Amphiphilic glucan ester derivative

Abstract

Compositions comprising an ester derivative of glucan are disclosed herein, wherein the glucan has a degree of substitution (DoS) of up to about 3.0 with at least two organic groups individually ester-linked to the glucan, (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. Methods for preparing these compositions, as well as various uses thereof, are further disclosed.

Description

Technical Field

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

[0002] The present disclosure is included in the field of polysaccharide derivatives. For example, the present disclosure relates to amphiphilic glucan ester derivatives and their use in various applications.

Background Art

[0003] Motivated by the desire to find novel-structured polysaccharides using enzymatic synthesis or microbial genetic engineering, researchers have found oligosaccharides and polysaccharides that are biodegradable and can be economically manufactured from renewable resource raw materials. Further research has shown that such polysaccharides can be chemically modified (derivatized) to have further utility in fields such as personal care, household care, industrial care, pharmaceuticals, and food. For example, ethers and esters of α-glucans containing α-1,3 glycosidic linkages have been disclosed to have various uses (e.g., U.S. Patent Application Publication Nos. 2016 / 0304629, 2016 / 0311935, 2017 / 0204232, 2014 / 0187767, 2020 / 0308371). Various derivatives of α-glucans containing α-1,6 glycosidic linkages, and uses therefor 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 having the desired utility have an inadequate biodegradability profile due to having a high level of derivatization. Some glucans with low levels of derivatization exhibit better biodegradability, but such products often cannot deliver optimal or even sufficient activity. Accordingly, there remains a need for product components that are not only renewable and biodegradable, but also provide performance equal to or better than that of products containing synthetic components. Amphiphilic glucan ester derivatives (and other compounds) are disclosed herein to address this need.

Summary of the Invention

Means for Solving the Problems

[0005] In one embodiment, the present disclosure relates 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 with at least two organic groups individually ester - bonded to the glucan, (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 a glucan. Such a method comprises: (a) contacting a glucan with at least two esterifying agents, wherein at least one of the esterifying agents contains a cationic organic group, at least one of the esterifying agents contains a hydrophobic organic group, and 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, and the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 with 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): (a) contacting the hair with a glucan ester derivative of the present specification, thereby providing treated hair; and (b) shaping the treated hair into a desired form; or (c) shaping the hair into a desired form; and (d) contacting the hair of step (c) with a glucan ester derivative of the present specification, thereby providing treated hair; and (e) optionally, removing the solvent (if present) used to deliver the glucan ester derivative to the hair in step (a) or (d).

Brief Description of the Drawings

[0008]

Figure 1

Mode for Carrying Out the Invention

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

[0010] Unless otherwise disclosed, the terms "a" and "an" as used herein are intended to encompass one or more (i.e., at least one) of the recited features.

[0011] When present, unless otherwise specified, all ranges are inclusive and combinable. For example, if a range of "from 1 to 5" (i.e., 1 - 5) is recited, the recited range should be construed to include ranges such as "1 - 4", "1 - 3", "1 - 2", "1 - 2 and 4 - 5", "1 - 3 and 5", etc. Numerical values of various ranges in this disclosure are described as approximations as if both the minimum and maximum values within the recited range begin with the word "about", unless otherwise explicitly stated. In this form, minor variations above and below the stated range can typically be used to achieve substantially the same result as the values within the range. Also, the disclosure of these ranges is intended to cover a continuous range including each value and every value between the minimum and maximum values.

[0012] It is intended that the upper limit of all numerical values given throughout this specification includes the limits of all lower numerical values as if such lower numerical limits were explicitly recited in this specification. The lower limit of all numerical values given throughout this specification would include the limits of all higher numerical values as if such higher numerical limits were explicitly recited in this specification. All numerical ranges given throughout this specification would include all narrower numerical ranges that fall within such broader numerical ranges as if such narrower numerical ranges were all explicitly recited in this specification.

[0013] It should be understood that, for clarity, the specific features of this disclosure described above and below in connection with an aspect / embodiment may be provided either individually or in combination in a single element. Conversely, for brevity, the various features of this disclosure described in connection with a single aspect / embodiment may be provided separately or in any sub-combination.

[0014] The term "polysaccharide" (or "glycan") refers to a polymeric carbohydrate molecule composed of long chains of monosaccharide units linked to each other by glycosidic bonds and that yields the constituent monosaccharides and / or oligosaccharides of the polysaccharide upon hydrolysis. The polysaccharides herein can be linear or branched and / or can be homopolysaccharides (composed of only one type of monosaccharide as a constituent element) or heteropolysaccharides (composed of two or more different types of monosaccharides as constituent elements). Examples of polysaccharides herein include glucans (polyglycose) and soybean polysaccharides.

[0015] "Glucan" herein is a type of polysaccharide that is a polymer of glucose (polyglycose). Glucan can be composed of, for example, about, or at least about 90 wt%, 91 wt%, 92 wt%, 93 wt%, 94 wt%, 95 wt%, 96 wt%, 97 wt%, 98 wt%, 99 wt%, or 100 wt% glucose monomer units. Examples of glucans herein are α-glucan and β-glucan.

[0016] The terms "α-glucan", "α-glucan polymer", etc. are used interchangeably herein. An α-glucan is a polymer containing glucose monomer units linked together by α-glycosidic bonds. In a typical embodiment, the glycosidic bonds of the α-glucan 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", etc. are used interchangeably herein. β-glucan is a polymer comprising glucose monomer units linked to each other by β-glycosidic bonds. In a typical embodiment, the glycosidic bonds of the beta-glucan 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% beta-glycosidic bonds. Examples of β-glucan polymers herein include β-1,3-glucan, β-1,4-glucan, and β-1,6-glucan.

[0018] The terms "sugar" and other similar terms herein refer to monosaccharides and / or disaccharides / oligosaccharides unless otherwise specified. As used herein, "disaccharide" refers to a carbohydrate in which two monosaccharides are linked by a glycosidic bond. As used herein, "oligosaccharide" refers to a carbohydrate in which, for example, 3 to 15 monosaccharides are linked by a glycosidic bond. Oligosaccharides can also be referred to as "oligomers". The monosaccharides (e.g., glucose and / or fructose) contained within the disaccharide / oligosaccharide can be referred to as "monomer units", "monosaccharide units", or other similar terms.

[0019] The terms "α-1,3-glucan", "polyα-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 joined together by glycosidic bonds, with at least about 50% of the glycosidic bonds being α-1,3. In some embodiments, the α-1,3-glucan comprises about or at least about 90%, 95% or 100% α-1,3 glycosidic bonds. Where present, most or all of the other bonds in the α-1,3-glucan herein are typically α-1,6, although some bonds can also be α-1,2 and / or α-1,4. The α-1,3-glucan herein is typically water-insoluble.

[0020] As used herein, terms such as "α-1,6-glucan", "polyα-1,6-glucan", "α-1,6-glucan polymer", "dextran" refer to water-soluble α-glucans containing glucose monomer units linked together by glycosidic bonds, with at least about 50% of the glycosidic bonds being α-1,6. In some embodiments, the α-1,6-glucan contains 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", "polyα-1,4-glucan", "α-1,4-glucan polymer", etc. are used interchangeably herein. An α-1,4-glucan is an α-glucan containing glucose monomer units linked together by glycosidic bonds, with at least about 50% of the glycosidic bonds being α-1,4. In some embodiments, the α-1,4-glucan contains about or at least about 90%, 95% or 100% α-1,4 glycosidic bonds. Most or all of the other bonds (if any) of 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. Here, examples of α-1,4-glucans include amylose, amylopectin, and starch.

[0022] The terms "β-1,4-glucan", "polyβ-1,4-glucan", "β-1,4-glucan polymer", "cellulose", etc. are used interchangeably herein. A β-1,4-glucan is a water-insoluble β-glucan containing glucose monomer units linked together by glycosidic bonds, with about 100% of the glycosidic bonds being β-1,4. The β-1,4-glucan can be, for example, as disclosed 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", etc. are used interchangeably herein. β-1,3-glucan is a β-glucan containing glucose monomer units linked together by glycosidic bonds, with at least about 50% of the glycosidic bonds being β-1,3. In some embodiments, the β-1,3-glucan contains about or at least about 90%, 95% or 100% β-1,3 glycosidic bonds. Most or all of the other bonds (if any) of the β-1,3-glucan herein are typically β-1,6 (typically forming branches). β-1,3-glucan can be, for example, as disclosed in U.S. Patent Application Publication No. 2014 / 0287919 and Stone, B.A. (2009, Chemistry of Beta-Glucans, In Antony Bacic et al., Eds., Chemistry, Biochemistry, and Biology of 1-3 Beta Glucans and Related Polysaccharides, Academic Press, Burlington, MA), which are incorporated herein by reference.

[0024] The terms "soybean polysaccharide" and "soybean 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 components of soybeans. The soybean polysaccharides herein can be, for example, as disclosed in U.S. Patent Application Publication No. 2018 / 0079832, which is incorporated herein by reference.

[0025] The "α-1,2 branch" (and similar terms) referred to herein typically includes glucose α-1,2-linked to the dextran backbone; thus, the α-1,2 branch herein can also be referred to as an α-1,2,6 bond. The α-1,2 branch herein typically has one glucose group (which may be called a pendant glucose).

[0026] As used herein, "α-1,3 branching" (and similar terms) typically includes glucose that is α-1,3-linked to a dextran backbone; thus, α-1,3 branching as used herein can also be referred to as an α-1,3,6 linkage. α-1,3 branching as used herein typically has one glucose group (which can also be referred to as a pendant glucose in some cases).

[0027] As used herein, "α-1,4 branching" (and similar terms) typically includes glucose that is α-1,4-linked to a dextran backbone; thus, α-1,4 branching as used herein can also be referred to as an α-1,4,6 linkage. α-1,4 branching as used herein typically has one glucose group (which can also be referred to as a pendant glucose in some cases).

[0028] The percent of branching in a polysaccharide as used herein refers to the percent of all linkages in the polysaccharide that represent a branch point. For example, the proportion of α-1,3 branching in the α-glucan of the present specification refers to the proportion of all linkages in the glucan that represent an α-1,3 branch point. Unless otherwise specified, the percentages of linkages disclosed herein are based on all linkages of the polysaccharide, or the portion of the polysaccharide that the disclosure specifically contemplates.

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

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

[0031] As used herein, the term "molar substitution" (M.S.) refers to the moles of organic groups per monomer unit of the polysaccharide derivative herein. It should be noted that the molar substitution value of a polysaccharide derivative can have a very high upper limit, for example, hundreds or even thousands.

[0032] The "molecular weight" of a polysaccharide or polysaccharide derivative herein can be expressed as the weight-average molecular weight (Mw) or the number-average molecular weight (Mn), and its unit is Dalton (Da) or gram / mole. Alternatively, the molecular weight can also 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 may optionally be provided as "DP" (degree of polymerization), which simply refers to the number of monomers contained within the polysaccharide. "DP" can also characterize the molecular weight of a polymer on an individual molecule basis. Various techniques for calculating these various molecular weight measurements are known in the art, such as by high-performance liquid chromatography (HPLC), size-exclusion chromatography (SEC), or gel permeation chromatography (GPC).

[0033] As used herein, Mw = ΣNiMi 2It can be calculated as / ΣNiMi (where Mi is the molecular weight of each chain i and Ni is the number of chains having that molecular weight). Besides SEC, the Mw of the 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. The Mn used herein can be calculated as Mn = ΣNiMi / ΣNi (where Mi is the molecular weight of chain i and Ni is the number of chains having that molecular weight). Besides SEC, the Mn of the polymer can be determined by various colligative property methods, such as end-group quantification by methods of measuring vapor pressure osmometry, proton NMR, proton FTIR, or spectroscopic analysis methods such as UV-Vis. The DPw and DPn used herein can be calculated from Mw and Mn by dividing them by the molar mass M1 of one monomer unit, respectively. In the case of an unsubstituted glucan polymer, M1 = 162. In the case of a substituted (derivatized) glucan polymer, M1 = 162 + M f ×DoS, where M f is the molar mass of the substituent and DoS is the degree of substitution (average number of substituents per glucose unit of the glucan polymer).

[0034] The "polysaccharide derivative" (and similar terms) (e.g., glucan derivative, e.g., α- or β-glucan derivative) in this specification typically refers to a polysaccharide substituted with at least one type of organic group (e.g., the acyl group in this specification). The degree of substitution (DoS) of the polysaccharide derivative in this specification can be up to about 3.0 (e.g., about 0.001 to about 3.0). The organic group in this specification that is an acyl group is bonded to the polysaccharide derivative via an ester bond. The precursor of the polysaccharide derivative in this specification typically refers to the non-derivatized polysaccharide used to produce the derivative (which can also be referred to as the polysaccharide portion of the derivative). The organic group in this specification that is an acyl group can be positively charged (cationic) or hydrophobic, and generally, the cationic charge can be as it exists when the organic group is in the aqueous composition of this specification, taking into account the pH of the aqueous composition (in some embodiments, the pH can be 4 to 10 or 5 to 9, or any pH disclosed in this specification).

[0035] The term "degree of substitution" (DoS, or DS) as used in this specification refers to the average number of hydroxyl groups substituted with one or more types of organic groups in each monomer unit of the polysaccharide derivative. The DoS of the polysaccharide derivative in this specification can be described with reference to the DoS of a specific substituent or the overall DoS that is the sum of the DoS values of different substituent types (e.g., in the case of a mixed ester). Unless otherwise disclosed, when the DoS is not described with reference to a specific substituent type, the overall DoS is meant.

[0036] Terms such as "glucan ester derivative", "glucan ester compound", and "glucan ester" are used interchangeably herein. The glucan ester derivatives herein are typically glucans 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 derivatives have a DoS with all of these organic groups up to about 3.0. Such glucan esters can optionally be characterized herein as amphiphilic glucan esters by having one or more different hydrophilic organic groups (especially one or more cationic organic groups) and one or more different hydrophobic organic groups. Glucan ester derivatives are referred to herein as "esters" by including the substructure -C G -O-CO-C-, where in the formula, "-C G -" represents a carbon atom of a monomer unit (e.g., glucose) of the glucan ester derivative (such a carbon atom was bonded to the hydroxyl group [-OH] in the polysaccharide precursor of the ester), and "-CO-C-" is contained in the acyl group.

[0037] The term "hydrophobic" herein can characterize a substituent organic group (substituent acyl group) that is nonpolar, 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, especially water, or other polar groups. Hydrophilic groups tend to attract water. Here, a cationic organic group (cationic acyl group) is an example of a hydrophilic organic group.

[0039] In some embodiments, terms such as "esterification reaction" and "esterification reaction composition" refer to a reaction that includes at least the glucan of the present disclosure, two or more esterifying agents, and typically a solvent. The hydroxyl groups of the glucose monomer units of the glucan are esterified 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 obtaining an amphiphilic glucan ester compound / derivative by placing the reaction under suitable conditions (e.g., solvent, time, temperature).

[0040] As used herein, the terms "aqueous liquid", "aqueous fluid", "aqueous condition", "aqueous setting", "aqueous system", etc. can refer to water or an aqueous solution. The "aqueous solution" herein may contain one or more dissolved salts, and the maximum total salt concentration can be about 3.5 wt% in some embodiments. The aqueous liquid herein typically contains water as the only solvent in the liquid, but the aqueous liquid can optionally contain one or more other solvents (e.g., polar organic solvents) miscible with water. Thus, an aqueous solution can contain a solvent having at least about 10 wt% water.

[0041] The "aqueous composition" herein has a liquid component containing, for example, 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 system" refers to a heterogeneous system having a dispersed phase and a dispersion medium, i.e., microscopically dispersed insoluble particles suspended throughout another substance (e.g., an aqueous composition such as water or an aqueous solution). An example of a colloidal dispersion system in this specification is a hydrophilic colloid. The terms "dispersant (dispersant and dispersion agent)" are used interchangeably herein and refer to a substance that promotes the formation and / or stabilization of a dispersion system. As used herein, "dispersing" refers to the act of preparing a dispersion system 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 embodiments, the latex is an emulsion containing dispersed particles. An "emulsion" in this specification is a dispersion of minute droplets of one liquid in another liquid in which the droplets are insoluble or immiscible (e.g., a nonpolar substance such as oil or an alkane in a polar liquid such as water or an aqueous solution).

[0043] The glucan ester derivatives in some embodiments of the present disclosure can provide stability to a dispersion or an emulsion. The "stability" of a dispersion or an emulsion (or the quality of "being stable") is, in this specification, for example, the ability of the dispersed particles of a dispersion or the liquid droplets (emulsion) dispersed in another liquid to remain dispersed for a period of about or at least about 0.5, 1, 2, 4, 6, 9, 12, 18, 24, 30 or 36 months after the initial preparation of the dispersion or the emulsion (e.g., about or at least about 70, 75, 80, 85, 90, 95, 96, 97, 98, 99 or 100% by weight of the particles of the dispersion or the liquid droplets of the emulsion are in a dispersed state). A stable dispersion or emulsion can resist overall creaming, precipitation, aggregation and / or association of the dispersed / emulsified material.

[0044] As used herein, the glucan ester derivatives of the present specification that are "soluble", "water-soluble", "aqueous-soluble" (and similar terms) dissolve (or significantly dissolve) in water or other aqueous conditions. Optionally, the aqueous conditions are further characterized by having a pH of 4 to 9 (e.g., pH 6 to 8) and / or a temperature of about 1 to 130 °C (e.g., 20 to 25 °C). In contrast, the glucan ester derivatives such as "insoluble", "water-insoluble", "aqueous-insoluble", etc. in the present specification do not dissolve under these conditions. In some embodiments, less than 1.0 gram (e.g., no detectable amount) of the water-insoluble glucan ester derivative dissolves in 1000 milliliters of such aqueous conditions (e.g., water at 23 °C).

[0045] The term "viscosity" as used herein refers to a measure of the degree to which a fluid (aqueous or non-aqueous) resists the force that causes flow. Examples of various units of viscosity that can be used herein include, for example, centipoise (cP, cps) and Pascal seconds (Pa·s). 1 centipoise is 1 / 100 poise, and 1 poise is 0.100 kg·m -1 ·s -1is equal to. Viscosity can, in some embodiments, be reported as "intrinsic viscosity" (IV, η, units dL / g), which term refers to a measure of the contribution of the glucan polymer to the viscosity of a liquid (e.g., a solution) containing the glucan polymer. In the present invention, IV measurements can be obtained using any suitable method as disclosed, for example, in U.S. Patent Application Publication No. 2017 / 0002335, U.S. Patent Application Publication No. 2017 / 0002336, or U.S. Patent Application Publication No. 2018 / 0340199, or Weaver et al. (J. Appl. Polym. Sci. 35:1631-1637), or Chun and Park (Macromol. Chem. Phys. 195:701-711), all of which are incorporated herein by reference. For example, by dissolving the glucan polymer in DMSO containing about 0.9 to 2.5 wt% (e.g., 1, 2, 1-2 wt%) LiCl (optionally, dissolved at about 100 °C for at least 2, 4, or 8 hours), the IV can be measured in part. The IV herein can, in some cases, 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. A polar organic solvent can dissolve in water or an aqueous solution. Thus, a polar organic solvent does not separate into a different phase when added to water or an aqueous solution. A polar organic solvent contains carbon and at least one heteroatom such as oxygen, nitrogen, sulfur, or phosphorus (i.e., a non-carbon or non-hydrogen atom). This is in contrast to a non-polar organic solvent that generally contains only carbon atoms and hydrogen atoms. A polar organic solvent typically has a dielectric constant greater than about 4. A polar organic solvent contains dipoles due to polar bonds.

[0047] The term "aprotic polar organic solvent" (and similar terms) as used herein refers to a polar organic solvent that does not have a suitably labile hydrogen atom capable of forming a hydrogen bond. An aprotic polar organic solvent does not contain a hydrogen atom bonded to an electronegative atom, e.g., an O-H, N-H, or S-H bond is absent.

[0048] As used herein, the term "protic polar organic solvent" (and similar terms) refers to a polar organic solvent having one or more suitably labile hydrogen atoms capable of forming hydrogen bonds. Protic polar organic solvents generally contain hydrogen atoms bonded to atoms having electronegative character, for example, one or more O-H, N-H, and / or S-H bonds are present.

[0049] The terms "household care products" and similar terms typically refer to products, goods, and services related to the treatment, cleaning, maintenance, and / or conditioning of household goods and their contents. Examples of the foregoing include, for example, chemicals, compositions, products, or combinations thereof having use in such care.

[0050] The terms "fabric", "cloth", "textile", and similar terms are used interchangeably herein and mean a woven fabric having a network of natural and / or man-made fibers. Such fibers can be in the form of, for example, spun or knitted yarns.

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

[0052] The "detergent compositions" herein typically contain at least one surfactant (detergent compound) and / or one builder. The "surfactant" herein means a substance that tends to lower the surface tension of a liquid in which the substance is dissolved. Surfactants can function, for example, as detergents, wetting agents, emulsifiers, foaming agents, and / or dispersants.

[0053] The terms "heavy-duty detergent", "all-purpose detergent", etc. are used interchangeably herein and mean a detergent useful for standard laundering of white and colored textile products at any temperature. The terms "light-duty detergent", "fine-fiber detergent", etc. are used interchangeably herein and mean a detergent useful for the care of delicate fabrics such as, for example, viscose, wool, silk, microfiber or other fibers requiring special care. "Special care" can include conditions such as using an excessive amount of water, low agitation, and / or no bleaching.

[0054] The terms "fabric softener", "fabric conditioner", etc. as used herein refer to a composition, such as in liquid or solid form, that deposits a lubricant and / or other surface-modifying components onto the fabric to help maintain the softness of the fabric and / or provide other beneficial characteristics to the fabric (such as lubricity, antistatic, anti-adhesion, and / or wrinkle prevention). Here, the fabric softener is typically applied to the fabric while usually rinsing the fabric after washing the fabric with a laundry detergent.

[0055] The term "personal care product" and similar terms typically refer to products, goods, and services related to the treatment, purification, washing, care, or conditioning of humans. Examples of the foregoing include, for example, chemicals, compositions, products, or combinations thereof having uses for such care.

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

[0057] The terms "ingestible product" and "ingestible composition", etc. refer to any substance that can be ingested orally (i.e., by mouth), either alone or together with other substances, regardless of whether consumption is intended. Thus, ingestible products include food / beverage products. "Food / beverage products" refer to any edible product intended for consumption (e.g., for nutritional purposes) by humans or animals, such as solids, semi-solids, or liquids. For example, the "food" in this specification can optionally refer to "foodstuffs", "food products" or other similar terms. "Non-edible products" ("non-edible compositions") refer to any composition that can be ingested orally for purposes other than the consumption of food or beverages. Examples of non-edible products in this specification include supplements, nutraceuticals, functional foods, pharmaceuticals, oral care products (e.g., toothpaste, mouthwash), and cosmetics (e.g., sweet lip cream). The "pharmaceuticals", "medicines", "drugs", "medications" or similar terms in this specification refer to compositions used for treating diseases or injuries and can be administered enterally or parenterally.

[0058] The terms "medical supplies" and similar terms typically mean products, goods and services related to diagnosis, treatment, and / or patient care.

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

[0060] The terms "flocculant", "flocculation agent", "flocculating composition", "coagulant", etc. in this specification refer to substances that can promote the coagulation / agglomeration / aggregation of insoluble particles suspended in water or other aqueous liquids, thereby making it easier to remove the particles by sedimentation / precipitation, filtration, pelletization, and / or other appropriate means. The aggregation of particles can typically be carried out in the process of removing / separating particles from an aqueous suspension. In some embodiments, glucan ester derivatives can be used as flocculants.

[0061] As used herein, the terms "film," "sheet," and similar terms generally refer to thin, visually continuous materials. A film can be configured as a layer or coating on a material or can be standalone (e.g., self-standing, not attached to a material surface). As used herein, "coating" (and similar terms) refers to a thin layer covering a material surface. The term "uniform thickness," as used to characterize a film or coating herein, can refer to a continuous region that is (i) at least 20% of the entire area of the film / coating and (ii) has a standard deviation of thickness of less than, for example, about 50 nm. The term "continuous layer" means a layer of a composition applied to at least a portion of a substrate, where the dried layer of the composition covers more than 99% of the surface to which it is applied and has less than 1% porosity within the layer that exposes the substrate surface. More than 99% of the surface to which the layer is applied excludes any region of the substrate where the layer is not applied. Coatings herein can, in some embodiments, form continuous layers. Coating compositions (and similar terms) herein refer to all solid components that form a layer on a substrate, such as the glucan ester derivatives herein, and optionally pigments, surfactants, dispersants, binders, crosslinking agents, and / or other additives.

[0062] In some embodiments, the terms "one fiber," "fibers," etc. refer herein to staple fibers (staple length fibers) and continuous fibers. Fibers can, herein, include 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, terms such as "fibrid", "glucan fibrid", and "fibrillated glucan" can refer to non-granular, fibrous, or film-like glucan particles in which at least one of their three dimensions is slightly larger relative to the maximum dimension. In some embodiments, the glucan fibrid may have a fiber-like structure and / or a sheet-like structure with a relatively large surface area when compared to glucan fibers. The surface area of the fibrid herein can be, for example, about 5 to 50 meters 2 / gram, the maximum dimension can be about 10 to 1000 microns, and the minimum dimension can be 0.05 to 0.25 microns (the aspect ratio of the maximum dimension to the minimum dimension is 40 to 20000).

[0064] As used herein, terms such as "nonwoven fabric", "nonwoven fabric product", "nonwoven web", etc. refer to a web of individual fibers or filaments that typically intervene in a random or undefined manner. This is in contrast to woven or knitted fabrics that have a definable network of fibers or filaments. In some embodiments, the nonwoven fabric product includes a nonwoven web bonded or attached to another material such as a substrate or backing. In some embodiments, the nonwoven fabric can further contain a binder or adhesive (reinforcing agent) that binds adjacent nonwoven fabric fibers together. The nonwoven fabric binder or adhesive can be applied to the nonwoven fabric, for example, in the form of a dispersion / latex, solution, or solid, and the treated nonwoven fabric is typically dried.

[0065] As used herein, the term "paint" (and similar terms) is a type of coating composition that is a dispersion of pigments in a suitable liquid (e.g., an aqueous liquid) that can be used to form an adhesive coating when spread on the surface of a thin coat. The paint applied to the surface can provide color / decoration, protection, and / or treatment (e.g., primer) to the surface. The paint in some embodiments can be optionally characterized as a latex or latex paint by further including dispersed particles.

[0066] As used herein, the term "composite" includes two or more components including the compositions of the present disclosure (e.g., glucan ester derivatives). Typically, the components of the composite resist separation, and one or more of the components exhibit enhanced and / or different properties compared to their properties alone (i.e., the composite is not simply a mixture that is generally easily separable from its initial components). Composites are generally solid materials herein and can be produced, for example, by extrusion or molding processes.

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

[0068] Various polypeptide amino acid sequences are disclosed herein as characteristics of particular embodiments. Variants of these sequences that are at least about 70 - 85%, 85 - 90%, or 90% - 95% identical to the sequences disclosed herein can be used or referenced. In addition, 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% identity to the sequences disclosed herein. The variant amino acid sequences have the same function / activity as the disclosed sequences or the function / activity of the disclosed sequences is at least about 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, or 99%.

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

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

[0071] The terms "percent by weight", "weight percent (wt%)", "weight - weight percent (% w / w)", etc. are used with the same meaning herein. The percentage by weight refers to the percentage of a substance on a mass basis when contained 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 follows: ((mass of material [g]) / (total volume of material + liquid in which the material is placed [mL])) × 100%. The material can be insoluble in the liquid (i.e., a solid phase in the liquid phase, e.g., a dispersion), or it can be soluble in the liquid (i.e., a solute dissolved in the liquid).

