Cleaning compositions with improved detergent compounds

Abstract

Detergent compounds formed from a sulfated or glycosylated polyol ester of fatty acid (PEFA) compound are disclosed. The detergent compounds exhibit reduced harshness, less foam generation, improved enzyme compatibility, and are less environmentally damaging. Methods of making and using the detergent compounds in cleaning compositions are further disclosed.

Description

CLEANING COMPOSITIONS WITH IMPROVED DETERGENT COMPOUNDS CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] The present application relates to U. S. Provisional Patent Application Serial Nos.63 / 898,052, filed October 13, 2025; 63 / 730,912, filed December 11, 2024, and 63 / 749,656 filed January 26, 2025, each of which are hereby incorporated by reference herein in their respective entireties.TECHNICAL FIELD

[0002] The present disclosure relates generally to cleaning compositions including detergent compounds formed from high-HLB derivatives of polyol esters of fatty acids (PEFAs) compounds. In certain embodiments, the cleaning compositions can be laundry compositions.BACKGROUND

[0003] Numerous products, including personal care products, home care products, laundry products, dishwashing products, and industrial products include detergent compounds to provide cleaning properties to a substrate. Detergent compounds have amphiphilic structures which can aggregate to form micelles which surround and remove soils from a substrate. While known detergent compounds are generally effective, known detergent compounds suffer from various drawbacks including perceived harshness when used in personal care products, undesirable foam generation when used in laundry and dishwashing applications, and production from controversial feedstocks such as palm oil. There is an unmet need for detergent compounds which have improved properties, and which can be sustainably produced.SUMMARY

[0004] According to one embodiment, a cleaning composition includes a carrier and a detergent compound. The detergent compound includes a modified polyol ester of fatty acids (“PEFA”) compound having a hydrophilic-lipophilic balance (“HLB”) value of about 10 or greater.BRIEF DESCRIPTION OF THE DRAWINGS

[0005] FIG. 1 depicts the longitudinal contact angles of an inventive detergent compound and a comparative detergent 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 “detergent compound” refers to a surface active amphiphilic compound useful for soil removal.

[0012] As used herein, the term “halogen” means F, Cl, Br, or I.

[0013] 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.

[0014] As used herein, a “polyol lipid” means a compound wherein a polyol moiety is covalently attached to a fatty acid.

[0015] 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 well known 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 PEFA compounds of this disclosure can include those derived from suitable inorganic and organic acids and bases, while pharmaceutically or biologically acceptable acids of the PEFA 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, camphorsulfonate, 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 -phenyl propionate, phosphate, pivalate, propionate, stearate, succinate, sulfate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate salts, and the like.

[0016] As used herein, “soils” include, but are not limited to, dirt, oils, food, biological contaminants, colorants, fats, and particulates such as titanium dioxide, carbon black, iron oxide, pigments, and mica.

[0017] 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).

[0018] 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.

[0019] 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.

[0020] As will be described herein, advantageous detergent compounds are disclosed. Generally, the detergent compounds can be derivatives of polyol esters of fatty acids (PEFAs) including sulfated or glycosylated PEFAs. The detergent compounds described herein can exhibit a high effective HLB value and can be better than, or equal to, known detergent compounds at soil removal while exhibiting fewer drawbacks than known detergent compounds having comparable HLB values. In certain embodiments, the detergent compounds described herein can have less irritability and less foaming than detergent compounds of similar HLB value while achieving similar or better performance even when the compounds are non-ionic as in the case of glycosylated PEFAs. The detergent compounds can reduce irritability of compositions that otherwise exhibit irritability and can boost the efficiency of enzymes allowing for lower enzyme loading. Higher foam heights can be achieved by blending the detergent compounds described herein with other known detergent compounds having higher foam. The detergent compounds can be free of 1,4-dixoane.

[0021] 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.

[0022] 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 moieties 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 of about 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.

[0023] 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 someembodiments, 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-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 lipid disclosed herein is an acetylated C18:0-3-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.

[0024] Exemplary Compounds

[0025] In some embodiments, the detergent compounds can be, or can alternatively be formed by sulfating or glycosylating certain of, the following PEFA compounds:OH O OH OHOH OH OH O OH OHOH OHOH O OH OH OH OH OH O OH OH OHP ii-OH OH OH O OH O OH OH OH O OH OH°'s° OH OH 6' °HOH O HOO2SO OSO2OH OSO2OH O HOO2SO OSO2OH and OH O OH OH OHoHOCH2OH2OH H< / ~ “bnoo oCH2OHor salt or acid thereof.

[0026] In some embodiments, the detergent compounds are PEFA compounds represented by Formula (I) or (II):(I)orR1R3O RaR2R4(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, -(C2HsO)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, -(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, -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-C3 alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;each Ryis independently -H, C1-C3 alkyl, 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; andeach p is independently selected from 1-10,whereinwhen 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;

[0027] 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.

