Surfactants with PEFA compounds and methods of use thereof

Abstract

Disclosed herein are fatty acid polyol esters (PEFAs) and their use as surfactants, methods of making and compositions thereof.

Description

[0001] Citation of Related Applications

[0002] This application claims priority to U.S. Provisional Patent Application Serial No. 63 / 365,404, filed on May 26, 2022, entitled “Compounds, Compositions, and Methods of Use Thereof”; U.S. Provisional Patent Application Serial No. 63 / 365,405, filed on May 26, 2022, entitled “Polyol Ester of Fatty Acids (PEFAs) as Antifoam”; and U.S. Provisional Patent Application Serial No. 63 / 365,406, filed on May 26, 2022, entitled “Polyol Ester of Fatty Acids (PEFAs) as Emulsifiers”; and the entire contents of these provisional applications are hereby incorporated by reference into this document. Technical Field

[0003] The present disclosure relates to polyol fatty acid esters (PEFAs), their use as surfactants, methods of preparation and compositions thereof. Background Art

[0004] PEFA compounds can have a variety of uses, including use as surfactants. Surfactants (both petroleum-based and bio-based) are examples of compounds that can be used as emulsifiers, detergents, dispersants, conventional foam control agents and wetting agents for a wide variety of consumer applications, including agricultural, nutritional, cosmetic, veterinary, therapeutic, paints, inks and industrial applications. However, such surfactants may exhibit poor performance in terms of sustainability, bioaccumulation, ecotoxicity and / or biodegradability.

[0005] Therefore, there is a need to develop alternative surfactants and compositions to improve the formulation of consumer products in these applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0006] Figure 1 is a graph depicting the critical micelle concentration versus surface tension for sodium dodecyl sulfate as a surfactant.

[0007] Figure 2 is a graph depicting critical micelle concentration versus surface tension for a combination of sodium lauryl sulfate and PEFA (60:40 ratio) as surfactants. DETAILED DESCRIPTION

[0008] Fatty acid polyol esters are amphiphilic molecules comprising sugar alcohols esterified with the carboxyl end of a 3-hydroxy fatty acyl moiety, such as D-mannitol and / or D-arabitol, which may or may not be acetylated. The non-esterified hydroxyl groups of the sugar alcohols may or may not be acetylated. In some embodiments, the one or more polyol lipids produced are mixtures of similar compounds containing (R)-3-hydroxy fatty acyl moieties with different chain lengths, ranging from about 8 to 24 carbons, preferably from 12 to 20 carbons. In some embodiments, the (R)-3-hydroxy fatty acyl moieties may present varying degrees of unsaturation ranging from about 0 to 6, for example, in the range of between 2 and 5. In some embodiments, the non-esterified hydroxyl groups of the sugar alcohols may be esterified with acetyl groups. In some embodiments, the sugar alcohols may be fully acetylated. In some embodiments, the sugar alcohols may be non-acetylated. In some embodiments, acetylation may be between these two states.

[0009] The present disclosure particularly includes compounds represented by the formula:

[0010]

[0011] (II)

[0012] or its salts or acids,

[0013] Where R 1 , R 2 , R 3 , R 4 , R 5 , R a and a are defined herein.

[0014] definition

[0015] In this disclosure, the following terms have the following meanings:

[0016] The term "about" preceding a number includes plus or minus 10% or less of the numerical value. It is to be understood that the value referred to by the term "about" itself is also specifically and preferably disclosed.

[0017] The term "alkyl" refers to a straight or branched chain alkyl group. Exemplary alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.

[0018] The term "halogen" refers to F, Cl, Br or I.

[0019] As used herein, the term "surfactant combination" refers to a surfactant comprising PEFA and at least one other surfactant, ie a surfactant mixture comprising one or more surfactants formed from PEFA compounds and one or more surfactants formed from non-PEFA compounds.