[0073] The term "isolated" means a substance (or process) in a form or environment that does not occur naturally. Non - limiting examples of isolated substances include any glucan ester derivative disclosed herein. The embodiments disclosed herein are synthetic / artifacts (which cannot be manufactured or implemented without human intervention / involvement) and / or are considered to have properties that do not occur naturally.

[0074] As used herein, the term "increased" can refer to an amount 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% more than the amount or activity to which it is being compared. The terms "augmented", "elevated", "enhanced", "exceeded", "improved", etc. are used interchangeably herein.

[0075] Some aspects of the present disclosure relate to compositions comprising ester derivatives of glucan, wherein the glucan has a degree of substitution (DoS) of up to about 3.0 with at least one cationic organic group (cationic acyl group) ester - linked to the glucan. Accordingly, cationic glucan ester derivatives / compounds are disclosed. Further, some aspects relate to compositions comprising ester derivatives of glucan, wherein the glucan has a DoS of up to about 3.0 with at least two organic groups individually ester - linked to the glucan, (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. By "individually ester - linked" is meant that each of the at least two organic groups of (i) and (ii) is linked to the glucan via its own respective ester bond. The glucan ester derivatives can, in some aspects, be characterized as having at least one cationic ester group and at least one hydrophobic ester group, and thus this type of glucan ester can optionally be characterized as amphiphilic.

[0076] The glucan ester derivatives herein can be, for example, α - glucan ester derivatives. The glycosidic bonds of the α - glucan ester derivatives herein are 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% α - glycosidic bonds. Examples of suitable α - glucan ester derivatives include ester derivatives of α - 1,3 - glucan, α - 1,6 - glucan, and α - 1,4 - glucan.

[0077] In some embodiments, 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 linkages (i.e., the ester is an α-1,3-glucan ester). Thus, in some embodiments, the α-glucan ester has about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% or about less than those glycosidic linkages that are not α-1,3. Typically, the glycosidic linkages that are not α-1,3 are mostly or all α-1,6. In some embodiments, the α-glucan ester has no branching points or has less than about 5%, 4%, 3%, 2%, or 1% branching points as a percent of the glycosidic linkages within the α-glucan.

[0078] In some embodiments, the DPw, DPn, or DP of the α-glucan moiety of the α-1,3-glucan ester can be about, at least 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 or less than about them. DPw, DPn, or DP can, in some cases, be expressed as a range between any two of these values. By way of mere example, DPw, DPn, or DP can 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 - 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 mere further example, 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. By way of mere further example, DPw, DPn, or DP can be about 100 - 600, 100 - 500, 100 - 400, 100 - 300, 200 - 600, 200 - 500, 200 - 400, or 200 - 300. In some embodiments, the α-glucan moiety of the α-1,3-glucan ester can have a high molecular weight such that it is reflected in a high intrinsic viscosity (IV).For example, 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 (note that for comparison purposes, 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). The IV herein can be as measured, for example, using an α - glucan polymer dissolved in DMSO having about 0.9 - 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 considering the DoS of the ester and the type of ester group, and such molecular weight can be about, at least about, a calculated value, or about less than those (this mode of molecular weight calculation can be applied to any other polysaccharide / glucan ester derivative disclosed herein).

[0079] The α-1,3-glucan moiety of the α-1,3-glucan ester derivative in this specification can be, for example, (such as molecular weight, linkage profile, and / or manufacturing method), for example, as disclosed in U.S. Patent No. 7,000,000, No. 8,871,474, No. 10,301,604, or No. 10,260,053, or U.S. Patent Application Publication No. 2019 / 0112456, U.S. Patent Application Publication No. 2019 / 0078062, U.S. Patent Application Publication No. 2019 / 0078063, U.S. Patent Application Publication No. 2018 / 0340199, U.S. Patent Application Publication No. 2018 / 0021238, U.S. Patent Application Publication No. 2018 / 0273731, U.S. Patent Application Publication No. 2017 / 0002335, U.S. Patent Application Publication No. 2015 / 0232819, U.S. Patent Application Publication No. 2015 / 0064748, U.S. Patent Application Publication No. 2020 / 0165360, U.S. Patent Application Publication No. 2020 / 0131281, or U.S. Patent Application Publication No. 2019 / 0185893 (each of which is incorporated herein by reference). The α-1,3-glucan can be produced, for example, by an enzymatic reaction involving at least water, sucrose, and a glucosyltransferase enzyme that synthesizes the α-1,3-glucan. The glucosyltransferase, reaction conditions, and / or process that are considered useful for producing insoluble α-glucan can be as disclosed in any of the aforementioned references.

[0080] In some embodiments, the glucosyltransferase enzyme for generating the α-1,3-glucan moiety of the α-1,3-glucan ester derivatives herein is 100% identical to SEQ ID NO: 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 26, 28, 30, 34, or 59, or amino acid residues 55 to 960 of SEQ ID NO: 4, residues 54 to 957 of SEQ ID NO: 65, residues 55 to 960 of SEQ ID NO: 30, residues 55 to 960 of SEQ ID NO: 28, or residues 55 to 960 of SEQ ID NO: 20, or may comprise an amino acid sequence that is at least 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 98.5%, 99%, or 99.5% identical and may have glucosyltransferase activity, and these amino acid sequences are disclosed in U.S. Patent Application Publication No. 2019 / 0078063 and incorporated herein by reference. The glucosyltransferase enzyme comprising SEQ ID NO: 2, 4, 8, 10, 14, 20, 26, 28, 30, 34 or amino acid residues 55 to 960 of SEQ ID NO: 4, residues 54 to 957 of SEQ ID NO: 65, residues 55 to 960 of SEQ ID NO: 30, residues 55 to 960 of SEQ ID NO: 28 or residues 55 to 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 embodiments, 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-1,6 glycosidic linkages (i.e., the ester is an α-1,6-glucan ester or a dextran ester). In some embodiments, a substantially linear dextran ester can comprise 5%, 4%, 3%, 2%, 1%, 0.5% or less glycosidic branching (a linear dextran ester has 100% α-1,6 linkages). When present, the glycosidic branching from the dextran ester is typically short and is a glucose monomer of length 1 (pendent), 2, or 3. In some embodiments, the dextran ester can comprise about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% or about less than those α-1,4, α-1,3 and / or α-1,2 glycosidic linkages. Typically, such linkages are present entirely or nearly entirely as branch points from the α-1,6-glucan.

[0082] The dextran moiety of the dextran ester derivatives herein can have, for example, α-1,2, α-1,3 and / or α-1,4 branches. In some embodiments, about, 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%, 30%, 35%, 40%, 45%, 50%, 2-25%, 2-20%, 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% or less of the total glycosidic linkages of the branched dextran ester are α-1,2, α-1,3, and / or α-1,4 glycosidic branch linkages. Such branches are typically mostly (>90% or >95%) or all (100%) of the length of a single glucose monomer. In some embodiments, dextran having α-1,2-branches can be produced enzymatically according to the procedures of U.S. Patent Application Publication No. 2017 / 0218093 or 2018 / 0282385 (both incorporated herein by reference), where, for example, an α-1,2 branching enzyme such as GTFJ18T1 or GTF9905 can be added during or after the production of dextran. In some embodiments, any other enzyme known to generate α-1,2-branches can be used. For example, dextran having α-1,3-branches can be prepared as disclosed in Vuillemin et al. (2016, J. Biol Chem. 291:7687-7702) or International Patent Application Publication No. 2021 / 007264 pamphlet (incorporated herein by reference).

[0083] The dextran moiety of the dextran ester derivative of the present specification is, for example, about, at least 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 - 500, 3 - 4, 3 - 5, 3 - 6, 3 - 7, 3 - 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 - 115, 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 - 100, 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,It may have a DPw, DPn, or DP of 350 to 2800, 350 to 3000, 500 to 1000, 500 to 1500, 500 to 2000, 500 to 2500, 500 to 2800, 500 to 3000, 500 to 4000, 500 to 5000, 500 to 6000, 600 to 1550, 600 to 1850, 600 to 2000, 600 to 2500, 600 to 3000, 750 to 1000, 750 to 1250, 750 to 1500, 750 to 2000, 750 to 2500, 750 to 3000, 750 to 4000, 750 to 5000, 750 to 6000, 900 to 1250, 900 to 1500, 900 to 2000, 1000 to 1250, 1000 to 1400, 1000 to 1500, 1000 to 2000, 1000 to 2500, 1000 to 3000, 1000 to 4000, 1000 to 5000, 1000 to 6000, or 1100 to 1300 or less than approximately those. In some embodiments, the molecular weight (e.g., Mw or Mn) of the dextran portion of the dextran ester derivative is about or at least about 100,000, 125,000, 150,000, 175,000, 200,000, 240,000, 250,000, 500,000, 750,000, 1,000,000, 2,000,000, 3,000,000, 4,000,000, 5,000,000, 6,000,000, 7,000,000, 8,000,000, 9,000,000, 10,000,000, 20,000,000, 30,000,000, 40,000,000, 50,000,000, 60,000,000, 70,000,000, 80,000,000, 90,000,000, 100,000,000, 110,000,000, 120,000,000, 130,000,000, 140,000,000, 150,000,000, 160,000,000, 170,000,000, 180,000,000, 190,000,000, 200,000,000, 100,000 to 200,000, 125,000 to 175,000, 130,000 to 170,000, 135,000 to 165,000, 140,000 to 160,000, 145,000 to 155,000, 10,000,000 to 80,000,000, 20,000,000 to 70,000,000, 30,000,000 to 60,000,000, 40,000,000 to 50,000,000, 50,000,000 to 200,000,000, 60,000,000 to 200,000,000, 70,000,000 to 200,000,000, 80,000,000 to 200,000,000, 90,000,000 to 200,000,000, 100,000,000 to 200,000,000, 110,000,000 to 200,000,000, 120,000,000 to 200,000,000, 50,000,000 to 180,000,000, 60,000,000 to 180,000,000, 70,000,000 to 180,000,000, 80,000,000 to 180,000,000, 90,000,000 to 180,000,000, 100,000,000 to 180,000,000, 110,000,000 to 180,000,000, 120,000,000 to 180,000,000, 50,000,000 to 160,000,000, 60,000,000 to 160,000,000, 70,000,000 to 160,000,000,80 million to 160 million, 90 million to 160 million, 100 million to 160 million, 110 million to 160 million, 120 million to 160 million, 50 million to 140 million, 60 million to 140 million, 70 million to 140 million, 80 million to 140 million, 90 million to 140 million, 100 million to 140 million, 110 million to 140 million, 120 million to 140 million, 50 million to 120 million, 60 million to 120 million, 70 million to 120 million, 80 million to 120 million, 90 million to 120 million, 90 million to 110 million, 100 million to 120 million, 110 million to 120 million, 50 million to 110 million, 60 million to 110 million, 70 million to 110 million, 80 million to 110 million, 90 million to 110 million, 100 million to 110 million, 50 million to 100 million, 60 million to 100 million, 70 million to 100 million, 80 million to 100 million, 90 million to 100 million or 95 million to 150 million daltons or may be less than about those. The molecular weight (e.g., Mw or Mn) of the dextran moiety of the dextran ester derivative in some embodiments is about, at least 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 to 2000, 1 to 1000, 1 to 500, 1 to 400, 1 to 300, 1 to 200, 1 to 100, 1 to 50, 10 to 2000, 10 to 1000, 10 to 500, 10 to 400, 10 to 300, 10 to 200, 10 to 100, 10 to 50, 20 to 2000, 20 to 1000, 20 to 500, 20 to 400, 20 to 300, 20 to 200, 20 to 100, 20 to 50, 30 to 2000, 30 to 1000, 30 to 500, 30 to 400, 30 to 300, 30 to 200, 30 to 100, 30 to 50, 40 to 2000, 40 to 1000, 40 to 500, 40 to 400, 40 to 300, 40 to 200, 40 to 100, 40 to 50, 50 to 2000, 50 to 1000, 50 to 500, 50 to 400, 50 to 300, 50 to 200, 100 to 2000, 100 to 1000, 100 to 500, 100 to 400, 100 to 300, 100 to 200,It may be 200 to 2000, 20 to 1000, 200 to 500, 200 to 400, 200 to 300, 7.5 to 10, 7.5 to 12.5, 7.5 to 15, 7.5 to 20, 7.5 to 30, 10 to 12.5, 10 to 15, 10 to 20, 10 to 30, 15 to 25, 15 to 30, 40 to 60, 45 to 55, 190 to 210, or 290 to 310 kDa or less than about them. 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 ester group, and such molecular weight can be about, at least about, any of the above molecular weight values or ranges or less than about them. Any of the aforementioned DPw, DPn, DP, or dalton values can, for example, characterize the dextran herein, optionally branched (e.g., α-1,2 and / or α-1,3) before or after.

[0084] The dextran moiety of the dextran ester derivatives in this specification (e.g., molecular weight, linkage / branching profile, method of manufacture) can be, for example, those disclosed in U.S. Patent Application Publication No. 2016 / 0122445, U.S. Patent Application Publication No. 2017 / 0218093, U.S. Patent Application Publication No. 2018 / 0282385, U.S. Patent Application Publication No. 2020 / 0165360, or U.S. Patent Application Publication No. 2019 / 0185893 (each of which is incorporated herein by reference). In some embodiments, the dextran for ester derivatization herein is glucosyltransferase (GTF) 0768 (SEQ ID NO: 1 or 2 of U.S. Patent Application Publication No. 2016 / 0122445), GTF8117, GTF6831, or GTF5604 (the latter three GTF enzymes are SEQ ID NOs: 30, 32, and 33, respectively, of U.S. Patent Application Publication No. 2018 / 0282385), 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 GTF0768, GTF8117, GTF6831, or GTF5604, and can be produced in a suitable reaction.

[0085] In some embodiments, the α-glucan moiety of the α-glucan ester derivative can be in the form of a graft copolymer as disclosed in U.S. Patent Application Publication Nos. 2020 / 0165360, 2019 / 0185893, or 2020 / 0131281, which are hereby incorporated by reference herein. The graft copolymer can include dextran (as the backbone) and α-1,3-glucan (as one or more side chains), and the latter component is 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 the α-1,3-glucan-producing glucosyltransferase as described above. The α-1,3-glucan side chains of the α-glucan graft copolymer herein can be the α-1,3-glucan of the present disclosure. The dextran backbone of the α-glucan graft copolymer herein can be the dextran or α-1,2- and / or α-1,3-branched dextran disclosed herein. In some embodiments, the α-glucan graft copolymer is branched with (A)(i) 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 linkages (i.e., α-1,2,6 and / or α-1,3,6) (e.g., the backbone includes 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), (ii) has an Mw of about 15-25, 15-22.5, 17-25, 17-22.5, 18-22, or 20 kDa, an α-1,6-glucan main chain (100% α-1,6-linkages before α-1,2 and / or α-1,3 branching), and can include (B) one or more (e.g., 2, 3, 4, 5, or 6) α-1,3-glucan side chains extending from one or more of the α-1,2 and / or α-1,3 branches, and such a graft copolymer is typically water-insoluble.

[0086] In some embodiments, 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 linkages (i.e., the ester is an α-1,4-glucan ester). Thus, in some embodiments, the α-1,4-glucan ester has about 50%, 40%, 30%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0% or less glycosidic linkages that are not α-1,4. Examples of α-1,4-glucans include amylose, amylopectin, and starch. α-1,4-glucans such as starch can be derived from, for example, vegetable (e.g., potato, tapioca, pea, palm) or grain (e.g., corn, wheat, rice, barley) sources.

[0087] In some embodiments, the DPw, DPn, or DP of the α-1,4-glucan moiety of the α-1,4-glucan ester derivative can be about, at least 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 or less than about those values. The DPw, DPn, or DP can, in some cases, be expressed as a range between any two of these values. In some embodiments, the DPw, DPn, or DP of the α-1,4-glucan moiety of the α-1,4-glucan ester derivative can be as disclosed above for α-1,3-glucans or α-1,6-glucans.

[0088] The glucan ester derivatives in this specification can be, for example, β-glucan ester derivatives. The glycosidic bonds of the β-glucan ester derivatives in this specification are 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 bonds. Examples of suitable β-glucan ester derivatives include ester derivatives of β-1,3-glucan (e.g., laminarin, paramylon, curdlan), β-1,4-glucan (cellulose), and β-1,6-glucan. In some embodiments, the glucan esters herein are not β-glucan esters and / or do not contain β-glycosidic bonds.

[0089] In some embodiments, 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 linkages (i.e., the ester is a β-1,4-glucan ester). The DPw, DPn, or DP of the β-1,4-glucan moiety of the beta-1,4-glucan ester derivative in some embodiments 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 embodiments, the DPw, DPn, or DP of the β-1,4-glucan moiety 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 embodiments, the glucan esters herein are not β-1,4-glucan esters and / or do not contain β-1,4 glycosidic linkages.

[0090] In some embodiments, 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 linkages (i.e., the ester is a β-1,3-glucan ester). The DPw, DPn, or DP of the β-1,3-glucan moiety of the β-1,3-glucan ester derivative in some embodiments can be, for example, about, at least 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, 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, 16 - 17, 16 - 18, 16 - 19, 16 - 20, 16 - 21, 16 - 22, 16 - 23, 16 - 24, 16 - 25, 16 - 30, 17 - 18, 17 - 19, 17 - 20, 17 - 21, 17 - 22, 17 - 23, 17 - 24, 17 - 25, 17 - 30, 20 - 25, 20 - 30, or 25 - 30 or about less than them. In some embodiments, the DPw, DPn, or DP of the β-1,3-glucan moiety 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 specification, the ester derivative can be a soy polysaccharide ester derivative. The soy polysaccharide portion of the soy polysaccharide ester derivative can, in some aspects, be as disclosed in U.S. Patent Application Publication No. 2018 / 0079832, which is incorporated herein by reference. Thus, any of the features of the present disclosure regarding glucan ester derivatives can similarly characterize embodiments in which a soy polysaccharide ester derivative is used, to the extent that those features are considered appropriate by one of ordinary skill in the art. For example, to the extent that one of ordinary skill in the art considers it appropriate, the term "glucan ester derivative" (and similar terms) used in this disclosure can optionally be replaced with the term "soy polysaccharide ester derivative".

[0092] The ester derivatives of polysaccharides / glucans in some aspects of the present disclosure can have a degree of substitution (DoS) of up to about 3.0 (e.g., from 0.001 to 3.0) with at least two organic groups individually ester - bonded to the glucan, where (i) at least one of the organic groups is a cationic organic group (cationic acyl group) and (ii) at least one of the organic groups is a hydrophobic organic group (hydrophobic acyl group). However, in some aspects, the ester derivative of the polysaccharide / glucan can have a DoS of up to about 3.0 (e.g., from 0.001 to 3.0) with at least one cationic organic group (cationic acyl group) ester - bonded to the polysaccharide / glucan.

[0093] The DoS (or, optionally in this aspect, "total DoS") of the glucans herein having at least one cationic organic group and at least one hydrophobic organic group 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 (the DoS can optionally be expressed as a range between any two of these values). Some examples of DoS ranges herein 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 to 1.9, 0.15 to 1.8, 0.15 to 1.7, 0.15 to 1.6, 0.15 to 1.5, 0.15 to 1.25, 0.15 to 1.0, 0.15 to 0.9, 0.15 to 0.8, 0.15 to 0.7, 0.15 to 0.6, 0.15 to 0.5, 0.2 to 2.0, 0.2 to 1.9, 0.2 to 1.8, 0.2 to 1.7, 0.2 to 1.6, 0.2 to 1.5, 0.2 to 1.25, 0.2 to 1.0, 0.2 to 0.9, 0.2 to 0.8, 0.2 to 0.7, 0.2 to 0.6, 0.2 to 0.5, 0.25 to 2.0, 0.25 to 1.9, 0.25 to 1.8, 0.25 to 1.7, 0.25 to 1.6, 0.25 to 1.5, 0.25 to 1.25, 0.25 to 1.0, 0.25 to 0.9, 0.25 to 0.8, 0.25 to 0.7, 0.25 to 0.6, 0.25 to 0.5, 0.3 to 2.0, 0.3 to 1.9, 0.3 to 1.8, 0.3 to 1.7, 0.3 to 1.6, 0.3 to 1.5, 0.3 to 1.25, 0.3 to 1.0, 0.3 to 0.9, 0.3 to 0.8, 0.3 to 0.7, 0.3 to 0.6, 0.3 to 0.5, 0.4 to 2.0, 0.4 to 1.9, 0.4 to 1.8, 0.4 to 1.7, 0.4 to 1.6, 0.4 to 1.5, 0.4 to 1.25, 0.4 to 1.0, 0.4 to 0.9, 0.4 to 0.8, 0.4 to 0.7, 0.4 to 0.6 and 0.4 to 0.5 are included.

[0094] The DoS of the glucan of the present specification having at least one cationic organic group 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 (the DoS can optionally be expressed as a range between any two of these values). Some examples of DoS ranges in the present specification 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 to 1.5, 0.15 to 1.25, 0.15 to 1.0, 0.15 to 0.9, 0.15 to 0.8, 0.15 to 0.7, 0.15 to 0.6, 0.15 to 0.5, 0.2 to 2.0, 0.2 to 1.9, 0.2 to 1.8, 0.2 to 1.7, 0.2 to 1.6, 0.2 to 1.5, 0.2 to 1.25, 0.2 to 1.0, 0.2 to 0.9, 0.2 to 0.8, 0.2 to 0.7, 0.2 to 0.6, 0.2 to 0.5, 0.25 to 2.0, 0.25 to 1.9, 0.25 to 1.8, 0.25 to 1.7, 0.25 to 1.6, 0.25 to 1.5, 0.25 to 1.25, 0.25 to 1.0, 0.25 to 0.9, 0.25 to 0.8, 0.25 to 0.7, 0.25 to 0.6, 0.25 to 0.5, 0.3 to 2.0, 0.3 to 1.9, 0.3 to 1.8, 0.3 to 1.7, 0.3 to 1.6, 0.3 to 1.5, 0.3 to 1.25, 0.3 to 1.0, 0.3 to 0.9, 0.3 to 0.8, 0.3 to 0.7, 0.3 to 0.6, 0.3 to 0.5, 0.4 to 2.0, 0.4 to 1.9, 0.4 to 1.8, 0.4 to 1.7, 0.4 to 1.6, 0.4 to 1.5, 0.4 to 1.25, 0.4 to 1.0, 0.4 to 0.9, 0.4 to 0.8, 0.4 to 0.7, 0.4 to 0.6 and 0.4 to 0.5 are included.

[0095] The DoS of the glucan of the present specification having at least one cationic organic group 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 (the DoS can optionally be expressed as a range between any two of these values). Some examples of DoS ranges herein 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 to 1.5, 0.15 to 1.25, 0.15 to 1.0, 0.15 to 0.9, 0.15 to 0.8, 0.15 to 0.7, 0.15 to 0.6, 0.15 to 0.5, 0.2 to 2.0, 0.2 to 1.9, 0.2 to 1.8, 0.2 to 1.7, 0.2 to 1.6, 0.2 to 1.5, 0.2 to 1.25, 0.2 to 1.0, 0.2 to 0.9, 0.2 to 0.8, 0.2 to 0.7, 0.2 to 0.6, 0.2 to 0.5, 0.25 to 2.0, 0.25 to 1.9, 0.25 to 1.8, 0.25 to 1.7, 0.25 to 1.6, 0.25 to 1.5, 0.25 to 1.25, 0.25 to 1.0, 0.25 to 0.9, 0.25 to 0.8, 0.25 to 0.7, 0.25 to 0.6, 0.25 to 0.5, 0.3 to 2.0, 0.3 to 1.9, 0.3 to 1.8, 0.3 to 1.7, 0.3 to 1.6, 0.3 to 1.5, 0.3 to 1.25, 0.3 to 1.0, 0.3 to 0.9, 0.3 to 0.8, 0.3 to 0.7, 0.3 to 0.6, 0.3 to 0.5, 0.4 to 2.0, 0.4 to 1.9, 0.4 to 1.8, 0.4 to 1.7, 0.4 to 1.6, 0.4 to 1.5, 0.4 to 1.25, 0.4 to 1.0, 0.4 to 0.9, 0.4 to 0.8, 0.4 to 0.7, 0.4 to 0.6 and 0.4 to 0.5 are included.

[0096] (i) At least one cationic group and (ii) any of the aforementioned DoS values and / or ranges for at least one hydrophobic group can be combined, if necessary, for example, to characterize the DoS profile of the glucan ester derivative herein. In some embodiments, any of the aforementioned values and / or ranges for the total DoS can be combined, if necessary, 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 derivative of the present invention which is a glucan derivative, for example, since there are at most three hydroxyl groups in the glucose monomer unit of glucan, the overall DoS of the glucan ester derivative can be 3.0 or less. The glucan ester derivatives disclosed herein have a DoS having at least one organic group (acyl group) in an ester bond (for example, at least two types of organic groups of the ester bond where at least one group is a cationic group and at least one group is a hydrophobic group) (for example, between about 0.001 and about 3.0), so it will be understood by those skilled in the art that not all substituents of the glucan ester derivative are only hydroxyl groups.

[0098] The ester derivatives of the polysaccharide / glucan of the present disclosure can be substituted with at least one cationic organic group (cationic acyl group) herein that is ester-bonded to the polysaccharide / glucan. The glucan derivatives disclosed herein can be derivatized, for example, with one, two, three or more different types of esterified cationic organic groups herein. In some embodiments, at least one ester-bonded cationic organic group has Structure I:

Chemical formula

[0099] Regarding the wavy line (variable part) of Structure I, since the cationic organic group is ester-bonded to the glucan derivative herein and is thus a cationic acyl group, the -N + R1R2R3 moiety will be understood to be bonded to the glucose monomer unit of the glucan derivative via one or more (chain-like) carbon atoms through a carbonyl (-CO-). Such one or more (chain-like) carbon atoms can be referred to as R c herein. The carbonyl is the -R c -N+ The R1R2R3 moiety is linked to the oxygen atom of the currently substituted hydroxyl group (i.e., the hydrogen atom is substituted by an acyl group). Thus, Structure I can optionally be -CO-R c -N + and described as R1R2R3. When attached to the glucose monomer unit of the glucan, it is -C G -O G -CO-R c -N + and can be described as 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 currently substituted glucose unit.

[0100] In some embodiments, R c (as described above) contains 1 (e.g., -CH2-), 2 (e.g., -CH2CH2), 3 (e.g., -CH2CH2CH2), 4 (e.g., -CH2CH2CH2CH2), 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, or more carbon atoms. R c can be, for example, fully or partially saturated. R c can be, for example, linear. Structure I can be described, for example, as -CO-CH2-N + R1R2R3, -CO-CH2CH2-N + R1R2R3, -CO-CH2CH2CH2-N + R1R2R3, or -CO-CH2CH2CH2CH2-N + R1R2R3.

[0101] R c can have, for example, one or more substitutions having a hydroxyl group (where a hydrogen atom is substituted by another group). R c can, in some embodiments, contain -CH2CH(OH)-, and Structure I containing such R c can be, for example, -CO-CH2CH(OH)-CH2-N +R1R2R3, -CO-CH2CH(OH)-CH2CH2-N + R1R2R3, -CO-CH2CH(OH)-CH2CH2CH2-N + R1R2R3, or -CO-CH2CH(OH)-CH2CH2CH2CH2-N + It can be described as R1R2R3.

