Compositions with improved solubilizing agents

Abstract

Solubilizing agents formed from a polyol ester of fatty acid (PEFA) compound or derivative are disclosed. The solubilizing agents exhibit improved effectiveness at lower concentration levels than conventional solubilizing agents having similar HLB value. Methods of making and using the solubilizing agents are further disclosed.

Description

COMPOSITIONS WITH IMPROVED SOLUBILIZING AGENTSCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] The present application claims the priority benefit of U.S. Provisional Patent App. Serial No. 63 / 614,366, filed December 22, 2023, which is hereby incorporated herein by reference in its entirety.TECHNICAL FIELD

[0002] The present disclosure relates generally to compositions with improved solubilizing agents formed from polyol esters of fatty acids (PEFAs) compounds and derivatives thereof.BACKGROUND

[0003] Numerous applications, including personal care products, home care products, industrial products, food and beverage, and agricultural products require the formation of compositions including, or interacting with, insoluble or weakly soluble components. Solubilizers enable such compositions to be formed by enhancing the miscibility of the insoluble or weakly soluble components and further increase the stability of such compositions by reducing, or preventing, phase separation of the insoluble or weakly soluble components. While known solubilizers are generally effective, there is a need for improved solubilizer agents that can exhibit additional benefits that are not achievable with known solubilizer agents.SUMMARY

[0004] According to one embodiment, a composition includes a solute, a solvent and a solubilizing agent comprising a polyol ester of fatty acids (“PEFA”) compound having a hydrophilic-lipophilic balance (“HLB”) value of about 10 or greater.

[0005] A method of forming a sulfated polyol ester fatty acid compound comprising the steps of providing a polyol ester of fatty acid compounds (“PEFA compound”) and sulfating the PEFA compound.DETAILED DESCRIPTION

[0006] The details of various embodiments of the disclosure are set forth in the description below. Other features, objects, and advantages of the disclosure will be apparent from the description and from the claims.Definitions

[0007] As used herein, weight percent (wt%), percent by weight, % by weight, and the like are synonyms that refer to the concentration of a substance as the weight of that substance divided by the weight of the composition and multiplied by 100.

[0008] As used herein, the term “3-hydroxy fatty acid” or “3-hydroxy fatty acyl moiety” refers to a fatty acid wherein the third carbon from the acid end of the compound is hydroxylated.

[0009] As used herein, the term “about,” preceding a figure encompasses plus or minus 10%, or less, of the value of said figure. It is to be understood that the value to which the term “about” refers is itself also specifically, and preferably, disclosed.

[0010] As used herein, the term “alkyl” refers to a straight or branched alkyl group. Exemplary alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.

[0011] As used herein, the term “halogen” means F, Cl, Br, or I.

[0012] As used herein, the term “hydrophilic-lipophilic balance” or “HLB” refers to the degree of hydrophilicity and lipophilicity of a surfactant. High HLB surfactants are hydrophilic and have an HLB value of about 10 or greater.

[0013] As used herein, a polyol lipid means a compound wherein a polyol moiety is covalently attached to a fatty acid.

[0014] As used herein, the term “salt or acid thereof’ refers to any salts or acids of PEFA compounds. Exemplary salts and acids of PEFA compounds are suitable for use in contact with the tissues of humans and lower animals without undue toxicity, irritation, allergic response and the like, and are commensurate with a reasonable benefit / risk ratio. Salts can include pharmaceutically or biologically acceptable salts. Likewise, acids can include pharmaceutically or biologically acceptable acids. Pharmaceutically or biologically acceptable salts and acids are wellknown in the art. For example, S. M. Berge et al., describe pharmaceutically or biologically acceptable salts in detail in J. Pharmaceutical Sciences, 1977, 66, 1-19, incorporated herein by reference. Pharmaceutically or biologically acceptable salts of the compounds of this disclosure can include those derived from suitable inorganic and organic acids and bases, while pharmaceutically or biologically acceptable acids of the compounds of this disclosure can include suitable inorganic and organic acids. Examples of pharmaceutically or biologically acceptable inorganic acids can include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, and perchloric acid or with organic acids such as acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid, propionic acid or malonic acid or by using other methods used in the art such as ion exchange. Examples of pharmaceutically or biologically acceptable acid addition salts are salts of an amino group formed with such examples of inorganic acids. Another example of a pharmaceutically or biologically acceptable acid is a carboxylic acid, where the carboxylated version of the PEFA compound includes a carboxyl group. Other pharmaceutically or biologically acceptable salts include adipate, alginate, ascorbate, aspartate, benzenesulfonate, benzoate, bisulfate, borate, butyrate, camphorate, camphor sulfonate, citrate, cyclopentanepropionate, digluconate, dodecyl sulfate, ethanesulfonate, formate, fumarate, glucoheptonate, glycerophosphate, gluconate, hemi sulfate, heptanoate, hexanoate, hydroiodide, 2- hydroxy-ethanesulfonate, lactobionate, lactate, laurate, lauryl sulfate, malate, maleate, malonate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, oleate, oxalate, palmitate, pamoate, pectinate, persulfate, 3-phenylpropionate, phosphate, pivalate, propionate, stearate, succinate, sulfate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate salts, and the like.

[0015] As used herein, the term “solubilizer” or “solubilizing agent” refers to compounds that render insoluble or weakly soluble components soluble or improve their respective solubility; and further increase phase stability and reduce phase separation. Insoluble and weakly soluble components refer to solids or liquids which are not miscible into the compositions described herein.

[0016] As used herein, the term “sugar alcohol” refers to carbohydrate compounds containing one hydroxyl group (-OH) attached to each carbon atom. Exemplary sugar alcohols include Erythritol (4-carbon), threitol (4-carbon), arabitol (5-carbon), Xylitol (5-carbon), ribitol (5-carbon), mannitol (6-carbon), sorbitol (6-carbon), galactitol (6-carbon), and fucitol (6-carbon).