[0020] As used herein, the term "salt or acid thereof" refers to any salt or acid of a PEFA compound. Exemplary salts and acids of PEFA compounds are suitable for use in contact with tissues of humans and lower animals without excessive toxicity, irritation, allergic response, and the like, and are commensurate with a reasonable benefit / risk ratio. Salts may include pharmaceutically or biologically acceptable salts. Likewise, acids may include pharmaceutically or biologically acceptable acids. Pharmaceutically or biologically acceptable salts and acids are well known in the art. For example, SM Berge et al. describe pharmaceutically or biologically acceptable salts in detail in J. Pharmaceutical Sciences, 1977, 66, 1-19, which is incorporated herein by reference. Pharmaceutically or biologically acceptable salts of the compounds of the present disclosure may include those derived from suitable inorganic and organic acids and bases, and pharmaceutically or biologically acceptable acids of the compounds of the present disclosure may include suitable inorganic and organic acids. Examples of pharmaceutically or biologically acceptable inorganic acids may include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid and perchloric acid, or using 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 amino groups formed with such inorganic acid examples. Another example of a pharmaceutically or biologically acceptable acid is a carboxylic acid, wherein the carboxylated form 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, dodecylsulfate, ethanesulfonate, formate, fumarate, glucoheptonate, glycerophosphate, gluconate, hemisulfate, 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, and the like.

[0021] Salts derived from appropriate bases include alkali metal, alkaline earth metal, ammonium and N(C 1-4 alkyl)4 Salts. Representative alkali metal or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium, and the like. Other pharmaceutically or biologically acceptable salts include ammonium, quaternary ammonium, and amine cations formed using counterions, such as halides, hydroxides, carboxylates, sulfates, phosphates, nitrates, lower alkyl sulfonates, and aryl sulfonates, as appropriate.

[0022] The present disclosure includes both the (R) configuration and the (S) configuration at each stereocenter, even when drawn as defined or undefined. In addition, the present disclosure includes racemic compositions of the compounds disclosed herein. The present disclosure includes scalemic compositions of the compounds disclosed herein. The present disclosure includes enantiomerically enriched compositions of the compounds disclosed herein.

[0023] PEFA compounds

[0024] Disclosed herein are compounds formed from one or more polyol fatty acid esters (PEFAs) that can provide enhanced benefits to personal care products and other consumer products.

[0025] Fatty acid polyol esters are amphiphilic molecules comprising sugar alcohols esterified with the carboxyl end of a 3-hydroxy fatty acyl moiety, such as D-mannitol and / or D-arabitol, which may or may not be acetylated. The non-esterified hydroxyl groups of the sugar alcohols may or may not be acetylated. In some embodiments, the one or more polyol lipids produced are mixtures of similar compounds containing (R)-3-hydroxy fatty acyl moieties with different chain lengths, ranging from about 8 to 24 carbons, preferably from 12 to 20 carbons. In some embodiments, the (R)-3-hydroxy fatty acyl moieties may present varying degrees of unsaturation ranging from about 0 to 6, for example, in the range of between 2 and 5. In some embodiments, the non-esterified hydroxyl groups of the sugar alcohols may be esterified with acetyl groups. In some embodiments, the sugar alcohols may be fully acetylated. In some embodiments, the sugar alcohols may be non-acetylated. In some embodiments, acetylation may be between these two states.

[0026] In some embodiments, the polyol lipids disclosed herein are acetylated C12:0-3-hydroxy fatty acids esterified with D-arabinitol with 3 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C14:0-3-hydroxy fatty acids esterified with D-mannitol with 4 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-mannitol with 2 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-arabinitol with 2 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C14:0-3-hydroxy fatty acids esterified with D-arabinitol with 4 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C14:0-3-hydroxy fatty acids esterified with D-mannitol with 5 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-mannitol with 3 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-arabinitol with 3 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-mannitol with 4 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C18:0-3-hydroxy fatty acids esterified with D-mannitol with 2 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-mannitol with 5 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C16:0-3-hydroxy fatty acids esterified with D-mannitol with 4 acetylations. In some embodiments, the polyol lipid is an acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol with 2 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified with D-mannitol with 5 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified with D-arabinitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified with D-arabinitol with 3 acetylations.In some embodiments, the polyol lipids disclosed herein are acetylated C18:0-3-hydroxy fatty acids esterified with D-mannitol with 5 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C18:0-3-hydroxy fatty acids esterified with D-arabinitol with 4 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C20:0-3-hydroxy fatty acids esterified with D-mannitol with 3 acetylations. In some embodiments, the polyol lipids disclosed herein are acetylated C20:0-3-hydroxy fatty acids esterified with D-mannitol with 4 acetylations.