[0102] R c can have, for example, one or more branches. In some embodiments, R c is -CHR s -(CH2) p - and can include, where R s is a side chain and p is 0, 1, 2, or 3. R s can be, for example, -CH3, -CH2CH3, -CH2CH2CH3, or -CH2CH2CH2CH3. R s can be, for example, -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 attached to imidazole ring [IMD] carbon-4).

[0103] In some embodiments, such as any of the above structures / formulas, each of R1, R2, and R3 can be as follows. Each of R1, R2, and R3 can be independently selected, for example, from -CH3, -CH2CH3, -CH2CH2CH3, or -CH2CH2CH2CH3 (for example, each of R1, R2, and R3 can be -CH3). In some embodiments, each of R1, R2, and R3 can be independently selected from any mono- or di-hydroxy substituted version of these aforementioned C1-C4 alkyl groups (for example, hydroxyethyl, such as -CH2CH2OH or -CH2(OH)CH3). In some embodiments, each of R1, R2, and R3 can be independently selected from any of the aforementioned C1-C4 alkyl groups and their mono- or di-hydroxy substituted versions. In some embodiments, R1 and R2 can be independently selected from any of the aforementioned C1-C4 alkyl groups and their mono- or di-hydroxy substituted versions (for example, R1 and R2 can be -CH3), and R3 can be as follows. R3 can be, for example, saturated or unsaturated. R3 can be, for example, straight-chain or branched-chain. R3 is -(CH2) n can be alkyl such as CH3, where 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, for example (for example, C6-C22, C12-14, C10-C16, or C8-C18 alkyl); or, optionally, R3 can be an unsaturated form of any of these alkyls. In some embodiments, R3 is -CH2CH2CH2-NH-CO-CH2CH2CH2-(CH2) n can be -CH2CH2CH2CH3, where n is 0, 2, 4, 6, or 10.

[0104] As disclosed above, in some embodiments, the cationic organic group has Structure II:

Chemical formula

[0105] The ester derivatives of the polysaccharides / glucans of the present disclosure can be substituted with at least one hydrophobic organic group (hydrophobic acyl group) herein ester-bonded to the polysaccharide / glucan. The glucan derivatives disclosed herein can be derivatized, for example, with 1, 2, 3 or more different types of esterified hydrophobic acyl groups herein. The hydrophobic acyl group can be represented as -CO-R', where R' is hydrophobic and contains a chain having at least one carbon atom. The carbonyl (-CO-) of the acyl group is bonded to the polysaccharide / glucan monomer (e.g., glucose) via the oxygen atom of the monomer. R' can be, for example, linear, branched, or cyclic. R' can be, for example, saturated or unsaturated and / or can contain up to 29 carbon atoms.

[0106] In some embodiments, the hydrophobic acyl group is "C" ncan be referred to as an "acyl group" (or other similar terms), n is an integer of 2 or more, and represents the number of carbon atoms in the acyl group including the carbonyl carbon atom. C n The acyl group is typically linear and can be either saturated or unsaturated. C n The first carbon (carbon-1) of the acyl group is its carbonyl carbon. In some embodiments, C n the acyl group is ethanoyl (C2), propanoyl (C3), butanoyl (C4), pentanoyl (C5), hexanoyl (C6), heptanoyl (C7), octanoyl (C8), nonanoyl (C9), decanoyl (C 10 ), undecanoyl (C 11 ), dodecanoyl (C 12 ), tridecanoyl (C 13 ), tetradecanoyl (C 14 ), pentadecanoyl (C 15 ), hexadecanoyl (C 16 ), heptadecanoyl (C 17 ), octadecanoyl (C 18 ), nonadecanoyl (C 19 ), eicosanoyl (C 20 ), unneicosanoyl (C 21 ), docosanoyl (C 22 ), tricosanoyl (C 23 ), tetracosanoyl (C 24 ), pentacosanoyl (C 25 ), hexacosanoyl (C 26 ), C 27 , C 28 , C 29 , or C 30 represents an acyl group. These specific C nThe acyl group is saturated. Some common names of the above acyl groups are acetyl (ethanoyl group), propionyl (propanoyl group), butyryl (butanoyl group), valeryl (pentanoyl group), caproyl (hexanoyl group), enanthyl (heptanoyl group), caprylyl (octanoyl group), pelargonyl (nonanoyl group), capryl (decanoyl group), lauroyl (dodecanoyl group), myristyl (tetradecanoyl group), palmityl (hexadecanoyl group), stearyl (octadecanoyl group), arachidyl (eicosanoyl group), behenyl (docosanoyl group), lignoceryl (tetracosanoyl group), and cerotyl (hexacosanoil group). In some embodiments, the acyl group is a C 10 ~C 14 acyl group, which means that the acyl group can be any one of C 10 、C 11 、C 12 、C 13 or C 14 acyl group (this specific C n range nomenclature thus applies to the other C n ranges in this specification). In some embodiments, the acyl group is C2~C 26 、C4~C 20 、C6~C 18 、C8~C 18 、C 10 ~C 18 、C 12 ~C 18 、C6~C 16 、C8~C 16 、C 10 ~C 16 、C 12 ~C 16 、C6~C 14 、C8~C 14 、C 10 ~C 14 、C 12 ~C 14 、C6~C 12 、C8~C 12 、or C 10 ~C 12 acyl group.

[0107] In some embodiments, the hydrophobic acyl group can be unsaturated. The unsaturated acyl group can include, for example, 1, 2, 3, 4, 5, 6 or more double bonds. In some embodiments, the unsaturated acyl group has one or more double bonds spanning carbon (i) 4 and 5, (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 of the acyl group, where the carbon numbering starts from the carbonyl carbon (i.e., carbon-1) of the acyl group. Some suitable combinations of double bonds in the acyl group are as reflected in the following list of unsaturated acyl groups. The double bonds in the acyl group herein can be in the cis or trans orientation, but are typically in the cis orientation. The unsaturated acyl group can be derivable from a fatty acid in some embodiments.Examples of unsaturated acyl groups in this specification include (11Z,14Z)-icosadienoyl, (11Z,14Z,17Z)-icosatrienoil, (4Z)-hexadecenoil, (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl, (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl, (5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl, (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,19Z)-docosapentaenoyl, (8E,10E,12Z)-octadecatrienoyl, (8Z,11Z,14Z)-icosatrienoil, (8Z,11Z,14Z,17Z)-icosatetraenoyl, (9Z)-octadec-9-en-12-ynoyl, (9Z,11E,13E)-octadecatrienoyl, (9Z,11E,13Z)-octadeca-9,11,13-trienoyl, (9Z,12E)-hexadecadienoyl, (9Z,12E)-octadecadienoyl, (9Z,12Z)-octadeca-9,12-dien-6-ynoyl, (9Z,12Z,15Z)-octadeca-9,12,15-trien-6-ynoyl, (Z)-tetradec-7-enoyl, cis,cis-tetradeca-5,8-dienoyl, cis-tetradeca-5-enoyl, arachidonoyl, docosenoyl, dodecenoyl, elaeostearoyl, heptatrienoyl, icosenoyl, linoleoyl, myristoleoyl, octadec-9-ynoyl, octadecenoyl, palmitoleoyl, and oleoyl.

[0108] In some embodiments, the hydrophobic acyl group can contain an aryl group. The arylacyl group can include, for example, a benzoyl group (-CO-C6H5), which can also be referred to as a benzoate group. The arylacyl group in some embodiments can include a benzoyl group substituted with at least one halogen ( "X", e.g., Cl, F), alkyl, halogenated alkyl, ether, cyano, or aldehyde group, or a combination thereof, such as those represented by Structures III(a) to III(r) below:

Chemical formula

[0109] The hydrophobic acyl group can, in some embodiments, contain a branched group. Examples of branched acyl groups herein include 2-methylpropanoyl, 2-methylbutanoyl, 2,2-dimethylpropanoyl, 3-methylbutanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl, 2,2-dimethylbutanoyl, 2,3-dimethylbutanoyl, 3,3-dimethylbutanoyl, 2-ethylbutanoyl, and 2-ethylhexanoyl.

[0110] The polysaccharide / glucan ester derivatives of the present disclosure can, in some embodiments, be characterized as mixed esters by containing at least one cationic ester group herein and at least one hydrophobic ester group herein. By way of mere example, a mixed glucan ester can have an acyl group of betaine herein (e.g., Structure II where R1, R2, and R3 are each -CH3) (e.g., a degree of substitution (DoS) of about 0.01 - 0.12, 0.03 - 0.1, 0.04 - 0.09, or 0.05 - 0.09), and (i) a C 10 ~C 14 acyl group herein (e.g., a C 12and / or (ii) one or both of the arylacyl groups (e.g., benzoyl group) herein (e.g., DoS of about 0.2 to 1.0, 0.3 to 0.9, 0.4 to 0.8, or 0.5 to 0.8). Optionally, such mixed glucan esters can further include an acetyl group (e.g., DoS of about 0.02 to 0.3). In some embodiments, such glucan esters can include as their glucan component α-1,2- and / or α-1,3-branched (e.g., about 15 to 25% branched) α-1,6-glucan (e.g., about 10 to 70, 20 to 60, or 30 to 50 kDa). The polysaccharide / glucan ester derivative may, in some embodiments, not contain other types of substituents other than ester groups, but in other embodiments, one or more other types of substituents may be present.

[0111] The hydrophobic acyl groups of the polysaccharide / glucan ester derivatives herein can be, for example, those disclosed in U.S. Patent Application Publication Nos. 2014 / 0187767, 2018 / 0155455, or 2020 / 0308371, or International Patent Application Publication Pamphlet No. WO 2021 / 252575 (each of which is incorporated herein by reference).

[0112] In some alternative embodiments, the polysaccharides / glucans disclosed herein can be derivatized with anionic organic groups and hydrophobic ester groups (i.e., the anionic organic groups can replace or in addition to the cationic ester groups). The hydrophobic ester groups can be, for example, as disclosed herein (e.g., aryl-containing ester groups such as benzoyl). The anionic organic groups are typically attached to the polysaccharide / glucan via ether or ester linkages. The anionic organic groups can optionally be characterized as anionic ether groups or anionic ester groups. Examples of suitable anionic groups herein include groups derived from carboxyalkyl groups (e.g., carboxymethyl groups), which are examples of ether groups, and cyclic organic anhydrides (e.g., succinic groups), which are examples of ester groups. By way of example only, the polysaccharide / glucan derivatives herein can have (i) carboxymethyl ether and benzoyl ester groups, or (ii) succinic ester and benzoyl ester groups. Suitable anionic groups can be as disclosed in U.S. Patent Application Publication Nos. 2014 / 0179913, 2016 / 0304629, 2020 / 0002646, 2021 / 0253977, 2018 / 0155455, 2023 / 0192905, or International Patent Application Publication Pamphlets WO 2021 / 247810, WO 2022 / 178073, or WO 2022 / 178075, which are incorporated herein by reference. The DoS of the glucans herein having anionic organic groups in the foregoing alternative embodiments can be, for example, as disclosed herein for hydrophobic ester groups or cationic ester groups.

[0113] In some alternative embodiments, the polysaccharides / glucans disclosed herein can be derivatized with anionic organic groups and cationic ester groups (i.e., the anionic organic groups can replace the hydrophobic ester groups or in addition to the hydrophobic ester groups). The cationic ester groups can be, for example, those disclosed herein (e.g., the cationic ester groups of the present specification including Structure I). The anionic organic groups are typically attached to the polysaccharide / glucan via an ether or ester linkage. The anionic organic groups can optionally be characterized as anionic ether groups or anionic ester groups. Examples of suitable anionic groups herein include carboxyalkyl groups (e.g., carboxymethyl groups), and groups derived from cyclic organic anhydrides (e.g., succinic acid groups). By way of mere example, the polysaccharide / glucan derivatives herein can have (i) carboxymethyl ether and Structure I ester groups, or (ii) succinic acid ester and Structure I ester groups. Suitable anionic groups can be, for example, as disclosed in the reference patent applications above. The DoS of the glucans herein having anionic organic groups in the foregoing alternative embodiments can be, for example, as disclosed herein for hydrophobic ester groups or cationic ester groups.

[0114] Some aspects of the present disclosure relate to methods for producing ester derivatives of glucan herein. Such methods (ester derivatization methods / reactions, or esterification methods / reactions) include: (a) a step of contacting glucan with at least two esterifying agents, wherein at least one of the esterifying agents contains a cationic organic group (cationic acyl group), at least one of the esterifying agents contains a hydrophobic organic group (hydrophobic acyl group), at least one cationic organic group and at least one hydrophobic organic group are esterified to the glucan, thereby generating an ester derivative of glucan, and the ester derivative of glucan has a degree of substitution (DoS) of up to about 3.0 with the cationic organic group and the hydrophobic organic group; and (b) optionally, a step of isolating the ester derivative of glucan produced in step (a). Accordingly, any glucan or other polysaccharide disclosed herein can be subjected to the esterification method to produce any ester derivative herein.

[0115] The esterifying agent for the ester derivatization method of the present disclosure can be, for example, a carboxylic acid containing any cationic acyl group disclosed herein. It will be understood that the terminal carbonyl (-CO-) of the cationic acyl group is the carbonyl of the -COOH group of the carboxylic acid containing the cationic acyl group. Here, the use of the term "terminal" distinguishes any internal carbonyl of the acyl group disclosed herein, if present. The carboxylic acid can be provided as a salt with an anion such as chloride, fluoride, or bromide, and the anion balances the N + portion.

[0116] The esterifying agent for the ester derivatization method of the present disclosure can be, for example, a carboxylic acid containing any hydrophobic acyl group disclosed herein. It will be understood that the terminal carbonyl (-CO-) of the hydrophobic acyl group is the carbonyl of the -COOH group of the carboxylic acid containing the hydrophobic acyl group.

[0117] The esterifying agent for the method of ester derivative formation of the present disclosure can be, for example, an acyl halide (acid halide) containing any acyl group disclosed herein. The halide of the acyl halide herein can be, for example, chloride, fluoride or bromide. The esterifying agent for the method of ester derivative formation in some embodiments can be, for example, an acid anhydride containing any acyl group disclosed herein. Some exemplary examples of acid anhydrides include aroyl anhydride (aroyl anhydride) (for example, benzoic anhydride [benzoyl anhydride]), acetic anhydride, propionic anhydride and butyric anhydride.

[0118] 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.

[0119] 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 contains no water or contains, for example, less than about 0.05, 0.1, 0.2, 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 or 2.0 wt% water. The solvent for contacting 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 embodiments, the non-aqueous solvent is N,N-dimethylacetamide (DMAc) (optionally containing about 0.5% to 5% LiCl), dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), pyridine, SO2 / diethylamine (DEA) / DMSO, LiCl / 1,3-dimethyl-2-imidazolidinone (DMI), DMSO / tetrabutylammonium fluoride trihydrate (TBAF), N-methylpyrrolidone, methylene chloride, and / or N-methylmorpholine-N-oxide (NMMO). A dehydrating agent (e.g., tosyl chloride or dicyandiamide) may be included in the contacting step herein.

[0120] The contacting step can be carried out, for example, in a single esterification reaction (a "one-pot" reaction). In some embodiments of the one-pot reaction, at least one cationic esterifying agent and at least one hydrophobic esterifying agent can be provided simultaneously during the reaction, or these agents can be provided continuously to the reaction (e.g., one or more hydrophobic esterifying agents can be added first, followed by one or more cationic esterifying agents, or vice versa). In some embodiments, the contacting step can be carried out over at least two separate reactions, with at least one of the reactions using at least one cationic esterifying agent and at least one of the reactions using at least one hydrophobic esterifying agent. The ester product of the first reaction can optionally be isolated before entering another reaction. In some embodiments, one or more reactions for cationic esterification can be carried out, and then the ester product enters one or more reactions for hydrophobic esterification (or vice versa).

[0121] The concentration of glucan in the esterification reaction herein can be, for example, 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 or at least about 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 50 - 150, 50 - 140, 50 - 130, 60 - 150, 60 - 140, 60 - 130, 70 - 150, 70 - 140, 70 - 130, 60 - 80, or 110 - 130 °C. In some embodiments, the esterification reaction can proceed for about 1, 2, 3, 4, 5, 6, 7, 8, 1 - 8, 2 - 8, 1 - 6, or 2 - 6 hours. The pH of the esterification reaction can be, in some embodiments, about 8.5, 9.0, 9.5, 10.0, 10.5, 11.0, 11.5, or 12.

[0122] The esterified glucan derivatives produced in one or more esterification reactions of the present specification can be optionally isolated. In some embodiments, such products can first be precipitated from the reaction. The precipitation can be carried out by adding an excess amount (e.g., at least 2 to 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 reactants. The precipitated product can then be isolated using a filtering funnel, centrifuge, press filter, or any other method or equipment that enables the removal of liquid from solids. The isolated product can be dried by vacuum drying, air drying, freeze drying, or the like.

[0123] In some embodiments, the esterified glucan derivative product can be isolated by including a step of filtering the completed reactants or a diluted form thereof by ultrafiltration (e.g., a 5 or 10 molecular weight cut-off filter). Optionally, the complete reactants or a diluted form thereof can first be filtered periodically (i.e., not by ultrafiltration), and then the filtrate can be subjected to ultrafiltration. The concentrated liquid obtained by ultrafiltration can then be dried to its constituent solids by freeze drying or the like, or the solids can be precipitated from the liquid and then dried (e.g., by freeze drying).

[0124] The esterified glucan derivative products herein can optionally be washed one or more times with a liquid in which the product does not readily dissolve after precipitation or drying. For example, the glucan ester product can be washed with alcohol, acetone, aromatic compounds, or any combination thereof, depending on the solubility of the ester product therein (lack of solubility may be desirable for washing). Generally, for washing the glucan ester derivative product, a solvent containing an organic solvent such as alcohol (e.g., 95 to 100%) is preferred.

[0125] Any of the above esterification reactions can be repeated using the glucan ester derivative product of this specification as a starting material for further modification. Such further modification can be carried out using the same esterifying agent as used in the first reaction or using a different esterifying agent.

[0126] The compositions of the present disclosure comprising at least one glucan ester derivative herein can be, for example, aqueous compositions (e.g., dispersions such as solutions or colloidal dispersions) or dry compositions. In some embodiments, the compositions herein comprise about, at least 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 weight % or w / v % or about less than them of glucan ester derivative. The compositions can include, for example, ranges between any two of these weight % 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 weight % or w / v %). The liquid component of the aqueous composition can be, for example, 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 weight % of water, or as disclosed below. In some embodiments, the compositions herein can include or be in the form of a solution, dispersion (e.g., emulsion), mixture, wet cake or wet powder, dry powder, extrusion, composite material, film / coating, fiber, or fibrid.

[0127] The solvent of the compositions herein can, in some embodiments, comprise water and at least about 40% (v / v or w / w) of one or more polar organic solvents. In some embodiments, 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, 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 remainder of the solvent is typically water only (e.g., a solvent containing about 75 v / v% polar organic solvent has about 25 v / v% water), but can optionally contain one or more other liquids other than the polar organic solvent (e.g., less than 2, 1, 0.5, or 0.25 v / v%). The solvents herein can optionally be characterized as aqueous solvents considering they have water. The solvents herein typically contain one type of polar organic solvent, but two, three, or more polar organic solvents can optionally be included. In such embodiments, the polar organic solvent concentration is typically the concentration of the combination of polar organic solvents.

[0128] In some embodiments, the polar organic solvent can be protic. Examples of protic polar organic solvents include alcohols (e.g., methanol, ethanol, isopropanol, 1-propanol, tert-butyl alcohol, n-butanol, isobutanol), methylformamide, and formamide. Further examples of protic polar organic solvents herein include n-butanol, ethylene glycol, 2-methoxyethanol, 1-methoxy-2-propanol, glycerol, 1,2-propanediol, and 1,3-propanetriol.

[0129] In some embodiments, the polar organic solvent can be aprotic. Here, examples of aprotic polar organic solvents include acetonitrile, dimethyl sulfoxide, acetone, N,N-dimethylformamide, N,N-dimethylacetamide, tetrahydrofuran, propylene carbonate, sulfolane, and the like. Further examples of aprotic polar organic solvents herein include hexamethylphosphoramide, dimethylimidazolidinone (1,3-dimethyl-2-imidazolidinone), dioxane, nitromethane, and butanone. Generally, esters, ketones, and aldehyde solvents having no acidic hydrogen atoms are other examples of aprotic polar organic solvents herein.

[0130] The aqueous compositions herein can have, for example, a viscosity of about, at least 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, 25 - 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 centipoises (cp) or less than about those. The viscosity can be, for example, as measured using the aqueous compositions herein at any temperature between about 3°C and about 80°C (e.g., 4 - 30°C, 15 - 30°C, 15 - 25°C). The viscosity is typically measured at a pressure of atmospheric pressure (about 760 torr) or ±10% thereof. The viscosity can be measured, for example, using a viscometer or rheometer, and optionally, at a shear rate (rotational shear rate) of, for example, 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 (1 / s), or at a shear rate (rotational shear rate) of about 5, 10, 20, 25, 50, 100, 200, or 250 rpm (revolutions per minute).

[0131] The compositions of the present disclosure can have a turbidity of 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, 18, 16, 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) or less than about those. Any of these NTU values may relate to the α - glucan ester derivative and the solvent component portion of the compositions herein. In some embodiments, any of these NTU levels may be considered to 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 starting from initial preparation). Turbidity can be measured using any suitable method, such as the methodology disclosed in Progress in Filtration and Separation (Edition: 1, Chapter 16. Turbidity: Measurement of Filtrate and Supernatant Quality?, Publisher: Academic Press, Editors: E.S. Tarleton, July 2015), which is incorporated herein by reference, or as described in the following examples.

[0132] In some embodiments, the aqueous solution component of the aqueous composition has no (detectable) dissolved sugar, or has from about 0.1 to 1.5, 0.1 to 1.25, 0.1 to 1.0, 0.1 to 0.75, 0.1 to 0.5, 0.2 to 0.6, 0.3 to 0.5, 0.2, 0.3, 0.4, 0.5 or 0.6 weight % of dissolved sugar. Such dissolved saccharides can include, for example, sucrose, fructose, leucrose and / or soluble gluco-oligosaccharides. The aqueous solution component of the aqueous composition in some embodiments has 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 weight %), and / or can have a pH of, for example, 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 to 10.0, 4.0 to 9.0, 4.0 to 8.0, 5.0 to 10.0, 5.0 to 9.0, 5.0 to 8.0, 6.0 to 10.0, 6.0 to 9.0 or 6.0 to 8.0. In some embodiments, such as esters of insoluble glucan herein (e.g., α-1,3-glucan with DP>8 or >9), the glucan ester is 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 or 1.0 weight %).

[0133] In some embodiments, using an aqueous composition that is an aqueous dispersion (e.g., an emulsion) of particles of the glucan ester of the present disclosure, the particles are dispersed over 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 embodiments, such a level of dispersion (e.g., an emulsion) is considered to be 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 of time (typically starting from the initial preparation of the dispersion).

[0134] The temperature of the compositions herein can be, for example, about, at least about, or up to about 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, 120, 125, 130, 5 - 50, 20 - 25, 20 - 30, 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 °C.

[0135] In some embodiments, the compositions herein can be non - aqueous (e.g., dry compositions). Examples of such embodiments include powders, granules, microcapsules, flakes or any other form of particulate matter. Other examples include larger compositions such as pellets, bars, grains, beads, tablets, sticks or other agglomerates, or ointments or lotions (or any other form of non - aqueous or dry compositions herein). Non - aqueous or dry compositions typically contain about 12, 10, 8, 6, 5, 4, 3, 2, 1.5, 1.0, 0.5, 0.25, 0.10, 0.05 or 0.01 wt% or less water therein. In some embodiments (e.g., those related to laundry or dishwashing detergents), the dry compositions herein can be provided in sachets or pouches.

[0136] Compositions herein containing glucan ester derivatives can be, in some embodiments, detergent compositions. Examples of such compositions are disclosed herein as dishwashing detergents and fabric care detergents.

[0137] In some embodiments, the compositions of the present specification can include salts such as one or more sodium salts (e.g., NaCl, Na2SO4). Other non-limiting examples of salts include (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) acetate, borate, bromate, bromide, carbonate, chlorate, chloride, chlorite, chromate, cyanamide, cyanide, dichromate, dihydrogen phosphate, ferricyanide, ferrocyanide, fluoride, bicarbonate, hydrogen phosphate, bisulfate, hydrogen sulfide, bisulfite, hydride, hydroxide, hypochlorite, iodate, iodide, nitrate, nitride, nitrite, oxalate, oxide, perchlorate, permanganate, peroxide, phosphate, phosphide, phosphite, silicate, stannate, stannite, sulfate, sulfide, sulfite, tartrate, or thiocyanate anions. Thus, for example, any salt having a cation from (i) above and an anion from (ii) above can be included in the composition. The salts can be present in the aqueous compositions of the present specification, for example, at a weight % of about or at least about 0.01, 0.025, 0.05, 0.075, 0.1, 0.25, 0.5, 0.75, 1.0, 1.25, 1.5, 1.75, 2.0, 2.5, 3.0, 3.5, 0.01 - 3.5, 0.5 - 3.5, 0.5 - 2.5, or 0.5 - 1.5 weight % (such weight % values typically refer to the total concentration of one or more salts).

[0138] The compositions of the present specification can optionally contain one or more enzymes (active enzymes). Examples of suitable enzymes include protease, cellulase, hemicellulase, peroxidase, lipolytic enzymes (e.g., metallolipolytic enzymes), xylanase, lipase, phospholipase, esterase (e.g., arylesterase, polyesterase), perhydrolase, cutinase, pectinase, pectate lyase, mannanase, keratinase, reductase, oxidase (e.g., choline oxidase), phenol oxidase, lipoxygenase, ligninase, pullulanase, tannase, pentosanase, melanase, beta-glucanase, arabinosidase, hyaluronidase, chondroitinase, laccase, metalloproteinase, amadoriase, glucoamylase, arabinofuranosidase, phytase, isomerase, transferase, nuclease, and amylase. When enzymes are included, the enzymes can be included in the compositions of the present specification at an active enzyme concentration of, for example, about 0.0001 to 0.1% by weight (e.g., 0.01 to 0.03% by weight) (calculated as pure enzyme protein). For fabric care or automatic dishwashing applications, the enzymes of the present specification (e.g., any of the above such as cellulase, protease, amylase, and / or lipase) can be present in the aqueous composition in which the fabric or dishes are treated (e.g., washing liquid, domestic grey water) at a concentration of from a minimum of about 0.01 to 0.1 ppm of total enzyme protein, or about 0.1 to 10 ppb of total enzyme protein (e.g., less than 1 ppm), up to a maximum of about 100, 200, 500, 1000, 2000, 3000, 4000, or 5000 ppm of total enzyme protein.

[0139] Glucan ester derivatives and / or compositions containing such derivatives are biodegradable in some embodiments. Such biodegradability can be, for example, when determined by the carbon dioxide evolution test method (OECD Guideline 301B, incorporated herein by reference), about, at least about, or up to about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 5 - 60%, 5 - 80%, 5 - 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% - 90% after 15, 30, 45, 60, 75, or 90 days of the test. Such biodegradability is considered to be about, at least about, or up to about 10%, 25%, 50%, 75%, 100%, 150%, 200%, 250%, 500%, 750%, or 1000% higher than that of existing materials.

[0140] The composition can include 1, 2, 3, 4 or more different glucan ester derivatives herein and, optionally, at least one non-derivatized glucan (e.g., as disclosed herein). For example, the composition can include at least one glucan ester derivative and at least one glucan. In some embodiments, the latter can be (or can be) a precursor compound of the former. In some embodiments, there is no non-derivatized α-glucan (e.g., precursor compound).

