Amphiphilic glucan ester derivatives

Abstract

Disclosed herein are compositions comprising ester derivatives of a glucan wherein the glucan has a degree of substitution (DoS) of up to about 3.0 substituted by at least two organic groups ester attached to the glucan alone wherein (i) at least one of the organic groups is a cationic organic group, and (ii) at least one of these organic groups is a hydrophobic organic group. Further disclosed are methods for preparing these compositions and various applications using them.

Description

[0001] This application claims the benefit of U.S. Provisional Application No. 63 / 359,965 (filed on July 11, 2022), which is incorporated herein by reference in its entirety. Technical Field

[0002] The present disclosure belongs to the field of polysaccharide derivatives. For example, the present disclosure relates to amphiphilic glucan ester derivatives and their uses in various applications. Background Art

[0003] Driven by the desire to find new structural polysaccharides using enzymatic synthesis or microbial genetic engineering, researchers have discovered oligosaccharides and polysaccharides that are biodegradable and can be economically prepared from raw materials from renewable sources. Additional studies have shown that such polysaccharides can be chemically modified (derivatized) to have additional utility in areas such as personal care, home care, industrial care, pharmaceuticals, and food. For example, ethers and esters of α-glucans containing α-1,3 glycosidic bonds have been disclosed to have various applications (e.g., U.S. Patent Application Publication Nos. 2016 / 0304629, 2016 / 0311935, 2017 / 0204232, 2014 / 0187767, 2020 / 0308371). Various derivatives of α-glucan containing α-1,6 glycosidic bonds and applications using the same have also been disclosed (e.g., U.S. Patent Application Publication Nos. 2018 / 0312781, 2018 / 0237816, 2018 / 0282385).

[0004] Despite these advances, some glucan derivatives with desired utility have poor biodegradability characteristics due to elevated levels of derivatization. Although some glucans with low levels of derivatization exhibit better biodegradability, such products generally fail to provide optimal, or even adequate, activity. Therefore, there remains a need for product ingredients that are not only renewable but also biodegradable and provide properties that are equal to or better than those of products with synthetic components. Amphiphilic glucan ester derivatives (and other compounds) are disclosed herein to meet this need. Summary of the invention

[0005] In one embodiment, the present disclosure is directed to a composition comprising an ester derivative of dextran, wherein the dextran has a degree of substitution (DoS) of up to about 3.0 substituted with at least two organic groups attached to the dextran individually ester, wherein (i) at least one of the organic groups is a cationic organic group, and (ii) at least one of the organic groups is a hydrophobic organic group.

[0006] In another embodiment, the present disclosure relates to a method for producing an ester derivative of glucan. Such method comprises: (a) contacting glucan with at least two esterifying agents, wherein at least one of the esterifying agents comprises a cationic organic group, wherein at least one of the esterifying agents comprises a hydrophobic organic group, wherein at least one cationic organic group and at least one hydrophobic organic group are esterified to the glucan, thereby producing an ester derivative of the glucan, wherein the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 substituted by the cationic organic group and the hydrophobic organic group, and (b) optionally, isolating the ester derivative of the glucan produced in step (a).

[0007] In another embodiment, the present disclosure relates to a method of styling hair. Such a method comprises at least steps (a) and (b), or steps (c) and (d), as follows: (a) contacting hair with a glucan ester derivative herein, thereby providing treated hair, and (b) placing the treated hair in a desired form; or (c) placing the hair in a desired form, and (d) contacting the hair of step (c) with a glucan ester derivative herein, thereby providing treated hair; and (e) optionally, removing the solvent (if any) used to deliver the glucan ester derivative to the hair in step (a) or (d). BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 : shows the biodegradability characteristics of betaine modified α-1,3-glucan esters. RN3 and RN7 curves represent repeated tests using the same glucan ester sample. Refer to Example 3. DETAILED DESCRIPTION

[0009] The disclosures of all cited patent and non-patent literature are incorporated herein by reference in their entirety.

[0010] Unless disclosed otherwise, the terms "a" or "an" as used herein are intended to cover one or more (ie, at least one) of the referenced features.

[0011] If present, all ranges are inclusive and combinable unless otherwise indicated. For example, when a range of "1 to 5" (i.e., 1-5) is listed, the listed range should be interpreted as including the ranges "1 to 4", "1 to 3", "1-2", "1-2 and 4-5", "1-3 and 5", etc. Unless otherwise expressly indicated, the numerical values ​​of the various ranges in this disclosure are stated as approximate values, as if the minimum and maximum values ​​in the stated ranges are preceded by the word "about". In this way, slight variations above and below the described ranges can typically be used to achieve substantially the same results as the values ​​within these ranges. Moreover, the disclosure of these ranges is intended to be a continuous range that includes every value between the minimum and maximum values.

[0012] Each maximum numerical limit given throughout this specification is intended to include each lower numerical limit, as if such lower numerical limits were expressly written herein. Each minimum numerical limit given throughout this specification will include each higher numerical limit, as if such higher numerical limits were expressly written herein. Each numerical range given throughout this specification will include each narrower numerical range falling within such wider numerical range, as if such narrower numerical ranges were all expressly written herein.

[0013] It should be understood that, for clarity, certain features of the present disclosure described above and below in the context of aspects / embodiments may also be provided in combination in a single element. Conversely, for brevity, various features of the present disclosure described in the context of a single aspect / embodiment may also be provided separately or in any sub-combination.

[0014] The term "polysaccharide" (or "glycan") means a polymeric carbohydrate molecule composed of long chains of monosaccharide units bound together by glycosidic bonds and which, when hydrolyzed, yields the constituent monosaccharides and / or oligosaccharides of the polysaccharide. The polysaccharide herein may be linear or branched, and / or may be a homopolysaccharide (composed of only one type of constituent monosaccharide) or a heteropolysaccharide (composed of two or more different constituent monosaccharides). Examples of polysaccharides herein include dextran (polydextrose) and soy polysaccharide.

[0015] " Glucan " herein is a class of polysaccharide, and it is the polymer (polyglucose) of glucose. Glucan can comprise for example about or at least about 90 % by weight, 91 % by weight, 92 % by weight, 93 % by weight, 94 % by weight, 95 % by weight, 96 % by weight, 97 % by weight, 98 % by weight, 99 % by weight or 100 % by weight of glucose monomeric units. The example of Glucan herein is alpha-glucan and beta-glucan.

[0016] The terms "α-glucan", "α-glucan polymer", etc. are used interchangeably herein. α-glucan is a polymer comprising glucose monomer units linked together by α-glycosidic bonds. In typical aspects, the glycosidic bonds of the α-glucans herein are about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or 100% α-glycosidic bonds. Examples of α-glucan polymers herein include α-1,3-glucan, α-1,4-glucan, and α-1,6-glucan.

[0017] The terms "β-glucan", "β-glucan polymer", and the like are used interchangeably herein. β-glucan is a polymer comprising glucose monomer units linked together by β-glycosidic bonds. In typical aspects, the glycosidic bonds of the β-glucans herein are about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or 100% β-glycosidic bonds. Examples of β-glucan polymers herein include β-1,3-glucan, β-1,4-glucan, and β-1,6-glucan.

[0018] Unless otherwise indicated, the term "sugar" and other similar terms refer to monosaccharides and / or disaccharides / oligosaccharides in this article. "Disaccharides" herein refer to carbohydrates with two monosaccharides connected by glycosidic bonds. "Oligosaccharides" herein may refer to carbohydrates with 3 to 15 monosaccharides, for example, connected by glycosidic bonds. Oligosaccharides may also be referred to as "oligomers". The monosaccharides (e.g., glucose and / or fructose) contained in disaccharides / oligosaccharides may be referred to as "monomer units", "monosaccharide units" or other similar terms.

[0019] The terms "α-1,3-glucan", "poly α-1,3-glucan", "α-1,3-glucan polymer", etc. are used interchangeably herein. α-1,3-glucan is an α-glucan comprising glucose monomer units linked together by glycosidic bonds, wherein at least about 50% of the glycosidic bonds are α-1,3. In some aspects, the α-1,3-glucan comprises about, or at least about 90%, 95%, or 100% α-1,3 glycosidic bonds. Most or all of the other bonds (if present) in the α-1,3-glucan herein are typically α-1,6, although some bonds may also be α-1,2 and / or α-1,4. The α-1,3-glucan herein is typically water-insoluble.

[0020] The terms "α-1,6-glucan", "poly α-1,6-glucan", "α-1,6-glucan polymer", "dextran" and the like herein refer to water-soluble α-glucans comprising glucose monomer units linked together by glycosidic bonds, wherein at least about 50% of the glycosidic bonds are α-1,6. In some aspects, the α-1,6-glucan comprises about, or at least about 90%, 95%, or 100% α-1,6-glycosidic bonds. Other bonds that may be present in the α-1,6-glucan include α-1,2, α-1,3, and / or α-1,4 bonds.

[0021] The terms "α-1,4-glucan", "poly α-1,4-glucan", "α-1,4-glucan polymer", and the like are used interchangeably herein. α-1,4-glucan is an α-glucan comprising glucose monomer units linked together by glycosidic bonds, wherein at least about 50% of the glycosidic bonds are α-1,4. In some aspects, the α-1,4-glucan comprises about, or at least about 90%, 95%, or 100% α-1,4-glycosidic bonds. Most or all of the other bonds (if present) in the α-1,4-glucan herein are typically α-1,6 (typically forming branches), but may also be α-1,2 and / or α-1,3. Examples of α-1,4-glucans herein include amylose, amylopectin, and starch.

[0022] The terms "β-1,4-glucan", "poly β-1,4-glucan", "β-1,4-glucan polymer", "cellulose" and the like are used interchangeably herein. β-1,4-glucan is a water-insoluble β-glucan comprising glucose monomer units linked together by glycosidic bonds, wherein about 100% of the glycosidic bonds are β-1,4. β-1,4-glucan can be disclosed, for example, in U.S. Patent Application Publication No. 2018 / 0334696.

[0023] The terms "β-1,3-glucan", "poly β-1,3-glucan", "β-1,3-glucan polymer", and the like are used interchangeably herein. β-1,3-glucan is a β-glucan comprising glucose monomer units linked together by glycosidic bonds, wherein at least about 50% of the glycosidic bonds are β-1,3. In some aspects, the β-1,3-glucan comprises about, or at least about 90%, 95%, or 100% β-1,3 glycosidic bonds. Most or all other bonds in the β-1,3-glucan herein, if present, are typically β-1,6 (usually forming branches). β-1,3-glucan can be as disclosed, for example, in U.S. Patent Application Publication No. 2014 / 0287919 and Stone, BA (2009, Chemistry of Beta-Glucans, edited by Antony Bacic et al., Chemistry, Biochemistry, and Biology of 1-3 Beta Glucans and Related Polysaccharides[1-3β-glucan and related polysaccharides chemistry, biochemistry and biology] , Academic Press, Burlington, Massachusetts), which is incorporated herein by reference.

[0024] The terms "soy polysaccharide" and "soy fiber" are used interchangeably herein and refer to high molecular weight, water-insoluble polysaccharide materials that can be obtained from soybeans. Typically, soybean polysaccharides are obtained from the cell wall structural components of soybeans. The soybean polysaccharides herein can be disclosed, for example, in U.S. Patent Application Publication No. 2018 / 0079832, which is incorporated herein by reference.

[0025] As referred to herein, "α-1,2 branches" (and similar terms) typically contain glucose α-1,2-linked to the dextran backbone; therefore, the α-1,2 branches herein may also be referred to as α-1,2,6 bonds. The α-1,2 branches herein typically have one glucose group (which may optionally be referred to as a side chain glucose).

[0026] As referred to herein, "α-1,3 branches" (and similar terms) typically contain glucoses α-1,3-linked to the dextran backbone; therefore, the α-1,3 branches herein may also be referred to as α-1,3,6 bonds. The α-1,3 branches herein typically have one glucose group (which may optionally be referred to as a side chain glucose).

[0027] As referred to herein, "α-1,4 branches" (and similar terms) typically contain glucose α-1,4-linked to the dextran backbone; therefore, the α-1,4 branches herein may also be referred to as α-1,4,6 bonds. The α-1,4 branches herein typically have one glucose group (which may optionally be referred to as a side chain glucose).

[0028] The percentage of branches in the polysaccharide herein refers to the percentage of all bonds in the polysaccharide that represent branch points. For example, the percentage of α-1,3 branches in the α-glucan herein refers to the percentage of all bonds in the glucan that represent α-1,3 branch points. Unless otherwise specified, the percentage of bonds disclosed herein is based on the total bonds of the polysaccharide, or for the portion of the polysaccharide to which the disclosure specifically relates.

[0029] The terms "linkage", "glycosidic linkage", "glycosidic bond" and the like refer to covalent bonds linking sugar monomers within a sugar compound (oligosaccharide and / or polysaccharide). Examples of glycosidic bonds include 1,6-α-D-glycosidic bonds (also referred to herein as "α-1,6" bonds), 1,3-α-D-glycosidic bonds (also referred to herein as "α-1,3" bonds), 1,4-α-D-glycosidic bonds (also referred to herein as "α-1,4" bonds), and 1,2-α-D-glycosidic bonds (also referred to herein as "α-1,2" bonds).

[0030] The glycosidic bond profile of a polysaccharide or its derivatives can be determined using any method known in the art. For example, the glycosidic bond profile can be determined using nuclear magnetic resonance (NMR) spectroscopy (e.g., 13CNMR and / or 1 H NMR) to determine the bond spectrum. These and other methods that can be used are disclosed in, for example, Food Carbohydrates: Chemistry, Physical Properties, and Applications [ Food Carbohydrates: Chemistry, Physical Properties and Applications ] (S. W. C. Cui, ed., Chapter 3, S. W. Cui, Structural Analysis of Polysaccharides, Taylor & Francis Group LLC, Boca Raton, Florida, 2005), which is incorporated herein by reference.

[0031] As used herein, the term "molar substitution" (MS) refers to the number of moles of organic groups per monomer unit of the polysaccharide derivatives herein. It should be noted that the molar substitution values ​​of the polysaccharide derivatives may have very high upper limits, such as hundreds or even thousands.

[0032] The "molecular weight" of a polysaccharide or polysaccharide derivative herein can be expressed as a weight average molecular weight (Mw) or a number average molecular weight (Mn), and its unit is Dalton (Da) or grams / mole. Alternatively, the molecular weight can be expressed as DPw (weight average degree of polymerization) or DPn (number average degree of polymerization). The molecular weight of smaller polysaccharide polymers (such as oligosaccharides) can optionally be provided as "DP" (degree of polymerization), and DP refers only to the number of monomers contained in the polysaccharide; "DP" can also characterize the molecular weight of a polymer based on a single molecule. Various means for calculating these different molecular weight measurements are known in the art, such as using high pressure liquid chromatography (HPLC), size exclusion chromatography (SEC) or gel permeation chromatography (GPC).

[0033] As used herein, Mw = ΣNiMi 2 / ΣNiMi calculates Mw; wherein Mi is the molecular weight of a single chain i and Ni is the number of chains having that molecular weight. In addition to SEC, the Mw of a polymer can be determined by other techniques such as static light scattering, mass spectrometry, MALDI-TOF (matrix-assisted laser desorption / ionization time of flight), small angle X-ray or neutron scattering, or ultracentrifugation. As used herein, Mn can be calculated as Mn=ΣNiMi / ΣNi, wherein Mi is the molecular weight of chain i and Ni is the number of chains having that molecular weight. In addition to SEC, the Mn of a polymer can be determined by various colligative methods such as vapor pressure osmosis, by spectroscopy such as proton NMR, proton FTIR, or end group determination by UV-Vis. As used herein, DPw and DPn can be calculated from Mw and Mn, respectively, by dividing them by the molar mass M1 of one monomer unit. In the case of an unsubstituted dextran polymer, M1=162. In the case of a substituted (derivatized) dextran polymer, M1=162+M f x DoS, where M f is the molar mass of the substituent group, and DoS is the degree of substitution (average number of substituent groups per one glucose unit of the dextran polymer).

[0034] "Polysaccharide derivatives" (and similar terms) herein (e.g., glucan derivatives such as α- or β-glucan derivatives) typically refer to polysaccharides that have been substituted with at least one type of organic group (e.g., acyl groups herein). The degree of substitution (DoS) of the polysaccharide derivatives herein can be up to about 3.0 (e.g., about 0.001 to about 3.0). The organic group that is an acyl group herein is connected to the polysaccharide derivative via an ester bond. The precursor of the polysaccharide derivative herein typically refers to the underivatized polysaccharide used to prepare the derivative (which can also be referred to as the polysaccharide portion of the derivative). The organic group that is an acyl group herein can be positively charged (cationic) or hydrophobic; generally, the cationic charge can be the charge that the organic group has when it is in the aqueous composition herein, and the pH of the aqueous composition should also be taken into account (in some aspects, the pH can be 4-10 or 5-9, or any pH as disclosed herein).

[0035] As used herein, the term "degree of substitution" (DoS, or DS) refers to the average number of hydroxyl groups substituted by one or more types of organic groups in each monomer unit of a polysaccharide derivative. The DoS of a polysaccharide derivative herein may be stated with reference to the DoS of a specific substituent or to the overall DoS, which is the sum of the DoS values ​​of different substituent types (e.g., if it is a mixed ester). Unless otherwise disclosed, when the DoS is stated without reference to a specific substituent type, it is meant to be the overall DoS.

[0036] The terms "glucan ester derivative", "glucan ester compound", "glucan ester" and the like are used interchangeably herein. The glucan ester derivative herein is typically a glucan that has been esterified with one or more cationic (positively charged) organic groups (i.e., cationic acyl groups) and one or more hydrophobic organic groups (i.e., hydrophobic acyl groups) such that the derivative has a DoS of up to about 3.0 for all of these organic groups. Such glucan esters may optionally be characterized herein as amphiphilic glucan esters due to having one or more different hydrophilic organic groups (particularly, one or more cationic organic groups) and one or more different hydrophobic organic groups. The glucan ester derivatives herein are characterized by comprising the substructure -C G -O-CO-C- is called an "ester", where "-C G "-" represents a carbon atom of a monomer unit (e.g., glucose) of a glucan ester derivative (where such a carbon atom is bonded to a hydroxyl group [-OH] in a polysaccharide precursor of the ester), and wherein "-CO-C-" is included in an acyl group.

[0037] The term "hydrophobic" herein may characterize a substituent organic group (substituent acyl group) that is non-polar and has little or no affinity for water and tends to repel water.

[0038] The term "hydrophilic" herein can characterize a substituent organic group (substituent acyl group) that is polar and has an affinity for interacting with polar solvents, particularly water or with other polar groups. Hydrophilic groups tend to attract water. Cationic organic groups (cationic acyl groups) herein are examples of hydrophilic organic groups.

[0039] In some aspects, the terms "esterification reaction", "esterification reaction composition", etc. refer to a reaction comprising at least a glucan as disclosed herein, two or more esterifying agents, and typically a solvent. The reaction is placed under appropriate conditions (e.g., solvent, time, temperature) for esterification of the hydroxyl groups of the glucose monomer units of the glucan with at least one cationic organic group (cationic acyl group) and at least one hydrophobic organic group (hydrophobic acyl group) provided by the esterifying agent, thereby producing an amphiphilic glucan ester compound / derivative.

[0040] As used herein, the term "aqueous liquid", "aqueous fluid", "aqueous conditions", "aqueous environment", "aqueous system", etc. may refer to water or an aqueous solution. The "aqueous solution" herein may include one or more dissolved salts, wherein the maximum total salt concentration may be about 3.5 wt % in some embodiments. Although the aqueous liquid herein typically includes water as the only solvent in the liquid, the aqueous liquid may optionally include one or more other solvents (e.g., polar organic solvents) that are miscible in water. Therefore, the aqueous solution may include a solvent having at least about 10 wt % water.

[0041] For example, an "aqueous composition" herein has a liquid component comprising about or at least about 10, 20, 30, 40, 50, 60, 70, 80, 90, 95, 99, or 100 wt % water. Examples of aqueous compositions include, for example, mixtures, solutions, dispersions (e.g., suspensions, colloidal dispersions), and emulsions. In some embodiments, the pH of the aqueous composition is between about 2 and about 11 (e.g., between about 4 and about 9).

[0042] As used herein, the term "colloidal dispersion" refers to a heterogeneous system with a dispersed phase and a dispersion medium, i.e., microscopically dispersed insoluble particles are suspended in another substance (e.g., aqueous compositions such as water or aqueous solutions). Examples of colloidal dispersions herein are hydrocolloids. The terms "dispersant" and "dispersion agent" are used interchangeably herein to refer to materials that promote the formation and / or stability of dispersions. "Dispersion" herein refers to the action of preparing a dispersion of a material in an aqueous liquid. As used herein, the term "latex" (and similar terms) refers to a dispersion of one or more types of polymer particles in water or an aqueous solution. In some aspects, latex is an emulsion containing dispersed particles. "Emulsion" herein is a dispersion of tiny droplets of a liquid in another liquid, in which these droplets are insoluble or immiscible (e.g., non-polar substances such as oils or other organic liquids such as alkanes, in polar liquids such as water or aqueous solutions).

[0043] In some aspects of the present disclosure, the glucan ester derivatives can provide stability for dispersions or emulsions. The "stability" (or "stable" peculiarity) of the dispersions or emulsions herein is, for example, after the initial preparation of the dispersions or emulsions, the dispersed particles of the dispersions or the liquid droplets (emulsions) dispersed in another liquid keep dispersing (for example, about or at least about 70, 75, 80, 85, 90, 95, 96, 97, 98, 99 or 100wt% of the particles of the dispersions or the liquid droplets of the emulsions are in a dispersed state) for about or at least about 0.5, 1, 2, 4, 6, 9, 12, 18, 24, 30 or 36 months. The ability of the time period that a stable dispersion or emulsion can resist all emulsification, sedimentation, flocculation, and / or coalescence of the dispersed / emulsified material.

[0044] "Soluble", "water-soluble", "water-soluble" (and similar terms) glucan ester derivatives herein dissolve (or significantly dissolve) in water or other aqueous conditions, optionally wherein the aqueous conditions are further characterized by having a pH of 4-9 (e.g., pH 6-8) and / or a temperature of about 1°C to 130°C (e.g., 20°C-25°C). In contrast, "insoluble", "water-insoluble", "water-insoluble", etc. glucan ester derivatives do not dissolve under these conditions. In some aspects, less than 1.0 gram (e.g., undetectable amount) of the water-insoluble glucan ester derivative dissolves in 1000 milliliters of such aqueous conditions (e.g., water at 23°C).

[0045] As used herein, the term "viscosity" refers to a measurement of the degree to which a fluid (aqueous or non-aqueous) resists forces tending to cause it to flow. Various viscosity units that may be used herein include, for example, centipoise (cP, cps) and Pascal seconds (Pa·s). One centipoise is one hundredth of a poise; one poise is equal to 0.100 kg·m -1 ·s -1 . In some aspects, viscosity can be reported as "intrinsic viscosity" (IV, η, in dL / g); the term refers to a measure of the contribution of a dextran polymer to the viscosity of a liquid (e.g., a solution) containing the dextran polymer. IV measurements herein can be obtained, for example, using any suitable method, as disclosed in U.S. Patent Application Publication Nos. 2017 / 0002335, 2017 / 0002336, or 2018 / 0340199, or Weaver et al. (J. Appl. Polym. Sci. [Journal of Applied Polymer Science] 35: 1631-1637) or Chun and Park (Macromol. Chem. Phys. [Major in Chemistry and Physics] 195: 701-711), all of which are incorporated herein by reference. For example, IV can be measured in part by dissolving the dextran polymer (optionally at about 100° C. for at least 2, 4, or 8 hours) in DMSO with about 0.9 to 2.5 wt % (e.g., 1, 2, 1-2 wt %) LiCl. IV herein can optionally be used as a relative measure of molecular weight.

[0046] The terms "polar organic solvent" and "water miscible organic solvent" (and similar terms) are used interchangeably herein. Polar organic solvents are capable of dissolving in water or aqueous solutions. Therefore, polar organic solvents do not separate into different phases when added to water or aqueous solutions. Polar organic solvents contain carbon and at least one heteroatom (i.e., non-carbon or non-hydrogen atom), such as oxygen, nitrogen, sulfur, or phosphorus. This is in contrast to non-polar organic solvents, which typically contain only carbon and hydrogen atoms. Polar organic solvents typically have a dielectric constant greater than about 4. Polar organic solvents contain dipoles due to polar bonds.

[0047] The term "aprotic polar organic solvent" (and similar terms) herein refers to a polar organic solution that does not have suitably labile hydrogen atoms that can form hydrogen bonds. Aprotic polar organic solvents do not contain hydrogen atoms bonded to atoms having electronegative properties; for example, there are no OH, NH, or SH bonds.

[0048] The term "protic polar organic solvent" (and similar terms) herein refers to a polar organic solution having one or more suitably labile hydrogen atoms that can form hydrogen bonds. Protic polar organic solvents typically contain hydrogen atoms bonded to atoms having electronegative properties; for example, one or more OH, NH, and / or SH bonds are present.

[0049] The term "home care product" and similar terms typically refer to products, goods and services related to the treatment, cleaning, care, and / or conditioning of the home and its interiors. The foregoing includes, for example, chemicals, compositions, products or combinations thereof having applications in such care.

[0050] The terms "fabric", "textile", "cloth" and the like are used interchangeably herein to refer to a woven material having a network of natural and / or artificial fibers. Such fibers may be in the form of, for example, threads or yarns.

[0051] "Fabric care composition" and like terms refer to any composition suitable for treating fabrics in some manner. Examples of such compositions include laundry detergents and fabric softeners, which are examples of laundry care compositions.

[0052] Typically, a "detergent composition" herein comprises at least a surfactant (detergent compound) and / or a builder. A "surfactant" herein refers to a substance that tends to reduce the surface tension of a liquid in which the substance is dissolved. Surfactants can be used, for example, as detergents, wetting agents, emulsifiers, foaming agents and / or dispersants.

[0053] The terms "heavy duty detergent," "all-purpose detergent," and the like are used interchangeably herein to refer to detergents that can be used for routine washing of white and colored textiles at any temperature. The terms "light duty detergent," "delicate fabric detergent," and the like are used interchangeably herein to refer to detergents that can be used to care for delicate fabrics such as viscose, wool, silk, microfiber, or other fabrics that require special care. "Special care" can include conditions such as use of excess water, low agitation, and / or no bleaching.

[0054] The terms "fabric softener", "fabric conditioner" and the like herein refer to compositions (such as in liquid or solid form) that deposit lubricants and / or other surface modifying ingredients onto fabrics, for example to help maintain the softness of the fabrics and / or to provide other beneficial characteristics to the fabrics (e.g., lubricity, antistatic properties, anti-cling properties and / or anti-wrinkling properties). Fabric softeners herein are typically applied to fabrics after the fabrics have been washed with a laundry detergent, usually while the fabrics are being rinsed.

[0055] The term "personal care product" and similar terms typically refer to products, goods and services related to the treatment, cleaning, washing, care or conditioning of a person. The foregoing includes, for example, chemicals, compositions, products or combinations thereof having applications in such care.

[0056] An "oral care composition" herein is any composition suitable for treating soft or hard surfaces in the oral cavity, such as dental (teeth) and / or gingival surfaces.

[0057] The term "ingestible product", "ingestible composition" etc. refers to any substance that can be taken orally (i.e., through the mouth) alone or together with another substance, whether or not intended to be eaten. Therefore, ingestible products include food products / beverage products. "Food products / beverage products" refers to any edible product intended for human or animal consumption (e.g., for nutritional purposes), including solid, semi-solid or liquid. "Food" herein may optionally be referred to as, for example, "foodstuff", "food product", or other similar terms. "Inedible product" ("inedible composition") refers to any composition that can be taken by the mouth except for food or beverage consumption purposes. Examples of inedible products herein include supplements, health supplements, functional food products, pharmaceutical products, oral care products (e.g., dentifrice, mouthwash) and cosmetics such as sweetened lipsticks. "Pharmaceutical product", "medicine", "medication", "drug" or similar terms herein refer to compositions used to treat diseases or injuries and can be administered enterally or parenterally.

[0058] The term "medical product" and similar terms typically refer to products, goods, and services related to the diagnosis, treatment, and / or care of patients.

[0059] The term "industrial product" and similar terms typically refer to products, goods, and services that are used in industrial and / or institutional settings, but not typically by individual consumers.

[0060] The terms "flocculant", "flocculant reagent", "flocculant composition", "flocculating agent", etc. herein refer to substances that can promote the aggregation / agglomeration / agglomeration of insoluble particles suspended in water or other aqueous liquids, thereby making these particles easier to remove by sedimentation / sedimentation, filtration, granulation, and / or other suitable means. Flocculation of particles can typically be carried out in the process of removing / separating particles from an aqueous suspension. In some aspects, glucan ester derivatives can be used as flocculants.

[0061] The terms "film", "sheet" and similar terms herein refer to thin materials that are usually visually continuous. The film may be included on the material as a layer or coating, or may be separate (e.g., not attached to the material surface; independent). "Coating" (and similar terms) as used herein refers to a layer covering the surface of a material. The term "uniform thickness" as used herein to characterize a film or coating may, for example, refer to a continuous region having a standard deviation of thickness of (i) at least 20% of the total film / coating area and (ii) less than about 50 nm. The term "continuous layer" means a layer of a composition applied to at least a portion of a substrate, wherein the dry layer of the composition covers ≥99% of the surface (the layer has been applied to the surface), and the voids in the layer exposing the substrate surface are less than 1%. ≥99% of the surface (the layer has been applied to the surface) does not include any area of ​​the substrate to which the layer has not yet been applied. In some aspects, the coating herein may form a continuous layer. The coating composition (and similar terms) herein refers to all solid components that form a layer on a substrate, such as the dextran ester derivatives herein and optionally pigments, surfactants, dispersing agents, binders, crosslinking agents, and / or other additives.

[0062] In some aspects, the terms "fiber", "fibers", etc. herein refer to staple fibers (short-length fibers) and long fibers. The fibers herein may comprise α-1,3-glucan, natural fibers (e.g., cellulose, cotton, wool, silk), or synthetic fibers (e.g., polyester), or any other type of material disclosed herein that can form fibers.

[0063] As used herein, the terms "fibrids", "glucan fibrids", "fibrillated glucan", etc. may refer to non-granular, fibrous, or film-like glucan particles in which at least one of its three dimensions is of a smaller magnitude relative to the largest dimension. In some aspects, the glucan fibrids may have a fibrous and / or lamellar structure having a relatively large surface area when compared to glucan fibers. The surface area of ​​the fibrids herein may be, for example, about 5 to 50 m 2 / gram of material, wherein the largest dimension is about 10 to 1000 microns and the smallest dimension is 0.05 to 0.25 microns (the aspect ratio of the largest dimension to the smallest dimension is 40 to 20,000).

[0064] The terms "nonwoven", "nonwoven product", "nonwoven web" and the like herein refer to a web of separate fibers or filaments inserted in the middle in a random or unrecognizable manner. This is contrasted with weaving or woven fabrics, which have recognizable fiber or filament networks. In some respects, the nonwoven product comprises a nonwoven web that is combined or attached to another material such as a substrate or backing. In some respects, the nonwoven may further contain an adhesive or adhesive (reinforcer) that bonds adjacent nonwoven fibers together. Nonwoven adhesives or adhesives may be applied to, for example, nonwovens in dispersion / latex, solution, or solid form, and then typically the treated nonwoven is dried.

[0065] The term "coating" (and similar terms) herein is a type of coating composition that is a dispersion of a pigment in a suitable liquid (e.g., an aqueous liquid) that can be used to form an adherent coating when spread over a surface in a thin coat. A coating such as one applied to a surface can provide coloring / decoration, protection, and / or treatment (e.g., a primer) to the surface. In some aspects, a coating can optionally be characterized as a latex or latex coating by further comprising dispersed particles.

[0066] "Composite materials" herein include two or more components including compositions of the present disclosure (e.g., dextran ester derivatives). Typically, the components of the composite material resist separation, and one or more of the components exhibit enhanced and / or different properties compared to their individual properties outside the composite material (i.e., the composite material is not just a mixture, which is usually easily separated from its original components). Composite materials herein are generally solid materials and can be manufactured via, for example, extrusion or molding processes.

[0067] The terms "sequence identity," "identity," and the like as used herein with respect to polypeptide amino acid sequences (e.g., polypeptide amino acid sequences of glucosyltransferases) are as defined and determined in U.S. Patent Application Publication No. 2017 / 0002336, which is incorporated herein by reference.

[0068] As the feature of some embodiments, various polypeptide amino acid sequences are disclosed herein. It is possible to use or quote variants of these sequences with sequences disclosed herein having at least about 70%-85%, 85%-90% or 90%-95% homogeneity. Alternatively, variant amino acid sequences can have at least 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 99.5% homogeneity. The variant amino acid sequences have the same function / activity of the disclosed sequences, or have at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98% or 99% of the function / activity of the disclosed sequences.

[0069] The compositions herein (which are "dry" or "dried") typically have less than 6wt%, 5wt%, 4wt%, 3wt%, 2wt%, 1wt%, 0.5wt%, or 0.1wt% water contained therein.

[0070] The terms "percent by volume," "volume percent," "volume % (vol%)," "v / v %," and the like are used interchangeably herein. The volume percent of a solute in a solution can be determined using the formula: [(volume of solute) / (volume of solution)] x 100%.

