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 include a polyol lipid having a fatty acid polyol ester (PEFA) compound.

Description

[0001] Citation of Related Applications

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

[0003] The present disclosure relates to emulsifiers; and water-in-oil emulsion compositions and oil-in-water emulsion compositions having polyol lipids formed from polyol fatty acid esters (PEFA) compounds. Background Art

[0004] Emulsifiers for water-in-oil emulsions exhibit better moisture resistance than oil-in-water emulsions. However, it is more difficult to stabilize water-in-oil emulsions than to stabilize oil-in-water emulsions. In addition, water-in-oil emulsions often suffer from problems with emulsification / dispersion properties (e.g., it is difficult to stabilize the emulsion while maintaining a low emulsion viscosity, and it is difficult to maintain stability in regions with wide temperature variations), and such water-in-oil emulsions are difficult to produce soft touch, smoothness, good spreadability, and good moisture retention. These problems of water-in-oil emulsions are a problem when formulating cosmetic compositions.

[0005] In food processing, the mixture of food components is usually subjected to a series of heat and mechanical treatments, such as baking, boiling, steaming, freezing, kneading, mixing and extruding, to form a food product with required taste, texture and required visual characteristics (such as color and shape). When present in the mixture, the food component may be incompatible with other food components. For example, oil and water are immiscible and form a thermodynamically unstable emulsion when mixed together. The oil phase and the aqueous phase will separate gradually, causing emulsion coalescence, flocculation, emulsification or fragmentation. This may adversely affect the characteristic of the food product, such as shelf life, taste or attractive in appearance.

[0006] An example of an emulsifier for beverages is gum Acacia (gum Arabic), which is prepared from exudates from the stems and branches of sub-Saharan species of Acacia, Acacia senegal, and Acacia seyal. Due to its high demand and unreliable supply, gum Arabic can be difficult to obtain and expensive.

[0007] Therefore, there is a need to develop renewable or biodegradable alternative emulsifiers, water-in-oil (W / O) emulsion compositions, and oil-in-water (O / W) emulsion compositions that have emulsion stability over time when heated or can improve the composition of final consumer products. BRIEF DESCRIPTION OF THE DRAWINGS

[0008] Figure 1 is a photograph depicting a first, left vial with ZnO particles added to an emulsifier according to one embodiment and a second, right vial with ZnO particles added to a conventional emulsifier, both vials being stirred.

[0009] Figure 2 It is a depiction Figure 1 Photograph of vials, both vials having been stored at 60°C for 1 week after stirring.

[0010] Details

[0011] The details of various embodiments of the invention are set forth in the following description. Other features, objects, and advantages of the invention will be apparent from the description and drawings, and from the claims.

[0012] definition

[0013] As used herein, "foodstuff" refers to edible or drinkable material, or material that can be processed into edible or drinkable material.

[0014] 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.

[0015] However, it should be understood that the term "composition" refers to cosmetic compositions as well as other applications, including pesticides, paints, coatings, inks, adhesives, and the like.

[0016] As used herein, weight percent (wt %), weight percent, wt % and the like are synonymous and refer to the concentration of a substance as the weight of the substance divided by the weight of the composition multiplied by 100.

[0017] The term "about" preceding a figure includes plus or minus 10% or less of the value of the figure. It should be understood that the value referred to by the term "about" itself is also specifically and preferably disclosed.

[0018] The term "alkyl" refers to a straight or branched chain alkyl group. Exemplary alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.

[0019] The term "halogen" refers to F, Cl, Br or I.

[0020] As used herein, the term "salt or acid thereof" refers to any salt or acid of a PEFA compound. Exemplary salts and acids of PEFA compounds are suitable for use in contact with tissues of humans and lower animals without undue toxicity, irritation, allergic response, and the like, and are commensurate with a reasonable benefit / risk ratio. Salts may include pharmaceutically or biologically acceptable salts. Likewise, acids may include pharmaceutically or biologically acceptable acids. Pharmaceutically or biologically acceptable salts and acids are well known in the art. For example, SM Berge et al. describe pharmaceutically or biologically acceptable salts in detail in J. Pharmaceutical Sciences, 1977, 66, 1-19, which is incorporated herein by reference. Pharmaceutically or biologically acceptable salts of the compounds of the present disclosure may include those derived from suitable inorganic and organic acids and bases, and pharmaceutically or biologically acceptable acids of the compounds of the present disclosure may include suitable inorganic and organic acids. Examples of pharmaceutically or biologically acceptable inorganic acids may include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid and perchloric acid, or with organic acids such as acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid, propionic acid or malonic acid or by using other methods used in the art such as ion exchange. Examples of pharmaceutically or biologically acceptable acid addition salts are salts of amino groups formed with such examples of inorganic acids. Another example of a pharmaceutically or biologically acceptable acid is a carboxylic acid, wherein the carboxylated form of the PEFA compound includes a carboxyl group. Other pharmaceutically or biologically acceptable salts include adipate, alginate, ascorbate, aspartate, benzenesulfonate, benzoate, bisulfate, borate, butyrate, camphorate, camphorsulfonate, citrate, cyclopentanepropionate, digluconate, dodecylsulfate, ethanesulfonate, formate, fumarate, glucoheptonate, glycerophosphate, gluconate, hemisulfate, heptanoate, hexanoate, hydroiodide, 2-hydroxy-ethanesulfonate, lactobionate, lactate, laurate, lauryl sulfate, malate, maleate, malonate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, oleate, oxalate, palmitate, pamoate, pectinate, persulfate, 3-phenylpropionate, phosphate, pivalate, propionate, stearate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate, and the like.

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

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

[0023] A polyol lipid biosurfactant as described herein may include polyol esters of fatty acids (PEFA).

[0024] Polyol lipids can be separated and / or purified from yeast culture according to methods known in the art. Since polyol lipids are secreted from the yeast cell extracellularly, one or more polyol lipids can be separated and / or purified from yeast cell culture without cell lysis or extraction with an organic solvent.

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

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

[0027] Exemplary compounds

[0028] In some embodiments, the polyol lipid is a PEFA compound represented by a compound selected from the group consisting of:

[0029]

[0030]

[0031] as well as

[0032]

[0033] or a salt or an acid thereof.

[0034] In some embodiments, the polyol lipid is a PEFA compound represented by formula (I) or (II):

[0035]

[0036]

[0037] or its salts or acids,

[0038] in,

[0039] R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0040] R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0041] R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0042] R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0043] R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y, -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0044] R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0045] Each R x are independently C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen;

[0046] Each R y are independently -H, C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen;

[0047] n is 2-20;

[0048] j is 2-12;

[0049] k is 4-26;

[0050] m is 1-16; and each p is independently selected from 1-10.