[0017] Salts derived from appropriate bases include alkali metal, alkaline earth metal, ammonium and N(Cl-4alkyl)4 salts. Representative alkali or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium, and the like. Further pharmaceutically or biologically acceptable salts include, when appropriate, ammonium, quaternary ammonium, and amine cations formed using counterions such as halide, hydroxide, carboxylate, sulfate, phosphate, nitrate, lower alkyl sulfonate and aryl sulfonate.

[0018] The present disclosure includes both the (R) and (S) configuration at each stereo center, even in cases where drawn as defined or drawn undefined. Additionally, the present disclosure includes racemic compositions of compounds disclosed herein. The present disclosure includes scalemic compositions of compounds disclosed herein. The present disclosure includes enantioenriched compositions of compounds disclosed herein.

[0019] As will be described herein, advantageous solubilizing agents are disclosed. Generally, the solubilizing agents can be polyol esters of fatty acids (PEFAs). The solubilizing agents described herein can exhibit a high effective HLB value and can be more effective at solubilizing weakly soluble components than known solubilizing agents having comparable HLB values. In certain embodiments, the solubilizing agents described herein can be included in lower loading levels than comparable solubilizing agents of similar HLB value while achieving similar or better performance. The solubilizing agents can be free of 1,4-dixoane.

[0020] Polyol lipids can be isolated and / or purified from a yeast culture according to methods known in the art. Since the polyol lipids are extracellularly secreted from yeast cells, the one or more polyol lipids can be isolated and / or purified from the yeast cell culture without cell lysis or extraction requiring an organic solvent.

[0021] PEFAs are amphiphilic molecules comprising a sugar alcohol, e.g., a D-mannitol and / or a D-arabitol, esterified to the carboxyl end of a 3-hydroxy fatty acyl moiety, which may or may not be acetylated. The non-esterified hydroxy groups of the sugar alcohol may or may not be acetylated as well. In some embodiments, the one or more polyol lipids produced are a mixture of similar compounds containing (R)-3 -hydroxy fatty acyl moi eties with varying chain lengths, in the range of about 8 to 24 carbons, preferably in the range between 12 to 20 carbons. In some embodiments, the (R)-3 -hydroxy fatty acyl moieties can present varying degrees of unsaturation in the range ofabout 0 to 6, e.g., in the range between 2 to 5. In some embodiments, the non-esterified hydroxy groups of the sugar alcohol can be esterified to acetyl groups. In some embodiments the sugar alcohol can be fully acetylated. In some embodiments, the sugar alcohol can be non-acetylated. In some embodiments, acetylations can range between these two states.

[0022] In some embodiments, a polyol lipid disclosed herein is an acetylated Cl 2: 0-3 -hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 2 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol with 2 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated Cl 6:0-3-hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated Cl 6:0-3 -hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated Cl 6:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 2 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated Cl 6:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, the polyol lipid is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 2 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C16:0- 3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C18:0-3- hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C18:0-3- hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, a polyol lipiddisclosed herein is an acetylated Cl 8:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C18:0-3- hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C20: 0-3 -hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, a polyol lipid disclosed herein is an acetylated C20:0-3- hydroxy fatty acid esterified to D-mannitol with 4 acetylations.

[0023] Exemplary Compounds

[0024] In some embodiments, the solubilizing agents are PEFA compounds represented by the group consisting of:or salt or acid thereof.

[0025] In some embodiments, the solubilizing agents are PEFA compounds represented by Formula (I) or (II):(ii), or salt or acid thereof, whereinR1is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOra), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, - (O)NH2, -(O)(CjHkOm);R2is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, - (O)NH2, -(O)(CjHkOm);R3is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, - (O)NH2, -(O)(CjHkOm);R4is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, - (O)NH2, -(O)(CjHkOm);R5is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX,-(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(0)N02, - (O)NH2, -(O)(CjHkOm);Rais selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -NO2, -COOH, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, - (O)NH2, -(O)(CjHkOm); each Rxis independently C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; each Ryis independently -H, C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; n is 2-20; j is 2-12; k is 4-26; m is 1-16; and each p is independently selected from 1-10, wherein when n is 12 or 14 and R1is -OH or -(O)Ac, then Rais not -(O)Ac or -(O)Me; when n is 12 and Rais -OH, then R2is not -OH or; when n is 12 or 14, Rais -OH, R2is OH, R3is OH, and R4is OH, then R1is (O)RXor -(O) (C2H5O)PRy; when n is 12 or 14, R1is -(O)S(O2)OH, R2is -(O)S(O2)OH, R3is -(O)S(O2)OH, R4is - (O)S(O2)OH, and R5is -(O)S(O2)OH, then Rais -(O)C(O)RX, (O)RX, -(O)C(O)ORX, - (O)C(O)N(H)RX, -(O)(C2H5O)pRy, -(O)P(O)(OH)2, or -(O)S(O2)OH.

[0026] In some embodiments, the solubilizing agents are compounds of Formula (I) or (II), whereinR1is selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH;R2is selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O) (C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH;R3is selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH;R4is selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH;R5is selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH;Rais selected from the group consisting of -OH, -COOH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, - (O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, and -(O)S(O2)OH; each Rxis independently C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; each Ryis independently - H, C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; n is 2-11; and each p is independently selected from 1-10.