[0071] The terms "percent by weight", "weight percentage (wt%)", "weight-weight percentage (%w / w)", etc. are used interchangeably herein. Weight percentage refers to the percentage of a material on a mass basis when the material is included in a composition, mixture, or solution.

[0072] The terms "weight / volume percent", "w / v%", etc. are used interchangeably herein. The weight / volume percent can be calculated as: ((mass of material [g]) / (total volume of material plus liquid in which the material is placed [mL])) x 100%. A material can be insoluble in the liquid (i.e., a solid phase in a liquid phase, such as in the case of a dispersion), or soluble in the liquid (i.e., a solute that dissolves in the liquid).

[0073] The term "isolated" means a substance (or process) that is in a form or in an environment that does not exist in nature. Non-limiting examples of isolated substances include any of the glucan ester derivatives disclosed herein. It is believed that the embodiments disclosed herein are synthetic / artificial (impossible to make or practice except for human intervention / involvement), and / or have non-naturally occurring properties.

[0074] As used herein, the term "increased" can refer to a quantity or activity that is at least about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 50%, 100%, or 200% greater than the quantity or activity compared with the increased quantity or activity. The terms "increased", "raised", "enhanced", "greater than", "improved", etc. are used interchangeably in this article.

[0075] Some aspects of the present disclosure relate to a composition comprising an ester derivative of a glucan, wherein the glucan has a degree of substitution (DoS) of up to about 3.0 substituted by at least one cationic organic group (cationic acyl group) ester-linked to the glucan. Cationic glucan ester derivatives / compounds are thus disclosed. However, some aspects relate to a composition comprising an ester derivative of a glucan, wherein the glucan has a DoS of up to about 3.0 substituted by at least two organic groups individually ester-linked to the glucan, wherein (i) at least one of these organic groups is a cationic organic group, and (ii) at least one of these organic groups is a hydrophobic organic group. "Ester-linked individually" means that at least two of the organic groups of (i) and (ii) are each linked to the glucan via their own respective ester bonds. Since the glucan ester derivatives can be characterized in some aspects as having at least one cationic ester group and at least one hydrophobic ester group, this type of glucan ester can optionally be characterized as amphiphilic.

[0076] Glucan ester derivatives herein can be, for example, alpha-glucan ester derivatives. The glycosidic bond of the alpha-glucan ester derivatives herein is typically about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 100% alpha-glycosidic bond. The example of suitable alpha-glucan ester derivatives includes alpha-1,3-glucan, alpha-1,6-glucan and alpha-1, the ester derivative of 4-glucan.

[0077] In some aspects, the α-glucan ester comprises about or at least about 50%, 60%, 70%, 80%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5%, or 100% α-1,3-glycosidic bonds (i.e., the ester is an α-1,3-glucan ester). Thus, in some aspects, the α-glucan ester has about or less than about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% of glycosidic bonds that are not α-1,3. Typically, most or all of the glycosidic bonds that are not α-1,3 are α-1,6. In some aspects, the α-glucan ester has no branch points or has less than about 5%, 4%, 3%, 2%, or 1% (as a percentage of glycosidic bonds in the α-glucan) branch points.

[0078] In some aspects, the DPw, DPn, or DP of the α-glucan portion of the α-1,3-glucan ester can be about, at least about, or less than about 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 25, 50, 75, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2500, 3000, 3500, or 4000. The DPw, DPn, or DP can optionally be expressed as a range between any two of these values. By way of example only, DPw, DPn, or DP may be about 50-1600, 100-1600, 200-1600, 300-1600, 400-1600, 500-1600, 600-1600, 700-1600, 50-1250, 100-1250, 200-1250, 300-1250, 400-1250, 500-1250, 600-1250, 700-1600 -1250, 50-1000, 100-1000, 200-1000, 300-1000, 400-1000, 500-1000, 600-1000, 700-1000, 50-900, 100-900, 200-900, 300-900, 400-900, 500-900, 600-900, 700-900, 600-800, or 600-750. By way of further example only, DPw, DPn, or DP can be about 15-100, 25-100, 35-100, 15-80, 25-80, 35-80, 15-60, 25-60, 35-60, 15-55, 25-55, 35-55, 15-50, 25-50, 35-50, 35-45, 35-40, 40-100, 40-80, 40-60, 40-55, 40-50, 45-60, 45-55, 45-50, 15-35, 20-35, 15-30, or 20-30. As further examples only, DPw, DPn, or DP may be about 100-600, 100-500, 100-400, 100-300, 200-600, 200-500, 200-400, or 200-300.In some aspects, the α-glucan portion of the α-1,3-glucan ester can have a high molecular weight as reflected by a high intrinsic viscosity (IV); for example, the IV can be about or at least about 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 6-8, 6-7, 6-22, 6-20, 6-17, 6-15, 6-12, 10-22, 10-20, 10-17, 10-15, 10-12, 12-22, 12-20, 12-17, or 12-15 dL / g (for comparison purposes, note that the IV of an α-glucan having at least 90% (e.g., about 99% or 100%) α-1,3 linkages and a DPw of about 800 has an IV of about 2-2.5 dL / g). IV herein can be measured, for example, using an α-glucan polymer dissolved in DMSO with about 0.9 to 2.5 wt% (e.g., 1, 2, 1-2 wt%) LiCl. The molecular weight of the α-1,3-glucan ester herein can be calculated, for example, based on any of the aforementioned α-1,3-glucan DPw, DPn, or DP values, further taking into account the DoS of the ester and the type of one or more ester groups; such a molecular weight can be about, at least about, or less than about the calculated value (this model of molecular weight calculation can be applied to any other polysaccharide / glucan ester derivative disclosed herein).

[0079] The α-1,3-glucan portion of the α-1,3-glucan ester derivatives herein can be as disclosed, for example, in the following (e.g., molecular weight, bond pattern, and / or production method): U.S. Patent Nos. 7,000,000, 8,871,474, 1,0301,604, or 1,026,0053, or U.S. Patent Application Publication Nos. 2019 / 0112456, 2019 / 0078062, 20 19 / 0078063, 2018 / 0340199, 2018 / 0021238, 2018 / 0273731, 2017 / 0002335, 2015 / 0232819, 2015 / 0064748, 2020 / 0165360, 2020 / 0131281 or 2019 / 0185893, each of which is incorporated herein by reference. α-1,3-glucan can be produced, for example, by an enzymatic reaction comprising at least water, sucrose and a glucosyltransferase for synthesizing α-1,3-glucan. Glucosyltransferases, reaction conditions and / or methods that are expected to be useful for producing insoluble α-glucans can be as disclosed in any of the aforementioned references.

[0080] In some aspects, the glucosyltransferase used to produce the α-1,3-glucan portion of the α-1,3-glucan ester derivatives herein can comprise a glucosyltransferase that binds to amino acid residues 55-960 of SEQ ID NO: 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 26, 28, 30, 34, or 59, or residues 55-960 of SEQ ID NO: 4, residues 54-957 of SEQ ID NO: 65, residues 55-960 of SEQ ID NO: 30, residues 55-960 of SEQ ID NO: 28, or residues 55-960 of SEQ ID NO: 31. NO: residues 55-960100% identical or at least 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 98.5%, 99%, or 99.5% identical to amino acid sequences of NO: 20, and having glucosyltransferase activity; these amino acid sequences are disclosed in U.S. Patent Application Publication No. 2019 / 0078063, which is incorporated herein by reference. It should be noted that the glucosyltransferase comprising SEQ ID NO: 2, 4, 8, 10, 14, 20, 26, 28, 30, 34, or amino acid residues 55-960 of SEQ ID NO: 4, residues 54-957 of SEQ ID NO: 65, residues 55-960 of SEQ ID NO: 30, residues 55-960 of SEQ ID NO: 28, or residues 55-960 of SEQ ID NO: 20 can synthesize insoluble α-glucan containing at least about 90% (about 100%) α-1,3 linkages.

[0081] In some aspects, the alpha-glucan ester comprises about or at least about 50%, 60%, 70%, 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5% or 100% alpha-1,6-glycosidic bonds (i.e., the ester is an alpha-1,6-glucan ester or a dextran ester). In some aspects, substantially straight-chain dextran esters may comprise 5%, 4%, 3%, 2%, 1%, 0.5% or less glycosidic branches (straight-chain dextran esters have 100% alpha-1,6 bonds). If present, the glycosidic branches from the dextran ester are typically shorter, with a length of one (side chain), two, or three glucose monomers. In some aspects, the dextran ester can contain about, or less than about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% α-1,4, α-1,3 and / or α-1,2 glycosidic bonds. Typically, such bonds exist entirely or almost entirely as branch points from α-1,6-glucans.

[0082] For example, the dextran portion of the dextran ester derivatives herein can have α-1,2, α-1,3, and / or α-1,4 branches. In some aspects, about, at least about, or less than about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 30%, 35%, 40%, 45%, 50%, 2-25%, 2-20% of all glycosidic bonds of the branched dextran ester. , 2-15%, 2-10%, 5-25%, 5-20%, 5-15%, 5-10%, 7-13%, 8-12%, 9-11%, 10-25%, 10-20%, 10-15%, 10-22%, 12-20%, 12-18%, 14-20%, 14-18%, 15-18%, or 15-17% are α-1,2, α-1,3, and / or α-1,4 glycosidic branch bonds. Such branches are typically mostly (>90% or>95%) or all (100%) single glucose monomers in length. In some aspects, dextran with α-1,2-branching can be produced enzymatically according to the procedures in U.S. Patent Application Publication No. 2017 / 0218093 or 2018 / 0282385 (both of which are incorporated herein by reference), wherein, for example, α-1,2-branching enzymes such as GTFJ1 8T1 or GTF9905 can be added during or after dextran production. In some aspects, any other enzyme known to produce α-1,2-branching can be used. Dextran with α-1,3-branching can be prepared, for example, as disclosed in Vuillemin et al. (2016, J.Biol Chem. [Journal of Biological Chemistry] 291: 7687-7702) or International Patent Application Publication No. WO 2021 / 007264, which is incorporated herein by reference.

[0083] The dextran portion of the dextran ester derivatives herein can have, for example, about, at least about, or less than about 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 85, 90, 95, 100, 105, 110, 150, 200, 250, 300, 400, 500, 1000, 1500, 2000, 2500, 3000, 4000, 5000, 6000, 8-20, 8-30, 8-100, 8-50, 8-40, 8-50, 8-60, 8-70, 8-80, 8-90, 8-100, 8-150, 8-150, 8-150, 8-150, 8-150, 8-150, 8-1 -8, 4-5, 4-6, 4-7, 4-8, 5-6, 5-7, 5-8, 6-7, 6-8, 7-8, 90-120, 95-120, 100-120, 105-120, 110-120, 115-120, 90-115, 95-115, 100-115, 105-115, 110-11 5, 90-110, 95-110, 100-110, 105-110, 90-105, 95-105, 100-105, 90-100, 95-100, 90-95, 85-95, 85-90, 5-100, 5-250, 5-500, 5-1000, 5-1500, 5-2000, 5-2500, 5-3000, 5-4000, 5-5000, 5-6000, 10-100, 10-250, 10-500, 10-1000, 10-1500, 10-2000, 10-2500, 10-3000, 10-4000, 10-5000, 10-6000, 25-10 0, 25-250, 25-500, 25-1000, 25-1500, 25-2000, 25-2500, 25-3000, 25-4000, 25-5000, 25-6000, 50-100, 50-250, 50-500, 50-1000, 50-1500, 50-2000, 50-2500, 50-3000, 50-4000, 50-5000, 50-6000, 100-100, 100-250, 100-400, 100-500, 100-1000, 100-1500, 100-2000, 100-2500, 100-3000, 100-4000 、100-5000、100-6000、250-500、250-1000、250-1500、250-2000、250-2500、250-3000、250-4000、250-5000、250-6000、300-2800、300-3000、350-2800、350-3000, 500-1000, 500-1500, 500-2000, 500-2500, 500-2800, 500-3000, 500-4000, 500-5000, 500-6000, 600-1550, 600-1850, 600-2000, 600-2500, 600-3000, 750-1000, 750-1250, 750-1500, 750-2000, 750-250 -2000, 1000-1500, 1000-2000, 1000-2500, 1000-3000, 1000-4000, 1000-5000, 1000-6000, or 1100-1300 DPw, DPn, or DP. In some aspects, the molecular weight (e.g., Mw or Mn) of the dextran portion of the dextran ester derivative can be about, at least about, or less than about 0.1, 0.125, 0.15, 0.175, 0.2, 0.24, 0.25, 0.5, 0.75, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 175, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, 500, 510, 520, 530, 540, 550 、160、170、180、190、200、0.1-0.2、0.125-0.175、0.13-0.17、0.135-0.165、0.14-0.16、0.145-0.155、10-80、20-70、30-60、40-50、50-200、60-200、70-200、80-200、90-200、100-200、110-200、 120-200, 50-180, 60-180, 70-180, 80-180, 90-180, 100-180, 110-180, 120-180, 50-160, 60-160, 70-160, 80-160, 90-160, 100-160, 110-160, 120-160, 50-140, 60-140, 70-140, 80-140, 90-140 、100-140、110-140、120-140、50-120、60-120、70-120、80-120、90-120、90-110、100-120、110-120、50-110、60-110、70-110、80-110、90-110、100-110、50-100、60-100、70-100、80-100、90-100、In some aspects, the molecular weight (e.g., Mw or Mn) of the dextran portion of the dextran ester derivative can be, for example, about, at least about, or less than about 1, 5, 7.5, 10, 12.5, 15, 20, 30, 40, 50, 60, 70, 80, 90, 100, 150, 200, 250, 300, 400, 500, 600, 700, 800, 900, 1000, 1250, 1500, 1750, 2000, 1-2000, 1-1 ... -1000, 1-500, 1-400, 1-300, 1-200, 1-100, 1-50, 10-2000, 10-1000, 10-500, 10-400, 10-300, 10-200, 10-100, 10-50, 20-2000, 20-1000, 20-500, 20-400, 20-300, 20-200, 20-100, 20-50, 30-2000, 30-1000 , 30-500, 30-400, 30-300, 30-200, 30-100, 30-50, 40-2000, 40-1000, 40-500, 40-400, 40-300, 40-200, 40-100, 40-50, 50-2000, 50-1000, 50-500, 50-400, 50-300, 50-200, 100-2000, 100-1000, 100-500, 1 10-20, 10-30, 15-25, 15-30, 40-60, 45-55, 190-210, or 290-310 kDa. The molecular weight of the dextran ester herein can be calculated, for example, based on any of the aforementioned dextran DPw, DPn, DP, or Dalton values, further considering the DoS of the ester and the type of one or more ester groups; such a molecular weight can be about, at least about, or less than about any of the above molecular weight values ​​or ranges. For example, any of the foregoing DPw, DPn, DP, or Dalton values ​​can characterize the dextran herein before or after the dextran has been optionally branched (e.g., α-1,2 and / or α-1,3).

[0084] The dextran portion of the dextran ester derivatives herein can be as disclosed, for example (e.g., molecular weight, bond / branching pattern, production method) in U.S. Patent Application Publication Nos. 2016 / 0122445, 2017 / 0218093, 2018 / 0282385, 2020 / 0165360, or 2019 / 0185893, each of which is incorporated herein by reference. In some aspects, the ester-derivatized dextran herein can be a dextran produced in a suitable reaction comprising glucosyltransferase (GTF) 0768 (SEQ ID NO: 1 or 2 of US 2016 / 0122445), GTF 8117, GTF 6831, or GTF 5604 (the latter three GTF enzymes are SEQ ID NO: 30, 32, and 33 of US2018 / 0282385, respectively), or a GTF comprising an amino acid sequence that is at least 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, or 99% identical to the amino acid sequence of GTF 0768, GTF 8117, GTF 6831, or GTF 5604.

[0085] In some aspects, the α-glucan part of the α-glucan ester derivative can be in the form of a graft copolymer, such as disclosed in U.S. Patent Application Publication Nos. 2020 / 0165360, 2019 / 0185893, or 2020 / 0131281, which are incorporated herein by reference. The graft copolymer may include dextran (as a backbone) and α-1,3-glucan (as one or more side chains), wherein the latter component has been grafted onto the former component; typically, this graft copolymer is produced by using dextran or α-1,2- and / or α-1,3-branched dextran as a primer for α-1,3-glucan synthesis by α-1,3-glucan-producing glucosyltransferase as described above. One or more α-1,3-glucan side chains of the α-glucan graft copolymer herein may be α-1,3-glucan as disclosed in the present invention. The dextran backbone of the α-glucan graft copolymer herein can be a dextran as disclosed herein or an α-1,2- and / or α-1,3-branched dextran. In some aspects, the α-glucan graft copolymer can comprise: (A) an α-1,6-glucan backbone (100% α-1,6-linked before α-1,2 and / or α-1,3 branches), which (i) has been branched (e.g., backbone total) with about 10%-22% (e.g., about 12%-20%, 12%-18%, 14%-20%, 14%-18%, 15%-18%, 15%-17%, or 16%) α-1,2 and / or α-1,3 bonds (i.e., α-1,2,6 and / or α-1,3,6) comprising a total of about 82%-86% or 84% α-1,6 linkages and about 14%-18% or 16% α-1,2 and / or α-1,3 linkages) and (ii) having an Mw of about 15-25, 15-22.5, 17-25, 17-22.5, 18-22, or 20 kDa, and (B) one or more (e.g., two, three, four, five, or six) α-1,3-glucan side chains extending from one or more of the α-1,2 and / or α-1,3 branches; such graft copolymers are typically water-insoluble.

[0086] In some aspects, the α-glucan ester comprises about or at least about 50%, 60%, 70%, 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5%, or 100% α-1,4-glycosidic bonds (i.e., the ester is an α-1,4-glucan ester). Thus, in some aspects, the α-1,4-glucan ester has about or less than about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% of glycosidic bonds that are not α-1,4. Examples of α-1,4-glucans herein include amylose, amylopectin, and starch. For example, alpha-1,4-glucans such as starch can be derived from vegetable (eg, potato, cassava, pea, palm) or cereal (eg, corn, wheat, rice, barley) sources.

[0087] In some aspects, the DPw, DPn, or DP of the α-1,4-glucan portion of the α-1,4-glucan ester derivative can be about, at least about, or less than about 10, 25, 50, 75, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2500, 3000, 3500, or 4000. The DPw, DPn, or DP can optionally be expressed as a range between any two of these values. In some aspects, the DPw, DPn, or DP of the α-1,4-glucan portion of the α-1,4-glucan ester derivative can be as disclosed above for α-1,3-glucan or α-1,6-glucan.

[0088] Glucan ester derivatives herein can be, for example, β-glucan ester derivatives. The glycosidic bond of β-glucan ester derivatives herein is typically about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 100% β-glycosidic bond. The example of suitable β-glucan ester derivatives includes β-1,3-glucan (for example, laminarin, paramylon, curdlan), β-1,4-glucan (cellulose) and β-1, the ester derivative of 6-glucan. In some respects, the glucan ester herein is not β-glucan ester, and / or does not include β-glycosidic bond.

[0089] In some aspects, the β-glucan ester comprises about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5%, or 100% β-1,4-glycosidic bonds (i.e., the ester is a β-1,4-glucan ester). In some aspects, the DPw, DPn, or DP of the β-1,4-glucan portion of the β-1,4-glucan ester derivative can be about or at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 75, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2500, 3000, 3500, or 4000. The DPw, DPn, or DP can optionally be expressed as a range between any two of these values ​​(e.g., 1000-2000, 1300-1700, 1400-1600). In some aspects, the DPw, DPn, or DP of the β-1,4-glucan portion of the β-1,4-glucan ester derivative can be as disclosed above for α-1,3-glucan or α-1,6-glucan. In some aspects, the glucan ester herein is not a β-1,4-glucan ester, and / or does not contain a β-1,4-glycosidic bond.

[0090] In some aspects, the β-glucan ester comprises about or at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5%, or 100% β-1,3-glycosidic bonds (i.e., the ester is a β-1,3-glucan ester). In some aspects, for example, the DPw, DPn, or DP of the β-1,3-glucan portion of the β-1,3-glucan ester derivative can be about, at least about, or less than about 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65 9, 30, 40, 50, 60, 70, 80, 90, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2500, 3000, 3500 、4000、3-15、3-20、3-25、3-30、5-15、5-20、5-25、5-30、10-15、10-20、10-25、10-30、15-17、15-18、15-19、15-20、15-21、15-22、15-23、15-24、15-25、15-30、1 In some aspects, the DPw, DPn, or DP of the β-1,3-glucan portion of the β-1,3-glucan ester derivative can be as disclosed above for α-1,3-glucan or α-1,6-glucan.

[0091] In some additional or alternative aspects of this invention, the ester derivative can be a soybean polysaccharide ester derivative. In some aspects, the soybean polysaccharide part of the soybean polysaccharide ester derivative can be as disclosed in U.S. Patent Application Publication No. 2018 / 0079832, which is incorporated herein by reference. Therefore, within the scope that the technician considers appropriate, any feature of the present disclosure about the glucan ester derivative can also characterize the embodiment in which the soybean polysaccharide ester derivative is used. For example, within the scope that the technician considers appropriate, the term "glucan ester derivative" (and similar terms) as used in the present disclosure can be optionally replaced with the term "soybean polysaccharide ester derivative".

[0092] In some aspects of the present disclosure, the ester derivatives of polysaccharides / glucans may have a degree of substitution (DoS) of up to about 3.0 (e.g., 0.001 to 3.0) substituted by at least two organic groups attached to the glucan individual esters, wherein (i) at least one of these organic groups is a cationic organic group (cationic acyl), and (ii) at least one of these organic groups is a hydrophobic organic group (hydrophobic acyl). However, in some aspects, the ester derivatives of polysaccharides / glucans may have a DoS of up to about 3.0 (e.g., 0.001 to 3.0) substituted by at least one cationic organic group (cationic acyl) attached to the polysaccharide / glucan ester.

[0093] The DoS of the dextran substituted with at least one cationic organic group and at least one hydrophobic organic group herein (or, optionally, the "total DoS" in this regard) can be, for example, about, at least about, or up to about 0.001, 0.0025, 0.005, 0.01, 0.02, 0.025, 0.03, 0.04, 0.05, 0.06, 0.07, 0.075, 0.08, 0.09, 0.1, 0.0 .15, 0.2, 0.25, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, or 3.0 (DoS may optionally be expressed as a range between any two of these values). Some examples of DoS ranges in this article include 0.005-2.0, 0.005-1.9, 0.005-1.8, 0.005-1.7, 0.005-1.6, 0.005-1.5, 0.005-1.25, 0.005-1.0, 0.005-0.9, 0.005-0.8, 0.005-0.7, 0.005-0.6, 0.005-0.5, 0.01-2.0, 0.01-1.9, 0.01-1.8, 0.01-1.7, 0.01-1.6, 0.01-1.5, 0.01-1.25, 0.01-1.0, 0.01-0.9, 0.01-0.8, 0.01-0.7, 0.01-0.6, 0.01-0.5, 0.01-0.25, 0.01-0.1, 0.03-2.0, 0.03-1.9, 0.03-1.8, 0.03-1.7, 0.03-1.6, 0.03-1.5, 0.03-1.25, 0.03-1.0, 0.03-0.9, 0.03-0.8, 0.03-0.7, 0.03-0.6, 0.03-0.5, 0.03-0.25, 0.03-0.1, 0.05-2.0, 0.05-1.9, 0.05-1.8, 0.05-1.7, 0.05-1.6, 0.05-1.5, 0.05-1.25, 0.05-1.0, 0.05-0.9, 0.05-0.8, 0.05-0.7, 0 .05-0.6, 0.05-0.5, 0.1-2.0, 0.1-1.9, 0.1-1.8, 0.1-1.7, 0.1-1.6, 0.1-1.5, 0.1-1.25, 0.1-1.0, 0.1-0.9, 0.1-0.8, 0.1-0.7, 0.1-0.6, 0.1-0.5, 0.15-2.0, 0.15-1.9, 0.15-1.8, 0.15-1.7, 0.15-1.6, 0.15-1.5, 0.15-1.25, 0.15-1.0, 0.15-0.9, 0.15-0.8, 0.15-0.7, 0.15-0.6, 0.15-0.5, 0.2-2.0, 0.2-1.9, 0.2-1.8, 0.2-1.7, 0.2-1.6, 0.2-1.5, 0.2-1.25, 0 .2-1.0, 0.2-0.9, 0.2-0.8, 0.2-0.7, 0.2-0.6, 0.2-0.5, 0.25-2.0, 0.25-1.9, 0.25-1.8, 0.25-1.7, 0.25-1.6, 0.25-1.5, 0.25-1.25, 0.25-1.0, 0.25- 0.9, 0.25-0.8, 0.25-0.7, 0.25-0.6, 0.25-0.5, 0.3-2.0, 0.3-1.9, 0.3-1.8, 0.3-1.7, 0.3-1.6, 0.3-1.5, 0.3-1.25, 0.3-1.0, 0.3-0.9, 0.3-0.8, 0.3- 0.7, 0.3-0.6, 0.3-0.5, 0.4-2.0, 0.4-1.9, 0.4-1.8, 0.4-1.7, 0.4-1.6, 0.4-1.5, 0.4-1.25, 0.4-1.0, 0.4-0.9, 0.4-0.8, 0.4-0.7, 0.4-0.6 and 0.4-0.5. .

[0094] The DoS of the dextran substituted with at least one cationic organic group herein can be, for example, about, at least about, or up to about 0.001, 0.0025, 0.005, 0.01, 0.02, 0.025, 0.03, 0.04, 0.05, 0.06, 0.07, 0.075, 0.08, 0.09, 0.1, 0.15, 0.2, 0.25, 0. 3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, or 3.0 (DoS may optionally be expressed as a range between any two of these values). Some examples of DoS ranges in this article include 0.005-2.0, 0.005-1.9, 0.005-1.8, 0.005-1.7, 0.005-1.6, 0.005-1.5, 0.005-1.25, 0.005-1.0, 0.005-0.9, 0.005-0.8, 0.005-0.7, 0.005-0.6, 0.005-0.5, 0.01-2.0, 0.01-1.9, 0.01-1.8, 0.01-1. 7, 0.01-1.6, 0.01-1.5, 0.01-1.25, 0.01-1.0, 0.01-0.9, 0.01-0.8, 0.01-0.7, 0.01-0.6, 0.01-0.5, 0.01-0.25, 0.01-0.1, 0.03-2.0, 0.03-1.9, 0.03-1.8, 0.03-1.7, 0.03-1.6, 0.03-1.5, 0.03-1.25, 0.03-1.0, 0.03- 0.9, 0.03-0.8, 0.03-0.7, 0.03-0.6, 0.03-0.5, 0.03-0.25, 0.03-0.1, 0.05-2.0, 0.05-1.9, 0.05-1.8, 0.05-1.7, 0.05-1.6, 0.05-1.5, 0.05-1.25, 0.05-1.0, 0.05-0.9, 0.05-0.8, 0.05-0.7, 0.05-0.6, 0.05-0.5, 0.1- 2.0, 0.1-1.9, 0.1-1.8, 0.1-1.7, 0.1-1.6, 0.1-1.5, 0.1-1.25, 0.1-1.0, 0.1-0.9, 0.1-0.8, 0.1-0.7, 0.1-0.6, 0.1-0.5, 0.15-2.0, 0.15-1.9, 0.15-1.8, 0.15-1.7, 0.15-1.6, 0.15-1.5, 0.15-1.25, 0.15-1.0, 0.15-0.9, 0.15-0.8, 0.15-0.7, 0.15-0.6, 0.15-0.5, 0.2-2.0, 0.2-1.9, 0.2-1.8, 0.2-1.7, 0.2-1.6, 0.2-1.5, 0.2-1.25, 0.2-1.0, 0.2-0.9, 0.2-0.8, 0.2-0.7, 0.2-0.6, 0.2-0.5, 0.25-2.0, 0.25-1.9, 0.25-1.8, 0.25-1.7, 0.25-1.6, 0.25-1.5, 0.25-1.25, 0.25-1.0, 0.25-0.9, 0.25-0.8, 0 .25-0.7, 0.25-0.6, 0.25-0.5, 0.3-2.0, 0.3-1.9, 0.3-1.8, 0.3-1.7, 0.3-1.6, 0.3-1.5, 0.3-1.25, 0.3-1.0, 0.3-0.9, 0.3-0.8, 0.3-0.7, 0.3-0.6, 0.3-0.5, 0.4-2.0, 0.4-1.9, 0.4-1.8, 0.4-1.7, 0.4-1.6, 0.4-1.5, 0.4-1.25, 0.4-1.0, 0.4-0.9, 0.4-0.8, 0.4-0.7, 0.4-0.6 and 0.4-0.5.

[0095] The DoS of the dextran substituted with at least one cationic organic group herein can be, for example, about, at least about, or up to about 0.001, 0.0025, 0.005, 0.01, 0.02, 0.025, 0.03, 0.04, 0.05, 0.06, 0.07, 0.075, 0.08, 0.09, 0.1, 0.15, 0.2, 0.25, 0. 3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, or 3.0 (DoS may optionally be expressed as a range between any two of these values). Some examples of DoS ranges in this article include 0.005-2.0, 0.005-1.9, 0.005-1.8, 0.005-1.7, 0.005-1.6, 0.005-1.5, 0.005-1.25, 0.005-1.0, 0.005-0.9, 0.005-0.8, 0.005-0.7, 0.005-0.6, 0.005-0.5, 0.01-2.0, 0.01-1.9, 0.01-1.8, 0.01-1. 7, 0.01-1.6, 0.01-1.5, 0.01-1.25, 0.01-1.0, 0.01-0.9, 0.01-0.8, 0.01-0.7, 0.01-0.6, 0.01-0.5, 0.01-0.25, 0.01-0.1, 0.03-2.0, 0.03-1.9, 0.03-1.8, 0.03-1.7, 0.03-1.6, 0.03-1.5, 0.03-1.25, 0.03-1.0, 0.03- 0.9, 0.03-0.8, 0.03-0.7, 0.03-0.6, 0.03-0.5, 0.03-0.25, 0.03-0.1, 0.05-2.0, 0.05-1.9, 0.05-1.8, 0.05-1.7, 0.05-1.6, 0.05-1.5, 0.05-1.25, 0.05-1.0, 0.05-0.9, 0.05-0.8, 0.05-0.7, 0.05-0.6, 0.05-0.5, 0.1- 2.0, 0.1-1.9, 0.1-1.8, 0.1-1.7, 0.1-1.6, 0.1-1.5, 0.1-1.25, 0.1-1.0, 0.1-0.9, 0.1-0.8, 0.1-0.7, 0.1-0.6, 0.1-0.5, 0.15-2.0, 0.15-1.9, 0.15-1.8, 0.15-1.7, 0.15-1.6, 0.15-1.5, 0.15-1.25, 0.15-1.0, 0.15-0.9, 0.15-0.8, 0.15-0.7, 0.15-0.6, 0.15-0.5, 0.2-2.0, 0.2-1.9, 0.2-1.8, 0.2-1.7, 0.2-1.6, 0.2-1.5, 0.2-1.25, 0.2-1.0, 0.2-0.9, 0.2-0.8, 0.2-0.7, 0.2-0.6, 0.2-0.5, 0.25-2.0, 0.25-1.9, 0.25-1.8, 0.25-1.7, 0.25-1.6, 0.25-1.5, 0.25-1.25, 0.25-1.0, 0.25-0.9, 0.25-0.8, 0 .25-0.7, 0.25-0.6, 0.25-0.5, 0.3-2.0, 0.3-1.9, 0.3-1.8, 0.3-1.7, 0.3-1.6, 0.3-1.5, 0.3-1.25, 0.3-1.0, 0.3-0.9, 0.3-0.8, 0.3-0.7, 0.3-0.6, 0.3-0.5, 0.4-2.0, 0.4-1.9, 0.4-1.8, 0.4-1.7, 0.4-1.6, 0.4-1.5, 0.4-1.25, 0.4-1.0, 0.4-0.9, 0.4-0.8, 0.4-0.7, 0.4-0.6 and 0.4-0.5.

[0096] For example, any of the aforementioned DoS values ​​and / or ranges for (i) at least one cationic group and (ii) at least one hydrophobic group can be combined as appropriate to characterize the DoS characteristics of the glucan ester derivatives herein. In some aspects, any of the aforementioned values ​​and / or ranges for the total DoS can be combined as appropriate with any of the aforementioned DoS values ​​and / or ranges for (i) at least one cationic group and / or (ii) at least one hydrophobic group.

[0097] Regarding the polysaccharide ester derivatives herein as dextran derivatives, for example, since there are up to three hydroxyl groups in the glucose monomer unit of dextran, the total DoS of the dextran ester derivatives may be no higher than 3.0. It should be understood by those skilled in the art that since the dextran ester derivatives as disclosed herein have a DoS (e.g., between about 0.001 and about 3.0) of at least one type of organic group (acyl group) used in the ester bond (e.g., at least two types of organic groups in the ester bond, wherein at least one group is a cationic group and at least one group is a hydrophobic group), all substituents of the dextran ester derivatives cannot be only hydroxyl groups.