[0141] The compositions of the present disclosure comprising at least one glucan ester derivative can be in the form of, for example, household care products, personal care products, industrial products, ingestible products (e.g., foods), pharmaceuticals, or medicaments as disclosed in, for example, 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 Pamphlet No. 2016 / 133734. In some embodiments, the composition can comprise at least one constituent / component of a household care product, personal care product, industrial product, pharmaceutical, or ingestible product (e.g., food) as disclosed in any of the aforementioned publications and / or as disclosed herein.

[0142] The compositions in some embodiments are believed to be useful for providing one or more of the following physical properties to personal care products, pharmaceuticals, household products, industrial products, or ingestible products (e.g., foods): for example, thickening, freeze-thaw stability, lubricity, water retention and release, texture, consistency, shape retention, emulsification properties, binding properties, suspension properties, dispersibility, gelling properties, or reduction of mineral hardness.

[0143] Personal care products herein include, but are not particularly limited to, for example, skin care compositions, cosmetic compositions, antifungal compositions, and antibacterial compositions. The personal care products herein can be in the form of, for example, lotions, creams, pastes, mineral oils, ointments, pomades, gels, liquids, combinations thereof, etc. The personal care products disclosed herein can optionally comprise at least one active ingredient. An active ingredient is generally recognized as a component that causes an intended pharmacological effect.

[0144] In some embodiments, the skincare product can be applied to the skin to address skin damage associated with dehydration. The skincare product can also be used to address the appearance of the skin (e.g., to reduce the appearance of scaly, cracked and / or reddened skin) and / or to address the feel of the skin (e.g., to reduce skin roughness and / or dryness while improving skin smoothness and delicacy). The skincare product typically includes at least one active ingredient, such as zinc oxide, petrolatum, white petrolatum, mineral oil, cod liver oil, lanolin, dimethicone, hard fat, vitamin A, allantoin, calamine, kaolin, glycerin or colloidal oatmeal and combinations thereof, to provide a cosmetic effect while treating or preventing skin diseases or providing a moisturizing effect to the skin. The skincare product can include one or more natural moisturizing factors, such as ceramides, hyaluronic acid, glycerin, squalane, amino acids, cholesterol, fatty acids, triglycerides, phospholipids, glycosphingolipids, urea, linoleic acid, glycosaminoglycans, mucopolysaccharides, sodium lactate, or sodium pyrrolidone carboxylate. Other ingredients that can be included in the skincare 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 oil. The skincare product can be, in some embodiments, an ointment, a lotion, or a disinfectant (e.g., a hand disinfectant).

[0145] The personal care products of this specification can also be in the form of, for example, makeup, lipsticks, mascaras, rouges, foundations, blushes, eyeliners, lip liners, lip glosses, other cosmetics, sunscreens, sunblocks, nail polish, nail conditioners, temporary tattoo inks, bath gels, shower gels, body soaps, facial cleansers, lip balms, skin conditioners, cold creams, moisturizers, body sprays, soaps, body scrubs, exfoliants, astringents, scraping lotions, depilatory agents, permanent solutions, anti-dandruff formulations, antiperspirant compositions, deodorants, shaving products, pre-shave products, after-shave products, cleansing agents, skin gels, rinses, toothpaste compositions, toothpastes or mouthwashes. Examples of personal care products (such as cleansing agents, soaps, scrubs, cosmetics) contain a carrier or exfoliant (such as jojoba beads [jojoba ester beads]) (such as about 1 to 10, 3 to 7, 4 to 6 or 5% by weight). Such agents can optionally be dispersed within the product.

[0146] Personal care products in some embodiments may be hair care products. Examples of hair care products herein include shampoos, hair conditioners (leave-in or rinse-out), cream rinses, hair dyes, hair color products, hair dryer products, hair serums, anti-frizz hair products, hair split end repair products, mousses (e.g., hair styling mousse), hair sprays (e.g., hair styling spray), and styling gels (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. The hair care products disclosed herein typically include the following components commonly used in the formulation of 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; humectants, such as propylene glycol, 1,3-butylene glycol, glycerin, sorbitol, pyroglutamic acid salt, amino acids, and / or trimethylglycine; hydrocarbons, such as liquid paraffin, petrolatum, solid paraffin, squalane, and / or olefin oligomers; higher alcohols, such as stearyl alcohol and / or cetyl alcohol; superfatting agents; anti-dandruff agents; disinfectants; anti-inflammatory agents; herbal medicines; water-soluble polymers, such as methyl cellulose, hydroxycellulose, and / or partially deacetylated chitin; preservatives, such as parabens; ultraviolet absorbers; pearlescing agents; pH adjusters; fragrances; and one or more pigments.

[0147] The compositions in some embodiments can be hair styling or hair setting compositions (e.g., hair sprays, hair gels or lotions, hair mousse / foams) (e.g., aerosol hair sprays, non-aerosol pump sprays, splittings, foams, creams, pastes, non-flowing gels, mousses, pomades, lacquers, hair waxes), etc., which are hair care compositions. Hair styling / setting compositions / formulations that can be adapted to contain at least one glucan ester derivative herein can be, for example, those disclosed in U.S. Patent Application Publication No. 20090074697, International Publication No. 1999048462 Pamphlet, U.S. Patent Application Publication No. 20130068849, Japanese Unexamined Patent Application Publication No. 0454116, U.S. Patent No. 5304368, Australian Patent No. 667246B2, U.S. Patent No. 5413775, U.S. Patent No. 5441728, U.S. Patent No. 5939058, Japanese Unexamined Patent Application Publication No. 2001302458, U.S. Patent No. 6346234, U.S. Patent Application Publication No. 20020085988, U.S. Patent No. 7169380, U.S. Patent Application Publication No. 20090060858, U.S. Patent Application Publication No. 20090326151, U.S. Patent Application Publication No. 20160008257, International Publication No. 2020164769 Pamphlet, or U.S. Patent Application Publication No. 20110217256.Hair care compositions such as hair styling / setting compositions may include one or more ingredients / additives, and / or fragrances / perfumes, aromatherapy extracts, herbs, infusions, antibacterial agents, stimulants (e.g., caffeine), essential oils, hair colorants, dyes or colorants, gray inhibitors, antifoaming agents, sunscreens / UV blockers (e.g., benzophenone-4), vitamins, antioxidants, surfactants or other wetting agents, mica, silica, metallic flakes or other luster effect materials, conditioning agents (e.g., volatile or non-volatile silicone fluids), antistatic agents, opacifiers, anti-tack agents, penetrants, preservatives (e.g., phenoxyethanol, ethylhexylglycerin, benzoate, diazolidinyl urea, iodopropynyl butylcarbamate), skin softeners (e.g., panthenol, isopropyl myristate), rheology modifiers or thickening polymers (e.g., acrylate / 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), wetting agents (e.g., glycerin, caprylyl glycol), silicone derivatives, proteins, amino acids (e.g., isoleucine), conditioners, chelating agents (e.g., EDTA), solvents (see below), monosaccharides (e.g., dextrose), disaccharides, oligosaccharides, pH stabilizing compounds (e.g., aminomethylpropanol), film formers (e.g., acrylate / hydroxyester acrylate copolymer, polyvinylpyrrolidone / vinyl acetate copolymer, triethylacetate), aerosol propellants (e.g., propane, isobutane, or n-butane, C3-C5 alkanes such as monoalkyl ethers, dialkyl ethers such as di(C1-C4 alkyl) ethers [e.g., dimethyl ether]), and / or one or more of any other suitable materials herein. The glucan ester derivatives used in the hair styling / setting compositions herein can function, for example, as hair fixing / styling agents (typically non-permanent hair fixing but durable), and optionally as the only hair fixing agent in the composition.Any additional hair fixing / styling agent in this specification includes PVP (polyvinyl pyrrolidone), octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer, vinyl caprolactam / PVP / dimethylaminoethyl methacrylate copolymer, AMPHOMER, or any film-forming agent as described above.

[0148] The total content of one or more glucan ester derivatives in a hair care composition such as a hair styling / setting composition of this specification can be, for example, about, at least about, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 0.5 - 15, 0.5 - 10, 0.5 - 5, 0.5 - 2, 1 - 15, 1 - 10, 1 - 5, 1 - 2, 2.5 - 7.5, 3 - 7, or 4 - 6 weight % or less than about those. The hair styling / hair setting composition can include water and, optionally, a water-miscible (typically polar) organic compound (e.g., a 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) in a solvent. When an organic compound is included, it can constitute, for example, about 10%, 20%, 30%, 40%, 50%, or 60% by weight or volume of the solvent (the remainder being water). The amount of the solvent in the hair styling / setting composition of this specification can be, for example, about 50 - 90, 60 - 90, 70 - 90, 80 - 90, 50 - 95, 60 - 95, 70 - 95, 80 - 95, or 90 - 95 weight %.

[0149] Examples of the hair styling gel formulations of this specification can include about 90 - 95% by weight (e.g., about 92% by weight) of a solvent (e.g., any of those described herein), 0.3 - 1.0% by weight (e.g., about 0.5% by weight) of a thickening agent (e.g., polyacrylic acid), 0.1 - 0.3% by weight (e.g., about 0.2% by weight) of a chelating agent (e.g., EDTA) (optional), 0.2 - 1.0% by weight (e.g., about 0.5% by weight) of a wetting agent (e.g., glycerin), 0.01 - 0.05% by weight (e.g., about 0.02% by weight) of a UV blocker (e.g., benzophenone - 4) (optional), 0.05 - 0.3% by weight (e.g., about 0.1% by weight) of a preservative (e.g., diazolidinyl urea) (optional), 0.5 - 1.2% by weight (e.g., about 0.8% by weight) of an emulsifier (e.g., Ores - 20), 0.1 - 0.3% by weight (e.g., about 0.2% by weight) of a fragrance / flavor (optional), 0.2 - 1.0% by weight (e.g., about 0.5% by weight) of a pH stabilizing compound (e.g., aminomethylpropanol), and 3 - 7% by weight (e.g., about 5% by weight) of the glucan ester derivative of this specification (e.g., as a hair fixing / styling agent).

[0150] Examples of the hair styling spray formulations herein include about 0.2 to 1.0 wt% (e.g., about 0.5 wt%) of a pH stabilizing compound (e.g., aminomethylpropanol), 0.1 to 0.3 wt% (e.g., about 0.2 wt%) of a fragrance / perfume (optional), 0.05 to 0.12 wt% (e.g., about 0.08 wt%) of a surfactant (e.g., ethoxylated dimethicone polyol), 0.05 to 0.12 wt% (e.g., about 0.08 wt%) of a conditioner (e.g., cyclomethicone) (optional), 0.05 to 0.3 wt% (e.g., about 0.2 wt%) of a preservative (e.g., sodium benzoate) (optional), 15 to 20 wt% (e.g., about 17 wt%) of water, 30 to 40 wt% (e.g., about 65 wt%) of an alcohol (e.g., ethanol), 40 to 60 wt% (e.g., about 45 wt%) of a propellant (e.g., dimethyl ether, or a mixture of about 2:1 of dimethyl ether and C3 - C5 alkanes [e.g., a mixture of propane and isobutane]), and 2 to 4 wt% (e.g., about 2.75 wt%) of the glucan ester derivative herein (e.g., as a hair fixative / styling agent).

[0151] Some aspects of the present disclosure relate to hair treated with the hair care compositions herein (e.g., hair styling / setting compositions, shampoos, or conditioners). For example, the hair can contain, on its surface, e.g., in a film / coating of the hair, a glucan ester derivative, and / or can adsorb or deposit in other ways on the hair surface, and optionally, one or more other components of the hair care compositions herein can also be present. Typically, the hair of the present disclosure, e.g., hair having a coating containing an α - glucan ester, does not show flaking to the naked eye (i.e., there is little or no significant peeling).

[0152] Various examples of personal care formulations containing at least one glucan ester derivative of the present disclosure are disclosed below (1 - 3).

[0153] A hair conditioner composition comprising (1) cetyl alcohol (1 - 3%), isopropyl myristate (1 - 3%), hydroxyethyl cellulose (Natrosol® 250HHR, 0.1 - 1%), glucan ester derivative (0.1 - 2%), potassium salt (0.1 - 0.5%), Germaben® II preservative (0.5%, available from International Specialty Products), and the balance water.

[0154] A hair shampoo composition comprising (2) 5 - 20% sodium lauryl sulfate (SLES), 1 - 2 wt% cocamidopropyl betaine, 1 - 2 wt% sodium chloride, 0.1 - 2% glucan ester derivative, preservative (0.1 - 0.5%), and the balance water.

[0155] A skin lotion composition comprising (3) 1 - 5% glycerin, 1 - 5% glycol stearate, 1 - 5% stearic acid, 1 - 5% mineral oil, 0.5 - 1% acetylated lanolin (Lipolan® 98), 0.1 - 0.5% cetyl alcohol, 0.2 - 1% triethanolamine, 0.1 - 1 wt% Germaben® II preservative, 0.5 - 2 wt% glucan ester derivative, and the balance water.

[0156] The pharmaceutical of this specification can be in the form of, for example, an emulsion, liquid, elixir, gel, suspension, solution, cream or ointment. Also, the pharmaceutical of this specification can be in any form of the personal care products disclosed herein, such as in the form of an antibacterial or antifungal composition, etc. The pharmaceutical can further comprise one or more pharmaceutically acceptable carriers, diluents and / or pharmaceutically acceptable salts. The compositions of this specification can also be used, for example, in capsules, tablets, tablet coatings, and as excipients for pharmaceuticals and drugs.

[0157] The household and / or industrial products of this specification can be in the form of, for example, drywall tape joint compound, mortar, grout, cement plaster, spray plaster, cement stucco, adhesives, pastes, wall / ceiling binders, tape casting, extrusion, injection molding, and binders and processing aids for 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 cleaners, polymer emulsions, latexes, gels such as aqueous gels, surfactant solutions, paints such as aqueous paints, protective coatings, adhesives, sealants and caulking agents, inks such as aqueous inks, metal cutting fluids, films or coatings, or emulsion-based metal cleaning fluids used in electroplating, phosphating, zinc plating and / or general metal cleaning operations. In some embodiments, the compositions of this specification are included in a fluid as, for example, viscosity modifiers and / or friction reducers, and such uses include downhole operations / fluids (such as in hydraulic fracturing and enhanced oil recovery).

[0158] Some aspects of this specification relate to an aqueous solution having (i) salt water such as seawater, or (ii) at least one water-soluble glucan ester derivative of the present disclosure, and having one salt or combination of salts (e.g., including at least NaCl) 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%. The concentration of such a glucan ester derivative in water of (i) or (ii) can be, for example, about, at least 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 0.1-0.2 wt%, or about less than that. Despite the relatively high salt concentration in such aqueous compositions, in some aspects, the glucan ester derivative is thought to remain completely or mostly in solution and be able to provide viscosity. Such a solution of (i) or (ii) viscosity-modified by a glucan ester derivative herein can be one used within a system that utilizes such a solution (e.g., any of those herein such as downhole operations).

[0159] Examples of ingestible products herein include foods, beverages, animal feeds, animal health and / or nutrition products, and / or pharmaceuticals. The intended uses of the presently disclosed compositions in ingestible products can be, for example, to provide texture, add volume, and / or thicken.

[0160] Further examples of using the compositions of the present disclosure for ingestible products include the following uses: bulking, binding, and / or coating components; carriers for colorants, flavoring agents / flavors, and / or high-intensity sweeteners; spray-dried additives; bulking agents, thickeners, dispersants, and / or emulsifiers; and components that promote moisture retention (humectants). Examples of products that can be prepared using the compositions herein include foods, beverage products, pharmaceuticals, nutritional products, and sports products. Examples of beverage products herein include concentrated beverage mixtures, carbonated beverages, non-carbonated beverages, fruit-flavored beverages, fruit juices, teas, coffees, milks, nectars, powdered beverages, liquid concentrates, milk beverages, ready-to-drink (RTD) products, smoothies, alcoholic beverages, flavored waters, and combinations thereof. Examples of foods herein include baked products (e.g., bread), confections, frozen dairy products, meats, artificial / synthetic / cultured meats, grain products (e.g., breakfast cereals), dairy products (e.g., yogurt), spices (e.g., mustard, ketchup, mayonnaise), snack bars, soups, dressings, mixes, processed foods, baby foods, diet foods, peanut butter, syrups, sweeteners, food coatings, pet foods, animal feeds, animal health nutritional products, dried fruits, sauces, gravy sauce, jams / jellies, dessert products, spreads, butter, breadcrumbs, spice mixes, sugar coatings, and the like. In some embodiments, the compositions herein can provide or enhance foaming of beverages (e.g., for hot 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., coffee [e.g., cappuccino], tea [e.g., chai tea])).

[0161] The compositions herein containing glucan ester derivatives can be included in personal care products, pharmaceuticals, household products, industrial products, or ingestible products (e.g., foods), for example, in an amount that provides the desired degree of thickening and / or dispersion. Examples of the concentration or amount of the disclosed compositions in the products are any of the weight percentages provided herein.

[0162] In some embodiments, a composition comprising at least one glucan ester derivative of the present specification can be in the form of a fabric care composition or can include the same. The fabric care composition can be used for hand washing, washing machine cleaning and / or other purposes such as other purposes like fabric immersion and / or pretreatment. The fabric care composition can be, for example, a laundry detergent; a fabric conditioner, any laundry product, a rinse product or a dryer additive product; and can take the form of a unit dose or a spray. The fabric care composition in liquid form can be in the form of an aqueous composition. In other embodiments, the fabric care composition can be in a dry form such as, for example, a granular detergent or a dryer-added fabric softener sheet. Other non-limiting examples of the fabric care composition of the present specification include granular or powdered all-purpose or heavy-duty detergents; all-purpose or heavy-duty detergents in liquid, gel or paste form; liquid or dry detergents for fine (e.g., delicate) fibers; cleaning aids such as, for example, bleach additives, "stain sticks" or pretreatments; substrate-loaded products such as dry wipes or wet wipes, pads or sponges; sprays and mists; and water-soluble unit dose products. As a further example, the composition of the present specification can be in the form of a liquid, gel, powder, hydrophilic colloid, aqueous solution, granule, tablet, capsule, bead or troche, single-compartment sachet, multi-compartment sachet, single-compartment pouch, or multi-compartment pouch.

[0163] The detergent composition of the present specification can be in any useful form such as, for example, powder, granule, paste, bar, unit dose or liquid. The liquid detergent can typically be aqueous and contain up to about 70% by weight of water and 0% to about 30% by weight of an organic solvent. The liquid detergent can also be in the form of a compact gel containing only about 30% by weight of water.

[0164] A detergent composition (e.g., a fabric care product or any other product herein) typically contains one or more surfactants, which are 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 concentration of about 0.1 wt% to about 60 wt% of the detergent composition, and in alternative embodiments, the concentration is about 1 wt% to about 50 wt%, and in still further embodiments, the concentration is about 5 wt% to about 40 wt%. The detergent usually contains 0 wt% to about 50 wt% of an anionic surfactant, such as linear alkylbenzene sulfonate (LAS), α-olefin sulfonate (AOS), alkyl sulfate (higher alcohol sulfate ester salt) (AS), alcohol ethoxysulfate (AEOS or AES), secondary alkane sulfonate (SAS), α-sulfo fatty acid methyl ester, 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 ethoxylate (AEO or AE) (e.g., as described in WO 92 / 06154 pamphlet, which is incorporated herein by reference), carboxylated alcohol ethoxylate, nonylphenol ethoxylate, alkyl polyglycoside, alkyl dimethylamine oxide, ethoxylated fatty acid monoethanolamine, fatty acid monoethanolamide, or polyhydroxyalkyl fatty acid amide.

[0165] The detergent composition of the present specification optionally includes one or more detergent builders or builder systems. In some embodiments, oxidized α-1,3-glucan can be included as a cobuilder, and the oxidized α-1,3-glucan compound for use herein is disclosed in U.S. Patent Application Publication No. 2015 / 0259439. In some embodiments incorporating at least one builder, the cleaning composition comprises the builder in at least about 1 wt%, about 3 wt% to about 60 wt% or even about 5 wt% to about 40 wt% of the composition. Examples of builders include alkali metals, ammonium salts and alkanolammonium salts of polyphosphoric acids, alkali metal silicates, alkaline earths and alkali metal carbonates, aluminosilicates, polycarboxylic acid compounds, ether hydroxy polycarboxylates, copolymers of maleic anhydride and ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulfonic acid and carboxymethyloxysuccinic acid, various alkali metal salts, ammonium salts and substituted ammonium salts of polyacetic acid, such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, and 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. Further examples of detergent builders or complexing agents include zeolites, diphosphates, triphosphates, phosphonates, citrates, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTMPA), alkyl succinic acids and alkenyl succinic acids, soluble silicates or layered silicates (e.g., SKS-6 manufactured by Hoechst).

[0166] In some embodiments, the builder forms water-soluble hard ion complexes (e.g., metal ion sequestering builders) such as citrate and polyphosphates (e.g., sodium tripolyphosphate, sodium tripolyphosphate hexahydrate, potassium tripolyphosphate, and mixed sodium·potassium tripolyphosphate, etc.). Any suitable builder is contemplated for use in this disclosure, including builders known in the art (see, e.g., European Patent No. 2100949).

[0167] In some embodiments, suitable builders can 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 concentration of 0.1 wt% to 80 wt%, 5 wt% to 60 wt% or 10 wt% to 50 wt% of the composition. In some embodiments, the product includes a mixture of a phosphate builder and a non-phosphate builder. Suitable phosphate builders include monophosphates, diphosphates, triphosphates or oligomeric polyphosphates, e.g., alkali metal salts of these compounds, e.g., sodium salts. In some embodiments, the builder can be sodium tripolyphosphate (STPP). Further, the composition can include carbonates and / or citrates, preferably citrates which help to achieve a neutral pH composition. Other suitable non-phosphate builders include homopolymers and copolymers of polycarboxylic acids and their partial or complete neutralization salts, monomeric polycarboxylic acids and hydroxycarboxylic acids and their salts. In some embodiments, salts of the above compounds include ammonium salts and / or alkali metal salts, i.e., lithium salts, sodium salts and potassium salts, e.g., sodium salts. Suitable polycarboxylic acids include acyclic, alicyclic, heterocyclic and aromatic carboxylic acids, where in some embodiments, they can each contain at least two carboxyl groups which can be separated from each other, in some instances by two or fewer carbon atoms in each case.

[0168] The detergent composition of the present specification 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 using at least one chelating agent, the composition contains from about 0.1% to about 15% by weight or further from about 3.0% to about 10% by weight of the chelating agent based on the composition.

[0169] The detergent composition of the present specification 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 polyterephthalic acid, clays such as kaolinite, montmorillonite, attapulgite, illite, bentonite, halloysite and mixtures thereof.

[0170] The detergent composition of the present specification may contain one or more dye transfer inhibitors. Suitable polymeric dye transfer inhibitors include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, copolymers of polyvinyl oxazolidone and polyvinylimidazole, or mixtures thereof. Further dye transfer inhibitors include manganese phthalocyanine, peroxidase, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, copolymers of polyvinyl oxazolidone and polyvinylimidazole, and / or mixtures thereof. Examples of such chelating agents include ethylenediaminetetraacetic acid (EDTA); diethylenetriaminepentamethylenephosphonic acid (DTPMP); hydroxy-ethanediphosphonic acid (HEDP); ethylenediamine N,N'-disuccinic acid (EDDS); methylglycine diacetic acid (MGDA); diethylenetriaminepentaacetic acid (DTPA); propylenediaminetetraacetic acid (PDTA); 2-hydroxypyridine-N-oxide (HPNO); or methylglycine diacetic acid (MGDA); glutamic acid N,N-diacetic acid (tetrasodium salt of N,N-dicarboxymethylglutamic acid) (GLDA); nitrilotriacetic acid (NTA); 4,5-dihydroxy-m-benzenedisulfonic acid; citric acid and any salts thereof; N-hydroxyethylethylenediaminetriacetic acid (HEDTA), triethylenetetraminehexaacetic acid (TTHA), N-hydroxyethyliminodiacetic acid (HEIDA), dihydroxyethylglycine (DHEG), ethylenediaminetetrapropionic acid (EDTP), and derivatives thereof that can be used alone or in combination with any of the above. In embodiments using at least one dye transfer inhibitor, the composition of the present specification may comprise from about 0.0001% to about 10% by weight, from about 0.01% to about 5% by weight, or more preferably from about 0.1% to about 3% by weight of the composition.

[0171] The detergent composition of the present specification may contain silicate. In some of these embodiments, the use of sodium silicate (e.g., disodium silicate, sodium metasilicate, and / or phyllosilicate) is seen. In some embodiments, the silicate is present at a concentration of about 1 wt% to about 20 wt% of the composition. In some embodiments, the silicate is present at a concentration of about 5 wt% to about 15 wt% of the present composition.

[0172] The detergent composition of the present specification may contain a dispersant. Suitable water-soluble organic materials include, but are not limited to, homopolymeric acids or copolymeric acids containing at least two carboxyl groups separated from each other by two or fewer carbon atoms, or salts thereof.

[0173] The detergent composition of the present specification may additionally contain, for example, one or more of the enzymes disclosed above. In some aspects, the detergent composition may contain one or more enzymes, each at a concentration of about 0.00001 wt% to about 10 wt% of the composition, and the remaining amount of cleaning auxiliary substances. In some other aspects, the detergent composition may also contain each enzyme at a concentration of about 0.0001 wt% to about 10 wt%, about 0.001 wt% to about 5 wt%, about 0.001 wt% to about 2 wt%, or about 0.005 wt% to about 0.5 wt% of the composition. The enzymes contained in the detergent composition of the present specification can be stabilized using conventional stabilizers, such as polyols, sugars or sugar alcohols, lactic acid, boric acid or boric acid derivatives (e.g., aromatic borate esters), such as propylene glycol or glycerol.

[0174] In some aspects, the cleaning agent composition may contain one or more other types of polymers in addition to the glucan ester derivatives disclosed herein. Examples of other types of polymers useful herein include carboxymethyl cellulose (CMC), dextran, poly(vinyl pyrrolidone) (PVP), polyethylene glycol (PEG), poly(vinyl alcohol) (PVA), polycarboxylates, such as polyacrylate, maleic acid / acrylic acid copolymer, and lauryl methacrylate / acrylic acid copolymer.

[0175] The detergent composition of the present specification may contain a bleaching system. For example, the bleaching system may include a perborate or percarbonate that can bind to an H2O2 source, such as a peracid-forming bleach activator, such as tetraacetylethylenediamine (TAED) or nonanoyloxybenzenesulfonate (NOBS). Alternatively, the bleaching system may contain a peroxy acid (e.g., an amide, imide, or sulfone type peroxy acid). Instead, furthermore, the bleaching system may be an enzymatic bleaching system containing a perhydrolase, such as the system described in WO 2005 / 056783 pamphlet, etc.

[0176] The detergent composition of the present specification may also contain conventional detergent components such as a fabric conditioner, viscosity, foam boosting agent, foam suppressing agent, corrosion inhibitor, soil suspending agent, recontamination preventing agent, dye, bactericide, anti-discoloring agent, fluorescent brightening agent, or perfume. The pH of the detergent composition of the present specification (measured in an aqueous solution at the use concentration) is usually neutral or alkaline (e.g., a pH of about 7.0 to about 11.0).