[0051] In some embodiments, the polyol lipid is a PEFA compound of formula (I) or (II):

[0052]

[0053]

[0054] or its salts or acids,

[0055] in,

[0056] R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0057] R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(Cj H k O m );

[0058] R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0059] R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0060] R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0061] R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2, -(O)(C j H k O m );

[0062] Each R x are independently C1-C3 alkyl, wherein R xoptionally substituted with 1-7 instances of halogen;

[0063] Each R y are independently -H, C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen;

[0064] n is 2-20;

[0065] j is 2-12;

[0066] k is 4-26;

[0067] m is 1-16; and

[0068] Each p is independently selected from 1-10,

[0069] in,

[0070] When n is 12 or 14 and R 1 When it is -OH or -(O)Ac, then R a Not -(O)Ac or -(O)Me;

[0071] When n is 12 and R a When it is -OH, then R 2 Not -OH or;

[0072] When n is 12 or 14, R a Yes -OH, R 2 Yes OH, R 3 is OH, and R 4 When it is OH, then R 1 Yes(O)R x or –(O)(C2H5O) p R y ;

[0073] When n is 12 or 14, R 1 is -(O)S(O2)OH, R 2 is -(O)S(O2)OH, R 3 is -(O)S(O2)OH, R 4 is -(O)S(O2)OH, and R 5 When it is -(O)S(O2)OH, then R a Yes - (O)C (O)R x 、(O)R x 、-(O)C(O)OR x 、-(O)C(O)N(H)R x 、-(O)(C2H5O) p R y, -(O)P(O)(OH)2 or -(O)S(O2)OH;

[0074] In some embodiments, a compound of formula (I) or (II) is provided, wherein

[0075] R 1 Selected from the group consisting of: -OH, -(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0076] R 2 Selected from the group consisting of: -OH, -(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0077] R 3 Selected from the group consisting of: -OH, -(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0078] R 4 Selected from the group consisting of: -OH, -(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0079] R 5 Selected from the group consisting of: -OH, -(O)C(O)Rx 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0080] R a Selected from the group consisting of: -OH, -(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 and -(O)S(O2)OH;

[0081] Each R x are independently C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen;

[0082] Each R y are independently -H, C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen;

[0083] n is 2-11; and

[0084] Each p is independently selected from 1-10.

[0085] In some embodiments, the polyol lipid is a PEFA compound represented by formula (Ia) or (II-a):

[0086]

[0087] or its salts or acids,

[0088] in,

[0089] n is 6-12.

[0090] R 1

[0091] In some embodiments, R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O)p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R 1 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2 and -S(O2)OH. In some embodiments, R 1 is -H. In some embodiments, R 1 is -P(O)(OH)2 or -S(O2)OH. In some embodiments, R 1 Yes-C(O)R x In some embodiments, R 1 is -Ac. In some embodiments, R 1 Yes-R x In some embodiments, R 1 Yes - C(O)OR y In some embodiments, R 1 Yes-C(O)N(H)R y In some embodiments, R 1 Yes -(C2H5O) p R y In some embodiments, R 1 is -P(O)(OH)2. In some embodiments, R 1 is -S(O2)OH. In some embodiments, R 1 Yes-(Cj H k O m ).

[0092] R 2

[0093] In some embodiments, R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R 2 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2 and -S(O2)OH. In some embodiments, R 2 is -H. In some embodiments, R 2 is -P(O)(OH)2 or -S(O2)OH. In some embodiments, R 2 Yes-C(O)R x In some embodiments, R 2 is -Ac. In some embodiments, R 2 Yes-R x In some embodiments, R 2Yes-C(O)OR y In some embodiments, R 2 Yes -C(O)N(H)R y In some embodiments, R 2 Yes -(C2H5O) p R y In some embodiments, R 2 is -P(O)(OH)2. In some embodiments, R 2 is -S(O2)OH. In some embodiments, R 2 Yes-(C j H k O m ).

[0094] R 3

[0095] In some embodiments, R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R 3 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y, -P(O)(OH)2 and -S(O2)OH. In some embodiments, R 3 is -H. In some embodiments, R 3 is -P(O)(OH)2 or -S(O2)OH. In some embodiments, R 3 Yes-C(O)R x In some embodiments, R 3 is -Ac. In some embodiments, R 3 Yes-R x In some embodiments, R 3 Yes - C(O)OR y In some embodiments, R 3 Yes-C(O)N(H)R y In some embodiments, R 3 Yes -(C2H5O) p R y In some embodiments, R 3 is -P(O)(OH)2. In some embodiments, R 3 is -S(O2)OH. In some embodiments, R 3 Yes-(C j H k O m ).

[0096] R 4

[0097] In some embodiments, R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k Om ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R 4 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2 and -S(O2)OH. In some embodiments, R 4 is -H. In some embodiments, R 4 is -P(O)(OH)2 or -S(O2)OH. In some embodiments, R 4 Yes-C(O)R x In some embodiments, R 4 is -Ac. In some embodiments, R 4 Yes-R x In some embodiments, R 4 Yes - C(O)OR y In some embodiments, R 4 Yes-C(O)N(H)R y In some embodiments, R 4 Yes -(C2H5O) p R y In some embodiments, R 4 is -P(O)(OH)2. In some embodiments, R 4 is -S(O2)OH. In some embodiments, R 4 Yes-(C j H k O m ).

[0098] R 5

[0099] In some embodiments, R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k Om )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R 5 Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2 and -S(O2)OH. 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 Yes-C(O)R x In some embodiments, R 5 is -Ac. In some embodiments, R 5 Yes-R x In some embodiments, R 5 Yes - C(O)OR y In some embodiments, R 5 Yes-C(O)N(H)R y In some embodiments, R 5 Yes -(C2H5O) p R y In some embodiments, R 5 is -P(O)(OH)2. In some embodiments, R 5 is -S(O2)OH. In some embodiments, R 5 Yes-(C j H k O m ).

[0100] R a

[0101] In some embodiments, R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ), where -(C j H k O m ) can be in linear or cyclic form. In some embodiments, R a Selected from the group consisting of: -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2 and -S(O2)OH. In some embodiments, R a is -H. In some embodiments, R a is -P(O)(OH)2 or -S(O2)OH. In some embodiments, R a Yes-C(O)R x In some embodiments, R a is -Ac. In some embodiments, R a Yes-R x In some embodiments, R a Yes - C(O)OR y In some embodiments, R a Yes-C(O)N(H)R y In some embodiments, R aYes -(C2H5O) p R y In some embodiments, R a is -P(O)(OH)2. In some embodiments, R a is -S(O2)OH. In some embodiments, R a Yes-(C j H k O m ).

