Emulsifiers formed from polyol esters of fatty acids

Abstract

An emulsifier, a water-in-oil (W / O) emulsion composition, and an oil-in-water (O / W) emulsion composition, each comprising a polyol lipid having a polyol ester of fatty acids (PEFA) compound.

Description

[Technical field]

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

[0002] The present disclosure relates to emulsifiers and water-in-oil and oil-in-water emulsion compositions having polyol lipids formed from polyol ester fatty acid (PEFA) compounds. [Background technology]

[0003] Emulsifiers for water-in-oil emulsions show better humidity resistance than oil-in-water emulsions. However, stabilizing water-in-oil emulsions is more difficult than stabilizing oil-in-water emulsions. In addition, water-in-oil emulsions often have problems with emulsification / dispersion properties (e.g., difficulty in stabilizing emulsions while maintaining low emulsion viscosity, and difficulty in maintaining stability in areas with large temperature changes), and such water-in-oil emulsions are difficult to produce soft touch, light smoothness, and good spreadability and good moisture retention. These problems of water-in-oil emulsions are challenges when formulating cosmetic compositions.

[0004] In food processing, a mixture of food ingredients is typically subjected to extensive thermal and mechanical treatments such as baking, boiling, steaming, freezing, kneading, mixing, and extruding to form a food product with the desired taste, texture, and visual characteristics such as color and shape. Food ingredients may not be compatible with other food ingredients when present in a mixture. For example, oil and water are immiscible and form thermodynamically unstable emulsions when mixed together. The oil and water phases gradually separate and the emulsion coalesces, coalesces, creams, or breaks down. This can adversely affect food properties such as shelf life, taste, or aesthetics.

[0005] One example of an emulsifier used in beverages is gum acacia, which is prepared from the exudate from the stems and branches of the sub-Saharan species of acacia tree, Acacia sengal and Acacia seyal. Gum arabic can be difficult and expensive to obtain due to its high demand and erratic supply.

[0006] Therefore, there is a need to develop alternative renewable or biodegradable emulsifiers, water-in-oil (W / O) emulsion compositions, and oil-in-water (O / W) emulsion compositions that have long-term emulsion stability when exposed to heat or that can improve the formulation of end-consumer products. [Brief description of the drawings]

[0007] [Figure 1] Photographs showing a first vial on the left with ZnO particles added to an emulsifier according to one embodiment, and a second vial on the right with ZnO particles added to a conventional emulsifier, both being stirred. [Diagram 2] The photographs show the vials of FIG. 1, all of which were stored at 60° C. for one week after stirring. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The details of different embodiments of the invention are set forth in the description below. Other features, objects, and advantages of the invention will become apparent from the description and drawings, and from the claims.

[0009] definition As used herein, "food" refers to an edible or drinkable material, or a material that can be processed into an edible or drinkable material.

[0010] As used herein, the term "cosmetic composition" refers to a product that is applied to human skin, nails, hair, etc., and is used for cosmetic purposes.

[0011] However, it will be appreciated that the term "composition" also refers to other applications including cosmetic compositions, as well as insecticides, paints, coatings, inks, adhesives, and the like, among others.

[0012] As used herein, the terms "weight percent (wt%)," "percent by weight," "% by weight," and similar terms refer to the concentration of a substance as the weight of that substance divided by the weight of the composition multiplied by 100.

[0013] The term "about" preceding a numerical value includes up to ±10% of that numerical value. It is to be understood that the value to which the term "about" refers is itself specifically and preferably disclosed.

[0014] The term "alkyl" refers to a straight-chain or branched-chain alkyl group. Exemplary alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.

[0015] The term “halogen” means F, Cl, Br, or I.

[0016] 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 undue toxicity, irritation, allergic reactions, 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 are well known in the art. For example, SM Berge et al. provide a detailed description of pharmaceutically or biologically acceptable salts 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 inorganic and organic 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 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 include the salts of amino groups formed with such inorganic acid examples.Another example of pharmaceutically or biologically acceptable acid is carboxylic acid, and the carboxylated product of PEFA compounds contains a 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.

[0017] Salts derived from appropriate bases include alkali metal salts, alkaline earth metal salts, ammonium salts, and N(C 1~4 Alkyl) 4 Representative alkali or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium, etc. Further pharma- ceutically or biologically acceptable salts include ammonium, quaternary ammonium, and amine cations formed with counterions such as halides, hydroxides, carboxylates, sulfates, phosphates, nitrates, lower alkylsulfonates, and arylsulfonates, where appropriate.

[0018] The present disclosure includes both the (R) and (S) configurations at each stereocenter, whether drawn according to the definition or not. Additionally, the present disclosure includes racemic compositions of the compounds disclosed herein. Additionally, the present disclosure includes scalemic compositions of the compounds disclosed herein. Additionally, the present disclosure includes enantiomerically enriched compositions of the compounds disclosed herein.

[0019] The polyol lipid biosurfactants described herein can include polyol esters of fatty acids (PEFAs).

[0020] Polyol lipids can be isolated and / or purified from yeast cultures according to methods well known in the art. Because polyol lipids are secreted extracellularly from yeast cells, one or more polyol lipids can be isolated and / or purified from yeast cell cultures without cell lysis or extraction involving organic solvents.

[0021] Fatty acid polyol esters are amphipathic molecules that contain a sugar alcohol (e.g., D-mannitol and / or D-arabitol) esterified to the carboxyl terminus of a 3-hydroxy fatty acid acyl moiety, which may or may not be acetylated. Similarly, the non-esterified hydroxyl group of the sugar alcohol may or may not be acetylated. In some embodiments, the one or more polyol lipids produced are a mixture of similar compounds containing (R)-3-hydroxy fatty acid acyl moieties with different chain lengths, with carbon numbers ranging from about 8 to 24, preferably from 12 to 20. In some embodiments, the (R)-3-hydroxy fatty acid acyl moieties may exhibit different degrees of unsaturation ranging from about 0 to 6, e.g., from 2 to 5. In some embodiments, the non-esterified hydroxyl group of the sugar alcohol may be esterified to an acetyl group. In some embodiments, the sugar alcohol may be fully acetylated. In some embodiments, the sugar alcohol may not be acetylated. In some embodiments, the acetylation may vary in a range between these two states.

