Coating composition comprising a core surfactant

Abstract

The present disclosure relates to a composition comprising a monoglyceride and a co-surfactant. Exemplary embodiments include from about 40% to about 99% by weight of one or more monoglycerides of C4-C28 fatty acids, from about 0.1% to about 20% by weight of one or more salts of C4-C28 fatty acids, and from about 0.1% to about 20% by weight of one or more zwitterions.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of priority to U.S. Application No. 63 / 401,934, filed on August 29, 2022, the contents of which are incorporated by reference into this application. Technical Field

[0003] The present disclosure relates to coating of agricultural products. Background Art

[0004] Agricultural products in general are susceptible to degradation and decomposition (i.e., corruption) when exposed to the environment. The agricultural products may include, for example, eggs, fruits, vegetables, produce, seeds, nuts, flowers, and / or whole plants (including processed and semi-processed forms thereof). Non-agricultural products (e.g., vitamins, candies, etc.) are also susceptible to degradation when exposed to the surrounding environment. Agricultural products may degrade via abiotic means due to loss of water from the outer surface to the atmosphere by evaporation and / or oxidation by oxygen diffused from the environment into the interior of the agricultural product and / or mechanical damage to the surface and / or light-induced degradation (i.e., photodegradation). In addition, biological stressors such as bacteria, fungi, viruses, and / or pests may also infect and decompose the agricultural products.

[0005] Common methods used to prevent degradation, maintain quality and increase the life of agricultural products include refrigeration and / or special packaging. Refrigeration requires capital-intensive equipment, requires fixed energy consumption, and if not carefully controlled, it will cause product damage or quality loss, and must be handled actively. In addition, the benefits of refrigeration are lost when the temperature-controlled supply chain is disturbed. Special packaging also requires expensive equipment, consumes packaging materials, increases transportation costs, and requires active management. Although the effects can be achieved through refrigeration and special packaging, the handling and transportation of agricultural products can cause surface wear or damage, which gives consumers a negative aesthetic perception and becomes a location for bacterial and fungal invasion. In addition, the costs associated with these methods can be added to the cost of agricultural products. Summary of the invention

[0006] The present application provides a composition comprising one or more C 4– C 28 Monoglycerides of fatty acids (total content of about 40% to about 99% by weight of the composition), one or more C 4– C 28 Salts of fatty acids (total level 0.1% to about 20% by weight of the composition) and one or more zwitterions (total level 0.1% to about 20% by weight of the composition).

[0007] The present application also provides a composition comprising one or more C 4– C 28 Monoglycerides of fatty acids, one or more C 4– C 28 The ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:1.

[0008] The present application also provides a mixture of the composition described in the present application and a solvent.

[0009] The present application also provides a coated agricultural product, which comprises an agricultural product and a layer disposed on the surface of the agricultural product, wherein the layer comprises the composition described in the present application.

[0010] The present invention also provides a method for coating agricultural products, the method comprising contacting the surface of the agricultural products with a mixture comprising a coating material and a solvent, and removing at least a portion of the solvent to form a coating on the surface of the agricultural products. The coating material comprises one or more C 4– C 28 Monoglycerides of fatty acids, one or more C 4– C 28 The ratio of the total number of moles of the one or more monoglycerides present in the coating material to the total number of moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:1.

[0011] The present application also provides a method for coating agricultural products, which comprises contacting the surface of the agricultural products with the mixture described in the present application, and removing at least a portion of the solvent to form a coating on the surface of the agricultural products.

[0012] While the disclosed inventive concept includes the inventive concept defined in the appended claims, it is to be understood that the inventive concept can also be defined in terms of the following embodiments.

[0013] In addition to the embodiments of the appended claims and the embodiments described above, the following numbered embodiments are also inventive.

[0014] Embodiment 1 is a composition comprising:

[0015] One or more C 4 -C 28 monoglycerides of fatty acids present in a total amount of from about 40% to about 99% by weight of the composition;

[0016] One or more C 4 -C 28Salts of fatty acids present in a total amount of from about 0.1% to about 20% by weight of the composition; and

[0017] One or more zwitterions are present in a total amount of 0.1% to about 20% by weight of the composition.

[0018] Embodiment 2 is the composition of embodiment 1, wherein the total content of the one or more monoglycerides is from about 70 weight percent to about 99 weight percent.

[0019] Embodiment 3 is the composition of embodiment 1, wherein the total content of the one or more monoglycerides is from about 80 weight percent to about 98 weight percent.

[0020] Embodiment 4 is the composition of any one of embodiments 1-3, wherein the total content of the one or more salts is from about 1% to about 10% by weight of the composition.