[0027] In some exemplary embodiments, the PEFA compound may be represented by the following formula:

[0028]

[0029]

[0030] or its salts or acids,

[0031] in

[0032] R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH, -COOH, -NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C jH k O m );

[0033] R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H 2j-1 O j-1 )、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0034] R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k Om )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0035] R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0036] R 5 Selected from the group consisting of: -H, -C(O)R x, -R x , -C(O)OR y , -C(O)N(H)R y , -(C 2 H 5 O) p R y , -P(O)(OH) 2 , -S(O 2 )OH, -NO 2 , -NH 2 , -(C j H k O m ), -OH, -(O)C(O)R x , -(O)R x , -(O)C(O)OR y , -(O)C(O)N(H)R y , -(O)(C 2 H 5 O) p R y , -(O)P(O)(OH) 2 , -(O)S(O 2 )OH, -(O)NO 2 , -(O)NH 2 , -(O)(C j H k O m ;

[0037] R a is selected from the group consisting of: -H, -C(O)R x , -R x , -C(O)OR y , -C(O)N(H)R y , (C 2 H 5 O) p R y , -P(O)(OH) 2 , -S(O 2 )OH, -NO 2 , -NH 2 , -(C j H k O m ), -OH, -(O)C(O)R x , -(O)R x , -(O)C(O)OR y , -(O)C(O)N(H)R y , -(O)(C 2 H 5 O)p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0038] Each R x Independently for C 1 -C 3 Alkyl, where R x Optionally substituted with 1-7 halogens;

[0039] Each R y independently -H, C 1 -C 3 Alkyl, where R x Optionally substituted with 1-7 halogens;

[0040] n is 2-20;

[0041] j is 2-12;

[0042] k is 4-26;

[0043] m is 1-16; and

[0044] Each p is independently selected from 1-10,

[0045] in

[0046] When n is 12 or 14 and R 1 When it is -OH or -(O)Ac, then R a is not -(O)Ac or -(O)Me;

[0047] When n is 12 and R a When it is -OH, then R 2 is not -OH; or

[0048] When n is 12 or 14, R a Yes -OH, R 2 Yes -OH, R 3 is -OH, and R 4 When it is -OH, then R 1 Yes(O)R x or -(O)(C 2 H 5 O) p R y ;

[0049] When n is 12 or 14, R1 Yes-(O)S(O 2 )OH,R 2 Yes-(O)S(O 2 )OH,R 3 Yes-(O)S(O 2 )OH,R 4 Yes-(O)S(O 2 )OH, and R 5 Yes-(O)S(O 2 )OH, then R a Yes-(O)C(O)R x , R x 、-(O)C(O)OR x 、-(O)C(O)N(H)R x 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 or -(O)S(O 2 )OH.

[0050] In some embodiments of formula (I) or (II),

[0051] R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH, -COOH, -NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO2 、-(O)NH 2 、-(O)(C j H k O m );

[0052] R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0053] R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k Om )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0054] R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0055] R 5 Selected from the group consisting of: -H, -C(O)R x, -R x , -C(O)OR y , -C(O)N(H)R y , -(C 2 H 5 O) p R y , -P(O)(OH) 2 , -S(O 2 )OH, -NO 2 , -NH 2 , -(C j H k O m ), -OH, -(O)C(O)R x , -(O)R x , -(O)C(O)OR y , -(O)C(O)N(H)R y , -(O)(C 2 H 5 O) p R y , -(O)P(O)(OH) 2 , -(O)S(O 2 )OH, -(O)NO 2 , -(O)NH 2 , -(O)(C j H k O m );

