereof, and the neutral surfactant contains at least one compound having the structure:

[0118] [ka]

[0119] In the structural formula: R 1is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms; R 2 is C1-C4 appropriately branched alkyl, CH2OH, CH2O(CH2CH2O) x CH2CH2OH, CH(OH)CH2OH, CO2H, or CH2SO3 - ;R 3 is H or C1-C4 optionally branched alkyl; R 2 and R 3 are not simultaneously CHOH and H, respectively, and x is 0 or a positive integer; and obtaining a reaction product of the saccharide polymer and the fatty acid or fatty acid ester in an aqueous phase, the aqueous phase also containing a neutral surfactant or a reaction product form thereof.

[0120] B1. The method of B, wherein the saccharide polymer comprises dextran.

[0121] B2. The method of B, wherein the saccharide polymer comprises a dextrin compound.

[0122] A personal care product containing the composition of A, A1 or A2.

[0123] Embodiments A, A1, A2, B, B1, and B2 may include one or more of the following further embodiments in any combination.

[0124] Element 1: The composition further contains glycerol.

[0125] Element 1A: The aqueous phase further contains glycerol.

[0126] Element 2: The reaction product is formed from fatty acid esters, and at least a portion of the glycerol is derived from the fatty acid esters.

[0127] Element 3: The fatty acid ester comprises a glycerol ester containing up to three fatty acids having from about 4 to about 30 carbon atoms.

[0128] Element 4: The reaction product of a saccharide polymer and a fatty acid or fatty acid ester is present in the aqueous phase in a concentration effective to reduce the surface tension of the neutral surfactant.

[0129] Element 5: The saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0130] Element 6: The maltodextrin has a dextrose equivalent value of about 3 to about 25.

[0131] Element 7: The molar ratio of fatty acid to saccharide polymer in the reaction product is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole サッカライドポリマー中のグルコースモノマー is about 0.2 or more based on

[0132] Element 8: The saccharide polymer reaction product comprises a fatty acid ester saccharide polymer reaction product.

[0133] Element 9:R 1 is a linear, saturated or unsaturated hydrocarbyl group.

[0134] Element 10: x is 0, 1, 2, or 3.

[0135] Element 11: A reaction product is formed from a fatty acid.

[0136] Element 11A: The reaction product is formed from a fatty acid ester.

[0137] As non-limiting examples, exemplary combinations applicable to A, A1, A2, B, B1 and B2 include: 1 or 1A, and 2; 1 or 1A, 2 and 3; 1 or 1A, and 3; 1 or 1A, and 4; 1 or 1A, and 5; 1 or 1A, 5 and 6; 1 or 1A, and 7; 1 or 1A, and 8; 1 or 1A, and 9; 1 or 1A, 9 and 10; 1 or 1A, and 11 or 11A; 11 or 11A, and 1 or 1A; 11 or 11A, and 2; 11 or 11A, and 3; 11 or 11A, and 4; 11 or 11A, and 5; 11 or 11A, Examples of such sequences include, but are not limited to, 5 and 6; 11 or 11A, and 7; 11 or 11A, and 8; 11 or 11A, and 9; 11 or 11A, 9 and 10; 2 and 3; 2 and 4; 2 and 5; 2, 5 and 6; 2 and 7; 2 and 8; 2 and 9; 2, 9 and 10; 3 and 4; 3 and 5; 3 and 6; 3 and 7; 3 and 8; 3 and 9; 3, 9 and 10; 4 and 5; 4 and 6; 4 and 7; 4 and 8; 4 and 9; 4, 9 and 10; 5 and 6; 5-7; 5 and 7; 5 and 8; 5 and 9; 5, 9 and 10; 7 and 8; 7 and 9; 7, 9 and 10; and 9 and 10.

[0138] In order to facilitate a further understanding of the disclosure herein, examples of various representative embodiments are set forth below, which should not be construed as limiting or defining the scope of the invention. Working Example

[0139] Example 1: General procedure for the preparation of maltodextrin reaction products with glycerol esters. 25.00 g of cocamide diethanolamine (CocoDEA) and 10.00 g of KOH (45% active solution) were combined in water. The reaction mixture was mechanically stirred and heated to 65°C. Soybean oil and 150.0 g of maltodextrin (MALTRIN M100, Grain Processing Corporation, Muscatine, Iowa; DE=9.0-12.0) as a 30% active solution were then added to the reaction mixture. The amount of soybean oil was selected to give a HLB of 12 or 16 upon formation of the reaction product. The amount of water was selected to give a surfactant concentration of 5 wt%, fatty acid ester (oil) concentration of 2.5 wt%, and maltodextrin concentration of 10 wt%, based on the total reactants. Once the maltodextrin was dissolved, the heat was removed and the reaction mixture was stirred until it reached room temperature. The resulting aqueous phase containing the reaction product was used without further treatment in further studies described below. Dextran reaction products may also be formed using a similar procedure.