[0028] In some embodiments, the detergent compounds 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)(C2HsO)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-C3 alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;each Ryis independently - H, C1-C3 alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;n is 2-11; andeach p is independently selected from 1-10.

[0029] In some embodiments, one or more of Rxcan comprise a sugar or sugar alcohol. In certain such embodiments, the sugar or sugar alcohol can comprise one or more of glucose, sucrose, fructose, galactose, lacstose, maltose, trehalose, cellobiose, chitobiose, dojibiose, nigerose, isomaltose, sophorose, laminarbiose, gentiobiose, trehalulose, turanose, maltulose, leucrose, isomaltulose, gentiobiulose, mannobiose, maliobiose, allolactase, melibuilose, lactulose, rutinose,rutinulose, xylobiose, erythritol, threitol, arabinose, lyxose, ribose, xylose, ribulose, xylulose, deoxyribose, arabitol, allose, altrose, glucose, mannose, gulose, idose, talose, psicose, sorbose, tagatose, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, volemitol, dedoheptulose, mannoheptulose, ethylene glycol, glycerol, isomalt, malitol, lactitol, maltotritiol, maltotetraitol, or polyglycitol. In certain embodiments, each of Rxcan comprise a sugar, sugar alcohol, or sulfate while in other embodiments, a subset of Rxcan comprise a sugar, sugar alcohol, or sulfate.

[0030] In some embodiments, the detergent compounds are PEFA compounds represented by Formula (I-a) or (Il-a):(Il-a)or salt or acid thereof,whereinn is 6-12.

[0031] 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, -(C2HsO)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)pRyIn some embodiments, R1is -P(O)(OH)2. In some embodiments, R1is -S(O2)OH. In some embodiments, R1is -(CjHkOm).

[0032] 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 -(C2HsO)pRy. In some embodiments, R2is -P(O)(OH)2. In some embodiments, R2is -S(O2)OH. In some embodiments, R2is -(CjHkOm).R3

[0033] 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, -(C2HsO)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).

[0034] 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)pRyIn some embodiments, R4is -P(O)(OH)2. In some embodiments, R4is -S(O2)OH. In some embodiments, R4is -(CjHkOm).

[0035] In some embodiments, 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, -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, R5is 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, R5is -H. In some embodiments, R3is -P(O)(OH)2, or -S(O2)OH. In some embodiments, R5is -C(O)RX. In some embodiments, R3is -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 -(C2HsO)pRy. In some embodiments, R5is -P(O)(OH)2. In some embodiments, R5is -S(O2)OH. In some embodiments, R5is -(CjHkOm).I

[0036] 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).7^

[0037] In some embodiments, each Rxis independently C1-C3 alkyl, 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.7^

[0038] In some embodiments, each Ryis independently -H or C1-C3 alkyl, wherein Ryis optionally substituted with 1-7 instances of halogen. In some embodiments, Ryis -H. In some embodiments, each Ryis independently C1-C3 alkyl, wherein Ryis optionally substituted with 1-7 instances ofhalogen. 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 Detergent compounds

[0039] 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.

[0040] In some embodiments, the detergent compounds described herein can be prepared as outlined in Scheme 1 or 2 followed by sulfation of the resulting product:Scheme 1wherein LG is a leaving group.Scheme 2OR1OR3OR1OR3O ORawherein LG is a leaving group.

[0041] In some embodiments, the detergent compounds described herein can be prepared as outlined in Scheme 3 or 4 followed by sulfation of the resulting product:Scheme 3

[0042] In some embodiments, the detergent compounds described herein can be prepared as outlined in Scheme 5 or 6 followed by sulfation:Scheme 5Scheme 6

[0043] In certain embodiments, the detergent agents described herein can be formed by reacting the PEFA compounds with sulfamic acid to replace aliphatic alcohols as depicted in the below scheme:p O9?H?"'S'CB5A A JRo 'y y NH,$O, H 1 KFC.4 hrsG^, O OHc^.,6 o, prCH31 ">xCH$ / zGO A B

[0044] In yet other certain embodiments, the detergent 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:99 OH P''~"'CH3GSO3H, AeOH. -!5" CR'' - O<xAOMCH3

[0045] 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.

[0046] 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.

[0047] The benzyl groups were cleaved using hydrogenation conditions using ethyl acetate as the solvent.

[0048] Synthesis / isolation of starting materials for the detergent agents described herein can be found in WO2018148465 and WO2017184884, each of which are incorporated in their entirety.Properties and Applications

[0049] Detergent compounds formed from the described PEFA compounds can exhibit beneficial properties compared to known detergent compounds. For example, the detergent compounds described herein can exhibit reduced harshness compared to known detergent compounds and can produce less foam than known detergent compounds. Reduction in harshness can make the detergent compounds appealing for personal care products where consumers dislike the harshness of known detergent compounds while still desiring strong cleaning properties. Reduction in foaming can facilitate use of the detergent compounds in applications such as laundry, glass cleaning, floor cleaning, and dishwashing where excess foam production can clog and / or overflow the machine.