[0102] R x

[0103] In some embodiments, each R x are independently C1-C3 alkyl, wherein R x is optionally substituted with 1-7 halogen instances. x is a methyl group, where R x is optionally substituted with 1-7 halogen instances. x is ethyl, where R x is optionally substituted with 1-7 halogen instances. x is n-propyl, where R x is optionally substituted with 1-7 halogen instances. x is isopropyl, where R x is optionally substituted with 1-7 halogen instances. x In some embodiments, R x In some embodiments, R x In some embodiments, R x It is isopropyl.

[0104] R y

[0105] In some embodiments, each R y are independently -H or C1-C3 alkyl, wherein R y is optionally substituted with 1-7 halogen instances. y is -H. In some embodiments, each R y are independently C1-C3 alkyl, wherein R y is optionally substituted with 1-7 halogen instances. y is a methyl group, where R y is optionally substituted with 1-7 halogen instances. y is ethyl, where R yis optionally substituted with 1-7 halogen instances. y is n-propyl, where R y is optionally substituted with 1-7 halogen instances. y is isopropyl, where R y is optionally substituted with 1-7 halogen instances. y In some embodiments, R y In some embodiments, R y In some embodiments, R y It is isopropyl.

[0106] In some embodiments, the polyol lipid is a PEFA compound represented by:

[0107]

[0108] or a salt or an acid thereof.

[0109] Preparation of compounds

[0110] The following are examples of specific embodiments of the invention described by this disclosure. The examples provided are for illustrative purposes only and are not intended to limit the scope of the invention in any way. The groups (e.g., OR 1 , OR 2 etc.) refers to the corresponding groups described herein (e.g., R 1 , R 2 Efforts have been made to ensure accuracy with respect to numbers used (eg, amounts, temperature, etc.), but some experimental errors and deviations should, of course, be accounted for.

[0111] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 1 or 2:

[0112] Solution 1

[0113]

[0114] Where LG is a leaving group.

[0115] Solution 2

[0116]

[0117] Where LG is a leaving group.

[0118] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 3 or 4:

[0119] Solution 3

[0120]

[0121] Solution 4

[0122]

[0123] In some embodiments, compounds of the present disclosure can be prepared as outlined in Schemes 5 or 6:

[0124] Solution 5

[0125]

[0126] Solution 6

[0127]

[0128] The 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 its entirety.

[0129] Non-limiting example of preparation of hydroxy-dodecanoic acid 2,3,4,5-tetrahydroxy-6-phosphonooxy-hexyl ester:

[0130]

[0131] Non-limiting example of preparation of D-mannitol 1-phosphate: Pure D-mannitol and P2O5 are heated 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 under N2 for 4 hours as outlined in Wenyuan Han et al., Polymers 11, (2019), 1031.

[0132] Emulsifier

[0133] Emulsifiers comprising at least one polyol lipid can be used to stabilize water-in-oil emulsions. The emulsifiers described herein may include at least one polyol lipid for stabilizing oil-in-water emulsions.

[0134] 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 the components of the product or system into which it is introduced. In some embodiments, the emulsifier has no adverse effect on the product or system. In some embodiments, the emulsifier has minimal adverse effect on the product or system. In some embodiments, the emulsifier is present in the end product of the treatment 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.

[0135] In some embodiments, the emulsifier has an HLB value of 0-12 to form a water-in-oil emulsion. In some embodiments, for an oil-in-water emulsion, the emulsifier has an HLB value in the range of 6-18. In some embodiments, the emulsifier may be mixed with another emulsifier to stabilize the emulsion in the final product. In some embodiments, the additional emulsifier may include a PEFA compound; however, in other embodiments, the additional emulsifier may not include a PEFA compound.

[0136] The emulsifiers and water-in-oil emulsions disclosed herein offer advantages over other conventional agents and formulations because they are renewable, have low toxicity, and / or have good biodegradability while still maintaining emulsion stability over time or when heated, and can improve the composition of the final consumer product.

[0137] The emulsifier may include at least one polyol lipid. In some embodiments, at least one polyol lipid is a PEFA compound. The PEFA compound may include one of the PEFA compounds described herein, including those represented by formula (I), (II), (Ia) or (II-a).

[0138] In some embodiments, the emulsifier may include two or more polyol lipids. In some embodiments, the two or more polyol lipids are polyol esters of fatty acids (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).

[0139] The emulsion may be formed from oil and water components. In some embodiments, the method may 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).

[0140] Emulsifier can be provided in various forms. For example, emulsifier can be provided in dry form. In some embodiments, an effective amount of emulsifier can 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 can also depend on the type of emulsion used. In some embodiments, the effective amount added is about 2-3 times lower than the amount required for using conventional emulsifiers. For example, 5 weight % (wt%) can be provided to replace 15wt% of emulsifier to emulsify 10wt% of oil.

[0141] In some embodiments, the emulsifier may have pentitol polyol esters of fatty acids and hexitol polyol esters of fatty acids. In some embodiments, the C16 and C18 fatty acid components of the pentitol polyol esters and the hexitol polyol esters may contain about 20% to about 99% PEFA; and in some embodiments about 30% to about 95% PEFA; 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 the hexitol polyol esters may contain 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; in some embodiments, the ratio is about 50:1 or greater.

[0142] Water-in-oil emulsions and oil-in-water emulsions

[0143] The water-in-oil emulsion may 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).

[0144] In some embodiments, the water-in-oil emulsion may comprise two or more polyol lipids. In some embodiments, the oil-in-water emulsion comprises two or more polyol lipids. In some embodiments, the two or more polyol lipids are PEFAs. 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).

[0145] The water-in-oil emulsion and the oil-in-water emulsion may further comprise a solvent, a carrier, an additive, a stabilizer, a surfactant, an emulsifier, or a combination thereof.

[0146] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion may each further comprise a solvent. Such solvents may be selected to dissolve or disperse at least one polyol lipid. Suitable solvents include any one of a variety of solvents that dissolve but do not significantly degrade at least one polyol lipid.

[0147] The limiting examples of solvent include hydrocarbons (both aromatic and aliphatic), oxygenated solvents (alcohols, ketones, aldehydes, ethers, glycol ethers, esters and glycol ether esters), polyalkylene oxides, end-capped polyalkylene oxides and combinations thereof. Suitable polyalkylene oxides include polyethylene glycol, polypropylene glycol, polybutylene glycol, mixtures thereof, etc. Suitable end-capped polyalkylene oxides include monoalkyl ethers and dialkyl ethers of corresponding polyalkylene oxides, such as monomethyl ether and dimethyl ether of polyalkylene glycol, monoethyl ether and diethyl ether of polyalkylene glycol, monopropyl ether and dipropyl ether of polyalkylene glycol, monobutyl ether and dibutyl ether of polyalkylene glycol, mixtures thereof, etc. Suitable end-capped polyalkylene oxides include methyl polyethylene glycol (e.g., monomethyl ether of polyethylene glycol), dimethyl polyethylene glycol (e.g., dimethyl ether of polyethylene glycol), mixtures thereof, etc.

