Aqueous compositions containing functionalized saccharide polymers for particle dehydration and methods for particle dehydration using said aqueous compositions

Abstract

An aqueous composition containing an aqueous carrier fluid, a reaction product of a saccharide polymer and a fatty acid or fatty acid ester obtained in the presence of a hydroxide base and a neutral surfactant or its reaction product form in the aqueous carrier fluid, a zwitterionic surfactant, and, optionally, an amine-functionalized saccharide polymer, can promote dehydration of a plurality of particles. The reaction product of a saccharide polymer and a fatty acid or fatty acid ester in combination with a neutral surfactant or its reaction product form and a zwitterionic surfactant can also promote increased flux of aqueous fluid through a plurality of particles. The amine-functionalized saccharide polymer may further increase dehydration of the plurality of particles and may also improve the clarity of an aqueous filtrate obtained from the plurality of particles.

Description

[Background technology]

[0001] The present invention relates to aqueous compositions containing functionalized saccharide polymers for particle dehydration and methods for particle dehydration using the aqueous compositions.

[0002] Amphiphilic compounds that have both hydrophobic and hydrophilic moieties within their molecular structure are commonly referred to as "surfactants" or "surfactant compounds." Surfactants can be found in a wide range of consumer and industrial products, including, for example, soaps, detergents, cosmetics, pharmaceuticals, and dispersants. Additionally, surfactants are also commonly used in the oil and gas industry for both upstream and downstream applications. Depending on their molecular structure, surfactants may, for example, increase the solubility of otherwise poorly soluble substances, increase foaming, promote emulsification or demulsification, reduce viscosity, and / or alter the wetting properties of surfaces.

[0003] Various conventional surfactants have drawbacks. Some common surfactants can be expensive, have poor water solubility, be subject to environmental and / or other government regulations, and / or be incompatible with other components in aqueous fluids. Some surfactants can exhibit high surface tension values at their critical micelle concentrations, which can complicate fluid handling during formulation of consumer and industrial products containing such surfactants. A further drawback associated with conventional surfactants is that their hydrophilic-lipophilic balance (HLB) is fixed by the molecular structure of the particular amphiphilic compound used, which cannot be easily altered without developing an entirely new chemical synthesis for a different chemical entity. If the HLB of a given surfactant is ineffective for a particular application, an otherwise chemically compatible surfactant may be unsuitable for a range of anticipated use conditions.

[0004] Dewatering sand, slag, and other particulate materials is one application in which surfactants can be used. For example, U.S. Patent No. 6,797,180 provides an exemplary dewatering procedure in which a surfactant is added to a wet sand slurry to enhance its dewatering. While the presence of a surfactant may enhance dewatering, the cost and government regulations associated with many conventional surfactants remain a barrier to such dewatering processes. In addition, the fine-particle-laden aqueous fluid obtained from the dewatering process may not be suitable for discharge. Such fine-particle-laden aqueous fluids may be obtained in large quantities during the particle dewatering process, thus posing significant waste disposal and logistical challenges for handling and storage during the particle dewatering process. [Brief explanation of the drawings]

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

[0006] [Figure 1] FIG. 1 shows an exemplary reaction sequence for producing amine-functionalized dextrin compounds, particularly amine-functionalized maltodextrin compounds. [Figure 2] FIG. 2 is a graph of the flow performance (aqueous fluid uptake vs. time) of an aqueous composition through sand particles. DISCLOSURE OF THE INVENTION

[0007] The present disclosure relates generally to surfactant technology, and more specifically to aqueous compositions including surfactant blends that can promote enhanced dewatering of particulate material such as sand. In non-limiting examples, and depending on the composition, the aqueous compositions described herein may increase the flow rate of an aqueous fluid through particulate material such as sand; reduce the residual moisture content within the particulate material; reduce particulates in the aqueous fluid removed from the particulate material; or any combination thereof.

[0008] As discussed above, conventional surfactants can exhibit various problems, such as high cost, poor solubility, high surface tension values, compatibility issues, and / or excessive government regulations, which can limit their suitability for various applications. Furthermore, there is no easy way to change the hydrophobic-lipophilic balance (HLB) of conventional surfactants. These problems can be exacerbated to varying degrees when dehydrating particulate materials such as sand in the presence of surfactants.

[0009] As described in U.S. Patent Application Publication No. 2021 / 0340429, aqueous surfactant compositions containing the reaction product of a fatty acid and a saccharide polymer, such as a dextran or dextrin compound, combined with a neutral surfactant (cosurfactant), such as various fatty acid amide surfactants, constitute a versatile class of bio-sourced surfactants. Because they are most often derived from naturally occurring materials, such surfactants are considered particularly desirable when environmental or government regulations prohibit the use of other types of surfactants. Varying the type and amount of fatty acid not only facilitates altering the hydrophilic-lipophilic balance, but also allows the reaction product, when present in combination with a neutral surfactant, to achieve surprisingly low surface tension values due to the synergistic interaction of the two. Specifically, when present in combination with a suitable neutral surfactant, the reaction product of a fatty acid and a saccharide polymer can exhibit a surface tension lower than that of the neutral surfactant itself at substantially the same concentration in an aqueous fluid. Fatty acid esters may also be reacted under similar conditions in the presence of a suitable neutral surfactant to form the reaction product.

[0010] As used herein, the term "fatty acid" refers to a fatty acid having four or more carbon atoms, being straight-chained, and optionally unsaturated. As used herein, the term "fatty acid ester" refers to a compound containing one or more ester moieties, including 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 component may contain at least one or more fatty acids, which may be saturated or unsaturated, examples of which are provided below. Thus, the reaction products and aqueous compositions described herein, according to various embodiments, may be free or substantially free (e.g., less than 5% by weight or less than 1% by weight) of branched fatty acids or products formed therefrom. Thus, in various embodiments, the reaction products and aqueous compositions described herein may contain one or more fatty acids or products formed therefrom, consisting of one or more straight-chain fatty acids, which may be saturated or unsaturated.

[0011] Combining the reaction products formed from saccharide polymers and described in more detail herein with zwitterionic (amphoteric) surfactants can provide additional surprising effects and beneficial benefits. That is, the compositions briefly described above (i.e., aqueous surfactant compositions containing the reaction product of a saccharide polymer combined with a neutral surfactant or its reaction product form, e.g., a fatty acid alkanolamide) can be present in combination with a zwitterionic surfactant to promote increased flow rate of aqueous fluids through particulate matter such as sand. In addition, a reduction in residual moisture within the dehydrated particulate matter may be achieved in some cases. The increase in flow rate and the reduction in residual moisture can be measured relative to the amount obtained when a plurality of particles are contacted with water alone.

[0012] The aforementioned blend of zwitterionic surfactant and aqueous surfactant composition may provide additional advantages and surprising benefits in achieving the foregoing when present in combination with an amine-functionalized saccharide polymer. Suitable amine-functionalized saccharide polymers may include dextran polymers (dextran) or dextrin compounds in which multiple glucose units have been oxidatively opened and functionalized with at least one amine group at the oxidatively opened site. As described in U.S. Pat. Nos. 10,072,208, 10,351,770, 11,028,314, and 11,130,905, each of which is incorporated herein by reference, amine-functionalized saccharide polymers are known to promote clay stabilization during underground processing operations. Surprisingly, such amine-functionalized saccharide polymers may provide additional advantageous and surprising benefits in dehydrating particulate matter, even if not necessarily clay-based. For example, the amine-functionalized saccharide polymer may help to reduce the residual moisture content within the dehydrated particulate matter while still maintaining a rapid aqueous fluid flow rate therethrough. In addition to reducing the residual moisture content after dehydration of the particulate matter, the presence of the amine-functionalized saccharide polymer during dehydration may significantly improve the clarity of the aqueous fluid (filtrate) recovered after dehydration of the particulate matter. Without being bound by theory or mechanism, it is believed that the improved aqueous fluid clarity results from a reduction in particulate retention in the aqueous fluid when the amine-functionalized saccharide polymer is present.

[0013] Thus, in some embodiments, the aqueous composition of the present disclosure may contain an aqueous carrier fluid; a neutral surfactant or its reaction product form; a reaction product of a first saccharide polymer containing dextran, a dextrin compound, or any combination thereof, where the reaction product of the first 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 in the aqueous carrier fluid; and a zwitterionic surfactant. Optionally, an amine-functionalized saccharide polymer may optionally be present as an additional component of the aqueous composition. Thus, in some embodiments, the aqueous composition of the present disclosure may contain: an aqueous carrier fluid; a neutral surfactant or its reaction product form; a reaction product of a first saccharide polymer containing dextran, a dextrin compound, or any combination thereof, where the reaction product of the first 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 in the aqueous carrier fluid; a zwitterionic surfactant; and an amine-functionalized saccharide polymer formed from a second saccharide polymer containing a plurality of glucose units, at least a portion of which have been oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opening site. In any embodiment herein, the first saccharide polymer and / or the second saccharide polymer (if present) may contain dextran, dextrin, or any combination thereof. The first saccharide polymer and the second saccharide polymer may be the same or different. Further description of the aforementioned components in the aqueous composition of the present disclosure is provided below.

[0014] Aqueous carrier fluids suitable for use in the present disclosure may include, for example, freshwater, acidified water, seawater, brine (i.e., saturated salt solutions), or saline solutions (i.e., non-saturated salt solutions). A water-miscible organic cosolvent, such as ethanol or ethylene glycol, may be present in some embodiments in combination with the aqueous carrier fluid. The aqueous carrier fluid may disperse various components in emulsion and / or dissolved (solution) form. In more specific embodiments herein, each component within the aqueous composition may be present in dissolved form over the concentration range utilized.