[0050] As can be appreciated, the detergent compounds described herein can also be biologically manufactured and can exhibit more favorable safety and environmental profiles than conventional detergent compounds which are typically synthesized from petroleum feedstock and which frequently have residual 1,4-dioxane. Being a fermentation product, the detergent compounds described herein are renewable, less environmentally damaging, biodegradable, and have low-toxicity facilitating their use in applications where harsher and less environmentally friendly detergent compounds are less preferred. The detergent compounds described herein can be entirely free of 1,4-di oxane. In an embodiment, the detergent compounds after production through fermentation can be chemically modified further as described herein.

[0051] In certain embodiments, it can be particularly advantageous to use the detergent compounds described herein in conjunction with traditional detergent compounds. Such blends can enable compositions formed of such blends to exhibit synergistic benefits. For example, combination of the detergent compounds described herein with additional surfactants can exhibit high foam heights and volumes while still retaining desirable benefits such as higher performance cleaning and lower irritation. Additionally, the detergent compounds described herein can boost the efficiency of enzymes included in known cleaning compositions. In certain embodiments, the combination of the detergent compounds described herein with traditional detergents or enzymes can be particularly beneficial due to the synergies that boost the best properties of each.

[0052] In such embodiments, the additional detergents can be anionic, cationic, nonionic or amphoteric surfactants and combination thereof. Non-limiting 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 alkyl-aryl 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-dodecylamine lactate, the acetate of aminoethylaminoethyl 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 isoctylphenol 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 astetraethyl ene 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, phosphatidylserine, 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.

[0053] In certain embodiments, the detergent compounds 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 detergent compounds can react minimally with the components of a product or system in which it is introduced. In certain embodiments, the detergent compounds are present in an end product of a processing procedure. In certain embodiments, the detergent compounds are physiologically safe or have a safety profile that is biologically acceptable. In some embodiments, the detergent compounds are biodegradable and / or environmentally safe or environmentally acceptable.

[0054] The HLB value of the detergent compounds described herein can be about 10 or greater. 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 relative hydrophilicity or lipophilicity and does not indicate the amount of the detergent compound necessary to provide soilremoval. The detergent compounds described herein have been found to be effective at soil removal at lower HLB values than known detergents having similar, or higher, HLB values.

[0055] Generally, the detergent compounds described herein can be used in any application where conventional detergent compounds are utilized including, without limitation, personal care products, home care products, food products, industrial products, institutional products, coating products, construction materials, adhesives materials, oil well materials, lubricants, agricultural products, pesticidal products, and textile processing products.

[0056] For example, in certain embodiments, the detergent compounds described herein can be useful for household, industrial, and institutional (“HI& I”) cleaning compositions wherein the detergent compounds 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. The detergent compounds can be particularly suitable for dishwashing compositions and clothes washing compositions where the low foaming nature of the present detergent compounds is particularly beneficial.

[0057] Other example compositions which can include the detergent compounds described herein include personal care compositions such as personal care products, soaps, lotions, shampoos, bodywashes, cleaning pads, sunscreens, toothpastes, hygiene products, and other beauty products. The detergent compounds 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, and food processing equipment, and perfumes.

[0058] Generally, the detergent compounds described herein can be applied in dry or wet forms at any suitable concentration. For example, the concentration of the detergent compounds 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%.

[0059] The detergent compounds 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.

[0060] In certain embodiments, the detergent compounds can be used in aqueous compositions. However, or additionally, the detergent compounds 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.

[0061] In certain embodiments, a solubilizer can be included with one or more of the detergent compounds as described herein. Such suitable 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, propylene glycol 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 DOWANOL 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™, ButylPROPASOL™, 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™.

[0062] Suitable additives which can work with the detergent compounds 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.

[0063] Suitable stabilizing agents and preservatives for compositions formed from the detergent compounds described herein can include oleic acid, hexylene glycol, fatty alcohols, naphthalene sulfonates, butyl alcohol, sodium chloride, sodium benzoate, citric acid, isothiazolinones, phenoxyethanol, sorbic acid, sodium hydroxymethylglycinate, parabens, and formaldehyde.

[0064] The detergent compounds described herein can generally remove soils, such as, but not limited to, dirt, oils, food, biological contaminants, and fats.EXAMPLES

[0065] 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 the present 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.

[0066] 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.O OJ I' O O OH O' CH3. A i A J- - o yT0x,.0 O. / A AYCH3OFormula (I).