[0021] Embodiment 5 is the composition of any one of embodiments 1-3, wherein the total content of the one or more salts is from about 2% to about 10% by weight of the composition.

[0022] Embodiment 6 is the composition of any one of embodiments 1-5, wherein the total content of the one or more zwitterions is from about 1% to about 10% by weight of the composition.

[0023] Embodiment 7 is the composition of any one of embodiments 1-5, wherein the total content of the one or more zwitterions is from about 2% to about 10% by weight of the composition.

[0024] Embodiment 8 is the composition of any one of embodiments 1-7, further comprising an inorganic salt.

[0025] Embodiment 9 is the composition of embodiment 8, wherein the one or more inorganic salts comprises sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any combination thereof.

[0026] Embodiment 10 is a composition comprising:

[0027] One or more C 4 –C 28 Monoglycerides of fatty acids;

[0028] One or more C 4 –C 28 Salts of fatty acids; and

[0029] one or more zwitterions;

[0030] wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:1.

[0031] Embodiment 11 is the composition of embodiment 10, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and one or more zwitterions is from about 100:1 to about 6:1.

[0032] Embodiment 12 is the composition of embodiment 10, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and one or more zwitterions is from about 50:1 to about 8:1.

[0033] Embodiment 13 is the composition of any one of embodiments 10-12, wherein the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 10:1 to about 1:10.

[0034] Embodiment 14 is the composition of any one of embodiments 10-12, wherein the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 1:1 to about 1:10.

[0035] Embodiment 15 is the composition of any one of embodiments 10-14, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions comprise at least about 80 wt % of the composition.

[0036] Embodiment 16 is the composition of any one of embodiments 1-15, wherein the composition comprises lecithin or hydrolyzed lecithin containing at least one of the zwitterions.

[0037] Embodiment 17 is the composition of any one of embodiments 1-16, wherein at least one of the zwitterions comprises:

[0038] Positively charged groups, including quaternary ammonium groups or phosphonium groups; and

[0039] Negatively charged groups include phosphate groups, sulfonate groups or carboxylate groups.

[0040] Embodiment 18 is the composition of any one of embodiments 1-16, wherein at least one of the zwitterions comprises betaine, phosphatidylcholine, lysophosphatidylcholine, hydroxysulfobetaine, or amphoacetate.

[0041] Embodiment 19 is the composition of any one of embodiments 1-18, wherein at least one of the zwitterions comprises a compound of formula III-i or formula III-ii:

[0042]

[0043] in:

[0044] R B1 , R B2 and R B3 Each independently selected from C 1 –C 22 Alkyl and (C 1 –C 6 Alkyl)-NR B4 C(O)R H ;

[0045] Each occurrence of R B4 are independently H or C 1 –C 6 alkyl; and

[0046] Each occurrence of R H Independently for C 3 –C 21 Sidechain.

[0047] Embodiment 20 is the composition of embodiment 19, wherein R B1 and R B2 Each is C 1 -C 6 alkyl.

[0048] Embodiment 21 is the composition of embodiment 19 or embodiment 20, wherein R B3 C 10 -C 20 alkyl.

[0049] Embodiment 22 is the composition of any one of embodiments 1-21, wherein at least one of the zwitterions comprises a compound of Formula IIIA-i or Formula IIIA-ii:

[0050]

[0051] in:

[0052] R B1 and R B2 Each independently selected from C 1 –C 6 alkyl;

[0053] R B4 H or C 1 –C 6 alkyl; and

[0054] R H C 3 –C 21Sidechain.

[0055] Embodiment 23 is the composition of embodiment 22, wherein R B4 For H.

[0056] Embodiment 24 is the composition of any one of embodiments 1-23, wherein at least one of the zwitterions comprises a compound of formula IV:

[0057]

[0058] in:

[0059] R C1 , R C2 and R C3 Each independently selected from C 1 –C 6 alkyl;

[0060] R C4 and R C5 are each independently selected from H and C(O)R H ;

[0061] Each occurrence of R H Independently for C 3 –C 21 side chains; and

[0062] R C4 and R C5 At least one of them is not H.

[0063] Embodiment 25 is the composition of embodiment 24, wherein R C4 and R C5 Each is independently C(O)R H .

[0064] Embodiment 26 is the composition of embodiment 24 or embodiment 25, wherein R C4 H and R C5 C(O)R H .