[0148] Suitable solvent solubilizers include glycol ethers. Suitable glycol ethers include diethylene glycol n-butyl ether, diethylene glycol n-propyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol tert-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 (which can be used as DOWANOL EPH TM Commercially available from Dow Chemical Co.), propylene glycol phenyl ether (available as DOWANOL PPH TM Commercially available from Dow Chemical Co.), etc., or mixtures thereof. Other suitable commercially available glycol ethers (all of which are available from Union Carbide Corp.) include butoxyethyl PROPASOL TM , butyl carbitol TM Acetate, Butyl CARBITOL TM , Butyl CELLOSOLVE TM Acetate, Butyl CELLOSOLVE TM, DIPROPASOL BUTYL TM , Butyl PROPASOL TM 、CARBITOL TM PM-600, CARBITOL TM Low Gravity, CELLOSOLVE TM Acetate, CELLOSOLVE TM , Ester EEP TM 、FILMER IBT TM 、HEXYL CARBITOL TM 、Hexyl CELLOSOLVE TM , Methyl CARBITOL TM , Methyl CELLOSOLVE TM Acetate, Methyl CELLOSOLVE TM 、Methyl DIPROPASOL TM , Methyl PROPASOL TM Acetate, Methyl PROPASOL TM , PROPYLENE CARBITOL TM , Propyl CELLOSOLVE TM 、Propyl DIPROPASOL TM and Propyl PROPASOL TM .

[0149] Water-in-oil emulsions and oil-in-water emulsions can each further include 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 dissolving, suspending or producing a polyol lipid and for forming an equilibrium mixture. The carrier can also be used for delivering the antimicrobial component of the emulsion composition to an object. For this reason, the carrier can include any one or more components that can promote this type of delivery and provide additional functions for the emulsion composition.

[0150] In certain embodiments, the carrier mainly includes water, which can promote solubility and serve as a medium for reaction and equilibrium. Non-limiting examples of carriers can include one or more hydrocarbon oils, water, fatty alcohols and esters, and organic solvents, such as simple alkyl alcohols, for example ethanol, isopropanol, n-propanol, etc.

[0151] In certain embodiments, the carrier constitutes the majority of the water-in-oil emulsion or the oil-in-water emulsion. The carrier concentration and type will depend on the nature of the formulation, environmental storage and application method, including factors such as the concentration of the polyol lipid.

[0152] 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 50 wt % carrier, about 10 wt % to about 20 wt % carrier, about 15 wt % to about 70 wt % carrier, about 15 wt % to about 80 wt % carrier, about 20 wt % to about 70 wt % carrier, about 20 wt % to about 50 wt % carrier, about 20 wt % to about 40 wt % carrier, about 20 wt % to about 30 wt % carrier, about 30 wt % to about 75 wt % carrier, about 30 wt % to about 70 wt % carrier, about 40 wt % to about 99.99 wt % carrier, about 40 wt % to about 90 wt % carrier, or about 60 wt % to about 70 wt % carrier.

[0153] In certain embodiments, the oil-in-water emulsion comprises from about 0% to about 98% by weight of a carrier, from about 0.001% to about 99.99% by weight of a carrier, from about 0.2% to about 60% by weight of a carrier, from about 1% to about 98% by weight of a carrier, from about 5% to about 99.99% by weight of a carrier, from about 5% to about 97% by weight of a carrier, from about 5% to about 90% by weight of a carrier, from about 5% to about 70% by weight of a carrier, from about 5% to about 20% by weight of a carrier, from about 10% to about 90% by weight of a carrier, from about 10% to about 80% by weight of a carrier, from about 10% to about 50 wt % carrier, about 10 wt % to about 20 wt % carrier, about 15 wt % to about 70 wt % carrier, about 15 wt % to about 80 wt % carrier, about 20 wt % to about 70 wt % carrier, about 20 wt % to about 50 wt % carrier, about 20 wt % to about 40 wt % carrier, about 20 wt % to about 30 wt % carrier, about 30 wt % to about 75 wt % carrier, about 30 wt % to about 70 wt % carrier, about 40 wt % to about 99.99 wt % carrier, about 40 wt % to about 90 wt % carrier, or about 60 wt % to about 70 wt % carrier.

[0154] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion may each further include one or more additives. Non-limiting examples of additives include ethylene oxide / propylene oxide block copolymers, butylene oxide / propylene oxide block copolymers, ethylene oxide / butylene oxide block copolymers, waxes or silicone-based materials.

[0155] In some embodiments, the water-in-oil emulsion and the oil-in-water emulsion may each further include a stabilizer. The shelf life of the water-in-oil emulsion or the oil-in-water emulsion as 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, butanol, and formaldehyde.

[0156] In some embodiments, a surfactant or co-emulsifier is selected to be added to a water-in-oil emulsion or an oil-in-water emulsion to improve the wettability of the emulsion. For example, when such an emulsion is applied to a food material, or when such an emulsion is formed with at least one polyol lipid, improved wettability is useful. In some embodiments, such a surfactant or co-emulsifier can be anionic, cationic, nonionic or amphoteric surfactants and combinations thereof. Non-limiting examples of anionic surfactants or co-emulsifiers include alkali metals, ammonium and amine soaps; The fatty acid moiety of such soaps preferably contains at least 16 carbon atoms. Other non-limiting examples of anionic surfactants or co-emulsifiers include alkali metal salts of alkyl-aryl sulfonic acids, dialkyl sodium sulfosuccinates, sulfated or sulfonated oils, such as sulfated castor oil; Alkali metal salts of sulfonated tallow and short-chain petroleum sulfonic acids. Non-limiting examples of cationic surfactants or co-emulsifiers include salts of long chain primary, secondary or tertiary amines, such as oleamide acetate, cetylamine acetate, didodecylamine lactate, aminoethyl-aminoethylstearamide acetate, dilauroyltriethylenetetramine diacetate, 1-aminoethyl-2-heptadecenylimidazoline acetate; and quaternary salts, such as cetylpyridinium bromide, cetylethylmorpholine chloride and diethylbehenylammonium chloride. Non-limiting examples of nonionic surfactants or co-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 having 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, triethylene glycol monoarachidate, tridecyl glycol monobehenate, tridecyl glycol dibehenate; polyol partial higher fatty acid esters, such as sorbitan tristearate; Fatty acid esters; ethylene oxide condensation products of higher fatty acid esters of polyol parts and their internal anhydrides (mannitol-anhydride, called mannan, and sorbitol-anhydride, called sorbitan), such as glycerol monopalmitate reacted with 10 molecules of ethylene oxide, pentaerythritol monooleate reacted with 12 molecules of ethylene oxide, sorbitan monostearate reacted with 10-15 molecules of ethylene oxide, and mannan monopalmitate reacted with 10-15 molecules of ethylene oxide; long-chain polyethylene glycol, in which one hydroxyl group is esterified with a higher fatty acid and the other hydroxyl group is etherified with a low molecular alcohol, such as methoxy polyethylene glycol 550 monostearate (550 refers to the average molecular weight of the polyethylene glycol ether).Non-limiting examples of amphoteric surfactants include alkyl betaines, alkyl dimethylamine N-oxides, alkyl amidopropylamine N-oxides, alkyl amidopropyl betaines, cocoamidopropyl betaines, cocoamphoacetates and cocoamphodiacetates, phosphatidylserine, phosphatidylethanolamine phosphatidylcholine, sphingolipids, lauryl dimethylamine oxide, and myristic amine oxide. In some embodiments, a combination of two or more of these surfactants may be used; for example, a cation may be blended with a nonionic or an anion may be blended with a nonionic.