[0067] Inventive Example 2 is a glycosylated PEFA derived from a glycolipid yeast fermentation product having an HLB balance of about 10 to about 15. Inventive Example 2 has a Critical Micelle Concentration of 15.6 (mg / L); an average longitudinal contact angle on fabric (1 g / L) of 140°-130°, an interfacial tension (Ig / L) with dodecane of 0.49 and with olive oil of 0.9, a Surface Tension Value at the Critical Micelle Concentration of 33.5 (mN / M) using the Wilhelmy Plate method, and a dynamic surface tension (1 / gL) of 41 mN / m at 5 seconds. The glycosylated PEFA of Inventive Example 2 is depicted in Formula (II).O1'O O OH O,, A 1 x)' - Y A Y o' A\. 0 d..o HO.1f o. AHO Y, A OHOHFormula (II)

[0068] The longitudinal contact angle of Inventive Example 1 on WR-280 Sunbrella fabric was compared to the longitudinal contact angle of Comparative Example A. Comparative Example A is a traditional detergent compound, sodium laureth sulfate. Each of Inventive Example 1 and Comparative Example A were diluted in water to a concentration of 1 g / L and then measured using a Biolin Tensiometer which dispersed 5 uL of the test solution onto the WR-280 Sunbrella fabric. The contact angle as a measure of time are plotted in FIG. 1

[0069] As depicted in FIG. 1, the longitudinal contact angle of Inventive Example 1 is nearly identical to the longitudinal contact angle of Comparative Example A, a well known and high performing detergent compound.

[0070] Various example cleaning products were formulated to demonstrate that the detergent compounds described herein functioned equally, or better, than known detergent compounds.

[0071] Hand Soap

[0072] A hand soap was formulated as depicted in Table 1 using the sulfonated PEFA compound of Inventive Example 1.TABLE 1Component Purpose %W / WWater Water 48.4Glycerine 99.7% USP Humectant 3Xathan gum Thickener 0.5Inventive Example 1 (95% active) Cleaner 7 Lauramine oxide (30% active) Cleaner 20Sodium Chloride Thickener 6Decyl Glucoside (60% Active) Cleaner 14Sodium Benzoate Preservative 0.5Fragrance Perfume 0.5Citric Acid, Anhydrous USP Non-GMO Buffer 0.1Dish Soap

[0073] Dish soaps were formulated as depicted in Table 2 using the sulfonated PEFA compound of Inventive Example 1 as well as the glycosylated PEFA compound of Inventive Example 2.TABLE 2Formulation 1 Formulation 2 Component(wt.%) (wt.%)Water 16.1 26.9Inventive10 -- Example 1Inventive— 1.2Example 2SLS — 10Decyl Glucoside16.7 16.7(50% active)Lauramine Oxide26.7 26.7(30% active)Lauryl Glucoside12 —(50% active)

[0074] Both Formulations 1 and 2 were tested and determined to be effective dish soaps. Formulation 1 replaced SLS as the primary surfactant while Formulation 2 used Inventive Example 2 to boost the efficiency of conventional surfactants by lowering the critical micelle concentration.Hard Surface Cleaner

[0075] A hard surface cleaner was formulated as depicted in Table 3 using the sulfonated PEFA compound of Inventive Example 1. The hard surface cleaner had comparable cleaning performance as a hard surface cleaner formulated with sodium lauryl sulfate (also depicted in Table 3). Additionally, a second hard surface cleaner was formulated that used Inventive Example 2 as a booster for a known surfactant by lowering the critical micelle concentration.TABLE 3Inventive Hard Inventive HardComparative Hard Surface Cleaner (% Surface Cleaner (%Surface Cleaner (% wt.) wt.) wt.)Water 93.2 97.03 93.3 InventiveExample 1 1.6 — —(95% active)InventiveExample 2 — 0.17 —(90% active)SLS (100%— 1.5 1.5active)LaurylGlucoside 3 — 3(50% Active)Fragrance 0.2 — 0.2GLDA 1 1.3 1 Phenoxyethanol 1 — 1