[0065] Embodiment 27 is the composition of any one of embodiments 1-26, wherein each of the one or more monoglycerides independently comprises a compound of Formula Ii or Formula I-ii:

[0066]

[0067] in:

[0068] R A1 and R A2 Each independently selected from H and C 1 –C 6Alkyl; and

[0069] R H C 3– C 27 Sidechain.

[0070] Embodiment 28 is the composition of embodiment 27, wherein R A1 and R A2 Each is H.

[0071] Embodiment 29 is the composition of embodiment 27 or embodiment 28, wherein R H is a saturated, unsubstituted side chain.

[0072] Embodiment 30 is the composition of any one of embodiments 27-29, wherein R H C 11 -C 21 Sidechain.

[0073] Embodiment 31 is the composition of any one of embodiments 1-26, wherein each of the one or more monoglycerides independently comprises a compound of Formula IA-i or Formula IA-ii:

[0074]

[0075] in:

[0076] R A1 and R A2 Each independently selected from H and C 1 –C 6 alkyl;

[0077] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0078] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C 1 –C 6 Alkyl, C2 –C 6 alkenyl and C 1 –C 6 alkoxy;

[0079] R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B any two of which may together with the carbon atoms to which they are attached form a double bond, a 3- to 6-membered heterocycloalkyl or a C 3 –C 6 cycloalkyl;

[0080] o is an integer from 0 to 17;

[0081] p is an integer from 0 to 17; and

[0082] the sum of o and p is from 0 to 17.

[0083] Embodiment 32 is the composition of Embodiment 31, wherein R A1 and R A2 are each H.

[0084] Embodiment 33 is the composition of any one of Embodiments 1-32, wherein each of said one or more salts independently comprises a compound of Formula II:

[0085]

[0086] wherein:

[0087] R H is a C 3 –C 27 side chain; and

[0088] X n+ is a cationic moiety having a formal charge n.

[0089] Embodiment 34 is the composition of Embodiment 33, wherein

[0090] X n+ is selected from Li + , Na + , K + , Cs + , Ag + , Ca2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + ;and

[0091] Each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C 3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, wherein

[0092] Each C 1– C 6 The alkyl group is optionally substituted with 1-3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 heterocycloalkyl, aryl and heteroaryl; and

[0093] Optionally, one or more occurrences of R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 Heterocycloalkyl.

[0094] Embodiment 35 is the composition of embodiment 33 or embodiment 34, wherein R H is a saturated, unsubstituted side chain.

[0095] Embodiment 36 is the composition of any one of embodiments 1-32, wherein each of the one or more salts independently comprises a compound of Formula IIA:

[0096]

[0097] in:

[0098] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6Alkenyl and C 1 –C 6 Alkoxy;

[0099] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0100] R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached may form a double bond, a 3- to 6-membered heterocycloalkyl ring, or a C 3 –C 6 Cycloalkyl;

[0101] o is an integer from 0 to 17;

[0102] p is an integer from 0 to 17;

[0103] The sum of o and p is from 0 to 17; and

[0104] X n+ It is the cationic part having a formal charge n.

[0105] Embodiment 37 is the composition of embodiment 36, wherein

[0106] X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + ;and

[0107] Each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C 3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, wherein

[0108] Each C 1 –C 6 The alkyl group is optionally substituted with 1-3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 heterocycloalkyl, aryl and heteroaryl; and

[0109] Optionally, one or more occurrences of R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 Heterocycloalkyl.

[0110] Embodiment 38 is a mixture comprising:

[0111] The composition of any one of embodiments 1-37; and

[0112] Solvent.

[0113] Embodiment 39 is the mixture of embodiment 38, comprising from about 30 wt % to about 99.9 wt % of the composition.

[0114] Embodiment 40 is the mixture of embodiment 38, comprising from about 90 wt % to about 99.5 wt % of the composition.

[0115] Embodiment 41 is a mixture of any one of embodiments 38-40, wherein the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether or any combination thereof.

[0116] Embodiment 42 is a coated agricultural product comprising an agricultural product and a layer disposed on a surface of the agricultural product, wherein the layer comprises the composition of any one of embodiments 1-37.

[0117] Embodiment 43 is the coated agricultural product of embodiment 42, wherein the layer is disposed on a stratum corneum surface of the agricultural product.

[0118] Embodiment 44 is the coated agricultural product of embodiment 42 or embodiment 43, wherein the layer has a thickness of about 0.1 micrometers to about 20 micrometers.

[0119] Embodiment 45 is the coated agricultural product of embodiment 42 or embodiment 43, wherein the layer has a thickness of about 0.1 micrometers to about 10 micrometers.