[0027] In some embodiments, the solubilizing agents are PEFA compounds represented by Formula (I-a) or (Il-a):(Il-a) or salt or acid thereof, wherein n is 6-12.R

[0028] In some embodiments, R1is selected from the group consisting of -H, -C(O)RX, -Rx, - C(O)ORy, -C(O)N(H)Ry, -(C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, - (O)S(O2)OH, -(O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, R1is selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy, -P(O)(OH)2, and -S(O2)OH. In some embodiments, R1is -H. In some embodiments, R1is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R1is -C(O)RX. In some embodiments, R1is -Ac. In some embodiments, R1is -Rx. In some embodiments, R1is -C(O)ORy. In some embodiments, R1is -C(O)N(H)Ry. In some embodiments, R1is -(C2H5O)PRy. In someembodiments, R1is -P(O)(OH)2. In some embodiments, R1is -S(O2)OH. In some embodiments, R1is -(CjHkOm).

[0029] In some R2is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, - C(O)N(H)Ry, -(C2H5O)PRy-P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(CjHkOm), -OH, -(O)C(O)RX, - (O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, - (O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, R2is selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy, -P(O)(OH)2, and -S(O2)OH. In some embodiments, R2is -H. In some embodiments, R2is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R2is -C(O)RX. In some embodiments, R2is -Ac. In some embodiments, R2is -Rx. In some embodiments, R2is -C(O)ORy. In some embodiments, R2is -C(O)N(H)Ry. In some embodiments, R2is -(C2H5O)pRy. In some embodiments, R2is -P(O)(OH)2. In some embodiments, R2is -S(O2)OH. In some embodiments, R2is -(CjHkOm).

[0030] In some embodiments, R3is selected from the group consisting of -H, -C(O)RX, -Rx, - C(O)ORy, -C(O)N(H)Ry, -(C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(CjHkOm), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, - (O)S(O2)OH, -(O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, R3is selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy, -P(O)(OH)2, and -S(O2)OH. In some embodiments, R3is -H. In some embodiments, R3is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R3is -C(O)RX. In some embodiments, R3is -Ac. In some embodiments, R3is -Rx. In some embodiments, R3is -C(O)ORy. In some embodiments, R3is -C(O)N(H)Ry. In some embodiments, R3is -(C2H5O)PRy. In some embodiments, R3is -P(O)(OH)2. In some embodiments, R3is -S(O2)OH. In some embodiments, R3is -(CjHkOm).R4

[0031] In some embodiments, R4is selected from the group consisting of -H, -C(O)RX, -Rx, - C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy, -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(CjHkOm), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, - (O)S(O2)OH, -(O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, R4is selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy-P(O)(OH)2, and -S(O2)OH. In some embodiments, R4is -H. In some embodiments, R4is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R4is -C(O)RX. In some embodiments, R4is -Ac. In some embodiments, R4is -Rx. In some embodiments, R4is -C(O)ORy. In some embodiments, R4is -C(O)N(H)Ry. In some embodiments, R4is -(C2H5O)PRy. In some embodiments, R4is -P(O)(OH)2. In some embodiments, R4is -S(O2)OH. In some embodiments, R4is -(CjHkOm).

[0032] In some embodiments, R3is selected from the group consisting of -H, -C(O)RX, -Rx, - C(O)ORy, -C(O)N(H)Ry, -(C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(CjHkOm), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, - (O)S(O2)OH, -(O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, R3is selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, -(C2H5O)pRy, -P(O)(OH)2, and -S(O2)OH. In some embodiments, R3is -H. In some embodiments, R3is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R5is -C(O)RX. In some embodiments, R5is -Ac. In some embodiments, R5is -Rx. In some embodiments, R5is -C(O)ORy. In some embodiments, R5is -C(O)N(H)Ry. In some embodiments, R5is -(C2H5O)pRy. In some embodiments, R5is -P(O)(OH)2. In some embodiments, R5is -S(O2)OH. In some embodiments, R5is -(CjHkOm).

[0033] In some embodiments, Rais selected from the group consisting of -H, -C(O)RX, -Rx, - C(O)ORy, -C(O)N(H)Ry, -(C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(CjHkOm), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, - (O)S(O2)OH, -(O)NO2, -(O)NH2, and -(O)(CjHkOm), where -(CjHkOm) can be in linear or cyclic form. In some embodiments, Rais selected from the group consisting of -C(O)RX, -Rx, -C(O)ORy,-C(O)N(H)Ry, -(C2HsO)pRy, -P(O)(OH)2, and -S(O2)OH. In some embodiments, Rais -H. In some embodiments, Rais -P(O)(OH)2, or -S(O2)OH. In some embodiments, Rais -C(O)RX. In some embodiments, Rais -Ac. In some embodiments, Rais -Rx. In some embodiments, Rais -C(O)ORy. In some embodiments, Rais -C(O)N(H)Ry. In some embodiments, Rais -(C2HsO)pRy. In some embodiments, Rais -P(O)(OH)2. In some embodiments, Rais -S(O2)OH. In some embodiments, Rais -(CjHkOm).

[0034] In some embodiments, each Rxis independently C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen. In some embodiments, Rxis methyl, wherein Rxis optionally substituted with 1-7 instances of halogen. In some embodiments, Rxis ethyl, wherein Rxis optionally substituted with 1-7 instances of halogen. In some embodiments, Rxis n-propyl, wherein Rxis optionally substituted with 1-7 instances of halogen. In some embodiments, Rxis i- propyl, wherein Rxis optionally substituted with 1-7 instances of halogen. In some embodiments, Rxis methyl. In some embodiments, Rxis ethyl. In some embodiments, Rxis n-propyl. In some embodiments, Rxis i -propyl.

[0035] In some embodiments, each Ryis independently -H or C1-C3alkyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis -H. In some embodiments, each Ryis independently C1-C3alkyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis methyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis ethyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis n-propyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis i-propyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis methyl. In some embodiments, Ryis ethyl. In some embodiments, Ryis n-propyl. In some embodiments, Ryis i- propyl.Preparation of Solubilizing Agents

[0036] Below are examples of specific embodiments described by the present disclosure. The examples are offered for illustrative purposes only and are not intended to limit the scope of the present invention in any way. The groups referenced in the examples below, e.g., OR1, OR2, etc., refer to the corresponding groups described herein, e.g., R1, R2, etc., and can be replaced with any of the groups provided in the respective corresponding group, i.e., without the “O.” Efforts have been made to ensure accuracy with respect to numbers used (e.g., amounts, temperatures, etc.), but some experimental error and deviation should, of course, be allowed for.