[0177] Examples of suitable anti-redeposition agents and / or clay soil removal agents for the fabric care products of the present specification include polyethoxy amphoteric surfactants, water-soluble copolymers of acrylic acid or methacrylic acid and acrylic acid or methacrylic acid - ethylene oxide condensates (e.g., U.S. Patent No. 3,719,647), cellulose derivatives such as carboxymethyl cellulose and hydroxypropyl cellulose (e.g., U.S. Patent Nos. 3,597,416 and 3,523,088), and mixtures containing nonionic alkyl polyethoxy surfactants, polyethoxyalkyl quaternary cationic surfactants, and fatty acid amide surfactants (e.g., U.S. Patent No. 4,228,044). Non-limiting examples of other suitable anti-redeposition agents and clay soil removal agents are disclosed in U.S. Patent Nos. 4,597,898 and 4,891,160 and Patent Application Publication WO 95 / 32272 (all of which are incorporated herein by reference).

[0178] Certain forms of detergent compositions that can be adapted to the purposes of the present specification are disclosed, for example, in US Patent Application Publication No. 20090209445A1, US Patent Application Publication No. 20100081598A1, US Patent No. 7001878B2, European Patent No. 1504994B1, International Publication No. 2001085888A2 Pamphlet, International Publication No. 2003089562A1 Pamphlet, International Publication No. 2009098659A1 Pamphlet, International Publication No. 2009098660A1 Pamphlet, International Publication No. 2009112992A1 Pamphlet, International Publication No. 2009124160A1 Pamphlet, International Publication No. 2009152031A1 Pamphlet, International Publication No. 2010059483A1 Pamphlet, International Publication No. 2010088112A1 Pamphlet, International Publication No. 2010090915A1 Pamphlet, International Publication No. 2010135238A1 Pamphlet, International Publication No. 2011094687A1 Pamphlet, International Publication No. 2011094690A1 Pamphlet, International Publication No. 2011127102A1 Pamphlet, International Publication No. 2011163428A1 Pamphlet, International Publication No. 2008000567A1 Pamphlet, International Publication No. 2006045391A1 Pamphlet, International Publication No. 2006007911A1 Pamphlet, International Publication No. 2012027404A1 Pamphlet, European Patent No. 1740690B1, International Publication No. 2012059336A1 Pamphlet, US Patent No. 6730646B1, International Publication No. 2008087426A1 Pamphlet, International Publication No. 2010116139A1 Pamphlet, and International Publication No. 2012104613 Pamphlet, all of which are incorporated herein by reference in their entirety.

[0179] The detergent composition for washing in this specification can optionally be a heavy-duty (all-purpose) detergent composition. A typical heavy-duty detergent composition contains an anionic detergency surfactant (selected from the group consisting of linear or branched or random-chain substituted or unsubstituted alkyl sulfates, alkyl sulfonates, alkoxylated alkyl 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 alkoxylated alcohol alkyls, such as C8-C18 ethoxylated alkyl alcohols and / or C6-C12 alkylphenol alkoxylates) as detergency surfactants (10 wt / wt% - 40 wt / wt%), wherein the weight ratio of the anionic detergency surfactant (having a hydrophilicity index (HIc) of 6.0 - 9) to the nonionic detergency surfactant is greater than 1:1. Suitable detergency surfactants further include cationic detergency surfactants (selected from the group consisting of alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl ternary sulfonium compounds and / or mixtures thereof); zwitterionic and / or amphoteric detergency surfactants (selected from the group of alkanolamine sulfobetaines); amphoteric surfactants; semi-polar nonionic surfactants, and mixtures thereof.

[0180] The detergents of this specification, such as heavy-duty laundry detergent compositions, may optionally contain a surfactant-enhancing polymer consisting of an amphiphilic alkoxylated grease cleaning polymer (an alkoxylated polymer having branched hydrophilic and hydrophobic properties, for example, selected from the group consisting of alkoxylated polyalkyleneimines in the range of 0.05 wt% to 10 wt%) and / or a random graft polymer (typically, 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 polyalcohols such as glycerol and mixtures thereof, and a hydrophobic side chain selected from the group consisting of C4-C25 alkyl groups, polypropylene, polybutylene, vinyl esters of saturated C1-C6 monocarboxylic acids, C1-C6 alkyl esters of acrylic acid or methacrylic acid, and mixtures thereof).

[0181] For example, the detergents of the present specification such as heavy-duty laundry detergent compositions may optionally contain additional polymers, such as soil-release polymers (anionic end-capped polyesters, for example, polymers containing at least one monomer unit selected from sugars, dicarboxylic acids, polyols and combinations thereof having a random or block structure, such as SRP1, polymers based on ethylene terephthalate having a random or block structure and copolymers thereof, such as REPEL-O-TEX SF, SF-2 AND SRP6, TEXCARE SRA100, SRA300, SRN100, SRN170, SRN240, SRN300 AND SRN325, MARLOQUEST SL). The anti-redeposition agents of the present specification (0.1 wt% to 10 wt%) contain carboxylate polymers having a molecular weight in the range of 500 to 100,000 Da, for example, 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, vinyl pyrrolidone homopolymer and / or polymers containing at least one monomer selected from polyethylene glycol; and polymer carboxylates (for example, maleate / acrylate random copolymers or polyacrylate homopolymers).

[0182] For example, the detergents of the present specification such as heavy-duty laundry detergent compositions may optionally further contain saturated or unsaturated fatty acids, preferably saturated or unsaturated C12-C24 fatty acids (0 wt% to 10 wt%); deposition aids disclosed herein (examples of which include polysaccharides, cellulose polymers, polydiallyldimethylammonium halides (DADMAC) and copolymers of DAD MAC with vinyl pyrrolidone, acrylamide, imidazole, imidazolium halides and mixtures thereof having a random or block structure, cationic guar gum, cationic starch, cationic polyacrylamide and mixtures thereof) may be included.

[0183] The detergents of this specification, such as heavy-duty detergent compositions, may optionally further contain at least one dye transfer inhibitor, examples of which are described above.

[0184] For example, the detergents of this specification, such as heavy-duty detergent compositions, may optionally contain a silicone- or fatty acid-based suds suppressor; a hueing dye, calcium cations and magnesium cations, a visual signal transduction component, an antifoaming agent (0.001 wt% to about 4.0 wt%) and / or diglycerides and triglycerides, ethylene glycol distearate, microcrystalline cellulose, microfibrillated cellulose, biopolymers, xanthan gum, gellan gum, and mixtures thereof, a structuring agent / thickener (0.01 wt% to about 5 wt%) selected from the group consisting of. The structuring agent can also be called a structurant.

[0185] The detergent of this specification can be, for example, in the form of a heavy-duty dry / solid laundry detergent composition. Such detergents 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, and mixtures thereof; (ii) a builder, such as any phosphorus-free builder (e.g., 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, citrate, and nitrilotriacetic acid, any silicate (e.g., sodium 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) a bleaching agent, such as a photo-bleaching agent (e.g., sulfonated zinc phthalocyanine, sulfonated aluminum phthalocyanine, xanthene dyes, and mixtures thereof), any hydrophobic or hydrophilic bleach activator (e.g., dodecanoyloxybenzenesulfonate, decanoyloxybenzenesulfonate, decanoyloxybenzoic acid or its salts, 3,5,5-trimethylhexanoyloxybenzenesulfonate, tetraacetylethylenediamine - TAED, nonanoyloxybenzenesulfonate - NOBS, nitril quat, and mixtures thereof), any source of hydrogen peroxide (e.g., examples include inorganic perhydrate salts containing mono- or tetrahydrate sodium salts of perborate, percarbonate, persulfate, perphosphate, or persilicate), any pre-formed hydrophilic and / or hydrophobic peracid (e.g., percarboxylic acids and salts, percarbonic acids and salts, perimidic acids and salts, peroxomonosulfuric acid and salts, and mixtures thereof);and / or (iv) any other components, such as bleach catalysts (e.g., imine-based bleach boosters including iminium cations and polyions, iminium zwitterions, modified amines, modified amine oxides, N-sulfonylimines, N-phosphonylimines, N-acylimines, 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 together with auxiliary metal cations such as zinc or aluminum and sequestering agents for metal ions such as EDTA, ethylenediaminetetra(methylenephosphonic acid)) may be included.;

[0186] For example, the detergents herein, such as those for fabric care (e.g., laundering), may be included in unit dosages (e.g., sachets or pouches). The unit dosage form may include a water-soluble outer film that completely encloses the liquid or solid detergent composition. The unit dosage may include a single compartment or at least two, three, or more (multiple) compartments. The multiple compartments may be arranged in a stacked orientation or a side-by-side orientation. The unit dosages herein are typically in a closed structure of any form / shape suitable for holding and protecting the contents without releasing the contents prior to contact with water.

[0187] In some embodiments, a composition comprising at least one glucan ester derivative herein can be in the form of a fabric softener (liquid fabric softener) or can include it. Examples of such compositions are typically rinses used when washing a material-containing fabric after washing the material-containing fabric in a washing detergent composition (e.g., fabric rinse as used in a fabric rinse cycle in a washing machine). The concentration of the glucan ester derivative in a composition comprising a fabric softener (e.g., a rinse) 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 the fabric softener in the composition (e.g., a rinse) 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 based on the individual components of the fabric softener) or can be based on one or more fabric softeners in the fabric softener formulation. The fabric softener herein can further include, for example, one or more of a fabric softener (e.g., diethylester dimethylammonium chloride), an antistatic agent, a fragrance, a wetting agent, a viscosity modifier (e.g., calcium chloride), a pH buffer / buffer (e.g., formic acid), an antibacterial agent, an antioxidant, a radical scavenger (e.g., ammonium chloride), a chelating agent / builder (e.g., diethylenetriaminepentaacetate), an antifoaming agent / lubricant (e.g., polydimethylsiloxane), a preservative (e.g., benzisothiazolinone), and a colorant. In some embodiments, the fabric softener can further include one or more of a fabric softener, a viscosity modifier, a pH buffer / buffer, a radical scavenger, a chelating agent / builder, and an antifoaming agent / lubricant.The fabric softener can, in some embodiments, be fragrance-free and / or dye-free, or have less than about 0.1% by weight of fragrance and / or dye. In some embodiments, the fabric softener suitable for use herein can be as disclosed in U.S. Patent Application Publication Nos. 2014 / 0366282, 2001 / 0018410, 2006 / 0058214, 2021 / 0317384 or 2006 / 0014655, or Patent Application Publication International Publication Nos. 2007 / 078782 Pamphlet, 1998 / 016538 Pamphlet, 1998 / 012293 Pamphlet, 1998007920 Pamphlet, 2000 / 070004 Pamphlet, 2009 / 146981 Pamphlet, 2000 / 70005 Pamphlet or 2013087366 Pamphlet (incorporated herein by reference). Some brands of fabric softeners suitable for use herein include, if desired, DOWNY, DOWNY ULTRA, DOWNY INFUSIONS, ALL, SNUGGLE, LENOR and GAIN. In some embodiments, liquid fabric softener products (e.g., as they exist prior to use in a laundry rinse cycle) can be formulated to contain one or more glucan ester derivatives. In some embodiments, the fabric softener can be in unit doses as disclosed herein for detergents.

[0188] The compositions disclosed herein that include at least one glucan ester derivative can be, for example, in the form of a dishwashing detergent composition or can include a dishwashing detergent composition. Examples of dishwashing detergents include detergents for automatic dishwashers (typically used in dishwashers) and hand dishwashing detergents. The dishwashing detergent composition can be, for example, in any dry or liquid / aqueous form disclosed herein. Components that can be included in some embodiments of the dishwashing detergent composition include, for example, phosphates; oxygen-based or chlorine-based bleaches; nonionic surfactants; alkaline salts (e.g., metasilicates; alkali metal hydroxides, sodium carbonate); any of the active enzymes disclosed herein; rust inhibitors (e.g., sodium silicate); antifoaming agents; additives for reducing the deceleration of the removal of luster and patterns from ceramics; fragrances; anti-caking agents (in granular detergents); starch (in tablet-based detergents); gelling agents (in liquid / gel-based detergents); and / or one or more of sand (in powdered detergents).

[0189] For example, dishwashing detergents such as detergents for automatic dishwashers or liquid dishwashing detergents contain: (i) nonionic surfactants present in an amount of 0 to 10% by weight, any ethoxylated nonionic surfactant, alkoxylated alcohol surfactant, epoxy-capped poly(oxyalkylated) alcohol or amine oxide surfactant; (ii) builders in the range of about 5 to 60% by weight, any phosphate builder (e.g., monophosphate, diphosphate, tripolyphosphate, other oligomeric polyphosphates, sodium tripolyphosphate - STPP), any phosphorus-free builder (e.g., methyl-glycine diacetic acid [MGDA] and their salts or derivatives, glutamine-N,N-diacetic acid [GLDA] and their salts or derivatives, iminodiacetic acid (IDS) and their salts or derivatives, carboxymethyl inulin and their salts or derivatives, nitrilotriacetic acid [NTA], diethylenetriaminepentaacetic acid [DTPA], B-alanine diacetic acid [B-ADA] and amino acid-based compounds containing their salts), homopolymers and copolymers of polycarboxylic acids and their partial or fully neutralized salts, monomeric polycarboxylic acids and hydroxycarboxylic acids in the range of 0.5% to 50% by weight and their salts or sulfonated / carboxylated polymers in the range of 0.1% to about 50% by weight; (iii) drying aids in the range of 0.1% to about 10% by weight (e.g., optionally another 3 to 6 functional groups - typically an acid, alcohol or ester functional group that induces polycondensation, together with a monomer, a polyester, especially an anionic polyester, polycarbonate-, polyurethane- and / or polyurea- polyorganosiloxane compounds or their, especially reactive cyclic carbonates and urea type precursor compounds); (iv) silicates in the range of about 1% to about 20% by weight (e.g., sodium or potassium silicate, e.g., disodium silicate, sodium metasilicate and crystalline phyllosilicate); (v) inorganic bleaching agents (e.g., perhydrate salts such as perborate, percarbonate, perphosphate, persulfate and persilicate) and / or organic bleaching agents (e.g., diacyl- and tetraacyl peroxides, especially organic peroxyacids such as diperoxydodecanedioic acid and diperoxyhexadecanedioic acid); (vi) bleach activators (e.g., 0.(i) an organic peracid precursor within the range of from 1% to about 10% by weight and / or a bleach catalyst (e.g., manganese triazacyclononane and related complexes; Co, Cu, Mn, and Fe bispyridylamine and related complexes; and pentaminecobalt(III) acetate and related complexes); (vii) a metal care agent within the range of from 0.1% to 5% by weight (e.g., benzotriazole, metal salts and complexes, and / or silicates); (viii) a glass corrosion inhibitor within the range of from about 0.1% to 5% by weight (e.g., salts and / or complexes of magnesium, zinc, or bismuth); and / or (ix) any active enzyme disclosed herein within the range of from about 0.01 to 5.0 mg per gram of the automatic dishwashing detergent composition, and an enzyme stabilizer (e.g., oligosaccharides, polysaccharides, and inorganic divalent metal salts). In some embodiments, the dishwashing detergent component or the entire composition (however, adapted to include glucan ester derivatives herein) can be as disclosed in U.S. Patent No. 8,575,083 or 9,796,951, or U.S. Patent Application Publication No. 2017 / 0044468, which are incorporated herein by reference.

[0190] The detergents herein for dish care, for example, can be included in unit doses (e.g., sachets or pouches) (e.g., water-soluble unit dose products), and can be made as described above for fabric care detergents, but rather can include a suitable dishwashing detergent composition.

[0191] It is contemplated that a number of commercially available detergent formulations can be adapted to include the glucan ester derivatives disclosed herein. Examples of commercially available detergent formulations include PUREX® ULTRAPACKS (Henkel), FINISH® QUANTUM (Reckitt Benckiser), CLOROX® 2 PACKS (Clorox), OXICLEAN MAX FORCE POWER PAKS (Church & Dwight), TIDE® STAIN RELEASE, CASCADE® ACTIONPACS, and TIDE® PODS™ (Procter & Gamble).

[0192] The compositions disclosed herein comprising at least one glucan ester derivative can be in the form of, for example, an oral care composition or can comprise an oral care composition. Examples of oral care compositions include dentifrices, toothpastes, mouthwashes, oral rinses, chewing gums, and edible strips that provide oral care in some form (e.g., treatment or prevention of dental caries [tooth decay], gingivitis, dental plaque, tartar, and / or periodontal disease). The oral care compositions can also be used for the treatment of "oral surfaces" that include all soft or hard surfaces within the oral cavity, such as the surface of the tongue, hard or soft palate, buccal mucosa, gingiva, and tooth surfaces. As used herein, "tooth surface" is, for example, the surface of a natural tooth or the hard surface of an artificial tooth such as a crown, cap, filling, bridge, denture, or dental implant.

[0193] The oral care compositions herein can comprise, for example, from about 0.01 to 15.0% by weight (e.g., from about 0.1 to 10% by weight or from about 0.1 to 5.0% by weight, from about 0.1 to 2.0% by weight) of the glucan ester derivatives disclosed herein. The glucan ester derivatives included in the oral care compositions can sometimes be provided as thickeners and / or dispersants in the compositions, which can be useful for imparting the desired consistency and / or mouthfeel to the compositions. The oral care compositions herein can also comprise one or more other thickeners or dispersants such as, for example, carboxyvinyl polymer, carrageenan (e.g., L-carrageenan), natural gums (e.g., karaya, xanthan, gum arabic, tragacanth), colloidal magnesium aluminum silicate, or colloidal silica.

[0194] The oral care compositions of the present specification can be, for example, toothpaste or other dentifrices. Such compositions of the present specification and any other oral care compositions can include, without limitation, one or more of a caries preventive agent, an antimicrobial or antibacterial agent, an anti-calculus or calculus preventive agent, a surfactant, an abrasive, a pH adjuster, a foaming regulator, a humectant, a flavoring agent, a sweetening agent, a pigment / colorant, a whitening agent, and / or other suitable ingredients. Examples of oral care compositions to which the glucan ester derivatives of the present specification can be added are disclosed in U.S. Patent Application Publication Nos. 2006 / 0134025, 2002 / 0022006, and 2008 / 0057007, which are incorporated herein by reference.

[0195] The caries preventive agent of the present specification can be an orally acceptable source of fluoride ions. Suitable sources of fluoride ions include, for example, fluoride compounds, monofluorophosphates, fluorosilicates, and amine fluorides including orafluor (N'-octadecyltrimethylenediamine-N,N,N'-tris(2-ethanol)-dihydrofluoride). The caries preventive agent can be present, for example, in an amount that provides a total of about 100 to 20,000 ppm, about 200 to 5,000 ppm, or about 500 to 2,500 ppm of fluoride ions in the composition. In an oral care composition where sodium fluoride is the sole source of fluoride ions, for example, an amount of sodium fluoride of about 0.01 to 5.0 wt%, about 0.05 to 1.0 wt%, or about 0.1 to 0.5 wt% can be present in the composition.

[0196] Antimicrobial or antibacterial agents suitable for use in the oral care compositions of this specification include, for example, phenolic compounds (e.g., p-hydroxybenzoic acid esters such as 4-allylcatechol, benzyl paraben, butyl paraben, ethyl paraben, methyl paraben and propyl paraben, 2-benzylphenol, butylated hydroxyanisole, butylated hydroxytoluene, capsaicin, carvacrol, creosol, eugenol, guaiacol, halogenated bisphenols such as hexachlorophene and bromochlorophene, 4-hexylresorcinol, 8-hydroxyquinoline and its salts, menthyl salicylate, salicylic acid esters such as methyl salicylate and phenyl salicylate, phenol, pyrocatechol, salicylanilide, thymol, halogenated diphenyl ether compounds such as triclosan and triclosan monophosphate), copper(II) compounds (e.g., copper(II) chloride, fluoride, sulfate and hydroxide), zinc ion sources (e.g., zinc acetate, citrate, gluconate, glycinate, oxide and sulfate), phthalic acid and its salts (e.g., magnesium monopotassium phthalate), hexetidine, octenidine, sanguinarine, benzalkonium chloride, domiphen bromide, alkylpyridinium chlorides (e.g., cetylpyridinium chloride, tetradecylpyridinium chloride, N-tetradecyl-4-ethylpyridinium chloride), iodine, sulfonamides, bisbiguanides (e.g., alexidine, chlorhexidine, chlorhexidine gluconate), piperidine derivatives (e.g., delmopinol, octapinol), magnolia extract, grape seed extract, rosemary extract, menthol, geraniol, citral, eucalyptol, antibiotics (e.g., augmentin, amoxicillin, tetracycline, doxycycline, minocycline, metronidazole, neomycin, kanamycin, clindamycin), and / or any antibacterial agent disclosed in U.S. Patent No. 5,776,435, which is incorporated herein by reference. One or more antimicrobial agents may optionally be present in the disclosed oral care compositions, for example, in an amount of about 0.01 to 10% by weight (e.g., 0.1 to 3% by weight).

[0197] Examples of suitable anti-calculus agents or calculus-preventing agents for use in the oral care compositions of the present specification include phosphates and polyphosphates (e.g., pyrophosphates), polyaminopropanesulfonic acid (AMPS), zinc citrate trihydrate, polypeptides (e.g., polyaspartic acid and polyglutamic acid), polyolefin sulfonates, polyolefin phosphates, diphosphonates (e.g., azacycloalkane-2,2-diphosphonates such as azacycloheptane-2,2-diphosphonic acid), N-methylazacyclopentane-2,3-diphosphonic acid, ethane-1-hydroxy-1,1-diphosphonic acid (EHDP), ethane-1-amino-1,1-diphosphonates and / or phosphonoalkanecarboxylic acids and salts thereof (e.g., their alkali metal salts and ammonium salts). Examples of useful inorganic phosphates and polyphosphates include monobasic, dibasic and tribasic sodium phosphates, sodium tripolyphosphate, tetrapolyphosphate, monosodium pyrophosphate, disodium, trisodium and tetrasodium pyrophosphate, disodium dihydrogen pyrophosphate, sodium trimetaphosphate, sodium hexametaphosphate or those in which the sodium is replaced with potassium or ammonium. Other useful anti-calculus agents in certain embodiments include anionic polycarboxylate polymers (e.g., polymers or copolymers of acrylic acid, methacrylic acid and maleic anhydride such as polyvinyl methyl ether / maleic anhydride copolymer). Still other useful anti-calculus agents include sequestering agents for metal ions such as hydroxycarboxylic acids (e.g., citric acid, fumaric acid, malic acid, tartaric acid and oxalic acid and salts thereof) and aminopolycarboxylic acids (e.g., EDTA). One or more anti-calculus agents or calculus-preventing agents may optionally be present in the disclosed oral care compositions, for example, in an amount of about 0.01 to 50% by weight (e.g., about 0.05 to 25% by weight or about 0.1 to 15% by weight).

[0198] Suitable surfactants for use in the oral care compositions of the present specification can be, for example, anionic, nonionic or amphoteric. Suitable anionic surfactants include, but are not limited to, water-soluble salts of C 8~20 alkyl sulfates, C 8~20Examples include sulfonated monoglycerides of fatty acids, sarcosinates, and taurates. Examples of anionic surfactants include sodium lauryl sulfate, sodium coconut oil monoglyceride sulfonate, sodium lauryl sarcosinate, sodium lauryl isethionate, sodium laures 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, derivatives of secondary and tertiary aliphatic amines having anionic groups such as carboxylates, sulfates, sulfonates, phosphates, or phosphonates, etc., C 8~20 derivatives of secondary and tertiary aliphatic amines of. An example of a suitable amphoteric surfactant is cocoamidopropyl betaine. One or more surfactants are optionally present in the disclosed oral care composition in a total amount of, for example, about 0.01 to 10% by weight (e.g., about 0.05 to 5.0% by weight or about 0.1 to 2.0% by weight).

[0199] Abrasives suitable for use in the oral care compositions herein include, for example, silica (e.g., silica gel, silicic acid, precipitated silica), alumina, insoluble phosphates, calcium carbonate, and resin abrasives (e.g., urea-formaldehyde condensation products). Examples of insoluble phosphates useful as abrasives herein are orthophosphates, polymetaphosphates, and pyrophosphates, which are dicalcium orthophosphate dihydrate, calcium pyrophosphate, β-calcium pyrophosphate, tricalcium phosphate, calcium polymetaphosphate, and insoluble sodium polymetaphosphate. One or more abrasives are optionally present in the disclosed oral care composition in a total amount of, for example, about 5 to 70% by weight (e.g., about 10 to 56% by weight or about 15 to 30% by weight). The average particle size of the abrasive in certain embodiments is about 0.1 to 30 μm (micrometers) (e.g., about 1 to 20 μm or about 5 to 15 μm).

[0200] In certain embodiments, the oral care composition may comprise at least one pH regulator. Such agents may be selected to acidify, make more basic, or buffer the pH of the composition to a pH range of about 2 to 10 (e.g., a pH range of about 2 to 8, 3 to 9, 4 to 8, 5 to 7, 6 to 10, or 7 to 9). Examples of pH regulators useful herein include, but are not limited to, carboxylic acids, phosphonic acids, and sulfonic acids; acid salts (e.g., sodium citrate monohydrate, disodium citrate); alkali metal hydroxides (e.g., sodium hydroxide, carbonates such as sodium carbonate, sodium bicarbonate, sesquicarbonates); borates; silicates; phosphates (e.g., monosodium phosphate, trisodium phosphate, pyrophosphates); and imidazole.

[0201] Suitable foaming regulators for use in the oral care compositions herein can be, for example, polyethylene glycol (PEG). For example, high molecular weight PEGs containing PEG having an average molecular weight of about 200,000 to 7,000,000 (e.g., about 500,000 to 5,000,000 or about 1,000,000 to 2,500,000) are suitable. One or more PEGs may optionally be present in the disclosed oral care compositions in a total amount of, for example, about 0.1 to 10 wt% (e.g., about 0.2 to 5.0 wt% or about 0.25 to 2.0 wt%).

[0202] In certain embodiments, the oral care composition may comprise at least one humectant. Humectants in certain embodiments can be polyhydric alcohols such as glycerin, sorbitol, xylitol, or low molecular weight PEG. The most preferred humectants can also function as sweeteners herein. One or more humectants may optionally be present in the oral care compositions disclosed herein in a total amount of, for example, about 1.0 to 70 wt% (e.g., about 1.0 to 50 wt%, about 2 to 25 wt%, or about 5 to 15 wt%).

[0203] Natural or artificial sweeteners can optionally be included in the oral care compositions of the present specification. 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 solid corn syrup), partially hydrolyzed starch, hydrogenated starch hydrolyzate, sorbitol, mannitol, xylitol, maltitol, isomalt, aspartame, neotame, saccharin and its salts, dipeptide-based intense sweeteners, and cyclamate. One or more sweeteners may optionally be present in the oral care compositions disclosed herein, for example, in a total amount of about 0.005 to 5.0% by weight.

[0204] In the oral care compositions of the present specification, natural or artificial flavoring agents may optionally be included. Examples of suitable flavoring agents include vanilla; sage; marjoram; Dutch celery oil; spearmint oil; cinnamon oil; wintergreen oil (methyl salicylate); peppermint oil; clove oil; bay oil; anise oil; eucalyptus oil; citrus oil; fruit oil; essential oils derived from lemon, orange, lime, grapefruit, apricot, banana, grape, apple, strawberry, cranberry or pineapple, etc.; flavorings derived from legumes or nuts such as coffee, cocoa, cola, peanut or almond; and adsorbed and encapsulated flavoring agents. Further included in the flavoring agents of the present specification are components that impart aroma and / or other sensory effects in the mouth, including, but not limited to, a cooling or warming effect. Such components include, but are not limited to, menthol, methyl acetate, menthyl lactate, camphor, eucalyptus oil, eucalyptol, anethole, eugenol, cassia, oxanone, Irisone®, propenylguaethol, 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 flavoring agents may optionally be present in the oral care compositions disclosed herein in a total amount of, for example, about 0.01 to 5.0% by weight (for example, about 0.1 to 2.5% by weight).