[0098] The ester derivatives of polysaccharides / glucans disclosed herein may be substituted with at least one cationic organic group (cationic acyl group) herein that is linked to a polysaccharide / glucan ester. For example, a glucan derivative as disclosed herein may be derivatized with one, two, three, or more different types of esterified cationic organic groups herein. In some aspects, at least one ester-linked cationic organic group comprises structure I:

[0099] wherein R1, R2 and R3 are each independently a group containing at least one carbon atom. The positions of R1, R2 and R3 in Structure I are generally not particularly important and are not intended to induce any particular stereochemistry.

[0100] Regarding the wavy line (variable cross section) of structure I, since the cationic organic group is connected to the dextran derivative ester herein and is therefore a cationic acyl group, it should be understood that the -N+R1R2R3 portion of structure I is bound to the glucose monomer unit of the dextran derivative via one or more carbon atoms (chain) via a carbonyl group (-CO-). This one or more carbon atoms (chain) may be referred to herein as -R c -. The carbonyl group converts the -Rc-N + The R1R2R3 moiety is attached to the oxygen atom of the now substituted hydroxyl group (i.e., the hydrogen atom is now replaced by an acyl group). Thus, Structure I may optionally be described as -CO-R c -N + When bound to the glucose monomer unit of glucan, it can be described as -C G -O G -CO-R c -N + R1R2R3, where -C G - represents the carbon atom of the glucose monomer unit, and -O G - represents the oxygen atom of the hydroxyl group of the glucose unit which is now substituted.

[0101] In some respects, R c (above) contains one (e.g., -CH2-), two (e.g., -CH2CH2-), three (e.g., -CH2CH2CH2-), four (e.g., -CH2CH2CH2-), five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, or more carbon atoms. For example, R c Can be fully or partially saturated. For example, R c For example, structure I can be described as -CO-CH2-N +R1R2R3, -CO-CH2CH2-N + R1R2R3, -CO-CH2CH2CH2-N + R1R2R3, or -CO-CH2CH2CH2CH2-N + R1R2R3.

[0102] For example, R c There may be one or more substitutions with hydroxyl groups (a hydrogen atom is replaced by another group). c may contain -CH2CH(OH)-; for example, structure I containing such Rc may be described as -CO-CH2CH(OH)-CH2-N + R1R2R3, -CO-CH2CH(OH)-CH2CH2-N + R1R2R3, -CO-CH2CH(OH)-CH2CH2CH2-N + R1R2R3, or -CO-CH2CH(OH)-CH2CH2CH2CH2-N + R1R2R3.

[0103] For example, R c Can have one or more branches. In some aspects, R c Can contain -CHR s -(CH2) p -, where R s is a side chain and p is 0, 1, 2, or 3. For example, R s It can be -CH3, -CH2CH3, -CH2CH2CH3, or -CH2CH2CH2CH3. For example, R s It can be -CH2CH2CH2CH2-N + H3 (i.e., lysine side chain), -CH2CH2CH2CH2-N + (CH3)3, CH2CH2-NH-C(N + H2)-NH2, -CH2CH2CH2-NH-C(N + H2)-NH2 (i.e., arginine side chain), or -CH2-IMD (i.e., histidine side chain, CH2 bonded to imidazole ring [IMD] carbon-4).

[0104] In some aspects, such as in any of the above structures / formulas, R1, R2, and R3 can each be as follows: R1, R2, and R3 can each be independently selected from, for example, -CH3, -CH2CH3, -CH2CH2CH3, or -CH2CH2CH2CH3 (for example, R1, R2, and R3 can each be -CH3). In some aspects, R1, R2, and R3 can each be independently selected from any of these aforementioned C1-C4 alkyl monohydroxy or dihydroxy substituted forms (for example, hydroxyethyl, such as -CH2CH2OH or -CH2(OH)CH3). In some aspects, R1, R2, and R3 can each be independently selected from any of the aforementioned C1-C4 alkyl and its monohydroxy or dihydroxy substituted form. In some aspects, R1 and R2 can be independently selected from any of the aforementioned C1-C4 alkyl and its monohydroxy or dihydroxy substituted form (for example, R1 and R2 can be -CH3), and R3 can be as follows: For example, R3 can be saturated or unsaturated. For example, R3 can be straight chain or branched. R3 can be, for example, an alkyl group, such as -(CH2)nCH3, wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 22, or 23 (e.g., C6-C22, C12-14, C10-C16, or C8-C18 alkyl); R3 can alternatively be an unsaturated form of any of these alkyl groups, as appropriate. In some aspects, R3 can be -CH2CH2CH2-NH-CO-CH2CH2CH2-(CH2) n -CH2CH2CH2CH3, wherein n is 0, 2, 4, 6, or 10.

[0105] As discussed above, it should be apparent that, in some aspects, the cationic organic group can comprise structure II:

[0106] wherein R1, R2 and R3 are each independently selected from a group comprising at least one carbon atom (e.g., any of the above R1, R2 and R3). cis -CH2-. Examples of Structure II herein have R1, R2, and R3 each being -CH3. It is understood that structure II is a cationic acyl group; additional examples of structure II herein include the acyl group (acyl portion) of any of the following betaine compounds: decylamidopropyl betaine, caprylyl betaine, cetylamidopropyl betaine, cetyl betaine, cocoamidoethyl betaine, cocoamidopropyl betaine, decylamidopropyl betaine, decyl betaine, isostearamidopropyl betaine, lauroamidopropyl betaine, lauryl betaine, myristylamidopropyl betaine, myristyl betaine, oleamidopropyl betaine, oleyl betaine, palmitoleamidopropyl betaine, palmitamidopropyl betaine, stearamidopropyl betaine, stearyl betaine, undecyl betaine, undecylenamidopropyl betaine.

[0107] The ester derivatives of polysaccharides / glucans disclosed herein can be substituted by at least one hydrophobic organic group (hydrophobic acyl) herein connected to the polysaccharide / glucan ester. For example, the glucan derivatives disclosed herein can be derivatized with one, two, three, or more different types of esterified hydrophobic acyl groups herein. The hydrophobic acyl group can be expressed as -CO-R', wherein R' is hydrophobic and comprises a chain having at least one carbon atom; the carbonyl group (-CO-) of the acyl group is connected to the polysaccharide / glucan monomer (e.g., glucose) via the oxygen atom of the monomer. R' can be, for example, straight chain, branched chain, or cyclic. R' can be saturated or unsaturated, and / or comprise, for example, up to 29 carbon atoms.

[0108] In some aspects, the hydrophobic acyl group may be referred to as a "C n "acyl" (or other similar terms), wherein n is an integer of 2 or greater and represents the number of carbon atoms in the acyl group, including the carbonyl carbon atom. n Acyl groups are typically straight chain and may be saturated or unsaturated. n The first carbon (carbon-1) of an acyl group is its carbonyl carbon. n The acyl group can be acetyl (C2), propionyl (C3), butyryl (C4), valeryl (C5), hexanoyl (C6), heptanoyl (C7), octanoyl (C8), nonanoyl (C9), decanoyl (C10), decanoyl (C11), octanoyl (C12), decanoyl (C13), octanoyl (C14), octanoyl (C15), decanoyl (C16), octanoyl (C17), octanoyl (C18), decanoyl (C19), decanoyl (C20), octanoyl (C21), octanoyl (C22), decanoyl (C23), decanoyl (C24), octanoyl (C25), octanoyl (C26), octanoyl (C27), octanoyl (C28), decano 10 ), undecanoyl (C 11 ), dodecanoyl (C 12 ), tridecanoyl (C 13 ), tetradecanoyl (C 14 ), pentadecanoyl (C 15 ), hexadecanoyl (C 16 ), heptadecayl (C 17 ), octadecanoyl (C 18), nonadecanoyl (C 19 ), eicosyl (C 20 ), eicosyl (C 21 ), behenyl (C 22 ), tricosyl (C 23 ), tetracosyl (C 24 ), pentadecanoyl (C 25 ), hexadecanoyl (C 26 ), C 27 , C 28 , C 29 , or C 30 Acyl. These specific C n Acyl is saturated. Common names of some of the acyl groups listed above are acetyl (acetyl or ethanoyl group), propionyl (propionyl or propanoyl group), butyryl (butanoyl or butanoyl group), valeryl (valeryl or pentanoyl group), caproyl (caproyl or hexanoyl group); enanthyl (enanthyl or heptanoyl group), caprylyl (caprylyl or octanoyl group), nonanoyl (pelargonyl or nonanoyl group), decanoyl (capryl or decanoyl group), lauroyl (dodecanoyl), myristyl (tetradecanoyl), palmityl (hexadecanoyl), stearyl (octadecanoyl), arachidyl (eicosanoyl), behenyl (behenyl), wood wax base (tetracosanoyl), and wax base (hexacosanoyl). In some aspects, acyl can be C 10 To C 14 Acyl, meaning that the acyl group can be C 10 , C 11 , C 12 , C 13 , or C 14 Any of the acyl groups (thus, the specific C n The scope nomenclature applies to the other C n In some aspects, the acyl group can be C2 to C 26 , C4 to C 20 , C6 to C 18 , C8 to C 18 , C 10 To C 18 , C 12 To C 18 , C6 to C 16 , C8 to C 16 , C10 To C 16 , C 12 To C 16 , C6 to C 14 , C8 to C 14 , C 10 To C 14 , C 12 To C 14 , C6 to C 12 , C8 to C 12 , or C 10 To C 12 Acyl.

[0109] In some respects, hydrophobic acyl can be undersaturated.Unsaturated acyl can comprise for example one, two, three, four, five, six or more double bonds.In some respects, unsaturated acyl can comprise one or more carbon (i) 4 and 5) across acyl, (ii) 5 and 6, (iii) 6 and 7, (iv) 8 and 9, (v) 9 and 10, (vi) 11 and 12, (vii) 12 and 13, (viii) 14 and 15, (ix) 15 and 16, (x) 16 and 17, (xi) 17 and 18, and / or (xii) 18 and 19 double bonds, wherein carbon number counts from the carbonyl carbon (i.e., carbon-1) of acyl.Some suitable combinations of the double bonds of acyl are reflected in the following list of unsaturated acyl.Although the double bonds of acyl can be cis or trans orientations herein, it is typically cis orientation. In some aspects, the unsaturated acyl group may be derived from (derivable from) a fatty acid. Examples of unsaturated acyl groups herein include (11Z, 14Z)-eicosadienoyl, (11Z, 14Z, 17Z)-eicosatoyl, (4Z)-hexadecenoyl, (4Z, 7Z, 10Z, 13Z, 16Z)-docosapentaenoyl, (4Z, 7Z, 10Z, 13Z, 16Z, 19Z)-docosahexaenoyl, (5Z, 8Z, 11Z, 14Z, 17Z)-eicosopentaenoyl, (5Z, 9Z, 12Z)- Octadecatrienoyl, (5Z, 9Z, 12Z, 15Z)-octadecatetraenoyl, (6Z, 9Z, 12Z, 15Z)-octadecatetraenoyl, (7Z, 10Z)-hexadecadienoyl, (7Z, 10Z, 13Z)-hexadecatrienoyl, (7Z, 10Z, 13Z, 16Z)-docosatetraenoyl, (7Z, 10Z, 13Z, 16Z)-docosapentaenoyl, (8E, 10E, 12Z)-octadecatrienoyl yl, (8Z,11Z,14Z)-eicosatetraenoyl, (8Z,11Z,14Z,17Z)-eicosatetraenoyl, (9Z)-octadec-9-ene-12-ynyl, (9Z,11E,13E)-octadecatrienoyl, (9Z,11E,13Z)-octadec-9,11,13-trienoyl, (9Z,12E)-hexadecadienoyl, (9Z,12E)-octadecadienoyl, (9Z,12Z)-octadec-9,1 2-diene-6-ynyl, (9Z,12Z,15Z)-octadec-9,12,15-triene-6-ynyl, (Z)-tetradec-7-enoyl, cis, cis-tetradec-5,8-dienoyl, cis-tetradec-5-enoyl, arachidonic acid, docosenoyl, dodecenoyl, tauropyl, heptatrienoyl, eicosenoyl, linoleoyl, myristenoyl, octadec-9-ynyl, octadecenoyl, palmitoleoyl and oleoyl.

[0110] In some aspects, the hydrophobic acyl group may include an aryl group. For example, the aryl acyl group may include a benzoyl group (-CO-C6H5), which may also be referred to as a benzoate group. In some aspects, the aryl acyl group may include a benzoyl group substituted with at least one halogen ("X"; e.g., Cl, F), an alkyl group, a haloalkyl group, an ether, a cyano group, or an aldehyde group, or a combination thereof, such as represented by the following structures III(a) to III(r):

[0111]

[0112] In some aspects, the hydrophobic acyl group can include a branched group. Examples of branched acyl groups herein include 2-methylpropanoyl, 2-methylbutanoyl, 2,2-dimethylpropanoyl, 3-methylbutanoyl, 2-methylvaleryl, 3-methylvaleryl, 4-methylvaleryl, 2,2-dimethylbutanoyl, 2,3-dimethylbutanoyl, 3,3-dimethylbutanoyl, 2-ethylbutanoyl and 2-ethylhexanoyl.

[0113] In some aspects, the polysaccharide / glucan ester derivatives of the present disclosure can be characterized as mixed esters by comprising at least one cationic ester group herein and at least one hydrophobic ester group herein. By way of example only, a mixed glucan ester can comprise a betaine acyl group herein (e.g., Structure II, wherein R1, R2, and R3 are each -CH3) (e.g., DoS is about 0.01-0.12, 0.03-0.1, 0.04-0.09, or 0.05-0.09) and (i) a C3 ester group herein. 10 To C 14 Acyl (e.g., C 12 In some aspects, the polysaccharide / glucan ester derivatives may include one or both of (i) an acyl group such as a lauroyl group and / or (ii) an aryl acyl group as a hydrophobic acyl group herein (e.g., a benzoyl group) (e.g., a DoS of about 0.2-1.0, 0.3-0.9, 0.4-0.8, or 0.5-0.8); optionally, such a mixed glucan ester may further include an acetyl group (e.g., a DoS of about 0.02-0.3). In some aspects, such a glucan ester may include α-1,2- and / or α-1,3-branched (e.g., about 15%-25% branched) α-1,6-glucan (e.g., about 10-70, 20-60, or 30-50 kDa) as its glucan component. Although in some aspects, the polysaccharide / glucan ester derivative does not include any other type of substituent group other than the ester group, in other aspects one or more other types of substituent groups may be present.

[0114] The hydrophobic acyl group of the polysaccharide / glucan ester derivatives herein can be as disclosed, for example, in U.S. Patent Application Publication Nos. 2014 / 0187767, 2018 / 0155455, or 2020 / 0308371, or International Patent Application Publication No. WO 2021 / 252575, each of which is incorporated herein by reference.

[0115] In some alternative aspects, the polysaccharide / glucan as disclosed herein can be derivatized with anionic organic groups and hydrophobic ester groups (i.e., anionic organic groups replace cationic ester groups or have anionic organic groups in addition to cationic ester groups). The hydrophobic ester group can be as disclosed, for example, herein (e.g., an ester group containing an aromatic group, such as benzoyl). The anionic organic group is typically connected to the polysaccharide / glucan via an ether or ester bond; the anionic organic group can optionally be characterized as an anionic ether group or anionic ester group. Examples of suitable anionic groups herein include carboxyalkyl (e.g., carboxymethyl) (which is an example of an ether group), and groups derived from cyclic organic anhydrides (e.g., succinate groups) (which is an example of an ester group). As an example only, the polysaccharide / glucan derivatives herein can have (i) carboxymethyl ether and benzoyl ester groups, or (ii) succinate and benzoyl ester groups. Suitable anionic groups may be as disclosed in, for example, U.S. Patent Application Publication Nos. 2014 / 0179913, 2016 / 0304629, 2020 / 0002646, 2021 / 0253977, 2018 / 0155455, or 2023 / 0192905, or International Patent Application Publication Nos. WO 2021 / 247810, WO 2022 / 178073, or WO 2022 / 178075, which are incorporated herein by reference. In the aforementioned alternative aspects, the DoS of the glucan having an anionic organic group herein may be as disclosed herein for, for example, a hydrophobic ester group or a cationic ester group.

[0116] In some alternative aspects, the polysaccharide / glucan as disclosed herein can be derivatized with anionic organic groups and cationic ester groups (i.e., anionic organic groups replace hydrophobic ester groups or anionic organic groups are present in addition to hydrophobic ester groups). The cationic ester groups can be, for example, as disclosed herein (e.g., cationic ester groups comprising structure I herein). The anionic organic groups are typically connected to the polysaccharide / glucan via ether or ester bonds; the anionic organic groups can optionally be characterized as anionic ether groups or anionic ester groups. Examples of suitable anionic groups herein include carboxyalkyl (e.g., carboxymethyl), and groups derived from cyclic organic anhydrides (e.g., succinate groups). By way of example only, the polysaccharide / glucan derivatives herein can have (i) carboxymethyl ether and structure I ester groups, or (ii) succinate and structure I ester groups. Suitable anionic groups can be, for example, as disclosed in the above-mentioned patent application references. In the aforementioned alternative aspects, the DoS of the dextran having anionic organic groups herein can be as disclosed herein for, for example, hydrophobic ester groups or cationic ester groups.

[0117] Some aspects of the present disclosure relate to a method of producing an ester derivative of a glucan herein. Such a method (ester derivatization method / reaction, or esterification method / reaction) may include: (a) contacting a glucan with at least two esterifying agents, wherein at least one of the esterifying agents comprises a cationic organic group (cationic acyl), wherein at least one of the esterifying agents comprises a hydrophobic organic group (hydrophobic acyl), wherein at least one cationic organic group and at least one hydrophobic organic group are esterified to the glucan, thereby producing an ester derivative of the glucan, wherein the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 substituted by the cationic organic group and the hydrophobic organic group, and (b) optionally, separating the ester derivative of the glucan produced in step (a). Thus, any glucan or other polysaccharide as disclosed herein may be added to an esterification method to produce any ester derivative herein.

[0118] For example, the esterification agent used in the ester derivatization method of the present disclosure can be a carboxylic acid containing any cationic acyl group as disclosed herein. It is understood that the terminal carbonyl group (-CO-) of the cationic acyl group is the carbonyl group of the -COOH group of the carboxylic acid containing the cationic acyl group; the use of the term "terminal" here is distinguished from any internal carbonyl group (if present) of the acyl group as disclosed herein. The carboxylic acid can be provided as a salt with an anion such as chloride, fluoride, or bromide, wherein the anion is bonded to one or more N of the carboxylic acid. + Partial countermeasure.

[0119] The esterifying agent used in the ester derivatization method of the present disclosure can be, for example, a carboxylic acid containing any hydrophobic acyl group as disclosed herein. It is understood that the terminal carbonyl group (-CO-) of the hydrophobic acyl group is the carbonyl group of the -COOH group of the carboxylic acid containing the hydrophobic acyl group.

[0120] The esterifying agent used in the ester derivatization method of the present disclosure can be, for example, an acyl halide (acid halide) comprising any acyl group as disclosed herein. The halide of the acyl halide herein can be, for example, a chloride, a fluoride, or a bromide. In some aspects, the esterifying agent used in the ester derivatization method can be, for example, an anhydride comprising any acyl group as disclosed herein. Some illustrative examples of anhydrides include aromatic anhydrides (aromatic anhydrides) (e.g., benzoic anhydride [benzoyl anhydride]), acetic anhydride, propionic anhydride, and butyric anhydride.

[0121] The concentration of the esterifying agent (for cationic esterification or hydrophobic esterification) in the esterification reaction herein can be, for example, about 10, 25, 50, 75, 100, 125, 150, 175, 200, 10-200, 25-200, 25-100, 10-25, 100-200, or 150-200 g / L.

[0122] The step of contacting the glucan with at least one esterifying agent is typically carried out under substantially anhydrous conditions. The substantially anhydrous esterification reaction herein does not contain water or contains less than about 0.05 wt%, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1.0 wt%, 1.1 wt%, 1.2 wt%, 1.3 wt%, 1.4 wt%, 1.5 wt%, 1.6 wt%, 1.7 wt%, 1.8 wt%, 1.9 wt%, or 2.0 wt% of water. The solvent used to contact the glucan with at least one esterifying agent can be, for example, a non-aqueous solvent in which the glucan can typically be dissolved. In some aspects, the non-aqueous solvent can be an organic solvent comprising N,N-dimethylacetamide (DMAc) (optionally with about 0.5%-5% LiCl), dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), pyridine, SO2 / diethylamine (DEA) / DMSO, LiCl / 1.3-dimethyl-2-imidazolidinone (DMI), DMSO / tetrabutyl-ammonium fluoride trihydrate (TBAF), N-methylpyrrolidone, dichloromethane, and / or N-methylmorpholine-N-oxide (NMMO). A dehydrating agent (e.g., tosyl chloride or dicyandiamide) can be optionally included in the contacting step herein.

[0123] For example, the contacting step can be performed in one esterification reaction (a "one-pot" reaction). In some aspects of the one-pot reaction, at least one cationic esterifying agent and at least one hydrophobic esterifying agent can be provided simultaneously in the reaction, or these reagents can be provided to the reaction sequentially (for example, one or more hydrophobic esterifying agents can be added first, followed by one or more cationic esterifying agents, or vice versa). In some aspects, the contacting step can be performed in at least two separate reactions, at least one of which uses at least one cationic esterifying agent and at least one of which uses at least one hydrophobic esterifying agent. The ester product of the first reaction can optionally be separated before entering another reaction. In some aspects, one or more reactions for cationic esterification can be performed, after which the ester product enters one or more reactions for hydrophobic esterification (or vice versa).

[0124] For example, the concentration of dextran in the esterification reaction herein can be about or at least about 10, 25, 50, 75, 100, 150, 200, 250, 300, 10-300, 10-250, 10-200, 10-50, 25-300, 25-250, 25-200, 25-50, 150-300, 150-250, or 150-200 g / L. The temperature of the esterification reaction herein can be, for example, about 50° C., 60° C., 70° C., 80° C., 90° C., 100° C., 110° C., 120° C., 130° C., 140° C., 150° C., 50° C.-150° C., 50° C.-140° C., 50° C.-130° C., 60° C.-150° C., 60° C.-140° C., 60° C.-130° C., 70° C.-150° C., 70° C.-140° C., 70° C.-130° C., 60° C.-80° C., or 110° C.-130° C. In some aspects, the esterification reaction can be carried out for about 1, 2, 3, 4, 5, 6, 7, 8, 1-8, 2-8, 1-6, or 2-6 hours. In some aspects, the pH of the esterification reaction can be about 8.5, 9.0, 9.5, 10.0, 10.5, 11.0, 11.5, or 12.

[0125] The esterified glucan derivative produced in one or more esterification reactions herein can be optionally separated. In some aspects, such a product can be first precipitated from the reaction. Precipitation can be carried out by adding an excess (e.g., at least 2-3 times the volume of the reaction volume) of alcohol (e.g., 100% or 95% concentration) (e.g., methanol, ethanol, isopropanol) or other solvents (e.g., acetonitrile, ethyl acetate) to the reaction. The precipitated product can then be separated using a filter funnel, centrifuge, filter press or any other method or equipment that removes liquid from the solid. The separated product can be dried, such as by vacuum drying, air drying or freeze drying.

[0126] In some respects, the glucan derivative product of esterification can be separated by comprising wherein filtering the reaction completed by ultrafiltration (for example, with 5 or 10 molecular weight cutoff filters), or the step of its diluted form.Optionally, the reaction completed by first regular filtering (that is, without ultrafiltration) or its diluted form, and then the filtrate can be subjected to ultrafiltration.Then the concentrated liquid obtained by ultrafiltration can be dried into its component solid, such as by freeze drying, or solid can be precipitated out from liquid and then dried (for example, freeze drying).

[0127] The esterified glucan derivative product herein may optionally be washed one or more times with a liquid that does not readily dissolve the product after precipitation or drying. For example, the glucan ester product may be washed with alcohol, acetone, aromatic compounds, or any combination of these, depending on the solubility of the ester product therein (where lack of solubility is desirable for washing). Typically, solvents containing organic solvents (e.g., 95%-100%) such as alcohols are preferred for washing the glucan ester derivative product.

[0128] Any of the above esterification reactions can be repeated using the glucan ester derivative products herein as starting materials for further modification. Such further modification can be with the same esterification agent used in the first reaction, or with a different esterification agent.

[0129] The composition as disclosed herein comprising at least one glucan ester derivative herein can be, for example, an aqueous composition (eg, a solution or dispersion such as a colloidal dispersion) or a dry composition. In some aspects, the compositions herein can comprise about, at least about, or less than about 0.01, 0.05, 0.1, 0.2, 0.25, 0.3, 0.4, 0.5, 0.6, 0.7, 0.75, 0.8, 0.9, 1.0, 1.2, 1.25, 1.4, 1.5, 1.6, 1.75, 1.8, 2.0, 2.25, 2.5, 3.0, 3.5, 4.0, 4.5, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 99.5 wt % or w / v % of a glucan ester derivative. The composition can include, for example, a range between any two of these wt% or w / v% values ​​(e.g., 5-50, 5-45, 5-40, 5-35, 5-30, 5-25, 5-20, 5-15, 5-10, 1-20, 1-15, 1-10, 1-7.5, 1-5, 2-20, 2-15, 2-10, 2-7.5, 2-5, 3-20, 3-15, 3-10, 3-7.5, or 3-5 wt% or w / v%). The liquid component of the aqueous composition can be an aqueous fluid such as water or an aqueous solution. The solvent of the aqueous solution is typically water, or can include, for example, about, or at least about 10, 20, 30, 40, 50, 60, 70, 80, 90, 95, 98, or 99 wt% of water, or as disclosed below. In some aspects, the compositions herein can comprise or be in the form of a solution, a dispersion (eg, an emulsion), a mixture, a wet cake or powder, a dry powder, an extrudate, a composite, a film / coating, a fiber, or a fibrid.

[0130] In some aspects, the solvent of the compositions herein comprises water and, for example, at least about 40% (v / v or w / w) of one or more polar organic solvents. In some aspects, the solvent comprises about, or at least about 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100 7, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 40-90, 40-80, 40-70, 40-60, 50-90, 50-80, 50-70, 50-60, 60-90, 60-80, 60-70, 70-90, 70-80, 40-70, 40-60, 75-85, or 85-95 v / v % or w / w % of one or more polar organic solvents. The balance of the solvent is typically only water (e.g., a solvent with about 75 v / v % polar organic solvent has about 25 v / v % water), but may optionally include (e.g., less than 2, 1, 0.5, or 0.25 v / v %) of one or more other liquids except the polar organic solvent. Considering that it has water, the solvent herein can be optionally characterized as an aqueous solvent. Although the solvent herein typically contains one type of polar organic solvent, it can optionally include two, three or more polar organic solvents; in such aspects, the polar organic solvent concentration is typically the concentration of the combination of polar organic solvents.

[0131] In some aspects, the polar organic solvent can be protic. Examples of protic polar organic solvents herein include alcohols (e.g., methanol, ethanol, isopropanol, 1-propanol, the tert-butyl alcohol, n-butyl alcohol, isobutyl alcohol), methylformamide and formamide. Other examples of protic polar organic solvents herein include n-butyl alcohol, ethylene glycol, 2-methoxyethanol, 1-methoxy-2-propanol, glycerol, 1,2-propylene glycol and 1,3-propanetriol.

[0132] In some respects, polar organic solvent can be aprotic. The example of aprotic polar organic solvent includes acetonitrile, dimethyl sulfoxide, acetone, DMF, N,N-dimethylacetamide, tetrahydrofuran, propylene carbonate and sulfolane herein. Other examples of aprotic polar organic solvent include hexamethylphosphoramide, dimethyl imidazolidinone (1,3-dimethyl-2-imidazoles), dioxane, nitromethane and butanone herein. Usually, ester, ketone and aldehyde solvent without acidic hydrogen atom are other examples of aprotic polar organic solvent herein.

[0133] The aqueous compositions herein can have, for example, about, at least about, or less than about 1, 5, 10, 100, 200, 300, 400, 500, 600, 700, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 15000, 1-300, 10-300, 2 The viscosity of the aqueous composition of the present invention can be 5-300, 50-300, 1-250, 10-250, 25-250, 50-250, 1-200, 10-200, 25-200, 50-200, 1-150, 10-150, 25-150, 50-150, 1-100, 10-100, 25-100, or 50-100 centipoise (cps). For example, the viscosity can be measured as with the aqueous composition herein at any temperature between about 3°C ​​to about 80°C (e.g., 4°C-30°C, 15°C-30°C, 15°C-25°C). The viscosity is typically measured as at atmospheric pressure (about 760 Torr) or at a pressure of ±10% thereof. Viscosity can be measured using, for example, a viscometer or a rheometer, and can optionally be, for example, measured at about 0.1, 0.5, 1.0, 5, 10, 50, 100, 500, 1000, 0.1-500, 0.1-100, 1.0-500, 1.0-1000, or 1.0-100 s -1 The shear rate is measured at a shear rate (rotational shear rate) of 0.1 % (1 / s) or about 5, 10, 20, 25, 50, 100, 200, or 250 rpm (revolutions per minute).

[0134] For example, a composition as disclosed herein can have an average molecular weight of about, or less than about, 1500, 1400, 1300, 1200, 1100, 1000, 900, 800, 700, 600, 500, 400, 300, 280, 260, 240, 220, 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 90, 80, 70, 60, 50, 45, 40, 35, 30, 25, 20, 180, 160, , 14, 12, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 1-250, 1-200, 1-150, 1-100, 1-50, 1-20, 1-15, 1-10, 1-5, 2-250, 2-200, 2-150, 2-100, 2-50, 2-20, 2-15, 2-10, 2-5, 10-250, 10-200, 10-150, 10-100, 10-50, or 10-20 NTU (nephelometric turbidity units). Any of these NTU values ​​can optionally be relative to the alpha-glucan ester derivative and solvent component portions of the compositions herein. In some aspects, it is contemplated that any of these NTU levels will persist for about, at least about, or up to about 0.5, 1, 2, 4, 6, 8, 10, 20, 30, 60, 90, 120, 150, 180, 210, 240, 270, 300, 330, or 360 days, or 1, 2, or 3 years (typically from initial preparation). Any suitable method can be used to measure turbidity, such as in Progress in Filtration and Separation (Edition: 1, Chapter 16. Turbidity: a measure of filtrate and supernatant quality?, Publisher: Academic Press, Editor: EStarleton, July 2015) (which is incorporated herein by reference), or as described in the Examples below.

[0135] In some aspects, the aqueous solution component of the aqueous composition has no (detectable) dissolved sugar, or has about 0.1-1.5, 0.1-1.25, 0.1-1.0, 0.1-.75, 0.1-0.5, 0.2-0.6, 0.3-0.5, 0.2, 0.3, 0.4, 0.5, or 0.6 wt % dissolved sugar. Such dissolved sugars may include, for example, sucrose, fructose, leucrose, and / or soluble glucose-oligosaccharides. In some aspects, the aqueous solution component of the aqueous composition may have, for example, one or more salts / buffers (e.g., Na +, Cl-, NaCl, phosphate, tris, citrate) (e.g., ≤0.1, 0.5, 1.0, 2.0, or 3.0 wt %), and / or a pH of about 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, 9.5, 10.0, 10.5, 4.0-10.0, 4.0-9.0, 4.0-8.0, 5.0-10.0, 5.0-9.0, 5.0-8.0, 6.0-10.0, 6.0-9.0, or 6.0-8.0. In some aspects, such as esters of insoluble glucans herein (e.g., α-1,3-glucans having a DP>8 or>9), the glucan esters are insoluble under aqueous conditions having a pH of at least about 10, 10.5, or 11 (e.g., at a concentration of at least about 0.5 wt % or 1.0 wt %).

[0136] In some aspects, for aqueous compositions that are aqueous dispersions of particles of the glucan esters of the present disclosure (e.g., emulsions), the particles are dispersed in about or at least about 30%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%, 98%, 99%, or 100% of the volume of the dispersion. In some aspects, it is expected that such a dispersion level (e.g., emulsion) will last for about, at least about, or up to about 0.5, 1, 2, 4, 6, 8, 10, 20, 30, 60, 90, 120, 150, 180, 210, 240, 270, 300, 330, or 360 days, or 1, 2, or 3 years (typically from the initial preparation of the dispersion).

[0137] The temperature of the compositions herein can be, for example, about, at least about, or up to about 0°C, 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, 45°C, 50°C, 55°C, 60°C, 65°C, 70°C, 75°C, 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 5°C-50°C, 20°C-25°C, 20°C-30°C ℃, 20℃-40℃, 30℃-40℃, 40℃-130℃, 40℃-125℃, 40℃-120℃, 70℃-130℃, 70℃-125℃, 70℃-120℃, 80℃-130℃, 80℃-125℃, 80℃-120℃, 60℃-100℃, 60℃-90℃, 70℃-100℃, 70℃-90℃, 75℃-100℃, 75℃-90℃, or 75℃-85℃.

[0138] In some respects, the composition herein can be non-aqueous (for example, dry composition). The example of such embodiment includes powder, granule, microcapsule, thin slice or any other form of particulate matter. Other examples include larger composition such as spherical particle, rod, core, bead, tablet, stick or other agglomerates, or ointment or lotion (or any other form of non-aqueous or dry composition herein). Non-aqueous composition or dry composition typically have about or no more than about 12,10,8,6,5,4,3,2,1.5,1.0,0.5,0.25,0.10,0.05 or 0.01wt% water included therein. In some respects (for example, those relating to clothing or dishwashing detergent), the dry composition herein can be provided with a sac or pouch.