[0076] Laundry Soap

[0077] To determine if Inventive Example 2 could function as a cleaner in laundry products, the stain removal performance characteristics of Inventive Example 2 were measured and compared to Triton CG-110 (an APG surfactant) and Lutensol LA-7 (a 7 mole linear alcohol ethoxylate). The strain removal performance characteristics were measured in accordance with ASTM standard D4265-14, Standard Guide for Evaluating Stain Removal Performance in Home Laundering. The test was performed with each solution containing 0.67 grams of surfactant (active) plus 2.68 grams of deionized water. Performance was determined by evaluating the difference in color before and after cleaning artificially soiled fabric swatches in a High-Efficiency Front Load Washer (Whirlpool Model WFW56CHH4) and dried. A TD-0056 Mach5+ multispectral colorimeter was used to measure the change in color. The average delta E values results on cotton, tergotometer warm water wash, are depicted in Table 4 with their standard deviation.TABLE 4Soil Inventive Ex. 2 Triton CG-110 Lutensol LA-7 Fluid make-up on cotton 3.08 (0.02) 2.51 (0.26) 3.04 (0.52) Carbon black / olive oil on1.70 (0.47) 0.54 (0.08) 2.04 (0.08) cottonRed wine on cotton 8.25 (0.28) 8.40 (0.06) 8.74 (0.01) Cocoa on cotton 3.77 (0.46) 3.43 (0.41) 3.69 (0.31) Motor oil on cotton 1.84 (0.82) 1.41 (0.15) 2.29 (0.19) Ground in clay soiled cotton 8.79 (1.46) 8.86 (1.08) 7.91 (0.21) Total Delta E 27.43 25.16 27.70

[0078] As reported in Table 4, Inventive Example 2 performed similarly to well known non-ionic and non-petroleum derived surfactants indicating that Inventive Example 2 could perform well in laundry detergents.

[0079] A laundry soap was formulated as depicted in Table 5 using the sulfonated PEFA compound of Inventive Example 1 and Inventive Example 2. Each laundry formulation had a pH between 7.5 and 8.TABLE 5Inventive Laundry Comparative Laundry ComponentFormulation (wt%) Example (wt%)Water 53.87% 54.45%Laureth-7 -- 6%Inventive6.32% —Example 2Lauryl glucoside 10% 10%SLS — 5.0%Inventive5.26% —Example 1Potassium cocoate 15% 15%Sodium citrate 3% 3%Citric acid - 50% 0.1% 0.1%Enzyme Blend 2.25% 2.25%GLDA 2% 2%Glycerin 2% 2%Calcium Chloride 0.1% 0.1%Methyl0.1% 0.1%isothiazolinone

[0080] The performance of the laundry soaps of Table 4 was evaluated in accordance with ASTM standard D4265-14 as previously described.

[0081] The Strain Removal Index of the Inventive Laundry Formulation and the Comparative Laundry Formulation are depicted in Table 6.TABLE 6Inventive Laundry Std. Comparative Laundry Std. SoilFormulation Dev. Formulation Dev.Ground in clay soiled36.82 0.69 30.84 0.71 cottonRed wine on cotton 37.24 0.72 39.79 0.12 Cocoa on cotton 11.38 4.1 15.31 3.01 Fluid make-up on cotton 7.93 0.32 13.59 0.91 Motor oil with carbon5.16 1.92 5.45 0.21 black on cottonCarbon black / olive oil on2.12 0.42 4.3 1.53 cotton

[0082] As depicted in Table 6, the Inventive Laundry Formulation performed similarly to the Comparative Laundry Formulation at removing soils demonstrating the cleaning abilities of the Inventive Examples.

[0083] Additional laundry soaps were also formulated with Inventive Example 2 as depicted in Table 7. The additional laundry soaps replace lauryl glucoside with Inventive Example 2.TABLE 7Comparative Comparative Inventive Inventive Component Formulation 1 Formulation 2 Formulation 3 Formulation 4(wt%) (wt%) (wt%) (wt%) Water 42.8 45 47.8 50 Laureth-7 6 6 6 6 Lauryl glucoside 10 10 0 0 Sodium 2-methyl13.6 13.6 13.6 13.6 sulfolauratePotassium cocoate 15 15 15 15 Sodium citrate 3 3 3 3 ProteaseAmylase4.5 2.25 4.5 2.25 MannanaseLipaseGLDA 2 2 2 2 Glycerin 2 2 2 2 Calcium Chloride 1 1 1 1 Methyl0.1 0.1 0.1 0.1 isothiazolinoneInventive Example0 0 5 5 2

[0084] The performance of the laundry soaps of Table 7 was also evaluated in accordance with ASTM standard D4265-14. The Strain Removal Index of the Inventive Laundry Formulation and the Comparative Laundry Formulation are depicted in Table 8.TABLE 8Comparative Comparative Inventive Inventive StainFormulation 1 Formulation 2 Formulation 3 Formulation 4 Red Wine 16.85 17.11 17.11 17.60 Blackcurrant juice,26.77 26.99 26.90 27.39 agedTea for bleach 0.45 0.44 0.48 0.50 Coffee for bleach 0.60 0.65 0.58 0.53 Rice starch, colored 31.77 24.75 29.17 22.01 Com starch,31.09 24.71 30.82 22.93 coloredSalad dressing with12.34 12.13 12.51 11.81 natural blackLocust bean gum20.53 19.88 20.55 19.26 with pigmentOatmeal, coloredwith chocolate, 18.55 20.26 19.95 19.33 agedEgg yolk with19.51 18.70 18.02 16.76 carbon black, agedBlood, aged 19.24 22.86 21.68 18.14 Blood, milk, ink 20.51 19.52 20.30 18.18 Grass, extract 6.97 7.52 6.74 7.15 Cocoa, aged 10.35 10.75 9.92 9.75 Pigment, oil, milk 8.86 8.39 8.35 7.81 Olive oil withcarbon black and 14.19 15.40 14.48 14.29 thickening agentHigh discriminative9.21 9.45 8.32 8.42 sebumFluid make-up 8.23 8.92 8.78 8.22 Lipstick, diluted,23.70 24.83 24.04 24.54 redTotal SRI 299.71 293.26 298.78 274.64