[0205] The oral care compositions in certain embodiments may contain at least one bicarbonate. For example, any orally acceptable bicarbonate including alkali metal bicarbonates such as sodium bicarbonate or potassium bicarbonate and ammonium bicarbonate can be used. One or more bicarbonates may optionally be present in the oral care compositions disclosed herein in a total amount of, for example, about 0.1 to 50% by weight (for example, about 1 to 20% by weight).

[0206] Oral care compositions in certain embodiments may include at least one whitening agent and / or colorant. Suitable whitening agents are peroxides such as those disclosed in U.S. Patent No. 8,540,971, which is incorporated herein by reference. Suitable colorants herein include, for example, chemicals that impart a specific luster or reflectance, such as pigments, dyes, lakes, and pearlescent agents. Specific examples of useful colorants herein include talc; mica; magnesium carbonate; calcium carbonate; magnesium silicate; magnesium aluminum silicate; silica; titanium dioxide; zinc oxide; red, yellow, brown, and black iron oxides; ferrous ammonium ferrocyanide compounds; manganese violet; ultramarine; titaniumated mica; and bismuth oxychloride. One or more colorants may optionally be present in the oral care compositions disclosed herein in a total amount of, for example, about 0.001 to 20 wt% (e.g., about 0.01 to 10 wt% or about 0.1 to 5.0 wt%).

[0207] Additional components that may optionally be included in the oral care compositions herein include, for example, one or more (as described above) enzymes, vitamins, and anti-adhesives. Examples of useful vitamins herein include vitamin C, vitamin E, vitamin B5, and folic acid. Examples of suitable anti-adhesives include solbrol, ficin, and quorum sensing inhibitors.

[0208] Further examples of personal care, household care, and other products and ingredients in this specification can be any of those disclosed in U.S. Patent No. 8,796,196, which is incorporated herein by reference. Examples of personal care, household care, and other products and ingredients in this specification include perfumes, fragrances, insect repellents and pesticides, foaming agents such as surfactants, pet pesticides, pet shampoos, disinfectants, hard surface (e.g., floors, tub / shower, sink, toilet, door handle / panel, glass / window, automobile / exterior or interior of an automobile) treatment agents (e.g., detergents, disinfectants and / or coating agents), wipes and other nonwoven materials, colorants, preservatives, antioxidants, emulsifiers, skin softeners, oils, pharmaceuticals, flavorants, and suspending agents.

[0209] The present disclosure also relates to a method of treating a material. The method includes contacting the material with an aqueous composition comprising at least one glucan ester derivative disclosed herein.

[0210] In the contacting method of the present specification, the material to be contacted with the aqueous composition may, in some embodiments, include a fabric. The fabrics herein may include natural fibers, synthetic fibers, semi-synthetic fibers, or any combination thereof. The semi-synthetic fibers herein are manufactured using materials of natural origin that have been chemically derivatized, and one example thereof is rayon. Non-limiting examples of the fabric types herein include: (i) cellulose fibers such as cotton (e.g., broadcloth, canvas, chambray, chenille, chintz, corduroy, cretonne, damask, denim, flannel, gingham, jacquard, knit, matelasse, oxford, percale, poplin, pique, satin, sarsaparilla, sheer, terry cloth, twill, velvet), rayon (e.g., viscose, modal, lyocell), linen, and Tencel®; (ii) proteinaceous fibers such as silk, wool, and related mammalian fibers; (iii) synthetic fibers such as polyester, acrylic, nylon, etc.; (iv) vegetable long fibers derived from jute, flax, ramie, coir, kapok, sisal, henequen, abaca, hemp, and sunn hemp; and (v) fabrics manufactured from any combination of the fabrics of (i) to (iv). Examples of fabrics including combinations of fabric types (e.g., natural and synthetic) include, for example, fabrics having both cotton fibers and polyester. Materials / articles including one or more fabrics herein include, for example, clothing, curtains, drapes, upholstery materials, carpets, bed sheets, bath linens, tablecloths, sleeping bags, tents, automotive interiors, etc. Other materials including natural and / or synthetic fibers include, for example, non-woven fabrics, waddings, papers, and foams.

[0211] The aqueous composition to be brought into contact with the fabric can be, for example, a fabric care composition (e.g., a laundry detergent, a fabric softener). Thus, the treatment method in a particular embodiment can be considered to be a fabric care method or a washing method when using a fabric care composition therein. The fabric care compositions herein provide the following fabric care benefits (i.e., surface direct effects): wrinkle removal, wrinkle recovery, wrinkle resistance, reduced fabric abrasion, fabric abrasion resistance, reduced fabric fuzzing, extended fabric life, fabric color maintenance, reduced fabric fading, reduced dye migration, fabric color restoration, reduced fabric soiling, fabric soil release, fabric shape retention, enhanced fabric smoothness, prevention of reattachment of soil onto the fabric, prevention of graying of the laundry, improvement of the fabric texture / handfeel and / or reduction of shrinkage.

[0212] Examples of the conditions (e.g., time, temperature, amount of washing / rinsing) for carrying out the fabric care method or washing method herein are disclosed in WO 97 / 03161 pamphlet 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 containing the fabric can be brought into contact with the aqueous composition herein at (i) a temperature of at least about 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110 or 120 minutes, (ii) at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90 or 95 °C (e.g., for laundry washing or rinsing, a "low" temperature of about 15 - 30 °C, a "medium" temperature of about 30 - 50 °C, a "high" temperature of about 50 - 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 in any combination of (i) - (iv).

[0213] The contacting step in a fabric care or laundering method can include, for example, any one of a washing step, a soaking step, and / or a rinsing step. Further, in another embodiment, the step of contacting a material or fabric can be carried out by any means known in the art, such as dissolving, mixing, shaking, spraying, treating, dipping, flash washing, injecting onto or into, binding, painting, coating, applying, adding, and / or causing an effective amount of the glucan ester derivative of the present specification to communicate with the fabric or material. In still further embodiments, the contacting can be used to treat the fabric to impart a substantial surface effect. As used herein, the term "fabric feel" or "hand" means the sensory reaction when a person touches the fabric, which can be physical, physiological, psychological, social, or any combination thereof. In one embodiment, the fabric feel can be measured using a PhabrOmeter® system (available from Nu Cybertek, Inc., Davis, CA) for measuring relative hand values (American Association of Textile Chemists and Colorists [AATCC test method, "202 - 2012, Relative Hand Value of Textiles: Instrumental Method"]).

[0214] In some embodiments of treating a material including a fabric, the glucan ester derivative of the aqueous composition adsorbs to the fabric. This feature is considered useful for the glucan ester derivative herein as an anti-redeposition agent and / or an anti-clouding agent in a fabric care composition (for example, in addition to its viscosity regulating effect). The anti-redeposition agent or anti-graying agent herein helps to prevent dirt from redepositing on the clothing in the wash water after the dirt has been removed. In some embodiments, the adsorption of the glucan ester derivative herein to the fabric is further contemplated to enhance the mechanical properties of the fabric.

[0215] The adsorption of the glucan ester derivative onto the fabric in this specification can be measured using a colorimetric method (for example, Dubois et al., 1956, Anal. Chem. 28: 350-356; Zemljic et al., 2006, Lenzinger Berichte 85: 68-76, both of which are incorporated herein by reference), or can be measured using any other method known in the art.

[0216] Other materials that can be contacted in the above treatment method include surfaces that can be treated with dishwashing detergents (for example, detergents for automatic dishwashers or hand dishwashing detergents). Examples of such materials include ceramic materials, porcelain, metals, glass, plastics (for example, polyethylene, polypropylene, polystyrene, melamine, etc.) and the surfaces of dishes, glasses, pots, pans, graters, cooking utensils and tableware made of wood (collectively referred to as "tableware" herein). Therefore, the treatment method in a particular embodiment can be regarded as, for example, a dishwashing method or a tableware cleaning method. Examples of the conditions (for example, time, temperature, cleaning volume) for implementing the dishwashing or tableware cleaning method of this specification are disclosed in this specification and in U.S. Patent No. 8,575,083 and U.S. Patent Application Publication No. 2017 / 0044468, which are incorporated herein by reference. In some aspects, the tableware product can be contacted with the aqueous composition of this specification under a suitable set of conditions such as any of the conditions disclosed above with respect to contacting a material including a fabric, for example.

[0217] As other materials that can be brought into contact in the above-described treatment method, oral surfaces such as soft or hard surfaces in the oral cavity are included, such as the surfaces of the tongue, hard palate and soft palate, buccal mucosa, gingiva and tooth surfaces (for example, hard surfaces of artificial teeth such as natural teeth or crowns, caps, fillings, bridges, dentures or dental implants, etc.). Therefore, the treatment method in certain embodiments can be regarded as, for example, an oral care method or a dental treatment method. The conditions (for example, time, temperature) for bringing the oral surface into contact with the aqueous composition of the present specification must be suitable for the purpose of use for such contact. Other surfaces that can be contacted in the treatment method also include outer skin surfaces, for example, skin, hair or nails (i.e., any keratin-containing tissue or keratin-containing material).

[0218] Therefore, some aspects of the present disclosure relate to materials containing the glucan ester derivatives of the present specification (for example, fabrics, or any other materials of the present specification such as fiber-containing products disclosed herein, or hair, skin, or other keratin-containing materials). Such materials can be produced, for example, according to the material treatment methods disclosed herein. In some aspects, the material can contain a glucan ester derivative when the glucan ester derivative is adsorbed on the surface of the material or otherwise in contact (for example, the glucan ester contained in the coating of the material).

[0219] Some aspects of the method for treating the materials of the present specification further include a drying step of drying the material after contacting it with the aqueous composition. The drying step can be carried out immediately after the contacting step or following one or more additional steps that may follow the contacting step (for example, drying of a fabric, dishware or hair after washing in the aqueous composition of the present specification, for example, rinsing with water). Drying can be carried out by air drying (for example, at about 20 - 25 °C) or by any of several means known in the art at a temperature of, for example, at least about 30, 40, 50, 60, 70, 80, 90, 100, 120, 140, 160, 170, 175, 180 or 200 °C, etc. The dried material herein typically contains less than 3, 2, 1, 0.5 or 0.1% by weight of moisture in the material.

[0220] The aqueous composition used in the processing method of this specification may be any aqueous composition disclosed in this specification. Examples of aqueous compositions include detergents (e.g., laundry detergents or dishwashing detergents), fabric softeners, water-containing dentifrices such as toothpaste, and hair care products such as hair styling, hair cleaning, or hair conditioning products.

[0221] Some aspects of this specification relate 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 the hair with a composition comprising the glucan ester derivative of this specification (e.g., coating), thereby providing treated (or coated) hair; and (b) shaping the treated (or coated) hair into a desired form; or (c) shaping the hair into a desired form; and (d) contacting the hair of step (c) with a composition comprising the glucan ester derivative of this specification (e.g., coating), thereby providing treated (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). may be included. Such a method can be arbitrarily characterized as a hair styling method. Contact in the hair styling method can be performed, for example, by applying / processing the hair with a hair styling composition (e.g., gel, mousse, spray) of the present specification containing at least one glucan ester derivative. In the hair styling method, the hair treated especially in step (a) or (d) can typically be wet or dry. The step (e) of removing the solvent can be performed by drying, such as the drying methods disclosed herein (e.g., air drying or blow drying by either room temperature or heated air). Drying can be performed, for example, while combing or brushing the treated hair (with or without stirring). Optionally, the styling method of the present specification can include a step of applying steam to the treated hair after step (b) or step (d) (but before an optional step [e]). The step (b) or (c) of shaping the hair can, in some embodiments, be performed by straightening the hair, curling it, or otherwise changing it to a form different from the form of the hair that existed before step (a), (b), or (c). The hair styled by the styling method of the present specification can, optionally, retain the desired form, for example, for a period of at least 1, 2, 3, 4, 5 days or more, without the need to apply any device and / or further material to the styled hair (i.e., while in a self-standing state). Such style retention can be, for example, in a state of dry air (e.g., relative humidity ≤ 50%) or wet air (e.g., relative humidity > 50%) (typically, during the period when the styled hair is not washed or rinsed).

[0222] In some embodiments, the materials that can be treated with the aqueous compositions (e.g., dispersions / emulsions) of the present specification are nonwoven products. This treatment can include the application of the aqueous compositions of the present specification (at any concentration disclosed herein), typically followed by a drying step (e.g., air drying, heat drying, vacuum drying; the drying temperature can be, for example, any suitable temperature disclosed herein), and can strengthen the nonwoven product (i.e., act as a binder therefor). In some embodiments, the glucan ester derivatives disclosed herein can increase the dry or wet tensile strength (measured in N / 5 cm) of the nonwoven fabric by, for example, about, or at least about, 1000%, 10000%, 100000%, or 1000000%. Accordingly, the present specification further provides a nonwoven product comprising a binder / reinforcer comprising the glucan ester derivative of the present disclosure. In some embodiments, the dry or wet tensile strength of the nonwoven fabric comprising the glucan ester derivative of the present specification 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 / 5 cm. Based on the total weight of the glucan ester derivative in the nonwoven material and the nonwoven product, the content of the glucan ester derivative therein can be about 1, 2, 5, 10, 15, 20, 25, 1 - 5, 1 - 10, 5 - 20, or 1 - 25 wt%. The nonwoven products of the present specification can be, for example, airlaid, drylaid, wetlaid, carded, electrospun, spunlace, spunbonded, or meltblown.In some embodiments, the nonwoven product can be a polishing or scouring sheet, an agricultural covering, an agricultural seed strip, a clothing lining, an automotive headliner or cover, a windshield cover, cheese wrap, a civil engineering fabric, a coffee filter, a cosmetic remover or applicator, a detergent pouch / sachet, a fabric softening sheet, an envelope, a face 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 wrap, a sanitary product (e.g., a sanitary pad / napkin, an underpad), an insulator, a label, a laundry aid, a medical care or physical injury care product (e.g., a band-aid, a cast padding or cover, a dressing, a pack, a sterilization packaging material, a sterilization package, a surgical drape, a surgical gown, a cotton swab), a mop, a napkin or paper towel, paper, a personal wipe or baby wipe, a reusable bag, a roofing undercover, a table linen, a tag, a tea or coffee bag, a cover, a vacuum cleaning bag or wallpaper. The fibers of the nonwoven product can, in some embodiments, contain cellulose and / or α-1,3-glucan, or can include one or more other materials disclosed herein that can be used to form the fibers. Examples of the nonwoven products, nonwoven product materials and / or methods of manufacturing nonwoven products and materials herein can be as described in U.S. Patent Application Publication Nos. 2020 / 0370216, 2018 / 0282918, 2017 / 0167063, 2018 / 0320291 or 2010 / 0291213, which are incorporated herein by reference.

[0223] The compositions herein comprising at least one glucan ester derivative of the present disclosure can be, for example, a film or a coating. The film or coating can, in some embodiments, be a dried film or coating containing, for example, less than about 3, 2, 1, 0.5, or 0.1 weight % water. In some embodiments, the film or coating can comprise about 20 - 40, 20 - 35, 20 - 30, 25 - 40, 25 - 35, or 25 - 30 weight % of the glucan ester derivative herein, and the balance of the materials in the film or coating is optionally water, an aqueous solution, and / or a plasticizer. The amount of the glucan ester derivative as presently disclosed in the films or coatings 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, 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 100 weight %. The films or coatings 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 weight % of the glucan ester) on a surface / object / material and then removing all or most (90, 95, 98, 99 weight % or more) of the water from the dispersion or solution, thereby producing the film or coating. The method is, for example, similar to or disclosed in U.S. Patent Application Publication No. 2018 / 0258590, which is incorporated herein by reference, and can be used to produce the film or coating.The basis weight of the coating comprising the glucan ester derivative of the present specification on the substrate can be, for example, 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).

[0224] The film or coating of the present specification 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 mils (1 mil = 0.001 inches). In some embodiments, such thickness is uniform, which can be characterized by having a continuous region that is (i) at least 20%, 30%, 40%, or 50% of the entire area of the film / coating and (ii) has a standard deviation of thickness of less than about 0.06, 0.05, or 0.04 mils. The film or coating of the present specification can be characterized as thin (e.g., < 2 mils) in some embodiments. The film of the present specification is typically a cast film.

[0225] The films or coatings of the present specification can exhibit various desired transparencies. For example, the film / coating can have high transparency (e.g., high light transmittance and / or low haze). As used herein, light transmissivity can refer to, for example, a film or coating that provides a light transmittance of at least about 10 - 99%, or at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98% or 99% light transmittance, and / or a haze of less than 30%, 25%, 20%, 15%, 10%, 5%, 2.5%, 2% or 1%. High light transmissivity can optionally refer to a film / coating having a light transmittance of at least about 90% and / or a haze of less than 10%. The light transmittance of the films / coatings of the present specification can be measured, for example, in accordance with the ASTM D1746 test (2009, Standard Test Method for Transparency of Plastic Sheeting, ASTM International, West Conshohocken, PA), which is incorporated herein by reference. The haze of the films / coatings of the present specification can be measured, for example, in accordance with the ASTM D1003 - 13 test (2013, Standard Test Method for Haze and Luminous Transmittance of Transparent Plastics, ASTM International, West Conshohocken, PA), which is incorporated herein by reference.

[0226] The films or coatings of the present specification can optionally further contain plasticizers such as glycerol, propylene glycol, ethylene glycol and / or polyethylene glycol. In some embodiments, other film components (in addition to the compositions of the present specification) are described 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.

[0227] A film or coating, or any suitable solid composition herein (e.g., composite, fiber, fibril) can, in some embodiments, further comprise at least one crosslinking agent. The glucan ester derivative molecules of the present disclosure are crosslinkable (covalently) with each other and / or with at least one other component of the composition (e.g., polymer, active agent) or, if the composition is applied to a substrate, with the components of the substrate. Moreover, in some embodiments, the glucan ester derivatives herein do not crosslink in any manner, but one or more other components of the composition do. Crosslinking can, for example, (i) enhance the tensile strength of a film or coating composition and / or (ii) plasticize it. In some embodiments, crosslinking can crosslink a film or coating to a substrate. In some cases, crosslinking agents such as di- or polycarboxylic acids, aldehydes or polyphenols can be used to impart plasticity and crosslinking characteristics to the substrate.Crosslinking agents suitable for preparing the compositions of this specification having crosslinks as described above include phosphoryl chloride (POCl3), polyphosphates, sodium trimetaphosphate (STMP), boron-containing compounds (e.g., boric acid, diborate, tetraborate, e.g., tetraboric acid decahydrate, pentaborate, polymeric compounds, e.g., Polybor®, alkali borates), polyvalent metals (e.g., titanium-containing compounds, e.g., titanium ammonium lactate, titanium triethanolamine, titanium acetylacetonate, or polyhydroxy complexes of titanium; zirconium-containing compounds such as zirconium lactate, zirconium carbonate, zirconium acetylacetonate, zirconium triethanolamine, zirconium lactate diisopropylamine, or polyhydroxy complexes of zirconium), glyoxal, glutaraldehyde, aldehydes, 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 ether itself, 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). Further other examples of suitable crosslinking agents are described in U.S. Patent No. 4,462,917, U.S. Patent No. 4,464,270, U.S. Patent No. 4,477,360 and U.S. Patent No. 4,799,550, and U.S. Patent Application Publication No. 2008 / 0112907, all of which are incorporated herein by reference. Moreover, in some embodiments, the crosslinking agent is not a boron-containing compound (e.g., as described above).The glucan ester derivative molecules of this specification can be cross-linked with any cross-linking agent or the like currently disclosed in other situations other than films or coatings (such as dispersions, fibers, fibrids, or other compositions disclosed herein).

[0228] To enhance the haptic of a film or coating, for example, one or more conditioning agents may be included in the coating film. The conditioning agent can be an anionic softening agent such as sulfated oil, soap, sulfated alcohol and / or oil emulsion; a cationic softening agent such as a quaternary ammonium compound; a nonionic softening agent such as a polyoxyethylene derivative, a polyethylene emulsion, a wax emulsion and / or a silicon softening agent; a natural fatty acid; an oil; a monoglyceride; a diglyceride; a polyglyceride; a citrate ester; a lactate ester; and / or a sugar ester such as a sucrose ester and / or a sorbitan ester.

[0229] Also disclosed are articles comprising an adhesive, film, coating, or binder comprising the glucan ester derivative of the present specification in dry form. Such articles (optionally "coated articles") include a substrate having at least one surface on which a coating, adhesive, film, or binder is disposed / deposited in a substantially continuous or discontinuous manner. In some embodiments, the article includes paper, leather, wood, metal, polymers, fibrous materials, masonry, drywall, gypsum, and / or architectural surfaces. "Architectural surface" as used herein is the external or internal surface of a building or other man-made structure. In some embodiments, the article includes a porous substrate such as paper, cardboard, paperboard, corrugated board, cellulose substrate, textile product, or leather. Additionally, in some embodiments, the article may include polymers such as polyamide, polyolefin, polylactic acid, polyethylene terephthalate (PET), poly(trimethylene terephthalate) (PTT), aramid, polyethylene sulfide (PES), polyphenylene sulfide (PPS), polyimide (PI), polyethylene imine (PEI), polyethylene naphthalate (PEN), polysulfone (PS), polyether ether ketone (PEEK), polyethylene, polypropylene, poly(cyclic olefin), poly(cyclohexylene dimethylene terephthalate), poly(trimethylene furandicarboxylate) (PTF), or cellophane. In some embodiments, an article comprising a fibrous substrate is a fiber, yarn, fabric, fabric blend, textile, non-woven fabric, paper, or carpet. The fibrous substrate may include natural and / or synthetic fibers such as cotton, cellulose, wool, silk, rayon, nylon, aramid, acetate, polyurethane urea, acrylic, jute, sisal, seaweed, coir, polyamide, polyester, polyolefin, polyacrylonitrile, polypropylene, polyaramid, or blends thereof.

[0230] The films, coatings or other compositions (e.g., composites) of this specification can, in some embodiments, have grease / oil and / or oxygen barrier properties. Such compositions can include, together with the glucan ester derivatives herein, one or more components as disclosed in U.S. Patent Application Publication No. 20190153674 or No. 20210095155, each incorporated herein by reference. For example, the films, coatings or other compositions of this specification can optionally include, as a binder, one or more of polyvinyl alcohol, polyvinyl acetate, partially saponified polyvinyl acetate, silanol-modified polyvinyl alcohol, butenediol 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, carrageenan, casein, soy protein, guar gum, synthetic polymer, styrene butadiene latex and / or styrene acrylate latex. In some embodiments, the composition for preparing the 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 a compound such as polyvinyl alcohol (or any other compound referenced 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 the glucan ester derivative disclosed herein. In some embodiments, the composition for preparing the 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 the binder or compound (e.g., any of the above compounds such as polyvinyl alcohol or starch) of this specification to the glucan ester derivative based on the respective wt% of these components in the composition.In some embodiments, the film, coating or other composition does not contain starch, but in other embodiments such as an oxygen barrier, starch may be included (e.g., as disclosed in U.S. Patent Application Publication No. 2011 / 0135912 or U.S. Patent No. 5621026 or U.S. Patent No. 6692801). The grease / oil barrier properties of the coating or film compositions herein can be evaluated using a standard “KIT” type test, for example, according to Technical Association of the Pulp and Paper Industry (TAPPI) Test Method T-559cm-02 (Grease resistance test for paper and paperboard, TAPPI Press, Atlanta, GA, USA; incorporated herein by reference). In this test, good grease / oil barrier / resistance function is indicated by a value closer to 12 on a scale of 1 to 12. The grease / oil barrier properties as well as the water / aqueous liquid barrier properties can be evaluated by the Cobb test, if desired. The barriers 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 compositions 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.OTR can be determined, for example, under relative humidity conditions of about 50% - 80%, 30% - 55%, 35% - 50% or 30% - 80% and / or at a temperature of about or at least about 15, 20, 25, 30, 35, 40, 45, 15 - 40, 15 - 35, 15 - 30, 15 - 25, 20 - 40, 20 - 35, 20 - 30 or 20 - 25 °C. Examples of substrates of the present specification that can utilize a grease / oil and / or oxygen barrier coating include substrates including cellulose (e.g., paper, cardboard, paperboard, corrugated board, textile), polyethylene, polypropylene, polylactic acid, poly(ethylene terephthalate) (e.g., MYLAR), poly(trimethylene terephthalate), polyamide, polybutylene succinate, polybutylene adipate terephthalate, polybutylene succinate adipate, poly(trimethylene furandicarboxylate), synthetic and / or petroleum-based substrates or bio-based substrates. Any of the above films, coatings or other compositions can be in the form of, for example, laminates or extruded articles and are optionally located on any of the above substrates.

[0231] Films, coatings, or other compositions (e.g., dispersions, foams, masterbatches, composites) containing the glucan ester derivatives herein can, in some embodiments, further comprise a polyurethane (e.g., any of those disclosed herein). Such compositions can, for example, contain from 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 weight % of the glucan ester derivatives herein, with the balance being composed of all or most (e.g., more than 90% or 95%) of one or more polyurethanes. Such compositions can be wet (e.g., a dispersion of the glucan ester derivative and the polyurethane) or dry (e.g., a masterbatch, film / coating, laminate, foam, or extruded composite of the glucan ester derivative and the polyurethane). The polyurethane can, herein, 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. Such compositions can, in some instances, be subject to hydrolytic aging (e.g., exposed to 2 - 4 or 3 days, 45 - 55 or about 50 °C and / or 90 - 98% or about 95% relative humidity). In some embodiments, the polyurethane compositions containing the glucan ester derivatives herein can be heat and / or pressure treatable, and the application of heat and / or pressure for pressing, molding, extrusion, or any other related processing step can be, for example, at about or at least about 90, 95, 100, 105, 110, 115, 120, 130, 140, 95 - 115, or 100 - 110 °C, and / or at least about 5000, 10000, 15000, 20000, or 25000 psi of pressure. Such application of heat and / or pressure can be, for example, for at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, or 30 minutes.Compression-molded polyurethane compositions in some embodiments, such as films, can be approximately or at least approximately 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99% or 100% transparent or translucent. In some embodiments, any polyurethane composition of the present disclosure can be produced by a method comprising providing an aqueous polyurethane dispersion and mixing a glucan ester derivative of the present specification with the polyurethane dispersion. The resulting aqueous composition can be used directly to produce a composition (e.g., a film or coating), or it can be dried to a masterbatch that is then used to prepare the composition (e.g., by melt-processing).

