Surfactant having PEFA compound and method of using same

Abstract

Disclosed herein are polyol esters of fatty acids (PEFAs), as well as their use as surfactants, methods for their preparation, and compositions thereof.

Description

[Technical field]

[0001] REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 63 / 365,404, entitled "Compounds, Compositions, and Methods of Use Thereof," filed May 26, 2022; U.S. Provisional Patent Application No. 63 / 365,405, entitled "Polyol Ester of Fatty Acids (PEFAs) as Antifoam," filed May 26, 2022; and U.S. Provisional Patent Application No. 63 / 365,406, entitled "Polyol Ester of Fatty Acids (PEFAs) as Emulsifiers," filed May 26, 2022, which provisional applications are incorporated herein by reference in their entireties.

[0002] The present disclosure relates to polyol esters of fatty acids (PEFAs), and their use as surfactants, methods for their preparation, and compositions thereof. [Background technology]

[0003] PEFA compounds can have a variety of uses, including as surfactants.Surfactants (both petroleum-based and bio-based) are examples of compounds that can act as emulsifiers, detergents, dispersants, general foam control agents, and wetting agents, which are used in a wide variety of consumer applications, including agricultural, nutritional, cosmetic, veterinary, treatment, coating, ink, and industrial applications.However, such surfactants may show poor performance in terms of sustainability, bioaccumulation, ecotoxicity, and / or biodegradability.

[0004] Therefore, there is a need for the development of alternative surfactants and compositions that can improve the formulation of consumer products in these applications. [Brief description of the drawings]

[0005] [Figure 1] 1 is a chart showing the critical micelle concentration versus surface tension of sodium dodecyl sulfate as a surfactant. [Diagram 2] 1 is a chart showing critical micelle concentration versus surface tension for a combination of sodium dodecyl sulfate and PEFA in a 60:40 ratio as surfactants. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] Polyol esters of fatty acids are amphipathic molecules that include a sugar alcohol (e.g., D-mannitol and / or D-arabitol) ester-linked to the carboxyl terminus of a 3-hydroxy fatty acyl moiety, which may or may not be acetylated. The unesterified hydroxyl group of the sugar alcohol may also be acetylated or unacetylated. In some embodiments, the one or more polyol lipids produced are a mixture of similar compounds that include an (R)-3-hydroxy fatty acyl moiety with chain lengths that vary from about 8 to 24 carbons, preferably from 12 to 20 carbons. In some embodiments, the (R)-3-hydroxy fatty acyl moiety can exhibit a degree of unsaturation that varies from about 0 to 6, e.g., from 2 to 5. In some embodiments, the unesterified hydroxyl group of the sugar alcohol can be esterified to an acetyl group. In some embodiments, the sugar alcohol can be fully acetylated. In some embodiments, the sugar alcohol can be unacetylated. In some embodiments, the acetylation can vary between these two states.

[0007] The present disclosure relates, inter alia, to [ka] or a salt or acid thereof, In the formula, R 1 , R 2 , R 3 , R 4 , R5 , R a , and a are defined herein.

[0008] definition In this disclosure, the following terms have the following meanings.

[0009] The term "about" preceding a number encompasses up to ±10% of the value of that number. It is to be understood that the value to which the term "about" refers is itself specifically and preferably disclosed.

[0010] The term "alkyl" means a straight or branched chain alkyl group. Representative alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.

[0011] The term "halogen" means F, Cl, Br, or I.

[0012] As used herein, the term "surfactant combination" refers to a surfactant that includes a PEFA and at least one other surfactant, i.e., a surfactant mixture that includes one or more surfactants formed from PEFA compounds and one or more surfactants formed from non-PEFA compounds.

[0013] 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 human and lower animal tissues without excessive toxicity, irritation, allergic response, etc., and are commensurate with a reasonable benefit / risk ratio. Salts can include pharmaceutically or biologically acceptable salts. Similarly, 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, which is incorporated herein by reference. Pharmaceutically or biologically acceptable salts of the compounds of the present disclosure can include those derived from suitable inorganic and organic acids and bases, while pharmaceutically or biologically acceptable acids of the compounds of the present disclosure can include suitable inorganic and organic acids. Examples of pharmaceutically or biologically acceptable inorganic acids include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, and perchloric acid, while organic acids include, for example, acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid, propionic acid, or malonic acid, or by other methods used in the art, such as ion exchange.An example of pharmaceutically or biologically acceptable acid addition salt is the salt of amino group formed with such example inorganic acid.Another example of pharmaceutically or biologically acceptable acid is carboxylic acid, where the carboxylate form of PEFA compound contains carboxyl group.Other pharma- ceutically 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, hemisulfate, heptanoate, hexanoate, hydroiodide, 2-hydroxy-ethanoate, and the like. Examples of the salts include phenylsulfonate, 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, and valerate.