[0022] In some embodiments, the polyol lipid disclosed herein is an acetylated C12:0-3-hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 2 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol with 2 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, the 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 disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 2 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations.In some embodiments, the 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, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-arabitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol with 5 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C18:0-3-hydroxy fatty acid esterified to D-arabitol with 4 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C20:0-3-hydroxy fatty acid esterified to D-mannitol with 3 acetylations. In some embodiments, the polyol lipid disclosed herein is an acetylated C20:0-3-hydroxy fatty acid esterified to D-mannitol with 4 acetylations.

[0023] Exemplary Compounds In some embodiments, the polyol lipid is a PEFA compound represented by a compound selected from the group consisting of: [ka] or a salt or acid thereof.

[0024] In some embodiments, the polyol lipid is a PEFA compound represented by formula (I) or (II): [ka] or [ka] or a salt or acid thereof, 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 R2 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 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)(C2 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 -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 -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 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 kO m ) selected from the group consisting of Each R x is independently C 1 ~C 3 is alkyl, R x is optionally substituted with 1 to 7 halogens; Each R y are independently -H, C 1 ~C 3 is alkyl, R x is 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.

[0025] In some embodiments, the polyol lipid comprises a PEFA compound of formula (I) or (II): [ka] or [ka] or a salt or acid thereof, 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)(C2 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 ) selected from the group consisting of 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 ) 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 , -(O)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 kO m ) selected from the group consisting of 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 ) 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 is alkyl, R x is optionally substituted with 1 to 7 halogens; Each R y are independently -H, C 1 ~C 3 is alkyl, R x is 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; each p is independently selected from 1 to 10; however, 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 When is OH, R 1 is (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 is -(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.

[0026] In some embodiments, a compound of formula (I) or (II), 1 -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 , and -(O)S(O 2 )OH; R 2 -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 , and -(O)S(O 2)OH; R 3 -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 , and -(O)S(O 2 )OH; R 4 -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 , and -(O)S(O 2 )OH; R 5 -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 , and -(O)S(O 2 )OH; R a -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 , and -(O)S(O2 )OH; Each R x is independently C 1 ~C 3 is alkyl, R x is optionally substituted with 1 to 7 halogens; Each R y are independently -H, C 1 ~C 3 is alkyl, R x is optionally substituted with 1 to 7 halogens; n is 2 to 11; each p is independently selected from 1 to 10].

[0027] In some embodiments, the polyol lipid is a PEFA compound represented by formula (Ia) or (II-a): [ka] or [ka] or a salt or acid thereof.

[0028] R 1 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)Ry , -(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 , and -(O)(C j H k O m ) (However, -(C j H k O m In some embodiments, R 1 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 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 is -Ac. 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 ).

[0029] R 2 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 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 , and -(O)(C j H k O m ) where -(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 , -(C2 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 is -Ac. In some embodiments, R 2 -R x In some embodiments, R 2 is -C(O)OR y In some embodiments, R 2 is -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 ).

[0030] R 3 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(O2 )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 , and -(O)(C j H k O m ) where -(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 is -Ac. In some embodiments, R 3 -R x In some embodiments, R 3 is -C(O)OR yIn 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 ).

[0031] R 4 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 , and -(O)(C j H k O m) where -(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 is -Ac. 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 H 5 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 ).

[0032] R 5 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 , and -(O)(C j H k O m ) where -(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 5 is -P(O)(OH) 2 , or -S(O2 )OH. In some embodiments, R 5 is -C(O)R x In some embodiments, R 5 is -Ac. 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 ).

[0033] R a 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)R x , -(O)R x , -(O)C(O)OR y , -(O)C(O)N(H)R y , -(O)(C2 H 5 O) p R y , -(O)P(O)(OH) 2 , -(O)S(O 2 )OH, -(O)NO 2 , -(O)NH 2 , and -(O)(C j H k O m ) where -(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 a 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 is -Ac. 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 a is -P(O)(OH) 2In some embodiments, R a is -S(O 2 )OH. In some embodiments, R a is -(C j H k O m ).

[0034] R x In some embodiments, each R x is independently C 1 ~C 3 is alkyl, R x is optionally substituted with 1 to 7 halogens. In some embodiments, R x is methyl, R x is optionally substituted with 1 to 7 halogens. In some embodiments, R x is ethyl, and R x is optionally substituted with 1 to 7 halogens. In some embodiments, R x is n-propyl, R x is optionally substituted with 1 to 7 halogens. In some embodiments, R x is i-propyl, R x is optionally 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.

[0035] R y In some embodiments, each R y are independently -H or C 1 ~C 3 is alkyl, R y is optionally substituted with 1 to 7 halogens. In some embodiments, R y is -H. In some embodiments, each R y is independently C1 ~C 3 is alkyl, R y is optionally substituted with 1 to 7 halogens. In some embodiments, R y is methyl, R y is optionally substituted with 1 to 7 halogens. In some embodiments, R y is ethyl, R y is optionally substituted with 1 to 7 halogens. In some embodiments, R y is n-propyl, R y is optionally substituted with 1 to 7 halogens. In some embodiments, R y is i-propyl, R y is optionally 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.

[0036] In some embodiments, the polyol lipid is [ka] or a salt or acid thereof.

[0037] Preparation of compounds Below are examples of specific embodiments of the invention described in this disclosure. These examples are presented for illustrative purposes only and are not intended to limit the scope of the invention in any way. The groups referred to in the examples below (e.g., OR 1 , OR 2 etc.) may be replaced with corresponding groups as described herein (e.g., R 1 , R 2etc.), which may be replaced with 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 be allowed for.

[0038] In some embodiments, compounds of the present disclosure can be prepared as shown in Schemes 1 or 2. [ka] [ka]

[0039] In some embodiments, compounds of the present disclosure can be prepared as shown in Schemes 3 or 4. [ka] [ka]

[0040] In some embodiments, compounds of the present disclosure can be prepared as shown in Schemes 5 or 6. [ka] [ka]

[0041] Synthesis / isolation of starting materials for the compounds described herein can be found in WO2018148465 and WO2017184884, each of which is incorporated by reference in their entirety.