[0056] R a is selected from the group consisting of: -H, -C(O)R x , -R x , -C(O)OR y , -C(O)N(H)R y , -(C 2 H 5 O) p R y , -P(O)(OH) 2 , -S(O 2 )OH, -NO 2 , -NH 2 , -(C j H k O m ), -OH, -(O)C(O)R x , -(O)R x , -(O)C(O)OR y , -(O)C(O)N(H)R y , -(O)(C 2 H 5 O)p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m );

[0057] Each R x Independently for C 1 -C 3 Alkyl, where R x Optionally substituted with 1-7 halogens;

[0058] Each R y independently -H, C 1 -C 3 Alkyl, where R x Optionally substituted with 1-7 halogens;

[0059] n is 2-11;

[0060] j is 2-12;

[0061] k is 4-26;

[0062] m is 1-16; and

[0063] Each p is independently selected from 1-10.

[0064] In some embodiments, the PEFA compound may be further represented by formula (Ia) or (II-a):

[0065]

[0066] or its salts or acids,

[0067] in

[0068] n is 6-12.

[0069] In some embodiments, R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2)OH, -COOH, -NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R 1 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2 )OH. In some embodiments, R 1 is -H. In some embodiments, R 1 Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 1 Yes-C(O)R x In some embodiments, R 1 is -Ac. In some embodiments, R 1 Yes-R x In some embodiments, R 1 Yes-C(O)OR y In some embodiments, R 1 Yes -C(O)N(H)R y In some embodiments, R 1 Yes-(C 2 H 5 O) p R y In some embodiments, R1 Yes -P(O)(OH) 2 In some embodiments, R 1 Yes-S(O 2 )OH. In some embodiments, R 1 Yes-(C j H k O m ).

[0070] In some embodiments, R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R 2 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2)OH. In some embodiments, R 2 is -H. In some embodiments, R 2 Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 2 Yes-C(O)R x In some embodiments, R 2 is -Ac. In some embodiments, R 2 Yes-R x In some embodiments, R 2 Yes-C(O)OR y In some embodiments, R 2 Yes -C(O)N(H)R y In some embodiments, R 2 Yes-(C 2 H 5 O) p R y In some embodiments, R 2 Yes -P(O)(OH) 2 In some embodiments, R 2 Yes-S(O 2 )OH. In some embodiments, R 2 Yes-(C j H k O m ). In some embodiments, R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p Ry 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R 3 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2 )OH. In some embodiments, R 3 is -H. In some embodiments, R 3 Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 3 Yes-C(O)R x In some embodiments, R 3 is -Ac. In some embodiments, R 3 Yes-R x In some embodiments, R 3 Yes-C(O)OR y In some embodiments, R 3 Yes -C(O)N(H)R y In some embodiments, R 3 Yes-(C 2 H 5 O) p R y In some embodiments, R 3 Yes -P(O)(OH) 2 In some embodiments, R 3 Yes-S(O 2 )OH. In some embodiments, R 3 Yes-(C j H k O m ). In some embodiments, R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)ORy 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R 4 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2 )OH. In some embodiments, R 4 is -H. In some embodiments, R 4 Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 4 Yes-C(O)R x In some embodiments, R 4 is -Ac. In some embodiments, R 4 Yes-R x In some embodiments, R 4 Yes-C(O)OR y In some embodiments, R4 Yes -C(O)N(H)R y In some embodiments, R 4 Yes-(C 2 H 5 O) p R y In some embodiments, R 4 Yes -P(O)(OH) 2 In some embodiments, R 4 Yes-S(O 2 )OH. In some embodiments, R 4 Yes-(C j H k O m ). In some embodiments, R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R 5 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2 )OH. In some embodiments, R 5 is -H. In some embodiments, R 5 Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 5 Yes-C(O)R x In some embodiments, R 5 is -Ac. In some embodiments, R 5 Yes-R x In some embodiments, R 5 Yes-C(O)OR y In some embodiments, R 5 Yes -C(O)N(H)R y In some embodiments, R 5 Yes-(C 2 H 5 O) p R y In some embodiments, R 5 Yes -P(O)(OH) 2 In some embodiments, R 5 Yes-S(O 2 )OH. In some embodiments, R 5 Yes-(C j H k O m ). In some embodiments, R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 、-S(O 2 )OH、-NO 2 、-NH 2 、-(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C 2 H 5 O) p R y 、-(O)P(O)(OH) 2 、-(O)S(O 2 )OH、-(O)NO 2 、-(O)NH 2 、-(O)(C j H k O m ). In some embodiments, R a Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C 2 H 5 O) p R y 、-P(O)(OH) 2 and -S(O 2 )OH. In some embodiments, R a is -H. In some embodiments, R a Yes -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R a Yes-C(O)R x In some embodiments, R a is -Ac. In some embodiments, R a Yes-R x In some embodiments, R a Yes-C(O)OR y In some embodiments, R a Yes -C(O)N(H)R y In some embodiments, R a Yes-(C 2 H 5 O) p R y In some embodiments, R a Yes -P(O)(OH) 2 In some embodiments, R a Yes-S(O 2 )OH. In some embodiments, R a Yes-(C j H kO m ).