[0015] Without being limited by theory, the reaction product produced from the first saccharide polymer and the fatty acid or fatty acid ester may include at least one fatty acid ester saccharide polymer reaction product formed from the reaction between the first saccharide polymer (e.g., a dextran or dextrin compound) and the fatty acid component of the fatty acid or fatty acid ester, which fatty acid ester saccharide polymer reaction product may then synergistically interact with a neutral surfactant or other components of the aqueous composition as described above. Specifically, in addition to synergizing with the neutral surfactant to provide low surface tension values, the reaction product may exhibit further synergistic benefits in combination with a zwitterionic surfactant and / or an amine-functionalized saccharide polymer to promote enhanced dewatering of particulate matter, such as sand.

[0016] To form fatty acid ester saccharide polymer reaction products from fatty acid ester starting materials, the fatty acid ester may be first hydrolyzed under alkaline conditions to produce a fatty acid moiety or its salt form, which may then be reacted with a first 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 first saccharide polymer to form at least one fatty acid ester saccharide polymer reaction product. When used, free fatty acids or their salt forms, in contrast, may be reacted directly with the first saccharide polymer to form the fatty acid ester saccharide polymer reaction products described herein. Any one or more of the primary alcohol functional groups or secondary alcohol functional groups on the glucose monomer units of the first saccharide polymer may be reacted to form fatty acid ester saccharide polymer reaction products suitable for use in the present disclosure.

[0017] During the formation of a fatty acid ester saccharide polymer reaction product from a fatty acid ester, such as an animal or vegetable oil, the alcohol component of the fatty acid ester may be released into the aqueous carrier fluid 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 carrier fluid, or may be at least partially removed therefrom. Beneficially and surprisingly, the alcohol component released into the aqueous carrier fluid does not significantly affect the low surface tension values achievable when the fatty acid ester saccharide polymer reaction product and a neutral cosurfactant are both present. The alcohol component (e.g., glycerol) released into the aqueous carrier fluid may further aid in the solubilization or dispersion of other components of the aqueous composition. Optionally, additional glycerol may be blended into the aqueous composition, including aqueous compositions made from free fatty acids and compositions made from other types of fatty acid esters where glycerol is not present. Other water-miscible alcohols may also be included as cosolvents.

[0018] 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, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, 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, sappen ... Examples of suitable fatty acids include vaccenic acid, paulic acid, oleic acid, pinolenic 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. Any of these fatty acids may be present in the aqueous compositions specified herein. The particular fatty acid and the amount thereof reacted with the first saccharide polymer may be selected, for example, to adjust the hydrophilic-lipophilic balance for a particular application.

[0019] 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 can be liberated (from a hydroxide base) under alkaline conditions in an aqueous carrier fluid and subsequently form a reaction product with the first saccharide polymer. Fatty acid esters suitable for forming reaction products with the first saccharide polymer are not considered to be particularly limited, provided that the fatty acid ester undergoes effective hydrolysis (or transesterification) to release the alcohol component and one or more fatty acid components of the fatty acid ester and facilitate the formation of the reaction product with the first saccharide polymer. Fatty acids derived from the fatty acid ester and suitable for forming the reaction product with the first saccharide polymer may be selected (by selection of a suitable fatty acid ester containing one or more desired fatty acids) to yield a saccharide polymer 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 listed below. Fatty acids derived from the fatty acid esters range from about C4 to about C6. 30 or about C4 to about C 20 or about C6 to about C 18 or about C8 to about C 24 and any one or more of which may be saturated or unsaturated. When the saccharide polymer reaction product is formed from fatty acid esters sourced from a plant or animal oil, at least one unsaturated fatty acid, such as oleic acid, linoleic acid, or linolenic acid, may be present in the saccharide polymer reaction product.

[0020] In some embodiments, the fatty acid ester used to form the saccharide polymer reaction product, such as a fatty acid ester saccharide polymer reaction product, may contain a glycerol ester. The glycerol ester may be subjected to alkaline hydrolysis to liberate glycerol as an alcohol component, and up to three fatty acid components per glycerol alcohol component may be released to undergo reaction with a first saccharide polymer in accordance with the disclosures herein. 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 among the fatty acid components. Thus, when the saccharide polymer reaction product is formed from a glycerol fatty acid ester, the aqueous composition described herein may further comprise glycerol. Alternatively, glycerol may be added to the aqueous composition as an additional component even if a glycerol ester is not used to form the saccharide polymer reaction product.

[0021] Glycerol esters suitable for forming the saccharide polymer reaction products for use in the aqueous compositions described herein are not believed to be particularly limited and may include any vegetable oil, animal oil, vegetable fat, animal fat, or any combination thereof, containing one or more desired fatty acids. The glycerol ester may undergo hydrolysis or transesterification in the course of forming the reaction product with the first saccharide polymer. Suitable glycerol esters may be found in vegetable or animal sources such as soybean oil, grapeseed 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.

[0022] For example, soybean oil contains a mixture of saturated and unsaturated fatty acids, primarily palmitic, stearic, oleic, linoleic, and linolenic acids, with the majority of fatty acids obtainable from soybean oil consisting of monounsaturated and polyunsaturated fatty acids (oleic, linoleic, and linolenic). Palm oil contains approximately 50% saturated fatty acids (palmitic, stearic, and myristic acids) and approximately 50% unsaturated fatty acids (oleic, linoleic, and linolenic acids). Coconut oil contains primarily saturated fatty acids (caprylic, capric, lauric, myristic, palmitic, and stearic acids) with less than 10% unsaturated fatty acids (oleic and linoleic acids). Specific examples of fatty acid blends that may be present in the saccharide polymer reaction products and aqueous compositions described herein include mixtures of these fatty acids. However, it should be understood that the reaction products of the present disclosure are not limited to the aforementioned blends of fatty acids.

[0023] When glycerol esters are used as a direct (in situ) source of fatty acids for the formation of the saccharide polymer reaction product, glycerol may be present in the aqueous composition. Optionally, glycerol may be at least partially or completely removed from the aqueous composition, as needed. Otherwise, the amount of glycerol present in the aqueous 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 percent of glycerol in the glycerol ester may range from about 7% to about 17% by weight, based on the total weight of the glycerol ester. Accordingly, the corresponding weight percent of glycerol in an aqueous composition containing a saccharide polymer 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, because each glycerol ester may release one glycerol molecule into the composition upon complete hydrolysis, the weight percent of glycerol in the aqueous composition may be substantially equal, by mass, to the weight percent of glycerol esters in the reaction mixture from which the saccharide polymer reaction product is formed, relative to the overall aqueous composition. Again, it should be understood that additional glycerol may be added to the aqueous composition, or at least a portion of the glycerol may be removed from the aqueous composition, depending on the specific application requirements.

[0024] In addition to or as an alternative to glycerol, one or more additional alcohols may be present in the aqueous compositions described herein, preferably one or more alcohols that are at least partially water-miscible. In a non-limiting example, the one or more additional alcohols may be one or more C1-C 12 The aqueous composition may contain a C1-C8, or C1-C4 monohydric or dihydric alcohol. Non-limiting examples of suitable alcohols may include, but are not limited to, methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, cyclopentanol, cyclohexanol, ethylene glycol, propylene glycol, and the like. When present, the one or more additional alcohols may be present in an amount of about 10% by weight or less, about 5% by weight or less, or about 2% by weight or less, based on the total weight of the aqueous composition.

[0025] Suitable hydroxide bases for forming the saccharide polymer reaction product may include, for example, alkali metal hydroxides (such as sodium hydroxide, potassium hydroxide, or any combination thereof). The hydroxide base may be present in a stoichiometric excess or stoichiometric deficiency relative to the amount of fatty acid ester or fatty acid. Thus, the aqueous composition may contain one or more fatty acid ester dextrins and / or one or more fatty acid ester dextrans, optionally further combined with a fatty acid salt (e.g., an alkali metal carboxylate) and / or a hydroxide base (e.g., an alkali metal hydroxide base). When fatty acid esters are used to form the saccharide polymer reaction product, the hydroxide base may be present in at least a molar amount sufficient to react with at least a portion of the fatty acid esters to promote their hydrolysis and convert the fatty acid components of the fatty acid esters to fatty acid salts (e.g., alkali metal carboxylates) for reaction with the first saccharide polymer. 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 saccharide polymer reaction product directly from free fatty acids. If still present after forming the saccharide polymer reaction product, excess hydroxide base may be neutralized with acid or at least partially removed by washing.

[0026] In the first saccharide polymer of the saccharide polymer 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 :mol 第1の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 :mol 第1の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 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー Based on approximately 0.2 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー Based on approximately 0.3 or more moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1の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 :mol 第1の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 :mol 第1の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 :mol 第1の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 :mol 第1の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 first saccharide polymer (e.g., dextrin compound or dextran) in the saccharide polymer 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 saccharide polymer reaction product is about 0.05 mol 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 1.0 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 mole 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー~approximately 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.4 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.9 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.8 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.7 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.6 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1の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 :mol 第1のサッカライドポリマー中のグルコースモノマー ~approximately 0.5 moles 脂肪酸もしくは脂肪酸エステル中の脂肪酸 :mol 第1のサッカライドポリマー中のグルコースモノマー The foregoing ratios may represent the molar ratio of fatty acids (or the molar ratio of fatty acids in a fatty acid ester) that reacts with the dextran or dextrin compound containing the first saccharide polymer. One or more hydroxyl groups per glucose monomer may react, in some cases, particularly at a molar ratio of about 1.0 or greater. At least a portion of the glucose monomers may react, particularly at a molar ratio of about 1.0 or greater. If the functional group is low, the unreacted fatty acid, if present, may remain in the aqueous composition as a fatty acid salt of a hydroxide base.