[0085] As depicted in Table 8, the inventive formulations including Inventive Example 2 matched the performance of laundry soaps formulated with lauryl glucoside despite being included at a lower loading level.Laundry Soap Exclusive of Petroleum -Derived Surfactants

[0086] Additional laundry soaps were formulated that replaced all petroleum-derived surfactants (including sodium laureth sulfate (“SLES”) and linear alkyl benzene sulfonates (“LAS”)) with the biologically derived surfactant of Inventive Example 1. Table 9 depicts the laundry soap of Inventive Formulation 5 using only Inventive Example 1 as a surfactant as well as a Comparative Formulation 3 which is formulated using the conventional (and petroleum-derived) surfactants SLES and LAS. Inventive Formulation 5 is a 1:1 replacement of the surfactants (at active levels) of Comparative Formulation 3.TABLE 9Comparative Inventive Component Formulation 3 Formulation 5(wt%) (wt%) Sodium and MEA C10-C16 Alkylbenzene Sulfonate —7(LAS)Sodium Laureth Sulfate (SLES) 8.5 — C10-C16 Pareth 6 6 Cl 0-16 Alkyldimethylamine Oxide 4.25 4.25 Inventive Example 1 (30% active) — 35.48 Sodium Citrate 3 3 Citric acid, 50% to adjust pH as needed — — Enzyme 3 3 Preservative M20 (MIT) 0.1 0.1 Water 68.15 48.17

[0087] Each of Inventive Formulation 5; Comparative Formulation 3; and a commercial laundry soap, Gain + Aroma Boost Original Scent HE Compatible Liquid Laundry Detergent Soap, ItemNumber (DPCI) 003-08-8674 marketed by Procter & Gamble (Cincinnati, OH), were evaluated for stain removal in accordance with ASTM standard D4265-14. The Strain Removal Index of each of the laundry soaps are depicted in Table 10.TABLE 10Commercial Inventive Comparative Laundry Soap Formulation 5 Formulation 3Cocoa, aged 27.99 27.92 28.68Fluid make-up 28.51 27.68 30.24Grass, extract 29.91 28.86 31.48High discriminative sebum 26.97 28.69 25.46BEY with pigmentLipstick, diluted, red 36.39 38.19 39.24Olive oil with carbon black, 36.72 39.70 37.70with thickening agentPigment, Oil, Milk (POM) 26.85 25.45 26.83Total SRI 213 216 220

[0088] As depicted in Table 10, Inventive Formulation 5 performs similarly to both the commercial laundry soap and Comparative Formulation 3 despite being free of any conventional surfactants. As can be further appreciated, Inventive Formulation 5 is also expected to exhibit lower foam heights as the detergent compounds described herein generally exhibit lower foaming than known surfactants. Lower foam heights can improve compatibility with high efficiency washing machines which require low foam to operate. Additionally, lower foaming can reduce the amount of water used by a washing machine as it facilitates removal of the laundry soap with less rinse water.Foaming Hand Soap

[0089] A foaming hand soap was formulated as depicted in Table 11 using the sulfonated PEFA compound of Inventive Example 1 as well as the glycosylated PEFA of Inventive Example 2. The foaming hand soap had a pH of 5.2.TABLE 11Description % wt.Water 80.96Sodium citrate tribasic dihydrate / GLDA 0.3Inventive Example 1 9Fragrance 0.5Sodium Benzoate 0.55Citric Acid / NaOH 0.1Glycerin 2Lauryl Glucoside 6.39Inventive Example 2 0.2

[0090] Automatic Dishwasher Compositions

[0091] Automatic dishwasher compositions were formed using Inventive Example 2. The automatic dishwasher compositions depicted in Table 12 include formulations formed with two loading levels of enzymes. The comparative formulations include a bio-based surfactant, D-Glucopyranose, oligomeric, C10-16-alkyl glycosides, which are replaced by Inventive Example 2.TABLE 12Comp. Comp. Inv. Inv. Inv. Inv. Inv. Inv. Form. Form. Form. Form. Form. Form. Form. Form. Component1 2 1 2 3 4 5 6 (wt%) (wt%) (wt%) (wt%) (wt%) (wt%) (wt%) (wt%) Water 76 72.9 76 72.9 73.4 74.4 75.4 76.2 Calcium0 0.1 0 0.1 0.1 0.1 0.1 0.1 ChlorideTriton M20 20 20 20 20 20 20 20 (40%)SLS needles 1 1 1 1 1 1 1 1 D- Glucopyranose,oligomeric, 2 2 — — — — — — C10-16-alkylglycosidesInventive— — 2 2 2 2 2 2 Example 2Protease — 2 — 2 1 1 1 1 Amylase — 1 — 1 0.5 0.5 0.5 0.5 Xanthan Gum 1 1 1 1 1 1 1 1