[0157] Those of ordinary skill in the art will appreciate that the individual components of a water-in-oil emulsion or an oil-in-water emulsion may vary depending on the physical and chemical qualities required for emulsion stability in a given process and / or the application to which the formulation will be applied. For example, the dispersibility of a water-in-oil emulsion or an oil-in-water emulsion in water may be adjusted as needed to obtain the desired properties.

[0158] The hydrophilic-lipophilic balance (HLB) of an emulsion is a measure of its hydrophilic or lipophilic degree. HLB values ​​are calculated using known methods. In some embodiments, the water-in-oil emulsions disclosed herein have an HLB of 0 to 12. In some embodiments, the water-in-oil emulsions disclosed herein have an HLB of less than 10. In some embodiments, the water-in-oil emulsions disclosed herein are fat-soluble (water-insoluble). In some embodiments, the water-in-oil emulsions disclosed herein have an HLB of 4 to 10. In some embodiments, the water-in-oil emulsions disclosed herein have an HLB of 6 to 8. In some embodiments, the water-in-oil emulsions disclosed herein have an HLB of 3 to 6.

[0159] In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6 to 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 lipid soluble (water insoluble). In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6 to 12. In some embodiments, the oil-in-water emulsions disclosed herein have an HLB of 6 to 8. In some embodiments, the polyol lipid has an HLB of less than 12.

[0160] As described herein, the emulsifier may be formed from a polyol lipid with a PEFA compound. As a primary emulsifier, the described emulsifier may provide a reduction in interfacial tension to obtain a smaller droplet size. This allows the emulsifier to provide effective steric stability after forming a W / O or O / W emulsion. As a primary emulsifier or the only emulsifier, the described emulsifier may have an HLB value of about 8 to about 10 in certain embodiments; and an HLB value of about 9 in certain embodiments.

[0161] The emulsifiers described herein can also be used as a co-emulsifier with another PEFA-based emulsifier or a non-PEFA-based emulsifier. In certain embodiments, the PEFA-based emulsifier provides enhanced benefits for emulsification when the PEFA-based emulsifier is mixed with another emulsifier having a similar HLB value. For example, in certain embodiments, each co-emulsifier has an HLB value of about 6 to about 12; in certain embodiments, the HLB value is about 8 to about 10; and in certain embodiments, the HLB value is about 9. Applications

[0162] The emulsifiers and related compositions described herein are particularly relevant to food and beverage applications, as well as cosmetic and dermatological applications, home care, personal care, industrial cleaning, automotive care, oil cracking, pharmaceuticals, agriculture (e.g., pesticides), paints, adhesives, sealants, coatings, inks, flavors and fragrances.

[0163] Food / Beverages

[0164] The methods and processes described herein effectively allow immiscible substances (such as oil and water) to be uniformly mixed and produce stable emulsions, compared to similar methods or processes in which the polyol fatty acid esters (PEFA) described herein are not used, which have longer shelf life and improved preservation against yeast and mold in the manufacture of various substances (such as food materials). An important consideration in food production is that the emulsifier used should not impart an off-flavor or other negative characteristic to the food product. Without being limited by theory, it is expected that the methods and processes of the present disclosure have the following characteristics: (1) provide a stable emulsion and / or (2) provide a neutral taste to the final food product.

[0165] In some embodiments, an emulsifier comprising a PEFA compound as described herein may be added to a food material in sufficient amounts to achieve the level of stable emulsion required for the method. It should be recognized that different food processing techniques require different amounts of emulsifiers to achieve the desired results. In some embodiments, the amount of emulsifier added to the food material is measured as a percentage of the combined weight of the emulsifier and the food material (the total weight of the food composition). In some embodiments, the amount of the emulsifier is about 0.001% to 0.5% by weight of the total weight of the food composition, or about 0.01% to 5% by weight of the total weight of the food composition. In some embodiments, the amount of the emulsifier is about 0.1% to 1% by weight of the total weight of the food composition. In some embodiments, the amount of the emulsifier is about 0.01% to 2% by weight of the total weight of the food composition, or about 0.01% to about 1% by weight of the total weight of the food composition.

[0166] Non-limiting examples of foodstuffs for which a stable emulsion is desired include beverages (such as flavored carbonated or non-carbonated soft drinks), dairy-based beverages, soy beverages, teas, juice drinks, flavored juices, sports drinks (e.g., ), alcoholic beverages; and non-beverage foods such as baked goods, syrups, flavored oil emulsions, salad dressings, mayonnaise, dairy products, ice cream, various types of pies, candies, jams and jellies. For example, emulsifiers can be used to stabilize flavored emulsions in beverages such as carbonated soft drinks. Emulsifiers can also be used to form other beverages.

[0167] Other non-limiting examples of foodstuffs requiring stable emulsions include beverages in the form of ready-to-dissolve powder mixes, and liquid concentrates that require reconstitution with other liquids such as milk, water, and juice prior to consumption.

[0168] Non-limiting examples of methods of using foodstuffs where a stable emulsion is desired include food processing, such as rheology modifiers in food applications including doughs, batters.