[0027] In various embodiments, suitable examples of the first saccharide polymer that can form the reaction product of the present disclosure include dextrin compounds, dextran, or any combination thereof. Other examples of the first saccharide polymer that can be used to form the reaction product in the aqueous composition of the present disclosure include, but are not limited to, glycogen, guar, xanthan, welan, scleroglucan, chitosan, schizophyllan, levan, pectin, inulin, arabinoxylan, pullulan, gellan, carrageenan, chitin, cellulose, starch, or any combination thereof. Saccharide polymer fragments obtained from any of the foregoing and containing about 3 to about 25 monomers per fragment can also be used to form the reaction product used in the aqueous composition. While the following description is directed primarily to dextrin compounds and dextrans and how such first saccharide polymers may form reaction products with fatty acids or fatty acid esters, it should be understood that the foregoing saccharide polymers may result in alternative reaction products in a similar manner that may also be suitable for use in the present disclosure.

[0028] Maltodextrin is one suitable dextrin compound that may be used to form the saccharide polymer reaction products of the present disclosure. Maltodextrin may be advantageous due to its low cost, environmentally friendly properties, and 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(s) reacted with maltodextrin, the hydrophobic-lipophilic balance (HLB) of the reaction product may range from about 5 to about 20 or higher, where known molecular weight contributions may be used to calculate the HLB value. In addition to the variation in properties brought about by the size and amount of fatty acid, maltodextrin is available in a variety of oligomeric sizes (e.g., 3 to 20 glucose monomers, or up to about 25 glucose monomers), potentially providing further property tuning. Thus, maltodextrin reaction products may be adapted for use under a wide range of conditions expected to exist in a given application. Reaction products formed from dextran may offer similar benefits and characteristics to those provided by maltodextrin reaction products.

[0029] Maltodextrins and other dextrin compounds suitable for use as the first saccharide polymer 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 may be linked to a fatty acid or a fatty acid ester (a fatty acid salt derived therefrom, e.g., C4-C6). 30 Fatty acids or C4-C 20The dextrin compound may form a reaction product when contacted with a fatty acid salt (including a fatty acid) under suitable conditions. 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 reaction product, which may optionally be present in combination with unreacted fatty acid salts in the aqueous compositions described herein. When formed, the fatty acid ester dextrin reaction product 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 in the aqueous carrier fluid.

[0030] Dextrans are saccharide polymers characterized by 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 dextrans can vary widely, any of which may be used in the present disclosure. At least a portion of the glucose monomers in dextrans are branched with fatty acids or fatty acid esters (fatty acid salts derived therefrom, e.g., C4-C 30 Fatty acids or C4-C 20 When the glucose monomers are contacted with a fatty acid or fatty acid ester (including a salt of a fatty acid) under suitable conditions, a reaction product can form. Without being limited by theory, in some embodiments, at least a portion of the glucose monomers may react with a fatty acid or fatty acid ester to form a fatty acid ester dextran, which may optionally be present in the aqueous composition in combination with unreacted fatty acid salts. When formed, the fatty acid ester reaction product can occur at any hydroxyl group of the dextran.

[0031] In some embodiments, the saccharide polymer reaction products in the aqueous compositions of the present disclosure may be formed from dextrin compounds having 3 to about 20 glucose monomers, or up to about 25 glucose monomers, covalently linked by α(1,4) glycosidic linkages. The following formula ("Formula 1") shows a general structure of dextrin compounds having only α(1,4) glycosidic linkages 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. While the terminal glucose units are shown in closed form in Formula 1, they may also exist in the corresponding reducing sugar (open-chain or acyclic) form.

[0032] [ka]

[0033] 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 saccharide polymer reaction products in the aqueous composition. The numbering of the single glucose monomers is shown below in Formula 2. Particularly suitable dextrin compounds have molecular weights (e.g., M) ranging from about 1200 to about 1400 or from about 1100 to about 1500. n ) may be included.

[0034] [ka]

[0035] In some or other embodiments, the saccharide polymer reaction product may be formed from a first saccharide polymer, including dextran, obtained from any suitable source. The structure of dextran is shown below, although for clarity, the α(1,3) glycosidic linkages are not depicted. When α(1,3) glycosidic linkages occur, they may be added as side chains to terminal glucose monomers on the α(1,6)-linked saccharide polymer backbone, form crosslinks between adjacent α(1,6)-linked saccharide polymer backbones, interrupt the α(1,6)-linked saccharide polymer backbone 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 via α(1,3) glycosidic linkages. Linkage via α(1,3) glycosidic linkages may occur on any glucose monomer.

[0036] [ka]

[0037] 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 have molecular weights (e.g., M) ranging from 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. n Another suitable dextran may have a molecular weight of about 500,000 and an activity level of about 9%.

[0038] As indicated above, maltodextrin may contain a first saccharide polymer when forming a reaction product in the aqueous compositions described herein. 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, while starch, which is functionally non-reducing, is defined as having a dextrose equivalent of 0. Dextrose equivalent is calculated by dividing the molecular weight of glucose by the molecular weight of M n The dextrose equivalent value can be calculated by dividing by 100 and multiplying the result by 100. A higher dextrose equivalent value is characterized by a lower number of covalently attached glucose monomers (shorter polymer backbone chain length resulting in a higher relative proportion of terminal reducing sugars). Maltodextrins suitable for forming saccharide polymer reaction products with one or more fatty acids or fatty acid esters 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, from about 7.0 to about 10.0, or from about 9.0 to about 12.0.

[0039] According to some embodiments, maltodextrins suitable for forming the saccharide polymer reaction product may be obtained from the hydrolysis or pyrolysis of starch (specifically, the amylose component of starch). For example, maltodextrins having the formula (I) may be formed by the hydrolysis or pyrolysis of amylose. Alternatively, suitable dextrin compounds may be obtained from the hydrolysis or pyrolysis of the amylopectin component of starch, in which case the dextrin compounds may contain α(1,6) glycosidic linkages if they are obtained by hydrolysis of amylopectin side chains. The starch from which the dextrin compounds are derived may be obtained from any starch source.

[0040] Thus, the saccharide polymer reaction products and related aqueous compositions described herein can be advantageous because they are substantially bio-based, low-cost, and capable of reducing surface tension when present in combination with a suitable neutral surfactant as a co-surfactant. For example, reaction products of maltodextrin can be a particularly useful class of dextrin-based reaction products because this first saccharide polymer is low-cost and in a convenient molecular weight range. A variety of fatty acids having a range of molecular weights can be used to produce saccharide polymer reaction products with a range of HLB values. Furthermore, many fats, oils, and similar glycerol esters can serve as convenient, inexpensive sources of fatty acid esters or fatty acids derived therefrom (examples of which are provided above) used in forming the saccharide polymer reaction products described herein. Similarly, fats, oils, similar glycerol esters, and other fatty acid esters, as well as the amounts thereof, can be selected to facilitate tailoring of surfactant properties, such as, for example, altering HLB values and / or performance during particle dehydration.

[0041] In some embodiments and preferably, the saccharide polymer reaction product may be formed in the presence of a neutral surfactant whose surface tension may be reduced in the presence of the saccharide polymer reaction product. Preferably, the neutral surfactant may comprise a fatty acid alkanolamide neutral surfactant. Thus, the saccharide polymer reaction product may be present in the aqueous carrier fluid at a concentration effective to reduce the surface tension of the neutral surfactant compared to the surface tension of the neutral surfactant alone at a substantially similar concentration in the aqueous carrier fluid.

[0042] At the same time, the neutral surfactant, or a form of its reaction product, may be present in the aqueous carrier fluid at a concentration effective to solubilize the saccharide polymer (first saccharide polymer) prior to forming the reaction product and the saccharide polymer reaction product itself after reaction has occurred. That is, the neutral surfactant may facilitate the formation of an aqueous composition that is an aqueous solution of the saccharide polymer reaction product. In non-limiting examples, the neutral surfactant may be present in the aqueous carrier fluid at a concentration of about 20% by weight or less, about 10% by weight or less, or about 5% by weight or less, e.g., about 1% to about 10% by weight, or about 3% to about 8% by weight, based on the total weight of the aqueous composition.

[0043] Suitable neutral surfactants may contain one or more fatty acid alkanolamide surfactants. Fatty acid alkanolamide surfactants that can reduce surface tension when combined with saccharide polymer reaction products include cocamide-based surfactants, such as cocamide diethanolamine, cocamide monoethanolamine, cocamide monoisopropanolamine, and cocamide diisopropanolamine. Cocamide diethanolamine (CocoDEA) or cocamide diisopropanolamine (CocoDIPA) may be particularly suitable neutral surfactants for use in the present disclosure. Other fatty acid amide alkanolamines (alkanolamides), such as palmitic acid amide diethanolamine, palmitic acid monoethanolamine, or palmitic acid diisopropanolamine, may also be suitable for use in the present disclosure.

[0044] Zwitterionic surfactants (also known as amphoteric surfactants) may also be present in the aqueous composition to provide synergistic behavior in combination with the saccharide polymer reaction product and the neutral surfactant. For example, the combination of the saccharide polymer reaction product, a suitable neutral surfactant, and a suitable zwitterionic surfactant may promote an increase in the flow rate of an aqueous fluid through particulate matter, such as sand, as measured relative to water alone. In addition, the combination of the saccharide polymer reaction product, a suitable neutral surfactant, and a suitable zwitterionic surfactant may reduce water retention in particulate matter, such as sand, as measured relative to water alone. In some embodiments, suitable zwitterionic surfactants for inclusion in the aqueous composition may include, for example, betaines, sultaines, amine oxides, or any combination thereof. Specific examples of suitable zwitterionic surfactants may include, for example, cocamidopropyl betaine, alkanoyl hydroxysultaines (e.g., lauryl hydroxysultaine), cocamidopropyl hydroxysultaine, alkanamidopropyl hydroxysultaines (e.g., lauramidopropyl hydroxysultaine), sodium cocoamphohydroxypropyl sulfonate, amphodiacetate, and the like.