[0120] Embodiment 46 is a method of coating agricultural products, the method comprising:

[0121] The surface of the agricultural product is contacted with a mixture comprising a coating material and a solvent, wherein the coating material comprises

[0122] One or more C 4 –C 28 Monoglycerides of fatty acids;

[0123] One or more C 4 –C 28 Salts of fatty acids; and

[0124] one or more zwitterions;

[0125] wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:1; and

[0126] At least a portion of the solvent is removed to form a coating on the surface of the produce.

[0127] Embodiment 47 is the method of embodiment 46, wherein the surface is a cuticle surface of an agricultural product.

[0128] Embodiment 48 is the method of embodiment 46 or embodiment 47, wherein contacting the surface comprises:

[0129] spraying the mixture onto the surface; or

[0130] The produce is dipped in the mixture.

[0131] Embodiment 49 is the method of any one of embodiments 46-48, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

[0132] Embodiment 50 is the method described in any one of embodiments 46-49, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

[0133] Embodiment 51 is the method of any one of embodiments 46 to 50, wherein the concentration of the coating material in the mixture is from about 1 mg / mL to about 200 mg / mL.

[0134] Embodiment 52 is the method of any one of embodiments 46 to 50, wherein the concentration of the coating material in the mixture is about 50 mg / mL to about 200 mg / mL.

[0135] Embodiment 53 is the method of any one of embodiments 46 to 52, wherein the coating material further comprises one or more inorganic salts.

[0136] Embodiment 54 is the method of embodiment 53, wherein the one or more inorganic salts comprises sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any mixture thereof.

[0137] Embodiment 55 is the method of embodiment 53 or embodiment 54, wherein the total amount of the one or more inorganic salts in the mixture has a concentration of about 5 ppm to about 500 ppm on a weight basis.

[0138] Embodiment 56 is the method of any one of embodiments 46-55, wherein:

[0139] The one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the coating material.

[0140] The total content of the one or more salts is from about 1% to about 10% by weight of the coating material; and

[0141] The total content of the one or more zwitterions is from about 1% to about 10% by weight of the coating material.

[0142] Embodiment 57 is the method of any one of embodiments 46-56, wherein:

[0143] The ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 6:1; and

[0144] The ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 10:1 to about 1:10.

[0145] Embodiment 58 is the method of any one of embodiments 46-57, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions comprise at least about 80% by weight of the coating material.

[0146] Embodiment 59 is the method of any one of embodiments 46 to 58, wherein the coating material and solvent comprise at least about 95% by weight of the mixture.

[0147] Embodiment 60 is the method of any one of embodiments 46-59, wherein the coating material comprises lecithin, hydrolyzed lecithin, or a combination thereof, comprising at least one of the zwitterions.

[0148] Embodiment 61 is the method of embodiment 60, wherein the coating material comprises about 1 wt % to about 10 wt % of lecithin, hydrolyzed lecithin, or a combination thereof.

[0149] Embodiment 62 is the method of any one of embodiments 46-61, wherein at least one of the zwitterions comprises

[0150] Positively charged groups, including quaternary ammonium groups or phosphonium groups; and

[0151] Negatively charged groups include phosphate groups, sulfonate groups or carboxylate groups.

[0152] Embodiment 63 is the method of any one of embodiments 46-62, wherein at least one of the zwitterions comprises betaine, phosphatidylcholine, lysophosphatidylcholine, hydroxysulfobetaine, or amphoacetate.

[0153] Embodiment 64 is a method of coating agricultural products, the method comprising:

[0154] contacting the surface of the agricultural product with the mixture of any one of embodiments 38-41; and

[0155] At least a portion of the solvent is removed to form a coating on the surface of the produce.

[0156] The details of one or more embodiments of the subject matter of the present disclosure are set forth in the drawings and the description. Other features, aspects, and advantages of the subject matter will become apparent from the description, drawings, and claims.

[0157] BRIEF DESCRIPTION OF THE DRAWINGS

[0158] Figure 1 is a graph showing the viscoelastic properties of certain mixtures described in this application.

[0159] Figure 2 is a graph showing respiration production of California avocados coated with certain compositions described in this application.

[0160] Figure 3 is a graph showing respiration production of California avocados coated with certain compositions described in this application.

[0161] Detailed Description

[0162] The present disclosure relates to compositions comprising monoglycerides and co-surfactants. Specifically, the compositions described herein can be coated on agricultural products to provide an improved barrier, for example, to gas or water. Such coatings can better limit the loss of quality and / or CO2 in agricultural products compared to coatings lacking co-surfactants. 2 Additionally, the solvent mixtures of the compositions described herein can have physical properties better suited for application to agricultural products, for example, by spraying or dipping.