[0169] Non-limiting examples of methods of using foodstuffs where a stable emulsion is desired include during the industrial processing of sugar beets (such as resulting in the formation of sugars, syrups, and juices), during washing, cutting, diffusion, carbonization, and evaporation steps in processing equipment; during the industrial processing of potatoes, during washing, cleaning, polishing, and cutting in processing equipment; and industrial fermentation processes, including fermentation.

[0170] Additional non-limiting examples of processes include food processing such as cleaners for fresh and frozen fruits, vegetables, meats and processed foods, food processing such as rheology modifiers in food applications including doughs, batters, and food processing such as anti-sticking agents.

[0171] In some embodiments, a food composition or beverage disclosed here does not contain petroleum-based surfactants.

[0172] In some embodiments, the food compositions or beverages disclosed herein may have one or more improved properties compared to food compositions or beverages comprising conventional emulsifiers. In some embodiments, one or more improved properties may be selected from the group consisting of increased solubility, improved emulsifying ability, increased stability of emulsified particles, increased stability of emulsified particle size, increased viscosity stability, or improved feel and / or sensation during use.

[0173] In some embodiments, the food material comprises an emulsifier disclosed herein and / or a water-in-oil emulsion disclosed herein and / or an oil-in-water emulsion disclosed herein, wherein the amount of the emulsifier and / or the water-in-oil emulsion and / or the oil-in-water emulsion is sufficient to achieve the emulsion stability over time and the emulsion stability when heated required for the process. It should be recognized that different food processing techniques result in different levels of emulsion stability and therefore require different amounts of emulsifiers and / or water-in-oil emulsions and / or oil-in-water emulsions to achieve the desired results.

[0174] Cosmetics / Dermatology

[0175] Due to the skin-friendly properties, the polyol lipids disclosed herein can be used in cosmetic and dermatological compositions. Possible application forms of cosmetic and dermatological compositions comprising at least one polyol lipid may include sprays, lotions, creams, ointments, and thus be used in a very wide range of consistencies from water-thin to severe pastes or solids.

[0176] 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.

[0177] Further non-limiting examples of cosmetic and dermatological compositions include care creams and lotions for the face, body and hands, sunscreen lotions, make-up, aerosols, roll-ons, pump sprays, sticks such as in the antiperspirant / deodorant field, baby care products, intimate care products, foot care products, hair care products, nail care products, tooth care products or oral care products, and dermatological ointments.

[0178] In some embodiments, cosmetic and dermatological compositions may include polyol lipids. Such polyol lipids may also include one or more cosmetic active ingredients. Non-limiting examples of cosmetic or biologically active ingredients include phytosphingosine (and phytosphingosine derivatives), sphingosine (and sphingosine derivatives), sphingolipids, tocopherol, tocopheryl acetate, tocopheryl palmitate, ascorbic acid, polyphenols, deoxyribonucleic acid, coenzyme Q10, retinol, AHA acid, amino acids, hyaluronic acid, alpha-hydroxy acids, flavonoids, isoflavones, stilbenes, catechins, polyglutamic acid, 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, beta-glucan, santalic acid, and vitamin complexes.

[0179] In some embodiments, the cosmetic or dermatological compositions disclosed herein do not include petroleum-based surfactants.

[0180] 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 consisting of increased solubility, improved emulsification ability, increased stability of emulsified particles, increased stability of emulsified particle size, increased viscosity stability, or improved feel and / or sensation during use.

[0181] 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, wherein the amount of the emulsifier and / or the water-in-oil emulsion and / or the oil-in-water emulsion is sufficient to achieve the emulsion stability over time and the emulsion stability when heated required for the process. It should be recognized that different cosmetic or dermatological compositions require different levels of emulsion stability and therefore require different amounts of emulsifiers and / or water-in-oil emulsions and / or oil-in-water emulsions to achieve the desired results.

[0182] In some embodiments, the cosmetic or dermatological 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 increased solubility, improved emulsion capacity, increased stability of emulsified particles, increased stability of emulsified particle size, improved wettability, improved suspension, increased viscosity stability, and improved tactile sensation and / or sensation during use (e.g., improved tactile sensation, improved feeling of use, sustainable suppression of oiliness, maintenance of moisturizing properties after application, and no stickiness). Example

[0183] The following are examples of specific embodiments for implementing the present invention. The examples provided are 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 the accuracy of the numbers used (e.g., amounts, temperatures, etc.), but of course some experimental errors and deviations should be considered.

[0184] When identifying an effective emulsifier for cosmetic or dermatological applications, wetting or dispersant characteristics may be important. For example, dispersant characteristics can ensure the stability of the composition throughout the manufacturing, storage and application processes. Such emulsifiers can properly "wet" solid particles by properly replacing the air around the particles, thereby preventing undesirable agglomeration to effectively and evenly disperse the particles in the solution. When evaluating such wetting or dispersant properties compared to other known W / O emulsion compositions, the emulsifiers described herein provide improved performance. For example, sorbitan sesquioleate (e.g., SPAN TM 83) are well-known and used W / O emulsion compositions for personal care compositions such as those used in cosmetic or dermatological applications. Figure 1 As shown in FIG. 1 , the vial on the left (vial 1) contains 20% ZnO particles added to the emulsifier A of the present invention, and the vial on the right (vial 2) contains ZnO particles suspended in SPAN. TM 83 of 20% ZnO particles. Figure 1 The time period just after the vial was stirred is shown, and the two vials show the emulsion system in which the ZnO particles are suspended. Figure 2 These same two vials are shown after 1 week, where the vials had been stored at 60°C. It can be seen that the ZnO particles remain suspended in vial 1 containing the inventive emulsifier A, however, the ZnO particles have settled to the bottom of vial 2 containing the well-known emulsion composition, indicating phase separation and instability. These results show that the inventive emulsifier A performs better than SPAN TM 83.

[0185] Furthermore, this result illustrates the improved stability of the inventive emulsifier A, as the color of vial 1 remained white after 1 week, while the composition in vial 2 had darkened and had a yellowish or brown coloration. Stability is an important feature of compositions used in personal care compositions and food raw material compositions, namely in relation to the shelf life of the product and the uniform dispersion of active substances. Therefore, the inventive emulsifier A is expected to provide improved shelf life and better sun protection factor (SPF) delivery for any emulsion composition and related products seeking such benefits.

[0186] Tables 1-7 provide a sampling of the breadth of applications in which the inventive emulsions described herein can be used. As described herein, the emulsifiers and related compositions described herein are relevant to a wide variety of industries and can be used in lotions, skin creams, conditioners, facial and surface cleansers, and other compositions.