[0042] Non-limiting example of the preparation of hydroxy-dodecanoic acid 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl ester: [ka]

[0043] Non-limiting example of the preparation of D-mannitol 1-phosphate: D-mannitol and P 2 O 5 is heated neat at 100°C for 6 hours. As an example, D-mannitol 1-phosphate can be prepared as shown in J.-G. Nam et al. Materials Chemistry and Physics 116(2009) 46-51. D-mannitol 1-phosphate and 3-hydroxydodecanoic acid can be mixed together to prepare N-mannitol 1-phosphate as shown in Wenyuan Han et al. Polymers 11,(2019), 1031. 2 Heat at 170°C for 4 hours.

[0044] emulsifier An emulsifier comprising at least one polyol lipid can be used to stabilize a water-in-oil emulsion. The emulsifiers described herein can comprise at least one polyol lipid that is used to stabilize an oil-in-water emulsion.

[0045] In some embodiments, the emulsifier is inert so as not to react with other components of the product or system into which it is introduced. In some embodiments, the emulsifier reacts minimally with components of the product or system into which it is introduced. In some embodiments, the emulsifier does not adversely affect the product or system. In some embodiments, the emulsifier has minimal adverse effects on the product or system. In some embodiments, the emulsifier is present in the final product of the reaction procedure. In some embodiments, the emulsifier is physiologically safe or has a biologically acceptable safety profile. In some embodiments, the emulsifier is biodegradable and / or environmentally safe or environmentally acceptable.

[0046] In some embodiments, the emulsifier has an HLB value ranging from 0 to 12 to form a water-in-oil emulsion. In some embodiments, the emulsifier has an HLB value ranging from 6 to 18 for an oil-in-water emulsion. In some embodiments, the emulsifier can be mixed with another emulsifier to stabilize the emulsion in the final product. In some embodiments, the additional emulsifier can include a PEFA compound, while in other embodiments, the additional emulsifier can exclude a PEFA compound.

[0047] The emulsifiers and water-in-oil emulsions disclosed herein offer advantages over other conventional agents and formulations in that they maintain emulsion stability over time or when exposed to heat, while being renewable, less toxic, and / or more biodegradable, allowing for improved formulation of end consumer products.

[0048] The emulsifier can include at least one polyol lipid.In some embodiments, at least one polyol lipid is a PEFA compound.The PEFA compound can include one of the PEFA compounds described herein, including those represented by formula (I), (II), (Ia) or (II-a).

[0049] In some embodiments, the emulsifier can comprise two or more polyol lipids.In some embodiments, the two or more polyol lipids are fatty acid polyol ester (PEFA) compounds.In some embodiments, the two or more polyol lipids are selected from the PEFA compounds described herein, including those represented by formula (I), (II), (Ia) or (II-a).

[0050] The emulsion can be formed of an oil component and a water component. In some embodiments, the method can include adding two or more polyol lipids selected from the PEFA compounds described herein, including those represented by formula (I), (II), (Ia), or (II-a).

[0051] The emulsifier may be provided in a variety of forms. For example, the emulsifier may be provided in a dry form. In some embodiments, an effective amount of emulsifier may be added to the product mixture to form a stable emulsion. The effective amount depends on the amount of fat or oil that needs to be stably dispersed in the emulsion. The effective amount may also depend on the type of emulsion used. In some embodiments, the effective amount added is about one-half to one-third of the amount that would be required if a conventional emulsifier were used. For example, to emulsify 10% oil by weight, 5 weight percent (wt%) of emulsifier may be provided instead of 15% by weight.

[0052] In some embodiments, the emulsifier may comprise a pentitol polyol ester of fatty acids and a hexitol polyol ester of fatty acids. In some embodiments, the C16 and C18 fatty acid components of the pentitol and hexitol polyol esters may comprise about 20% to about 99% of the PEFA, 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 and hexitol polyol esters may comprise about 50% or more of the PEFA, in some embodiments, about 60% or more of the PEFA, 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, and in some embodiments, the ratio is about 50:1 or greater.

[0053] Water-in-oil and oil-in-water emulsions The water-in-oil emulsion can include at least one polyol lipid.In some embodiments, at least one polyol lipid is a PEFA compound.In some embodiments, at least one polyol lipid is selected from the PEFA compounds described herein, including those represented by formula (I), (II), (Ia) or (II-a).

[0054] In some embodiments, the water-in-oil emulsion can comprise two or more polyol lipids. In some embodiments, the oil-in-water emulsion can comprise two or more polyol lipids. In some embodiments, the two or more polyol lipids are PEFA. In some embodiments, the two or more polyol lipids are selected from the PEFA compounds described herein, including those represented by formula (I), (II), (Ia) or (II-a).

[0055] The water-in-oil and oil-in-water emulsions can further include a solvent, a carrier, an additive, a stabilizer, a surfactant, an emulsifier, or a combination thereof.

[0056] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion can each further comprise a solvent. Such a solvent can be selected to dissolve or disperse at least one polyol lipid. Suitable solvents include any of a variety of solvents that solubilize but do not significantly decompose at least one polyol lipid.

[0057] Non-limiting examples of solvents include hydrocarbons (both aromatic and aliphatic), oxygenated solvents (alcohols, ketones, aldehydes, ethers, glycol ethers, esters, and glycol ether esters), polyalkylene oxides, capped polyalkylene oxides, and combinations thereof. Suitable polyalkylene oxides include polyethylene glycol, polypropylene glycol, polybutylene glycol, mixtures thereof, and the like. Suitable capped polyalkylene oxides include monoalkyl and dialkyl ethers of the respective polyalkylene oxides, such as monomethyl and dimethyl ethers of polyalkylene glycols, monoethyl and diethyl ethers of polyalkylene glycols, monopropyl and dipropyl ethers of polyalkylene glycols, monobutyl and dibutyl ethers of polyalkylene glycols, mixtures thereof, and the like. Suitable capped polyalkylene oxides include methyl polyethylene glycols (e.g., monomethyl ethers of polyethylene glycols), dimethyl polyethylene glycols (e.g., dimethyl ethers of polyethylene glycols), mixtures thereof, and the like.