[0139] In some aspects, the compositions herein comprising the glucan ester derivatives can be detergent compositions. Examples of such compositions as detergents for dishwashing and detergents for fabric care are disclosed herein.

[0140] In some aspects, the compositions herein can include one or more salts, such as sodium salts (e.g., NaCl, Na2SO4). Other non-limiting examples of salts include those having (i) aluminum, ammonium, barium, calcium, chromium (II or III), copper (I or II), iron (II or III), hydrogen, lead (II), lithium, magnesium, manganese (II or III), mercury (I or II), potassium, silver, sodium, strontium, tin (II or IV), or zinc cations, and (ii) acetates, borates, bromates, bromides, carbonates, chlorates, chlorides, chlorites, chromates, cyanamides, cyanides, dichromate, dihydrogenphosphate, ferrocyanide, ferrocyanide, fluoride, bicarbonate, hydrogenphosphate, hydrogensulfate, hydrogensulfide, hydrogensulfite, hydride, hydroxide, hypochlorite, iodide, iodide, nitrate, nitride, nitrite, oxalate, oxide, perchlorate, permanganate, peroxide, phosphate, phosphide, phosphite, silicate, stannate, stannate, sulfate, sulfide, sulfite, tartrate, or thiocyanate anion. Thus, for example, any salt having a cation from (i) above and an anion from (ii) above can be in the composition. The salt can be present in the aqueous compositions herein at a wt % basis, for example, about or at least about .01, .025, .05, .075, .1, .25, .5, .75, 1.0, 1.25, 1.5, 1.75, 2.0, 2.5, 3.0, 3.5, .01-3.5, .5-3.5, .5-2.5, or .5-1.5 wt % (such wt % values ​​typically refer to the total concentration of the salt or salts).

[0141] The compositions herein may optionally contain one or more enzymes (active enzymes). Examples of suitable enzymes include proteases, cellulases, hemicellulases, peroxidases, lipolytic enzymes (e.g., metallolipolytic enzymes), xylanases, lipases, phospholipases, esterases (e.g., arylesterases, polyesterases), perhydrolases, cutinases, pectinases, pectinase, mannanases, keratinases, reductases, oxidases (e.g., choline oxidases), phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidases, hyaluronidases, chondroitinases, laccases, metalloproteinases, amadoriases, glucoamylases, arabinofuranosidases, phytases, isomerases, transferases, nucleases, and amylases. If one or more enzymes are included, they can be included in the compositions herein at, for example, about 0.0001-0.1 wt% (e.g., 0.01-0.03 wt%) of active enzyme (e.g., calculated as pure enzyme protein). In fabric care or automatic dishwashing applications, the enzymes herein (e.g., any of the above, such as cellulases, proteases, amylases, and / or lipases) can be present, for example, in a concentration of a minimum of about 0.01-0.1 ppm total enzyme protein, or about 0.1-10 ppb total enzyme protein (e.g., less than 1 ppm) to a maximum of about 100, 200, 500, 1000, 2000, 3000, 4000, or 5000 ppm total enzyme protein in the aqueous composition (e.g., wash liquor, grey water) in which the fabric or dishware is treated.

[0142] In some aspects, the glucan ester derivatives and / or compositions comprising such derivatives are biodegradable. After 15, 30, 45, 60, 75, or 90 days of testing, for example, such biodegradability can be determined as about, at least about, or at most about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 5%-60%, 5%-8 ... -90%, 40%-70%, 50%-70%, 60%-70%, 40%-75%, 50%-75%, 60%-75%, 70%-75%, 40%-80%, 50%-80%, 60%-80%, 70%-80%, 40%-85%, 50%-85%, 60%-85%, 70%-85%, 40%-90%, 50%-90%, 60%-90%, or 70%-90%, or any value between 5% and 90%. It is expected that such biodegradability can be about, at least about, or at most about 10%, 25%, 50%, 75%, 100%, 150%, 200%, 250%, 500%, 750%, or 1000% higher than the biodegradability of currently used materials.

[0143] The composition can include one, two, three, four or more different glucan ester derivatives herein and optionally at least one underivatized glucan (e.g., as disclosed herein). For example, the composition can include at least one type of glucan ester derivative and at least one type of glucan; in some aspects, the latter can be (or can be) a precursor compound of the former. In some aspects, no underivatized α-glucan (e.g., a precursor compound) is present.

[0144] The compositions comprising at least one glucan ester derivative as disclosed herein can be in the form of, for example, a household care product, a personal care product, an industrial product, an ingestible product (e.g., a food product), a medical product, or a pharmaceutical product, such as described in any of U.S. Patent Application Publication Nos. 2018 / 0022834, 2018 / 0237816, 2018 / 0230241, 20180079832, 2016 / 0311935, 2016 / 0304629, 2015 / 0232785, 2015 / 0368594, 2015 / 0368595, 2016 / 0122445, 2019 / 0202942, or 2019 / 0309096, or International Patent Application Publication No. WO2016 / 133734, all of which are incorporated herein by reference. In some aspects, the composition may comprise at least one component / ingredient of a household care product, a personal care product, an industrial product, a pharmaceutical product, or an ingestible product (e.g., a food product) as disclosed in any of the aforementioned disclosures and / or as disclosed herein.

[0145] It is believed that in some aspects, the compositions can be used to provide one or more of the following physical properties to a personal care product, a pharmaceutical product, a household product, an industrial product, or an ingestible product (e.g., a food product): for example, thickening, freeze / thaw stability, lubricity, water retention and release, texture, consistency, shape retention, emulsification, binding, suspension, dispersion, gelling, or reduced mineral hardness.

[0146] The personal care products herein are not particularly limited, and include, for example, skin care compositions, cosmetic compositions, antifungal compositions, and antibacterial compositions. The personal care products herein may be in the form of, for example, lotions, creams, pastes, balms, ointments, pomades, gels, liquids, combinations of these, and the like. If desired, the personal care products disclosed herein may contain at least one active ingredient. Active ingredients are generally considered to be ingredients that cause the desired pharmacological effect.

[0147] In some respects, skin care products can be applied to skin to solve the skin damage relevant with lack of moisture.Skin care products can also be used to solve the visual appearance of skin (for example, reduce the outward appearance of flake, cracking and / or red skin) and / or the touch of skin (for example, reduce the roughness and / or dryness of skin, improve the softness and microscopic refinement of skin simultaneously).Typically, skin care products can include at least one active ingredient for treating or preventing skin diseases, providing cosmetic effect or providing moisturizing benefit for skin, such as zinc oxide, vaseline, white vaseline, mineral oil, cod liver oil, lanolin, polydimethylsiloxane, stearin, vitamin A, allantoin, calamine, kaolin, glycerine or colloidal oatmeal and these combinations.Skin care products can include for example one or more natural moisturizing factors, such as ceramide, hyaluronic acid, glycerine, squalane, amino acid, cholesterol, fatty acid, triglyceride, phospholipid, sphingolipid, urea, linoleic acid, glycosaminoglycan, mucopolysaccharide, sodium lactate or sodium pyrrolidonecarboxylate. Other ingredients that can be included in the skin care product include, but are not limited to, glycerides, almond oil, canola oil, squalane, squalene, coconut oil, corn oil, jojoba oil, jojoba wax, lecithin, olive oil, safflower oil, sesame oil, shea butter, soybean oil, sweet almond oil, sunflower oil, tea tree oil, shea butter, palm oil, cholesterol, cholesterol esters, wax esters, fatty acids, and orange peel oil. In some aspects, the skin care product can be an ointment, a lotion, or a disinfectant (e.g., a hand disinfectant).

[0148] The personal care products herein can also be in the form of, for example, makeup, lipstick, mascara, rouge, foundation, blush, eyeliner, lip liner, lip gloss, other makeup, sunscreen, sunscreen lotion, nail polish, nail conditioner, temporary tattoo ink, bath gel, shower gel, body wash, facial cleanser, lip balm, skin cream, cold cream, body cream, body spray, soap, body scrub, exfoliant, astringent, scruffing lotion, depilatory, permanent waving solution, anti-dandruff preparation, antiperspirant composition, deodorant, shaving product, pre-shave product, after-shave product, cleanser, skin gel, rinse, dentifrice composition, toothpaste, or mouthwash. Examples of personal care products (e.g., cleansers, soaps, scrubs, cosmetics) include a carrier or exfoliant (e.g., jojoba beads [jojoba ester beads]) (e.g., about 1-10, 3-7, 4-6, or 5 wt %); such agents may optionally be dispersed within the product.

[0149] In some aspects, the personal care product can be a hair care product. Examples of hair care products herein include shampoo, hair conditioner (leave-in or rinse-off), nourishing hair water, hair dye, hair dye product, hair shine product, hair essence, hair anti-frizz product, split-end repair product, mousse (e.g., hair styling mousse), hair spray (e.g., hair styling spray) and styling gel (e.g., hair styling gel). In some embodiments, the hair care product can be in the form of a liquid, paste, gel, solid, or powder. Hair care products as disclosed in the present invention typically contain one or more of the following ingredients commonly used in formulating hair care products: anionic surfactants, such as sodium polyoxyethylene lauryl ether sulfate; cationic surfactants, such as stearyl trimethyl ammonium chloride and / or distearyl trimethyl ammonium chloride; nonionic surfactants, such as glyceryl monostearate, sorbitan monopalmitate and / or polyoxyethylene cetyl ether; wetting agents, such as propylene glycol, 1,3-butylene glycol, glycerol, sorbitol, pyroglutamate, amino acids and / or trimethylglycine; hydrocarbons, such as liquid paraffin, petrolatum, paraffin wax, squalane and / or olefin oligomers; higher alcohols, such as stearyl alcohol and / or cetyl alcohol; superfatting agents; antidandruff agents; disinfectants; anti-inflammatory agents; crude drugs; water-soluble polymers, such as methylcellulose, hydroxycellulose and / or partially deacetylated chitin; preservatives, such as parabens; ultraviolet light absorbers; pearlescent agents; pH adjusters; fragrances; and pigments.

[0150] In some aspects, the composition can be a hair care composition, such as a hair styling or hair setting composition (e.g., a hair spray, a hair gel or lotion, a hair mousse / foam) (e.g., an aerosol hair spray, a non-aerosol pump hair spray, a spritze, a foam, a crème, a paste, a non-runny gel, a mousse, a pomade, a hair spray, a wax). Hair styling / styling compositions / formulations that may be adapted to include at least one glucan ester derivative herein may be, for example, US 20090074697, WO 1999048462, US20130068849, JP H0454116A, US 5304368, AU 667246B2, US 5413775, US 5441728, US5939058, JP 2001302458A, US 6346234, US20020085988, US 7169380, US 20090060858, US20090326151, US20160008257, WO 2020164769, or US20110217256, all of which are incorporated herein by reference.Hair care compositions such as hair styling / styling compositions may contain one or more ingredients / additives as disclosed in any of the foregoing references, and / or one or more of the following: fragrances / fragrances, aromatherapy essences, herbs, infusions, antimicrobial agents, stimulants (e.g., caffeine), essential oils, hair dyes, colorants or coloring agents, anti-greying agents, defoamers, sunscreens / UV blockers (e.g., benzophenone-4), vitamins, antioxidants, surfactants or other wetting agents, mica, silica, metallic flakes or other glitter effect materials, conditioning agents (e.g., volatile or non-volatile silicone fluids), antistatic agents, sunscreens, detackifying agents, penetrants, preservatives (e.g., phenoxyethanol, ethylhexylglycerin, parabens, diazolidinyl urea, urea), iodopropynyl butylcarbamate), emollients (e.g., panthenol, isopropyl myristate), rheology modifying or thickening polymers (e.g., acrylates / methacrylamide copolymer, polyacrylic acid [e.g., CARBOMER]), emulsified oil phase, petrolatum, fatty alcohols, diols and polyols, emulsifiers (e.g., PEG-40 hydrogenated castor oil, oleth-20), humectants (e.g., glycerin, caprylyl glycol), silicone derivatives, proteins, amino acids (e.g., isoleucine), conditioning agents, chelating agents (e.g., EDTA), solvents (e.g., see below), monosaccharides (e.g., dextrose), disaccharides, oligosaccharides, pH stabilizing compounds (e.g., aminomethyl propanol), film formers (e.g., acrylates / hydroxy esters acrylate copolymers, polyvinyl pyrrolidone / vinyl acetate copolymers, triethyl acetate), aerosol propellants (e.g., C3-C5 alkanes, such as propane, isobutane, or n-butane, monoalkyl ethers, dialkyl ethers, such as di(C1-C4 alkyl) ethers [e.g., dimethyl ether]), and / or any other suitable material herein. The glucan ester derivatives as used in the hair styling / styling compositions herein can act, for example, as a hair fixative / styling agent (typically non-permanent hair fixative, but long-lasting), and are optionally the only hair fixative in the composition. Optional additional hair fixative / setting agents herein include PVP (polyvinyl pyrrolidone), octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer, vinylcaprolactam / PVP / dimethylaminoethyl methacrylate copolymer, AMPHOMER, or any film former as listed above.

[0151] The total amount of one or more glucan ester derivatives in a hair care composition such as the hair styling / styling composition herein can be, for example, about, at least about, or less than about 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 0.5-15 wt%, 0.5-10 wt%, 0.5-5 wt%, 0.5-2 wt%, 1-15 wt%, 1-10 wt%, 1-5 wt%, 1-2 wt%, 2.5-7.5 wt%, 3-7 wt%, or 4-6 wt%. For example, the hair styling / styling composition may include a solvent comprising water and optionally a water-miscible (typically polar) organic compound (e.g., liquid or gas), such as an alcohol (e.g., ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol), an alkylene glycol alkyl ether, and / or a monoalkyl or dialkyl ether (e.g., dimethyl ether). If the organic compound is included, it may constitute, for example, about 10%, 20%, 30%, 40%, 50%, or 60% by weight or volume of the solvent (the balance being water). For example, the amount of solvent in the hair styling / styling composition herein may be about 50-90 wt%, 60-90 wt%, 70-90 wt%, 80-90 wt%, 50-95 wt%, 60-95 wt%, 70-95 wt%, 80-95 wt%, or 90-95 wt%.

[0152] Examples of hair styling gel formulations herein may include about 90-95 wt % (e.g., about 92 wt %) of a solvent (e.g., any of the ones described herein), 0.3-1.0 wt % (e.g., about 0.5 wt %) of a thickener (e.g., polyacrylic acid), 0.1-0.3 wt % (e.g., about 0.2 wt %) of a chelating agent (e.g., EDTA) (optional), 0.2-1.0 wt % (e.g., about 0.5 wt %) of a humectant (e.g., glycerol), 0.01-0.05 wt % (e.g., about 0.02 wt %) of a UV blocker (e.g., benzophenone-4) (any of the ones described herein), %, 0.05-0.3 wt % (e.g., about 0.1 wt %) preservative (e.g., diazolidinyl urea) (optional), 0.5-1.2 wt % (e.g., about 0.8 wt %) emulsifier (e.g., oleth-20), 0.1-0.3 wt % (e.g., about 0.2 wt %) fragrance / fragrance (optional), 0.2-1.0 wt % (e.g., about 0.5 wt %) pH stabilizing compound (e.g., aminomethyl propanol), and 3-7 wt % (e.g., about 5 wt %) of the glucan ester derivative herein (e.g., as a hair fixative / styling agent).

[0153] Examples of hair styling spray formulations herein may include about 0.2-1.0 wt % (e.g., about 0.5 wt %) pH stabilizing compound (e.g., aminomethyl propanol), 0.1-0.3 wt % (e.g., about 0.2 wt %) fragrance / fragrance (optional), 0.05-0.12 wt % (e.g., about 0.08 wt %) surfactant (e.g., ethoxylated dimethicone polyol), 0.05-0.12 wt % (e.g., about 0.08 wt %) conditioning agent (e.g., cyclomethicone) (optional), 0.05-0.12 wt % (e.g., about 0.08 wt %) 0.3 wt % (e.g., about 0.2 wt %) preservative (e.g., sodium benzoate) (optional), 15-20 wt % (e.g., about 17 wt %) water, 30-40 wt % (e.g., about 65 wt %) alcohol (e.g., ethanol), 40-60 wt % (e.g., about 45 wt %) propellant (e.g., dimethyl ether, or about a 2:1 mixture of dimethyl ether and a C3-C5 alkane [e.g., a mixture of propane and isobutane]), and 2-4 wt % (e.g., about 2.75 wt %) of the glucan ester derivative herein (e.g., as a hair fixing / styling agent).

[0154] Some aspects of the present disclosure relate to hair that has been treated with a hair care composition (e.g., a hair styling / styling composition, shampoo, or conditioner) herein. For example, the hair can include a glucan ester derivative on its surface, such as in a film / coating on the hair, and / or adsorbed or otherwise deposited on the surface of the hair; optionally, one or more other ingredients of the hair care composition herein can also be present. Typically, hair as disclosed herein, such as hair having a coating comprising an α-glucan ester, does not exhibit flaking visible to the naked eye (i.e., little or no noticeable flaking).

[0155] Various examples of personal care formulations comprising at least one glucan ester derivative as disclosed herein are disclosed in (1-3) below.

[0156] (1) A hair conditioning composition comprising: cetyl alcohol (1-3%), isopropyl myristate (1-3%), hydroxyethyl cellulose ( 250HHR, 0.1-1%), dextran ester derivatives (0.1-2%), potassium salt (0.1-0.5%), II preservative (0.5%, obtained from International Specialty Products), and the balance was water.

[0157] (2) A hair shampoo composition comprising: 5-20% sodium lauryl ether sulfate (SLES), 1-2wt% cocamidopropyl betaine, 1-2wt% sodium chloride, 0.1-2% dextran ester derivative, a preservative (0.1-0.5%), and the balance being water.

[0158] (3) A skin lotion composition comprising: 1-5% glycerin, 1-5% ethylene glycol stearate, 1-5% stearic acid, 1-5% mineral oil, 0.5-1% acetylated lanolin ( 98), 0.1-0.5 cetyl alcohol, 0.2-1% triethanolamine, 0.1-1wt% II preservative, 0.5-2 wt% of a dextran ester derivative, and the balance is water.

[0159] The pharmaceutical product herein can be in the form of, for example, an emulsion, a liquid, an elixir, a gel, a suspension, a solution, a cream, or an ointment. In addition, the pharmaceutical product herein can be in the form of any one of the personal care products disclosed herein, such as antibacterial or antifungal compositions. The pharmaceutical product can further comprise one or more pharmaceutically acceptable carriers, diluents, and / or pharmaceutically acceptable salts. The composition herein can also be used in, for example, capsules, tablets, tablet coatings, and as an excipient for medicaments and drugs.

[0160] The household and / or industrial products herein may be in the form of, for example, drywall tape joint compounds; mortars; grouts; cement plasters; spray plasters; cement plasters; adhesives; pastes; wall / ceiling conditioners; adhesives and processing aids for tape casting, extrusion molding, injection molding, and ceramics; spray adhesives and suspension / dispersion aids for pesticides, herbicides, and fertilizers; fabric care products, such as fabric softeners and laundry detergents; hard surface cleaners; air fresheners; polymer emulsions; latex; gels, such as water-based gels; surfactant solutions; coatings, such as water-based coatings; protective coatings; adhesives; sealants and caulks; inks, such as water-based inks; metalworking fluids; films or coatings; or emulsion-based metal cleaning fluids for electroplating, phosphating, galvanizing, and / or general metal cleaning operations. In some aspects, the compositions herein are included in fluids as viscosity modifiers and / or drag reducers; such uses include, for example, downhole operations / fluids (e.g., hydraulic fracturing and enhanced oil recovery).

[0161] Some aspects herein relate to (i) a salt water such as sea water, or (ii) an aqueous solution having one or a combination of about 2.0, 2.25, 2.5, 2.75, 3.0, 3.25, 3.5, 3.75, 4.0, 2.5-4.0, 2.75-4.0, 3.0-4.0, 2.5-3.5, 2.75-3.5, 3.0-3.5, 3.0-4.0, or 3.0-3.5 wt % of a salt (e.g., including at least NaCl), having at least one water-soluble glucan ester derivative as disclosed herein. The concentration of glucan ester derivative in this water of (i) or (ii) can be for example about, at least about or less than about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 0.1-0.6, 0.1-0.5, 0.1-0.4, 0.1-0.3 or 0.1-0.2wt%. Although the relatively high salt concentration in this type of aqueous composition, it is envisioned that glucan ester derivative can be retained in solution completely or mostly and viscosity is provided in some aspects. Such as (i) or (ii) such solution of the viscosity adjustment of glucan ester derivative herein can be in the system (for example, any system herein, such as downhole operation) using this solution when it is used.

[0162] Examples of ingestible products herein include food, beverages, animal feed, animal health and / or nutritional products, and / or pharmaceutical products. The intended use of the composition as disclosed herein in an ingestible product may be, for example, to provide texture, increase volume, and / or thicken.

[0163] Other examples of using the compositions of the present disclosure for ingestible products include use as: bulking, binding and / or coating ingredients; carriers for coloring agents, flavorings / fragrances, and / or high-intensity sweeteners; spray drying aids; bulking, thickening, dispersing, and / or emulsifying agents; and ingredients for promoting moisture retention (humectants). Illustrative examples of products with the compositions herein that can be prepared include food products, beverage products, pharmaceutical products, nutritional products, and sports products. Examples of beverage products herein include concentrated beverage mixes, carbonated beverages, non-carbonated beverages, fruit-flavored beverages, juices, teas, coffees, milk nectars, powdered beverages, liquid concentrates, milk beverages, ready-to-drink (RTD) products, smoothies, alcoholic beverages, flavored waters, and combinations thereof. Examples of food products herein include baked goods (e.g., bread), candies, frozen dairy products, meats, artificial / synthetic / cultured meats, cereal products (e.g., breakfast cereals), dairy products (e.g., yogurt), condiments (e.g., mustard, ketchup, mayonnaise), snack bars, soups, dressings, mixes, prepared foods, baby foods, dietary preparations, peanut butter, syrups, sweeteners, food coatings, pet foods, animal feeds, animal health and nutritional products, dried fruits, sauces, gravies, jams / jellies, dessert products, spreads, batters, breadings, seasoning mixes, frostings, etc. In some aspects, the compositions herein can provide or enhance the foaming of beverages such as dairy beverages, non-dairy alternative beverages (e.g., "vegan" milks such as soy milk, almond milk, or coconut milk), dairy creamers, and / or non-dairy creamers (e.g., for hot beverages such as coffee [e.g., cappuccino], tea [e.g., chai tea]).

[0164] The compositions comprising the glucan ester derivatives herein can be, for example, included in personal care products, pharmaceutical products, household products, industrial products, or ingestible products (e.g., food products) in an amount that provides desired thickening and / or dispersibility. The concentration or amount of the compositions disclosed in the product are any one of the weight percentages provided herein.

[0165] In some aspects, the composition comprising at least one glucan ester derivative herein may be in the form of a fabric care composition or include a fabric care composition. For example, the fabric care composition may be used for hand washing, machine washing and / or other purposes, such as soaking and / or pretreatment of fabrics. The fabric care composition may take the following forms: for example, laundry detergent; fabric conditioner; any product added during washing, rinsing or drying; unit dose or spray. The fabric care composition in liquid form may be in the form of an aqueous composition. In other embodiments, the fabric care composition may be in a dry form, such as a granular detergent or a fabric softener sheet added to a dryer. Other non-limiting examples of fabric care compositions may include: general or heavy-duty detergents in granular or powder form; general or heavy-duty detergents in liquid, gel or paste form; liquid or dry delicate fabric (e.g., delicate clothing) detergents; cleaning aids such as bleach additives, "stain bars" or pretreatments; substrate-containing products, such as dry and wet wipes, pads or sponges; sprays and fine mists; water-soluble unit dose products. As further examples, the compositions herein may be in the form of a liquid, gel, powder, hydrocolloid, aqueous solution, granules, tablets, capsules, beads or lozenges, single compartment sachets, multi-compartment sachets, single compartment pouches, or multi-compartment pouches.

[0166] The detergent composition herein can be in any useful form, such as powder, granules, paste, stick, unit dose or liquid. Liquid detergents can be aqueous, typically containing up to about 70 wt % water and 0 wt % to about 30 wt % organic solvents. Liquid detergents can also be in the form of a compact gel type containing only about 30 wt % water.

[0167] Detergent compositions (e.g., compositions of fabric care products or any other products herein) typically contain one or more surfactants, wherein the surfactant is selected from nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, zwitterionic surfactants, semi-polar nonionic surfactants and mixtures thereof. In some embodiments, the surfactant is present at a level of from about 0.1% to about 60%, while in alternative embodiments, the level is from about 1% to about 50%, and in further embodiments, the level is from about 5% to about 40%, by weight of the detergent composition. Typically, detergents will contain 0 wt % to about 50 wt % of anionic surfactants, such as linear alkylbenzene sulfonates (LAS), alpha-olefin sulfonates (AOS), alkyl sulfates (fatty alcohol sulfates) (AS), alcohol ethoxy sulfates (AEOS or AES), secondary alkane sulfonates (SAS), alpha-sulfo fatty acid methyl esters, alkyl- or alkenyl succinic acid or soap. In addition, the detergent composition may optionally contain 0 wt % to about 40 wt % of a nonionic surfactant, such as alcohol ethoxylates (AEO or AE), carboxylated alcohol ethoxylates, nonylphenol ethoxylates, alkyl polyglycosides, alkyl dimethylamine oxides, ethoxylated fatty acid monoethanolamides, fatty acid monoethanolamides, or polyhydroxy alkyl fatty acid amides (as described, for example, in WO 92 / 06154, which is incorporated herein by reference).

[0168] The detergent compositions herein may optionally include one or more detergent builders or builder systems. In some aspects, oxidized α-1,3-glucan may be included as a co-builder; oxidized α-1,3-glucan compounds for use herein are disclosed in U.S. Patent Application Publication No. 2015 / 0259439. In some aspects incorporating at least one builder, the cleaning composition comprises at least about 1%, from about 3% to about 60%, or even from about 5% to about 40% of the builder by weight of the composition. Examples of builders include the alkali metal, ammonium and alkanolammonium salts of polyphosphates; alkali metal silicates, alkaline earth metal and alkali metal carbonates; aluminosilicates; polycarboxylates; ether hydroxypolycarboxylates; copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulfonic acid, and carboxymethyloxysuccinic acid; the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids, such as ethylenediaminetetraacetic acid and nitrilotriacetic acid; as well as polycarboxylates such as mellitic acid, succinic acid, citric acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid and soluble salts thereof. Additional examples of detergent builders or complexing agents include zeolites, diphosphates, triphosphates, phosphonates, citrates, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTMPA), alkyl or alkenyl succinic acids, soluble silicates or layered cinnamate (e.g., SKS-6 from Hoechst).

[0169] In some embodiments, the builders form water-soluble hardness ion complexes (e.g., chelating builders), such as citrates and polyphosphates (e.g., sodium tripolyphosphate and sodium tripolyphosphate hexahydrate, potassium tripolyphosphate, and mixed sodium tripolyphosphate and potassium tripolyphosphate, etc.). It is contemplated that any suitable builder will find use in the present disclosure, including those known in the art (see, e.g., EP 2100949).

[0170] In some embodiments, suitable builders may include phosphate builders and non-phosphate builders. In some embodiments, the builder is a phosphate builder. In some embodiments, the builder is a non-phosphate builder. The builder can be used at a level of 0.1% to 80%, or from 5% to 60%, or from 10% to 50% by weight of the composition. In some embodiments, the product includes a mixture of phosphate and non-phosphate builders. Suitable phosphate builders include monophosphates, diphosphates, tripolyphosphates or oligomeric polyphosphates, including alkali metal salts of these compounds, including sodium salts. In some embodiments, the builder may be sodium tripolyphosphate (STPP). In addition, the composition may include carbonates and / or citrates, preferably citrates, that help achieve a neutral pH composition. Other suitable non-phosphate builders include homopolymers and copolymers of polycarboxylic acids and partially or completely neutralized salts thereof, monomeric polycarboxylic acids and hydroxycarboxylic acids and their salts. In some embodiments, the salts of the above-mentioned compounds include ammonium salts and / or alkali metal salts, i.e. lithium salts, sodium salts and potassium salts, including sodium salts. Suitable polycarboxylic acids include acyclic, alicyclic, heterocyclic and aromatic carboxylic acids, wherein in some embodiments they may contain at least two carboxyl groups, the carboxyl groups being separated from each other in each case by no more than two carbon atoms in some cases.

[0171] The detergent compositions herein may contain at least one chelating agent. Suitable chelating agents include, but are not limited to, copper, iron and / or manganese chelating agents and mixtures thereof. In embodiments where at least one chelating agent is used, the composition comprises from about 0.1% to about 15% or even from about 3.0% to about 10% of a chelating agent by weight of the composition.

[0172] The detergent compositions herein may contain at least one deposition aid. Suitable deposition aids include, but are not limited to, polyethylene glycol, polypropylene glycol, polycarboxylates, soil release polymers (such as polyethylene terephthalic acid), clays such as kaolin, montmorillonite, attapulgite, illite, bentonite, halloysite, and mixtures thereof.

[0173] The detergent compositions herein may contain one or more dye transfer inhibiting agents. Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof. Additional dye transfer inhibiting agents include manganese phthalocyanine, peroxidase, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles and / or mixtures thereof; chelating agents, examples of which include ethylenediaminetetraacetic acid (EDTA); diethylenetriaminepentamethylenephosphonic acid (DTPMP); hydroxyethanediphosphonic acid (HEDP); ethylenediamine N,N′-disuccinic acid (EDDS); methylglycine diacetic acid (MGDA); diethylenetriaminepentaacetic acid (DTPA); propylenediaminetetraacetic acid (PDT A); 2-hydroxypyridine-N-oxide (HPNO); or methylglycine diacetic acid (MGDA); glutamic acid N,N-diacetic acid (N,N-dicarboxymethylglutamate tetrasodium salt (GLDA); nitrilotriacetic acid (NTA); 4,5-dihydroxyisobenzene disulfonic acid; citric acid and any salts thereof; N-hydroxyethylethylenediaminetriacetic acid (HEDTA), triethylenetetraaminehexaacetic acid (TTHA), N-hydroxyethyliminodiacetic acid (HEIDA), dihydroxyethylglycine (DHEG), ethylenediaminetetrapropionic acid (EDTP) and derivatives thereof, which may be used alone or in combination with any of the above. In embodiments using at least one dye transfer inhibitor, the compositions herein may comprise from about 0.0001% to about 10%, from about 0.01% to about 5%, or even from about 0.1% to about 3% of the at least one dye transfer inhibitor by weight of the composition.

[0174] The detergent compositions herein may include silicates. In some of these embodiments, sodium silicate (e.g., sodium disilicate, sodium metasilicate, and / or crystalline phyllosilicate) may be used. In some embodiments, silicates are present at a level of from about 1% to about 20% by weight of the composition. In some embodiments, silicates are present at a level of from about 5% to about 15% by weight of the composition.

[0175] The detergent compositions herein may contain a dispersant. Suitable water-soluble organic materials include, but are not limited to, the homo- or co-polymeric acids or their salts, in which the polyacid comprises at least two carboxyl radicals separated from each other by not more than two carbon atoms.

[0176] The detergent composition herein may additionally include, for example, one or more enzymes as disclosed above. In some aspects, the detergent composition may include one or more enzymes, each of which is at a level of from about 0.00001% to about 10% by weight of the composition, and a cleaning auxiliary material of the remainder by weight of the composition. In some other aspects, the detergent composition may also include each enzyme at a level of from about 0.0001% to about 10%, from about 0.001% to about 5%, from about 0.001% to about 2%, or from about 0.005% to about 0.5% by weight of the composition. The enzymes contained in the detergent composition herein may be stabilized using conventional stabilizers such as: polyols, such as propylene glycol or glycerol; sugars or sugar alcohols; lactic acid; boric acid or boric acid derivatives (e.g., aromatic borate).

[0177] In some aspects, in addition to the glucan ester derivatives disclosed herein, the detergent composition may also include one or more other types of polymers. Examples of other types of polymers that can be used herein include carboxymethylcellulose (CMC), dextran, poly(vinyl pyrrolidone) (PVP), polyethylene glycol (PEG), poly(vinyl alcohol) (PVA), polycarboxylates such as polyacrylates, maleic acid / acrylic acid copolymers, and lauryl methacrylate / acrylic acid copolymers.

[0178] The detergent composition herein may contain a bleaching system. For example, the bleaching system may comprise a H2O2 source such as perboric acid or percarbonic acid, which may be combined with a peracid-forming bleach activator such as tetraacetylethylenediamine (TAED) or nonanoyloxybenzenesulfonate (NOBS). Alternatively, the bleaching system may comprise a peroxyacid (e.g., an amide, imide or sulfone type peroxyacid). Still alternatively, the bleaching system may be an enzymatic bleaching system comprising a perhydrolase, such as, for example, the system described in WO 2005 / 056783.

[0179] The detergent compositions herein may also contain conventional detergent ingredients such as fabric conditioners, clays, foam boosters, foam suppressors, anti-corrosion agents, soil suspension agents, anti-soil redeposition agents, dyes, bactericides, discoloration inhibitors, optical brighteners or perfumes. The pH of the detergent compositions herein (measured in aqueous solution at use concentrations) is typically neutral or alkaline (e.g., a pH of about 7.0 to about 11.0).