[0045] The zwitterionic surfactant may be present in the aqueous composition in various concentrations. In non-limiting examples, one or more zwitterionic surfactants may be present in the aqueous composition at a concentration of about 25 wt % or less, about 20 wt % or less, about 15 wt % or less, about 10 wt % or less, about 5 wt % or less, about 2.5 wt % or less, about 1 wt % or less, about 0.5 wt % or less, about 0.4 wt % or less, about 0.3 wt % or less, about 0.2 wt % or less, about 0.1 wt % or less, about 0.09 wt % or less, about 0.08 wt % or less, about 0.07 wt % or less, about 0.06 wt % or less, about 0.05 wt % or less, about 0.04 wt % or less, about 0.03 wt % or less, about 0.02 wt % or less, or about 0.01 wt % or less, based on the total weight of the aqueous composition, provided that the amount of zwitterionic surfactant is not zero.

[0046] Once formed, the aqueous compositions described herein may have a pH ranging from about 1 to about 14, e.g., from about 1 to about 5, from about 5 to about 7, from about 7 to about 9, or from about 9 to about 14. After forming the saccharide polymer reaction product according to the disclosure herein, the pH may be increased or decreased as needed. Adjusting the pH may also alter the protonation state, if present, of the amine-functionalized saccharide polymer. In some cases, decreasing the pH may result in a decrease in surface tension value. A decrease in surface tension value may also result from the presence of dissolved salts, such as potassium chloride, in the aqueous carrier fluid.

[0047] Saccharide polymer reaction products (which may include those formed by the reaction of one or more fatty acids or one or more fatty acid esters with dextrin compounds and / or dextran) may be prepared by a process comprising 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 (e.g., a fatty acid alkanolamide), and a hydroxide base in an aqueous carrier fluid, and obtaining a reaction product of the saccharide polymer and the fatty acid or fatty acid ester in the aqueous carrier fluid. The aqueous carrier fluid may further comprise 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 carrier fluid at a concentration effective to reduce the surface tension of the neutral surfactant, as measured relative to a similar concentration of the neutral surfactant alone in the aqueous carrier fluid. For example, a 5 wt. % aqueous solution of the neutral surfactant may have a higher surface tension than would an aqueous composition containing 5 wt. % of the neutral surfactant in combination with the saccharide polymer reaction product present in a surface tension-reducing amount. Heating may be carried out at a temperature of up to about 100°C, e.g., 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.

[0048] The surface tension value of the aqueous 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 carrier fluid at a similar concentration. For example, the surface tension value may be reduced by 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 carrier fluid at substantially the same concentration as the neutral surfactant in the aqueous composition containing the saccharide polymer reaction product.

[0049] The amine-functionalized saccharide polymer may be prepared separately from the saccharide polymer reaction product (e.g., fatty acid ester saccharide polymer reaction product) described above before combining it therewith. The amine-functionalized saccharide polymer may be formed from a second saccharide polymer, which may be the same as or different from the first saccharide polymer. Any of the saccharide polymers (first saccharide polymers) described above as suitable for forming the saccharide polymer reaction product may similarly be used as a raw material for the second saccharide polymer used in the preparation of the amine-functionalized saccharide polymers disclosed herein. Like the saccharide polymer reaction products described above, the amine-functionalized saccharide polymers may similarly be advantageous due to the low cost of the corresponding unfunctionalized (parent) saccharide polymers, the ease of functionalizing the corresponding parent saccharide polymers, and the environmentally friendly nature of both the parent saccharide polymers and their amine-functionalized forms.

[0050] Amine-functionalized saccharide polymers, such as amine-functionalized dextrin compounds, can be prepared by oxidatively ring-opening a portion of the glucose units in the parent saccharide polymer (e.g., a dextrin compound), followed by reductive amination of at least a portion of the resulting aldehyde functional groups. Corresponding amine-functionalized dextrans can be prepared in a similar manner. Further description of amine-functionalized saccharide polymers, such as amine-functionalized dextrin compounds and amine-functionalized dextrans, and suitable functionalization methods is provided below.

[0051] In some instances, amine-functionalized dextrin compounds suitable for use in the present disclosure may include amine-functionalized maltodextrin compounds prepared by partial oxidation and reductive amination of a maltodextrin parent compound. Maltodextrin parent compounds with varying oligomeric sizes (e.g., 3 to 20 glucose monomers, or up to about 25 glucose monomers) may allow for some tailoring of the resulting properties, according to the present disclosure, by selection of the dextrin backbone chain length and the amine functionalization thereon. Amine-functionalized dextrans may be prepared by methods similar to those used to prepare amine-functionalized dextrin compounds, such as amine-functionalized maltodextrins.

[0052] Suitable amine-functionalized dextrin compounds may be prepared from a second saccharide polymer that is a dextrin compound by a process comprising: providing a dextrin compound containing 3 to about 20 glucose units linked together by α(1,4) glycosidic linkages; reacting the dextrin compound with a periodate compound to oxidatively open a portion of the glucose units to form a dialdehyde intermediate; and reacting an amine compound containing a primary or secondary amine group with the dialdehyde intermediate under reductive amination conditions to covalently bond at least one amine group at one or more of the oxidative ring-opened sites. After completion of the reductive amination reaction, at least one secondary or tertiary amine group is covalently attached to the site of oxidative ring-opening (i.e., the carbon atom formerly containing the aldehyde group). Any aldehyde groups that do not undergo imine formation are instead reduced to a primary alcohol under reductive amination conditions. Any of the above maltodextrins may represent a suitable dextrin parent compound to undergo functionalization by sequential oxidation and reductive amination in accordance with the present disclosure. Other amine-functionalized dextrins having α(1,6) glycosidic linkages may be formed by a similar process from a suitable dextrin parent compound.

[0053] Figure 1 shows an exemplary reaction sequence for producing amine-functionalized dextrin compounds, particularly amine-functionalized maltodextrin compounds. For clarity, only a single glucose unit is shown undergoing functionalization according to Figure 1 ; however, it should be understood that any number and arrangement of glucose units may undergo oxidative ring-opening and reductive amination in a manner consistent with the present disclosure. Furthermore, the number of glucose units shown in Figure 1 is exemplary and not limiting. While Figure 1 illustrates the introduction of a single amine group at the oxidative ring-opening site, it should be recognized that in some instances, both carbon atoms at the oxidative ring-opening site may undergo functionalization. Furthermore, some of the oxidative ring-opening sites may not be susceptible to functionalization with an amine group in some cases, in which case two primary alcohol groups may be present after reduction. Other amine-functionalized dextrin compounds may also be formed in a similar manner using a suitable dextrin and a suitable primary or secondary amine.

[0054] Similarly, amine-functionalized dextrans suitable for use in the present disclosure may also be functionalized using procedures similar to those shown in Figure 1. For the sake of brevity, similar functionalization of dextrans with amines will not be discussed in further detail herein.

[0055] As shown in FIG. 1, a portion of the glucose units in the parent dextrin compound (or parent dextran) may undergo oxidative ring-opening in the presence of a periodate compound to form a dialdehyde intermediate derived from the glucose monomer unit. The glycosidic bond in the parent dextrin compound is preserved after oxidative ring-opening in this manner. In more specific embodiments of the present disclosure, the periodate compound may be sodium periodate. In even more specific embodiments, the periodate compound may be reacted with the parent dextrin compound in water at a temperature ranging from about −10° C. to about 25° C. A mixture of water and a water-miscible organic solvent may be used, provided that the water-miscible organic solvent is non-reactive with periodate. Similar synthetic details apply to the subsequent oxidation of dextran for amine functionalization.

[0056] After forming the dialdehyde intermediate, a primary or secondary amine may be reacted with at least one of the aldehyde groups to form an imine intermediate (intermediate not shown in Figure 1). Typically, rather than isolating the imine intermediate, it is reacted in situ with a reducing agent to form a secondary or tertiary amine group covalently attached directly to the dextrin compound at the oxidative ring-opening site (i.e., one of the original aldehyde carbon atoms at a given oxidative ring-opening site). One or both of the aldehyde groups at a given oxidative ring-opening site may undergo imine formation and subsequent reduction. Any aldehyde group that does not undergo imine formation and subsequent reduction to form a covalently attached amine (including oxidative ring-opening sites that have not reacted with an amine at all) is instead reduced to a primary alcohol group at the oxidative ring-opening site. Thus, in some embodiments, amine-functionalized dextrin compounds, particularly amine-functionalized maltodextrin compounds, may have a primary alcohol (on the 1-carbon atom) and a secondary or tertiary amine (on the 2-carbon atom) at the oxidative ring-opening sites on the dextrin backbone. Optionally, at least some of the oxidative ring-opening sites may remain unfunctionalized with amines and instead contain two primary alcohol groups. Alternatively, the amine-functionalized dextrin compound may have secondary or tertiary amines on both carbon atoms at the oxidative ring-opening sites. Dextran may also be oxidized and functionalized with amines in a similar manner.

[0057] In a more specific embodiment, the reducing agent for reductive amination may be sodium borohydride or a similar mild reducing agent. The solvent for imine formation and subsequent reduction may be, for example, water or a mixture of water and alcohol, and the reaction may be carried out at a temperature of about -10°C to about 25°C. Similar synthetic details apply when functionalizing dextran by reductive amination. Other suitable conditions for reductive amination will be known to those skilled in the art.