[0037] In some embodiments, the solubilizing agents described herein can be prepared as outlined in Scheme 1 or 2:Scheme 1wherein LG is a leaving group.Scheme 2wherein LG is a leaving group.

[0038] In some embodiments, the solubilizing agents described herein can be prepared as outlined in Scheme 3 or 4:Scheme 3Scheme 4

[0039] In some embodiments, the solubilizing agents described herein can be prepared as outlined in Scheme 5 or 6:Scheme 5

[0040] In certain embodiments, the solubilizing agents described herein can be formed by reacting the PEFA compounds with sulfamic acid to replace aliphatic alcohols as depicted in the below scheme:

[0041] In yet other certain embodiments, the solubilizing agents described herein can be formed by reaction of the PEFA compounds with chlorosulfonic acid. In this process, the alcohol containing PEFA compound is reacted with chlorosulfonic acid, or a slight excess thereof, mixed with an equimolar amount of acetic acid. This reaction is exothermic and the temperature is controlled with extensive cooling. The reaction is complete after a short time and the mixture is neutralized with solid sodium carbonate to give the product, sodium salt of the sulfate ester with sodium acetate as a byproduct. The reaction scheme is depicted below:

[0042] In certain embodiments, glycosylated PEFA compounds can be formed. In the depicted scheme, PEFA compounds are glycosylated with fully protecting sugar groups where the reactive hydroxyl (acetal hydroxyl) was derivatized with a tri chloromethyl imine group and the non- reactive hydroxyl groups were protected with benzyl groups (Bn). This synthetic step was successfully accomplished using Trimethyl silyl trifluoromethanesulfonate (TMSOTf), an organosilicon compound typically used to activate ketones and aldehydes in organic synthesis.

[0043] Chemical glycosylation involves the coupling of a glycosyl donor to a glycosyl acceptor forming a glycoside. If both the donor and acceptor are sugars, then the product is an oligosaccharide. The reaction requires activation with a suitable activating reagent, in this case the TMSOTf.

[0044] The benzyl groups were cleaved using hydrogenation conditions using ethyl acetate as the solvent.

[0045] Synthesis / isolation of starting materials for the solubilizing agents described herein can be found in WO2018148465 and WO2017184884, each of which are incorporated in their entirety.Properties and Applications

[0046] Solubilizing agents formed from the described PEFA compounds can exhibit beneficial properties compared to known solubilizing agents. For example, the solubilizing agents described herein can solubilize more effectively than known solubilizing agents having similar HLB values. Such beneficial properties enable the formation of improved compositions or products having smaller amounts of solubilizing agents, greater quantities of insoluble or weakly soluble components, and / or reduced manufacturing and processing costs.

[0047] As can be appreciated, the solubilizing agents described herein can also be biologically manufactured and can exhibit more favorable safety and environmental profiles than conventional solubilizing agents which are typically synthesized from petroleum feedstock and which frequently have residual 1,4-di oxane. Being a fermentation product, the solubilizing agents described herein are renewable, less environmentally damaging, biodegradable, and have low-toxicity facilitating their use in applications where harsher and less environmentally friendly solubilizing agents are less preferred. The solubilizing agents described herein can be entirely free of 1,4-dioxane. In an embodiment, the solubilizing agents after production through fermentation can be chemically modified further as described herein.

[0048] In certain embodiments, the solubilizing agents can be inert so as to not react with the other components of a product or system in which it is introduced. In certain embodiments, the solubilizing agents can react minimally with the components of a product or system in which it is introduced. In certain embodiments, the solubilizing agents are present in an end product of a processing procedure. In certain embodiments, the solubilizing agents are physiologically safe orhave a safety profile that is biologically acceptable. In some embodiments, the solubilizing agents are biodegradable and / or environmentally safe or environmentally acceptable.

[0049] The HLB value of the solubilizing agents described herein can be at least about 10. For example, the HLB value can be about 12 to about 15, about 15 to about 18, or even about 18 to about 20. As can be appreciated, the HLB value only indicates the capability of a solubilizing agent to solubilize a particular component but does not indicate the amount of the solubilizing agent necessary to achieve such solubilization. The solubilizing agents described herein have been found to be effective at solubilizing components at lower concentrations than known surfactants having similar HLB values.

[0050] Generally, the solubilizing agents described herein can be used in any application where conventional solubilizing agents are utilized including, without limitation, personal care products, home care products, cosmetics products, food products, industrial products, institutional products, coating products, construction materials, adhesives materials, oil well materials, lubricants, agricultural products, food and beverage products, coatings products, pigmented products, nutraceuticals products, pesticidal products, and textile processing products. As can be appreciated, the solubilizing agents described herein can solubilize components in a formulation (e.g., an oil phase in a metalworking fluid) or solubilize soils that a composition is applied to when used (e.g., a cleaning formulation).

[0051] For example, in certain embodiments, the solubilizing agents described herein can be useful for household, industrial, and institutional (“HI&I”) cleaning compositions wherein the solubilizing agents can be used to sanitize surfaces the cleaning compositions are applied to by removing various soils on the surface, such as dirt, oil, food, and biological contaminants. Specific examples of HI&I products include hard surface cleaners and disinfectants, soaps, detergents, dishwashing compositions, clothes washing compositions, vehicle cleaners, industrial plant cleaners, degreasers, appliance cleaners, and janitorial cleaners.