[0058] Suitable carriers 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 DOWANOL 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 available from Union Carbide Corp., include butoxyethyl PROPASOL™, butyl CARBITOL™ acetate, butyl CARBITOL™, butyl CELLOSOLVE™ acetate, butyl CELLOSOLVE™, butyl DIPROPASOL™, butyl PROPASOL™, CARBITOL™ PM-600, CARBITOL™ low gravity, CELLOSOLVE™ acetate, CELLOSOLVE™, Ester EEP™, FILMER These include 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™.

[0059] Each of the water-in-oil emulsion and the oil-in-water emulsion can further comprise a carrier. The carrier can provide a medium for dissolving, suspending, or carrying other components of the emulsion composition. For example, the carrier can provide a medium for solubilizing, suspending, or producing polyol lipids and for forming an equilibrium mixture. The carrier can also function to deliver the antimicrobial component of the emulsion composition of the present invention onto an object. To this end, the carrier can contain one or more optional components that can facilitate such delivery and perform additional functions of the emulsion composition.

[0060] In certain embodiments, the carrier mainly comprises water, which can promote dissolution and act as a medium for reaction and equilibration.Non-limiting examples of carriers can include one or more of hydrocarbon oils, water, aliphatic alcohols and esters, and organic solvents, such as simple alkyl alcohols, such as ethanol, isopropanol, n-propanol, etc.

[0061] In certain embodiments, the carrier comprises the majority of either the water-in-oil or oil-in-water emulsion. The concentration and type of carrier will depend on the nature of the formulation, storage environment, and application method, including the concentration of polyol lipid, among other factors.

[0062] In certain embodiments, the water-in-oil emulsion comprises from about 0 to about 98% by weight of the carrier, from about 0.001 to about 99.99% by weight of the carrier, from about 0.2 to about 60% by weight of the carrier, from about 1 to about 98% by weight of the carrier, from about 5 to about 99.99% by weight of the carrier, from about 5 to about 97% by weight of the carrier, from about 5 to about 90% by weight of the carrier, from about 5 to about 70% by weight of the carrier, from about 5 to about 20% by weight of the carrier, from about 10 to about 90% by weight of the carrier, from about 10 to about 80% by weight of the carrier, from about 10 to about 5 ... 0% by weight of the carrier, about 10 to about 20% by weight of the carrier, about 15 to about 70% by weight of the carrier, about 15 to about 80% by weight of the carrier, about 20 to about 70% by weight of the carrier, about 20 to about 50% by weight of the carrier, about 20 to about 40% by weight of the carrier, about 20 to about 30% by weight of the carrier, about 30 to about 75% by weight of the carrier, about 30 to about 70% by weight of the carrier, about 40 to about 99.99% by weight of the carrier, about 40 to about 90% by weight of the carrier, or about 60 to about 70% by weight of the carrier.

[0063] In certain embodiments, the oil-in-water emulsion comprises from about 0 to about 98% by weight of the carrier, from about 0.001 to about 99.99% by weight of the carrier, from about 0.2 to about 60% by weight of the carrier, from about 1 to about 98% by weight of the carrier, from about 5 to about 99.99% by weight of the carrier, from about 5 to about 97% by weight of the carrier, from about 5 to about 90% by weight of the carrier, from about 5 to about 70% by weight of the carrier, from about 5 to about 20% by weight of the carrier, from about 10 to about 90% by weight of the carrier, from about 10 to about 80% by weight of the carrier, from about 10 to about 5 ... 0% by weight of the carrier, about 10 to about 20% by weight of the carrier, about 15 to about 70% by weight of the carrier, about 15 to about 80% by weight of the carrier, about 20 to about 70% by weight of the carrier, about 20 to about 50% by weight of the carrier, about 20 to about 40% by weight of the carrier, about 20 to about 30% by weight of the carrier, about 30 to about 75% by weight of the carrier, about 30 to about 70% by weight of the carrier, about 40 to about 99.99% by weight of the carrier, about 40 to about 90% by weight of the carrier, or about 60 to about 70% by weight of the carrier.

[0064] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion each can further comprise one or more additives, non-limiting examples of which include ethylene oxide / propylene oxide block copolymers, butylene oxide / propylene oxide block copolymers, ethylene oxide / butylene oxide block copolymers, waxes, or silicone-based materials.

[0065] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion can each further comprise a stabilizer. The shelf life of the water-in-oil emulsion or the oil-in-water emulsion disclosed herein can be improved by including a stabilizer and / or a preservative to prevent bacterial spoilage. Non-limiting examples of stabilizers include oleic acid, hexylene glycol, fatty alcohols, naphthalene sulfonates, butyl alcohol, and formaldehyde.

[0066] In some embodiments, surfactants or secondary emulsifiers are selected to be added to water-in-oil or oil-in-water emulsions to improve the wettability of the emulsion. For example, improved wettability is useful when such emulsions are applied to food products or when such emulsions are formed with at least one polyol lipid. In some embodiments, such surfactants or secondary emulsifiers can be anionic, cationic, nonionic, or amphoteric, and combinations thereof. Non-limiting examples of anionic surfactants or secondary emulsifiers include alkali metal, ammonium, and amine soaps, and preferably the fatty acid portion of such soaps contains at least 16 carbon atoms. Other non-limiting examples of anionic surfactants or secondary 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, didodecylamine lactate, acetate of aminoethyl-aminoethylstearamide, dilauroyltriethylenetetramine diacetate, 1-aminoethyl-2-heptadecenylimidazoline acetate; and quaternary salts, such as cetylpyridinium bromide, hexadecylethylmorpholinium chloride, and diethyldidodecylammonium 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 isooctylphenol with 12 ethylene oxide units; condensation products of higher fatty acid amides with 5 or more ethylene oxide units; polyethylene glycol esters of long chain fatty acids, such as tetraethylene glycol monopalmitate, hexaethylene glycol monolaurate, nonaethylene glycol monostearate, nonaethylene glycol dioleate, tridecaethylene glycol monoarachidate, tricosaethylene glycol monobehenate, tricosaethylene glycol dibehenate, partial higher fatty acid esters of polyhydric alcohols, such as Examples include sorbitan tristearate, ethylene oxide condensation products of partial higher fatty acid esters of polyhydric alcohols, and their internal anhydrides (mannitol anhydride (also called mannitan) and sorbitol anhydride (also 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 to 15 molecules of ethylene oxide, and mannitan monopalmitate reacted with 10 to 15 molecules of ethylene oxide; long-chain polyglycols in which one hydroxyl group is esterified with a higher fatty acid and the other hydroxyl group is etherified with a low-molecular-weight alcohol, such as methoxypolyethylene glycol 550 monostearate (550 means the average molecular weight of the polyglycol ether). Non-limiting examples of amphoteric surfactants include alkyl betaines, alkyl dimethyl amine N-oxides, alkyl amidopropyl amine N-oxides, alkyl amidopropyl betaines, cocamidopropyl betaine, cocoamphoacetate and cocoamphodiacetate, phosphatidylserine, phosphatidylethanolamine, phosphatidylcholine, sphingomyelin, lauryl dimethylamine oxide, and myristamine oxide.In some embodiments, a combination of two or more of these surfactants may be used, for example, a cationic may be blended with a nonionic, or an anionic may be blended with a nonionic.