[0058] As mentioned above, suitable amines for reacting with the dialdehyde intermediate are primary or secondary amines. Primary amines result in the formation of secondary amines following reductive amination, and secondary amines result in the formation of tertiary amines following reductive amination. Suitable amines may also exhibit a variety of structures and may be selected from entities including primary monoamines, secondary monoamines, diamines, triamines and other polyamines, amino alcohols, amino acids, and the like. Particularly suitable amines may include, but are not limited to, methylamine, dimethylamine, methylethylamine, ethylamine, diethylamine, propylamine, butylamine, hexylamine, octylamine, ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetraamine, ethanolamine, 2-aminopropanol, 1-amino-2-propanol, diethanolamine, and the like. When multiple amine groups are present in an amine, e.g., a diamine such as ethylenediamine, the first amine group of the diamine may be covalently bonded directly to a carbon atom at a given oxidative ring-opening site, and the second amine group of the diamine may be unbonded to a carbon atom at the oxidative ring-opening site. That is, the second amine group is not covalently bonded directly to the oxidative ring-opening site, but is instead tethered to the first amine group by a carbon-containing spacer group. The second amine group may optionally be further functionalized. Alternatively, the second amine group may also, in some cases, facilitate at least some crosslinking, where the second amine group may be covalently bonded to different oxidative ring-opening sites. Such crosslinking may be intermolecular (between different saccharide polymer chains) or intramolecular (within the same saccharide polymer chain).

[0059] In further specific embodiments, suitable amine-functionalized maltodextrin compounds within the aqueous compositions of the present disclosure may have structures defined by Formulas 4-6 below, where one covalently attached amine group is shown at each site of oxidative ring-opening. As discussed above, it should be understood that in some embodiments, two covalently attached amine groups may be present (structures not shown). Furthermore, as also discussed above, it should be understood that not all oxidative ring-opening sites are necessarily amine-functionalized and / or not all glucose monomer units undergo oxidative ring-opening. Any combination of terminal glucose units (rings A and C in Formulas 4-6) and non-terminal glucose units (ring B in Formulas 4-6) of the parent dextrin compound may undergo oxidative ring-opening and amine functionalization in accordance with the disclosure herein. While Formulas 4-6 show a single oxidized glucose unit per dextrin molecule, it should be understood that multiple oxidized glucose units and amine-functionalized glucose units may be present and arranged in any combination, and potential monomer locations for oxidation and amine functionalization are exemplified by those shown in Formulas 4-6. That is, certain amine-functionalized dextrin compounds of the present disclosure may be characterized by any arrangement of oxidized or non-oxidized A rings, oxidized or non-oxidized B rings (1-18 total, or up to 23 total), and oxidized or non-oxidized C rings, all linked together by α(1,4) glycosidic bonds.

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] In Chemical Formulas 4 to 6, R 1 and R 2 may be the same or different and may be independently selected from H, alkyl and aryl groups, provided that R 1 and R 2 and R are not both H. According to more specific embodiments, R is an alkyl or aryl group. 1 and R 2 may be optionally substituted (e.g., having a heteroatom functionality such as a second amine group), branched or linear, and / or cyclic or acyclic.

[0064] Amine-functionalized dextrin compounds suitable for use in the present disclosure may be characterized in that about 5% to about 80% of the glucose monomer units are oxidatively ring-opened. In more specific embodiments, about 10% to about 50% of the glucose monomer units in the amine-functionalized dextrin compound may be oxidatively ring-opened. In the present disclosure, any of the oxidative ring-opening sites may undergo amine functionalization, up to and including the complete amine-functionalization of all oxidative ring-opening sites. Thus, the percentage of glucose monomer units having amine functionalization may be about 80% or less, or about 50% or less, e.g., about 5% to about 80%, about 10% to about 50%, or about 5% to about 30%.

[0065] Amine-functionalized dextrans suitable for use in the present disclosure may have structures corresponding to Formulas 7-9 below, where one covalently attached amine group is shown at each site of oxidative ring-opening. It should be understood that in some embodiments, two covalently attached amine groups may be present (structures not shown). Furthermore, it should be understood that not all oxidative ring-opening sites are necessarily amine-functionalized, and / or not all glucose monomer units undergo oxidative ring-opening. Any combination of terminal glucose units (rings A and C in Formulas 7-9) and non-terminal glucose units (ring B in Formulas 7-9) of the parent dextran may undergo oxidation and amine-functionalization in accordance with the disclosure herein. Furthermore, while Formulas 7-9 show a single oxidized glucose unit per dextran polymer chain, it should be understood that multiple oxidized glucose units and amine-functionalized glucose units may be present and arranged in any combination, and potential monomer locations for oxidation are exemplified by those shown in Formulas 7-9. That is, certain amine-functionalized dextrans of the present disclosure may be characterized by any arrangement and number of oxidized or non-oxidized A rings, oxidized or non-oxidized B rings (totaling about 5,000-300,000 glucose monomers), and oxidized or non-oxidized C rings, all linked together by α(1,6) glycosidic bonds. As with the non-functionalized dextran of Formula 3, the α(1,3)-linked glucose side chains are not depicted in Formulas 7-9 for clarity. The variable R 1 and R 2 is defined above. The rate of oxidative ring-opening and amine functionalization may be similar to that described above for the amine-functionalized maltodextrin.

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] The above-described aqueous composition may be used in conjunction with the dehydration of a plurality of particles in the present disclosure. Depending on the aqueous composition used, the aqueous composition may promote an increase in the aqueous fluid flow rate through the plurality of particles, measured relative to water, and / or may reduce the residual moisture content remaining in the plurality of particles after dehydration. In addition, the clarity of the filtrate removed from the plurality of particles may sometimes be improved, which is believed to be due to the reduced generation of fine particles during the dehydration process.

[0070] Thus, the disclosed method may include providing an aqueous composition containing: an aqueous carrier fluid; a neutral surfactant or a reaction product form thereof; a reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, wherein the first saccharide polymer contains dextran, a dextrin compound, or any combination thereof, and the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester and the reaction product form of the neutral surfactant, if present, are formed in the presence of a hydroxide base in the aqueous carrier fluid; and a zwitterionic surfactant; contacting the aqueous composition with a plurality of particles; and removing the aqueous composition from the plurality of particles. The aqueous composition may increase dehydration of the plurality of particles compared to water, increase the flow rate through the plurality of particles compared to water, or any combination thereof. In some embodiments, the aqueous composition contacted with the plurality of particles may further contain an amine-functionalized saccharide polymer, the amine-functionalized saccharide polymer being prepared from a second saccharide polymer containing a plurality of glucose units in which at least a portion of the glucose units have been oxidatively ring-opened and functionalized with at least one amine group at the site of oxidative ring-opening. Aqueous compositions in which the amine-functionalized saccharide polymer is present may be particularly advantageous in that the aqueous composition (filtrate) removed from the plurality of particles has improved clarity and contains a reduced amount of residual fines. Thus, when the amine-functionalized saccharide polymer is present during the dehydration process, the need for a clarifier in the filtrate after dehydration may be reduced or eliminated.

[0071] The step of contacting the aqueous composition with the plurality of particles may include static mixing of the aqueous composition with the plurality of particles, agitation of the aqueous composition with the plurality of particles, flowing the aqueous composition through the plurality of particles (e.g., on a filter or screen), or any combination thereof. Other suitable contacting techniques, such as gravitational settling of the plurality of particles within the aqueous composition, are also contemplated. Suitable contact times may range from about 10 seconds to about 24 hours, from about 30 seconds to about 10 minutes, from about 1 minute to about 5 minutes, from about 1 minute to about 30 minutes, or from about 10 minutes to about 60 minutes. Contacting may occur at any temperature between the freezing point and the boiling point of the aqueous composition. In some embodiments, contacting may occur at a temperature between room temperature (23°C) and about 60°C, or between about room temperature and about 35°C.

[0072] The step of removing the aqueous composition from the plurality of particles may include filtration, screening, decantation, centrifugation, hydrocyclone separation, gravity settling, or any combination thereof. After a substantial majority of the aqueous composition has been removed from the plurality of particles (e.g., after >95% by volume of the aqueous composition or >99% by volume of the aqueous composition has been removed), the plurality of particles may be further dried. Further drying may be performed by heating, air drying, exposure to reduced pressure, or any combination thereof. In some examples, further drying may be performed in a rotary dryer or a fluidized bed dryer, examples of which will be familiar to those skilled in the art. During or after the further drying process, the plurality of particles may optionally be further sized (size separated or sizing).

[0073] In a non-limiting embodiment, the plurality of particles that undergo at least partial dewatering in accordance with the present disclosure may comprise a plurality of sand particles. The sand particles may be obtained, for example, from a sand mine, and after or during refining to a desired sand grade, the sand particles may be contacted with an aqueous composition to undergo at least partial dewatering in accordance with the present disclosure. Other suitable particulate materials that may undergo at least partial dewatering in accordance with the present disclosure include, for example, aggregate, slag, wood chips, iron oxide (e.g., for treatment in iron ore pelletizing processes), sludge materials from water treatment and chemical processing, drilling waste, mineral processing residues, and the like.