[0014] Salts derived from appropriate bases include alkali metal salts, alkaline earth metal salts, ammonium salts, and N(C 1-4 Alkyl) 4 Exemplary alkali or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium salts, etc. Further pharma- ceutically or biologically acceptable salts include, where appropriate, ammonium, quaternary ammonium, and amine cations formed with counterions such as halides, hydroxides, carboxylates, sulfates, phosphates, nitrates, lower alkyl sulfonates, and aryl sulfonates.

[0015] The present disclosure includes both the (R) and (S) configurations at each stereocenter, whether depicted as defined or not. Additionally, 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.

[0016] PEFA Compounds Disclosed herein are compounds formed from one or more polyol esters of fatty acids that can provide increased benefits to personal care and other consumer products.

[0017] Polyol esters of fatty acids are amphipathic molecules that include a sugar alcohol (e.g., D-mannitol and / or D-arabitol) ester-linked to the carboxyl terminus of a 3-hydroxy fatty acyl moiety, which may or may not be acetylated. The unesterified hydroxyl group of the sugar alcohol may also be acetylated or unacetylated. In some embodiments, the one or more polyol lipids produced are a mixture of similar compounds that include an (R)-3-hydroxy fatty acyl moiety with chain lengths that vary from about 8 to 24 carbons, preferably from 12 to 20 carbons. In some embodiments, the (R)-3-hydroxy fatty acyl moiety can exhibit a degree of unsaturation that varies from about 0 to 6, e.g., from 2 to 5. In some embodiments, the unesterified hydroxyl group of the sugar alcohol can be esterified to an acetyl group. In some embodiments, the sugar alcohol can be fully acetylated. In some embodiments, the sugar alcohol can be unacetylated. In some embodiments, the acetylation can vary between these two states.

[0018] In some embodiments, the polyol lipid disclosed herein is an acetylated C12:0-3-hydroxy fatty acid with acetylation sites ester-linked to three D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid with acetylation sites ester-linked to four D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to two D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to two D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid with acetylation sites ester-linked to four D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid with acetylation sites ester-linked to five D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to three D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to three D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to four D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid with acetylation sites ester-linked to two D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid with acetylation sites ester-linked to five D-mannitols.In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to four D-mannitols. In some embodiments, the polyol lipid is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to two D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to five D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to four D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to three D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to four D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to three D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to five D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to four D-arabitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C20:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to three D-mannitols. In some embodiments, the polyol lipid disclosed herein is an acetylated C20:0-3-hydroxy fatty acid in which the acetylation site is ester-linked to four D-mannitols.

[0019] In some exemplary embodiments, the PEFA compound is [ka] or a salt or acid thereof, During the ceremony, R 1 -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 ) selected from the group consisting of R 2 -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 ) selected from the group consisting of R 3 is -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 ) selected from the group consisting of R 4is -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 selected from the group consisting of R 5 is -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 H5 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 ) selected from the group consisting of R a -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 ) selected from the group consisting of Each R x is independently C 1 -C 3 alkyl, where R x is optionally substituted with 1 to 7 halogens; Each R y are independently -H, C 1 -C 3 alkyl, where R xis optionally substituted with 1 to 7 halogens; n is 2 to 20; j is 2 to 12, k is 4 to 26; m is 1 to 16, and each p is independently selected from 1 to 10; Where: n is 12 or 14, and R 1 When is -OH or -(O)Ac, R a is not -(O)Ac or -(O)Me, n is 12 and R a is -OH, R 2 is not -OH, or n is 12 or 14, and R a is -OH and R 2 is -OH and R 3 is -OH and R 4 is -OH, R 1 (O)R x or -(O)(C 2 H 5 O) p R y and n is 12 or 14, and R 1 -(O)S(O 2 )OH and R 2 -(O)S(O 2 )OH and R 3 -(O)S(O 2 )OH and R 4 -(O)S(O 2 )OH and R 5 -(O)S(O 2 )OH, then R a HA-(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(O2 )OH.