[0067] Those skilled in the art will recognize that the individual components of the water-in-oil or oil-in-water emulsions can be modified depending on the physical and chemical properties required for emulsion stability in the particular process and / or application to which the formulation is applied. For example, the water dispersibility of the water-in-oil or oil-in-water emulsions can be adjusted as needed to obtain the desired performance.

[0068] The hydrophilic lipophilic balance (HLB) of an emulsion is a measure of the degree of hydrophilicity or lipophilicity of the emulsion. HLB values ​​are calculated using known methods. In some embodiments, the HLB of the water-in-oil emulsions disclosed herein is 0-12. In some embodiments, the HLB of the water-in-oil emulsions disclosed herein is less than 10. In some embodiments, the water-in-oil emulsions disclosed herein are fat-soluble (water-insoluble). In some embodiments, the HLB of the water-in-oil emulsions disclosed herein is 4-10. In some embodiments, the HLB of the water-in-oil emulsions disclosed herein is 6-8. In some embodiments, the HLB of the water-in-oil emulsions disclosed herein is 3-6.

[0069] In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6-18. In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of less than 18. In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of less than 12. In some embodiments, the oil-in-water emulsions disclosed herein are fat-soluble (water-insoluble). In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6-12. In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6-8. In some embodiments, the polyol lipid has an HLB of less than 12.

[0070] As described herein, the emulsifier can be formed from one polyol lipid with a PEFA compound. As a primary emulsifier, the described emulsifier can reduce the interfacial tension to obtain a smaller droplet size. This allows the emulsifier to effectively provide steric stabilization after the W / O or O / W emulsion is formed. As a primary or sole emulsifier, the described emulsifier can, in certain embodiments, have an HLB value of about 8 to about 10, and in certain embodiments, an HLB value of about 9.

[0071] The emulsifiers described herein may also function as co-emulsifiers with another PEFA-based emulsifier or a non-PEFA-based emulsifier. In certain embodiments, the PEFA-based emulsifier enhances emulsification when mixed with another emulsifier having a similar HLB value. For example, each of the co-emulsifiers has, in certain embodiments, an HLB value ranging from about 6 to about 12, in certain embodiments, an HLB value of about 8 to about 10, and in certain embodiments, an HLB value of about 9. Applications

[0072] The emulsifiers and related compositions described herein are particularly relevant to food and beverage applications, as well as cosmetic and skin applications, home care, personal care, industrial cleaning, automotive care, oil fracking, pharmaceuticals, agriculture (e.g., pesticides), paints, adhesives, sealants, coatings, inks, flavors and fragrances.

[0073] food / beverage The methods and processes described herein are effective in homogeneously mixing immiscible substances such as oil and water to produce stable emulsions with extended shelf life and improved yeast and mold preservation in the manufacture of various substances, such as food products, as compared to similar methods or processes that do not use the fatty acid polyol esters (PEFAs) described herein. An important consideration in food production is that the emulsifier used does not impart off-flavors or other negative characteristics to the food product. Without being limited by theory, it is expected that the methods and processes disclosed herein have the characteristics of (1) providing a stable emulsion and / or (2) imparting a neutral taste to the final food product.

[0074] In some embodiments, the emulsifier, including the PEFA compounds described herein, can be added to the food product in an amount sufficient to obtain the required level of stable emulsion for the process. It is recognized that different food processing techniques require different amounts of emulsifier to obtain the desired results. In some embodiments, the amount of emulsifier added to the food product is measured as a percentage of the combined weight of the emulsifier and the food product (total weight of the food composition). In some embodiments, the amount of emulsifier is about 0.001-0.5 weight percent of the total weight of the food composition, or about 0.01-5 weight percent of the total weight of the food composition. In some embodiments, the amount of emulsifier is about 0.1-1 weight percent of the total weight of the food composition. In some embodiments, the amount of emulsifier is about 0.01-2 weight percent of the total weight of the food composition, or about 0.01-1 weight percent of the total weight of the food composition.

[0075] Non-limiting examples of food products in which a stable emulsion is desirable include flavored carbonated or non-carbonated soft drinks, dairy-based beverages, soy beverages, teas, fruit beverages, flavored juices, sports drinks (e.g., Gatorade®), alcoholic beverages, and non-beverage foods such as baked goods, syrups, flavored oil emulsions, salad dressings, mayonnaise, dairy products, ice cream, various pates, confectioneries, jams, and jellies. For example, emulsifiers can be used to stabilize flavor emulsions in beverages such as carbonated soft drinks. Other beverages can also be produced using emulsifiers.

[0076] Further non-limiting examples of food products in which stable emulsions are desirable include beverages in the form of instant powder mixes, as well as liquid concentrates that must be reconstituted with other liquids, such as milk, water, and juice, prior to consumption.

[0077] Non-limiting examples of food-based processes in which stable emulsions are desirable include food processing such as rheology modifiers in dough, pasta, and other food applications.