[0163] Reference will now be made in detail to certain embodiments of the disclosed subject matter.While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the illustrated subject matter is not intended to limit the claims to the disclosed subject matter.

[0164] definition

[0165] Unless the context clearly dictates otherwise, the terms "a", "an", and "the" used in this application include one or more. Unless otherwise specified, the term "or" is used to refer to a non-exclusive "or". The expression "at least one of A and B" has the same meaning as "A, B, or A and B". In addition, it should be understood that the expressions or terms used in this disclosure (not otherwise defined) are for illustrative purposes only and not for limiting purposes. The use of any section headings is intended to assist in reading this document and should not be construed as limiting; information related to the section heading may appear within or outside that particular section.

[0166] Values ​​expressed in range format should be interpreted in a flexible manner to include not only the values ​​explicitly listed as range limits, but also all individual values ​​or subranges contained within the range, as if each value and subrange were explicitly listed. For example, a range of "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also individual values ​​(e.g., 1%, 2%, 3%, and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the specified range. Unless otherwise specified, the expression "about X to Y" has the same meaning as "about X to about Y". Similarly, unless otherwise specified, the expression "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z".

[0167] As used in this application, the term "about" allows a value or range to vary within 10% of the stated value or limit of the stated range.

[0168] In the methods described in this application, the actions may be performed in any order, except where a time or order of operations is explicitly described. Furthermore, unless explicit claim language describes that the described actions should be performed separately, they may be performed simultaneously. For example, a claimed action of performing X and a claimed action of performing Y may be performed simultaneously in a single operation, and the resulting method would fall within the literal scope of the claimed method.

[0169] As used in this application, the term "monoglyceride" refers to the condensation product of a glycerol molecule and a fatty acid, i.e., a glycerol group is connected to a fatty acid by an ester bond. Monoglycerides can be, but do not necessarily need to be, derived from a condensation reaction. For example, monoglycerides can be obtained by an esterification reaction between glycerol and fatty acids, by transesterification of triglycerides with glycerol (glycerol decomposition), etc. Monoglycerides may also be referred to as glycerol monoalkanoates. If the glycerol group is connected to an ester bond at position 1 (e.g., in 2,3-dihydroxypropane-1-yl octadecanoate), the monoglyceride may be referred to as 1-monoglyceride or 1-glycerol alkanoate (e.g., in 1-glycerol octadecanoate). If the glycerol group is connected to an ester bond at position 2 (e.g., in 1,3-dihydroxypropane-2-yl hexadecanoate), the monoglyceride may be referred to as 2-monoglyceride or 2-glyceryl alkanoate (e.g., in 2-glyceryl hexadecanoate). The glycerol group of the monoglyceride may be unsubstituted (for example, in 2,3-dihydroxypropan-1-ylalkanoate) or may be further substituted with one or more groups that are not fatty acids (for example, in 1,3-dialkoxypropan-2-ylalkanoate).

[0170] As used in this application, the term "fatty acid" refers to a carboxylic acid with an aliphatic side chain. The fatty acid may be naturally occurring or non-naturally occurring, and may include a side chain that is branched or unbranched (e.g., straight chain), substituted or unsubstituted, saturated or unsaturated.

[0171] As used in this application, the term "side chain" refers to the aliphatic portion of a fatty acid or a portion thereof. Unless otherwise specified, the side chain of a given fatty acid includes the carbon of the carboxylic acid group. For example, dodecanoic acid can be described as including a linear, saturated C 12 Side chain, also represented by R H -C(O)OH, where R H It is linear, saturated C 11 Side chains. Side chains may be present in compounds that are not fatty acids, such as esters or amides, and may, but need not necessarily, be derived from fatty acids. For example, dodecylamide may be described as an amide of a fatty acid, whether or not the compound is actually derived from dodecanoic acid.

[0172] The term "salt" used in connection with the disclosed compounds (e.g., fatty acids) refers to derivatives of the compounds in which the parent compound is modified by converting the acid or base moiety into their salt form. Examples of such salts include, but are not limited to, inorganic or organic acid salts of basic residues (e.g., amines), alkali or organic salts of acidic residues (e.g., carboxylic acids), and the like.

[0173] If certain features of the compounds described in this application are disclosed in the form of groups or ranges, such disclosure includes each and all individual subcombinations of the members of such groups and ranges. For example, the term "C 1 –C 6 "Alkyl" includes (but is not limited to) methyl, ethyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl and C 6 alkyl.