[0052] Other example compositions which can include the solubilizing agents described herein include personal care compositions such as soaps, lotions, shampoos, bodywashes, cleaning pads, sunscreens, toothpastes, hygiene products, and other beauty products. The solubilizing agents can also be used, without limitation, in metalworking fluids, oil lubricants, in textile printing, inks,biocides, agricultural products, food contact surface cleaners, food processing cleaners, essential oils, food and beverage, food processing equipment, and perfumes.

[0053] Generally, the solubilizing agents described herein can be applied in dry or wet forms at any suitable concentration. For example, the concentration of the solubilizing agents in a toothpaste can be as low as about 0.5% while the concentration in a concentrated dishwashing tablet can be greater than about 40%.

[0054] The solubilizing agents disclosed herein can generally be combined with any number of adjunct ingredients and can generally work in conjunction with various solvents, additives, stabilizing agents, emulsifiers, co-solubilizers, and the like commonly found in compositions.

[0055] In certain embodiments, the solubilizing agents can be used in aqueous compositions. However, or additionally, the solubilizing agents can be used with non-aqueous solvents including hydrocarbons (both aromatic and aliphatic), oxygenated solvents (alcohols, ketones, aldehydes, ethers, glycol ethers, esters, and glycol ether esters), polyalkylene oxide, capped polyalkylene oxide, and combinations thereof. Suitable polyalkylene oxides include polyethylene glycol, polypropylene glycol, polybutylene glycol, mixtures thereof, or the like. Suitable capped polyalkylene oxides include mono-alkyl and di-alkyl ethers of the respective polyalkylene oxides, such as mono- and di-methyl ethers of polyalkylene glycol, mono- and di-ethyl ethers of polyalkylene glycol, mono- and di -propyl ethers of polyalkylene glycol, mono- and di -butyl ethers of polyalkylene glycol, mixtures thereof, or the like. Suitable capped polyalkylene oxides include methyl polyethylene glycol (e.g., the monomethyl ether of polyethylene glycol), dimethyl polyethylene glycol (e.g., the dimethyl ether of polyethylene glycol), mixtures thereof, or the like.

[0056] In certain embodiments, a conventional solubilizer can be included with one or more of the solubilizing agents as described herein. Such suitable co-solubilizers include glycol ethers. Suitable glycol ethers include diethylene glycol n-butyl ether, diethylene glycol n-propyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol t-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol propyl ether, dipropylene glycol tert-butyl ether, ethylene glycol butyl ether, ethylene glycol propyl ether, ethylene glycol ethyl ether, ethylene glycol methyl ether, ethylene glycol methyl ether acetate, propylene glycol n-butyl ether, propylene glycol ethyl ether, propyleneglycol methyl ether, propylene glycol n-propyl ether, tripropylene glycol methyl ether and tripropylene glycol n-butyl ether, ethylene glycol phenyl ether (commercially available as DOW ANOL EPH™ from Dow Chemical Co.), propylene glycol phenyl ether (commercially available as DOW ANOL PPH™ from Dow Chemical Co.), and the like, or mixtures thereof. Additional suitable commercially available glycol ethers (all of which are available from Union Carbide Corp.) include Butoxyethyl PROPASOL™, Butyl CARBITOL™ acetate, Butyl CARBITOL™, Butyl CELLOSOLVE™ acetate, Butyl CELLOSOLVE™, Butyl DIPROPASOL™, Butyl PROPASOL™, CARBITOL™ PM-600, CARBITOL™ Low Gravity, CELLOSOLVE™ acetate, CELLOSOLVE™, Ester EEP™, FILMER IBT™, Hexyl CARBITOL™, Hexyl CELLOSOLVE™, Methyl CARBITOL™, Methyl CELLOSOLVE™ acetate, Methyl CELLOSOLVE™, Methyl DIPROPASOL™, Methyl PROPASOL™ acetate, Methyl PROPASOL™, Propyl CARBITOL™, Propyl CELLOSOLVE™, Propyl DIPROPASOL™ and Propyl PROPASOL™.

[0057] Suitable additives which can work with the solubilizing agents described herein can include ethylene oxide / propylene oxide block copolymers, butylene oxide / propylene oxide block copolymers, ethylene oxide / butylene oxide block copolymers, waxes, or silicone-based materials.

[0058] Suitable stabilizing agents and preservatives for compositions formed from the solubilizing agents described herein can include oleic acid, hexylene glycol, fatty alcohols, naphthalene sulfonates, butyl alcohol, and formaldehyde.