[0180] Examples of suitable anti-redeposition agents and / or clay soil removal agents for use in the fabric care products herein include polyethoxylated zwitterionic surfactants, water-soluble copolymers of acrylic acid or methacrylic acid and acrylic acid or methacrylic acid-ethylene oxide condensates (e.g., U.S. Pat. No. 3,719,647), cellulose derivatives such as carboxymethylcellulose and hydroxypropylcellulose (e.g., U.S. Pat. Nos. 3,597,416 and 3,523,088), and mixtures comprising nonionic alkyl polyethoxylated surfactants, polyethoxylated alkyl quaternary cationic surfactants, and fatty amide surfactants (e.g., U.S. Pat. No. 4,228,044). Non-limiting examples of other suitable anti-redeposition agents and clay soil removal agents are disclosed in U.S. Pat. Nos. 4,597,898 and 4,891,160 and International Patent Application Publication No. WO 95 / 32272, all of which are incorporated herein by reference.

[0181] Specific forms of detergent compositions that may be suitable for the purposes herein are disclosed, for example, in US 20090209445 A1, US 20100081598 A1, US 7001878 B2, EP 1504994 B1, WO 2001085888 A2, WO2003089562 A1, WO 2009098659 A1, WO 2009098660 A1, WO 2009112992 A1, WO 2009124160 A1, WO 2009152031 A1, WO 2010059483 A1, WO 2010088112 A1, WO 2010090915 A1, WO2010135238 A1, WO 2011094687 A1 , WO 2011094690 A1 , WO 2011127102 A1 , WO2011163428 A1 , WO 2008000567 A1 , WO 2006045391 A1 , WO 2006007911 A1 , WO2012027404 A1 , EP 1740690 B1 , WO 2012059336 A1 , US 6730646 B1 , WO 2008087426 A1 , WO2010116139 A1 , and WO 2012104613 A1 , all of which are incorporated herein by reference.

[0182] The laundry detergent composition herein may optionally be a heavy duty (general purpose) laundry detergent composition. Exemplary heavy duty laundry detergent compositions comprise a cleaning surfactant (10%-40% wt / wt), including an anionic cleaning surfactant (selected from the group consisting of linear or branched or random chain, substituted or unsubstituted alkyl sulfates, alkyl sulfonates, alkyl alkoxylated sulfates, alkyl phosphates, alkyl phosphonates, alkyl carboxylates and / or mixtures thereof) and optionally a nonionic surfactant (selected from the group consisting of linear or branched or random chain, substituted or unsubstituted alkyl alkoxylated alcohols, such as C8-C18 alkyl ethoxylated alcohols and / or C6-C12 alkyl phenol alkoxylates), wherein the weight ratio of anionic cleaning surfactant (having a hydrophilic index (HIc) from 6.0 to 9) to nonionic cleaning surfactant is greater than 1:1. Suitable cleaning surfactants also include cationic cleaning surfactants (selected from the following group: alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl tertiary sulfonium compounds, and / or mixtures thereof); zwitterionic and / or amphoteric cleaning surfactants (selected from the following group: alkanolamine sulfonobetaine); amphoteric surfactants; semi-polar nonionic surfactants and mixtures thereof.

[0183] The detergents herein, such as heavy duty laundry detergent compositions, may optionally include a surfactant enhancing polymer consisting of an amphiphilic alkoxylated grease cleaning polymer selected from the group consisting of alkoxylated polymers having branched hydrophilic and hydrophobic properties, such as alkoxylated polyalkyleneimines (in the range of 0.05 wt% - 10 wt%) and / or a random grafted polymer (typically comprising a hydrophilic backbone containing monomers selected from the group consisting of unsaturated C1-C6 carboxylic acids, ethers, alcohols, aldehydes, ketones, esters, sugar units, alkoxy units, maleic anhydride, saturated polyols (such as glycerol) and mixtures thereof; and one or more hydrophobic side chains selected from the group consisting of C4-C25 alkyl, polypropylene, polybutene, vinyl esters of saturated C1-C6 monocarboxylic acids, C1-C6 alkyl esters of acrylic or methacrylic acid, and mixtures thereof).

[0184] The detergents herein, such as heavy-duty laundry detergent compositions, may optionally include additional polymers, such as soil release polymers (including anion-terminated polyesters (e.g., SRP1); polymers in random or block configurations comprising at least one monomer unit selected from sugars, dicarboxylic acids, polyols, and combinations thereof; ethylene terephthalate-based polymers and copolymers thereof in random or block configurations, such as REPEL-O-TEX SF, SF-2, and SRP6, TEXCARE SRA100, SRA300, SRN100, SRN170, SRN240, SRN300, and SRN325, MARLOQUEST SL); one or more anti-redeposition agents herein (0.1 wt % to 10 wt %), including carboxylate polymers, such as polymers comprising at least one monomer selected from acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid, and any mixture thereof; vinyl pyrrolidone homopolymer; and / or polyethylene glycol, with a molecular weight ranging from 500 to 100,000 Da); and polymeric carboxylates (such as maleate / acrylate random copolymers or polyacrylate homopolymers).

[0185] The detergents herein, such as heavy-duty laundry detergent compositions, may optionally further comprise saturated or unsaturated fatty acids, preferably saturated or unsaturated C12-C24 fatty acids (0 wt% to 10 wt%); deposition aids (examples of which include polysaccharides; cellulosic polymers; poly(adipyl dimethyl ammonium halides) (DADMAC); and copolymers of DAD MAC with vinyl pyrrolidone, acrylamide, imidazole, imidazoline halides, and mixtures thereof (in random or block configuration); cationic guar gum; cationic starch; cationic polyacrylamide, and mixtures thereof.

[0186] The detergents herein, such as heavy duty laundry detergent compositions, may optionally further comprise at least one dye transfer inhibiting agent, examples of which are described above.

[0187] The detergents herein, such as heavy-duty laundry detergent compositions, may optionally include silicone or fatty acid based foam suppressors; hueing dyes, calcium and magnesium cations, visual signaling ingredients, antifoaming agents (0.001 wt % to about 4.0 wt %), and / or structurants / thickeners (0.01 wt % to 5 wt %) selected from the group consisting of diglycerides and triglycerides, ethylene glycol distearate, microcrystalline cellulose, microcellulose, biopolymers, xanthan gum, gellan gum, and mixtures thereof). Structurants may also be referred to as structural agents.

[0188] For example, the detergent herein can be in the form of a heavy-duty dry / solid laundry detergent composition. Such a detergent may include: (i) a cleaning surfactant, such as any anionic cleaning surfactant disclosed herein, any nonionic cleaning surfactant disclosed herein, any cationic cleaning surfactant disclosed herein, any zwitterionic and / or amphoteric cleaning surfactant disclosed herein, any amphoteric surfactant, any semi-polar nonionic surfactant, and mixtures thereof; (ii) a builder, such as any phosphate-free builder (e.g., a zeolite builder in the range of 0 wt % to less than 10 wt %), any phosphate builder (e.g., , sodium tripolyphosphate in the range of 0 wt % to less than 10 wt %), citric acid, citrates and nitrilotriacetic acid, any silicate (e.g., sodium silicate or potassium silicate or sodium metasilicate in the range of 0 wt % to less than 10 wt %); any carbonate (e.g., sodium carbonate and / or sodium bicarbonate in the range of 0 wt % to less than 80 wt %) and mixtures thereof; (iii) bleaching agents, such as any photobleach (e.g., sulfonated zinc phthalocyanine, sulfonated aluminum phthalocyanine, xanthene dyes and mixtures thereof); any hydrophobic or hydrophilic bleach activator (e.g., dodecanoyl phthalocyanine); any preformed hydrophilic and / or hydrophobic peracid (e.g., percarboxylic acids and salts, percarbonic acids and salts, periodic acids and salts, peroxymonosulfuric acids and salts, and mixtures thereof). salts, and mixtures thereof); and / or (iv) any other components such as bleach catalysts (e.g., imine bleach boosters, examples of which include iminium cations and polyanions, imine zwitterions, modified amines, modified amine oxides, N-sulfonyl imines, N-phosphonyl imines, N-acyl imines, thiadiazole dioxides, perfluoroimines, cyclic sugar ketones, and mixtures thereof) and metal-containing bleach catalysts (e.g., copper, iron, titanium, ruthenium, tungsten, molybdenum or manganese cations and auxiliary metal cations such as zinc or aluminum and chelates such as EDTA, ethylenediaminetetrakis(methylenephosphonic acid)).

[0189] Detergents herein, such as detergents for fabric care (e.g., clothing), may be contained in, for example, unit doses (e.g., pouches or sachets). The form of a unit dose may include a water-soluble outer film that completely encapsulates a liquid or solid detergent composition. A unit dose may include a single compartment, or at least two, three, or more (multiple) compartments. Multiple compartments may be arranged in a stacked orientation or side-by-side orientation. A unit dose herein is typically a closed structure of any form / shape that is suitable for containing and protecting its contents without allowing the contents to be released before contact with water.

[0190] In some aspects, the composition comprising at least one glucan ester derivative herein can be in the form of a fabric softener or comprise a fabric softener (liquid fabric softener). Examples of such compositions are rinse agents typically used in washing the fabric-containing material herein after cleaning the fabric-containing material with a laundry detergent composition (e.g., a laundry rinse agent, such as used in a laundry rinse cycle in a washing machine). The concentration of the glucan ester derivative in the composition comprising a fabric softener (e.g., a rinse agent) can be, for example, about or at least about 20, 30, 40, 50, 60, 70, 80, 20-80, 20-70, 20-60, 30-80, 30-70, 30-60, 40-80, 40-70, or 40-60 ppm. The concentration of fabric softener in the composition (e.g., rinse agent) can be, for example, about or at least about 50, 75, 100, 150, 200, 300, 400, 500, 600, 50-600, 50-500, 50-400, 50-300, 50-200, 100-600, 100-500, 100-400, 100-300, 100-200, 10-600, 50-500, 50-400, 50-300, 50-200, 200-600, 200-500, 200-400, or 200-300 ppm. The fabric softener concentration can be based on the total fabric softener composition added (not necessarily on a separate fabric softener component), or on one or more fabric softeners in the fabric softener formulation. Fabric softener herein can further include one or more of for example the following: fabric softener (for example, diethyl dimethyl ammonium chloride), antistatic agent, perfume, wetting agent, viscosity modifier (for example, calcium chloride), pH buffer / buffering agent (for example, formic acid), antimicrobial agent, antioxidant, free radical scavenger (for example, ammonium chloride), chelating agent / builder (for example, diethylenetriamine pentaacetate), defoamer / lubricant (for example, polydimethylsiloxane), preservative (for example, benzisothiazolinone) and colorant. In some respects, fabric softener can further include one or more of the following: fabric softener, viscosity modifier, pH buffer / buffering agent, free radical scavenger, chelating agent / builder and defoamer / lubricant. Fabric softener can be free of perfume and / or free of dye, or have perfume and / or dye less than about 0.1wt% in some respects.In some aspects, fabric softeners suitable for use herein may be as disclosed in any of U.S. Patent Application Publication Nos. 2014 / 0366282, 2001 / 0018410, 2006 / 0058214, 2021 / 0317384, or 2006 / 0014655, or International Patent Application Publication Nos. WO 2007 / 078782, WO 1998 / 016538, WO 1998 / 012293, WO 1998007920, WO 2000 / 070004, WO 2009 / 146981, WO 2000 / 70005, or WO 2013087366, which are incorporated herein by reference. If desired, some brands of fabric softeners that may be suitable for use herein include DOWNY, DOWNY ULTRA, DOWNY INFUSIONS, ALL, SNUGGLE, LENOR, and GAIN. In some aspects, liquid fabric softener products (e.g., as present before being used in a clothing rinse cycle) may be formulated to include one or more glucan ester derivatives. In some aspects, fabric softeners may be in unit doses, such as disclosed herein for detergents.

[0191] The composition comprising at least one glucan ester derivative disclosed herein can be, for example, in the form of a dishwashing detergent composition or include a dishwashing detergent composition. Examples of dishwashing detergents include automatic dishwashing detergents (typically used in dishwashing machines) and hand-washing dishwashing detergents. The dishwashing detergent composition can be, for example, in any dry or liquid / aqueous form as disclosed herein. The components that may be included in some aspects of the dishwashing detergent composition include, for example, one or more of the following: phosphates; oxygen- or chlorine-based bleaching agents; nonionic surfactants; alkaline salts (e.g., metasilicates, alkali metal hydroxides, sodium carbonate); any active enzyme disclosed herein; anticorrosives (e.g., sodium silicate); defoamers; additives that slow down the removal of glaze and patterns from ceramics; spices; anti-caking agents (in granular detergents); starch (in tablet-based detergents); gelling agents (in liquid / gel-based detergents); and / or sand (powdered detergents).

[0192] Dishwashing detergents such as automatic dishwashing machine detergents or liquid dishwashing detergents may contain (i) a nonionic surfactant including any ethoxylated nonionic surfactant, alcohol alkoxylated surfactant, epoxy-terminated poly(oxyalkylated) alcohol, or an amine oxide surfactant present in an amount from 0 to 10 wt %; (ii) about 5-60 wt % of a builder including any phosphate builder (e.g., monophosphate, diphosphate, tripolyphosphate, other oligomeric polyphosphates, sodium tripolyphosphate-STPP), any phosphate-free builder (e.g., amino acid-based compounds including methyl-glycine-diacetic acid [MGDA] and its salts or derivatives, glutamic acid-N,N-diacetic acid [GLDA] and its salts or derivatives, iminodisuccinic acid (IDS) and its salts or derivatives, carboxymethyl inulin and its salts or derivatives, nitrilotriacetic acid [NTA], diethylenetriaminepentaacetic acid [DTPA], B-alaninediacetic acid [B-ADA] and its salts), homopolymers and copolymers of polycarboxylic acids and their partially or fully neutralized salts, monomeric polycarboxylic acids and hydroxycarboxylic acids and their salts in the range of 0.5 wt % to 50 wt %, or sulfonated / carboxylated polymers in the range of about 0.1 wt % to about 50 wt %; (iii) a drying aid in the range of about 0.1 wt % to about 10 wt % (e.g., polyesters, especially anionic polyesters (optionally with 3 to 4% esters having condensation-favoring properties) 6 functional groups - typically acid, alcohol or ester functional groups) together with additional monomers), polycarbonate-, polyurethane- and / or polyurea-polyorganosiloxane compounds or precursor compounds thereof, in particular reactive cyclic carbonate and urea types); (iv) from about 1 wt % to about 20 wt % of silicates (e.g. sodium or potassium silicates, such as sodium disilicate, sodium metasilicate and crystalline phyllosilicates); (v) inorganic bleaches (e.g. peroxyhydrate salts such as perborates, percarbonates, perphosphates, persulfates and persilicates) and / or organic bleaches (e.g. organic peroxyacids such as diacyl- and tetraacylperoxides, in particular diperoxydodecanedioic acid, diperoxytetradecandioic acid and diperoxyhexadecanedioic acid); (vi) bleach activators (e.g., organic peracid precursors in the range of from about 0.1 wt% to about 10 wt%) and / or bleach catalysts (e.g., manganese triazacyclononane and related complexes; Co, Cu, Mn and Fe bispyridylamine and related complexes; and cobalt(III) pentamineacetate and related complexes); (vii) metal care agents in the range of from about 0.1 wt% to 5 wt% (e.g., benzotriazoles, metal salts and complexes, and / or silicates); (viii) glass corrosion inhibitors in the range of from about 0.1 wt% to 5 wt% (e.g., salts and / or complexes of magnesium, zinc, or bismuth); and / or (ix) any active enzyme disclosed herein (in the range of from about 0.01 to 5.0 mg active enzyme / gram automatic dishwashing detergent composition) and enzyme stabilizer components (e.g., oligosaccharides, polysaccharides and inorganic divalent metal salts). In some aspects, the dishwashing detergent ingredients or the entire composition (but correspondingly suitable for containing the glucan ester derivatives herein) can be as disclosed in U.S. Patent Nos. 8,575,083 or 9,796,951, or U.S. Patent Application Publication No. 2017 / 0044468, each of which is incorporated herein by reference. .

[0193] Detergents herein such as those for dish care may be contained, for example, in unit doses (eg, sachets or pouches) (eg, water-soluble unit dose articles) and may be as described above for fabric care detergents, but comprising a suitable dishwashing detergent composition.

[0194] It is believed that many commercially available detergent formulations may be suitable for including the glucan ester derivatives as disclosed herein. Examples of commercially available detergent formulations include ULTRAPACKS (Henkel), QUANTUM (Reckitt Benckiser), CLOROX TM 2PACKS (Clorox), OXICLEAN MAX FORCE POWER PAKS (Church & Dwight), STAIN RELEASE, ACTIONPACS, and PODST M (Procter & Gamble).

[0195] The compositions disclosed herein comprising at least one glucan ester derivative can be, for example, in the form of an oral care composition or include an oral care composition. Examples of oral care compositions include dentifrices, toothpastes, mouthwashes, mouth rinses, chewing gums, and edible strips that provide a form of oral care (e.g., treating or preventing cavities [caries], gingivitis, plaque, tartar, and / or periodontal disease). Oral care compositions can also be used to treat "oral surfaces," which encompass any soft or hard surface in the oral cavity, including the following surfaces: the tongue, hard and soft palates, buccal mucosa, gums, and surfaces of teeth. "Tooth surfaces" herein are surfaces of natural teeth or hard surfaces of artificial dentition (including, for example, crowns, caps, fillings, bridges, dentures, or dental implants).

[0196] The oral care compositions herein may include, for example, about 0.01-15.0 wt% (e.g., ~0.1-10 wt% or ~0.1-5.0 wt%, ~0.1-2.0 wt%) of a glucan ester derivative as disclosed herein. The glucan ester derivative included in the oral care composition may sometimes be provided therein as a thickener and / or dispersant that can be used to impart a desired consistency and / or mouthfeel to the composition. One or more other thickeners or dispersants may also be provided in the oral care composition herein, such as, for example, carboxyvinyl polymers, carrageenan (e.g., L-carrageenan), natural gums (e.g., karaya, xanthan gum, gum arabic, tragacanth), colloidal magnesium aluminum silicate, or colloidal silicon dioxide.

[0197] The oral care composition of this paper can be, for example, toothpaste or other dentifrice. Such composition and any other oral care composition of this paper can additionally include, but are not limited to, one or more anticaries, antimicrobial or antibacterial agents, anticalculus or tartar control agents, surfactants, abrasives, pH regulators, foam regulators, wetting agents, flavoring agents, sweeteners, pigments / colorants, whitening agents and / or other suitable components. The example of the oral care composition of the glucan ester derivatives herein can be added thereto is disclosed in U.S. Patent Application Publication Nos. 2006 / 0134025, 2002 / 0022006 and 2008 / 0057007, which are incorporated herein by reference.

[0198] The anticaries agent herein can be an orally acceptable fluoride ion source. Suitable sources of fluoride ions include, for example, fluoride, monofluorophosphate and fluorosilicate and amine fluoride, including olafluor (N'-octadecyltrimethylenediamine-N,N,N'-tris(2-ethanol)-dihydrofluoride). For example, the anticaries agent can be present in an amount providing a total of about 100-20000ppm, about 200-5000ppm or about 500-2500ppm fluoride ions to the composition. In an oral care composition where sodium fluoride is the only source of fluoride ions, for example, an amount of about 0.01-5.0wt%, about 0.05-1.0wt%, or about 0.1-0.5wt% sodium fluoride can be present in the composition.

[0199] Antimicrobial or antibacterial agents suitable for use in the oral care compositions herein include, for example, phenolic compounds (e.g., 4-allylcatechol; parabens such as benzyl paraben, butyl paraben, ethyl paraben, methyl paraben, and propyl paraben; 2-benzylphenol; butylated hydroxyanisole; butylated hydroxytoluene; capsaicin; carvacrol; wood tar alcohol; eugenol; guaiacol; halogenated bisphenols such as hexachlorobenzene; phenol (hexachlorophene) and bromochlorophene; 4-hexylresorcinol; 8-hydroxyquinoline and its salts; salicylates such as menthyl salicylate, methyl salicylate and phenyl salicylate; phenol; pyrocatechol; N-salicylicylanilide; thymol; halogenated diphenyl ether compounds such as triclosan and triclosan monophosphate); copper (II) compounds (e.g., copper (II) chloride, fluoride, sulfate and hydroxides); zinc ion sources (e.g., zinc acetate, citrate, gluconate, glycinate, oxide and sulfate); phthalic acid and its salts (e.g., magnesium monopotassium phthalate); bisoctin; octenidinium; sanguinarine; benzalkonium chloride; dofenphen; alkylpyridinium chlorides (e.g., hexadecylpyridinium chloride, tetradecylpyridinium chloride, N-tetradecyl-4-ethylpyridinium chloride); iodine; sulfonamides; biguanides (e.g., Alexidine, hexyl chloramine, , chlorhexidine digluconate); azacyclohexane derivatives (e.g., delmopinol, octopirox); magnolia extract, grape seed extract, rosemary extract, menthol, geraniol, citral, eucalyptol; antibiotics (e.g., vogelmantin, amoxicillin, tetracycline, doxycycline, minocycline, metronidazole, neomycin, kanamycin, clindamycin), and / or any antibacterial agent disclosed in U.S. Pat. No. 5,776,435 (incorporated herein by reference). One or more antimicrobial agents may optionally be present in about 0.01-10 wt % (e.g., 0.1-3 wt %), for example, in the disclosed oral care composition.

[0200] Anti-calculus or tartar control agents suitable for use in the oral care compositions herein include, for example, phosphates and polyphosphates (e.g., pyrophosphates), polyaminopropanesulfonic acid (AMPS), zinc citrate trihydrate, polypeptides (e.g., polyaspartic acid and polyglutamic acid), polyolefin sulfonates, polyolefin phosphates, bisphosphonates (e.g., azacycloalkane-2,2-bisphosphonates such as azacycloheptane-2,2-bisphosphonic acid), N-methylazacyclopentane-2,3-bisphosphonic acid, ethane-1-hydroxy-1,1-bisphosphonic acid (EHDP), ethane-1-amino-1,1-bisphosphonates and / or phosphonoalkanecarboxylic acids and salts thereof (e.g., alkali metal and ammonium salts thereof). Useful inorganic phosphates and polyphosphates include, for example, monobasic, dibasic and tribasic sodium phosphates; sodium tripolyphosphate; tetrapolyphosphate; monosodium, disodium, trisodium and tetrasodium pyrophosphate; disodium dihydrogen pyrophosphate; sodium trimetaphosphate; sodium hexametaphosphate; or any of these in which the sodium is replaced by potassium or ammonium. In certain embodiments, other useful anticalculus agents include anionic polycarboxylate polymers (e.g., polymers or copolymers of acrylic acid, methacrylic acid and maleic anhydride, such as polyvinyl methyl ether / maleic anhydride copolymers). Other useful anticalculus agents include chelating agents such as hydroxycarboxylic acids (e.g., citric acid, fumaric acid, malic acid, glutaric acid and oxalic acid and salts thereof) and aminopolycarboxylic acids (e.g., EDTA). One or more anticalculus or tartar control agents may optionally be present in about 0.01-50 wt % (e.g., about 0.05-25 wt % or about 0.1-15 wt %), for example in the disclosed oral care compositions.

[0201] Surfactants suitable for use in the oral care compositions herein may be, for example, anionic, nonionic or amphoteric. Suitable anionic surfactants include, but are not limited to, C 8-20 Water-soluble salts of alkyl sulfates, C 8-20 Fatty acid sulfonated monoglycerides, sarcosinates and taurates. Examples of anionic surfactants include sodium lauryl sulfate, sodium coconut monoglyceride sulfonate, sodium lauryl sarcosinate, sodium lauryl hydroxyethyl sulfonate, sodium polyethylene glycol monolauryl ether carboxylate and sodium dodecylbenzene sulfonate. Suitable nonionic surfactants include, but are not limited to, poloxamers, polyoxyethylene sorbitan esters, fatty alcohol ethoxylates, alkylphenol ethoxylates, tertiary amine oxides, tertiary phosphine oxides and dialkyl sulfoxides. Suitable amphoteric surfactants include, but are not limited to, C 2+ with anionic groups such as carboxylate, sulfate, sulfonate, phosphate or phosphonate. 8-20 Derivatives of fatty secondary and tertiary amines. An example of a suitable amphoteric surfactant is cocamidopropyl betaine. One or more surfactants are optionally present in, for example, the disclosed oral care compositions in a total amount of about 0.01-10 wt % (e.g., about 0.05-5.0 wt % or about 0.1-2.0 wt %).

[0202] Abrasives suitable for use in the oral care compositions herein may include, for example, silica (e.g., silica gel, hydrated silica, precipitated silica), alumina, insoluble phosphates, calcium carbonate, and resin abrasives (e.g., urea-formaldehyde condensate products). Examples of insoluble phosphates useful as abrasives herein are orthophosphates, polymetaphosphates, and pyrophosphates, and include dicalcium orthophosphate dihydrate, calcium pyrophosphate, beta-calcium pyrophosphate, tricalcium phosphate, calcium polymetaphosphate, and insoluble sodium polymetaphosphate. One or more abrasives are optionally present in, for example, the disclosed oral care compositions in a total amount of about 5-70 wt % (e.g., about 10-56 wt % or about 15-30 wt %). In certain embodiments, the average particle size of the abrasive is about 0.1-30 microns (e.g., about 1-20 microns or about 5-15 microns).

[0203] In certain embodiments, the oral care composition may include at least one pH adjusting agent. Such agents may be selected to acidify the pH of the composition, make it more alkaline, or buffer it to a pH range of about 2-10 (e.g., a pH range of about 2-8, 3-9, 4-8, 5-7, 6-10, or 7-9). Examples of pH adjusting agents that can be used herein include, but are not limited to, carboxylic acids, phosphoric acids, and sulfonic acids; acid salts (e.g., monosodium citrate, disodium citrate, monosodium malate); alkali metal hydroxides (e.g., sodium hydroxide, carbonates such as sodium carbonate, bicarbonate, sodium sesquicarbonate); borates; silicates; phosphates (e.g., monosodium phosphate, trisodium phosphate, pyrophosphate); and imidazoles.

[0204] The foam regulator suitable for use in the oral care composition of the present invention can be, for example, polyethylene glycol (PEG). High molecular weight PEG is suitable, including, for example, those having an average molecular weight of about 200,000-7,000,000 (e.g., about 500,000-5,000,000 or about 1,000,000-2,500,000). One or more PEGs are optionally present in a total amount of about 0.1-10 wt % (e.g., about 0.2-5.0 wt % or about 0.25-2.0 wt %), for example, in the disclosed oral care composition.

[0205] In certain embodiments, the oral care composition may include at least one humectant. In certain embodiments, the humectant may be a polyol, such as glycerol, sorbitol, xylitol, or a low molecular weight PEG. The most suitable humectant may also be used as a sweetener herein. One or more humectants are optionally present in, for example, the disclosed oral care composition in an amount of about 1.0-70wt% (e.g., about 1.0-50wt%, about 2-25wt%, or about 5-15wt%).

[0206] Natural or artificial sweeteners may be optionally included in the oral care compositions of this invention. Examples of suitable sweeteners include dextrose, sucrose, maltose, dextrin, invert sugar, mannose, xylose, ribose, fructose, levulose, galactose, corn syrup (e.g., high fructose corn syrup or corn syrup solids), partially hydrolyzed starch, hydrogenated starch hydrolysate, sorbitol, mannitol, xylitol, maltitol, isomalt, aspartame, neotame, saccharin and its salt, strong sweeteners and cyclamate based on dipeptides. One or more sweeteners are optionally present in, for example, the disclosed oral care compositions in a total amount of about 0.005-5.0wt%.

[0207] Natural or artificial flavorants may optionally be included in the oral care compositions of the present invention. Examples of suitable flavorants include vanillin; sage; marjoram; celery oil; spearmint oil; cinnamon oil; wintergreen oil (methyl salicylate); peppermint oil; clove oil; bay oil; anise oil; eucalyptus oil; citrus oils; fruit oils; essences, such as those derived from lemons, oranges, limes, grapefruits, apricots, bananas, grapes, apples, strawberries, cherries, or pineapples; flavors derived from beans and nuts, such as coffee, cocoa beans, cola, peanuts, or almonds; and adsorbed and encapsulated flavorants. Also included in the flavorants of the present invention are ingredients that provide flavor and / or other sensory effects in the mouth, including cooling or warming effects. Such ingredients include, but are not limited to, menthol, menthyl acetate, menthyl lactate, camphor, eucalyptus oil, eucalyptol, anethole, eugenol, cinnamon, oxanone, Hydroxymethylanethole, thymol, linalool, benzaldehyde, cinnamaldehyde, N-ethyl-p-menthane-3-carboxamide, N, 2,3-trimethyl-2-isopropylbutanamide, 3-(1-menthoxy)-propane-1,2-diol, cinnamaldehyde glycerol acetal (CGA) and menthone glycerol acetal (MGA). One or more flavorants are optionally present in a total amount of about 0.01-5.0 wt % (e.g., about 0.1-2.5 wt %), for example, in the disclosed oral care composition.

[0208] In certain embodiments, the oral care composition may include at least one bicarbonate. Any orally acceptable bicarbonate may be used, including, for example, alkali metal bicarbonates such as sodium bicarbonate or potassium bicarbonate, and ammonium bicarbonate. For example, one or more bicarbonates are optionally present in the disclosed oral care composition in a total amount of about 0.1-50 wt % (e.g., about 1-20 wt %).

[0209] In certain embodiments, the oral care composition may include at least one whitening agent and / or coloring agent. Suitable whitening agents are peroxide compounds, such as any of those disclosed in U.S. Pat. No. 8,540,971, which is incorporated herein by reference. Herein, suitable coloring agents include, for example, pigments, dyes, lakes, and agents that impart a particular gloss or reflectivity, such as pearlescent agents. Specific examples of coloring agents that can be used herein include talc; mica; magnesium carbonate; calcium carbonate; magnesium silicate; magnesium aluminum silicate; silicon dioxide; titanium dioxide; zinc oxide; red, yellow, brown, black iron oxides; ammonium ferrocyanide; manganese violet; dark blue; titanium mica; and bismuth oxychloride. For example, one or more coloring agents are optionally present in the disclosed oral care composition in a total amount of about 0.001-20 wt % (e.g., about 0.01-10 wt % or about 0.1-5.0 wt %).

[0210] Additional components that may be optionally included in the oral compositions herein include, for example, one or more enzymes (above), vitamins, and anti-adhesive agents. Examples of vitamins that may be used herein include vitamin C, vitamin E, vitamin B5, and folic acid. Examples of suitable anti-adhesive agents include methyl paraben (solbrol), ficin, and quorum sensing inhibitors.

[0211] Additional examples of personal care, home care and other products and ingredients herein may be any of those disclosed in U.S. Patent No. 8796196, which is incorporated herein by reference. Examples of personal care, home care and other products and ingredients herein include fragrances, aromatics, insect repellents and insecticides, foaming agents such as surfactants, pet insecticides, pet shampoos, disinfectants, hard surface (e.g., floors, tubs / showers, sinks, toilets, door handles / panels, glass / windows, exterior or interior of cars / automobiles) treatment agents (e.g., cleaning, disinfecting, and / or coating agents), wipes and other nonwoven materials, colorants, preservatives, antioxidants, emulsifiers, emollients, oils, medicaments, flavoring agents and suspending agents.

[0212] The present disclosure also relates to a method of treating a material. The method comprises contacting the material with an aqueous composition comprising at least one glucan ester derivative disclosed herein.

[0213] In some aspects, the material contacted with the aqueous composition in the contact method herein can include a fabric. The fabric herein can include natural fibers, synthetic fibers, semi-synthetic fibers, or any combination thereof. The semi-synthetic fibers herein are produced using naturally occurring materials that have been chemically derivatized, an example of which is rayon. Non-limiting examples of fabric types herein include fabrics made from: (i) cellulosic fibers such as cotton (e.g., velvet, canvas, striped or checked cloth, chenille, chintz, corduroy, drapery, damask, denim, flannel, gingham, jacquard, knits, matelassé, oxford, percale, poplin, plissé, sateen, seersucker, sheer fabric, terry, twill, velvet), rayon (e.g., viscose, modal, lyocell), linen, and (ii) protein fibers such as silk, wool and related mammalian fibers; (iii) synthetic fibers such as polyester, acrylic, nylon, etc.; (iv) long plant fibers from jute, flax, ramie, coir, kapok, sisal, henna, abaca, hemp and tamarind; and (v) any combination of fabrics of (i)-(iv). Fabrics comprising a combination of fiber types (e.g., natural and synthetic) include, for example, those having both cotton and polyester. Materials / articles containing one or more fabrics herein include, for example, clothing, curtains, drapes, upholstery, carpets, bed linens, bath linens, tablecloths, sleeping bags, tents, automotive interiors, etc. Other materials include natural and / or synthetic fibers including, for example, nonwoven fabrics, pads, paper, and foams.