[0174] As used herein, the term "n-membered," where n is an integer, generally describes the number of ring-forming atoms in a moiety, where the number of ring-forming atoms is n. For example, piperidinyl is an example of a 6-membered heterocycloalkyl ring, and 1,2,3,4-tetrahydronaphthalene is an example of a 10-membered cycloalkyl.

[0175] As used in this application, the term "substituted" means that an atom or a group of atoms replaces hydrogen as a "substituent" connected to another group. Unless otherwise indicated, "substituted" refers to any degree of substitution, such as mono-, di-, tri-, tetra- or penta-substitution, where the substitution is allowed. Substituents are independently selected, and substitutions can be located at any chemically accessible position. Substitution on a given atom is limited by valence. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent (e.g., oxo) can replace two hydrogen atoms.

[0176] As used in this application, the term "C n –C m " represents a range including the endpoints, wherein n and m are integers representing the number of carbon atoms. For example, C 1 –C 4 , C 1 –C 6 wait.

[0177] As used in this application, the term "alkyl" refers to a saturated hydrocarbon group which may be straight chain or branched. n –C m"Alkyl" refers to an alkyl radical having from n to m carbon atoms. Alkyl radicals formally correspond to alkanes in which one CH bond is replaced by the point of attachment of the alkyl radical to the rest of the compound. Examples of alkyl moieties include, but are not limited to, chemical groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl; higher homologues such as 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, and the like.

[0178] As used in this application, the term "alkenyl" refers to a straight or branched hydrocarbon group, corresponding to a hydrocarbon group having one or more carbon-carbon double bonds. Alkenyl formally corresponds to olefins, in which one CH bond is replaced by the point of attachment of the alkenyl group to the rest of the compound. n –C m "Alkenyl" refers to an alkenyl group having n to m carbons. Examples of alkenyl groups include, but are not limited to, ethenyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, and the like.

[0179] As used in this application, the term "alkoxy" refers to a group of the formula -O-alkyl, wherein alkyl is as defined above. n –C m The term "alkoxy" refers to an alkoxy group in which the alkyl group has n to m carbons. Examples of alkoxy groups include methoxy, ethoxy, propoxy (eg, n-propoxy and isopropoxy), tert-butoxy, and the like.

[0180] As used in this application, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic or polycyclic), including cyclic alkyl and alkenyl. n –C m "Cycloalkyl" refers to a cycloalkyl radical having n to m ring member carbon atoms. Cycloalkyl radicals may include fused, bridged and / or spiro bicyclic or polycyclic ring systems. Examples of cycloalkyl radicals include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcaryl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.2.0]hexyl, bicyclo[3.1.0]hexyl, bicyclo[3.2.0]heptyl and bicyclo[3.3.0]octyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl and bicyclo[1.1.1]pentyl, and the like.

[0181] As used in this application, the term "heterocycloalkyl" refers to a non-aromatic ring system (monocyclic, bicyclic or polycyclic) that may optionally contain one or more alkenylene groups as part of the ring structure, which has at least one heteroatom ring member independently selected from nitrogen, sulfur, oxygen and phosphorus. The term "n to m-membered ring heterocycloalkyl" refers to a heterocycloalkyl group having n to m ring atoms. The ring-forming carbon atoms and heteroatoms of the heterocycloalkyl group may be optionally oxidized to form oxo or thiol or other oxidized bonds (e.g., C(O), S(O), C(S), S(O) 2 , N-oxides, etc.) or nitrogen atoms may be quaternized. Heterocycloalkyl may be connected by ring-forming carbon atoms or ring-forming heteroatoms. Heterocycloalkyl may include double bonds, for example, up to 3 double bonds. Examples of heterocycloalkyl include, but are not limited to, azetidinyl, dihydrofuranyl, dihydrothienyl, tetrahydrothienyl, tetrahydrofuranyl, tetrahydrotriazinyl, tetrahydropyrazolyl, tetrahydrooxazinyl, tetrahydropyrimidinyl, octahydrobenzofuranyl, octahydrobenzimidazolyl, octahydrobenzothiazolyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydropyranyl, tetrahydrothiazinyl, tetrahydrothiadiazinyl, tetrahydrooxazolyl, morpholinyl, oxetane, dioxetane, dioxolane, dioxane 1-H-isoindolyl, 2-azabicyclo[2.2.1]heptanyl, 3-azabicyclo[3.1.0]hexyl, 3-azabicyclo[4.1.0]heptyl, and the like. Other examples of heterocycloalkyl include tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, piperazin-2-yl, 1,3-oxazolidin-3-yl, 1,4- Oxazepan-1-yl, isothiazolidinyl, 1,3-thiazolidin-3-yl, 1,2-pyrazolidin-2-yl, 1,2-tetrahydrothiazin-2-yl, 1,3-thiazin-3-yl, 1,2-tetrahydrodiazin-2-yl, 1,3-tetrahydrodiazin-1-yl, 1,4-oxazin-4-yl, oxazolidinone, 2-oxo-piperidinyl (e.g., 2-oxo-piperidin-1-yl), and the like.