[0078] Non-limiting examples of food-based processes in which stable emulsions are desirable include the industrial processing of sugar beets in processing equipment during washing, cutting, spreading, carbonization, and evaporation steps (leading to the formation of sugar, syrup, and juice); the industrial processing of potatoes in processing equipment during washing, scouring, polishing, and cutting, and industrial fermentation processes, including fermentation.

[0079] Further non-limiting examples of processes include food processing such as cleaning agents for fresh and frozen fruits, vegetables, meats, and processed foods, food processing such as rheology modifiers in food applications including doughs, pastas, and food processing such as anti-adhesion agents.

[0080] In some embodiments, the food compositions or beverages disclosed herein are free of petroleum-based surfactants.

[0081] In some embodiments, the food compositions or beverages disclosed herein may have one or more improved properties compared to food compositions or beverages containing conventional emulsifiers. In some embodiments, the one or more improved properties may be selected from the group including higher solubility, improved emulsifying ability, higher emulsion particle stability, higher emulsion particle size stability, higher viscosity stability, or improved texture and / or feel upon use.

[0082] In some embodiments, the food product comprises an emulsifier disclosed herein and / or a water-in-oil emulsion disclosed herein and / or an oil-in-water emulsion disclosed herein, in an amount sufficient to provide long-term emulsion stability and emulsion stability upon exposure to heat required for processing. It is recognized that different food processing techniques provide different levels of emulsion stability and therefore require different amounts of emulsifier and / or water-in-oil emulsion and / or oil-in-water emulsion to achieve the desired results.

[0083] Cosmetics / Skin Polyol lipid disclosed herein can be used in cosmetic and dermatological compositions due to its skin-friendly properties.The possible application forms of cosmetic and dermatological compositions that contain at least one polyol lipid can include sprays, lotions, creams, ointments, and therefore can include the use of a very wide range of consistency, from watery to thick paste-like or solid.

[0084] Non-limiting examples of cosmetic and dermatological compositions include creams, foams, mousses, balms, ointments, masks, personal care formulations such as shampoos, body washes, conditioners, soaps, creams, skin treatments, and moisturizers.

[0085] Further non-limiting examples of cosmetic and dermatological compositions include face, body and hand care creams and lotions, sunscreen emulsions, make-ups, aerosols, roll-ons, pump sprays, sticks, e.g. in the antiperspirant / deodorant field, baby care products, intimate care products, foot care products, hair care products, nail care products, dental care products or oral care products, as well as skin ointments.

[0086] In some embodiments, cosmetic and dermatological compositions may include polyol lipids. Such polyol lipids may further include one or more cosmetic active ingredients. Non-limiting examples of cosmetic or bioactive ingredients include phytosphingosine (and phytosphingosine derivatives), sphingosine (and sphingosine derivatives), sphingolipids, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, polyphenols, deoxyribonucleic acid, coenzyme Q10, retinol, AHA acids, amino acids, hyaluronic acid, alpha-hydroxy acids, flavones, isoflavones, stilbenes, catechins, polyglutamic acid, Examples of such antioxidants include creatine (and creatine derivatives), guanidine (and guanidine derivatives), pseudoceramides, essential oils and fatty acids, peptides, preferably peptides containing 2 to 10 amino acids, oligopeptides, protein hydrolysates, plant extracts, bisabolol, allantoin, panthenol, phytantriol, idebenone, licorice extract, plant extracts, glycyrrhizidine and idebenone, scleroglucan, β-glucan, santalbic acid, and vitamin complexes.

[0087] In some embodiments, the cosmetic or dermatological compositions disclosed herein are free of petroleum-based surfactants.

[0088] In some embodiments, the cosmetic or dermatological compositions disclosed herein have one or more improved properties compared to conventional agents. In some embodiments, the one or more improved properties are selected from the group including higher solubility, improved emulsifying ability, higher emulsion particle stability, higher emulsion particle size stability, higher viscosity stability, or improved texture and / or feel upon use.

[0089] In some embodiments, the cosmetic or dermatological composition comprises an emulsifier disclosed herein and / or a water-in-oil emulsion disclosed herein and / or an oil-in-water emulsion disclosed herein, in an amount sufficient to provide emulsion stability over time and when exposed to heat required for processing. It is recognized that different cosmetic and dermatological compositions require different levels of emulsion stability to achieve the desired results and therefore different amounts of emulsifier and / or water-in-oil emulsion and / or oil-in-water emulsion.

[0090] In some embodiments, the cosmetic or skin composition comprising the emulsifier disclosed herein and / or the water-in-oil emulsion disclosed herein and / or the oil-in-water emulsion disclosed herein has improved properties compared to conventional agents. Non-limiting examples of improved properties include high solubility, improved emulsification performance, high stability of emulsion particles, high stability of emulsion particle size, improved wettability, improved suspension, high viscosity stability, and improved feel and / or sensation during use (e.g., improved feel, improved use, persistent suppression of oiliness, maintenance of moisture retention after application, and no stickiness, etc.). EXAMPLES

[0091] Below are examples of specific embodiments for carrying out the present specification. These examples are provided for illustrative purposes only and are not intended to limit the scope of the present invention in any way. Efforts have been made to ensure accuracy with respect to the numbers used (e.g., amounts, temperatures, etc.), but some experimental error and deviation should be allowed for.

[0092] Wetting or dispersing agent properties can be important in identifying effective emulsifiers for cosmetic or dermatological applications. For example, dispersing properties can ensure the stability of a composition throughout the manufacturing, storage, and application process. Such emulsifiers can effectively and uniformly disperse particles in a solution, preventing unwanted clumping, by adequately "wetting" the particles through adequate displacement of air around the solid particles. The emulsifiers described herein provide improved performance when evaluated for such wetting or dispersing properties compared to other known W / O emulsion compositions. For example, sorbitan sesquioleate (e.g., SPAN™ 83) is a well-known W / O emulsion composition that has been used in personal care compositions, such as those used in cosmetic or dermatological applications. As shown in FIG. 1, the vial on the left (Vial 1) contains 20% ZnO particles added to Emulsifier A of the present invention, and the vial on the right (Vial 2) contains 20% ZnO particles suspended in SPAN™ 83. Figure 1 shows the time immediately after the vials were stirred, and both vials show emulsion systems with ZnO particles suspended. Figure 2 shows these same two vials after one week of storage at 60°C. As can be seen, the ZnO particles remain suspended in vial 1 containing the inventive emulsifier A, whereas in vial 2 containing the known emulsion composition, the ZnO particles have settled to the bottom, indicating phase separation and instability. These results show the improved performance of the inventive emulsifier A compared to SPAN™ 83.