[0214] The aqueous composition contacted with the fabric can be, for example, a fabric care composition (e.g., laundry detergent, fabric softener). Thus, if a fabric care composition is used in a treatment method, the treatment method can be considered in certain embodiments as a fabric care method or a laundry method. It is expected that the fabric care composition herein can achieve one or more of the following fabric care benefits (i.e., surface substantial effects): wrinkle removal, wrinkle reduction, wrinkle resistance, reduced fabric wear, anti-fabric wear, reduced fabric pilling, extended fabric life, fabric color retention, reduced fabric fading, reduced dye transfer, restored fabric color, reduced fabric staining, released fabric soil, maintained fabric shape, enhanced fabric smoothness, prevented soil redeposition on fabric, prevented clothing from graying, improved fabric feel / texture (hand / handle) and / or reduced fabric shrinkage.

[0215] Examples of conditions (e.g., time, temperature, wash / rinse volume) for performing fabric care methods or laundry methods herein are disclosed in WO 1997 / 003161 and U.S. Pat. Nos. 4,794,661, 4,580,421, and 5,945,394, which are incorporated herein by reference. In other examples, the material comprising the fabric may be contacted with the aqueous composition herein: (i) for at least about 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, or 120 minutes; (ii) at a temperature of at least about 10° C., 15° C., 20° C., 25° C., 30° C., 35° C., 40° C., 45° C., 50° C., 55° C., 60° C., 65° C., 70° C., 75° C., 80° C., 85° C., 90° C., or 95° C. (e.g., for laundry washing or rinsing) : a “cold” temperature of about 15°C-30°C, a “warm” temperature of about 30°C-50°C, a “hot” temperature of about 50°C-95°C); (iii) at a pH of about 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 (e.g., a pH range of about 2-12 or about 3-11); (iv) at a salt (e.g., NaCl) concentration of at least about 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, or 4.0 wt %; or any combination of (i)-(iv).

[0216] For example, the contacting step in the fabric care method or laundry method may include any of the washing, soaking and / or rinsing steps. In yet other embodiments, contacting with the material or fabric may be performed by any means known in the art, such as dissolving, mixing, shaking, spraying, treating, dipping, rinsing, pouring or pouring, combining, painting, coating, applying, pasting and / or communicating an effective amount of the polyglucan ester derivative herein with the fabric or material. In yet other embodiments, contacting may be used to treat fabrics to provide a substantial surface effect. As used herein, the term "fabric hand" or "handle" refers to an individual's tactile sensory response to a fabric that may be physical, physiological, psychological, social, or any combination thereof. In one embodiment, fabric hand may be measured using a relative hand value. The relative hand value of textiles was measured using a 300nm process (available from Nu Cybertek, Inc. Davis, CA) (American Association of Textile Chemists and Colorists [AATCC Test Method “202-2012. Relative Hand Value of Textiles: Instrumental Method”]).

[0217] In some aspects of treating materials comprising fabrics, the glucan ester derivatives of the aqueous composition are adsorbed to the fabrics. It is believed that this feature allows the glucan ester derivatives herein to be used as anti-redeposition agents and / or anti-greying agents in fabric care compositions (e.g., in addition to their viscosity-adjusting effects). The anti-redeposition agents or anti-greying agents herein help prevent stains from being redeposited on clothing in the wash water after they have been removed. In some aspects, it is further contemplated that adsorption of the glucan ester derivatives herein to fabrics enhances the mechanical properties of the fabrics.

[0218] For example, colorimetric techniques can be used (e.g., Dubois et al., 1956, Anal. Chem. 28:350-356; et al., 2006, Lenzinger Berichte [Lenzinger Report] 85: 68-76; both incorporated herein by reference) or any other method known in the art to measure the adsorption of the glucan ester derivatives herein to fabrics.

[0219] Other materials that can be contacted in the above-mentioned treatment method include surfaces that can be treated with dishwashing detergents (e.g., automatic dishwashing detergents or hand-washing dishwashing detergents). Examples of such materials include surfaces of tableware, glassware, basins, dishware, baking trays, cookware, and flatware (collectively referred to herein as "tableware") made of ceramic materials, porcelain, metals, glass, plastics (e.g., polyethylene, polypropylene, polystyrene, melamine, etc.) and wood. Therefore, in certain embodiments, the treatment method can be considered to be, for example, a dishwashing method or a tableware washing method. Examples of conditions (e.g., time, temperature, washing volume) for carrying out dishwashing or tableware washing methods herein are disclosed in this article and in U.S. Patent No. 8575083 and U.S. Patent Application Publication No. 2017 / 0044468, which are incorporated herein by reference. In some aspects, tableware products can be contacted with the aqueous composition herein under a set of suitable conditions, such as any one of the above disclosed conditions for contacting with a fabric-containing material.

[0220] Other materials that may be contacted in the above-mentioned treatment methods include oral surfaces, such as any soft or hard surface in the oral cavity, including the surfaces of the tongue, hard and soft palate, buccal mucosa, gums, and tooth surfaces (e.g., hard surfaces of natural teeth or artificial dentition (such as crowns, caps, fillings, bridges, dentures, or dental implants)). Thus, in certain embodiments, the treatment methods may be considered to be, for example, oral care methods or tooth care methods. The conditions (e.g., time, temperature) for contacting the oral surfaces with the aqueous composition herein should be suitable for the intended purpose of such contact. Other surfaces that may be contacted in the treatment methods also include surfaces of the skin system such as skin, hair, or nails (i.e., any tissue or material comprising keratin).

[0221] Thus, some aspects of the present disclosure relate to materials comprising the glucan ester derivatives herein (e.g., fabrics or fibers comprising products as disclosed herein, or any other material herein, such as hair, skin, or other keratin-containing materials). Such materials can be prepared, for example, according to the material treatment methods disclosed herein. In some aspects, a material can comprise a glucan ester derivative if the glucan ester derivative is adsorbed to or otherwise in contact with the surface of a material (e.g., a glucan ester contained in a coating of a material).

[0222] Some aspects of the methods of treating materials herein further include a drying step, wherein the material is dried after contacting with the aqueous composition. The drying step may be performed directly after the contacting step, or after one or more additional steps that may follow the contacting step (e.g., drying fabrics, dishes, or hair after washing in the aqueous composition herein, e.g., after rinsing in water). Drying may be performed by any of several methods known in the art, such as air drying (e.g., about 20° C.-25° C.), or, for example, at a temperature of at least about 30° C., 40° C., 50° C., 60° C., 70° C., 80° C., 90° C., 100° C., 120° C., 140° C., 160° C., 170° C., 175° C., 180° C., or 200° C. The material that has been dried herein typically has less than 3 wt%, 2 wt%, 1 wt%, 0.5 wt%, or 0.1 wt% water contained therein.

[0223] The aqueous composition used in the treatment method herein can be any aqueous composition disclosed herein. Examples of aqueous compositions include detergents (e.g., laundry detergents or dishwashing detergents), fabric softeners, aqueous dentifrice (such as toothpaste), and hair care products (such as hair styling, hair cleaning, or hair conditioning products).

[0224] Some aspects of the present invention relate to a method for styling hair. Such a method may include, for example, at least steps (a) and (b), or steps (c) and (d), as follows:

[0225] (a) contacting (e.g., applying) the hair with a composition comprising the glucan ester derivative herein, thereby providing treated hair (or coated hair), and

[0226] (b) bringing said treated hair (or said coated hair) into a desired form; or

[0227] (c) placing the hair in a desired form, and

[0228] (d) contacting (e.g., coating) the hair of step (c) with a composition comprising a glucan ester derivative herein, thereby providing treated hair (or coated hair); and

[0229] (e) optionally, removing the solvent, if any, used to deliver the glucan ester derivative to the hair in step (a) or (d).

[0230] Such a method may optionally be characterized as a hair styling method. For example, contacting in a hair styling method may be performed by applying / treating hair with a hair styling composition (e.g., gel, mousse, spray) herein comprising at least one glucan ester derivative. The hair to be treated in the hair styling method, particularly in step (a) or (d), may typically be wet or dry. The step (e) of removing the solvent may be performed, for example, by drying, such as by a drying method disclosed herein (e.g., air drying or blow drying with room temperature or heated air). Drying may be performed with or without agitation of the treated hair, such as by combing or wiping while drying. Optionally, the styling method herein may include a step of applying steam to the treated hair after step (b) or step (d) (but before optional step [e]). In some aspects, step (b) or (c) of placing the hair in a desired form may be performed by straightening, curling, or otherwise placing the hair in a form different from the form of the hair that existed before step (a), (b) or (c). The hair styled by the styling methods herein can optionally be maintained in a desired form for a period of, for example, at least 1, 2, 3, 4, 5, or more days without applying any device and / or additional material to the styled hair (i.e., in a free-standing state). Such style retention can be under conditions such as dry air (e.g., relative humidity ≤ 50%) or humid air (e.g., relative humidity exceeding 50%) (typically for a period of time during which the styled hair is not washed or rinsed).

[0231] In some respects, the material that can be treated with the aqueous composition (for example, dispersion / emulsion) herein is a nonwoven product. The application of the aqueous composition (at any concentration disclosed herein) herein can be related to, typically followed by a drying step (for example, air drying, heat drying, vacuum drying; the drying temperature can be any suitable temperature disclosed herein, for example) This treatment can strengthen the nonwoven product (that is, used as its adhesive). In some respects, the dry or wet tensile strength (measured in N / 5cm) of non-woven fabrics can be increased by, for example, about or at least about 1000%, 10000%, 100000% or 1000000% as disclosed herein by the glucan ester derivatives. Therefore, further provided herein is a nonwoven product containing an adhesive / reinforcer comprising the glucan ester derivatives disclosed herein. In some respects, the dry or wet tensile strength of the nonwoven comprising the glucan ester derivative herein can be about or at least about 10, 15, 20, 25, 50, 75, 100, 125, 130, 135, 140, 145, 150, 10-150, 15-150, 20-150, 25-150, 10-140, 15-140, 20-140 or 25-140 N / 5cm. Based on the gross weight of nonwoven material and glucan ester derivative in nonwoven product, the content of glucan ester derivative therein can be about 1, 2, 5, 10, 15, 20, 25, 1-5, 1-10, 5-20 or 1-25wt%. Nonwoven product herein can be for example air-laid, dry-laid, wet-laid, combed, electrospinning, spunlace, spunbond or melt-blown. In some aspects, the nonwoven product can be an abrasive or scouring sheet, an agricultural mulch, an agricultural seed strip, a garment lining, an automotive roof lining or interior trim, a bib, a cheese wrap, a geotextile, a coffee filter, a cosmetic remover or applicator, a detergent pouch / sachet, a fabric softener sheet, an envelope, a facial mask, a filter, a garment bag, a thermally or electrically conductive fabric, a household care wipe (e.g., for floor care, hard surface cleaning, pet care, etc.), a house covering, a hygiene product (e.g., a sanitary pad / tissue, a medical mattress), an insulation material, a label, a clothing aid, a medical care or personal injury care product (e.g., a bandage, a plaster bandage pad or plaster cover, a dressing, a bag, a sterile outer packaging, a sterile packaging, a surgical drape, a surgical gown, a swab), a mop, a napkin or tissue, paper, a personal wipe or baby wipe, a reusable bag, a roof covering, a tablecloth, a sign, a tea bag or coffee bag, an upholstery, a vacuum cleaning bag, or a wall covering. In some aspects, the fibers of the nonwoven product can comprise cellulose and / or alpha-1,3-glucan, or can comprise one or more other materials disclosed herein that can be used to form fibers.Examples of the nonwoven products, nonwoven product materials, and / or methods of producing nonwoven products and materials herein may be as disclosed in U.S. Patent Application Publication Nos. 2020 / 0370216, 2018 / 0282918, 2017 / 0167063, 2018 / 0320291, or 2010 / 0291213, each of which is incorporated herein by reference.

[0232] The composition comprising at least one glucan ester derivative as disclosed herein can be, for example, a film or coating. In some aspects, the film or coating can be a dried film or coating comprising, for example, less than about 3, 2, 1, 0.5, or 0.1 wt % of water. In some aspects, the film or coating can comprise about 20-40, 20-35, 20-30, 25-40, 25-35, or 25-30 wt % of the glucan ester derivative herein, wherein the balance of the material in the film or coating is optionally water, an aqueous solution, and / or a plasticizer. The amount of the glucan ester derivative as disclosed herein in the film or coating herein can be, for example, about or at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65 6, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 99.5, 99.9, or 100wt%. The film or coating herein can be produced, for example, by providing a layer of an aqueous dispersion or solution of a glucan ester derivative (e.g., about 5-30, 5-25, 5-20, 10-30, 10-25, or 10-20 wt % of a glucan ester) to a surface / object / material, and then removing all or most (≥90, 95, 98, 99 wt %) of the water from the dispersion or solution to produce a film or coating. For example, a method similar to U.S. Patent Application Publication No. 2018 / 0258590 (incorporated herein by reference) or as disclosed therein can be used to produce a film or coating. For example, the grammage of a coating comprising the glucan ester derivative herein on a substrate can be about or at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 1-12, 1-10, 1-8, 1-6, 1-5, 1-4, 1-3, or 1-2 gsm (grams per square meter).

[0233] The films or coatings herein can have a thickness of, for example, about, at least about, or up to about 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 2, 2.5, 5, 7.5, 10, 15.5, 15, 17.5, 20, 22.5, 25, 30, 35, 40, 45, 50, 75, 100, 150, 200, 0.5-1.5, 0.8-1.5, 1.0-1.5, 0.5-1.4, 0.8-1.4, or 1.0-1.4 mil (1 mil=0.001 inch). In some aspects, such thickness is uniform and can be characterized as having a continuous area that (i) is at least 20%, 30%, 40%, or 50% of the total film / coating area and (ii) has a standard deviation of thickness of less than about 0.06, 0.05, or 0.04 mils. In some aspects, the films or coatings herein can be characterized as thin (e.g., <2 mils). The films herein are typically cast films.

[0234] Film or coating herein can show various degrees of transparency as required.For example, film / coating can be highly transparent (for example, high light transmittance and / or low haze).Optical transparency as used herein can for example refer to allow at least about 10%-99% light transmittance or at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98% or 99% light transmittance, and / or be less than 30%, 25%, 20%, 15%, 10%, 5%, 2.5%, 2% or 1% haze film or coating.High optical transparency can optionally refer to film / coating with at least about 90% light transmittance and / or less than 10% haze. The light transmittance of the films / coatings herein can be measured, for example, following test ASTM D 1746 (2009, Standard Test Method for Transparency of Plastic Sheeting, ASTM International, West Conshohocken, PA) (incorporated herein by reference). The haze of the films / coatings herein can be measured, for example, following test ASTM D1003-13 (2013, Standard Test Method for Haze and Luminous Transmittance of Transparent Plastics, ASTM International, West Conshohocken, PA) (incorporated herein by reference).

[0235] Film or coating herein may optionally further include a plasticizer, such as glycerol, propylene glycol, ethylene glycol, and / or polyethylene glycol. In some aspects, other film components (except the composition herein) may be as disclosed in U.S. Patent Application Publication Nos. 2011 / 0151224, 2015 / 0191550, 20190153674, or 20210095155, or U.S. Patent Nos. 9688035 or 3345200, all of which are incorporated herein by reference.

[0236] In some respects, film or coating herein, or any suitable solid composition (for example, composite material, fiber, fibrid) can further comprise at least one cross-linking agent. The glucan ester derivatives of the present disclosure can be cross-linked (covalently bonded) with each other and / or with at least one other component of composition (for example, polymer, active agent) or with the component of substrate (if composition is applied to substrate). However, in some respects, the glucan ester derivatives herein are not cross-linked in any way, but one or more other components of said composition are cross-linked. Cross-linking can for example (i) enhance the tensile strength of film or coating composition and / or (ii) plasticize film or coating composition. In some respects, cross-linking can connect film or coating to substrate. In some cases, cross-linking agents such as dicarboxylic acids or polycarboxylic acids, aldehydes or polyphenols can be used to give plasticity and the feature of being connected to substrate. Suitable crosslinking agents for use in preparing compositions having crosslinking as described above are contemplated to include phosphorus oxychloride (POCl3), polyphosphates, sodium trimetaphosphate (STMP), boron-containing compounds (e.g., boric acid, diborates, tetraborates such as tetraborate decahydrate, pentaborates, polymeric compounds such as alkali metal borates), polyvalent metals (e.g., titanium-containing compounds such as ammonium titanium lactate, titanium triethanolamine, titanium acetylacetonate, or titanium polyhydroxy complexes; zirconium-containing compounds such as zirconium lactate, zirconium carbonate, zirconium acetylacetonate, zirconium triethanolamine, zirconium diisopropyl lactate, or zirconium polyhydroxy complexes), glyoxal, glutaraldehyde, acetaldehyde, polyphenols, divinyl sulfone, epichlorohydrin, polyamide-epichlorohydrin (PAE), di- or polycarboxylic acids (e.g., citric acid, malic acid, tartaric acid, succinic acid, glutaric acid, adipic acid), dichloroacetic acid, polyamines, 1,2 , 7,8-diepoxyoctane, diethylene glycol dimethyl ether (diglyme), diglycidyl ethers (e.g., diglycidyl ethers themselves, ethylene glycol diglycidyl ether [EGDGE], 1,4-butanediol diglycidyl ether [BDGE], polyethylene glycol diglycidyl ether [PEGDE, such as PEG2000DGE], 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, bisphenol A diglycidyl ether [BADGE]) and triglycidyl ethers (e.g., trimethylolpropane triglycidyl ether). Still other examples of suitable cross-linking agents are described in U.S. Pat. Nos. 4,462,917, 4,464,270, 4,477,360 and 4,799,550 and U.S. Patent Application Publication No. 2008 / 0112907, all of which are incorporated herein by reference. However, in some aspects, the cross-linking agent is not a boron-containing compound (e.g., as described above). The glucan ester derivatives herein can be cross-linked in contexts other than films or coatings (eg, in dispersions, fibers, fibrids, or other compositions disclosed herein), such as with any cross-linking agent as disclosed herein.

[0237] One or more conditioning agents may be included in the film, for example, of the coating to enhance the feel of the film or coating. The conditioning agent may be an anionic softener such as sulfated oil, soap, sulfated alcohol, and / or oil emulsion; a cationic softener such as a quaternary ammonium compound; a nonionic softener such as a polyoxyethylene derivative, a polyethylene emulsion, a wax emulsion, and / or a silicone softener; a natural fatty acid; an oil; a monoglyceride; a diglyceride; a polyglycerol ester; a citric acid ester; a lactic acid ester; and / or a sugar ester such as a sucrose ester and / or an sorbitan ester.

[0238] Also disclosed are articles comprising adhesives, films, coatings, or adhesives, which contain the glucan ester derivatives in dry form herein. Such articles (optionally, "coated articles") include a substrate having at least one surface on which a coating, adhesive, film, or adhesive is arranged / deposited in a substantially continuous or discontinuous manner. In some aspects, the article includes paper, leather, wood, metal, polymer, fibrous material, masonry, drywall, gypsum, and / or building surfaces. "Building surface" herein is the exterior or interior surface of a building or other man-made structure. In some aspects, the article includes a porous substrate such as paper, cardboard, paperboard, corrugated board, cellulose substrate, textile, or leather. However, in some aspects, the article can comprise a polymer such as a polyamide, a polyolefin, a polylactic acid, a polyethylene terephthalate (PET), a poly(trimethylene terephthalate) (PTT), an aramid, a polyethylene sulfide (PES), a polyphenylene sulfide (PPS), a polyimide (PI), a polyethylene imine (PEI), a polyethylene naphthalate (PEN), a polysulfone (PS), a polyetheretherketone (PEEK), a polyethylene, a polypropylene, a poly(cycloolefin), a poly(cyclohexylene dimethylene terephthalate), a poly(trimethylene furandicarboxylate) (PTF), or a cellophane. In some aspects, the article comprising the fibrous substrate is a fiber, a yarn, a fabric, a fabric blend, a textile, a non-woven fabric, a paper, or a carpet. The fibrous substrate may contain natural and / or synthetic fibers such as cotton, cellulose, wool, silk, rayon, nylon, aramid, acetate, polyurethaneurea, acrylic, jute, sisal, seagrass, coir, polyamide, polyester, polyolefin, polyacrylonitrile, polypropylene, polyaramid, or blends thereof.

[0239] In some respects, film, coating or other compositions (for example, composite material) herein can have grease / oil and / or oxygen barrier properties.Except the glucan ester derivatives herein, such compositions can include one or more components as disclosed in U.S. Patent Application Publication No. 20190153674 or 20210095155, each of which is incorporated herein by reference.For example, film, coating or other compositions herein can include optionally as one or more of the following of adhesive: polyvinyl alcohol, polyvinyl acetate, partially saponified polyvinyl acetate, silanol-modified polyvinyl alcohol, butene glycol vinyl alcohol copolymer (BVOH), polyurethane, starch, corn dextrin, carboxymethyl cellulose, cellulose ether, hydroxyethyl cellulose, hydroxypropyl cellulose, ethyl hydroxyethyl cellulose, methyl cellulose, alginate, sodium alginate, xanthan gum, carrageenan, casein, soy protein, guar gum, synthetic polymer, styrene butadiene latex and / or styrene acrylate latex. In some aspects, the composition for preparing a film, coating, or other composition can include about 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 65-85, 65-80, 70-85, or 70-80 wt % of a binder or compound such as polyvinyl alcohol (or any other of the compounds cited above) and about 50, 45, 40, 35, 30, 25, 20, 15, 10, 5, 2.5, 15-35, 20-35, 15-30, or 20-30 wt % of a glucan ester derivative as disclosed herein. In some aspects, the composition for preparing a film, coating, or other composition can include a ratio of about 7:3, 7.5:2.5, 8:2, 8.5:1.5, or 9:1 of a binder or compound (e.g., any of the compounds cited above such as polyvinyl alcohol or starch) to the glucan ester derivative herein, based on the wt % of each of these components in the composition. In some aspects, the film, coating, or other composition does not include starch, while in other aspects such as oxygen barriers, starch can be included (e.g., as disclosed in U.S. Patent Application Publication No. 2011 / 0135912 or U.S. Patent Nos. 5,621,026 or 6,692,801, which are incorporated herein by reference).The grease / oil barrier properties of the coating or film compositions herein can be evaluated, for example, using a standard "KIT" type test following the Technical Association of the Pulp and Paper Industry (TAPPI) Test Method T-559cm-02 (Grease resistance test for paper and paperboard, TAPPIPress, Atlanta, GA, USA; which is incorporated herein by reference). Values ​​close to 12 on a scale of 1 to 12 in this test indicate good grease / oil barrier / resistance function. If desired, grease / oil barrier properties as well as water / aqueous liquid barrier properties can be evaluated by a Cobb test. The barrier herein can have, for example, a Cobb index value of less than 20, 17.5, 15, 12.5, 10, 7.5, or 5. The oxygen barrier properties of the coating or film composition herein can be evaluated by measuring the oxygen transmission rate (OTR) of the coating; the OTR can be determined, for example, according to ASTM F-1927-07 (2007, Standard Test Method for Determination of Oxygen Gas Transmission Rate, Permeability and Permeance at Controlled Relative Humidity Through Barrier Materials Using a Coulometric Detector, ASTM International, West Conshohocken, PA) (incorporated herein by reference). For example, the OTR can be determined under conditions of relative humidity of about 50%-80%, 30%-55%, 35%-50%, or 30%-80%, and / or at a temperature of about or at least about 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, 45°C, 15°C-40°C, 15°C-35°C, 15°C-30°C, 15°C-25°C, 20°C-40°C, 20°C-35°C, 20°C-30°C, or 20°C-25°C.Examples of substrates that can utilize grease / oil and / or oxygen barrier coatings herein include any of the aforementioned substrates / surfaces, including cellulose-containing substrates (e.g., paper, paperboard, cardboard, corrugated board, textiles), polyethylene, polypropylene, polylactic acid, poly(ethylene terephthalate) (e.g., MYLAR), poly(trimethylene terephthalate), polyamides, polybutylene succinate, polybutylene adipate terephthalate, polybutylene succinate adipate, poly(trimethylene furandicarboxylate), synthetic and / or petroleum-based substrates, or bio-based substrates. Any of the aforementioned films, coatings, or other compositions may be in the form of, for example, a laminate or extruded product, and it is optionally located on any of the aforementioned substrates.

[0240] In some aspects, the film, coating, or other composition (e.g., dispersion, foam, masterbatch, composite) comprising the glucan ester derivative herein can further comprise a polyurethane (e.g., any as disclosed herein). Such a composition can comprise, for example, about 1, 5, 10, 15, 20, 35, 30, 35, 40, 45, 50, 55, 60, 5-60, 5-50, 5-45, 5-40, 5-35, 5-30, 10-60, 10-50, 10-45, 10-40, 10-35, or 10-30 wt % of the glucan ester derivative herein; the remainder can comprise all or mainly (e.g., more than 90% or 95%) one or more polyurethanes. Such a composition can be wet (e.g., a dispersion of a glucan ester derivative and a polyurethane) or dry (e.g., a masterbatch, film / coating, laminate, foam, or extruded composite of a glucan ester derivative and a polyurethane). The polyurethanes herein can have a molecular weight of, for example, about or at least about 1000, 1500, 2000, 2500, 3000, 3500, 4000, 1000-3000, 1500-3000, 1000-2500, or 1500-2500. In some examples, such compositions can be hydrolytically aged (e.g., exposed to 45° C.-55° C., or about 50° C., and / or 90%-98% or about 95% relative humidity for a period of 2-4 or 3 days). In some aspects, the polyurethane compositions with the glucan ester derivatives herein can be heat-processable and / or pressure-processable; for example, the application of heat and / or pressure for pressing, molding, extrusion, or any other related processing steps can be at about or at least about 90° C., 95° C., 100° C., 105° C., 110° C., 115° C., 120° C., 130° C., 140° C., 95° C.-115° C., or 100° C.-110° C., and / or at a pressure of at least about 5000, 10000, 15000, 20000, or 25000 psi. Such application of heat and / or pressure can be continued for a period of, for example, at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, or 30 minutes. In some aspects, the compressed polyurethane composition such as a film can be about or at least about 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99%, or 100% transparent or translucent. In some aspects, any polyurethane composition disclosed herein can be manufactured by a method comprising providing an aqueous polyurethane dispersion and mixing the polyurethane dispersion with the polyurethane dispersion. The resulting aqueous composition can be used directly to make a composition (e.g., a film or coating), or it can be dried into a masterbatch, which is then used to prepare a composition (e.g., by melt processing).

[0241] In some respects, film or coating can be in the form of edible film or coating. In some respects, such material can comprise the glucan ester derivative herein and one or more components described in U.S. Patent No. 4710228,4543370,4820533,4981707,5470581,5997918,8206765 or 8999413, or U.S. Patent Application Publication No. 2005 / 0214414, which are incorporated herein by reference. In some respects, the glucan ester derivative herein replaces starch and / or starch derivatives in edible film or coating, optionally as disclosed in any aforementioned reference. Edible films or coatings can be, for example, on potato products (e.g., potato chips such as French fries), other vegetables or vegetable products (e.g., zucchini, pumpkin, sweet potato, onion, okra, pepper, green beans, tomato, cucumber, lettuce, cabbage, carrot, broccoli, cauliflower, Brussels sprouts, bean sprouts, onions, any fresh-cut form of vegetables), mushrooms, fruits (e.g., berries (such as raspberries, strawberries, or blueberries), avocados, kiwis, kumquats, oranges, tangerines, apples, pears, bananas, grapefruits, cherries, papayas, lemons, limes, mangoes, peaches, cantaloupes, any fresh-cut form of fruits), and / or nuts (peanuts, walnuts, almonds, pecans, cashews, filberts / hazelnuts, Brazil nuts, macadamia nuts). Any other food disclosed herein (as appropriate) can have, for example, an edible coating. In some respects, these and other food products with edible films or coatings herein can be fried or baked, and / or the films or coatings provide tenderness, moisture retention, moisture resistance, crispness, dietary fiber (substitute digestible starch), oxygen barrier, freshness, and / or anti-ripening. In some respects, anti-ripening can be measured by coating reduction (e.g., at least 25%, 50%, 75%, 80%, 85%, or 90%) of the extent (e.g., at 15°C-30°C, 15°C-25°C, or 20°C-25°C) of the release of gaseous ripening hormones (such as ethylene) of plant-based products, and / or by coating reduction of the extent to which plant products are softened and / or sweetened. In some aspects, an edible coating can be prepared by applying an aqueous dispersion or solution comprising a glucan ester derivative herein (e.g., at 5-15, 5-12, 5-10, 7.5-15, 7.5-12, or 7.5-10 wt % in water) to a food product and drying the dispersion or solution (e.g., by air drying, forced air drying, vacuum drying, and / or heating).

[0242] In some aspects, the coating composition that can be used to prepare the coatings herein can include any of the aforementioned components / ingredients / formulations. In some aspects, the coating composition is a latex composition, such as described below.

[0243] In some aspects, the composition comprising at least one polyglucan ester derivative as disclosed herein can be a latex composition. Examples of latex compositions herein include coatings (e.g., primers, finishing agents / decorators), adhesives, films, coatings, and adhesives. The formula and / or components of the latex composition herein (except for the composition herein) can be as described in, for example, U.S. Patent Nos. 6,881,782, 3,440,199, 3,294,709, 5,312,863, 4,069,186, or 6,297,296, or U.S. Patent Application Publication No. 2020 / 0263026, all of which are incorporated herein by reference.

[0244] The glucan ester derivatives as disclosed herein can be present in the latex composition in any useful amount, such as about or at least about 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0.06%, 0.07%, 0.08%, 0.09%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 0.10%, 0.11%, 0.12%, 0.13%, 0.14%, 0.15%, 0.16%, 0.17%, 0.18%, 0.19%, 0.20%, 0.21%, 0.22%, 0.23%, 0.24%, 0.25%, 0.26%, 0.27%, 0.28%, 0.29%, 0.30%, 0.31%, 0.32%, 0.33%, 0.34%, 0.35%, 0.36%, 0.37%, 0.38%, 0.39%, 0.40%, 0.41%, 0.42%, 0.43%, 0.44%, 0.45%, 0.46%, 0.47%, 0.48%, 0.49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, %, 0.7%, 0.8%, 0.9%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 0.01%-75%, 0.01%-5%, 5%-20%, 20%-50%, or 50%-75%.

[0245] In some aspects, the latex composition may include a polymer polymerized from at least one ethylenically unsaturated monomer (e.g., a monoethylenically unsaturated monomer); a polyurethane; an epoxy resin, and / or a rubber elastomer. Examples of the monoethylenically unsaturated monomers herein include vinyl monomers, acrylic monomers, allyl monomers, acrylamide monomers, unsaturated monocarboxylic acids, and unsaturated dicarboxylic acids.

[0246] Examples of suitable vinyl monomers for the polymers in the latex compositions herein include any compound having vinyl functionality (i.e., ethylenic unsaturation), such as vinyl esters (e.g., vinyl acetate, vinyl propionate, vinyl laurate, vinyl pivalate, vinyl nonanoate, vinyl decanoate, vinyl neodecanoate, vinyl butyrate, vinyl benzoate, vinyl isopropyl acetate), vinyl aromatic hydrocarbons (e.g., styrene, methyl styrene and similar lower alkyl styrenes, chlorostyrene, vinyl toluene, vinyl naphthalene, divinyl benzene), vinyl The latex composition herein includes vinyl acetate-ethylene copolymers, carboxylated vinyl acetate-ethylene copolymers, and / or polyvinyl acetate.

[0247] Examples of suitable acrylic monomers for the polymers in the latex compositions herein include alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, aromatic derivatives of acrylic acid and methacrylic acid, acrylamide, and acrylonitrile. Typically, alkyl acrylates and methacrylic acid monomers (also referred to as alkyl esters of acrylic acid or methacrylic acid) have an alkyl ester portion containing from 1 to about 18 carbon atoms per molecule, or from 1 to about 8 carbon atoms per molecule. Suitable acrylic monomers include, for example, methyl acrylate and methyl methacrylate, ethyl acrylate and ethyl methacrylate, butyl acrylate and butyl methacrylate, propyl acrylate and propyl methacrylate, 2-ethylhexyl acrylate and 2-ethylhexyl methacrylate, cyclohexyl acrylate and cyclohexyl methacrylate, decyl acrylate and decyl methacrylate, isodecyl acrylate and isodecyl methacrylate, benzyl acrylate and benzyl methacrylate, isobornyl acrylate and isobornyl methacrylate, neopentyl acrylate and neopentyl methacrylate, and 1-adamantyl methacrylate. If acid functionality is desired, acids such as acrylic acid or methacrylic acid may also be used.