[0182] Composition

[0183] The present application provides a method comprising one or more C 4 –C 28Monoacylglycerols of fatty acids, one or more C 4 –C 28 A composition of salts of fatty acids and one or more zwitterions. As described in the present application, the zwitterionic compound can act as a co-surfactant (e.g., together with the fatty acid salt) to reduce the difference in surface energy between its suspension, colloid or solution and the solid surface on which the suspension, colloid or solution is disposed.

[0184] In some embodiments, the total content of the one or more monoacylglycerols is from about 40 wt% to about 99 wt% of the composition, e.g., from about 40 wt% to about 98 wt%, from about 40 wt% to about 96 wt%, from about 70 wt% to about 99 wt%, from about 70 wt% to about 98 wt%, from about 70 wt% to about 96 wt%, from about 80 wt% to about 99 wt%, from about 80 wt% to about 98 wt% or from about 80 wt% to about 96 wt% of the composition. In some embodiments, the total content of the one or more salts is from about 0.1 wt% to about 20 wt% of the composition, e.g., from about 0.1 wt% to about 15 wt%, from about 0.1 wt% to about 10 wt%, from about 1 wt% to about 20 wt%, from about 1 wt% to about 15 wt%, from about 1 wt% to about 10 wt%, from about 2 wt% to about 20 wt%, from about 2 wt% to about 15 wt% or from about 2 wt% to about 10 wt% of the composition. In some embodiments, the total content of the one or more zwitterions is from about 0.1 wt% to about 20 wt% of the composition, e.g., from about 0.1 wt% to about 15 wt%, from about 0.1 wt% to about 10 wt%, from about 1 wt% to about 20 wt%, from about 1 wt% to about 15 wt%, from about 1 wt% to about 10 wt%, from about 2 wt% to about 20 wt%, from about 2 wt% to about 15 wt% or from about 2 wt% to about 10 wt% of the composition.

[0185] In some embodiments, the composition further comprises an inorganic salt. In some embodiments, the composition contains up to about 1 wt% of the inorganic salt, e.g., from about 0.01 wt% to about 1 wt%, from about 0.01 wt% to about 0.75 wt%, from about 0.01 wt% to about 0.5 wt%, from about 0.05 wt% to about 1 wt%, from about 0.05 wt% to about 0.75 wt%, from about 0.05 wt% to about 0.5 wt%, from about 0.1 wt% to about 1 wt%, from about 0.1 wt% to about 0.75 wt% or from about 0.1 wt% to about 0.5 wt% of the inorganic salt. In some embodiments, the inorganic salt comprises sodium chloride, potassium chloride, sodium bromide, potassium bromide or any combination thereof. In some embodiments, the inorganic salt comprises sodium chloride.

[0186] In some embodiments, the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from 100: 1 to about 4: 1, e.g., from about 100: 1 to about 6: 1, from about 100: 1 to about 8: 1, from about 75: 1 to about 4: 1, from about 75: 1 to about 6: 1, from about 75: 1 to about 4: 1, from about 50: 1 to about 4: 1, from about 50: 1 to about 6: 1, or from about 50: 1 to about 8: 1.

[0187] In some embodiments, the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is about 10:1 to about 1:10, e.g., about 10:1 to about 1:8, about 10:1 to about 1:6, about 5:1 to about 1:10, about 5:1 to about 1:8, about 5:1 to about 1:6, about 1:1 to about 1:10, about 1:1 to about 1:8, or about 1:1 to about 1:6.

[0188] In some embodiments, the one or more monoglycerides, one or more salts, and one or more zwitterions comprise at least about 80% by weight of the composition, e.g., at least about 85%, at least about 90%, at least about 95%, at least about 97.5%, at least about 98%, or at least about 99% by weight of the composition.

[0189] C 4 –C 28 Monoglycerides of fatty acids

[0190] The composition described in this application comprises one or more C 4 –C 28 In some embodiments, the composition comprises a monoglyceride of a C 4 –C 28 In some embodiments, the composition comprises two, three or more C 4 –C 28 Monoglycerides of fatty acids, such as two C 4 –C 28 Monoglycerides of fatty acids. In some embodiments, the monoglycerides include monoglycerides of one or more naturally occurring fatty acids.