[0020] In some embodiments relating to formula (I) or (II), R 1 -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 ) selected from the group consisting of R 2 -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 ) and is selected from the group consisting of R 3 is -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 ) and is selected from the group consisting of R 4 is -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 ) and is selected from the group consisting of R 5 is -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 ) selected from the group consisting of R a -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 ) selected from the group consisting of Each R x is independently C 1 -C 3 alkyl, where R x is optionally substituted with 1 to 7 halogens; Each R y are independently -H, C 1 -C 3 alkyl, where R x is optionally substituted with 1 to 7 halogens; n is 2 to 11; j is 2 to 12, k is 4 to 26; m is 1 to 16, and Each p is independently selected from 1 to 10.

[0021] In some embodiments, the PEFA compound has formula (Ia) or (II-a): [ka] or a salt or acid thereof, During the ceremony, n is 6 to 12.

[0022] In some embodiments, R 1 -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 is -C(O)R x , -Rx , -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 In some embodiments, R 1 is -H. In some embodiments, R 1 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 1 is -C(O)R x In some embodiments, R 1 In some embodiments, R 1 -R x In some embodiments, R 1 is -C(O)OR y In some embodiments, R 1 is -C(O)N(H)R y In some embodiments, R 1 is -(C 2 H 5 O) p R y In some embodiments, R 1 is -P(O)(OH) 2 In some embodiments, R 1 is -S(O 2 )OH. In some embodiments, R 1 is -(C j H k O m ).

[0023] In some embodiments, R 2 -H, -C(O)R x , -R x , -C(O)OR y , -C(O)N(H)R y , -(C 2 H 5 O) p Ry , -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 is -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 In some embodiments, R 2 is -H. In some embodiments, R 2 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 2 is -C(O)R x In some embodiments, R 2 In some embodiments, R 2 -R x In some embodiments, R 2 is -C(O)OR y In some embodiments, R 2is -C(O)N(H)R y In some embodiments, R 2 is -(C 2 H 5 O) p R y In some embodiments, R 2 is -P(O)(OH) 2 In some embodiments, R 2 is -S(O 2 )OH. In some embodiments, R 2 is -(C j H k O m In some embodiments, R 3 -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 3 is -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 In some embodiments, R 3 is -H. In some embodiments, R 3 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 3 is -C(O)R x In some embodiments, R 3 In some embodiments, R 3 -R x In some embodiments, R 3 is -C(O)OR y In some embodiments, R 3 is -C(O)N(H)R y In some embodiments, R 3 is -(C 2 H 5 O) p R y In some embodiments, R 3 is -P(O)(OH) 2 In some embodiments, R 3 is -S(O 2 )OH. In some embodiments, R 3 is -(C j H k O m In some embodiments, R 4 -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 4 is -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 In some embodiments, R 4 is -H. In some embodiments, R 4 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 4 is -C(O)R x In some embodiments, R 4 In some embodiments, R 4 -R x In some embodiments, R 4 is -C(O)OR y In some embodiments, R 4 is -C(O)N(H)R y In some embodiments, R 4 is -(C 2 H5 O) p R y In some embodiments, R 4 is -P(O)(OH) 2 In some embodiments, R 4 is -S(O 2 )OH. In some embodiments, R 4 is -(C j H k O m In some embodiments, R 5 -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 is -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 In some embodiments, R 5 is -H. In some embodiments, R 1 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R 5 is -C(O)R x In some embodiments, R 5 In some embodiments, R 5 -R x In some embodiments, R 5 is -C(O)OR y In some embodiments, R 5 is -C(O)N(H)R y In some embodiments, R 5 is -(C 2 H 5 O) p R y In some embodiments, R 5 is -P(O)(OH) 2 In some embodiments, R 5 is -S(O 2 )OH. In some embodiments, R 5 is -(C j H k O m In some embodiments, R a -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)Rx , -(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 is -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 In some embodiments, R a is -H. In some embodiments, R 1 is -P(O)(OH) 2 or -S(O 2 )OH. In some embodiments, R a is -C(O)R x In some embodiments, R a In some embodiments, R a -R x In some embodiments, R a is -C(O)OR y In some embodiments, R a is -C(O)N(H)R y In some embodiments, R a is -(C 2 H 5 O) p R y In some embodiments, R ais -P(O)(OH) 2 In some embodiments, R a is -S(O 2 )OH. In some embodiments, R a is -(C j H k O m ).