[0092] The dishwashing formulations were evaluated in accordance with ASTM D3556-85 to evaluate deposition on glassware during mechanical dishwashing. A score of 1 includes no spots or no filming; a score of 2 indicates spots at random or barely perceptible filming; a score of 3 indicates about 25% of the surface has spotting or slight filming; a score of 4 indicates about ’A of the surface is spotted or moderate filming; and a score of 5 indicates virtually the entire surface is spotted or heavy filming. The results are depicted in Table 13.TABLE 13Spotting FilmingComparative Formulation 1 2.6 3.1Comparative Formulation 2 1.5 3.2Inventive Formulation 1 2.4 3.2Inventive Formulation 2 1.6 3.1Inventive Formulation 3 1.0 3.2Inventive Formulation 4 1.0 3.1Inventive Formulation 5 1.5 3.2Inventive Formulation 6 1.5 3.2

[0093] As depicted in Table 13, the addition of the Inventive PEFA compounds drastically reduced spotting of the glassware while maintaining similar filming even when reduced amounts of enzymes were included.Foam Volume

[0094] The amount of foam generated by detergent compounds can be important. For example, it is desirable for detergent compounds to generate low foam for laundry and automatic dishwashing applications where high foam can clog or overflow the machine. Conversely, manual applications benefit from greater amounts of foam.

[0095] The amount of foam volume generated was experimentally evaluated in accordance with ASTM standard D1173 for Inventive Example 1, and Comparative Examples 1-3. Comparative Example 1 is sodium lauryl sulfate, Comparative Example 2 is lauryl glucoside; and Comparative Example 3 is decyl glucoside. Inventive Example 1 was further evaluated in a 50:50 ratio of Inventive Example 1 to Comparative Example 3. The results are depicted in Table 14.TABLE 14Foam Volume (mL)Inventive Example 1 30Comparative Example 1 45Comparative Example 2 25Comparative Example 3 4050:50 Ratio of Inventive 45Example 1 to ComparativeExample 3

[0096] As depicted in Table 14, Inventive Example 1 exhibited less foam than detergent compounds of similar HLB value. However, combination of Inventive Example 1 with another detergent compound restored the foam volume. Such properties indicate that the detergent compounds disclosed herein can advantageously be used in low foam applications or, by use in combination with other detergent compounds, be used in high foam applications as well.

[0097] Additional foam testing was performed to compare Inventive Example 1, Inventive Example 2, and SLES. In the additional testing, Inventive Example 1 was found to have a foaming volume of 69 mL, Inventive Example 2 had a foaming volume of 58 mL, and SLES had a foaming volume of 120 mL indicating that both of the Inventive Examples had considerably less foam generation than conventional surfactants.Repeated Insult Patch Test

[0098] To determine the dermal irritability or induced sensitization of the detergent compounds described herein, Inventive Example 1 was evaluated using a Repeated Insult Patch Test. In the evaluation, a sample of Inventive Example 1 was diluted to 1% using deionized water and then placed onto a semi-occlusive patch. The patches were then applied to 60 human subjects aging from 19 years of age to 70 years of age for both Induction and Challenge Phases in accordance with Eurofins clinical study protocol CL 1.02022 (Eurofins | CRL, Inc., Piscataway, NJ).

[0099] No subjects had any visible skin reaction to any of Induction or Challenge Phases indicating that Inventive Example 1 has very low skin irritability. It is expected that InventiveExample 1 can reduce the irritability of compositions that would otherwise be irritating as a consequence of its very low skin irritability.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] Section and table headings are not intended to be limiting.

[0106] 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.

[0107] 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.

[0108] 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 cleaning composition comprising:a carrier; anda detergent compound comprising a derivatized polyol ester of fatty acids (“PEFA”) compound having a hydrophilic-lipophilic balance (“HLB”) value of about 10 or greater.

2. The cleaning composition of claim 1, wherein the derivatized 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-C3 alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;each Ryis independently -H, or C1-C3 alkyl, 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; andeach p is independently selected from 1-10,whereinwhen 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; and wherein one or more of R1, R2, R3, R4, R3, and Raare -S(O2)OH, -(O)S(O2)OH, or - (CjHkOm).