[0071] In some embodiments, each R x Independently for C 1 -C 3 Alkyl, where R x Optionally substituted with 1-7 halogens. x is a methyl group, where R x Optionally substituted with 1-7 halogens. x is ethyl, where R x Optionally substituted with 1-7 halogens. x is n-propyl, where R x Optionally substituted with 1-7 halogens. x is isopropyl, where R x Optionally substituted with 1-7 halogens. x In some embodiments, R x In some embodiments, R x In some embodiments, R x It is isopropyl.

[0072] In some embodiments, each R y independently -H or C 1 -C 3 Alkyl, where R y Optionally substituted with 1-7 halogens. y is -H. In some embodiments, each R y Independently for C 1 -C 3 Alkyl, where R y Optionally substituted with 1-7 halogens. y is a methyl group, where R y Optionally substituted with 1-7 halogens. y is ethyl, where R y Optionally substituted with 1-7 halogens. y is n-propyl, where R y Optionally substituted with 1-7 halogens. y is isopropyl, where R y Optionally substituted with 1-7 halogens. y In some embodiments, R y In some embodiments, Ry In some embodiments, R y It is isopropyl.

[0073] The present disclosure includes PEFA compounds represented by the following formula:

[0074]

[0075] or its salts or acids.

[0076] The following are examples of specific embodiments of the invention described in the present disclosure. The examples are provided for illustrative purposes only and are not intended to limit the scope of the invention in any way. The groups mentioned in the following examples, such as OR 1 , OR 2 etc., refer to the corresponding groups described herein, such as R 1 , R 2 etc., and may be replaced by any group provided in the respective corresponding group, i.e., without "O". Efforts have been made to ensure accuracy with respect to numbers used (eg, amounts, temperature, etc.), but some experimental error and deviation should, of course, be allowed for.

[0077] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 1 or 2:

[0078] Solution 1

[0079]

[0080] Where LG is a leaving group.

[0081] Solution 2

[0082]

[0083] Where LG is a leaving group.

[0084] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 3 or 4:

[0085] Solution 3

[0086]

[0087] Solution 4

[0088]

[0089] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 5 or 6:

[0090] Solution 5

[0091]

[0092] Solution 6

[0093]

[0094] The synthesis / isolation of the starting materials for the compounds described herein can be found in WO2018148465 and WO2017184884, each of which is incorporated in its entirety. An example of the synthesis of 3-hydroxy-dodecanoic acid 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl ester is provided below.

[0095] Synthesis of 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl 3-hydroxy-dodecanoate

[0096]

[0097] D-mannitol and P 2 O 5 Heat neat at 100°C for 6 hours. For example, D-mannitol 1-phosphate can be prepared as outlined in J.-G. Nam et al., Materials Chemistry and Physics 116 (2009) 46-51. D-mannitol 1-phosphate and 3-hydroxydodecanoic acid are reacted in p-toluenesulfonic acid in N 2 and heated at 170°C for 4 hours as outlined by Wenyuan Han et al. in Polymers 11, (2019), 1031.