[0024] In some embodiments, each R x is independently C 1 -C 3 alkyl, where R x may be substituted with 1 to 7 halogens. In some embodiments, R x is methyl, where R x may be substituted with 1 to 7 halogens. In some embodiments, R x is ethyl, where R x may be substituted with 1 to 7 halogens. In some embodiments, R x is n-propyl, where R x may be substituted with 1 to 7 halogens. In some embodiments, R x is i-propyl, where R x may be substituted with 1 to 7 halogens. In some embodiments, R x is methyl. In some embodiments, R x is ethyl. In some embodiments, R x is n-propyl. In some embodiments, R x is i-propyl.

[0025] In some embodiments, each R y are independently -H or C 1 -C 3 alkyl, where R y may be substituted with 1 to 7 halogens. In some embodiments, R y is -H. In some embodiments, each R y is independently C 1 -C 3 alkyl, where Ry may be substituted with 1 to 7 halogens. In some embodiments, R y is methyl, where R y may be substituted with 1 to 7 halogens. In some embodiments, R y is ethyl, where R y may be substituted with 1 to 7 halogens. In some embodiments, R y is n-propyl, where R y may be substituted with 1 to 7 halogens. In some embodiments, R y is i-propyl, where R y may be substituted with 1 to 7 halogens. In some embodiments, R y is methyl. In some embodiments, R y is ethyl. In some embodiments, R y is n-propyl. In some embodiments, R y is i-propyl.

[0026] The present disclosure relates to [ka] or a salt or acid thereof.

[0027] Below are examples of specific embodiments of the invention described by this disclosure. The examples are presented for illustrative purposes only and are not intended to limit the scope of the invention in any way. Groups referred to in the following examples, such as OR 1 , OR 2 etc. are interchangeable with the corresponding groups described herein, e.g., R 1 , R 2 etc., which may be replaced by any of the groups shown in each 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.

[0028] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 1 or 2: [ka] In the formula, LG is a leaving group. [ka] In the formula, LG is a leaving group.

[0029] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 3 or 4: [ka]

[0030] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 5 or 6: [ka]

[0031] Synthesis / isolation of 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-hydroxydodecanoic acid 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl ester is shown below.

[0032] Synthesis of 3-hydroxydodecanoic acid 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl ester [ka]

[0033] D-Mannitol and P 2 O 5is heated directly at 100°C for 6 hours. As an 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 heated in p-toluenesulfonic acid at 170°C for 4 hours with N as outlined in Wenyuan Han et al. Polymers 11,(2019),1031. 2 Heat underneath.

[0034] Surfactants Surfactants are surface-active compounds. They generally 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, and is therefore also called the hydrophilic part. On the other hand, the non-polar part can form interactions with non-polar solvents such as oil, and is therefore also called the lipophilic or hydrophobic part. There are four basic classes of surfactants: anionic surfactants, cationic surfactants, zwitterionic surfactants, and non-ionic surfactants.

[0035] Surfactants are amphiphilic molecules that are widely used in consumer products, industrial processes, and biological applications. An important 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 inside a liquid, which facilitate cleaning by storing hydrophobic substances (fats, oils, etc.) within the agglomerates. The CMC value is defined as the concentration above which micelles begin to form and the surface tension of the formulation remains relatively constant. The CMC value indicates the amount of surfactant required to reach the maximum surface tension reduction. The lower the CMC value, the less surfactant is required to effectively emulsify, solubilize, and disperse hydrophobic substances in the formulation. Among the surfactant classes - nonionic, anionic, cationic, and amphoteric - the lowest CMC is generally found in the nonionic category. Nonionic surfactants with very small CMC values ​​can usually provide excellent wetting and cleaning effects. Thus, the CMC value measures the efficiency of a surfactant, with surfactants with lower values ​​exhibiting desirable effects when used in consumer products, industrial processes, and biological applications.

[0036] These CMC values ​​can be determined for surfactant solutions by measuring the surface tension at various concentrations. CMC values ​​can be calculated from various known techniques (e.g., tensiometer, conductivity, fluorescence spectroscopy). In some embodiments, the PEFA surfactants described herein in combination with another surfactant (surfactant combinations) can have a CMC value of about 0.1 mM or less, in some embodiments, a CMC value of about 0.07 mM or less, in some embodiments, a CMC value of about 0.05 mM or less, in some embodiments, a CMC value of about 0.04 mM or less, in some embodiments, a CMC value of about 0.03 mM or less. In some embodiments, such surfactant combinations can have a CMC value of about 0.01 mM to about 0.1 mM, and in some embodiments, a CMC value of about 0.01 to about 0.05 mM. For certain surfactant combinations, the presence of a PEFA compound described herein and a second surfactant can significantly reduce the amount of the second surfactant (e.g., sodium dodecyl sulfate, SDS) required to achieve a desired surface tension. For example, the amount of SDS and / or sodium dodecylbenzene sulfonate (SDBS) required to achieve a desired surface tension in a formulation can be reduced by more than 10-fold, more than 50-fold, or even more than 100-fold with the addition of the PEFA surfactants described herein, making the surfactant mixture more beneficial and effective.