[0059] In certain embodiments, the solubilizing agents described herein can be used in combination with additional surfactants and emulsifiers. Generally, such additional surfactants and emulsifiers can be anionic, cationic, nonionic or amphoterics and combination thereof. Nonlimiting examples of anionic surfactants and emulsifiers include alkali metal, ammonium and amine soaps; the fatty acid part of such soaps contains preferably at least 16 carbon atoms. Other non-limiting examples of anionic surfactants and emulsifiers include alkali metal salts of alkylaryl sulfonic acids, sodium dialkyl sulfosuccinate, sulfated or sulfonated oils, e.g., sulfated castor oil; sulfonated tallow, and alkali salts of short chain petroleum sulfonic acids. Non-limiting examples of cationic surfactants or secondary emulsifiers include salts of long chain primary, secondary or tertiary amines, such as oleylamide acetate, cetylamine acetate, di-dodecylaminelactate, the acetate of aminoethyl -aminoethyl stearamide, dilauroyl tri ethylene tetramine diacetate, l-aminoethyl-2-heptadecenyl imidazoline acetate; and quaternary salts, such as cetylpyridinium bromide, hexadecyl ethyl morpholinium chloride, and diethyl di-dodecyl ammonium chloride. Non-limiting examples of nonionic surfactants or secondary emulsifiers include condensation products of higher fatty alcohols with ethylene oxide, such as the reaction product of oleyl alcohol with 10 ethylene oxide units; condensation products of alkylphenols with ethylene oxide, such as the reaction product of is octyl phenol with 12 ethylene oxide units; condensation products of higher fatty acid amides with 5, or more, ethylene oxide units; polyethylene glycol esters of long chain fatty acids, such as tetraethylene glycol monopalmitate, hexaethyleneglycol monolaurate, nonaethyleneglycol monostearate, nonaethyleneglycol dioleate, tridecaethyleneglycol monoarachidate, tricosaethyleneglycol monobehenate, tricosaethyleneglycol dibehenate, polyhydric alcohol partial higher fatty acid esters such as sorbitan tristearate, ethylene oxide condensation products of polyhydric alcohol partial higher fatty acid esters, and their inner anhydrides (mannitol-anhydride, called Mannitan, and sorbitol-anhydride, called Sorbitan), such as glycerol monopalmitate reacted with 10 molecules of ethylene oxide, pentaerythritol monooleate reacted with 12 molecules of ethylene oxide, sorbitan monostearate reacted with 10- 15 molecules of ethylene oxide, mannitan monopalmitate reacted with 10-15 molecules of ethylene oxide; long chain polyglycols in which one hydroxyl group is esterified with a higher fatty acid and other hydroxyl group is etherified with a low molecular alcohol, such as methoxypolyethylene glycol 550 monostearate (550 meaning the average molecular weight of the polyglycol ether). Non-limiting examples of amphoteric surfactants include alkybetaine, alkyldimethylamine N- oxide, alkylamidopropylamine N-oxide, alkylamidopropylbetaine, cocamidopropyl betaine, cocoamphoacetate and cocoamphodiacetate, phosphatidyl serine, phosphatidylethanolamine, phosphatidylcholine, sphingomyelins, lauryldimethylamine oxide, and myristamine oxide. In some embodiments, a combination of two or more of these surfactants may be used; e.g., a cationic may be blended with a nonionic or an anionic with a nonionic. In certain embodiments, the solubilizing agent can also, or alternatively, be blended with insoluble materials.

[0060] The solubilizing agents described herein can generally solubilize a variety of insoluble components including soils (e.g., dirt, oil, food, biological contaminants), oils, fats, and various non-polar solvents. For example, in various embodiments, the solubilizing agents can disperse petroleum oils, vegetable oils, essential oils, fats, emollients, dirt, and various organic solvents.

[0061] Exemplary formulations for various products are disclosed including a toothpaste, a liquid laundry detergent, a tub and tile cleaner, an industrial cleaner, a mouthwash, an agricultural adjuvant, and a food surface contact cleaner.

[0062] An exemplary toothpaste formulation that can be manufactured with a solubilizing agents described herein is depicted in Table 1.TABLE 1

[0063] The formulation of an exemplary liquid laundry composition is depicted in Table 2.TABLE 2

[0064] The formulation of an exemplary tub and tile cleaner is depicted in Table 3.TABLE 3

[0065] The formulation of an exemplary industrial cleaner and degreaser is depicted in Table 4.TABLE 4

[0066] The formulation of an exemplary non-alcoholic mouthwash is depicted in Table 5.TABLE 5

[0067] The formulation of an exemplary agricultural adjuvant useful to increase the effectiveness of herbicidal and pesticidal compositions is depicted in Table 6. The adjuvant is added at about 0.05% to 1% of the herbicidal or pesticidal composition.TABLE 6

[0068] The formulation of an exemplary food surface contact cleaner is depicted in Table 7.TABLE 7EXAMPLES

[0069] Below are examples of specific embodiments for carrying out the present disclosure. The examples are offered for illustrative purposes only and are not intended to limit the scope of thepresent disclosure in any way. Efforts have been made to ensure accuracy with respect to numbers used (e.g., amounts, temperatures, etc.), but some experimental error and deviation should, of course, be allowed for.Inventive Example 1

[0070] Inventive Example 1 is a sulfated PEFA derived from a glycolipid yeast fermentation product. Inventive Example 1 has a HLB value of about 10 to about 15, a Critical Micelle Concentration of 48.4 (mg / L); an average longitudinal contact angle on fabric ( 1 g / L) of 140°-130°, an interfacial tension (Ig / L) with dodecane of 4.5 and with olive oil of 6.9, a Surface Tension Value at the Critical Micelle Concentration of 40 (mN / M) using the Wilhelmy Plate method, and a dynamic surface tension (1 / gL) of 46 mN / m at 5 seconds. The sulfated PEFA of Inventive Example 1 is depicted in Formula (I). The associated cation can be sodium or ammonium.Formula (I).

[0071] Oil Solubility of Inventive Example 1

[0072] The oil solubility of Inventive Example 1 was compared against two comparative examples of high HLB solubilizers. Comparative Example 1 is BioSS® RL marketed by Advanced BioCatalytics as a replacement for sodium lauryl sulfate or sodium laureth sulfate. Comparative Example 1 is a rhamnolipid-type surfactant. Comparative Example 2 is Tween® 80 marketed by Sigma Aldrich. Comparative Example 2 is a polyethylene glycol sorbitan monooleate having an HLB value of about 15. To evaluate the oil solubility, a composition comprising 1%, by weight, of various oils including rosemary essential oil, red rose and grapefruit fragrance, garden freshfragrance, and bamboo mint fragrance, was solubilized into water with the example solubilizing agents. Additionally, the amount of solubilizing agent required to solubilize an emulsifier (RubgGL-EMl) was further evaluated. The amount of each solubilizing agent necessary to form a miscible composition, by weight percent, in water for each of these insoluble components is depicted in Table 8.TABLE 8

[0073] As depicted in Table 8, Inventive Example 1 requires a substantially smaller loading level in evaluated compositions than the loading levels of the solubilizers of Comparative Examples 1 and 2 to solubilize the essential oils and fragrances. Using relative scaling, between 1.7 and 6.7 times less of Inventive Example 1 is required than any of Comparative Examples 1 and 2.Food and Beverage Ingredient Solubility