[0098] Surfactants

[0099] Surfactants are surface-active compounds. They usually have a polar head group and a non-polar hydrocarbon chain. The polar part of the molecule can interact with polar solvents such as water, so it is also called the hydrophilic part. On the other hand, the non-polar part can interact with non-polar solvents such as oils, so it is also called the lipophilic or hydrophobic part. There are four basic types of surfactants: anionic surfactants, cationic surfactants, zwitterionic surfactants and non-ionic surfactants.

[0100] Surfactants are amphiphilic molecules that are widely used in consumer products, industrial processes, and biological applications. A key property of surfactants is the critical micelle concentration (CMC), which is the concentration at which surfactant molecules begin to aggregate into clusters. Micelles consist of agglomerates of surfactant molecules in a liquid and promote washing by storing hydrophobic substances (fats, oils, etc.) in the agglomerates. The CMC value is defined as the concentration of surfactant above which micelles begin to form and the surface tension of the formulation remains relatively constant. The CMC value represents the amount of surfactant required to achieve the maximum surface tension reduction. The lower the CMC value, the less surfactant is required to effectively emulsify, dissolve, and disperse the hydrophobic substances in the formulation. Among the classes of surfactants (nonionic, anionic, cationic, and amphoteric surfactants), the lowest CMC is usually found in the nonionic class. In general, nonionic surfactants with very low CMC values ​​can provide excellent wetting and detergency benefits. Therefore, the CMC value measures the efficiency of the surfactant, and surfactants with lower CMC values ​​will show the desired benefits when used in consumer products, industrial processes, and biological applications.

[0101] These CMC values ​​of surfactant solutions can be determined by measuring the surface tension at different concentrations. CMC values ​​can be calculated by different known techniques (e.g., tensiometric measurements, conductivity measurements, fluorescence spectroscopy). In some embodiments, the combination of the PEFA surfactant described herein with another surfactant (surfactant combination) may have a CMC value of about 0.1 mM or less; in some embodiments, the CMC value is about 0.07 mM or less; in some embodiments, the CMC value is about 0.05 mM or less; in some embodiments, the CMC value is about 0.04 mM or less; in some embodiments, the CMC value is about 0.03 mM or less. In some embodiments, such surfactant combinations may have a CMC value of about 0.01 mM to about 0.1 mM; and in some embodiments, the CMC value is about 0.01 mM to about 0.05 mM. In certain surfactant combinations, the presence of the PEFA compound described herein and the second surfactant can significantly reduce the amount of the second surfactant (e.g., sodium dodecyl sulfate, SDS) required to achieve the desired surface tension. For example, by adding PEFA surfactants as described herein, the amount of SDS and / or sodium dodecylbenzene sulfonate (SDBS) required to achieve a desired surface tension of a formulation can be reduced by more than 10 times, more than 50 times, or more than 100 times, making the surfactant mixture more beneficial and effective.

[0102] The surfactant may contain one or more PEFA compounds. In some embodiments, the surfactant may have pentitol polyol esters of fatty acids and hexitol polyol esters of fatty acids. In some embodiments, the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters may account for about 20% to about 99% of the PEFA; and in some embodiments, about 30% to about 95% of the PEFA; and in some embodiments, about 40% to about 90% of the PEFA. In some embodiments, the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters may account for about 50% or more of the PEFA; in some embodiments, about 60% or more of the PEFA; and in some embodiments, about 70% or more of the PEFA; and in some embodiments, about 80% or more of the PEFA. In some embodiments, the ratio of pentitol polyol esters to hexitol polyol esters in the surfactant is about 5:1 or greater; in some embodiments, the ratio is about 8:1 or greater; in some embodiments, the ratio is about 10:1 or greater; in some embodiments, the ratio is about 15:1 or greater; in some embodiments, the ratio is about 20:1 or greater; in some embodiments, the ratio is about 30:1 or greater; in some embodiments, the ratio is about 40:1 or greater; in some embodiments, the ratio is about 50:1 or greater.