[0037] The surfactant can contain one or more PEFA compounds. In some embodiments, the surfactant can 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 can comprise about 20% to about 99% PEFA, and in some embodiments, about 30% to about 95% PEFA, and in some embodiments, about 40% to about 90% PEFA. In some embodiments, the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can comprise about 50% or more PEFA, in some embodiments, about 60% or more PEFA, and in some embodiments, about 70% or more PEFA, and in some embodiments, about 80% or more 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, and in some embodiments, the ratio is about 50:1 or greater.

[0038] The surfactants described herein may 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, fragrances, lipsticks, finger nail polish, eye and face cosmetic preparations, shampoos, perms, hair coloring, dentifrices, and deodorants. The surfactants can be used in cleaning compositions. Some examples of such cleaning compositions include hard surface cleaners, multi-purpose cleaners, bleaching agents, cleaning agents, and disinfectants. The surfactants described herein are suitable for any personal care or cleaning composition where an effective surfactant is needed. EXAMPLES

[0039] The CMC values ​​of water-soluble surfactants were measured at various ratios for the surfactant mixture. The CMC values ​​were calculated using known techniques utilizing plots of surface tension versus the logarithm of various surfactant concentrations. The measured CMC values ​​of PEFA combined with sodium dodecyl sulfate (SDS) in a 60:40 (weight:weight) ratio, as well as the CMC values ​​of other non-ionic surfactants and PEFA in the same ratios, are shown in Table 1. Figures 1 and 2 show the corresponding CMC measurements obtained from surfactants containing SDS and PEFA in the weight ratios shown. As shown in Figure 2, the surfactant combination of SDS and PEFA in a 60:40 ratio has the lowest CMC value (0.031 mM) compared to all other reference non-ionic surfactants. Table 1 discloses that the CMC values ​​of neat SDS and neat SDBS are 8.2 mM and 2.5 mM, respectively. In addition, PEFA is soluble in SDBS at 60:40, unlike cetearyl glucoside. Table 1 also discloses that a mixture of SDBS and PEFA in a 60:40 ratio was measured to have a CMC value of 0.22 mM, an order of magnitude lower than all other reference surfactants. The CMC value of an 80:20 surfactant combination of SDBS and C glucoside was not measurable because C glucoside is insoluble in SDBS. Thus, PEFA compounds in combination with other ionic surfactants have high efficiency due to the low CMC values ​​of PEFA in combination with ionic surfactants such as SDS and SDBS. [Table 1]

[0040] 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 invention is not intended to be limited to the above Description, but rather is as set forth in the appended claims.

[0041] In the claims, articles such as "a," "an," and "the" may mean one or more, unless specifically indicated to the contrary or otherwise clear from the context. A claim or description containing "or" between one or more elements of a group is considered to be satisfied if one, more than one, or all of the group elements are present in, employed in, or otherwise relevant to a given product or process, unless the contrary is indicated or otherwise clear from the context. The invention includes embodiments in which only one element of a group is present in, employed in, or otherwise relevant to a given product or process. The invention includes embodiments in which two or more, or all of the group elements are present in, employed in, or otherwise relevant to a given product or process.

[0042] It should also be noted that the term "comprising" is intended to be open-ended, permitting, but not necessarily, the inclusion of additional elements or steps. When the term "comprising" is used herein, the term "consisting of" is therefore included and disclosed.

[0043] Where ranges are given, endpoints are included. Furthermore, unless otherwise indicated or otherwise apparent from the context and the understanding of one of ordinary skill in the art, it should be understood that values ​​expressed as ranges can take any specific value or subrange within the ranges defined 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.

[0044] All sources, e.g., references, publications, databases, and database entries cited herein, are incorporated by reference into this application, even if not explicitly stated in the citation. In the event of a conflict between the statements in the sources and this application, the statements in this application will control.

[0045] Section and table headings are not intended to be limiting.

[0046] The words which have been used are words of description rather than of limitation, and it is to be understood 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.