3. The cleaning 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, -(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);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-C3 alkyl, wherein Rxis optionally substituted with 1-7 instances of halogen;each Ryis independently -H, or C1-C3 alkyl, 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; andeach p is independently selected from 1-10.

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

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

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

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

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

9. The cleaning composition of claim 5, wherein the derivatized PEFA compound is:o o10. The cleaning composition of claim 5, wherein the derivatized PEFA compound is an ammonium salt.

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

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

13. The cleaning composition of claim 12, wherein the derivatized PEFA compound is glycosylated.

14. The cleaning composition of claim 13, wherein one or more of R1, R2, R3, R4, R5, and Racomprise a derivatized sugar or derivatized sugar alcohol.

15. The cleaning composition of any claim 13, wherein one or more of R1, R2, R3, R4, R5, and Racomprise deprotonated forms of sugars and sugar alcohols including one or more of glucose, sucrose, fructose, galactose, lacstose, maltose, trehalose, cellobiose, chitobiose, dojibiose, nigerose, isomaltose, sophorose, laminarbiose, gentiobiose, trehalulose, turanose, maltulose, leucrose, isomaltulose, gentiobiulose, mannobiose, maliobiose, allolactase, melibuilose, lactulose, rutinose, rutinulose, xylobiose, erythritol, threitol, arabinose, lyxose, ribose, xylose, ribulose, xylulose, deoxyribose, arabitol, allose, altrose, glucose, mannose, gulose, idose, talose, psicose, sorbose, tagatose, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, volemitol, dedoheptulose, mannoheptulose, ethylene glycol, glycerol, isomalt, malitol, lactitol, maltotritiol, maltotetraitol, or polyglycitol.

16. The cleaning composition of claim 13, wherein the sugar moiety comprises D-mannitol or D-arabitol.

17. The composition of claim 13, wherein the derivatized PEFA compound is one or more of:oHOOH / " OHCH2OHor salt or acid thereof.

18. The composition of claim 13, wherein the derivatized PEFA compound is one or more of:o oCH2OHor salt or acid thereof.

19. The cleaning 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.

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

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

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

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

24. The cleaning composition of claim 23, wherein at least one of the one or more additional PEFA compounds or derivatized PEFA compounds has an HLB of less than 10.

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

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

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

28. The cleaning composition of any preceding claim exhibits a foam height of about 45 mb or greater when combined in a 50:50, by weight, ratio with decyl glucoside when measured in accordance with ASTM DI 173.

29. The cleaning composition of any one of claims 1 to 28 is a personal care product.

30. The cleaning composition of any one of claims 1 to 28 is a dishwashing product.

31. The cleaning composition of any one of claims 1 to 28 is a laundry product.

32. The laundry product of claim 32, wherein the laundry product is free of any petroleum-derived surfactants.

33. The laundry product of claim 31 or claim 32, wherein the laundry product exhibits low foaming and is a high efficiency laundry product.

34. The laundry product of any of claims 31 to 33, wherein the laundry product exhibits comparable stain removal to a similar laundry product comprising sodium laureth sulfate and lauryl alkylbenzene sulfonates.

35. The cleaning composition of any one of claims 1 to 28 is a surface cleaning product.

36. The cleaning composition of claim 35 is a hard surface cleaner, a glass cleaner, a multisurface cleaner, a floor cleaner, a carpet cleaner, a shower or tub cleaner, a wall cleaner, a plastic cleaner, a metal cleaner, a cookware cleaner, a lens cleaner, or a screen cleaner.

37. The cleaning composition of any one of claims 1 to 28 is a textile cleaner.

38. The cleaning composition of any one of claims 1 to 28 is a household, industrial, or institutional cleaning product.

39. The cleaning composition of any one of claims 1 to 28 is an electronics cleaner.

40. The cleaning composition pf claim 39 is a printed circuit board cleaner.

41. The cleaning composition of any one of claims 1 to 28 is a photolithography cleaner.

42. The cleaning composition of any one of claims 1 to 28 is an oral care cleaner.

43. The cleaning composition of any one of claims 1 to 28 is an automobile cleaner or an aerospace cleaner.

44. The cleaning composition of any one of claims 1 to 28 is a hospital or nursing care cleaner.

45. The cleaning composition of any one of claims 1 to 28 is a food contact surface cleaner.

46. The cleaning composition of any one of claims 1 to 28 is a plumbing cleaner.

47. The cleaning composition of any one of claims 1 to 28 is a sterilization or disinfectant cleaner.

48. The cleaning composition of any preceding claim is an aqueous composition.

49. The cleaning composition of any preceding claim, wherein the derivatized PEFA compound is free of 1,4-dioxane.

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

51. The cleaning composition of any preceding claim, wherein the derivatized PEFA compound is not derived from palm oil.

52. The cleaning composition of any preceding claim is free of any compounds derived from palm oil.

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