[0103] Surfactants as described herein can have a wide range of applications. For example, such surfactants can be included in personal care compositions. Some examples of such personal care compositions include skin moisturizers, perfumes, lipsticks, nail polishes, eye and facial makeup preparations, shampoos, perms, hair dyes, toothpastes, and deodorants. Surfactants can be used in cleaning compositions. Some examples of such cleaning compositions include hard surface cleaners, all-purpose cleaners, bleaches, detergents, and disinfectants. Surfactants as described herein will be applicable to any personal care composition or cleaning composition requiring an effective surfactant.

[0104] Example

[0105] For surfactant mixtures at different ratios, the CMC values ​​of water-soluble surfactants were measured. The CMC values ​​were calculated using known techniques using a plot of surface tension versus the logarithm of different surfactant concentrations. The measured CMC values ​​for a combination of PEFA and sodium dodecyl sulfate (SDS) at a ratio of 60:40 (weight:weight), other nonionic surfactants and PEFA at the same ratios are shown in Table 1. Figure 1 and Figure 2 Representative CMC measurements obtained for surfactants containing SDS and PEFA in the indicated weight ratios are shown. Figure 2As shown, the surfactant combination of SDS and PEFA at a ratio of 60:40 has the lowest CMC value (0.031 mM) compared to all other reference non-ionic surfactants. Table 1 discloses that the CMC values ​​of pure SDS and pure SDBS are 8.2 mM and 2.5 mM, respectively. In addition, unlike cetearyl glucoside, PEFA is soluble in SDBS at 60:40. Table 1 also discloses that a mixture of SDBS and PEFA at a ratio of 60:40 was measured and its CMC value was 0.22 mM, which is an order of magnitude lower than all other reference surfactants. Since cetearyl glucoside is insoluble in SDBS, the CMC value of the surfactant combination of SDBS and cetearyl glucoside at 80:20 could not be measured. Therefore, since the combination of ionic surfactants such as SDS and SDBS with PEFA has a low CMC value, the combination of PEFA compounds with other ionic surfactants has a high efficiency.

[0106] Table 1

[0107]

[0108] Those skilled in the art will recognize or be able to ascertain using no more than routine experimentation many equivalents to the specific embodiments of the invention described herein.It is not intended that the scope of the invention be limited to the above description, but rather is set forth in the claims that follow.

[0109] In the claims, articles such as "a", "an", and "the" may mean one or more than one, unless stated to the contrary or obvious from the context. Claims or descriptions including "or" between one or more members of the group are considered satisfied if one, more than one, or all of the group members are present in, used in, or otherwise relevant to a given product or method, unless stated to the contrary or obvious from the context. The invention includes embodiments in which exactly one member of the group is present in, used in, or otherwise relevant to a given product or method. The invention includes embodiments in which more than one or all of the group members are present in, used in, or otherwise relevant to a given product or method.

[0110] It should also be noted that the term "comprising" is intended to be open ended, and allows but does not require the inclusion of additional elements or steps. When the term "comprising" is used herein, the term "consisting of" is also encompassed and disclosed.

[0111] When a range is given, the endpoints are included. In addition, it should be understood that unless otherwise stated or obvious from the context and the understanding of a person of ordinary skill in the art, the values ​​expressed as ranges may present any specific value or sub-range within the range in different embodiments of the present invention, to one-tenth of the unit of the lower limit of the range, unless the context clearly dictates otherwise.

[0112] All cited sources, such as references, publications, databases, database entries, and techniques cited herein, are incorporated by reference into this application, even if not explicitly stated in the citation. In the event of a conflict between a cited source and the statements of this application, the statements in this application shall prevail.

[0113] Section and table headings are not limiting.

[0114] 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 aspects.

[0115] While the invention has been described at some length and with a certain particularity with respect to several described embodiments, it is not intended that the invention be limited to any such details or embodiments or to any particular embodiment, but rather the invention should be construed with reference to the appended claims so as to provide the broadest possible interpretation of such claims in light of the prior art and thereby effectively encompass the intended scope of the invention.

[0116] All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In the event of a conflict, the present specification (including definitions) shall prevail. In addition, section headings, materials, methods, and examples are illustrative only and not restrictive.