[0074] The ability of Inventive Example 1 to solubilize various food ingredients was evaluated and compared to Comparative Example 2 and Comparative Example 3. Comparative Example 3 is PEG 40 hydrogenated castor oil having an HLB value of about 15. The evaluated food ingredients include lime oil, orange oil, and lemon oil. The amount of each solubilizing agent necessary to form a miscible composition, by weight percent, in water for 1% of each of the food ingredients is depicted in Table 9.TABLE 9

[0075] As depicted in Table 9, Inventive Example 1 requires a substantially smaller loading level in evaluated compositions than the loading levels of the solubilizers of Comparative Examples 2 and 3 to solubilize the flavor oils. Using relative scaling, between 1.3 and 1.6 times less of Inventive Example 1 is required than either of the comparative high HLB solubilizers.Non-Polar Oils

[0076] Non-polar oils are difficult to solubilize in water. The ability of Inventive Example 1 and Comparative Examples 2 and 3 to solubilize a silicone oil were evaluated by dissolving 1 part silicone oil to 99 parts solubilizer. These 1% silicone oil, 99% solubilizer solutions were then titrated with water until a miscible composition was formed. Many compositions could not be solubilized to form a miscible composition. The weight percentage of solubilizer required to solubilize a given amount of silicone oil are depicted in Table 10.TABLE 10

[0077] As depicted in Table 10, only Inventive Example 1 was able to solubilize more than 0.03% silicone oil with Comparative Examples 2 and 3 being capable of solubilizing silicone oil at lower loading levels and with higher weight percentages of solubilizer. It is expected that up to about 5% silicone oil can be solubilized either in water or other solvents in certain embodiments.Foam Volume

[0078] The amount of foam generated by solubilizing agents can be important for various applications. The amount of foam volume generated was experimentally evaluated in accordance with ASTM standard DI 173 for Inventive Example 1 and Comparative Examples 1, 2, and 4-54. Comparative Example 4 is sodium dodecyl sulfate (sodium lauryl sulfate) having a calculated HLB value of 20 and a higher empirically measured HLB value. Comparative Example 5 is a non-ionic alkyl polyglycoside surfactant. The foam volumes are depicted in Table 11.TABLE 1 1

[0079] As depicted in Table 11, Inventive Example 1 exhibited a foam volume comparable to known solubilizing agents making it suitable for inclusion in a large variety of applications. The solubilizing agents were all observed to have good stability.

[0080] Those skilled in the art will recognize or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments in accordance with the invention described herein. The scope of the present invention is not intended to be limited to the above description, but rather is as set forth in the appended claims.

[0081] In the claims, articles such as “a,” “an,” and “the” may mean one or more than one unless indicated to the contrary or otherwise evident from the context. Claims or descriptions that include “or” between one or more members of a group are considered satisfied if one, more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process unless indicated to the contrary or otherwise evident from the context. The invention includes embodiments in which exactly one member of the group is present in, employed in, or otherwise relevant to a given product or process. The invention includes embodiments in which more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process.

[0082] It is also noted that the term “comprising” is intended to be open and permits but does not require the inclusion of additional elements or steps. When the term “comprising” is used herein, the term “consisting of’ is thus also encompassed and disclosed.

[0083] Where ranges are given, endpoints are included. Furthermore, it is to be understood that unless otherwise indicated or otherwise evident from the context and understanding of one of ordinary skill in the art, values that are expressed as ranges can assume any specific value or subrange within the stated ranges in different embodiments of the invention, to the tenth of the unit of the lower limit of the range, unless the context clearly dictates otherwise.

[0084] All cited sources, for example, references, publications, databases, database entries, and art cited herein, are incorporated into this application by reference, even if not expressly stated in the citation. In case of conflicting statements of a cited source and the instant application, the statement in the instant application shall control.

[0085] Section and table headings are not intended to be limiting.

[0086] It is to be understood that the words which have been used are words of description rather than limitation, and that changes may be made within the purview of the appended claims without departing from the true scope and spirit of the invention in its broader embodiments.

[0087] While the present invention has been described at some length and with some particularity with respect to the several described embodiments, it is not intended that it should be limited to any such particulars or embodiments or any particular embodiment, but it is to be construed with references to the appended claims so as to provide the broadest possible interpretation of such claims in view of the prior art and, therefore, to effectively encompass the intended scope of the invention.

[0088] All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. In addition, section headings, the materials, methods, and examples are illustrative only and not intended to be limiting.

Claims

WHAT IS CLAIMED IS:

1. A composition comprising: a solute and a solvent; and a solubilizing agent comprising a derivatized polyol ester of fatty acids (“PEFA”) compound having a hydrophilic-lipophilic balance (“HLB”) value of about 10 or greater.

2. The composition of claim 1, wherein the PEFA compound is represented by Formula (I) or (II):(II), or salt or acid thereof, whereinR1is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R2is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R3is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R4is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);Rais selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm); each Rxis independently C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; each Ryis independently -H, or C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; n is 2-20; j is 2-12; k is 4-26; m is 1-16; and each p is independently selected from 1-10, wherein when n is 12 or 14 and R1is -OH or -(O)Ac, then Rais not -(O)Ac or -(O)Me; when n is 12 and Rais -OH, then R2is not -OH or ; when n is 12 or 14, Rais -OH, R2is OH, R3is OH, and R4is OH, then R1is (O)RXor (O)(C2H5O)PRy;when n is 12 or 14, R1is -(O)S(O2)OH, R2is -(O)S(O2)OH, R3is -(O)S(O2)OH, R4is - (O)S(O2)OH, and R5is -(O)S(O2)OH, then Rais -(O)C(O)RX, Rx, -(O)C(O)ORX, - (O)C(O)N(H)RX, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, or -(O)S(O2)OH.