[0093] Moreover, the composition in vial 2 is darkened and has a yellowish or brownish coloration, whereas the color of vial 1 remains white after one week, indicating improved stability. Stability is an important property of compositions used in personal care and food compositions, and is related to the shelf life of the product and the uniform dispersion of active substances. Therefore, emulsifier A of the present invention is expected to provide improved shelf life and better sun protection factor (SPF) to any emulsion composition and related products where such benefits are sought.

[0094] Tables 1-7 provide examples of the wide range of applications in which the inventive emulsions described herein can be used. As noted herein, the emulsifiers and related compositions described herein are relevant to many industries and can be used in lotions, skin creams, conditioners, facial cleaners, and surface cleansers, among other compositions.

[0095] Among other benefits, the emulsions of the present invention described herein can help provide stability to emulsion compositions. For example, Table 1 shows the formulation of a lotion emulsion composition including emulsifier B of the present invention. Emulsifier B of the present invention can reduce the interfacial tension, allowing for small droplet sizes. Additionally, emulsifier B of the present invention can form a steric barrier around the droplets, and in combination with xanthan gum, can provide stability of the emulsion composition to room temperature and high temperature conditions for extended periods of time. Specifically, when emulsifier B of the present invention is used, the lotion emulsion composition was found to be stable for 4 weeks at room temperature, 40°C, and 45°C. [Table 1]

[0096] To formulate the lotion of Table 1, water is heated to 75°C. Separately, the emulsifier B of the present invention and the emollient are mixed and then heated to 75°C. Next, the humectant, thickener, and preservative are mixed together and added to the water while stirring with an impeller. The mixture of emulsifier B of the present invention and the emollient is then added to the remaining ingredients while stirring, and mixing is continued without heating. The ingredients are homogenized until a glossy appearance is observed.

[0097] Table 2 shows the formulation of another lotion emulsion composition containing emulsifier C of the present invention. [Table 2]

[0098] Table 3 shows the formulation of a skin cream emulsion composition containing emulsifier D of the present invention. [Table 3]

[0099] Table 4 shows the formulation of a rinse-out hair conditioner emulsion composition containing emulsifier E of the present invention. [Table 4]

[0100] Table 5 shows the formulation of a leave-in hair conditioner emulsion composition containing emulsifier F of the present invention. [Table 5]

[0101] Table 6 shows the formulation of a surface cleaner emulsion composition containing emulsifier G of the present invention. [Table 6]

[0102] Table 7 shows the formulation of a make-up remover emulsion composition containing emulsifier H of the present invention. [Table 7]

[0103] Emulsifier evaluation The HLD parameters are determined using methods known in the art (e.g., the mixture method), and the HLB measurements are also determined according to methods known in the art, as described above (e.g., calculation Davies and Lin group contribution method according to Kothencz et al. (2017) Studia Universitatis Babes-bolyai Chemia 62: 451-458).

[0104] Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific inventive embodiments described herein. The scope of the present invention is not limited to the above description, but rather is as set forth in the appended claims.

[0105] In the claims, the articles "a," "an," and "the" may mean one or more, unless otherwise indicated or otherwise clear from the context. A claim or description containing "or" between one or more elements of a group is deemed to be satisfied if one, more than one, or all of the group members are present in, employed in, or otherwise relevant to a particular product or process, unless otherwise indicated or otherwise clear from the context. The invention includes embodiments in which exactly one element of the group is present in, employed in, or otherwise relevant to a particular product or process. The invention includes embodiments in which more than one, or all elements of the group are present in, employed in, or otherwise relevant to a particular product or process.

[0106] It should also be noted that the term "comprising" is intended to be open, allowing but not requiring that additional elements or steps be included. Thus, when the term "comprising" is used herein, the term "consisting of" is also included and disclosed.

[0107] When ranges are given, the endpoints are included. Furthermore, unless otherwise indicated or otherwise clear from the context and the understanding of one of ordinary skill in the art, values ​​expressed as ranges are understood to be able to take any particular value or subrange within the ranges set forth in different embodiments of the invention, to the tenth of the unit of the lower limit of the range, unless the context clearly indicates otherwise.

[0108] All cited documents, e.g., references, publications, databases, database entries, and art cited herein, are incorporated by reference into this application, even if not expressly stated in the citation. In the event of a conflict between the cited documents and this application, the disclosure of this application shall control.

[0109] The section and table headings are not intended to be limiting.

[0110] The words which have been used are words of description rather than of limitation, and it will 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.

[0111] While the invention has been described at some length and in some detail with respect to certain described embodiments, it is not intended that the invention be limited to 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 accord such claims the broadest possible interpretation in view of the prior art, thereby effectively encompassing the intended scope of the invention.

[0112] 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. An emulsifier comprising one or more polyol lipids, wherein the one or more polyol lipids are fatty acid polyol ester (PEFA) compounds represented by formula (I) or (II): 【Chemistry 1】 or 【Chemistry 2】 or selected from their salts or acids, wherein, 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 , and -(O)(C ｊ H ｋ O ｍ ) and is 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 ２ｊ－１ O ｊ－１ ) 、－ (C ｊ H ｋ O ｍ (C ｘ -O), -OH, -(O)C(O)R ｘ -(O)R ｙ -(O)C(O)OR ｙ -(O)C(O)N(H)R ２ -(O)(C ５ H ｐ O) ｙ R​​​​​​​​​​​​​​ R ３ は、-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 group R ４ は、-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 group R ５ は、-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 group R ａ は、-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 group Each R ｘ C is independent １ ~C ３ It is alkyl, R ｘ These are sometimes replaced by 1 to 7 halogens. Each R ｙ These are independently -H or C １ ~C ３ It is alkyl, R ｘ These are sometimes 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. Each p is independently selected from 1 to 10. emulsifier.