[0140] Example 2: General procedure for preparation of maltodextrin reaction products with free fatty acids. 25.00 g of cocamide diethanolamine (CocoDEA) and 10.00 g of KOH (45% active solution) were combined in water. The reaction mixture was mechanically stirred and heated to 65°C. A fatty acid mixture containing saturated fatty acids with lauric and myristic acids as the main components and 150.0 g of maltodextrin (MALTRIN M100, Grain Processing Corporation, Muscatine, Iowa; DE=9.0-12.0) as a 30% active solution was then added to the reaction mixture. The amount of fatty acid mixture was selected to have an HLB of 12 or 16. The amount of water was selected to provide a surfactant concentration of 5 wt%, fatty acid concentration of 2.5 wt%, and maltodextrin concentration of 10 wt%, based on the total reactants. Once the maltodextrin was dissolved, the heat was removed and the reaction mixture was stirred until it reached room temperature. The resulting aqueous phase containing the reaction product was used without further treatment in further studies described below. Dextran reaction products may also be formed using a similar procedure.

[0141] General Procedure for Preparation of Neutral Surfactants. The amide-based surfactants (alternatives to CocoDEA) used in Examples 3-5 below were prepared by combining a mixture of fatty acids containing lauric and myristic acids as the major components with a slight molar excess of a primary amine (up to about 1.1 equivalents of amine per mole of carboxylic acid). A larger molar excess of the primary amine may be used if desired. The mixture was then heated neat at about 100°C until water evolution was apparently complete. The product was then analyzed by infrared spectroscopy, which confirmed the disappearance of the carboxylic acid carbonyl stretch.

[0142] Example 3: The general procedure of Example 2 was followed except that CocoDEA was replaced with an equivalent amount of a neutral surfactant prepared from a mixture of fatty acids and 3-aminopentane.

[0143] Example 4: The general procedure of Example 2 was followed except that CocoDEA was replaced with an equivalent amount of a neutral surfactant prepared from a mixture of fatty acid and 2-(2-aminoethoxy)ethanol.

[0144] Example 5: The general procedure of Example 2 was followed except that CocoDEA was replaced with an equivalent amount of a neutral surfactant prepared from a mixture of fatty acids and valinol.

[0145] Surface Tension Measurements. Surface tension (ST) measurements were performed at room temperature using a Biolin Scientific Tensiometer. The reaction products from Examples 1-5 were formulated in deionized water at concentrations of 0.5 gpt (per thousand gallons), 1 gpt and 2 gpt. The surface tension results are summarized in Table 1 below ("Table 1" consists of "Table 1-1", "Table 1-2" and "Table 1-3"). The surface tension values ​​reported were those reported by the instrument after 30 seconds of measurement. Table 1

[0146] [Table 1-1]

[0147] [Table 1-2]

[0148] [Table 1-3]

[0149] As shown in the table, both the reaction products of soybean oil (entries 1A / 1B) and mixed fatty acids (entries 2A / 2B) resulted in reduced surface tension compared to CocoDEA alone (entries 10 and 11) or CocoDEA + maltodextrin (entries 13 and 14). Surprisingly, soybean oil in most cases resulted in slightly better surface tension performance than the mixed fatty acids. This result is particularly surprising in light of the fact that the combination of mixed fatty acids and glycerol (entries 5A / 5B and 6A / 6B) resulted in surface tension values ​​equivalent to those produced with the mixed fatty acids alone (entries 2A / 2B). That is, glycerol introduced into the reaction mixture to simulate the amount (wt%) released during alkaline hydrolysis of soybean oil did not significantly affect surface tension performance, except at 0.5 gpt, where samples with added glycerol showed slightly better surface tension performance. Introducing additional glycerol beyond that released during alkaline hydrolysis of soybean oil (entries 3A / 3B and 4A / 4B) resulted in slightly higher surface tension values, which is even more surprising considering that individual reaction components tend to increase surface tension values.