[0187] The emulsions of the present invention described herein can help provide stability of the emulsion composition as well as other benefits. For example, Table 1 shows the formulation of a lotion emulsion composition comprising Emulsifier B of the present invention. Emulsifier B of the present invention can reduce interfacial tension to allow for small droplet sizes. In addition, Emulsifier B of the present invention can create a spatial barrier around the droplets and combine with xanthan gum to provide stability of the emulsion composition under extended room temperature and high temperature conditions. Specifically, using Emulsifier B of the present invention, it was found that the lotion emulsion composition was stable for four weeks at room temperature, 40°C and 45°C.

[0188] Table 1. Lotion formulations

[0189]

[0190]

[0191] To prepare the lotion of Table 1, water was heated to 75°C. Separately, Emulsifier B of the present invention and an emollient were mixed and then heated to 75°C. Next, the humectant, thickener, and preservative were mixed together and added to the water while stirring with an impeller. The mixture of Emulsifier B of the present invention and the emollient was then added to the remaining components while continuing to stir and mix without heating. The components were homogenized until glossy.

[0192] Table 2 shows the formulation of another lotion emulsion composition including the emulsifier C of the present invention.

[0193] Table 2. Lotion formulations

[0194] Components weight% water 84.81 glycerin 3 Sodium Benzoate 0.5 Isopropyl Palmitate 2 Cetyl Alcohol 2 beeswax 1 Almond Oil 4 Citric acid 0.2 Fragrance 0.5 Required emulsifier 0 Tween 80 0.91 Emulsifier C of the present invention 1.08

[0195] Table 3 shows the formulation of a skin care cream emulsion composition comprising the emulsifier D of the present invention.

[0196] Table 3. Formulation of skin cream

[0197]

[0198]

[0199] Table 4 shows the formulation of a rinse-off hair conditioner emulsion composition including the emulsifier E of the present invention.

[0200] Table 4. Conditioner formulations

[0201] Components weight% water 79.93 Quaternary ammonium surfactants 5.2 glycerin 3.1 Guar Gum 0.52 Citric acid 0.05 Coconut Oil 6 Cetyl Alcohol 2.1 Fragrance 0.1 Tween 80 1.1 Emulsifier E of the present invention 1.9

[0202] Table 5 shows the formulation of a leave-in hair conditioner emulsion composition including the emulsifier F of the present invention.

[0203] Table 5. Conditioner formulations

[0204]

[0205]

[0206] Table 6 shows the formulation of a surface cleaner emulsion composition including Emulsifier G of the present invention.

[0207] Table 6. Formulation of surface cleaner emulsion

[0208] Components weight% water 97.2 Sodium lauryl sulfate 0.8 Tetrasodium Glutamate Diacetate 0.2 Sodium citrate dihydrate 0.95 Preservatives (MBS) 0.3 Citric acid 0.1 Fragrance 0.25 Emulsifier G of the present invention 0.2

[0209] Table 7 shows the formulation of a makeup remover emulsion composition including the emulsifier H of the present invention.

[0210] Table 7. Makeup remover formula

[0211] Components weight% Isopropyl myristate 80.9 Coconut Oil 4 olive oil 4 Alkyl polyglycosides 0.2 Fragrance 0.1 Tween 80 4 Caprylyl glycol 0.8 Citric acid QS Emulsifier H of the present invention 6

[0212] Emulsifier evaluation

[0213] HLD parameters are determined using methods known in the art (e.g., hybrid methods). And as described above, HLB measurements are also determined according to methods known in the art (e.g., the calculation Davies and Lin group contribution method according to Kothencz et al. (2017) Studia Universitatis Babes-bolyai Chemia 62: 451-458).

[0214] Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein.The scope of the invention is not limited to the above description, but rather is set forth in the appended claims.

[0215] In the claims, articles such as "a", "an", and "the" may refer to one or more than one, unless indicated to the contrary or obvious from the context. Claims or descriptions including "or" between one or more members of a group are considered satisfactory unless indicated to the contrary or obvious from the context, unless one or all of the group members are present, used in, or otherwise relevant to a given product or process. The invention includes embodiments in which exactly one member of the group is present, used in, or otherwise relevant to a given product or process. The invention includes embodiments in which more than one or all of the group members are present, used in, or otherwise relevant to a given product or process.

[0216] It should also be noted that the term "comprising" is intended to be open ended, and allows but does not require the inclusion of additional elements or steps. When the term "comprising" is used herein, the term "consisting of" is also thereby encompassed and disclosed.

[0217] When a range is given, the endpoints are included. In addition, it should be understood that unless otherwise indicated or otherwise obvious from the context and understanding of one of ordinary skill in the art, the values ​​expressed as ranges may assume any specific value or sub-range within the range in different embodiments of the present invention, unless the context clearly indicates otherwise, otherwise expressed as one-tenth of the unit of the lower limit of the range.

[0218] All cited sources (e.g., references, publications, databases, database entries, and techniques cited herein) are incorporated herein by reference, even if not explicitly stated in the citation. In the event of a conflict between a cited source and the language of the present application, the language in the present application shall prevail.

[0219] Section and table headings are not limiting.

[0220] It is to be understood that the words used are words of description rather than limitation and that changes may be made within the purview of the appended claims without departing from the true scope and spirit of the invention in its broader aspects.

[0221] While the present invention has been described at some length and with a certain particularity with respect to several described embodiments, it is not intended to be limited to any such particularity or embodiment or to any particular embodiment, but rather should be interpreted with reference to the appended claims so as to provide the broadest possible interpretation of such claims in light of the prior art and thereby effectively encompass the intended scope of the present invention.

[0222] All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety. In the event of a conflict, the present specification (including definitions) shall prevail. In addition, section headings, materials, methods, and examples are illustrative only and not restrictive.

Claims

1. An emulsifier comprising one or more polyol lipids, wherein the one or more polyol lipids are selected from polyol fatty acid esters (PEFA) compounds represented by formula (I) or (II): or its salts or acids, in, R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H 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)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); Each R x are independently C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen; Each R y are independently -H or C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen; n is 2-20; j is 2-12; k is 4-26; m is 1-16; and Each p is independently selected from 1-10.