[0047] While the invention has been described at some length and with some specificity with respect to certain embodiments set forth, it is not intended that the invention be limited to any such specifics or embodiments or to any particular embodiment. The invention should be construed with reference to the appended claims as being interpreted in the broadest possible manner in light of the prior art and to encompass the intended scope of the invention.

[0048] 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, the section headings, materials, methods, and examples are illustrative only and not intended to be limiting.

Claims

1. PEFA compounds represented by formula (I) or (II), 【Chemistry 1】 or its salt or acid, During the ceremony, R １ 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, -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 ), and is selected from the group consisting of R ２ 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 ), and is selected from the group consisting of R ３ is -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 ), and is selected from the group consisting of R ４ 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 ), and is selected from the group consisting of R ５ is -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 ), and is selected from the group consisting of R ａ is -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 ), and is selected from the group consisting of Each R ｘ C is independent １ -C ３ It is an alkyl group, and in the formula, R ｘ These may be replaced by 1 to 7 halogens. Each R ｙ Independently, -H or C １ -C ３ It is an alkyl group, and in the formula, R ｘ These may be replaced by 1 to 7 halogens. n is between 2 and 20. j is between 2 and 12. k is between 4 and 26. m is between 1 and 16, and Each p is independently selected from 1 to 10. however, n is 12 or 14, and R １ If R is -OH or -(O)Ac, ａ is not -(O)Ac or -(O)Me, n is 12 and R ａ If R is -OH, ２ Is it not -OH, or n is 12 or 14, R ａ is -OH, and R ２ OH is R ３ is OH and R ４ If R is OH, １ (O)R ｘ or -(O)(C ２ H ５ O) ｐ R ｙ And, n is 12 or 14, R １ ga-(O)S(O ２ )OH, R ２ ga-(O)S(O ２ )OH, R ３ ga-(O)S(O ２ )OH, R ４ ga-(O)S(O ２ ) OH and R ５ ga-(O)S(O ２ ) If it is OH, ａ ha-(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 PEFA compounds, or their salts or acids.

2. R １ is -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 selected from the group consisting of R ２ is -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 ), and is selected from the group consisting of R ３ is -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 selected from the group consisting of R ４ is -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 ) and is selected from the group consisting of R ５ is -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 ), and is selected from the group consisting of R ａ is -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 ), and is selected from the group consisting of Each R ｘ C is independent １ -C ３ It is an alkyl group, and in the formula, R ｘ These may be replaced by 1 to 7 halogens. Each R ｙ Independently, -H or C １ -C ３ It is an alkyl group, and in the formula, R ｘ These may be replaced by 1 to 7 halogens. n is between 4 and 12. j is between 2 and 12. k is between 4 and 26. m is between 1 and 16, and The PEFA compound according to claim 1, wherein each p is independently selected from 1 to 10.

3. The PEFA compound according to claim 1, wherein n is 4 to 20.

4. R １ is -(O)P(O)(OH) ２ The PEFA compound according to claim 1.

5. R １ The PEFA compound according to claim 1, wherein is -(O)Ac.

6. R １ is -(O)S(O ２ The PEFA compound according to claim 1, wherein it is an OH group.

7. R １ The PEFA compound according to claim 1, wherein is -OH.

8. R ａ The PEFA compound according to claim 1, wherein is -OH.

9. R ａ The PEFA compound according to claim 1, wherein is -(O)Me.

10. R ａ The PEFA compound according to claim 1, wherein is -(O)Ac.

11. The PEFA compound according to claim 1, wherein n is 7 to 9.

12. A surfactant formed from one or more PEFA compounds as described in claim 1, wherein the surfactant has a CMC value of about 0.09 mM or less.

13. The surfactant according to claim 12, wherein the one or more PEFA compounds include pentitol polyol ester, hexitol polyol ester, or a combination thereof.

14. The surfactant according to claim 13, wherein the ratio of pentitol polyol ester to hexitol polyol ester is about 5:1 or more.

15. The surfactant according to claim 13, wherein the ratio of pentitol polyol ester to hexitol polyol ester is about 20:1 or more.

16. The surfactant according to claim 13, wherein the C16 and C18 fatty acid components of the pentitol polyol ester and the hexitol polyol ester can account for about 20% to about 99% of the PEFA.

17. A surfactant composition comprising the surfactant described in claim 12 and one or more surfactants formed from non-PEFA compounds.

18. A personal care composition or cleaning composition comprising the surfactant described in claim 12. 【Request Item 19】 【Chemistry 2】 A PEFA compound selected from the group consisting of the following, or a salt or acid thereof.

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