[0074] The aqueous composition disclosed herein may provide a lower level of residual moisture within the particles compared to contacting the particles with simple water. The residual moisture content within the particles after removing the aqueous composition may be about 20% by weight or less, or about 19% by weight or less, or about 18% by weight or less, based on the total weight of the particles and the residual moisture. In some examples or other examples, the residual moisture content after contacting the particles with the aqueous composition may be reduced by about 5% or more, about 6% or more, about 7% or more, about 8% or more, about 9% or more, or about 10% or more, e.g., about 5% to about 10%, compared to the moisture content obtained when contacting the particles with simple water. After the aqueous composition has been substantially removed from the particles, the particles may be further dried, as described in more detail above. After further drying, the residual moisture content may be, for example, about 5% by weight or less, or about 1% by weight or less. The aqueous composition can reduce the amount of residual moisture in the plurality of microparticles compared to the amount of residual moisture that would otherwise be present, so that the further drying process can be carried out more efficiently because there is less residual moisture to remove. Considering that a large amount of particles may be dried during the drying process, even a small reduction in the amount of residual moisture can significantly increase the efficiency of the drying process. Therefore, the aqueous composition of the present disclosure may enable the washing and drying of microparticles in a more efficient manner compared to water alone.

[0075] In some embodiments, dewatering of the plurality of particles may occur in a subterranean formation, such as during subterranean processing operations described below. In other embodiments, dewatering of the plurality of particles may occur in conjunction with a particle manufacturing process or a particle mining process, as described above. (Underground processing work)

[0076] The recovery of hydrocarbon resources (such as oil and gas) from subterranean formations is often carried out 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. An appropriate treatment chemical or treatment fluid may be selected based on the particular conditions that exist or are expected to exist downhole.

[0077] The aqueous compositions of the present disclosure may be formulated as subsurface treatment fluids. Treatment fluids may be used in various subsurface treatment operations to facilitate or promote desired outcomes within subsurface formations. As used herein, the term "treatment fluid" refers to any fluid used in a subsurface treatment operation that involves achieving a desired function and / or a desired purpose. Unless otherwise specified, the use of the term "treatment fluid" does not imply any specific action by the treatment fluid or its components. Examples of treatment operations that may be facilitated by the use of the reaction products, emulsion compositions, and emulsified fluids of the present disclosure include, but are not limited to, drilling operations, stimulation operations, production operations, remediation operations, erosion control operations, etc., which may include, for example, fracturing operations, gravel packing operations, acidizing operations, descaling operations, consolidation operations, workover operations, cleanup operations, diversion operations, etc.

[0078] 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.

[0079] 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 fluid" 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.

[0080] 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 perforation processes. In another example, the cleanup fluid can be used to remove filter cake on the wellbore wall.

[0081] 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 an increased viscosity fluid used in conjunction with a fracturing operation. Proppant particles may be present in the fracturing fluid to maintain the flow paths created or extended by the fracturing operation in an open condition.

[0082] 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.

[0083] 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 containing 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, while hydrofluoric acid may be present in compositions used in the acid treatment of siliceous formations.

[0084] 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 unblock drilling or extraction equipment.

[0085] As used herein, the term "completion fluid" refers to fluids (including cementing compositions and cementing fluids) used during the completion stage of a well.

[0086] As used herein, the term "cementing fluid" refers to a fluid used during cementing operations in a wellbore.

[0087] The aqueous compositions 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 wetting within subterranean formations to enhance the recovery of hydrocarbon resources from the formations.

[0088] In any of the above treatment operations, the treatment fluid may be foamed. Foamed fracturing fluids may be advantageous, for example, in transporting proppant particles to a location within a wellbore, compared to treatment fluids with increased viscosity. When foamed, the treatment fluid may have a foam quality ranging from about 1% to about 99%.

[0089] The aqueous compositions of the present disclosure may be formulated into any of the treatment fluids described above. Treatment fluids of the present disclosure may be characterized by aqueous composition concentrations of about 0.1 gpt (gpt per thousand gallons) to about 10 gpt, 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%, about 0.01% to about 0.1%, or about 0.02% to about 0.05%. The concentration selected may vary depending on the specific requirements for a given treatment operation and / or the unique subsurface conditions encountered downhole.

[0090] The treatment fluids of the present disclosure may optionally further contain any number of additives that may be used in the oilfield service industry. Examples of additives that may be present in the treatment fluid in combination with the reaction product of the present disclosure include, for example, surfactants, viscosity enhancers, gelling agents, gel stabilizers, antioxidants, polymer degradation inhibitors, relative permeability modifiers, scale inhibitors, corrosion inhibitors, chelating agents, foaming agents, defoamers, antifoaming agents, emulsifiers, demulsifiers, iron control agents, proppants or other particles, 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, biocides, and the like, as well as any combination thereof. Suitable examples of these additives will be known to those skilled in the art.

[0091] Embodiments disclosed herein include:

[0092] A. Aqueous compositions for promoting dehydration, the aqueous composition comprising: an aqueous carrier fluid; a neutral surfactant or a reaction product form thereof; a reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, where the first saccharide polymer comprises a dextran, a dextrin compound, or any combination thereof, and the reaction product of the first saccharide polymer and the 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 in the aqueous carrier fluid; a zwitterionic surfactant; and an amine-functionalized saccharide polymer formed from a second saccharide polymer containing a plurality of glucose units, at least a portion of which have been oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opened site.

[0093] B. A method for dehydrating a plurality of particles, the method including the steps of providing an aqueous composition containing: an aqueous carrier fluid; a neutral surfactant or a reaction product form thereof; a reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, where the first saccharide polymer comprises dextran, a dextrin compound, or any combination thereof, and the reaction product of the first saccharide polymer and the 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 in the aqueous carrier fluid; and a zwitterionic surfactant; contacting the aqueous composition with the plurality of particles; and removing the aqueous composition from the plurality of particles to facilitate at least partial dehydration of the plurality of particles.

[0094] B1. The method of B1, wherein the aqueous composition further contains an amine-functionalized saccharide polymer prepared from a second saccharide polymer containing a plurality of glucose units, wherein at least a portion of the glucose units have been oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opened site.

[0095] Embodiments A, B, and B1 may include one or more of the following additional embodiments in any combination.

[0096] Element 1: The aqueous composition further contains glycerol.

[0097] Element 2: The reaction product of the first saccharide polymer is formed from a fatty acid ester, and at least a portion of the glycerol is derived from the fatty acid ester.

[0098] Element 2A: The reaction product of the first saccharide polymer is formed from a fatty acid ester, and the reaction product further contains glycerol.

[0099] 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.

[0100] Element 4: The reaction product of the first saccharide polymer is formed from at least one fatty acid having from about 4 to about 30 carbon atoms.

[0101] Element 5: The reaction product of the first saccharide polymer and the fatty acid or fatty acid ester is present in the aqueous carrier fluid at a concentration effective to reduce the surface tension of the neutral surfactant.

[0102] Element 6: The neutral surfactant or reaction product form thereof is present in the aqueous carrier fluid at a concentration sufficient to solubilize the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester in the aqueous carrier fluid.

[0103] Element 7: The first saccharide polymer and / or the second saccharide polymer contains a dextrin compound, and the dextrin compound contains maltodextrin.

[0104] Element 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is about 0.2 or more based on

[0105] Element 9: The first saccharide polymer reaction product comprises a fatty acid ester saccharide polymer reaction product.

[0106] Element 10: The neutral surfactant contains a fatty acid alkanolamide.

[0107] Element 11: The fatty acid alkanolamide contains a compound selected from the group consisting of cocamide diethanolamine, cocamide monoethanolamine, cocamide diisopropanolamine, palmitamide diethanolamine, palmitamide monoethanolamine, palmitamide diisopropanolamine, and any combination thereof.

[0108] Element 12: The zwitterionic surfactant contains at least one betaine.

[0109] Element 13: The amine-functionalized saccharide polymer comprises an amine-functionalized dextrin compound containing from 2 to about 20 glucose units joined together by α(1,4) glycosidic linkages, an amine-functionalized dextran containing multiple glucose units joined together by α(1,6) glycosidic linkages, or any combination thereof.

[0110] Element 14: The amine-functionalized saccharide polymer has a secondary or tertiary amine covalently attached directly to one or more oxidative ring-opening sites.

[0111] Element 15: The amine-functionalized saccharide polymer has a primary alcohol and a secondary or tertiary amine at one or more oxidative ring-opening sites.

[0112] Element 16: Dewatering occurs in subsurface layers.

[0113] Element 17: Dewatering is performed in conjunction with the particle manufacturing or particle mining process.

[0114] Element 18: The step of removing the aqueous composition from the plurality of particles includes filtration, screening, decantation, centrifugation, hydrocyclone separation, gravity settling, or any combination thereof.

[0115] Element 19: The plurality of particles comprises a plurality of sand particles.