2. An emulsifier comprising one or more polyol lipids, wherein the one or more polyol lipids are selected from: a) PEFA compounds of formula (I) or (II): or its salts or acids, in, R 1 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -COOH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 2 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 3 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); R 4 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m )); R 5 Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m )1); R a Selected from the group consisting of: -H, -C(O)R x , -R x 、-C(O)OR y 、-C(O)N(H)R y 、-(C2H5O) p R y , -P(O)(OH)2, -S(O2)OH, -NO2, -NH2, -(C j H k O m )、-OH、-(O)C(O)R x 、-(O)R x 、-(O)C(O)OR y 、-(O)C(O)N(H)R y 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2, -(O)S(O2)OH, -(O)NO2, -(O)NH2 and -(O)(C j H k O m ); Each R x are independently C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen; Each R y are independently -H, C1-C3 alkyl, wherein R x optionally substituted with 1-7 instances of halogen; n is 2-20; j is 2-12; k is 4-26; m is 1-16; and Each p is independently selected from 1-10, in, When n is 12 or 14 and R 1 When it is -OH or -(O)Ac, then R a Not -(O)Ac or -(O)Me; When n is 12 and R a When it is -OH, then R 2 Not -OH or; When n is 12 or 14, R a Yes -OH, R 2 Yes OH, R 3 is OH, and R 4 When it is OH, then R 1 Yes(O)R x or –(O)(C2H5O) p R y ; When n is 12 or 14, R 1 is -(O)S(O2)OH, R 2 is -(O)S(O2)OH, R 3 is -(O)S(O2)OH, R 4 is -(O)S(O2)OH, and R 5 When it is -(O)S(O2)OH, then R a Yes-(O)C(O)R x , R x 、-(O)C(O)OR x 、-(O)C(O)N(H)R x 、-(O)(C2H5O) p R y , -(O)P(O)(OH)2 or -(O)S(O2)OH; b) A group consisting of: acetylated C12:0-3-hydroxy fatty acid esterified to D-arabitol by 3 acetylations, acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol by 4 acetylations, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol by 2 acetylations, acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol by 2 acetylations, acetylated C14:0-3-hydroxy fatty acid esterified to D-arabitol by 4 acetylations, acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol by 5 acetylations. Acetylated C14:0-3-hydroxy fatty acid esterified to D-mannitol by acetylation for 3 times, acetylated C16:0-3-hydroxy fatty acid esterified to D-arabitol by acetylation for 3 times, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol by acetylation for 4 times, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol by acetylation for 2 times, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol by acetylation for 5 times fatty acid, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol by 4 acetylations, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol by 2 acetylations, acetylated C16:0-3-hydroxy fatty acid esterified to D-mannitol by 5 acetylations, acetylated C16:0-3-hydroxy fatty acid esterified to D-arabinitol by 4 acetylations, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol by 3 acetylations, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol by 4 acetylations acetylated C18:0-3-hydroxy fatty acid, acetylated C18:0-3-hydroxy fatty acid esterified to D-arabitol by 3 acetylations, acetylated C18:0-3-hydroxy fatty acid esterified to D-mannitol by 5 acetylations, acetylated C18:0-3-hydroxy fatty acid esterified to D-arabitol by 4 acetylations, acetylated C20:0-3-hydroxy fatty acid esterified to D-mannitol by 3 acetylations, acetylated C20:0-3-hydroxy fatty acid esterified to D-mannitol by 4 acetylations; or c) A group consisting of: or its salts or acids.

3. The emulsifier according to any one of claims 1 or 2, wherein the emulsifier comprises two or more of the polyol lipids.

4. The emulsifier according to claim 1 or 2, wherein the PEFA compound has an n value of 4 to 20.

5. The emulsifier of claim 1 or 2, wherein the one or more polyol lipids comprise pentitol polyol esters, hexitol polyol esters, or a combination thereof.

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

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

8. The emulsifier of claim 5, wherein the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can contain from about 20% to about 99% of the PEFA compounds.

9. The emulsifier of claim 5, wherein the C16 and C18 fatty acid components of the pentitol polyol esters and hexitol polyol esters can contain from about 30% to about 95% of the PEFA compounds.

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

11. The emulsifier of claims 1 to 10, wherein the compound is further represented by formula (Ia) or (II-a): or its salts or acids, in, n is 6-12.

12. A personal care composition comprising the emulsifier according to claim 1 or 2.

13. The personal care composition of claim 10, which is a cosmetic or dermatological composition.

14. A food raw material composition comprising the emulsifier according to claim 1 or 2.

15. A water-in-oil emulsion composition comprising the emulsifier according to claim 1 or 2.

16. The water-in-oil emulsion composition of claim 15, wherein the emulsifier is a primary emulsifier.

17. The water-in-oil emulsion composition of claim 16, further comprising a secondary emulsifier, wherein the secondary emulsifier is a non-PEFA emulsifier; and wherein the primary emulsifier and the secondary emulsifier have similar HLB values.

18. The water-in-oil emulsion composition of claim 17, wherein the HLB value of the primary emulsifier and the secondary emulsifier is in the range of about 4 to about 18.

19. An oil-in-water emulsion composition comprising the emulsifier according to claim 1 or 2.

20. The oil-in-water emulsion composition of claim 19, wherein the emulsifier is a primary emulsifier.

21. The oil-in-water emulsion composition of claim 20, further comprising a secondary emulsifier, wherein the secondary emulsifier is a non-PEFA emulsifier; and wherein the primary emulsifier and the secondary emulsifier have similar HLB values.

22. The oil-in-water emulsion composition of claim 21, wherein the HLB value of the primary emulsifier and the secondary emulsifier is in the range of about 6 to about 12.

23. The water-in-oil emulsion composition of claim 15, wherein the composition comprises two or more polyol lipids.

24. The oil-in-water emulsion composition of claim 18, wherein the composition comprises two or more polyol lipids.

25. A cosmetic or dermatological composition comprising the emulsifier of claim 1 or 2, wherein the at least one polyol lipid comprises an HLB value of less than 12.

26. The cosmetic or dermatological composition according to claim 25, which is in the form of a water-in-oil emulsion or an oil-in-water emulsion.

27. The cosmetic or dermatological composition of claim 25, which does not contain petroleum-based surfactants.

28. A food composition comprising a food material and the emulsifier according to claim 1 or 2.

29. food compositions as claimed in claim 28, it comprises two or more polyol lipids.

30. A beverage comprising the emulsifier according to claim 1 or 2.

31. The beverage of claim 30, wherein the emulsifier comprises two or more polyol lipids.

32. An agricultural composition comprising the emulsifier according to claim 1 or 2.

33. The agricultural composition of claim 32, comprising two or more polyol lipids.

34. A paint composition comprising the emulsifier according to claim 1 or 2.

35. A paint composition as claimed in claim 34 comprising two or more polyol lipids.

36. A coating composition comprising the emulsifier according to claim 1 or 2.

37. The coating composition of claim 36 comprising two or more polyol lipids.

38. An adhesive composition comprising the emulsifier according to claim 1 or 2.

39. The adhesive composition of claim 38 comprising two or more polyol lipids.

40. A sealant composition comprising the emulsifier of claim 1 or 2.

41. The sealant composition of claim 40 comprising two or more polyol lipids.

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