[0232] Films or coatings in some embodiments can be in the form of edible films or coatings. Such materials can, in some embodiments, include the glucan ester derivatives herein and one or more components described in U.S. Patent Nos. 4,710,228; 4,543,370; 4,820,533; 4,981,707; 5,470,581; 5,997,918; 8,206,765; or 8,999,413, or U.S. Patent Application Publication No. 2005 / 0214414. In some embodiments, the glucan ester derivatives herein optionally replace starch and / or starch derivatives in the edible film or coating as disclosed in any of the foregoing references. Edible films or coatings can be, for example, on potato products (e.g., potato strips such as French fries), other vegetables or vegetable products (e.g., zucchini, pumpkin, sweet potato, onion, okra, chili pepper, green bean, tomato, cucumber, lettuce, cabbage, carrot, broccoli, cauliflower, Brussels sprouts, bean sprouts, onion, any fresh cut of vegetables), mushrooms, fruits (e.g., berries such as raspberries, strawberries or blueberries, avocado, kiwi, kumquat, orange, tangerine, apple, pear, banana, grapefruit, cherry, papaya, lemon, lime, mango, peach, cantaloupe, any fresh cut of fruits) and / or nuts (peanut, walnut, almond, pecan, cashew, hazelnut, Brazil nut, macadamia). For example, where appropriate, any other foods disclosed herein can also have an edible coating. These and other foods having the edible films or coatings herein can, in some embodiments, be fried or baked, and / or the film or coating provides softness, moisture retention, protection from moisture, crispness, dietary fiber (instead of digestible starch), oxygen barrier, freshness and / or anti-ripening properties.In some embodiments, anti-ripening is measured by the degree to which the coating reduces the release of gaseous ripening hormones such as ethylene by plant-based products (e.g., at 15 - 30, 15 - 25, or 20 - 25 °C) (e.g., by at least 25%, 50%, 75%, 80%, 85%, or 90%) and / or the degree to which softening and / or sweetening of the plant product is reduced by the coating. In some embodiments, the edible coating can be prepared by applying an aqueous dispersion or solution containing the glucan ester derivatives of the present specification (e.g., 5 - 15, 5 - 12, 5 - 10, 7.5 - 15, 7.5 - 12, or 7.5 - 10 wt% in water) to the food and drying the dispersion or solution (e.g., by air drying, forced air drying, vacuum drying, and / or heating).

[0233] In some embodiments, the coating composition that can be used to prepare the coatings of the present specification can include any of the above components / materials / formulations. In some embodiments, the coating composition is a latex composition such as those described below.

[0234] The compositions of the present specification containing at least one glucan ester derivative of the present disclosure can, in some embodiments, be latex compositions. Examples of the latex compositions of the present specification include paints (e.g., primers, finishes / decorative), adhesives, films, coatings, and binders. The formulations and / or components of the latex compositions in the present specification (in addition to the compositions of the present specification) can be described, for example, in 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, which are hereby incorporated by reference.

[0235] The glucan ester derivatives 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%, 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% based on the weight of all the dispersed solids of the latex.

[0236] Some embodiments of the latex composition can include a polymer, polyurethane, epoxy and / or rubber elastomer polymerized from at least one ethylenically unsaturated monomer (e.g., a monoethylenically unsaturated monomer). Examples of monoethylenically unsaturated monomers herein include vinyl monomers, acrylic monomers, allyl monomers, acrylamide monomers, monocarboxyl unsaturated acids and dicarboxyl unsaturated acids.

[0237] Examples of suitable vinyl monomers of the polymer in the latex composition of the present specification include any compound having vinyl functionality (i.e., ethylenically unsaturated), 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, methylstyrene and similar lower alkyl styrenes, chlorostyrene, vinyltoluene, vinylnaphthalene, divinylbenzene), vinyl aliphatic hydrocarbons (e.g., vinyl chloride, vinylidene chloride, alpha olefins such as ethylene, propylene and isobutylene, conjugated dienes such as 1,3-butadiene, methyl-2-butadiene, 1,3-piperylene, 2,3-dimethylbutadiene, isoprene, cyclohexene, cyclopentadiene and dicyclopentadiene) and vinyl alkyl ethers (e.g., methyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether), but compounds having acrylic functionality (e.g., acrylic acid, methacrylic acid, esters of such acids, acrylonitrile, acrylamide) are excluded. In some embodiments, the latex composition of the present specification comprises a vinyl acetate-ethylene copolymer, a carboxylated vinyl acetate-ethylene copolymer and / or polyvinyl acetate.

[0238] Examples of suitable acrylic monomers of the polymer in the latex composition of this specification include alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, aromatic derivatives of acrylic and methacrylic acids, acrylamide and acrylonitrile. Typically, alkyl acrylate and methacrylate monomers (also called alkyl esters of acrylic acid or methacrylic acid) have an alkyl ester moiety containing 1 to about 18 carbon atoms per molecule or 1 to about 8 carbon atoms per molecule. Suitable acrylic monomers include, for example, methyl acrylate and methacrylate, ethyl acrylate and methacrylate, butyl acrylate and methacrylate, propyl acrylate and methacrylate, 2-ethylhexyl acrylate and methacrylate, cyclohexyl acrylate and methacrylate, decyl acrylate and methacrylate, isodecyl acrylate and methacrylate, benzyl acrylate and methacrylate, isobornyl acrylate and methacrylate, neopentyl acrylate and methacrylate, and 1-adamantyl methacrylate. If acid functionality is desired, acids such as acrylic acid or methacrylic acid can also be used.

[0239] Some embodiments of the latex composition include a polyurethane polymer. Examples of suitable polyurethane polymers are those that include 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 can include 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 polyurethanes herein can be formed as the reaction product of a polyol, such as 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, or tetraethylene glycol, and 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 aromatic and aliphatic groups.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-p-xylene, 1,3-diisocyanato-m-xylene, 2,4-diisocyanato-1-chlorobenzene, 2,4-diisocyanato-1-nitrobenzene, 2,5-diisocyanato-1-nitrobenzene, m-phenylene diisocyanate, hexahydrotoluene diisocyanate, 1,5-naphthalene diisocyanate, 1-methoxy-2,4-phenylene diisocyanate, 4,4'-biphenylmethane diisocyanate, 4,4'-biphenylene diisocyanate, 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate, 3,3'-4,4'-diphenylmethane diisocyanate, and 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate. Also, for example, polyisocyanate homopolymers containing allophanate, biuret, isocyanurate, iminooxadiazinedione, or carbodiimide groups are also useful herein.The polyols of the present specification can be any polyol containing two or more hydroxy groups, such as C2-C12 alkanediols, 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-octanetriol, chloropentanediol, glycerol monoalkyl ether, glycerol monoethyl ether, diethylene glycol, 1,3,6-hexanetriol, 2-methylpropanediol, 2,2,4-trimethyl-1,3-pentanediol, cyclohexanedimethanol, polymeric polyols such as polyether polyols or polyester polyols. In some embodiments, the polyols of the present specification can be poly(oxytetramethylene) glycol, polyethylene glycol, or poly 1,3-propanediol. The polyols of some embodiments can be polyester polyols such as those produced by transesterification of aliphatic diacids with aliphatic diols. Suitable aliphatic diacids include, for example, C3-C10 diacids, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid. In some embodiments, aromatic and / or unsaturated diacids can also be used to form the polyester polyol.

[0240] Some embodiments of the latex composition include an epoxy polymer / resin (polyepoxide), such as bisphenol A epoxy resin, bisphenol F epoxy resin, Novolac epoxy resin, aliphatic epoxy resin or glycidylamine epoxy resin.

[0241] Some embodiments of the latex composition include a rubber elastomer. In some embodiments, the rubber elastomer can include one or more diene-based sulfur-vulcanizable elastomers having a glass transition temperature (Tg) of less than -30 °C, as determined, for example, by dynamic mechanical analysis. In further examples, the rubber elastomers herein include, for example, natural rubber, synthetic polyisoprene, polybutadiene rubber, styrene / butadiene copolymer rubber, ethylene propylene diene monomer rubber, hydrogenated nitrile butadiene rubber, neoprene, styrene / isoprene / butadiene terpolymer rubber, butadiene / acrylonitrile rubber, polyisoprene rubber, isoprene / butadiene copolymer rubber, nitrile rubber, ethylene-acrylic rubber, butyl and halobutyl rubber, chlorosulfonated polyethylene, fluoroelastomer, hydrocarbon rubber, polybutadiene or silicone rubber.

[0242] The liquid component of the latex composition herein can be water or an aqueous solution. The aqueous solution of some embodiments 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.

[0243] In some embodiments, the latex composition of the present specification may further include one or more additives. Examples of the additives of the present specification include dispersants, rheology aids, defoamers, foaming agents, adhesion promoters, flame retardants, bactericides, fungicides, preservatives, optical brighteners, fillers, anti-settling agents, fusing agents, wetting agents, buffers, pigments / colorants (e.g., metal oxides, synthetic organic pigments, carbon black), viscosity modifiers, antifreezing agents, surfactants, binders, crosslinking agents, corrosion inhibitors, curing agents, pH adjusters, salts, thickeners, plasticizers, stabilizers, extenders, and matting agents. Examples of the pigments of the present specification include titanium dioxide (TiO2), calcium carbonate, diatomaceous earth, mica, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silica, talc, zinc oxide, aluminum silicate, nepheline syenite, and mixtures thereof. In some embodiments, the latex composition essentially does not contain starch, starch derivatives (e.g., hydroxyalkyl starch), cellulose, and / or cellulose derivatives (e.g., carboxymethyl cellulose) (e.g., components less than 1, 0.5, 0.1, or 0.01 wt%).

[0244] The latex compositions in the form of paints or other colorants of this specification can, in some embodiments, have a pigment volume concentration (PVC) of about 3% to about 80%. By way of example, a flat paint can have a PVC in the range of about 55 to 80%, a primer or an undercoat can have a PVC in the range of about 30 to 50%, and / or a gloss colored paint can have a PVC in the range of about 3 to 20%. The paints or other colorants of some embodiments 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 values of this specification can be those of a specific pigment (or mixture of pigments), such as those disclosed above (e.g., titanium dioxide). The compositions of the present disclosure provide one or more physical properties to the latex composition (e.g., for use as a paint or other colorant): for example, opacity, reduction in the pigments required, increase in hardness, reduction in tack, reduction in gloss (i.e., resulting in a matte effect), increase in shear strength, better abrasion resistance, improvement in drying time, improvement in fade resistance, reduction in blistering and / or an improved handle (a less sticky feel) as compared to a latex composition that differs only by not including the compositions of the present disclosure.

[0245] The latex compositions herein can be applied to the substrate (as above) of the article using any method known in the art. Typically, after application of the latex composition, at least a portion of the aqueous solution is removed, for example, by drying, to provide an adhesive, film, coating or binder comprising the latex composition in a dry or semi-dry form. Suitable application methods include air knife coating, rod coating, bar coating, wire bar coating, spray coating, brush coating, cast coating, flexible blade coating, gravure coating, jet applicator coating, short dwell coating, slide hopper coating, curtain coating, flexographic printing coating, size-press coating, reverse roll coating and transfer roll coating. The latex composition can be applied onto at least a portion of the substrate, and can be, for example, one or more coats / applications.

[0246] Some aspects of the present specification relate to compositions containing pigments. The composition containing a pigment can be in a liquid state (e.g., the aqueous or non-aqueous compositions of the present specification) or in a solid state (e.g., the dry compositions of the present specification). Examples of compositions containing pigments include compositions such as those disclosed in other parts of the present specification (e.g., paints, primers, colorants), inks, dyes (e.g., food coloring dyes, fabric coloring dyes), resins, sunscreens, and cosmetics (e.g., mascara, blush, nail varnish / gloss enhancer, lipstick, gloss, eyeliner, foundation, eyeshadow, skin decorative compositions). The pigments of the composition containing a pigment can be, for example, any of the pigments of the present specification. Examples of pigments for these and / or other aspects of the present specification 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, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, and / or quinophthalone compounds. Further examples of pigments useful in the present specification are disclosed in U.S. Patent Application Publication No. 2006 / 0085924, which is incorporated herein by reference.

[0247] The compositions herein comprising at least one glucan ester derivative of the present disclosure can be in the form of a composite (e.g., a rubber composite or a polyurethane composite) as disclosed in U.S. Patent Application Publication No. 2019 / 0225737, No. 2017 / 0362345, or No. 2020 / 0181370, all of which are hereby incorporated by reference herein. The composites of the present disclosure can optionally be described as comprising at least one polymer in addition to the glucan ester derivative of the present disclosure. One or more of the above components of the latex composition (e.g., rubber or polyurethane) can optionally be additional polymers in such composites. The additional polymers of the composites 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 disclosed above with respect to the latex components.

[0248] Rubbers in some embodiments can be, 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 butadiene rubber, silicone rubber or neoprene, or more than one of them. Examples of composites containing the rubber herein include tires (e.g., automotive / bicycle; pneumatic tires; including tire treads and / or sidewalls), belts (e.g., conveyor belts, power transmission belts), hoses, gaskets, footwear (e.g., shoes, sneakers, boots; soles, cushions and / or aesthetic features), coatings, films and adhesives. The rubber composites herein are typically vulcanized. In some embodiments, including the composition herein in a composite containing 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, lightweight and / or mechanical strength) compared to using current fillers such as carbon black or silica; such performance enhancements can, in some embodiments, be due to the tire. In some embodiments, 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 weight percent of a filler (e.g., carbon black or silica) typically currently used in rubber composites such as tires. Note that currently commercially available rubber composite tires (not including the composition herein) typically contain up to about 30 weight percent of existing fillers such as carbon black. Thus, rubber composites such as tires herein can contain, for example, about or at least about 5, 10, 15, 20, 25, or 30 weight percent of the composition of the present disclosure. The rubber composition herein, in some embodiments, has a low minimum elastic torque (M L )(e.g., about 0.10, 0.08, 0.06, 0.04, 0.03 or 0.02 dNm [decinewton-meter] or less), and a method of mixing the rubber composition during its preparation is disclosed.

[0249] A composition comprising at least one glucan ester derivative of the present disclosure can be a paper / packaging composition or a cellulose fiber-containing composition. Examples of such compositions are any kind of paper / packaging or cellulose fiber-containing composition disclosed herein, such as paper (e.g., writing paper, office paper, copy paper, kraft paper), cardboard, paperboard, corrugated paper, tissue paper, napkin / paper towel, wipe, or non-woven fabric. The formulations and / or components of the paper / packaging compositions or cellulose fiber-containing compositions herein (in addition to the glucan ester derivatives herein), and the forms of these compositions can be as described, for example, in U.S. Patent Application Publication Nos. 2018 / 0119357, 2019 / 0330802, 2020 / 0062929, 2020 / 0308371, or 2020 / 0370216 (which are hereby incorporated by reference in their entirety). In some embodiments, the glucan ester derivative functions as a strengthening aid in paper or other cellulose fiber-containing compositions. The ability of the glucan ester derivative to agglomerate fibers and / or other insoluble materials in the papermaking process (e.g., pulp flocculation) is considered a means by which the glucan ester derivatives herein can be incorporated into paper or other products involving flocculation in their manufacture. However, in some embodiments, the glucan ester derivatives herein can be added as a component of any of the aforementioned compositions, regardless of their possible addition as a flocculation aid.

[0250] Some aspects of the present disclosure relate to a method of aggregation or dehydration comprising: (a) mixing at least one glucan ester derivative of the present specification into an aqueous composition comprising suspended solids / particles, whereby at least a portion of the suspended solids / particles becomes aggregated; and (b) optionally separating the aggregated solids / particles from the aqueous composition in step (a). Accordingly, the glucan ester derivatives in some aspects can be characterized, for example, as flocculants, dehydrating agents, clarifying agents, and / or clouding agents. The aggregated particles of the treated composition typically sediment (coagulate) or are otherwise more susceptible to separation procedures (e.g., filtration). Soluble glucan ester derivatives can be used in the flocculation method, although in some aspects insoluble glucan ester derivatives can be used. Typically, the glucan ester derivatives of the present specification for flocculation applications are (i) biodegradable and / or (ii) not crosslinked.

[0251] One, two, three, or more different types of glucan ester derivatives herein can be used, for example, in a flocculation method. In some aspects, the glucan ester derivative is the only flocculant used, although in other aspects the glucan ester derivative is used in addition to another type of flocculant (e.g., an existing commercially available flocculant 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 90 weight percent of all the flocculants added to the aqueous composition.

[0252] The amount of glucan ester derivative mixed in step (a) in an aqueous composition comprising suspended solids / particles 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 per kg of suspended solids (on a dry solids basis). It will be understood that water-soluble glucan ester derivatives are typically dissolved in the aqueous composition after the mixing step (a). Mixing can be performed by any standard means.

[0253] The temperature and pH of the aqueous composition having suspended solids treated with the glucan ester derivative can be any temperature and pH disclosed herein in the aqueous composition. In some embodiments, 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, 1 - 70, 1 - 60, 1 - 50, 1 - 40, 1 - 30, 5 - 80, 5 - 70, 5 - 60, 5 - 50, 5 - 40, 5 - 30, 15 - 80, 15 - 70, 15 - 60, 15 - 50, 15 - 40, or 15 - 30 °C. When the glucan ester derivative is added to and mixed with the aqueous composition, sedimentation of the suspended solids can start, for example, at about or at least about 0.5, 1, 2, 3, 4, 5, 6, 9, 12, 18, 24, 30, 36, 42, or 48 hours, etc.

[0254] In some embodiments, the percentage of the initially suspended solids that sediment (i.e., are no longer suspended) after treatment with the glucan ester derivative is about or at least about 30, 40, 50, 60, 70, 80, 90, 95, 96, 97, 98, 99, or 100 weight %. Typically, the flocculants herein enable the sedimented particles to occupy less space. For example, the total volume of the sedimented particles after treating an aqueous composition (initially having suspended particles) with the glucan ester derivative herein can be about 90%, 80%, 70%, 60% or 50%, or about less than that of the total volume of the sedimented particles that sediment in the aqueous composition without the aid of the flocculant (all other conditions of each system being the same). The sedimentation volume can be determined using any suitable method, such as the method described in the following examples.

[0255] In some embodiments, the turbidity (i.e., the quality of a turbid, opaque, and / or thick liquid with suspended solids / particles), color, and / or opacity of an aqueous composition having 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% when treated with the glucan ester derivatives of the present specification. Turbidity can be measured, for example, in nephelometric turbidity units (NTU). Any suitable method can be used to measure turbidity, such as the methodology disclosed in Progress in Filtration and Separation (Edition: 1, Chapter 16. Turbidity: Measurement of Filtrate and Supernatant Quality?, Publisher: Academic Press, Editors: E.S. Tarleton, July 2015), which is incorporated herein by reference, or as described in the following examples. In the present specification, any suitable method, such as spectrophotometric colorimetry or photoelectric colorimetry, can be used to measure the color of a liquid.

[0256] In some embodiments, the filterability of an aqueous composition having suspended solids / particles can be improved / increased when treated with the glucan ester derivatives of the present specification. The filterability of a liquid composition can be measured using any suitable method, such as measuring the capillary suction time. In some embodiments, the capillary suction time (e.g., measured in seconds) of an aqueous composition having suspended solids / particles can be reduced by about or at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 85% when treated with the glucan ester derivatives of the present specification. Any suitable method can be used to measure the capillary suction time of a liquid.

[0257] The suspension particles that can be subjected to aggregation herein are typically colloidal particles (i.e., undissolved particles [solids] that are stably suspended). Thus, the aqueous compositions that can be subjected to the aggregation methods herein can be, for example, colloidal. Aqueous compositions containing suspended solids / particles that can be treated with the flocculants of the present disclosure include, for example, wastewater (e.g., municipal, industrial, agricultural), drainage / sewage, sludge (e.g., activated sludge), water from a body of water (e.g., river / creek, canal, pond, lake, sea), pool water, cooling water, sediment (e.g., clay sediment) and / or water containing soil, water treated for drinking, or water containing fibers and / or fillers as present in a papermaking process (e.g., pulp flocculation). Examples of industrial wastewater are from a paper mill or a drilling / mining operation. In some embodiments, the suspended solids can include microbial cells (living and / or dead), such as bacteria, yeast, and / or algae. The aggregation herein is considered applicable to aqueous compositions present during food or beverage production processes, such as brewing (e.g., wort after fermentation), cheese curd formation, or soybean curd (tofu) production. Systems / operations that can incorporate the disclosed aggregation methods include, for example, wastewater / drainage / sludge treatment, papermaking, water purification, soil conditioning, and / or mining / drilling / underground operations, or any other system / operation that uses aggregation.

[0258] The aggregation methods herein optionally further include the step of separating the aggregated solids / particles from the treated aqueous composition. Such steps can include, for example, sedimentation / sediment, filtration, centrifugation, and / or decantation.

[0259] The present disclosure also relates to a method of producing a solid composition comprising at least one glucan ester derivative herein. Such a method can 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 herein, (b) forming the aqueous composition into a desired form (e.g., fiber, fibrid, film / coating, composite, extrusion), and (c) removing liquid / solvent from the aqueous composition of step (b) to produce a solid composition comprising the glucan ester derivative. In some embodiments, the ester derivative is of a glucan herein that, as underivatized, is insoluble under non-caustic aqueous conditions (e.g., α-1,3-glucan with DP>8 or >9).

[0260] In some embodiments where the non-caustic aqueous composition is a solution and the ester derivative is of a glucan herein that is insoluble under non-caustic aqueous conditions as underivatized, the liquid / solvent can be removed by raising the pH of the solution to greater than about 10, 10.5, 11, 11.5 or 12, thereby precipitating the dissolved glucan esters from the solution. The pH of the solution can be raised, for example, by adding / mixing a base (e.g., a metal hydroxide such as NaOH) to the solution. The precipitated glucan ester derivative in the desired form / shape from step (b) can optionally be washed with an organic liquid, such as, for example, an alcohol (e.g., methanol, ethanol, isopropanol), and / or dried. The concentration of glucan ester derivative in the solution provided in step (a) can be 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% by weight, as disclosed elsewhere herein.

[0261] The present disclosure also relates to solid compositions produced by the aforementioned processes. Such compositions may be, for example, fibers, fibrids, films / coatings, composites, or extrusions.

[0262] Non-limiting examples of the compositions and methods disclosed herein include the following: 1. A composition comprising an ester derivative of glucan (glucan ester derivative), wherein the glucan has a degree of substitution (DoS) of up to about 3.0 with at least two organic groups individually ester-bonded to the glucan, (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, the composition comprising an ester derivative of glucan (glucan ester derivative). 2. The composition according to embodiment 1, wherein the glucan is an α-glucan. 3. The composition according to embodiment 2, wherein at least about 50% of the glycosidic bonds of the α-glucan are α-1,3 bonds. 4. The composition according to embodiment 2, wherein at least about 50% of the glycosidic bonds of the α-glucan are α-1,6 bonds, and optionally, the α-glucan comprises at least 1% α-1,2 and / or α-1,3 branches. 5. The composition according to embodiment 1, wherein the glucan is a beta-glucan (e.g., at least about 50% of the glycosidic bonds of β-glucan are β-1,3 bonds or β-1,4 bonds). 6. The composition according to embodiment 1, 2, 3, 4, or 5, wherein the glucan has a weight average degree of polymerization (DPw) of at least 6. 7. The composition according to embodiment 1, 2, 3, 4, 5 or 6, wherein the DoS is at least about 0.005 with at least two organic groups. 8. The composition according to embodiment 1, 2, 3, 4, 5, 6 or 7, wherein the DoS is about 0.005 to about 1.5 with at least two organic groups. 9. The composition according to embodiment 1, 2, 3, 4, 5, 6, 7 or 8, wherein the DoS is about 0.005 to about 1.5 with the cationic organic group. 10. The composition according to embodiment 1, 2, 3, 4, 5, 6, 7, 8 or 9, wherein the DoS is about 0.005 to about 1.0 with the cationic organic group. 11. The composition according to embodiment 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, wherein the DoS is about 0.005 to about 0.5 with the cationic organic group. 12. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, wherein the DoS is from about 0.005 to about 0.1 with a cationic organic group. 13. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, wherein the DoS is from about 0.04 to about 0.1 with a cationic organic group. 14. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, wherein the DoS is from about 0.005 to about 1.5 with a hydrophobic organic group. 15. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, wherein the DoS is from about 0.005 to about 1.0 with a hydrophobic organic group. 16. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, wherein the DoS is from about 0.005 to about 0.5 with a hydrophobic organic group. 17. The composition according to any one of Embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, wherein the DoS is from about 0.4 to about 1.0 with a hydrophobic organic group. 18. The cationic organic group has the structure:

Chemical formula

Chemical formula

[0263] Non-limiting examples of the compositions and methods disclosed herein include the following: 1b. A composition comprising an ester derivative of glucan having a degree of substitution (DoS) of up to about 3.0 with at least one cationic organic group (cationic acyl group) ester-bonded to the glucan. 2b. The composition of embodiment 1b, wherein the glucan is α-glucan. 3b. The composition of embodiment 2b, wherein at least about 50% of the glycosidic linkages of the α-glucan are α-1,3 linkages. 4b. The composition of embodiment 2b, wherein at least about 50% of the glycosidic linkages of the α-glucan are α-1,6 linkages and optionally the α-glucan comprises at least 1% α-1,2 and / or α-1,3 branching. 5b. The composition of embodiment 1b, wherein the glucan is β-glucan. 6b. The composition of embodiment 5b, wherein at least about 50% of the glycosidic linkages of the β-glucan are β-1,3 or β-1,4 linkages. 7b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, or 6b, wherein the glucan has a weight average degree of polymerization (DPw) of at least 6. 8b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, or 7b, wherein the DoS with the cationic organic group is at least about 0.005. 9b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b, or 7b, wherein the DoS with the cationic organic group is at least about 0.3. 10b. The composition of embodiment 1b, 2b, 3b, 4b, 5b, 6b or 7b, wherein the DoS with the cationic organic group is from about 0.3 to about 2.0. 11b. The cationic organic group has the structure:

Chemical formula

Chemical formula

Examples

[0264] The present disclosure is further illustrated in the following examples. These examples illustrate specific aspects herein, but it should be understood that they are shown for illustrative purposes only. From the foregoing discussion and these examples, those skilled in the art can identify the essential features of the embodiments disclosed herein and make various changes and modifications to adapt the embodiments disclosed herein to various uses and conditions without departing from the spirit and scope of the invention.

[0265] Materials / Methods Preparation of Representative α-1,3-Glucan α-1,3-glucan having about 100% α-1,3 glycosidic linkages is described, for example, in U.S. Patent Application Publication No. 2014 / 0179913 (see, for example, Example 12 therein).

[0266] As another example, from an aqueous solution (0.5 L) containing Streptococcus salivarius gtfJ enzyme (100 units / L) described in U.S. Patent Application Publication No. 2013 / 0244288 (incorporated herein by reference), sucrose (100 g / L) obtained from OmniPur Sucrose (EM8550), potassium phosphate buffer (10 mM) obtained from Sigma Aldrich, and FermaSure® (100 ppm), an antibacterial agent obtained from DuPont with the pH adjusted to 5.5, a slurry of α-1,3-glucan was prepared. The resulting enzyme reaction was maintained at 20 - 25 °C for 24 hours. Since the α-1,3-glucan synthesized in the reaction is water-insoluble, a slurry was formed. Then, the α-1,3-glucan solid was collected using a Buchner funnel with a 325-mesh sieve attached to a 40-micrometer filter paper to form a wet cake containing about 60 - 80 wt% water.

[0267] Preparation of Representative α-1,6-Glucan with α-1,2 Branching Methods for preparing α-1,6-glucans containing various amounts of α-1,2 branching are disclosed in U.S. Patent 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 weights. A representative preparation procedure for α-1,2-branched α-1,6-glucan is provided below (containing 19% α-1,2-branching and 81% α-1,6 linkages). 1D 1The glycosidic bond distribution was quantified using H-NMR spectra. Additional samples of α-1,6-glucan with α-1,2-branches were prepared similarly. For example, one sample contained 32% α-1,2-branches and 68% α-1,6 linkages, and another sample contained 10% α-1,2-branches and 90% α-1,6 linkages.