3. The composition of claim 2, wherein:R1is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOra), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R2is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R3is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOra), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R4is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);R5is selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm), -OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm);Rais selected from the group consisting of -H, -C(O)RX, -Rx, -C(O)ORy, -C(O)N(H)Ry, - (C2H5O)PRy, -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(CjHkOm),-OH, - (O)C(O)RX, -(O)RX, -(O)C(O)ORy, -(O)C(O)N(H)Ry, -(O)(C2H5O)PRy, - (O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(CjHkOm); each Rxis independently C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;each Ryis independently -H, or C1-C3alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen; n is 4-12; j is 2-12; k is 4-26; m is 1-16; and each p is independently selected from 1-10.

4. The composition of any preceding claim wherein the derivatized PEFA compound is an anionic surfactant.

5. The composition of claim 4, wherein the derivatized PEFA compound is sulfated.

6. The composition of claim 5, wherein the derivatized PEFA compound is:

7. The composition of claim 5, wherein the derivatized PEFA compound is:

8. The composition of claim 5, wherein the derivatized PEFA compound is an ammonium salt.

9. The composition of claim 5, wherein the derivatized PEFA compound is a sodium salt.

10. The composition of any one of claims 1 to 3, wherein the derivatized PEFA compound is a non-ionic surfactant.

11. The composition of claim 10, wherein the derivatized PEFA compound is glycosylated.

12. The composition of claim 11, wherein one or more of R1, R2, R3, R4, R5, and Racomprise a derivatized sugar or derivatized sugar alcohol.

13. The composition of any claim 11, wherein one or more of R1, R2, R3, R4, R5, and Racomprise deprotonated forms of sugars and sugar alcohols including glucose, sucrose, fructose, galactose, erythritol (4-carbon), threitol (4-carbon), arabitol (5-carbon), Xylitol (5-carbon), ribitol (5-carbon), mannitol (6-carbon), sorbitol (6-carbon), galactitol (6-carbon), and fucitol (6-carbon).

14. The composition of claim 11, wherein the sugar moiety comprises D-mannitol or D- arabitol.

15. The composition of claim 11, wherein the derivatized PEFA compound is one or more of:

16. The composition of claim 11, wherein the derivatized PEFA compound is one or more of:

17. The composition of any preceding claim, wherein the derivatized PEFA compound is selected from one of pentitol polyol esters, hexitol polyol esters, or a combination thereof.

18. The composition of any preceding claim, wherein the derivatized PEFA compound is a biologically derived agent.

19. The composition of any preceding claim, wherein the derivatized PEFA compound comprises a sugar moiety and a fatty acid moiety.

20. The composition of any preceding claim, wherein the fatty acid moiety comprises a C12 to C20 fatty acid or C 12 to C20 fatty acyl.

21. The composition of any preceding claim further comprises one or more additional PEFA compounds or derivatized PEFA compounds.

22. The composition of claim 21, wherein at least one of the one or more additional PEFA compounds or derivatized PEFA compounds has an HLB of less than 10.

23. The composition of any preceding claim further comprises one or more additional surfactants.

24. The composition of any preceding claim exhibits a foam height of about 25 mL to about 35 mL when measured in accordance with ASTM DI 173.

25. The composition of any preceding claim exhibits a foam height of about 30 mL when measured in accordance with ASTM DI 173.

26. The composition of any preceding claim is a food product or beverage product.

27. The composition of any one of claims 1 to 25 is a personal care product.

28. The composition of any one of claims 1 to 25 is an industrial product.

29. The composition of any one of claims 1 to 25 is a household, industrial or institutional product.

30. The composition of any one of claims 1 to 25 is a textile printing product, a biocidal product, an agricultural product, a personal care product, a cosmetics product, a food and beverage product, a nutraceuticals product, a textiles product, an oil and gas product, a coating product, a pigmented product, a biocidal product, a metalworking fluid, a lubricant, a degreaser, an ink or toner product, or a coating product.

31. The composition of any preceding claim is an aqueous composition.

32. The composition of any preceding claim comprising: about 2% to about 6%, by weight, of the PEFA compound; and about 1%, by weight, of a solute.

33. The composition of any preceding claim, wherein the solute is an essential oil.

34. The composition of claim 33, wherein the essential oil comprises one or more of rosemary essential oil, red rose and grapefruit essential oil, garden fresh essential oil, and bamboo mint essential oil.

35. The composition of claim 33, wherein the solute is a vegetable oil.

36. The composition of claim 33, wherein the solute is a non-polar solvent.

37. The composition of claim 33, wherein the solute is a soil.

38. The composition of claim 33, wherein the solute is a flavor ingredient, a food ingredient, or a beverage ingredient.

39. The composition of claim 38, wherein the solute comprises one or more of peppermint oil, lemon oil, lime oil, or orange oil.

40. The composition of any of claims 1 to 31, wherein the solute comprises a polar or nonpolar oil.

41. The composition of claim 40, wherein the solute comprises a mineral oil.

42. The composition of claim 40, wherein the solute comprises a silicone oil, and wherein the silicone oil comprises about 5% or less of the composition.

43. The composition of claim 42, wherein the silicone oil comprises about 0.05% or less of the composition.

44. The composition of any one of claims 1 to 31 comprising about 1% of a solute and wherein the composition comprises less of the PEFA compound than comparable compositions formed with traditional solubilizing agents.

45. The composition of any one of claims 1 to 31 comprising about 1% or a solute and wherein the composition comprises less of the PEFA compound than a similar composition formed with glycolipid or ethoxylate surfactants.

46. The composition any one of claims 1 to 31, comprising: about 2% to about 6%, by weight, of the PEFA compound; and about 1%, by weight, of a polyol ester fatty acid solute.

47. The composition of any preceding claim is free of 1,4-dioxane.

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