[0248] In some aspects, the latex composition includes a polyurethane polymer. Examples of suitable polyurethane polymers are those containing polysaccharides, as disclosed in U.S. Patent Application Publication No. 2019 / 0225737 (which is incorporated herein by reference). The latex containing polyurethane can be prepared, for example, as disclosed in U.S. Patent Application Publication No. 2016 / 0347978 (which is incorporated herein by reference), and / or contain the reaction product of one or more polyisocyanates and one or more polyols. Useful polyols include, for example, polycarbonate polyols, polyester polyols, and polyether polyols. The polycarbonate polyurethane herein can be formed as a reaction product of a polyol (such as 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, or tetraethylene glycol) with a diaryl carbonate (such as diphenyl carbonate or phosgene). At least one polyisocyanate herein can be an aliphatic polyisocyanate, an aromatic polyisocyanate, or a polyisocyanate having both an aromatic group and an aliphatic group. Examples of polyisocyanates include 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, a mixture of 2,4- and 2,6-toluene diisocyanates, bis(4-isocyanatocyclohexyl)methane, 1,3-bis(1-isocyanato-1-methylethyl)benzene, bis(4-isocyanatophenyl)methane, 2,4′-diphenylmethane diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4-diisocyanatotoluene, bis(3-isocyanatophenyl)methane, 1,4-diisocyanatobenzene, 1,3-diisocyanato-o-xylene, 1,3-diisocyanato- Also useful herein are polyisocyanate homopolymers containing, for example, allophanate, biuret, isocyanurate, iminooxadiazinedione, or carbodiimide groups.The polyol herein can be any polyol containing two or more hydroxyl groups, for example, C2 to C12 alkanediol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, isomers of butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 1,4-bis(hydroxymethyl)cyclohexane, 1,2,3-propanetriol (glycerol), 2- Hydroxymethyl-2-methyl-1,3-propanol (trimethylolethane), 2-ethyl-2-hydroxymethyl-1,3-propanediol (trimethylolpropane), 2,2-bis(hydroxymethyl)-1,3-propanediol (pentaerythritol); 1,4,6-octantriol; chloropentanediol; glycerol monoalkyl ether; glycerol monoethyl ether; diethylene glycol; 1,3,6-hexanetriol; 2-methylpropanediol; 2,2,4-trimethyl-1,3-pentanediol, cyclohexanedimethanol, polymer polyols, such as polyether polyols or polyester polyols. In some aspects, the polyols herein can be poly(oxytetramethylene) glycol, polyethylene glycol, or poly-1,3-propylene glycol. In some aspects, the polyols can be polyester polyols, such as polyester polyols produced by transesterification of aliphatic diacids with aliphatic diols. Suitable aliphatic diacids include, for example, C3 to C10 diacids, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid. In some aspects, aromatic and / or unsaturated diacids can be used to form polyester polyols.

[0249] In some aspects, the latex composition comprises an epoxy polymer / resin (polyepoxide), such as a bisphenol A epoxy resin, a bisphenol F epoxy resin, a novolac epoxy resin, an aliphatic epoxy resin, or a glycidylamine epoxy resin.

[0250] In some respects, latex composition includes rubber elastomer. In some respects, rubber elastomer can include one or more sulfur-vulcanizable elastomers based on diene with glass transition temperature (Tg) lower than -30 ℃ as determined by dynamic mechanical analysis, for example. In other examples, rubber elastomer herein includes natural rubber, synthetic polyisoprene, polybutadiene rubber, styrene / butadiene copolymer rubber, ethylene propylene diene monomer rubber, hydrogenated nitrile rubber, chloroprene rubber, styrene / isoprene / butadiene terpolymer rubber, butadiene / acrylonitrile rubber, polyisoprene rubber, isoprene / butadiene copolymer rubber, nitrile rubber, ethylene-acrylic rubber, butyl and halogenated butyl rubber, chlorosulfonated polyethylene, fluoroelastomer, hydrocarbon rubber, polybutadiene or silicone rubber.

[0251] The liquid component of the latex composition herein can be water or an aqueous solution. In some aspects, the aqueous solution of the latex can include an organic solvent that is miscible or immiscible with water. Suitable organic solvents herein include acetone, methyl ethyl ketone, butyl acetate, tetrahydrofuran, methanol, ethanol, isopropanol, diethyl ether, glycerol ether, hexane, toluene, dimethylacetamide, dimethylformamide, and dimethyl sulfoxide.

[0252] In some respects, the latex composition herein can further include one or more additives. The example of additive herein includes dispersant, rheological aid, defoamer, foaming agent, adhesion promoter, fire retardant, bactericide, fungicide, preservative, optical brightener, filler, anti-settling agent, coalescing agent, humectant, buffer, pigment / colorant (for example, metal oxide, synthetic organic pigment, carbon black), viscosity modifier, antifreeze agent, surfactant, adhesive, cross-linking agent, corrosion inhibitor, hardener, pH adjusting agent, salt, thickener, plasticizer, stabilizer, extender and matting agent. The example of pigment herein includes titanium dioxide (TiO ), calcium carbonate, diatomaceous earth, mica, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silicon dioxide, talcum, zinc oxide, aluminum silicate, nepheline syenite and its mixture. In some aspects, the latex composition is substantially free (e.g., less than 1, 0.5, 0.1, or 0.01 wt% of a component) of starch, starch derivatives (e.g., hydroxyalkyl starch), cellulose, and / or cellulose derivatives (e.g., carboxymethyl cellulose).

[0253] In some aspects, the latex composition in the form of a coating or other coloring agent herein can have a pigment volume concentration (PVC) of about 3% to about 80%. For example, a matte coating can have a PVC in the range of about 55%-80%, a primer or base coat can have a PVC in the range of about 30%-50%, and / or a glossy colored coating can have a PVC in the range of about 3%-20%. In some aspects, a coating or other coloring agent can have a PVC of about 55%, 60%, 65%, 70%, 75%, 80%, 55%-80%, 55%-75%, 55%-70%, 60%-80%, 60%-75%, 60%-70%, 63%-67%, 64%-66%, 65%-80%, 65%-75%, or 65%-70%. The PVC value herein can be, for example, the value of a specific pigment (or pigment mixture) such as those disclosed above (e.g., titanium dioxide). It is believed that the compositions of the present disclosure provide one or more physical properties to a latex composition (e.g., for use as a coating or other colorant): for example, opacity, less pigment required, increased hardness, reduced tack, reduced gloss (i.e., providing a matte effect), increased shear strength, better abrasion resistance, improved drying time, improved resistance to fading, less foaming, and / or improved feel (less tacky feel) compared to a latex composition that differs only in that it does not contain the disclosed composition.

[0254] The latex composition herein can be applied to the substrate (above) of the article using any method known in the art. Typically, after applying the latex composition, at least a portion of the aqueous solution is removed, for example by drying, to provide an adhesive, film, coating, or adhesive comprising the latex composition in dry or semi-dry form. Suitable application methods include air knife coating, rod coating, rod coating, wire rod coating, spray coating, brush coating, cast coating, flexible scraper coating, gravure coating, spray applicator coating, short-stay coating, slide hopper coating, curtain coating, flexographic coating, sizer coating, reverse roll coating, and transfer roll coating. For example, the latex composition can be applied to at least a portion of the substrate and can be applied with one or more covering layers / one or more times.

[0255] Some aspects herein relate to compositions comprising pigments. Compositions comprising pigments can be in the form of liquid (e.g., aqueous or non-aqueous compositions herein) or in the form of solid (e.g., dry compositions herein). Examples of compositions comprising pigments herein include any of such compositions disclosed elsewhere herein (e.g., coatings, primers, stains), inks, dyes (e.g., food coloring dyes, fabric coloring dyes), resins, sunscreens, and cosmetics (e.g., mascara, blush, nail polish / nail polish, lipstick, lip gloss, eyeliner, foundation, eye shadow, skin decoration compositions). The pigment in the composition comprising pigments can be, for example, any pigment herein. Examples of pigments useful in these and / or other aspects herein include oxides of titanium (e.g., titanium dioxide), zinc, iron, zirconium, cerium, and chromium; manganese violet; ultramarine blue; chromium hydrate; Prussian blue; zinc sulfide; nitroso, nitro, azo, xanthene, quinoline, anthraquinone, and / or phthalocyanine compounds; metal complex compounds; and isoindolinone, isoindolinone, quinacridone, peronone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, and / or quinophthalone compounds. Additional examples of pigments useful herein are those disclosed in U.S. Patent Application Publication No. 2006 / 0085924, which is incorporated herein by reference.

[0256] The composition comprising at least one glucan ester derivative as disclosed herein can be in the form of a composite material (e.g., a rubber composite material or a polyurethane composite material), such as disclosed in U.S. Patent Application Publication Nos. 2019 / 0225737, 2017 / 0362345, or 2020 / 0181370, all of which are incorporated herein by reference. Optionally, it can be said that in addition to the glucan ester derivative of the present disclosure, the composite material as disclosed herein also includes at least one polymer. One or more of the above components (e.g., rubber or polyurethane) of the latex composition can optionally be another polymer in such a composite material. The other polymer of the composite material herein can be rubber, polyurethane, thermoplastic polymer, polyethylene, polypropylene, ethylene copolymer, polyvinyl butyrate, polylactic acid, polyvinyl alcohol, polyamide, polyether thermoplastic elastomer, polyester, polyether ester, ethylene vinyl alcohol copolymer, starch, cellulose, or any suitable polymer as disclosed above for the latex component.

[0257] In some respects, rubber can be one or more of, for example, natural rubber, synthetic rubber, polyisoprene, polybutadiene, styrene-butadiene copolymer, styrene-isoprene copolymer, butadiene-isoprene copolymer, styrene-butadiene-isoprene terpolymer, ethylene propylene diene monomer rubber, hydrogenated nitrile rubber, silicone rubber, or chloroprene rubber. The example of the composite material comprising rubber herein includes tire (for example, automobile / bicycle; pneumatic tire; including tire tread and / or tire sidewall), belt (for example, conveyor belt, power transmission belt), hose, liner, footwear (for example, shoes, sports shoes, boots; sole, cushion, and / or aesthetic features), coating, film, and adhesive. The rubber composite material herein is typically vulcanized. In some aspects, it is expected that the inclusion of the composition herein in a composite material comprising rubber can provide advantages such as lower cost, lower density, lower energy consumption during processing, and / or better or equivalent performance (e.g., increased wet traction, reduced rolling resistance, lighter weight, and / or mechanical strength) compared to the use of existing fillers such as carbon black or silica; in some aspects, the tire can have such performance enhancements. In some aspects, the composition herein replaces about or at least about 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100 wt % of the existing filler (e.g., carbon black or silica) typically used in rubber composite materials (such as tires). It should be noted that rubber composite tires currently on the market (not including the composition herein) typically contain up to about 30 wt % of existing fillers such as carbon black. Thus, the rubber composite material herein, such as a tire, may contain, for example, about or at least about 5, 10, 15, 20, 25, or 30 wt % of a composition as disclosed herein. In some aspects, the rubber composition herein may have a low minimum elastic torque (M L ) (e.g., less than or about 0.10, 0.08, 0.06, 0.04, 0.03, or 0.02 dNm [deciNewton-meter]), and thus methods of mixing the rubber composition during its preparation are disclosed.

[0258] The composition comprising at least one glucan ester derivative as disclosed herein can be paper / packaging composition or cellulose fiber-containing composition.The example of such composition can be any type of paper / packaging or cellulose fiber-containing composition disclosed herein, such as paper (for example, writing paper, office paper, copy paper, kraft paper), cardboard, cardboard, corrugated board, tissue, napkin / tissue, wipes or nonwoven fabric.The paper / packaging composition herein or the formula of cellulose fiber-containing composition and / or component (except glucan ester derivative herein) and the form of these compositions can be as described below:For example, U.S. Patent Application Publication No. 2018 / 0119357, 2019 / 0330802, 2020 / 0062929, 2020 / 0308371 or 2020 / 0370216, all of which are incorporated herein by reference.In some aspects, glucan ester derivatives play the role of reinforcing aid in paper or other cellulose fiber-containing compositions. It is contemplated that the ability of the glucan ester derivatives to flocculate fibers and / or other insoluble materials in papermaking processes (e.g., pulp flocculation) is a means by which the glucan ester derivatives herein can be incorporated into paper or other products that involve flocculation in their production. However, in some aspects, the glucan ester derivatives can be added as a component to any of the foregoing compositions in a manner independent of possible addition as a flocculation aid.

[0259] Some aspects of the present disclosure relate to a flocculation or dehydration method comprising: (a) mixing at least one glucan ester derivative herein into an aqueous composition containing suspended solids / particles, whereby at least a portion of the suspended solids / particles become flocculated; and (b) optionally, separating the flocculated solids / particles of (a) from the aqueous composition. Thus, in some aspects, the glucan ester derivatives can be characterized as, for example, flocculants, dehydrating agents, clarifiers, and / or turbidity removers. The flocculated particles of the treated composition typically settle (flocculate) or at least become more amenable to separation procedures (e.g., filtration). Although soluble glucan ester derivatives can be used in the flocculation method, insoluble glucan ester derivatives can also be used in some aspects. Typically, the glucan ester derivatives used for flocculation applications herein are (i) biodegradable and / or (ii) uncrosslinked.

[0260] For example, one, two, three or more different types of glucan ester derivatives herein can be used in flocculation methods. In some respects, the glucan ester derivative is the only flocculant used, and in other respects, the glucan ester derivative is used together with another type of flocculant (for example, commercial existing flocculants such as acrylamide). In these latter aspects, the glucan ester derivative can constitute for example about or at least about 30,40,50,60,70,80 or 90wt% of all flocculants added to the aqueous composition.

[0261] The amount of the glucan ester derivative mixed into the aqueous composition comprising suspended solids / particles in step (a) can be, for example, about or at least about 2, 4, 6, 8, 10, 12, 14, 2-14, 2-12, 2-10, 2-8, 4-14, 4-12, 4-10, 4-8, 6-14, 6-12, 6-10, 6-8, 8-14, 8-12 or 8-10 g / kg (based on dry solids) suspended solids. It should be understood that after mixing step (a), typically the water-soluble glucan ester derivative is dissolved in the aqueous composition. Mixing can be carried out by any standard means.

[0262] The temperature and pH of the aqueous composition with suspended solids treated with the glucan ester derivative can be any temperature and pH as disclosed herein for the aqueous composition. In some aspects, the pH can be about 4, 5, 6, 7, 8, 9, 10, 4-10, 5-9, or 6-8, and / or the temperature can be about 1-80°C, 1-70°C, 1-60°C, 1-50°C, 1-40°C, 1-30°C, 5-80°C, 5-70°C, 5-60°C, 5-50°C, 5-40°C, 5-30°C, 15-80°C, 15-70°C, 15-60°C, 15-50°C, 15-40°C, or 15-30°C. After the glucan ester derivative is added and mixed with the aqueous composition, settling of the initially suspended solids can be allowed to continue, for example, for about or at least about 0.5, 1, 2, 3, 4, 5, 6, 9, 12, 18, 24, 30, 36, 42, or 48 hours.

[0263] In some respects, after processing with the glucan ester derivative, the percentage of initial suspended solid sedimentation (that is, no longer suspended) is about or at least about 30,40,50,60,70,80,90,95,96,97,98,99 or 100wt%.Typically, the flocculant herein allows the sedimentation particles to occupy less space.For example, after processing waterborne composition (initially having suspended particles) with the glucan ester derivative herein, the cumulative volume of the sedimentation particles can be about or less than about 90%, 80%, 70%, 60% or 50% of the cumulative volume of the precipitated particles that are deposited in the waterborne composition (wherein all other conditions of each system are the same) without the aid of flocculant.Any suitable method can be used to determine the sedimentation volume, such as the method described in the following examples.

[0264] In some aspects, when treated with the glucan ester derivatives herein, the turbidity (i.e., the quality of a liquid being cloudy, opaque, and / or thick due to suspended solids), color, and / or opacity of an aqueous composition with suspended solids / particles can be reduced by about or at least about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or 75%. Turbidity can be measured, for example, in nephelometric turbidity units (NTU). Any suitable method can be used to measure turbidity, such as in Progress in Filtration and Separation (Edition: 1, Chapter 16. Turbidity: a measure of filtrate and supernatant quality?, Publisher: Academic Press, Editor: EStarleton, July 2015) (which is incorporated herein by reference), or as described in the Examples below. The color of the liquid herein can be measured using any suitable method, such as, for example, spectrocolorimetry or photoelectric colorimetry.

[0265] In some aspects, when treated with the glucan ester derivatives herein, the filterability of the aqueous composition with suspended solids / particles can be enhanced / improved. The filterability of the liquid composition can be measured using any suitable method, such as by measuring the capillary pumping time. In some aspects, when treated with the glucan ester derivatives herein, the capillary pumping time (e.g., measured in seconds) of the aqueous composition with suspended solids / particles can be reduced by about or at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 85%. Any suitable method can be used to measure the capillary pumping time of the liquid.

[0266] Suspended particles that can be subjected to flocculation herein are typically colloidal particles (i.e., insoluble particles [solids] that are stably suspended). Therefore, an aqueous composition that can be subjected to the flocculation method herein can be, for example, a colloid. An aqueous composition containing suspended solids / particles that can be treated with a flocculant as disclosed herein can be, for example, wastewater (e.g., urban, industrial, agricultural wastewater), dirt / sewage, sludge (e.g., activated sludge), water from a water body (e.g., river / stream, canal, moat, pond, swamp, lake, sea), pond water, cooling water, water containing sediments (e.g., clay deposits) and / or soil, water to be processed for drinking, or water containing fibers and / or fillers (e.g., present in a papermaking process (e.g., pulp flocculation)). Examples of industrial wastewater come from paper mills or drilling / mining operations. In some aspects, suspended solids can include microbial cells (alive and / or dead), such as bacteria, yeast, and / or algae. It is contemplated that flocculation herein can be applied to aqueous compositions present in food or beverage manufacturing processes such as brewing (e.g., wort after fermentation thereof), cheese curd formation, or soy curd (tofu) production. Systems / operations that can incorporate the disclosed flocculation methods include, for example, wastewater / sludge treatment, papermaking, water purification, soil conditioning, and / or mining / drilling / downhole operations, or any other system / operation that uses flocculation.

[0267] The flocculation method herein optionally further comprises the step of separating the flocculated solids / particles from the treated aqueous composition. Such a step may include, for example, sedimentation / sedimentation, filtration, centrifugation, and / or decantation.

[0268] The present disclosure also relates to a method for producing a solid composition comprising at least one glucan ester derivative herein. Such a method may include at least (a) providing a non-caustic (e.g., pH 6-8 or 6-9) aqueous composition (e.g., solution or dispersion) comprising at least one glucan ester derivative as disclosed herein, (b) making the aqueous composition in a desired form (e.g., fiber, fibrid, film / coating, composite material, extrudate), and (c) removing liquid / solvent from the aqueous composition of step (b) to produce a solid composition comprising the glucan ester derivative. In some aspects, the ester derivative of the glucan as a non-derivative herein is insoluble under non-caustic aqueous conditions (e.g., α-1,3-glucan with DP>8 or>9).

[0269] In some aspects where the non-caustic aqueous composition is a solution and the ester derivatives of the glucan herein as non-derivatives are insoluble under non-caustic aqueous conditions, the liquid / solvent can be removed by raising the pH of the solution to above about 10, 10.5, 11, 11.5, or 12, thereby causing the dissolved glucan ester to precipitate out of the solution. The pH of the solution can be increased, for example, by adding / mixing a base (e.g., a metal hydroxide, such as NaOH) to the solution. The precipitated glucan ester derivative from step (b) - which is in the desired form / shape - can be optionally washed, for example with an organic liquid such as an alcohol (e.g., methanol, ethanol, isopropanol), and / or dried. The concentration of the glucan ester derivative in the solution provided in step (a) can be as disclosed elsewhere herein, such as about or at least about 10, 12, 14, 16, 18, 20, 25, 30, 10-30, 10-25, 10-20, 16-30, 16-25, or 16-20 wt %.

[0270] The present disclosure also relates to a solid composition as produced by the aforementioned method. Such a composition can be, for example, a fiber, a fibrid, a film / coating, a composite material, or an extrudate.

[0271] Non-limiting examples of the compositions and methods disclosed herein include:

[0272] 1. A composition comprising an ester derivative of a glucan (glucan ester derivative), wherein the glucan has a degree of substitution (DoS) of up to about 3.0 substituted with at least two organic groups individually ester-linked to the glucan, wherein (i) at least one of the organic groups is a cationic organic group, and (ii) at least one of the organic groups is a hydrophobic organic group.

[0273] 2. The composition of embodiment 1, wherein the glucan is α-glucan.

[0274] 3. The composition of embodiment 2, wherein at least about 50% of the glycosidic bonds of the alpha-glucan are alpha-1.3 bonds.

[0275] 4. The composition of embodiment 2, wherein at least about 50% of the glycosidic bonds of the α-glucan are α-1,6 bonds, optionally wherein the α-glucan comprises at least 1% α-1,2 and / or α-1,3 branches.

[0276] 5. The composition of embodiment 1, wherein the glucan is a β-glucan (eg, wherein at least about 50% of the glycosidic bonds of the β-glucan are β-1,3 bonds or β-1,4 bonds).

[0277] 6. The composition of embodiment 1, 2, 3, 4, or 5, wherein the dextran has a weight average degree of polymerization (DPw) of at least 6.

[0278] 7. The composition of embodiment 1, 2, 3, 4, 5, or 6, wherein the DoS of the at least two organic groups is at least about 0.005.

[0279] 8. The composition of embodiment 1, 2, 3, 4, 5, 6, or 7, wherein the DoS of the at least two organic groups is about 0.005 to about 1.5.

[0280] 9. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, or 8, wherein the DoS of the cationic organic groups is about 0.005 to about 1.5.

[0281] 10. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, or 9 wherein the DoS of the cationic organic groups is from about 0.005 to about 1.0.

[0282] 11. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 wherein the DoS of the cationic organic groups is from about 0.005 to about 0.5.

[0283] 12. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11 wherein the DoS of the cationic organic groups is from about 0.005 to about 0.1.

[0284] 13. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 wherein the DoS of the cationic organic groups is about 0.04 to about 0.1.

[0285] 14. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, wherein the DoS of the hydrophobic organic group is about 0.005 to about 1.5.

[0286] 15. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, wherein the DoS of the hydrophobic organic group is about 0.005 to about 1.0.

[0287] 16. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, wherein the DoS of the hydrophobic organic group is about 0.005 to about 0.5.

[0288] 17. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16, wherein the DoS of the hydrophobic organic group is about 0.4 to about 1.0.

[0289] 18. A composition as described in embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, wherein the cationic organic group comprises the following structure:

[0290] And R1, R2 and R3 are each independently a group containing at least one carbon atom (eg, R1, R2 and R3 are each CH3).

[0291] 19. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18, wherein the cationic organic group comprises the structure:

[0292] And R1, R2 and R3 are each independently a group containing at least one carbon atom (eg, R1, R2 and R3 are each CH3).

[0293] 20. A composition as described in embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19, wherein the hydrophobic organic group comprises C2 to C 26 Acyl (e.g., C6 to C 18 Acyl, C8 to C 16 Acyl, C 10 To C 14 Acyl, or C 12 acyl).

[0294] 21. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, wherein the hydrophobic organic group comprises an aromatic group (e.g., a benzoyl or substituted benzoyl group).

[0295] 22. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, or 21, wherein the ester derivative of glucan has a biodegradability of at least 10% after 15 days as determined by the Carbon Dioxide Evolution Test Method.

[0296] 23. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, wherein the composition is an aqueous composition.

[0297] 24. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, or 23, wherein the composition is a household care product, a personal care product, an industrial product, an ingestible product (e.g., a food product), or a pharmaceutical product.

[0298] 25. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 further comprising at least one surfactant.

[0299] 26. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 further comprising at least one enzyme.

[0300] 27. The composition of embodiment 26, wherein the enzyme is a cellulase, a protease, a lipase, an amylase, a lipase, or a nuclease.

[0301] 28. The composition of embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, or 27 further comprising at least one of a complexing agent, a soil release polymer, a surfactant enhancing polymer, a bleach, a bleach activator, a bleach catalyst, a fabric conditioner, a clay, a foam booster, a foam inhibitor, an anti-corrosion agent, a soil suspending agent, an anti-soil redeposition agent, a dye, a bactericide, a tarnish inhibitor, an optical brightener, a perfume, a saturated or unsaturated fatty acid, a dye transfer inhibitor, a chelating agent, a hueing dye, a visual signaling ingredient, a defoamer, a structurant, a thickener, an anti-caking agent, a starch, a sand, or a gelling agent.

[0302] 29. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28, wherein the composition is in the form of, or contained in, a liquid, a gel, a powder, a hydrocolloid, granules, a tablet, a bead or a lozenge, a single compartment sachet, a multi-compartment sachet, a single compartment pouch, or a multi-compartment pouch.

[0303] 30. A composition as described in embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, or 29, wherein the composition is: (a) a flocculant, (b) a viscosity modifier, (c) a latex composition, (d) a composition containing a pigment, (e) a film or coating, (f) a fiber or fibrid, (g) a cosmetic product (e.g., a hair styling product), (h) a detergent composition, (i) an adhesive composition, (j) paper, or (k) any composition / product disclosed herein.

[0304] 31. A method for producing an ester derivative of glucan (glucan ester derivative), the method comprising: (a) contacting glucan with at least two esterifying agents, wherein at least one of the esterifying agents comprises a cationic organic group, wherein at least one of the esterifying agents comprises a hydrophobic organic group (optionally wherein [i] the contacting is performed in one reaction and the at least two esterifying agents are provided simultaneously in the reaction, or the at least two esterifying agents are provided sequentially in the reaction, or [ii] the contacting is performed in at least two separate reactions, wherein at least one of the reactions uses at least one esterifying agent having a cationic group, and the at least two esterifying agents in the reactions are provided sequentially). at least one using at least one esterifying agent having a hydrophobic group), wherein at least one cationic organic group and at least one hydrophobic organic group are esterified to the glucan, thereby producing an ester derivative of the glucan (for example, according to embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22), wherein the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 substituted by the cationic organic group and the hydrophobic organic group, and (b) optionally, isolating the ester derivative of the glucan produced in step (a).

[0305] 32. A method of styling hair, the method comprising at least steps (a) and (b), or steps (c) and (d), as follows: (a) contacting (e.g., applying) the hair with a glucan ester derivative according to Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 (or a composition according to the above examples) to provide treated hair (or coated hair), and (b) placing the treated hair (or the coated hair) in a desired form (e.g., straightening, curling, or placing the hair in any other form different from the form the hair was in prior to step [a] or [b]) ); or (c) placing the hair in a desired form (e.g., straightening, curling, or placing the hair in any other form different from the form in which the hair existed before step [c]), and (d) contacting (e.g., coating) the hair of step (c) with a glucan ester derivative according to Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 (or a composition according to the above embodiments) to provide treated hair (or coated hair); and (e) optionally, removing the solvent (if present) used to deliver the glucan ester derivative to the hair in step (a) or (d).

[0306] 33. The composition of embodiments 1, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, or the method of embodiments 31 or 32, wherein "soy polysaccharide" is used instead of "glucan".

[0307] 34. A method of producing a solid composition comprising at least one glucan ester derivative (such as from Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22), wherein the method comprises at least (a) providing a non-caustic (e.g., pH 5.0) solution comprising at least one glucan ester derivative as disclosed herein; 6-8 or 6-9) an aqueous composition (e.g., a solution or dispersion), (b) placing the aqueous composition in a desired form (e.g., fibers, fibrids, films / coatings, composites, extrudates), and (c) removing the liquid / solvent of the aqueous composition of step (b) (e.g., by drying, and / or if a solution is used, by raising the pH of the solution to above about 10 to cause the dissolved glucan ester to precipitate out of solution) to produce a solid composition comprising the glucan ester derivative, and (d) optionally washing and / or drying the solid composition produced in step (c).

[0308] 35. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, or 33, or the method of embodiments 32 or 34, but wherein the cationic organic ester group is replaced with an anionic organic group, optionally wherein the anionic organic group is linked to the glucan ether (e.g., a carboxyalkyl such as a carboxymethyl) or an ester (e.g., a cyclic anhydride derivative group such as a succinate).

[0309] 36. The composition of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, or 33, or the method of embodiments 32 or 34, but wherein the hydrophobic organic ester group is replaced with an anionic organic group, optionally wherein the anionic organic group is linked to the glucan ether (e.g., a carboxyalkyl such as a carboxymethyl) or an ester (e.g., a cyclic anhydride derivative group such as a succinate).

[0310] Non-limiting examples of the compositions and methods disclosed herein include:

[0311] 1b. A composition comprising an ester derivative of dextran, wherein the dextran has a degree of substitution (DoS) of up to about 3.0 substituted with at least one cationic organic group (cationic acyl) attached to the dextran ester.

[0312] 2b. The composition of embodiment 1b, wherein the glucan is α-glucan.

[0313] 3b. The composition of embodiment 2b, wherein at least about 50% of the glycosidic bonds of the α-glucan are α-1.3 bonds.

[0314] 4b. The composition of embodiment 2b, wherein at least about 50% of the glycosidic bonds of the α-glucan are α-1,6 bonds, optionally wherein the α-glucan comprises at least 1% α-1,2 and / or α-1,3 branches.

[0315] 5b. The composition of embodiment 1b, wherein the glucan is β-glucan.

[0316] 6b. The composition of embodiment 5b, wherein at least about 50% of the glycosidic bonds of the β-glucan are β-1,3 bonds or β-1,4 bonds.

[0317] 7b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, or 6b, wherein the dextran has a weight average degree of polymerization (DPw) of at least 6.

[0318] 8b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, or 7b, wherein the DoS of the cationic organic groups is at least about 0.005.

[0319] 9b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, or 7b, wherein the DoS of the cationic organic groups is at least about 0.3.

[0320] 10b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, or 7b, wherein the DoS of the cationic organic groups is about 0.3 to about 2.0.

[0321] 11b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, or 10b, wherein the cationic organic group comprises the structure:

[0322] And R1, R2 and R3 are each independently a group containing at least one carbon atom.

[0323] 12b. The composition of embodiment 11b, wherein R1, R2 and R3 are each CH3.

[0324] 13b. The composition of embodiment 11b, wherein the cationic organic group comprises the following structure:

[0325] And R1, R2 and R3 are each independently a group containing at least one carbon atom.

[0326] 14b. The composition of embodiment 13b, wherein R1, R2 and R3 are each CH3.

[0327] 15b. A composition as described in embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, or 14b, wherein the ester derivative of glucan has a biodegradability of at least 10% after 15 days as determined by the carbon dioxide evolution test method.

[0328] 16b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, or 15b, wherein the composition is an aqueous composition.

[0329] 17b. A composition as described in embodiments 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, or 16b, wherein the composition is a household care product, a personal care product, an industrial product, an ingestible product (e.g., a food product), or a pharmaceutical product.

[0330] 18b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, or 17b further comprising at least one surfactant.

[0331] 19b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, or 18b further comprising at least one enzyme.

[0332] 20b. The composition of embodiment 19b, wherein the enzyme is a cellulase, a protease, a lipase, an amylase, a lipase, or a nuclease.

[0333] 21b. A composition as described in embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, or 20b, further comprising at least one of the following: a complexing agent, a soil release polymer, a surfactant enhancing polymer, a bleach, a bleach activator, a bleach catalyst, a fabric conditioner, a clay, a foam booster, a foam inhibitor, an anti-corrosion agent, a soil suspension agent, an anti-soil redeposition agent, a dye, a bactericide, a tarnish inhibitor, an optical brightener, a perfume, a saturated or unsaturated fatty acid, a dye transfer inhibitor, a chelating agent, a hueing dye, a visual signal conductive component, a defoamer, a structurant, a thickener, an anti-caking agent, a starch, a sand, or a gelling agent.

[0334] 22b. The composition of embodiments 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, 20b, or 21b, wherein the composition is in the form of, or contained in, a liquid, a gel, a powder, a hydrocolloid, granules, a tablet, a bead or a lozenge, a single compartment sachet, a multi-compartment sachet, a single compartment pouch, or a multi-compartment pouch.

[0335] 23b. A composition as described in Examples 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, 20b, 21b, or 22b, wherein the composition is: (a) a flocculant, (b) a viscosity modifier, (c) a latex composition, (d) a composition containing a pigment, (e) a film or coating, (f) a fiber or fibrid, (g) a cosmetic product (e.g., a hair styling product), (h) a detergent composition, (i) an adhesive composition, (j) paper, or (k) any composition / product disclosed herein.

[0336] 24b. A method for producing an ester derivative of glucan, the method comprising: (a) contacting glucan with at least one esterifying agent comprising a cationic organic group (cationic acyl) in a reaction, wherein at least one cationic organic group (cationic acyl) is esterified to the glucan to produce an ester derivative of the glucan (for example, according to embodiments 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, or 15b), wherein the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 substituted with the cationic organic group (cationic acyl), and (b) optionally, isolating the ester derivative of glucan produced in step (a).

[0337] 25b. A composition as described in Examples 1b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, 20b, 21b, 22b, or 23b, or a method as described in Example 24b, but wherein "soy polysaccharide" is used instead of "glucan".

[0338] 26b. A method for producing a solid composition comprising at least one glucan ester derivative (such as from Examples 1b, 2b, 3b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, or 15b), wherein the method comprises at least (a) providing a non-caustic (e.g., pH 6-8 or 6-9) aqueous composition (e.g., solution or dispersion) comprising at least one glucan ester derivative as disclosed herein, (b) placing the aqueous composition in a desired form (e.g., fibers, fibrids, films / coatings, composites, extrudates), and (c) removing the liquid / solvent of the aqueous composition of step (b) (e.g., by drying, and / or if a solution is used, by raising the pH of the solution to above about 10 to cause the dissolved glucan ester to precipitate out of solution) to produce a solid composition comprising the glucan ester derivative, and (d) optionally washing and / or drying the solid composition produced in step (c).