[0268] Using a stepwise combination of glucosyltransferase (dextransucrase) GTF8117 and α-1,2-branching enzyme GTFJ18T1, soluble α-1,6-glucan with approximately 19% α-1,2-branches was prepared according to the following procedure. A reaction mixture (2 L) composed of sucrose (450 g / L), GTF8117 (9.4 U / mL), and 50 mM sodium acetate was adjusted to pH 5.5 and stirred at 47 °C. Aliquots (0.2 - 1 mL) were withdrawn at predetermined times and quenched by heating at 90 °C for 15 minutes. The obtained heat-treated aliquots were passed through a 0.45 μm filter. The flow-through fractions were analyzed by HPLC to determine the concentrations of sucrose, glucose, fructose, leucrose, oligosaccharides, and polysaccharides. After 23.5 hours, the reaction mixture was 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 monosaccharides / disaccharides, oligosaccharides, and polysaccharides. The major product was linear dextran with a DPw of 93.

[0269] The second reaction mixture was prepared by adding 238.2 g of sucrose and 210 mL of α-1,2 branching enzyme GTFJ18T1 (5.0 U / mL) to the remaining heat-treated reaction mixture obtained from the GTF8117 reaction described immediately above. The mixture was stirred at 30 °C with a volume of about 2.2 L. Aliquots (0.2 - 1 mL) were taken out at predetermined times and quenched by heating at 90 °C for 15 minutes. The resulting heat-treated aliquots were passed through a 0.45 μm filter. The filtrate fractions were analyzed by HPLC to determine the concentrations of sucrose, glucose, fructose, leucrose, oligosaccharides, and polysaccharides. After 95 hours, the reaction mixture was 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 filtrate was analyzed for soluble monosaccharides / disaccharides, oligosaccharides, and polysaccharides. The remaining heat-treated mixture was centrifuged using a 1 L centrifuge bottle. The supernatant was recovered and washed more than 200-fold using an ultrafiltration system containing a 1 kDa or 5 kDa MWCO cassette and deionized water. The washed oligosaccharide / polysaccharide product solution was dried. The dried sample was then 1 analyzed by 1H NMR spectroscopy to determine the anomeric linkages of the oligosaccharides and polysaccharides.

[0270] Example 1 Synthesis of Betaine Esters of Insoluble α-Glucans This example demonstrates the production of various forms of betaine α-1,3-glucan derivatives, which are soluble cationic glucan esters, using insoluble α-1,3-glucan.

[0271] Water-insoluble α-1,3-glucan (80 g [493.6 mmol]) (approx. 100% α-1,3 bonds) was suspended in 2.4 L of N,N-dimethylacetamide. Subsequently, the temperature of the preparation was raised to 120 °C and stirred at this temperature for 2 hours. After cooling to 80 °C, 144 g of LiCl was added to the preparation. After cooling the preparation to 70 °C, a clear solution was formed. Ground betaine hydrochloride (45.6 g [296.16 mmol], CAS registration number 590-46-5) (e.g., Sigma Aldrich, catalog number B3501) was added to the solution and then stirred at 70 °C for 10 minutes. Subsequently, 57.6 g (296.16 mmol) of tosyl chloride (dehydrating agent) was added to the solution and the preparation was reacted at 70 °C for 2 hours. A clear yellow solution was formed and then cooled to room temperature. The solid product was precipitated by adding 4 L of ethanol to one-third of the solution. This was done in each portion and then all the precipitated products were combined (similarly, the precipitated product could 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 liters of ethanol for each wash and then dried under vacuum at 40 °C.

[0272] α-1,3-glucan samples with different molecular weights (approx. 100% α-1,3 bonds, all water-insoluble) were reacted individually as described above, but different reagent amounts were used to produce betaine-modified α-1,3-glucan ester products with various molecular weights and degrees of substitution (DoS) levels. Table 1 shows various betaine α-1,3-glucan ester products (Samples A - F) that were successfully synthesized, and all of them readily dissolved in neutral water at room temperature.

[0273] [Table 1]

[0274] Example 2 Synthesis of betaine ester derivatives of soluble α-glucan This example demonstrates the production of various forms of betaine α-1,6-glucan derivatives, which are soluble cationic glucan esters, using soluble glucan α-1,2-branched α-1,6-glucan.

[0275] Various soluble α-1,2-branched α-1,6-glucans: 40 kDa α-1,6-glucan with 20% α-1,2-branching, 17 kDa α-1,6-glucan with 45% α-1,2-branching, and 300 kDa α-1,6-glucan with 45% α-1,2-branching were used for the esterification of betaine. In each of these α-glucans, the α-1,6-glucan backbone (from which the α-1,2-branches are present) has 100% α-1,6-glycosidic linkages, and the listed molecular weights are those of the α-1,6-glucan backbone. Each α-1,2-branch consisted of a single (pendent) glucose unit.

[0276] For the esterification of betaine, each of the above branched α-1,6-glucans (40 g) was individually dissolved in DMAc (200 mL) at high temperature (110 - 130 °C). Subsequently, betaine hydrochloride (40 g, CAS registration number 590-46-5) (e.g., Sigma Aldrich, catalog number B3501) and dicyandiamide (more than 20 g, dehydrating agent) were added to initiate the esterification. The uniformity of each reaction preparation was further adjusted by adding DI-water and / or CaCl2. Then, each reaction was heated under vacuum for less than 3 hours. Approximately 80 mL of the liquid was removed, and the crude product was precipitated in 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 named BC-2 (40 kDa α-1,6-glucan, 20% α-1,2-branching, DoS 0.02), BC-4 (40 kDa α-1,6-glucan, 20% α-1,2-branching, DoS 0.04), BC-10 (17 kDa α-1,6-glucan, 45% α-1,2-branching, DoS 0.04), and BC-11 (300 kDa α-1,6-glucan, 45% α-1,2-branching, DoS 0.04).

[0277] Example 3 Analysis of Betaine α-1,3-Glucan Ester Derivatives An aqueous solution of the betaine α-1,3-glucan ester product in Table 1 was prepared and analyzed for viscosity at room temperature (about 20 °C) using a Brookfield unit (spindle S03). High molecular weight glucan esters exhibit relatively high viscosity levels at relatively low concentrations (see Table 2, for example, product E), which is a desirable characteristic 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 with low molecular weights enable the production of high solids aqueous solutions (about 15 wt% or more) (see Table 2), which is a desirable characteristic in coating applications (e.g., paper coating), and higher solids minimize, for example, the required drying time and increase the overall process throughput.

[0278] [Table 2]

[0279] The effect of pH on the dissolution behavior of betaine-modified α-1,3-glucan in water was tested. A sample A (see Table 1) of a 20 wt% aqueous solution (about 1 mL) was added to 20 mL of water containing 4000, 400, 40, or 4 ppm of NaOH (the pH of the water was 13, 12, 11, or 10, respectively). At pH 13 and 12, the glucan ester came out of solution as a hard polymer that settled to the bottom (pH 13) or as a turbid solution (pH 12). At pH 11, more of the glucan ester remained in solution (some turbidity), but most, if not all, of the glucan ester remained in solution at pH 10. This dissolution behavior of the betaine-modified α-1,3-glucan ester was unexpected. Quaternary ammonium α-1,3-glucan ethers (e.g., hydroxypropyltrimethylammonium glucan ether) become more soluble at high pH, but the opposite was true for the betaine α-1,3-glucan ester. This behavior provides several advantages for using the betaine α-1,3-glucan ester in polymer processing. For example, the glucan ester can be extruded from water into fibers or films in a high pH bath. The ester chemical reaction can then be removed, if desired (chemically or enzymatically), to obtain a completely water-insoluble α-1,3-glucan product. Thus, the betaine-modified α-1,3-glucan ester makes it possible to maintain an aqueous processing environment and produce products containing non-derivatized α-1,3-glucan.

[0280] Biodegradability assay Biodegradability was determined according to the OECD 301B Ready Biodegradability CO2 Evolution Test Guideline (OECD, 1992. Organization for Economic Co-operation and Development, OECD 301 Ready Biodegradability. OECD Guidelines for the Testing of Chemicals, Section 3, incorporated herein by reference). In this assay, the test substance (betaine glucan ester) is the sole source of carbon and energy, and under aerobic conditions, microorganisms metabolize the test substance to produce CO2 or incorporate carbon into biomass. The amount of CO2 produced by the test substance (corrected for CO2 generated by the blank inoculum) is expressed as a percentage of the theoretical amount of CO2 (ThCO2) that could be produced if the organic carbon in the test substance were completely converted to CO2.

[0281] The biodegradation test of the betaine α-1,3-glucan ester derivative was carried out according to the OECD 301B test (described above). Samples of the glucan ester with the highest betaine group DoS (Sample F, Table 1) were analyzed for biodegradation over 28 days, and the results are shown in Figure 1 and Table 3.

[0282] [Table 3]

[0283] Sample F showed significant biodegradability within 28 days from the start of the test (Figure 1, Table 3). This result is surprisingly high in terms of biodegradability for the DoS (0.88) of sample F, and such DoS levels with different linkage / derivatization types (e.g., ether-linked carboxymethyl group or ether-linked hydroxypropyltrimethylammonium group) would typically greatly inhibit biodegradability. The improved biodegradability characteristics of the betaine α-1,3-glucan ester derivatives herein highly enable their use in applications where polymer bioaccumulation is not desired (e.g., the aquatic environment).

[0284] Example 4 Use of Betaine-Modified Glucan Esters in Beauty Care - Hair Styling Applications In this example, betaine α-1,3-glucan ester and betaine α-1,2-branched α-1,6-glucan ester were tested for characteristics related to hair styling applications. These different cationic glucan esters listed in Table 4 were tested for these applications along with a negative control (without using a glucan derivative) and a positive control (cationic glucan ether).

[0285] [Table 4]

[0286] Each test sample was completely dissolved in a 1 wt% ethanol / water (1:1) mixture. Subsequently, the turbidity of the solution was measured in nephelometric turbidity units (NTU) using a calibrated nephelometer (HACH 2100AN nephelometer). The solution was then poured into Petri dishes and evaporated overnight at room temperature. The quality of each resulting film was examined. For some of the tested betaine-modified glucan ester samples, good solubility and high-quality film formation were observed by low solution turbidity and the ability to form clear films, respectively (see Table 4). These characteristics are thought to provide useful materials for hair styling products that can enable clear and transparent coatings on hair to provide hair styling retention while avoiding an unclean appearance, for example.

[0287] In the curl retention test, approximately 1 gram of each solution (Table 4) was applied to a hair bundle (8-inch RINBOOOL hair sample). The resulting hair bundles were dried overnight at room temperature, and half of the hair bundles were curled and returned at an angle >90 degrees. Each hair bundle was then suspended in an oven at 45 °C and heated for 3 hours. Next, the height of the curled half of each hair bundle was measured and compared to the height of the hair bundle that existed before suspension (Table 4). In the control experiment, the height of the curled half of the hair bundle changed by 6.5 cm. However, for some of the hair bundles treated with the betaine-modified glucan ester sample, the height of the curled half of the hair bundle did not change or changed very little (see Table 4), indicating significant hair styling retention.

[0288] Example 5 Use of Betaine-Modified Glucan Ester in Coating In this example, paper was coated using betaine α-1,3-glucan ester. This coating provided an oil / grease barrier to the paper.

[0289] The betaine α-1,3-glucan ester (Sample A, Table 1) was applied to a paper substrate as a solution prepared by dissolving 10 wt% or 20 wt% of betaine α-1,3-glucan powder in distilled water. For example, to prepare 50 grams of a 10 wt% preparation, 5 grams of betaine glucan powder was dissolved in 45 grams of water. Each preparation was stirred at room temperature using a magnetic stir bar until all the powder was dissolved. Alternatively, a laboratory blender can be used if necessary. The viscosity of each solution increased as the betaine glucan dissolved in water.

[0290] Once the betaine α-1,3-glucan powder was completely dissolved, the resulting solution was applied to a foldable box-shaped paper substrate (METSABOARD CLASSIC FBB, basis weight 235 gsm, thickness 0.425 mm) using an automatic rod coater equipped with a heating module (MODEL PROCEQ ZAA 2600.A, Zehntner Testing Instruments). Different rods (Zehntner) were used to provide the desired coating thickness and basis weight to the paper substrate: rod #3 (reference ACC378.006, wet thickness 6.9 μm) and rod #14 (reference ACC378.032, wet thickness 32.0 μm). The coating speed was set at 20 mm / min and the coating was applied at room temperature. The coated paper was dried overnight under ambient conditions. It is also possible to shorten the drying time, and the drying can optionally be carried out, for example, in an oven at 60 °C for 10 minutes. In one test, this procedure was applied to the pre-treated side of the cardboard (pre-treatment by the manufacturer for printing), and in another double test, this procedure was applied to the back side (non-printing side) of a separate piece of cardboard.

[0291] The oil barrier performance of each betaine α-1,3-glucan-coated paper substrate was 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. Compared to the negative control standard (paper without coating), papers coated with betaine α-1,3-glucan ester using either a 10 wt% or 20 wt% solution showed a significant oil barrier function (Table 5).

[0292]

Table 5

[0293] Example 6 Two-step process for the synthesis of amphiphilic glucan ester derivatives containing cationic and hydrophobic substituents This example demonstrates a two-step process using a water-soluble glucan, α-1,2-branched α-1,6-glucan, to produce a multifunctional amphiphilic α-glucan ester derivative. In particular, α-glucan derivatives substituted with betaine, benzoyl, lauroyl, and acetyl groups were produced.

[0294] Step - 1: Synthesis of a hydrophobic glucan ester derivative containing benzoyl and lauroyl substituents: Glucan powder (40 kDa α-1,6-glucan with 20% α-1,2-branching, 30 g) was dissolved in DMAc (150 mL) at 90 °C. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove approximately 60 mL of liquid. Then, benzoyl chloride (17 g) and lauroyl chloride (8 g) were added, and 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.

[0295] Step - 2. Synthesis of an amphiphilic glucan ester derivative containing betaine, benzoyl, and lauroyl substituents: The hydrophobic α-glucan ester product (20 g) prepared in the above step - 1 was dissolved in DMAc (100 mL) at a high temperature (110 °C). Subsequently, betaine hydrochloride (20 g, CAS registration number 590 - 46 - 5) (for example, Sigma Aldrich catalog number B3501), dicyandiamide (20 g), and water (3 mL) were added. This reaction preparation was distilled at 130 °C for 1 hour under vacuum to remove 40 mL of liquid. Subsequently, the reaction product was cooled to room temperature, and then the crude product was first precipitated in acetonitrile and then dissolved in water. Subsequently, the obtained aqueous solution was subjected to ultrafiltration (MWCO 5 kDa) and then freeze-dried to obtain 5.6 grams of the product, benzoyl lauroyl betaine α-1,2-branched α-1,6-glucan ester. In particular, the product 1 By 1H-NMR analysis, for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from the DMAc solvent), the DoS values of the acyl groups were determined to be 0.07, 0.52, 0.23, and 0.13, respectively.

[0296] Example 7 Two-step process for the synthesis of amphiphilic glucan ester derivatives containing betaine and hydrophobic substituents Step - 1: Synthesis of a hydrophobic glucan ester derivative containing benzoyl substituents and acetyl substituents: Glucan powder (40 kDa α-1,6-glucan having 20% α-1,2 branching, 200 g) was dissolved in DMAc (1000 mL) at 88 °C. This reaction preparation was distilled at 100 °C for 1 hour under vacuum to remove 300 mL of liquid. Subsequently, benzoyl chloride (110 g) was added, and then the reaction preparation was stirred at 88 °C for 2 hours. The obtained product, benzoyl α-1,2-branched α-1,6-glucan ester, was precipitated and purified using isopropanol and obtained in quantitative yield. In particular, the product 1 By 1H-NMR analysis, for benzoyl and acetyl (acetyl derived from the DMAc solvent), it was determined to have acyl group DoS values of 0.36 and 0.14, respectively.

[0297] Project - 2. Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine, Benzoyl, and Acetyl Substituents: The hydrophobic α - glucan ester product (10 g) prepared in the above Project - 1 was dissolved in DMAc (300 mL) at a high temperature (90 °C). Next, betaine hydrochloride (6 g) was added. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 30 mL of liquid. Then, tosyl chloride (12 g) was added. This final reaction preparation was heated at 75 °C for 1 hour and then cooled to room temperature. Subsequently, the desired product was precipitated in isopropanol and washed three times with isopropanol, and benzoylacetylbetaine α - 1,2 - branched α - 1,6 - glucan ester was obtained. In particular, the product 1 was determined by 1H - NMR analysis to have acyl group DoS values of 0.27, 0.34, and 0.14 for betaine, benzoyl, and acetyl (acetyl derived from the DMAc solvent), respectively. The molecular weight of this final product was determined to be 10.5 kDa by SEC.

[0298] Example 8 Two - step Process for the Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine, Benzoyl, Lauroyl, and Acetyl Substituents Project - 1. Synthesis of Hydrophobic Glucan Ester Derivatives Containing Benzoyl, Lauroyl, and Acetyl Substituents: Glucan powder (40 kDa α - 1,6 - glucan with 20% α - 1,2 branching, 120 g) was swollen in DMAc (550 mL) at 90 °C for 1 hour. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 185 mL of liquid. Then, benzoyl chloride (74 g) and lauroyl chloride (30 g) were added, and then the reaction preparation was stirred at 90 °C for 1 hour and 45 minutes. The resulting product, benzoyllauroylacetyl α - 1,2 - branched α - 1,6 - glucan ester, was precipitated and purified using isopropanol and obtained in quantitative yield. In particular, the product 1 was determined by 1H - NMR analysis to have DoS values of the acyl groups of 0.64, 0.12, and 0.08 for benzoyl, lauroyl, and acetyl (acetyl derived from the DMAc solvent), respectively.

[0299] Engineering - 2. Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine, Benzoyl, Lauroyl, and Acetyl Substituents: The hydrophobic α - glucan ester product (10 g) prepared in the above Engineering - 1 was dissolved in DMAc (300 mL) at a high temperature (90 °C). Next, betaine hydrochloride (6 g) was added. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 30 mL of liquid. Then, tosyl chloride (12 g) was added. This final reaction preparation was heated at 75 °C for 1 hour and then cooled to room temperature. Subsequently, the desired product was precipitated in isopropanol and washed three times to obtain benzoyllauroylacetylbetaine α - 1,2 - branched α - 1,6 - glucan ester in a quantitative yield. In particular, the product was 1 Determined by 1H - NMR analysis to have acyl group DoS values of 0.13, 0.34, 0.03, and 0.01 for betaine, benzoyl, lauroyl, and acetyl (acetyl from the DMAc solvent), respectively. The molecular weight of this final product was determined to be 11.4 kDa by SEC.

[0300] Example 9 Two - step Process for the Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine, Benzoyl, Lauroyl, and Acetyl Substituents Engineering - 1. Synthesis of Hydrophobic Glucan Ester Derivatives Containing Benzoyl, Lauroyl, and Acetyl Substituents: Glucan powder (40 kDa α - 1,6 - glucan having 20% α - 1,2 - branching, 120 g) was swollen in DMAc (560 mL) at 90 °C for 1 hour. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 240 mL of liquid. Then, benzoyl chloride (74 g) and lauroyl chloride (30 g) were added, and then the reaction preparation was stirred at 90 °C for 1.5 hours. The resulting product, benzoyllauroylacetyl α - 1,2 - branched α - 1,6 - glucan ester, was precipitated and purified using isopropanol and obtained in a quantitative yield. In particular, the product was 1By H-NMR analysis, for benzoyl, lauroyl and acetyl (acetyl derived from DMAc solvent), the DoS values of the acyl groups were determined to be 0.57, 0.04 and 0.10, respectively.

[0301] Step - 2. Synthesis of amphiphilic glucan ester derivatives containing betaine, benzoyl, lauroyl and acetyl substituents: The hydrophobic α - glucan ester product (10 g) prepared in the above Step - 1 was dissolved in DMAc (300 mL) at a high temperature (90 °C). Then, CaCl2·2H2O (12 g) was added. Next, betaine hydrochloride (6 g) was added. This reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 30 mL of the liquid. Then, tosyl chloride (12 g) was added. This final reaction preparation was heated at 75 °C for 1 hour and then cooled to room temperature. Thereafter, the desired product was precipitated in isopropanol and washed three times to obtain benzoyllauroylacetylbetaine α - 1,2 - branched α - 1,6 - glucan ester in quantitative yield. In particular, the product 1 By H-NMR analysis, for betaine, benzoyl, lauroyl and acetyl (acetyl derived from DMAc solvent), it was determined to have DoS values of acyl groups of 0.28, 0.39, 0.02 and 0.12, respectively. The molecular weight of this final product was determined to be 8.1 kDa by SEC.

[0302] Example 10 One - pot synthesis of amphiphilic glucan ester derivatives containing cationic and hydrophobic substituents This example demonstrates a one - pot (single - step) process using a water - soluble glucan, α - 1,2 - branched α - 1,6 - glucan, to produce a multifunctional amphiphilic α - glucan ester derivative. In particular, an α - glucan derivative substituted with betaine, benzoyl, lauroyl and acetyl groups was produced.

[0303] Glucan powder (40 kDa α-1,6-glucan with 20% α-1,2 branching, 40 g) was dissolved in DMAc (200 mL) at a high temperature (90 °C). Then, CaCl2·2H2O (12 g) was added. Next, betaine hydrochloride (40 g) and tosyl chloride (25 g) were added. This reaction preparation was distilled at 100 °C for 1 hour under vacuum to remove 60 mL of liquid. Then, benzoyl chloride (15 g) and lauroyl chloride (10 g) were added to the reaction. This final reaction preparation was heated for one hour, then cooled to room temperature, and then approximately 200 mL of ethanol was added. The soluble portion of the preparation was diluted with water, purified by ultrafiltration (MWCO 5 kDa), and then lyophilized to obtain 10.8 g of the product, benzoyl lauroyl betaine α-1,2 branched α-1,6-glucan ester. In particular, the product 1 was determined by 1H-NMR analysis to have DOS values of the acyl groups of 0.07, 0.27, 0.16, and 0.08 for betaine, benzoyl, lauroyl, and acetyl (acetyl derived from the DMAc solvent), respectively.

[0304] Example 11 One-Pot Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine and Hydrophobic Substituents This example demonstrates a one-pot (single-step) process using a water-soluble glucan, α-1,2 branched α-1,6-glucan, to produce a multifunctional amphiphilic α-glucan ester derivative. In particular, an α-glucan derivative substituted with betaine, benzoyl, lauroyl, and acetyl groups was produced.

[0305] Glucan powder (40 kDa α-1,6-glucan with 20% α-1,2 branching, 20 g, pre-dried overnight at 45 °C) was swollen in DMAc (350 mL) at high temperature (90 °C) for 1 hour. After this step, betaine hydrochloride (6 g) was added. The reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove 30 mL of liquid. Then, benzoyl chloride (7 g) and lauroyl chloride (5 g) were added. The resulting reaction preparation was heated for 1 hour. Then, tosyl chloride (25 g) was added. The reaction preparation was stirred at 75 °C for an additional 1 hour and then cooled to room temperature. Isopropanol was added to precipitate the crude product. The solid product was washed several more 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, the product 1 By 1H-NMR analysis, for betaine, benzoyl, lauroyl, and acetyl (acetyl from the DMAc solvent), the DoS values of the acyl groups were determined to be 0.15, 0.05, 0.01, and 0.07, respectively. The molecular weight of this final product was determined to be 53.9 kDa by SEC.

[0306] Example 12 One-Pot Synthesis of Amphiphilic Glucan Ester Derivatives Containing Betaine, Benzoyl, Lauroyl, and Acetyl Substituents This example demonstrates a one-pot (single-step) process using a water-soluble glucan, α-1,2 branched α-1,6-glucan, to produce a multifunctional amphiphilic α-glucan ester derivative. In particular, an α-glucan derivative substituted with betaine, benzoyl, lauroyl, and acetyl groups was produced.

[0307] Glucan powder (40 kDa α-1,6-glucan with 20% α-1,2 branching, 20 g, pre-dried overnight at 45 °C) was swollen in DMAc (350 mL) at high temperature (90 °C) for 1 hour. After this step, betaine hydrochloride (6 g) was added. The reaction preparation was distilled under vacuum at 100 °C for 1 hour to remove about 30 mL of liquid. Then, benzoyl chloride (10 g) and lauroyl chloride (6.5 g) were added. The resulting reaction preparation was heated for 1 hour. Then, tosyl chloride (12 g) was added. The reaction preparation was stirred at 75 °C for an additional 1 hour and then cooled to room temperature. Isopropanol was added to precipitate the crude product. The solid product was washed several more 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, the product is 1 By 1H-NMR analysis, for betaine, benzoyl, lauroyl, and acetyl (acetyl from the DMAc solvent), the degree of substitution (DoS) values of the acyl groups were determined to be 0.20, 0.09, 0.22, and 0.19, respectively. The molecular weight of this final product was determined to be 10.4 kDa by SEC.

[0308] Example 13 Use of Amphiphilic Ester Derivatives in Beauty Care - Hair Styling Applications In this example, amphiphilic α-1,2 branched α-1,6-glucan esters were tested for characteristics related to hair styling applications. In particular, two different amphiphilic glucan esters produced above in Examples 6 and 10 (both being benzoyl lauroyl betaine α-1,2 branched α-1,6-glucan) were tested for these applications along with a negative control (no glucan derivative used).

[0309] Each glucan ester test sample was completely dissolved in a 4 wt% ethanol / water (3:1) mixture. Then, the turbidity of the solution was measured in nephelometric turbidity units (NTU) using a calibrated nephelometer (HACH 2100AN nephelometer). The turbidity measurements for each sample are listed in Table 6.

[0310] In the curl retention test, approximately 0.5 grams of each solution was applied to a hair bundle (8-inch RINBOOOL hair sample). The resulting hair bundle was dried overnight at room temperature, and half of the hair bundle was curled and returned at an angle of >90 degrees. Subsequently, the height of the curled half of each hair bundle was measured and compared with the height of the hair bundle that existed before drying. In the control experiment, the height of the curled half of the hair bundle changed by 6.0 cm. As a comparison, in the hair bundles treated with either of the amphiphilic glucan ester derivatives produced in Example 6 (Process 2 product) or 10 (one-pot product), the change in the height of the curled half of each hair bundle was much smaller (Table 6), thereby indicating a significant hair styling retention rate.

[0311]

Table 6

Claims

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

2. The composition according to claim 1, wherein the glucan is an 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 α - glucan are α - 1,6 bonds, and optionally, the α - glucan contains at least 1% of α - 1,2 and / or α - 1,3 branches.

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

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

5.

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

5.

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

5.

9. The cationic organic group has the structure: 【Chemical 1】 and includes, R １ , R ２ and R ３ each is, independently, a group containing at least one carbon atom The composition according to claim 1.

10. The cationic organic group has the structure: 【Chemical Formula 2】 and includes, R １ , R ２ and R ３ each is, independently, a group containing at least 1 carbon atom The composition according to claim 9.

11. The hydrophobic organic group is C ２ -C ２６ The composition according to claim 1, which contains an acyl group.

12. The composition according to claim 1, wherein the hydrophobic organic group includes an aryl group.

13. The composition according to claim 1, wherein the ester derivative of the glucan has a biodegradability of at least 10% as determined by the carbon dioxide evolution test method after 15 days.

14. The composition according to claim 1, wherein the composition is an aqueous composition.

15. The composition according to claim 1, which is a household care product, a personal care product, an industrial product, an ingestible product or a pharmaceutical.

16. The composition according to 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 esterifying agents, wherein at least one of the esterifying agents contains a cationic organic group, At least one of the esterifying agents includes a hydrophobic organic group, 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, the ester derivative of the glucan has a degree of substitution (DoS) of up to about 3.0 with the cationic organic group and the hydrophobic organic group, a process, (b) Optionally, a step of isolating the ester derivative of the glucan produced in step (a); A method for producing an ester derivative of glucan, comprising:

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

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