[0116] By way of non-limiting example, exemplary combinations applicable to A, B, and B1 include: 2, 2A, and / or 3, and 4 and / or 6; 2, 2A, and / or 3, and 7; 2, 2A, and / or 3, and 9; 2, 2A, and / or 3, and 10; 2, 2A, and / or 3, and 10 and 11; 2, 2A, and / or 3, and 10 and 12; 2, 2A, and / or 3, and 10-12; 2, 2A, and / or 3, and 13; 2, 2A, and and / or 3, and 16 or 17; 2, 2A, and / or 3, and 18; 2, 2A, and / or 3, and 19; 2, 2A, and / or 3, and 17 and 18; 2, 2A, and / or 3, and 17 and 19; 2, 2A, and / or 3, and 17-19; 4, and 5, and / or 6; 4 and 7; 4 and 9; 4 and 10; 4, and 10 and 11; 4, and 10 and 12; 4 and 12; 4 and 10-12; 4 and 13; 4, and 16 or 17; 4 and 18; 4 and and 19;4, and 17 and 18;4, and 17 and 19;4, and 17-19;7 and 8;7 and 9;7 and 10;7, and 10 and 11;7, and 10 and 12;7 and 12;7 and 10-12;7 and 13;7, and 16 or 17;7 and 18;7 and 19;7, and 17 and 18;7, and 17 and 19;7, and 17-19;9 and 10;9, and 10 and 11;9, and 10 and 12;9 and 12;9 and 10-12;9 and 13;9, and 16 if or 17; 9 and 18; 9 and 19; 9, and 17 and 18; 9, and 17 and 19; 9, and 17-19; 12 and 13; 12 and 14; 12, 14, and 15; 12 and 15; 12, and 16 or 17; 12 and 18; 12 and 19; 12, and 17 and 18; 12, and 17 and 19; 12, and 17-19; 13 and 14; 13-15; 13 and 15; 13, and 16 or 17; 13 and 18; 13 and 19; 13, and 17 and 18; 13, and 17 and 19;13, and 17-19; 17 and 18; 17 and 19; and 17-19. ;

[0117] The present disclosure is further directed to the following non-limiting clauses:

[0118] Item 1. Aqueous carrier fluid; Neutral surfactants or their reaction product forms; a reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, wherein the first saccharide polymer comprises a dextran, a dextrin compound, or any combination thereof, and wherein the reaction product form of the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester, and a neutral surfactant, if present, is formed in the presence of a hydroxide base in an aqueous carrier fluid; Zwitterionic surfactants; and an amine-functionalized saccharide polymer formed from a second saccharide polymer containing a plurality of glucose units, at least a portion of which have been oxidatively ring-opened and functionalized with at least one amine group at the oxidatively ring-opened sites; An aqueous composition comprising:

[0119] Item 2. The aqueous composition of Item 1, further containing glycerol.

[0120] Item 3. The aqueous composition of item 2, wherein the reaction product of the first saccharide polymer is formed from a fatty acid ester, and at least a portion of the glycerol is derived from the fatty acid ester.

[0121] Item 4. The aqueous composition of any one of Items 1 to 3, wherein the fatty acid ester contains a glycerol ester containing up to three kinds of fatty acids having about 4 to about 30 carbon atoms.

[0122] Item 5. The aqueous composition of item 1, wherein the reaction product of the first saccharide polymer is formed from at least one fatty acid having from about 4 to about 30 carbon atoms.

[0123] Item 6. The aqueous composition of item 1, wherein the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester is present in the aqueous carrier fluid at a concentration effective to reduce the surface tension of the neutral surfactant.

[0124] Item 7. The aqueous composition of item 1 or 6, wherein the neutral surfactant or reaction product form thereof is present in the aqueous carrier fluid at a concentration effective to solubilize the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester in the aqueous carrier fluid.

[0125] Item 8. The aqueous composition of Item 1, wherein the first saccharide polymer and / or the second saccharide polymer contains a dextrin compound, and the dextrin compound contains maltodextrin.

[0126] Item 9. The aqueous composition of Item 1, wherein the first saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0127] Item 10. The aqueous composition of item 1, wherein the second saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0128] Item 11. The molar ratio of the fatty acid to the first 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 第1のサッカライドポリマー中のグルコースモノマー Item 11. The aqueous composition of any one of items 1 or 8 to 10, wherein the .alpha.-methyl-.alpha.-methyl-.alpha.-methyl.beta.

[0129] Item 12. The molar ratio of fatty acid to first 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 第1のサッカライドポリマー中のグルコースモノマー Item 11. The aqueous composition of any one of items 1 or 8 to 10, wherein the average molecular weight is about 0.2 to about 0.9 based on the molecular weight of the aqueous composition.

[0130] Item 13. The aqueous composition of any one of Items 1 or 8 to 10, wherein the reaction product of the first saccharide polymer comprises a fatty acid ester saccharide polymer reaction product.

[0131] Item 14. The aqueous composition of any one of items 1 or 8 to 10, wherein the zwitterionic surfactant contains at least one betaine.

[0132] Item 15. The aqueous composition of any one of items 1 or 8 to 10, wherein the neutral surfactant contains a fatty acid alkanolamide.

[0133] Item 16. The aqueous composition of Item 15, wherein the fatty acid alkanolamide contains a compound selected from the group consisting of cocamide diethanolamine, cocamide monoethanolamine, cocamide diisopropanolamine, palmitic acid amide diethanolamine, palmitic acid amide monoethanolamine, palmitic acid amide diisopropanolamine, and any combination thereof.

[0134] Item 17. The aqueous composition of item 1, wherein the amine-functionalized saccharide polymer comprises an amine-functionalized dextrin compound containing from 2 to about 20 glucose units linked together by α(1,4) glycosidic linkages, an amine-functionalized dextran containing a plurality of glucose units linked together by α(1,6) glycosidic linkages, or any combination thereof.

[0135] Item 18. The aqueous composition of item 1 or 17, wherein the amine-functionalized saccharide polymer has a secondary or tertiary amine covalently attached directly to one or more oxidative ring-opening sites.

[0136] Item 19. The aqueous composition of item 18, wherein the amine-functionalized saccharide polymer has a primary alcohol and a secondary or tertiary amine at one or more oxidative ring-opening sites.

[0137] Item 20. Aqueous carrier fluid; Neutral surfactants or their reaction product forms; a reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, wherein the first saccharide polymer comprises a dextran, a dextrin compound, or any combination thereof, and the reaction product form of the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester, and a neutral surfactant, if present, is formed in the presence of a hydroxide base in an aqueous carrier fluid; and Zwitterionic surfactants; providing an aqueous composition containing: contacting a plurality of particles with an aqueous composition; and removing the aqueous composition from the plurality of particles; A method comprising: the aqueous composition increases dehydration of the plurality of particles relative to water, increases flow rate through the plurality of particles relative to water, or any combination thereof; method.

[0138] Item 21. The method of item 20, wherein the first saccharide polymer comprises maltodextrin.

[0139] Item 22. The method of item 20, wherein the aqueous composition further contains an amine-functionalized saccharide polymer prepared from a second saccharide polymer containing a plurality of glucose units, wherein at least a portion of the glucose units have been oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opened site.

[0140] Item 23. The method of Item 22, wherein the first saccharide polymer and / or the second saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0141] Item 24. The method of Item 22, wherein the first saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0142] Item 25. The method of Item 22, wherein the second saccharide polymer comprises a dextrin compound, and the dextrin compound comprises maltodextrin.

[0143] Item 26. The method of item 22, wherein the amine-functionalized saccharide polymer comprises an amine-functionalized dextrin compound containing from 2 to about 20 glucose units linked together by α(1,4) glycosidic linkages, an amine-functionalized dextran containing a plurality of glucose units linked together by α(1,6) glycosidic linkages, or any combination thereof.

[0144] Clause 27. The method of any one of clauses 22-26, wherein the amine-functionalized saccharide polymer has a secondary or tertiary amine covalently attached directly to one or more oxidative ring-opening sites.

[0145] Item 28. The method of item 27, wherein the amine-functionalized saccharide polymer has a primary alcohol and a secondary or tertiary amine at one or more oxidative ring-opening sites.

[0146] Item 29. The method of any one of items 20 to 26, wherein dewatering is performed in a subsurface layer.

[0147] Item 30. The method of any one of items 20 to 26, wherein the dehydration is performed in conjunction with a particle manufacturing process or a particle mining process.

[0148] Item 31. The method of any one of items 20 to 26, wherein the step of removing the aqueous composition from the plurality of particles comprises filtration, screening, decantation, centrifugation, hydrocyclone separation, gravity settling, or any combination thereof.

[0149] Item 32. The method according to any one of Items 20 to 26, wherein the plurality of particles includes a plurality of sand particles.

[0150] Item 33. The method of any one of items 20 to 26, wherein the reaction product of the first saccharide polymer is formed from a fatty acid ester, and the reaction product further contains glycerol.

[0151] Item 34. The method of Item 33, wherein the fatty acid ester comprises a glycerol ester containing up to three fatty acids having from about 4 to about 30 carbon atoms.

[0152] Item 35. The method of any one of items 20-26, wherein the reaction product of the first saccharide polymer is formed from at least one fatty acid having from about 4 to about 30 carbon atoms.

[0153] Item 36. The molar ratio of fatty acid to first 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 第1のサッカライドポリマー中のグルコースモノマー 27. The method of any one of paragraphs 20 to 26, wherein the value is about 0.2 or greater based on the

[0154] Item 37. The molar ratio of fatty acid to first 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 第1のサッカライドポリマー中のグルコースモノマー 27. The method of any one of paragraphs 20 to 26, wherein the ratio is about 0.2 to about 0.9 based on the formula:

[0155] Item 38. The method of any one of Items 20 to 26, wherein the neutral surfactant contains a fatty acid alkanolamide.

[0156] Item 39. The method of Item 38, wherein the fatty acid alkanolamide contains a compound selected from the group consisting of cocamide diethanolamine, cocamide monoethanolamine, cocamide diisopropanolamine, palmitic acid amide diethanolamine, palmitic acid amide monoethanolamine, palmitic acid amide diisopropanolamine, and any combination thereof.

[0157] Item 40. The method of any one of items 20 to 26, wherein the zwitterionic surfactant contains at least one betaine.

[0158] To facilitate a better understanding of the present disclosure, the following examples of various representative embodiments are set forth, which should not be construed as limiting or defining the scope of the present invention. (Example)

[0159] Example 1: Representative Procedure for Preparation of Maltodextrin Reaction Products with Glycerol Esters. 25.00 g of fatty acid alkanolamide surfactant and 10.00 g of KOH (45% active solution) were mixed 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 result in an HLB of 12 or 16 upon reaction product formation. The amount of water was selected to result in a surfactant concentration of 5 wt%, a fatty acid ester (oil) concentration of 2.5 wt%, and a 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 processing in further formulations and further testing described below. Dextran reaction products may also be formed using similar procedures. Other fatty acid ester and alkanolamide surfactants may be used as well.