[0339] 27b. A method of styling hair, the method comprising at least steps (a) and (b), or steps (c) and (d), as follows: (a) contacting (e.g., applying) the hair with a glucan ester derivative according to embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, 20b, 21b, 22b, or 23b (or a composition according to the above embodiments) to provide treated hair (or coated hair), and (b) placing the treated hair (or the coated hair) in a desired form (e.g., straightened, curled, or in any other form different from the form in which the hair existed prior to step [a] or [b]). or (c) placing the hair in a desired form (e.g., straightened, curled, or in any other form different from the form in which the hair existed prior to step [c]), and (d) contacting (e.g., applying) the hair of step (c) with a glucan ester derivative according to embodiment 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, 10b, 11b, 12b, 13b, 14b, 15b, 16b, 17b, 18b, 19b, 20b, 21b, 22b, or 23b (or a composition according to the above embodiments), thereby providing treated hair (or coated hair); and (e) optionally, removing the solvent (if present) used to deliver the glucan ester derivative to the hair in step (a) or (d).

[0340] Examples

[0341] The present disclosure is further illustrated in the following examples. It should be understood that although these examples indicate certain aspects of the present invention, they are given by way of illustration only. From the above discussion and these examples, those skilled in the art can determine the essential characteristics of the disclosed embodiments, and various changes and modifications can be made to adapt the disclosed embodiments to a variety of uses and conditions without departing from the spirit and scope of the disclosed embodiments.

[0342] Materials / Methods

[0343] Representative preparation of α-1,3-glucan

[0344] α-1,3-glucan having about 100% α-1,3 glycosidic bonds can be synthesized, for example, according to the procedures disclosed in US Application Publication No. 2014 / 0179913 (see, e.g., Example 12 therein), which is incorporated herein by reference.

[0345] As another example, a slurry of α-1,3-glucan was prepared from an aqueous solution (0.5 L) containing Streptococcus salivarius gtfJ enzyme (100 units / L) as described in U.S. Patent Application Publication No. 2013 / 0244288 (incorporated herein by reference), sucrose (100 g / L) (EM8550) obtained from OmniPur Sucrose, Inc., potassium phosphate buffer (10 mM) obtained from Sigma Aldrich, and DMEM obtained from DuPont adjusted to pH 5.5. (antimicrobial agent) (100 ppm). The resulting enzyme reactant was maintained at 20°C-25°C for 24 hours. Since the α-1,3-glucan synthesized in the reaction is water-insoluble, a slurry is formed. The α-1,3-glucan solids were then collected on a 40 micron filter paper using a Buchner funnel equipped with a 325 mesh screen to form a wet cake containing about 60 wt%-80 wt% water.

[0346] Representative preparation of α-1,6-glucan with α-1,2 branches

[0347] Methods for preparing α-1,6-glucans containing different amounts of α-1,2 branches are disclosed in U.S. Application Publication No. 2018 / 0282385, which is incorporated herein by reference. Reaction parameters such as sucrose concentration, temperature, and pH can be adjusted to provide α-1,6-glucans with various levels of α-1,2-branching and molecular weight. A representative procedure for preparing α-1,2-branched α-1,6-glucans (containing 19% α-1,2-branching and 81% α-1,6 bonds) is provided below. Using 1D 1 H-NMR spectra were used to quantify the glycosidic bond distribution. Additional samples of α-1,6-glucan with α-1,2-branching were similarly prepared. For example, one sample contained 32% α-1,2-branching and 68% α-1,6 bonds, and another contained 10% α-1,2-branching and 90% α-1,6 bonds.

[0348] According to the following procedure, a stepwise combination of glucosyltransferase (dextransucrase) GTF8117 and α-1,2 branching enzyme GTFJ18T1 is used to prepare soluble α-1,6-glucan with about 19% α-1,2 branches. The reaction mixture (2L) consisting of sucrose (450g / L), GTF8117 (9.4U / mL) and 50mM sodium acetate is adjusted to pH 5.5 and stirred at 47°C. An aliquot (0.2-1mL) is taken out at a predetermined time and quenched by heating at 90°C for 15 minutes. The resulting heat-treated aliquot is passed through a 0.45-μm filter. The flow-through is analyzed by HPLC to determine the concentration of sucrose, glucose, fructose, leucrose, oligosaccharides and polysaccharides. After 23.5 hours, the reaction mixture is heated to 90°C for 30 minutes. An aliquot of the heat-treated reaction mixture was passed through a 0.45-μm filter and the flow-through was analyzed for soluble mono / disaccharides, oligosaccharides, and polysaccharides. The major product was a linear dextran with a DPw of 93.

[0349] The second reaction mixture is prepared by adding 238.2g of sucrose and 210mL of α-1,2-branching enzyme GTFJ18T1 (5.0U / mL) to the remaining heat-treated reaction mixture obtained by the GTF8117 reaction just described above. The mixture is stirred at 30°C with a volume of about 2.2L. An aliquot (0.2-1mL) is taken out at a predetermined time and quenched by heating at 90°C for 15 minutes. The resulting heat-treated aliquot is passed through a 0.45-μm filter. The flow-through is analyzed by HPLC to determine the concentration of sucrose, glucose, fructose, leucrose, oligosaccharides and polysaccharides. After 95 hours, the reaction mixture is heated to 90°C for 30 minutes. The heat-treated reaction mixture of the aliquot is passed through a 0.45-μm filter, and the soluble monosaccharides / disaccharides, oligosaccharides and polysaccharides of the flow-through are analyzed. The remaining heat-treated mixture is centrifuged using a 1-L centrifuge bottle. The supernatant was collected and cleaned more than 200 times using an ultrafiltration system with a 1- or 5-kDa MWCO cartridge and deionized water. The cleaned oligosaccharide / polysaccharide product solution was dried. The dried sample was then analyzed by 1H-NMR spectroscopy to determine the anomeric bonds of the oligosaccharides and polysaccharides.

[0350] Example 1

[0351] Synthesis of Insoluble Betaine Ester Derivatives of α-Glucan

[0352] This example illustrates the use of insoluble alpha-1,3-glucan to produce various forms of betaine alpha-1,3-glucan derivatives, which are soluble cationic glucan esters.

[0353] Water-insoluble α-1,3-glucan (80 g [493.6 mmol]) (approximately 100% α-1,3 bonds) was suspended in 2.4 L of N,N-dimethylacetamide. The temperature of the formulation was then raised to 120°C and stirred at that temperature for two hours. After cooling to 80°C, 144 g of LiCl was added to the formulation. After the formulation was cooled to 70°C, a clear solution was formed. Ground betaine hydrochloride (45.6 g [296.16 mmol], CAS Reg. No. 590-46-5) (e.g., Sigma Aldrich Catalog No. B3501) was added to the solution, which was then stirred at 70°C for 10 minutes. Then, 57.6 g (296.16 mmol) of tosyl chloride (dehydrating agent) was added to the solution, and the formulation was allowed to react at 70°C for 2 hours. A clear yellow solution was formed, which was then cooled to room temperature. The solid product was precipitated by adding 4 L of ethanol to 1 / 3 of the solution; this was done in portions, after which all the precipitated products were combined (a similar precipitated product can be obtained by adding 12 L of ethanol to the entire solution in a larger container). The precipitated product betaine α-1,3-glucan ester was washed three times with 5 L of ethanol each time, and then dried at 40° C. under vacuum.

[0354] α-1,3-glucan samples with different molecular weights (about 100% α-1,3-linkages, all water-insoluble) were reacted individually as described above, but using different reagent amounts to produce betaine-modified α-1,3-glucan ester products of different molecular weights and degree of substitution (DoS) levels. Table 1 shows the various betaine α-1,3-glucan ester products (Samples AF) that were successfully synthesized, all of which were readily soluble in neutral water at room temperature.

[0355] Table 1

[0356] Various water-soluble betaine α-1,3-glucan ester products

[0357]

[0358]

[0359] Example 2

[0360] Synthesis of Soluble Betaine Ester Derivatives of α-Glucan

[0361] This example illustrates the use of soluble glucan α-1,2-branched α-1,6-glucan to produce various forms of betaine α-1,6-glucan derivatives, which are soluble cationic glucan esters.

[0362] Various soluble α-1,2-branched α-1,6-glucans were used for betaine esterification: 40 kDa α-1,6-glucan with 20% α-1,2 branches, 17 kDa α-1,6-glucan with 45% α-1,2 branches, and 300 kDa α-1,6-glucan with 45% α-1,2 branches. In each of these α-glucans, the α-1,6-glucan backbone (with α-1,2 branches therein) has 100% α-1,6 glycosidic bonds; the molecular weights listed are those of the α-1,6-glucan backbone. Each α-1,2-branch consists of a single (side chain) glucose unit.

[0363] For betaine esterification, each (40 g) of the above branched α-1,6-glucan was dissolved separately in DMAc (200 mL) at elevated temperature (110°C-130°C). Betaine hydrochloride (40 g, CAS Reg. No. 590-46-5) (e.g., Sigma Aldrich Catalog No. B3501) and dicyandiamide (>20 g, dehydrating agent) were then added to start esterification. The uniformity of each reaction preparation was further adjusted by adding DI-water and / or CaCl. Each reaction was then heated under vacuum for less than 3 hours. Approximately 80 mL of liquid was removed and the crude product was precipitated from methanol and washed several times in methanol to obtain the desired product (betaine-modified α-glucan ester) in quantitative yield. The products from these reactions were designated BC-2 (40 kDa α-1,6-glucan, 20% α-1,2 branches, DoS 0.02), BC-4 (40 kDa α-1,6-glucan, 20% α-1,2 branches, DoS 0.04), BC-10 (17 kDa α-1,6-glucan, 45% α-1,2 branches, DoS 0.04) and BC-11 (300 kDa α-1,6-glucan, 45% α-1,2 branches, DoS 0.04).

[0364] Example 3

[0365] Analysis of Betaine α-1,3-Glucan Ester Derivatives

[0366] Aqueous solutions of the betaine α-1,3-glucan ester products of Table 1 were prepared and analyzed for viscosity using a Brookfield unit (spindle S03) at room temperature (about 20° C.). High molecular weight glucan esters exhibit high viscosity levels at relatively low concentrations (see Table 2, e.g., Product E), which is a desirable feature in many applications such as industrial applications (e.g., oil and gas production, wastewater treatment), personal care, and home care. In contrast, glucan ester products having low molecular weights allow the preparation of high solid aqueous solutions (about 15 wt % or more) (see Table 2), which is a desirable feature in coating applications (e.g., paper coatings); for example, higher solids content minimizes the required drying time and improves overall process yield.

[0367] Table 2

[0368] Viscosity Analysis of Aqueous Solutions of Betaine α-1,3-Glucan Ester Products

[0369]

[0370]

[0371] aSee Table 1.

[0372] b Concentration of dextran ester product dissolved in water.

[0373] The effect of pH on the dissolution behavior of betaine-modified alpha-1,3-glucan in water was tested. A 20 wt% solution (about 1 mL) of sample A (see Table 1) in water was added to 20 mL of water containing 4000, 400, 40, or 4 ppm of NaOH (water pH was 13, 12, 11, or 10, respectively). At pH 13 and 12, the glucan esters settled to the bottom as hard polymers (pH 13) or precipitated out of the solution as turbid solutions (pH 12). At pH 11, more glucan esters remained in solution (some turbidity), while at pH 10, most (if not all) of the glucan esters remained in solution. This dissolution behavior of betaine-modified alpha-1,3-glucan esters was unexpected. While quaternary ammonium α-1,3-glucan ethers (e.g., hydroxypropyltrimethylammonium glucan ether) become more soluble at high pH, ​​the opposite is true for betaine α-1,3-glucan esters. This behavior provides several advantages for using betaine α-1,3-glucan esters in polymer processing. For example, the glucan esters can be extruded from water into a high pH bath into fibers or films. Then, if desired, the ester chemistry can be removed (chemically or enzymatically) to produce a completely water-insoluble α-1,3-glucan product. Therefore, betaine-modified α-1,3-glucan esters allow for the maintenance of a water-based processing environment to produce products containing non-derivatized α-1,3-glucan.

[0374] Biodegradability determination

[0375] Biodegradability is determined according to the OECD 301B Ready Biodegradability CO2 Emission Test Guide (see OECD, 1992. Organization for Economic Co-operation and Development, OECD 301 Ready Biodegradability. OECD Chemical Testing Guide, Part 3 - incorporated herein by reference). In this assay, the test substance (betaine glucan ester) is the only source of carbon and energy, and under aerobic conditions, the microorganisms metabolize the test substance to produce CO2 or incorporate carbon into the biomass. The amount of CO2 produced by the test substance (corrected for CO2 escaped by the blank inoculum) is expressed as a percentage of the theoretical amount of CO2 (ThCO2) that can be produced if the organic carbon in the test substance is completely converted to CO2.

[0376] The biodegradation testing of betaine α-1,3-glucan ester derivatives was carried out according to the OECD 301B test (above). The biodegradation of the glucan ester sample with the highest betaine group DoS (sample F, Table 1) was analyzed over 28 days and the results are shown in Figure 1 and Table 3.

[0377] Table 3

[0378] Biodegradation of Betaine α-1,3-Glucan Ester Products

[0379]

[0380] aAbbreviations: TOC (total organic carbon content), AVG (average value), SD (standard deviation), REL (relative to reference)

[0381] Sample F showed significant biodegradability within 28 days of the initial test ( Figure 1 , Table 3). This result is unexpected because the DoS of sample F (0.88) is relatively high in terms of biodegradability: such DoS levels with different linkage / derivatization types (e.g., ether-linked carboxymethyl or ether-linked hydroxypropyltrimethylammonium groups) would typically greatly inhibit biodegradability. The enhanced biodegradability characteristics of the betaine α-1,3-glucan ester derivatives herein make them very capable of use in applications where bioaccumulation of polymers is undesirable (e.g., aquatic environments).

[0382] Example 4

[0383] Use of Betaine-Modified Glucan Esters in Beauty Care - Hair Styling Applications

[0384] In this example, betaine α-1,3-glucan esters and betaine α-1,2-branched α-1,6-glucan esters were tested for characteristics related to hair styling applications. The various cationic glucan esters listed in Table 4 were tested for these applications along with a negative control (no glucan derivative) and a positive control (cationic glucan ether).

[0385] Table 4

[0386]

[0387]

[0388] a Change in hair tress height after styling with 1:1 ethanol / water and 1 wt% dextran derivative samples. Little or no change reflects effective hair styling (i.e., application of the dextran derivative maintains the bend in the tress). Refer to the text below.

[0389] Each test sample was completely dissolved in an ethanol / water (1:1) mixture at 1 wt%. The turbidity of the solution was then measured in nephelometric turbidity units (NTU) using a calibrated turbidometer (HACH 2100AN turbidimeter). The solution was then poured into a petri dish and allowed to evaporate overnight at room temperature. The quality of each resulting film was checked. For several of the tested betaine-modified glucan ester samples (see Table 4), good solubility and high quality film formation were observed as indicated by low solution turbidity and the ability to form a clear film, respectively. These features are believed to make the material useful in hair styling products - for example, can allow a clear and transparent application on the hair to provide hair styling retention while avoiding an unclean appearance.

[0390] In the curl retention test, approximately 1 gram of each solution (Table 4) was applied to a tress (8" RINBOOOL hair swatch). The resulting tresses were dried overnight at room temperature with half of the tress curled back at an angle of >90 degrees. Each tress was then hung in a 45°C oven and heated for 3 hours. The height of the curled half of each tress was then measured and compared to the height of the tress that existed before it was hung (Table 4). In the control experiment, the height of the curled half of the tress changed by 6.5 cm. However, for several tresses treated with the betaine-modified glucan ester samples, the height of the curled half of the tress did not change, or changed very little (see Table 4), indicating significant hair style retention.

[0391] Example 5

[0392] Use of betaine-modified dextran esters in coatings

[0393] In this example, betaine alpha-1,3-glucan esters were used to coat paper. The coating provided an oil / grease barrier to the paper.

[0394] Betaine alpha-1,3-glucan ester (Sample A, Table 1) was applied to a paper substrate as a solution prepared by dissolving betaine alpha-1,3-glucan powder in distilled water at 10 wt% or 20 wt%. For example, to prepare 50 grams of a 10 wt% formulation, 5 grams of betaine glucan powder was dissolved in 45 grams of water. Each formulation was stirred at room temperature using a magnetic stirring bar until all the powder was dissolved. Alternatively, a laboratory blender could be used if desired. The viscosity of each solution increased as the betaine glucan was dissolved in water.

[0395] Once the betaine alpha-1,3-glucan powder is completely dissolved, the resulting solution is applied to a folding boxboard substrate (METSABOARD CLASSIC FBB, 235 gsm grammage, 0.425 mm thickness) using an automatic rod coater with a heating module (model PROCEQ ZAA 2600.A, Zehntner Testing Instruments). Different rods (Zehntner) are used to provide the desired coating thickness and grammage to the paper substrate: #3 rod (Art. No. ACC378.006, 6.9 μm wet thickness) and #14 rod (Art. No. ACC378.032, 32.0 μm wet thickness). The coating speed is set to 20 mm / min and the coating is applied at room temperature. The coated paper is dried overnight under ambient conditions. Lower drying times will also be possible, and drying can optionally be carried out in an oven at, for example, 60°C for 10 minutes. In one test, the procedure was applied to the pre-treated side of the containerboard (pre-treated by the manufacturer for printing), while the procedure was applied to the back side (non-printing side) of a separate sheet of containerboard that was tested in an otherwise duplicated manner.

[0396] The oil barrier properties of each betaine alpha-1,3-glucan coated paper substrate were evaluated using the 60 second Cobb Unger Oil Test (ISO 535, TAPPI T441, SCAN P 12, EN 20535, DIN 53132, incorporated herein by reference). The results of this analysis are shown in Table 5. As compared to the negative control reference (uncoated paper), the paper coated with betaine alpha-1,3-glucan ester using 10 wt% and 20 wt% solutions exhibited significant oil barrier functionality (Table 5).

[0397] Table 5

[0398]

[0399] gsm, grams per square meter.

[0400] Example 6

[0401] A two-step method for the synthesis of amphiphilic glucan ester derivatives containing cationic and hydrophobic substituents

[0402] This example illustrates a two-step process using water-soluble glucan α-1,2-branched α-1,6-glucan to produce multifunctional amphiphilic α-glucan ester derivatives. In particular, α-glucan derivatives substituted with betaine, benzoyl, lauroyl and acetyl were produced.

[0403] Step 1 1. Synthesis of hydrophobic glucan ester derivatives containing benzoyl and lauroyl substituents:

[0404] At 90°C, dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 30 g) was dissolved in DMAc (150 mL). The reaction preparation was distilled at 100°C under vacuum for one hour, removing about 60 mL of liquid. Benzoyl chloride (17 g) and lauroyl chloride (8 g) were then added, after which the reaction preparation was stirred at 90°C for 1.5 hours. The resulting product, benzoyl lauroyl α-1,2-branched α-1,6-glucan ester, was precipitated and purified using ethyl acetate and obtained in quantitative yield.

[0405] Step 1 2. Synthesis of amphiphilic glucan ester derivatives containing betaine, benzoyl and lauroyl substituents:

[0406] At elevated temperature (110°C), the hydrophobic α-glucan ester product (20 g) prepared in step 1 above is dissolved in DMAc (100 mL). Betaine hydrochloride (20 g, CAS Registry Number 590-46-5) (e.g., SigmaAldrich Catalog Number B3501), dicyandiamide (20 g) and water (3 mL) are then added. The reaction preparation is distilled under vacuum at 130°C for one hour, removing 40 mL of liquid. The reaction is then cooled to room temperature, after which the crude product is first precipitated in acetonitrile and then dissolved in water. The resulting aqueous solution is then subjected to ultrafiltration (MWCO 5kDa) followed by freeze drying to obtain 5.6 grams of the product benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan ester. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.07, 0.52, 0.23, and 0.13 for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively.

[0407] Example 7

[0408] A two-step method for the synthesis of amphiphilic glucan ester derivatives containing betaine and hydrophobic substituents

[0409] Step 1 1. Synthesis of hydrophobic glucan ester derivatives containing benzoyl and acetyl substituents:

[0410] At 88°C, dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 200 g) was dissolved in DMAc (1000 mL). The reaction preparation was distilled at 100°C under vacuum for one hour, removing 300 mL of liquid. Benzoyl chloride (110 g) was then added, after which the reaction preparation was stirred at 88°C for 2 hours. The resulting product, benzoyl α-1,2-branched α-1,6-glucan ester, was precipitated and purified using isopropanol and obtained in quantitative yield. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.36 and 0.14 for benzoyl and acetyl groups (acetyl groups were derived from DMAc solvent), respectively.

[0411] Step 1 2. Synthesis of amphiphilic glucan ester derivatives containing betaine, benzoyl and acetyl substituents:

[0412] The hydrophobic α-glucan ester product (10 g) prepared in step 1 above was dissolved in DMAc (300 mL) at elevated temperature (90° C.). Next, betaine hydrochloride (6 g) was added. The reaction preparation was distilled at 100° C. under vacuum for one hour, removing 30 mL of liquid. Tosyl chloride (12 g) was then added. The final reaction preparation was heated at 75° C. for one hour and then cooled to room temperature, after which the desired product was precipitated in isopropanol and washed three times with isopropanol to provide benzoyl acetyl betaine α-1,2-branched α-1,6-glucan ester. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.27, 0.34 and 0.14 for betaine, benzoyl and acetyl (acetyl derived from DMAc solvent), respectively. The molecular weight of the final product was determined by SEC to be 10.5 kDa.

[0413] Example 8

[0414] For the synthesis of amphiphilic glucan esters containing betaine, benzoyl, lauroyl and acetyl substituents Two-step method for derivatives

[0415] Step 1 1. Synthesis of hydrophobic glucan ester derivatives containing benzoyl, lauroyl and acetyl substituents:

[0416] The dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 120 g) was swollen in DMAc (550 mL) at 90°C for one hour. The reaction preparation was distilled under vacuum at 100°C for one hour, removing 185 mL of liquid. Benzoyl chloride (74 g) and lauroyl chloride (30 grams) were then added, after which the reaction preparation was stirred at 90°C for one hour and 45 minutes. The resulting product, benzoyl lauroyl acetyl α-1,2-branched α-1,6-glucan ester, was precipitated and purified using isopropanol and obtained in quantitative yield. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.64, 0.12, and 0.08 for benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively.

[0417] Step 1 2. Synthesis of amphiphilic glucan ester derivatives containing betaine, benzoyl, lauroyl and acetyl substituents:

[0418] The hydrophobic α-glucan ester product (10 g) prepared in step-1 above was dissolved in DMAc (300 mL) at an elevated temperature (90°C). Next, betaine hydrochloride (6 g) was added. The reaction preparation was distilled at 100°C under vacuum for one hour, removing 30 mL of liquid. Tosyl chloride (12 g) was then added. The final reaction preparation was heated at 75°C for one hour and then cooled to room temperature, after which the desired product was precipitated in isopropanol and washed three times to obtain benzoyl lauroyl acetyl betaine α-1,2-branched α-1,6-glucan ester in quantitative yield. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.13, 0.34, 0.03 and 0.01 for betaine, benzoyl, lauroyl and acetyl (acetyl derived from DMAc solvent), respectively. The molecular weight of the final product was determined by SEC to be 11.4 kDa.

[0419] Example 9

[0420] For the synthesis of amphiphilic glucan esters containing betaine, benzoyl, lauroyl and acetyl substituents Two-step method for derivatives

[0421] Step 1 1. Synthesis of hydrophobic glucan ester derivatives containing benzoyl, lauroyl and acetyl substituents:

[0422] The dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 120 g) was swollen in DMAc (560 mL) at 90°C for one hour. The reaction preparation was distilled under vacuum at 100°C for one hour, removing 240 mL of liquid. Benzoyl chloride (74 g) and lauroyl chloride (30 g) were then added, after which the reaction preparation was stirred at 90°C for 1.5 hours. The resulting product, benzoyl lauroyl acetyl α-1,2-branched α-1,6-glucan ester, was precipitated and purified using isopropanol and obtained in quantitative yield. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.57, 0.04, and 0.10 for benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively.

[0423] Step 1 2. Synthesis of amphiphilic glucan ester derivatives containing betaine, benzoyl, lauroyl and acetyl substituents:

[0424] At elevated temperature (90°C), the hydrophobic α-glucan ester product (10 g) prepared in step 1 above was dissolved in DMAc (300 mL). CaCl2.2H2O (12 g) was then added. Next, betaine hydrochloride (6 g) was added. The reaction preparation was distilled at 100°C under vacuum for one hour, removing 30 mL of liquid. Tosyl chloride (12 g) was then added. The final reaction preparation was heated at 75°C for one hour and then cooled to room temperature, after which the desired product was precipitated in isopropanol and washed three times to obtain benzoyl lauroyl acetyl betaine α-1,2-branched α-1,6-glucan ester in quantitative yield. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.28, 0.39, 0.02, and 0.12 for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively. The molecular weight of the final product was determined by SEC to be 8.1 kDa.

[0425] Example 10

[0426] One-pot synthesis of amphiphilic dextran ester derivatives containing cationic and hydrophobic substituents This example shows a one-pot (single-step) method using water-soluble glucan α-1,2-branched α-1,6-glucan to produce multifunctional amphiphilic α-glucan ester derivatives. In particular, α-glucan derivatives substituted with betaine, benzoyl, lauroyl and acetyl were produced.

[0427] At elevated temperature (90°C), dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 40 g) was dissolved in DMAc (200 mL). CaCl2.2H2O (12 g) was then added. Next, betaine hydrochloride (40 g) and toluenesulfonyl chloride (25 g) were added. The reaction preparation was distilled under vacuum at 100°C for one hour, removing 60 mL of liquid. Benzoyl chloride (15 g) and lauroyl chloride (10 g) were then added to the reaction. The final reaction preparation was heated for one hour and then cooled to room temperature, after which approximately 200 mL of ethanol was added. The soluble portion of the preparation was diluted with water and purified by ultrafiltration (MWCO 5 kDa), and then freeze-dried to give 10.8 g of the product benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan ester. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.07, 0.27, 0.16, and 0.08 for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively.

[0428] Example 11

[0429] One-pot synthesis of amphiphilic glucan ester derivatives containing betaine and hydrophobic substituents

[0430] This example shows a one-pot (single-step) method using water-soluble glucan α-1,2-branched α-1,6-glucan to produce multifunctional amphiphilic α-glucan ester derivatives. In particular, α-glucan derivatives substituted with betaine, benzoyl, lauroyl and acetyl were produced.

[0431] The dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 20 g, pre-dried overnight at 45°C) was swollen in DMAc (350 mL) at elevated temperature (90°C) for one hour. After this step, betaine hydrochloride (6 g) was added. The reaction preparation was distilled under vacuum at 100°C for one hour, removing 30 mL of liquid. Benzoyl chloride (7 g) and lauroyl chloride (5 g) were then added. The resulting reaction preparation was heated for one hour. Tosyl chloride (25 g) was then added. The final reaction preparation was stirred at 75°C for another hour and then cooled to room temperature. Isopropanol was added to precipitate the crude product. The solid product was further washed several times with isopropanol and then dried under vacuum to obtain 17.6 g of the product benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan ester. In particular, by 1H-NMR analysis determined that the product had acyl DoS values ​​of 0.15, 0.05, 0.01 and 0.07 for betaine, benzoyl, lauroyl and acetyl (acetyl derived from DMAc solvent), respectively. The molecular weight of the final product was determined by SEC to be 53.9 kDa.

[0432] Example 12

[0433] Amphiphilic glucan ester derivatives containing betaine, benzoyl, lauroyl and acetyl substituents One-pot synthesis

[0434] This example shows a one-pot (single-step) method using water-soluble glucan α-1,2-branched α-1,6-glucan to produce multifunctional amphiphilic α-glucan ester derivatives. In particular, α-glucan derivatives substituted with betaine, benzoyl, lauroyl and acetyl were produced.

[0435] The dextran powder (40 kDa α-1,6-glucan with 20% α-1,2 branches, 20 g, pre-dried overnight at 45°C) was swollen in DMAc (350 mL) at elevated temperature (90°C) for one hour. After this step, betaine hydrochloride (6 g) was added. The reaction preparation was distilled under vacuum at 100°C for one hour, removing about 30 mL of liquid. Benzoyl chloride (10 g) and lauroyl chloride (6.5 g) were then added. The resulting reaction preparation was heated for one hour. Tosyl chloride (12 g) was then added. The final reaction preparation was stirred at 75°C for another hour and then cooled to room temperature. Isopropanol was added to precipitate the crude product. The solid product was further washed several times with isopropanol and then dried under vacuum to obtain about 18 g of the product benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan ester. In particular, by 1 H-NMR analysis determined that the product had acyl DoS values ​​of 0.20, 0.09, 0.22, and 0.19 for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from DMAc solvent), respectively. The molecular weight of the final product was determined by SEC to be 10.4 kDa.

[0436] Example 13

[0437] Use of amphiphilic ester derivatives in beauty care - hair styling applications

[0438] In this example, amphiphilic α-1,2-branched α-1,6-glucan esters were tested for their characteristics related to hair styling applications. In particular, two different amphiphilic glucan esters produced above in Examples 6 and 10 (both benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan) and a negative control (no glucan derivative used) were tested for these applications.

[0439] Each glucan ester test sample was completely dissolved in an ethanol / water (3:1) mixture at 4 wt%. The turbidity of the solution was then measured in nephelometric turbidity units (NTU) using a calibrated turbidity meter (HACH 2100AN turbidimeter). The turbidity measurements for each sample are listed in Table 6.

[0440] In the curl retention test, about 0.5 grams of each solution was applied to a tress (8" RINBOOOL hair swatch). The resulting tress was dried overnight at room temperature with half of the tress curled back at an angle of >90 degrees. The height of the curled half of each tress was then measured and compared to the height of the tress as it existed before drying. In the control experiment, the height of the curled half of the tress changed by 6.0 cm. In comparison, for the tresses treated with the amphiphilic glucan ester derivatives produced in Examples 6 (Step 2 product) or 10 (one-pot product), the height of the curled half of each tress changed much less (Table 6), indicating significant hair style retention.

[0441] Table 6

[0442]

[0443] a Change in hair tress height after styling with 3:1 ethanol / water with 4 wt% glucan ester derivative sample. Little or no change reflects effective hair styling (i.e. application of the glucan derivative maintains the bend of the tress). See above.

Claims

1. A composition comprising an ester derivative of a dextran, wherein the dextran has a degree of substitution (DoS) of up to about 3.0 substituted with at least two organic groups attached to the dextran alone, wherein (i) at least one of the organic groups is a cationic organic group, and (ii) At least one of the organic groups is a hydrophobic organic group.

2. The composition according to claim 1, wherein The glucan is α-glucan.

3. The composition according to claim 2, wherein At least about 50% of the glycosidic bonds of the α-glucan are α-1,3 bonds.

4. The composition according to claim 2, wherein At least about 50% of the glycosidic bonds of the alpha-glucan are alpha-1,6 bonds, optionally wherein the alpha-glucan comprises at least 1% alpha-1,2 and / or alpha-1,3 branches.

5. The composition according to claim 1, wherein The dextran has a weight average degree of polymerization (DPw) of at least 6.

6. The composition according to claim 1, wherein The DoS of the at least two organic groups is about 0.005 to about 1.

5.

7. The composition of claim 1, wherein The DoS of the cationic organic group is about 0.005 to about 1.

5.

8. The composition of claim 1, wherein The DoS of the hydrophobic organic group is about 0.005 to about 1.

5.

9. The composition of claim 1, wherein The cationic organic group comprises the following structure: And R1, R2 and R3 are each independently a group containing at least one carbon atom.

10. The composition according to claim 9, wherein The cationic organic group comprises the following structure: And R1, R2 and R3 are each independently a group containing at least one carbon atom.

11. The composition according to claim 1, wherein The hydrophobic organic group comprises C2 to C 26 Acyl.

12. The composition of claim 1, wherein The hydrophobic organic group includes an aromatic group.

13. The composition of claim 1, wherein The ester derivative of dextran has a biodegradability of at least 10% after 15 days as determined by the Carbon Dioxide Evolution Test Method.

14. The composition of claim 1, wherein The composition is an aqueous composition.

15. The composition of claim 1, wherein The composition is a household care product, a personal care product, an industrial product, an ingestible product, or a pharmaceutical product.

16. The composition of claim 1, further comprising at least one surfactant.

17. A method for producing an ester derivative of glucan, the method comprising: (a) contacting glucan with at least two esterification agents, wherein at least one of the esterifying agents comprises a cationic organic group, wherein at least one of the esterifying agents comprises a hydrophobic organic group, wherein at least one cationic organic group and at least one hydrophobic organic group are esterified to said dextran, thereby producing an ester derivative of said dextran, wherein the ester derivative of dextran has a degree of substitution (DoS) of up to about 3.0 substituted with the cationic organic group and the hydrophobic organic group, and (b) optionally, isolating the ester derivative of glucan produced in step (a).

18. A method of styling hair, the method comprising at least steps (a) and (b), or steps (c) and (d), as follows: (a) contacting hair with the glucan ester derivative according to claim 1 to provide treated hair, and (b) bringing the treated hair (or the coated hair) into a desired form; or (c) placing the hair in a desired form, and (d) contacting the hair of step (c) with the glucan ester derivative of claim 1, thereby providing treated hair; and (e) optionally, removing the solvent, if any, used to deliver the glucan ester derivative to the hair in step (a) or (d).

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