Claims

1. A PEFA compound represented by formula (I) or (II): or its salts or acids, in R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); Each R x are independently C1-C3 alkyl, wherein R x Optionally substituted with 1-7 halogens; Each R y are independently -H or C1-C3 alkyl, wherein R x Optionally substituted with 1-7 halogens; 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, in When n is 12 or 14 and R 1 When it is -OH or -(O)Ac, then R a is not -(O)Ac or -(O)Me; When n is 12 and R a When it is -OH, then R 2 is not -OH; or When n is 12 or 14, R a Yes -OH, R 2 Yes OH, R 3 is OH, and R 4 When it is OH, then R 1 Yes(O)R x or -(O)(C2H5O) p R y ; When n is 12 or 14, R 1 is -(O)S(O2)OH, R 2 is -(O)S(O2)OH, R 3 is -(O)S(O2)OH, R 4 is -(O)S(O2)OH, and R 5 When it is -(O)S(O2)OH, then R a Yes-(O)C(O)R x , R x 、-(O)C(O)OR x 、-(O)C(O)N(H)R x 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 or -(O)S(O2)OH.

2. The PEFA compound according to claim 1, wherein R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m ); Each R x are independently C1-C3 alkyl, wherein R x Optionally substituted with 1-7 halogens; Each R y are independently -H or C1-C3 alkyl, wherein R x Optionally substituted with 1-7 halogens; 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.

3. The PEFA compound of claim 1, wherein n is 4-20.

4. The PEFA compound according to any one of claims 1 to 2, wherein R 1 It is -(O)P(O)(OH)2.

5. The PEFA compound according to any one of claims 1 to 2, wherein R 1 It is -(O)Ac.

6. The PEFA compound according to any one of claims 1 to 2, wherein R 1 It is -(O)S(O2)OH.

7. The PEFA compound according to any one of claims 1 to 2, wherein R 1 It is -OH.

8. The PEFA compound according to any one of claims 1 to 7, wherein R a It is -OH.

9. The PEFA compound according to any one of claims 1 to 7, wherein R a It’s-(O)Me.

10. The PEFA compound according to any one of claims 1 to 7, wherein R a It is -(O)Ac.

11. The PEFA compound of any one of claims 1-10, wherein n is 7-9.

12. The PEFA compound of any one of claims 1-10, wherein n is 8.

13. The PEFA compound of any one of claims 4 to 10, wherein the compound is further represented by formula (Ia) or (II-a): or its salts or acids, in n is 6-12.

14. The PEFA compound of claim 13, wherein n is 7-9.

15. The PEFA compound of claim 13, wherein n is 8.

16. The PEFA compound of claim 13, wherein n is 6.

17. A PEFA compound selected from the group consisting of: or its salts or acids.

18. A surfactant formed from one or more PEFA compounds as claimed in any one of claims 1 to 17, wherein the surfactant has a CMC value of about 0.09 mM or less.

19. The surfactant of claim 18, having a CMC value of about 0.05 mM or less.

20. The surfactant of claim 18, having a CMC value of about 0.03 mM or less.

21. The surfactant of claim 18, having a CMC value of about 0.01 mM to about 0.09 mM.

22. The surfactant of claim 18 having a CMC value of about 0.01 mM to about 0.5 mM.

23. The surfactant of claim 18, wherein the one or more PEFA compounds comprise pentitol polyol esters, hexitol polyol esters, or a combination thereof.

24. The surfactant of claim 23, wherein the ratio of pentitol polyol ester to hexitol polyol ester is about 5:1 or greater.

25. The surfactant of claim 23, wherein the ratio of pentitol polyol ester to hexitol polyol ester is about 20:1 or greater.

26. The surfactant of claim 23, wherein the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can comprise from about 20% to about 99% of the PEFA.

27. The surfactant of claim 23, wherein the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can comprise from about 30% to about 95% of the PEFA.

28. The surfactant of claim 23, wherein the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can comprise about 40% or more of the PEFA.

29. A surfactant composition comprising a surfactant as claimed in claims 18 to 28 and one or more surfactants formed from non-PEFA compounds.

30. A personal care composition comprising the surfactant of claims 18-28.

31. A cleaning composition comprising the surfactant of claims 18-22.

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