[0160] Example 2: Representative Procedure for Preparation of Maltodextrin Reaction Product with Free Fatty Acids. 25.00 g of fatty acid alkanolamide surfactant and 10.00 g of KOH (45% active solution) were mixed in water. The reaction mixture was mechanically stirred and heated to 65°C. A fatty acid mixture containing saturated fatty acids, primarily lauric and myristic acids, 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 achieve an HLB of 12 or 16. The amount of water was selected to achieve a surfactant concentration of 5 wt%, a fatty acid concentration of 2.5 wt%, and a 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 processing in further formulations and further testing described below. Dextran reaction products may also be formed using similar procedures. Other fatty acid ester and alkanolamide surfactants may be used as well.

[0161] Amine-functionalized maltodextrin. Amine-functionalized maltodextrin was prepared as described in U.S. Patent No. 11,130,905. Briefly, an aqueous solution of maltodextrin was treated with sodium periodate at room temperature and used without further purification to react with various amines. The product was 15% active by weight.

[0162] Flow Performance of Aqueous Compositions. Aqueous compositions were formulated as shown in Table 1. The aqueous compositions in Table 1 were diluted to a concentration of 2 gpt (gallons per thousand gallons) before undergoing the flow performance tests described further below.

[0163] [Table 1]

[0164] After dilution to 2 gpt, the aqueous compositions in Table 1 were contacted with sand particles to evaluate their flowability. Contact with sand particles was performed as follows: 400 g of dry sand was placed in a Buchner funnel containing a 25 μm filter to form a sand pack. The sand particles were used as received and no other pretreatment was performed. 250 mL of the diluted aqueous composition was poured into the sand pack and allowed to drain through the Buchner funnel by gravity (no vacuum was applied). A stopwatch was started when the aqueous composition was poured into the sand pack, and the drained aqueous composition was collected in a graduated cylinder. The volume of the aqueous fluid was recorded as a function of time. The time was recorded every time 20 mL of filtrate was collected, as well as the total volume of filtrate collected at 5 minutes. The volume and time at which the sand pack was no longer submerged in the aqueous composition were also recorded. The volume and time at which the sand pack was no longer submerged in the aqueous composition were also recorded.

[0165] After 5 minutes, the resulting wet sand filter cake was placed on an aluminum foil tare and weighed. The wet sand filter cake was then heated in an oven at 105°C (2-3 hours) until it reached a constant mass. The resulting dry filter cake mass was compared to the wet filter cake mass to determine the residual moisture content of the wet sand filter cake after contact with the aqueous composition.

[0166] Figure 2 is a graph of the flow performance (volume of aqueous fluid collected versus time) of various aqueous compositions through sand particles. As shown, the aqueous composition of entry 7 (maltodextrin reaction product / neutral surfactant / cocamidopropyl betaine) provided significantly faster flow performance than the other samples, as indicated by the left shift of the curve compared to the other samples. The left shift of the curve indicates a greater amount of aqueous composition collected in a shorter time. All experimental samples demonstrated better flow performance than the tap water control (entry 1).

[0167] Table 2 shows the residual moisture content of the sand particles after each of the above treatments.

[0168] [Table 2]

[0169] As shown in Table 2, the aqueous composition containing betaine surfactant alone (Entry 4) produced the lowest residual moisture content. Of the aqueous compositions containing amine-functionalized maltodextrin and / or the maltodextrin reaction product of Example 2, the aqueous compositions of Entries 5 and 8 produced particularly low residual moisture contents. All residual moisture contents were equal to or less than that produced by the tap water control (Entry 1). The clarity of the filtrate was significantly better for the aqueous composition of Entry 8 compared to Entry 5 or the other aqueous compositions tested above.

[0170] 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 present 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 the very least, be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0171] 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 implementation incorporating embodiments of the present invention, numerous implementation-specific decisions must be made to achieve the developer's goals, including compliance with system-related, business-related, government-related, and other constraints (which may vary from implementation to implementation and from time to time). While 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.

[0172] 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.

[0173] 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, rather than 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.

[0174] 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 present disclosure may be modified and practiced 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 described in the claims below. It is therefore evident that the specific exemplary embodiments disclosed above may be altered, combined, or modified, and all such variations are considered within the scope of the present disclosure. The systems, compositions, means, and methods illustratively disclosed herein may suitably be practiced in the absence of any element not specifically disclosed herein and / or any optional element disclosed herein. Although systems, compositions, means, and methods are described in terms "containing," "including," or "comprising" 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 above-disclosed values and ranges are subject to some variation. Whenever a numerical range with a lower and upper limit is disclosed, any numerical value and any encompassed range within that range is specifically disclosed. In particular, all ranges of values disclosed herein (in the form "from about a to about b," or, equivalently, "from 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. Furthermore, terms in the claims have their plain, ordinary meaning unless expressly and unambiguously defined otherwise by the patent owner. Furthermore, the indefinite article "a" or "an," as used in the claims, is defined herein to mean one or more of the element it introduces. If there is any discrepancy between the use of a word or term in this specification and the use of that word or term in one or more patents or other documents incorporated herein by reference, the consistent definition in this specification should prevail.

Claims

1. Aqueous carrier fluid; Neutral surfactants or their reaction product forms; A reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, wherein the first saccharide polymer contains dextran, a dextrin compound, or any combination thereof, and the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester, and the reaction product form of the neutral surfactant, if present, are formed in the aqueous carrier fluid in the presence of a hydroxide base; zwitterionic surfactant; And, An amine-functionalized saccharide polymer formed from a second saccharide polymer containing a plurality of glucose units, each of which at least a portion of the glucose units are oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opening site; An aqueous composition containing a functionalized saccharide polymer for dehydrating particles.

2. An aqueous composition containing a functionalized saccharide polymer for dehydrating particles according to claim 1, wherein the first saccharide polymer and / or the second saccharide polymer contains a dextrin compound, and the dextrin compound contains maltodextrin.

3. The molar ratio of the fatty acid to the first saccharide polymer in the reaction product is molar 脂肪酸もしくは脂肪酸エステル中の脂肪酸 : Mole 第１のサッカライドポリマー中のグルコースモノマー An aqueous composition containing a functionalized saccharide polymer for dehydrating particles according to claim 1 or claim 2, wherein the value is approximately 0.2 to approximately 0.9 based on the formula.

4. An aqueous composition comprising a functionalized saccharide polymer for dehydrating particles according to any one of claims 1 to 3, wherein the zwitterionic surfactant contains at least one betaine.

5. An aqueous composition containing a functionalized saccharide polymer for dehydrating particles according to any one of claims 1 to 4, wherein the neutral surfactant contains a fatty acid alkanolamide.

6. An aqueous composition containing a functionalized saccharide polymer for dehydrating particles according to claim 1, wherein the amine-functionalized saccharide polymer contains an amine-functionalized dextrin compound containing 2 to about 20 glucose units linked together by α(1,4) glycosidic bonds, an amine-functionalized dextran containing a plurality of glucose units linked together by α(1,6) glycosidic bonds, or any combination thereof.

7. Aqueous carrier fluid; Neutral surfactants or their reaction product forms; A reaction product of a first saccharide polymer and a fatty acid or fatty acid ester, wherein the first saccharide polymer contains dextran, a dextrin compound, or any combination thereof, and the reaction product of the first saccharide polymer and the fatty acid or fatty acid ester, and the reaction product form of the neutral surfactant, if present, are formed in the aqueous carrier fluid in the presence of a hydroxide base; And, zwitterionic surfactant; A step of providing an aqueous composition containing; A step of bringing the aqueous composition into contact with a plurality of particles; And, A step of removing the aqueous composition from the plurality of particles; A method including, The aqueous composition is such that, compared to water, it increases the dewatering of the plurality of particles, or increases the flow rate through the plurality of particles compared to water, or any combination thereof. A method for dehydrating particles.

8. The method for dehydrating particles according to claim 7, wherein the aqueous composition further contains an amine-functionalized saccharide polymer, which is produced from a second saccharide polymer containing a plurality of glucose units, each of which at least a portion of the glucose units are oxidatively ring-opened and functionalized with at least one amine group at the oxidative ring-opening site.

9. The method for dehydrating particles according to claim 8, wherein the first saccharide polymer and / or the second saccharide polymer contains a dextrin compound, and the dextrin compound contains maltodextrin.

10. The method for dehydrating particles according to claim 8, wherein the amine-functionalized saccharide polymer contains an amine-functionalized dextrin compound containing 2 to about 20 glucose units linked together by α(1,4) glycosidic bonds, an amine-functionalized dextran containing a plurality of glucose units linked together by α(1,6) glycosidic bonds, or any combination thereof.

11. The method for dewatering particles according to any one of claims 7 to 10, wherein the dewatering is performed in an underground layer.

12. The method for dewatering particles according to any one of claims 7 to 10, wherein the dewatering is performed in conjunction with a particle manufacturing process or a particle mining process.

13. The method for dehydrating particles according to any one of claims 7 to 10, wherein the step of removing the aqueous composition from the plurality of particles comprises filtration, screening, decantation, centrifugation, hydrocyclone separation, gravity sedimentation, or any combination thereof.

14. The method for dewatering particles according to any one of claims 7 to 10, wherein the plurality of particles contain a plurality of sand particles.

15. The method for dehydrating particles according to any one of claims 7 to 10, wherein the neutral surfactant contains a fatty acid alkanolamide.

Images