[0150] The alternative co-surfactants (entries 7 to 9) similarly yielded low surface tension values ​​after 30 seconds of measurement, but not as low as those obtained when CocoDEA was used as a co-surfactant. Surface tension values ​​for entries 2A, 7 and 8 were further measured over a 5 minute period, as shown in Figures 1 to 3, respectively. As shown in the figures, the surface tension in each case decreased over time and began to reach a stable value within about 3 to 5 minutes of measurement. Samples containing CocoDEA (entry 2A) and the alternative co-surfactants of entries 7 and 8 yielded surface tension values ​​that were fairly close to each other when evaluated at longer measurement times. In contrast, the conventional surfactants reached stable surface tension values ​​much more quickly (data not shown).

[0151] Unless otherwise indicated, all numerical values ​​expressing quantities and the like in the specification and the associated claims should be understood to be modified in all instances by the term "about." Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by embodiments of the invention. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0152] One or more exemplary embodiments incorporating various features are presented herein. For clarity, not all features of a physical implementation are described or shown in this application. It is understood that in developing a physical embodiment incorporating an embodiment of the present invention, numerous implementation-specific decisions must be made to achieve the developer's goals, such as compliance with system-related, business-related, government-related, and other constraints that vary from implementation to implementation and from time to time. Although the developer's efforts may be time-consuming, such efforts would be routine for one of ordinary skill in the art and having the benefit of this disclosure.

[0153] Although various systems, compositions, means, and methods are described herein in terms of "containing" various components or steps, the systems, compositions, means, and methods can also "consist essentially of" or "consist of" the various components and steps.

[0154] As used herein, the phrase "at least one of" preceding a series of items, along with the terms "and" or "or" separating any items, modifies the list as a whole and not each member (i.e., each item) of the list. The phrase "at least one of" allows for a meaning including at least one of any of the items, and / or at least one of any combination of the items, and / or at least one of each of the items. By way of example, the phrase "at least one of A, B, and C" or "at least one of A, B, or C" refers, respectively, to A only, B only, or C only; any combination of A, B, and C; and / or at least one of each of A, B, and C.

[0155] Thus, the disclosed systems, compositions, means, and methods are well adapted to achieve the objects and advantages mentioned, as well as those inherent therein. The specific embodiments disclosed above are illustrative only, as the teachings of the disclosure may be modified and implemented in different but equivalent manners apparent to those skilled in the art having the benefit of the teachings herein. Moreover, no limitations are intended to the details of construction or design shown herein, other than as set forth in the following claims. It is therefore apparent that the specific exemplary embodiments disclosed above may be altered, combined, or modified, and all such variations are deemed to be within the scope of the present disclosure. The systems, compositions, means, and methods illustratively disclosed herein may be suitably practiced in the absence of any element not specifically disclosed herein and / or any appropriate element disclosed herein. Although the systems, compositions, means, and methods are described in terms that "contain," "include," or "comprise" various components or steps, the systems, means, and methods may also "consist essentially of" or "consist of" the various components and steps. All of the values ​​and ranges disclosed above may vary to some extent. Whenever a numerical range with a lower limit and an upper limit is disclosed, any numerical value contained within that range and any contained range is specifically disclosed. In particular, all ranges of values ​​disclosed herein (in the form of "about a to about b", or equivalently "about a to b", or equivalently "about a to b") should be understood to represent all numerical values ​​and ranges encompassed within the broader range of values. Also, the terms in the claims have their obvious ordinary meanings unless expressly and unambiguously defined by the patent owner. Moreover, the indefinite article "a" or "an" used in the claims is defined herein to mean one or more than one of the elements it introduces. In the event of any discrepancy in the use of a word or term in this specification and in one or more patents or other documents that may be incorporated herein by reference, the definition consistent with this specification should be adopted.