2. An emulsifier comprising one or more polyol lipids, wherein the one or more polyol lipids a) PEFA compound of formula (I) or (II): 【Transformation 3】 or 【Chemistry 4】 or their salts or acids [In the formula, 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 , and -(O)(C ｊ H ｋ O ｍ Selected from the group consisting of, R ２ は、-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 group R ３ は、-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 group R ４ は、-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 group R ５ は、-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 ) １ ) selected from group R ａ は、-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 group Each R ｘ C is independent １ ~C ３ It is alkyl, R ｘ These are sometimes replaced by 1 to 7 halogens. Each R ｙ These are independently -H and C １ ~C ３ It is alkyl, R ｘ These are sometimes 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. Each p is independently selected from 1 to 10. however, n is 12 or 14, R １ If R is -OH or -(O)Ac, ａ It is not -(O)Ac or -(O)Me, n is 12, R ａ If R is -OH, ２ is not -OH, or n is 12 or 14, R ａ is -OH, and R ２ OH is R ３ OH is 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, R ５ ga-(O)S(O ２ ) If it is OH, ａ is -(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], b) Acetylated C12 esterified with D-arabitol having 3 acetylations: 0-3-hydroxy fatty acid, Acetylated C14 esterified with D-mannitol having 4 acetylations: 0-3-hydroxy fatty acid, Acetylated C16 esterified with D-mannitol having 2 acetylations: 0-3-hydroxy fatty acid, Acetylated C16 esterified with D-arabitol having 2 acetylations: 0-3-hydroxy fatty acid, Acetylated C1 esterified with D-arabitol having 4 acetylations 4:0-3-hydroxy fatty acid, esterified to D-mannitol having 5 acetylated groups C14:0-3-hydroxy fatty acid, esterified to D-mannitol having 3 acetylated groups C16:0-3-hydroxy fatty acid, esterified to D-mannitol having 3 acetylated groups C16:0-3-hydroxy fatty acid, esterified to D-arabitol having 3 acetylated groups C16:0-3-hydroxy fatty acid, esterified to D-mannitol having 4 acetylated groups C16:0-3-hydroxy fatty acid, esterified to D-mannitol having 2 acetylated groups Acetylated C18:0-3-hydroxy fatty acid, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol having 5 acetylated groups, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol having 4 acetylated groups, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol having 2 acetylated groups, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol having 5 acetylated groups, having 4 acetylated groups Acetylated C16:0-3-hydroxy fatty acid esterified with D-arabitol, acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol having 3 acetylated groups, acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol having 4 acetylated groups, acetylated C18:0-3-hydroxy fatty acid esterified with D-arabitol having 3 acetylated groups, acetylated C18:0-3-hydroxy fatty acid esterified with D-mannitol having 5 acetylated groups,A group consisting of acetylated C18:0-3-hydroxy fatty acids esterified to D-arabitol having four acetylation groups, acetylated C20:0-3-hydroxy fatty acids esterified to D-mannitol having three acetylation groups, and acetylated C20:0-3-hydroxy fatty acids esterified to D-mannitol having four acetylation groups, or c) 【Transformation 5】 or a group consisting of salts or acids thereof, Selected from, emulsifier.

3. The emulsifier according to claim 1, comprising two or more of the aforementioned polyol lipids.

4. The emulsifier according to claim 1, wherein the n value of the PEFA compound is 4 to 20.

5. The emulsifier according to claim 1, wherein the one or more polyol lipids include pentitol polyol ester, hexitol polyol ester, or a combination thereof.

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

7. The emulsifier according to claim 5, wherein the ratio of pentitol polyol ester to hexitol polyol ester is about 20:1 or more.

8. The emulsifier according to claim 5, wherein the C16 and C18 fatty acid components of the pentitol polyol ester and the hexitol polyol ester can constitute about 20% to about 99% of the PEFA compound.

9. The emulsifier according to claim 5, wherein the C16 and C18 fatty acid components of the pentitol polyol ester and the hexitol polyol ester can constitute about 30% to about 95% of the PEFA compound.

10. The emulsifier according to claim 5, wherein the C16 and C18 fatty acid components of the pentitol polyol ester and the hexitol polyol ester can constitute about 40% or more of the PEFA compound.

11. The aforementioned compound is further of formula (I-a) or (II-a): 【Transformation 6】 or 【Transformation 7】 Or represented by their salts or acids, In the formula, n is between 6 and 12. The emulsifier according to claim 1.

12. An emulsion composition, Water and, oil and, Contains emulsifiers, The emulsifier comprises one or more polyol lipids, wherein the one or more polyol lipids are fatty acid polyol ester (PEFA) compounds represented by formula (I) or (II): 【Transformation 8】 or 【Chemistry 9】 or selected from their salts or acids, During the ceremony, 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 Selected from the group consisting of , -(O)NH2, and -(O)(C j H k O m), 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 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) Selected from the group consisting of OH, -(O)NO2, -(O)NH2, and -(O)(C j H k O m), R3 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, -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), R4 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, -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), R5 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, -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), 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 Selected from the group consisting of , and -(O)(C j H k O m), Each Rx is independently a C1-C3 alkyl, and Rx may be substituted with 1-7 halogens. Each R y is independently -H or C1-C3 alkyl, and R x is optionally substituted with 1-7 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. Each p is independently selected from 1 to 10. Emulsion composition.

13. The emulsion composition according to claim 12, wherein the emulsion composition is a water-in-oil emulsion or an oil-in-water emulsion, and the emulsifier is a primary emulsifier.

14. An emulsion composition according to claim 13, further comprising a secondary emulsifier, wherein the secondary emulsifier is a non-PEFA emulsifier, and the primary emulsifier and the secondary emulsifier have similar HLB values.

15. The emulsion composition according to claim 14, wherein the HLB values ​​of the primary emulsifier and the secondary emulsifier are in the range of about 4 to about 18.

16. An emulsion composition according to claim 12, comprising two or more polyol lipids.

17. An emulsion composition according to claim 12, wherein the emulsion composition is a personal care composition, a food, a beverage, an agricultural composition, a paint, a coating agent, an adhesive, or a sealant.

18. An emulsion composition according to claim 12, wherein the emulsion composition is a cosmetic or a skin composition.

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