Claims

1. water phase; A neutral surfactant or reaction product form thereof, The neutral surfactant comprises at least one compound having the following structure: 【Chemistry 4】 In the structural formula: R １ is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms; R ２ is C １ -C ４ Optionally branched alkyl, CH ２ O.H., C.H. ２ O (CH ２ CH ２ O) ｘ CH ２ CH ２ OH, CH(OH)CH ２ OH, CO ２ H, or CH ２ SO ３ － and R ３ is H or C １ -C ４ is optionally branched alkyl; R ２ and R ３ are CH ２ is not OH or H, and x is 0 or a positive integer; A neutral surfactant or its reaction product form; and Reaction products of saccharide polymers with fatty acids or fatty acid esters A composition comprising: the saccharide polymer comprises a dextran, a dextrin compound, or any combination thereof, and the reaction product of the saccharide polymer with the fatty acid or fatty acid ester and the neutral surfactant forms in an aqueous phase in the presence of a hydroxide base, if present; composition.

2. The composition of claim 1 further comprising glycerol.

3. The composition of claim 2 , wherein the reaction product is formed from fatty acid esters, and at least a portion of the glycerol is derived from the fatty acid esters.

4. The composition of claim 3, wherein the fatty acid ester comprises a glycerol ester containing up to three fatty acids having from about 4 to about 30 carbon atoms.

5. 2. The composition of claim 1, wherein the reaction product of the saccharide polymer and the fatty acid or fatty acid ester is present in the aqueous phase at a concentration effective to reduce the surface tension of the neutral surfactant.

6. The composition of claim 1 , wherein the saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

7. The molar ratio of fatty acid to saccharide polymer in the reaction product is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mol サッカライドポリマー中のグルコースモノマー The composition of claim 1, wherein the .alpha.-methyl-.alpha.-methylphenyl.

8. The molar ratio of fatty acid to saccharide polymer in the reaction product is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mol サッカライドポリマー中のグルコースモノマー The composition of claim 1, wherein the pH is from about 0.2 to about 0.9 based on

9. The composition of claim 1 , wherein the reaction product of the saccharide polymer comprises a fatty acid ester saccharide reaction product.

10. R １ The composition of claim 1 , wherein is a linear, saturated or unsaturated hydrocarbyl group.

11. The composition of claim 1 , wherein x is 0, 1, 2, or 3.

12. A personal care product comprising the composition of claim 1.

13. heating a saccharide polymer, a fatty acid or fatty acid ester, a neutral surfactant, and a hydroxide base in an aqueous phase, wherein the saccharide polymer comprises dextran, a dextrin compound, or any combination thereof; The neutral surfactant comprises at least one compound having the following structure: 【Chemistry 4】 In the structural formula: R １ is a saturated or unsaturated hydrocarbyl group having from about 8 to about 30 carbon atoms; R ２ is C １ -C ４ Optionally branched alkyl, CH ２ O.H., C.H. ２ O (CH ２ CH ２ O) ｘ CH ２ CH ２ OH, CH(OH)CH ２ OH, CO ２ H, or CH ２ SO ３ － and R ３ is H or C １ -C ４ is optionally branched alkyl; Here, R ２ and R ３ are CH ２ heating, wherein x is not OH or H and x is 0 or a positive integer; and obtaining a reaction product of the saccharide polymer and the fatty acid or the fatty acid ester in the aqueous phase, the aqueous phase also containing the neutral surfactant or a reaction product form thereof; The method includes:

14. The method of claim 13, wherein the aqueous phase further contains glycerol.

15. 15. The method of claim 14, wherein the reaction product is formed from fatty acid esters and at least a portion of the glycerol is derived from the fatty acid esters.

16. 16. The method of claim 15, wherein the fatty acid ester comprises a glycerol ester containing up to three fatty acids having from about 4 to about 30 carbon atoms.

17. 14. The method of claim 13, wherein the saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

18. The molar ratio of fatty acid to saccharide polymer in the reaction product is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mol サッカライドポリマー中のグルコースモノマー The method of claim 13, wherein the β-amino acid is about 0.2 or more based on

19. The molar ratio of fatty acid to saccharide polymer in the reaction product is 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mol サッカライドポリマー中のグルコースモノマー The method of claim 13, wherein the pH is from about 0.2 to about 0.9 based on

20. The method of claim 13 , wherein the reaction product of the saccharide polymer comprises a fatty acid ester saccharide reaction product.

21. 14. The method of claim 13, wherein the reaction product of the saccharide polymer and the fatty acid ester is present in the aqueous phase at a concentration effective to reduce the surface tension of the neutral surfactant.

22. R １ The method of claim 13, wherein is a linear, saturated or unsaturated hydrocarbyl group.

23. 14. The method of claim 13, wherein x is 0, 1, 2, or 3.

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