[0191] The monoglycerides may include one or more 1-monoglycerides, one or more 2-monoglycerides, or mixtures thereof. In some embodiments, the monoglycerides include one or more 2,3-dihydroxypropane-1-yl esters of fatty acids, one or more 1,3-dihydroxypropane-2-yl esters of fatty acids, or mixtures thereof. In some embodiments, the 1-monoglycerides account for at least about 50% by weight, at least about 60% by weight, at least about 70% by weight, at least about 75% by weight, at least about 80% by weight, at least about 85% by weight, at least about 90% by weight, or at least about 95% by weight, or about 100% by weight of the monoglycerides present in the composition. In some embodiments, 1-monoglyceride comprises about 70% to about 100%, about 70% to about 95%, about 70% to about 90%, about 75% to about 100%, about 75% to about 95%, about 75% to about 90%, about 80% to about 100%, about 80% to about 95%, or about 80% to about 90% by weight of the monoglycerides present in the composition.

[0192] In some embodiments, the monoglyceride includes one or more C 6 –C 28 Fatty acids, C 8 –C 28 Fatty acids, C 4 –C 24 Fatty acids, C 6 –C 24 Fatty acids, C 12 –C 24 Fatty acids, C 4 –C 22 Fatty acids, C 6 –C 22 Fatty acids or C 12 –C 22 In some embodiments, the one or more monoglycerides include unsubstituted side chains, such as unsubstituted C 12 –C 22 In some embodiments, one or more monoglycerides include linear side chains, such as linear C 12 –C 22 In some embodiments, one or more monoglycerides include saturated side chains, such as saturated C 12 –C 22 Sidechain.

[0193] In some embodiments, the monoglyceride comprises one or more compounds of Formula Ii:

[0194]

[0195] in:

[0196] R A1 and R A2 Each independently selected from H and C 1 –C 6 Alkyl; and

[0197] R H C 3 –C 27 Sidechain.

[0198] In some embodiments, the monoglyceride comprises one or more compounds of Formula I-ii:

[0199]

[0200] in:

[0201] R A1 and R A2 Each independently selected from H and C 1 –C 6 Alkyl; and

[0202] R H C 3 –C 27 Sidechain.

[0203] In some embodiments, each of the one or more monoglycerides independently comprises a compound of Formula Ii or Formula I-ii. In some embodiments of Formula Ii or Formula I-ii, R A1 and R A2 Each is H. In some embodiments of Formula Ii or Formula I-ii, R H is a saturated side chain. In some embodiments of Formula Ii or Formula I-ii, R H is an unsubstituted side chain. In some embodiments of Formula Ii or Formula I-ii, R H is a linear side chain. In some embodiments of Formula Ii or Formula I-ii, R H C 5 –C 17 In some embodiments of Formula Ii or Formula I-ii, R H C 11 –C 21 Sidechain.

[0204] In some embodiments, the monoglyceride comprises one or more compounds of Formula IA-i:

[0205]

[0206] in:

[0207] R A1 and R A2 Each independently selected from H and C 1 –C 6 alkyl;

[0208] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0209] Each occurrence of R 10A , R 10B , R 11A and R 11B Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0210] R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached may form a double bond, a 3- to 6-membered heterocycloalkyl ring, or a C 3 –C 6 Cycloalkyl;

[0211] o is an integer from 0 to 17;

[0212] p is an integer from 0 to 17; and

[0213] The sum of o and p is 0 to 17.

[0214] In some embodiments, the monoglyceride comprises one or more compounds of Formula IA-ii:

[0215]

[0216] in:

[0217] R A1 and R A2 Each independently selected from H and C 1 –C 6 alkyl;

[0218] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0219] Each occurrence of R 10A , R 10B , R 11A and R 11B Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0220] R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached may form a double bond, a 3- to 6-membered heterocycloalkyl ring, or a C 3 –C 6 Cycloalkyl;

[0221] o is an integer from 0 to 17;

[0222] p is an integer from 0 to 17; and

[0223] the sum of o and p is from 0 to 17.

[0224] In some embodiments, one or more of the monoglycerides independently comprise a compound of Formula IA-i or Formula IA-ii. In some embodiments of Formula IA-i or Formula IA-ii, R A1 and R A2 are each H. In some embodiments of Formula IA-i or Formula IA-ii, each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B are independently selected from H and OH. In some embodiments of Formula IA-i or Formula IA-ii, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B on adjacent carbon atoms together with the carbon atoms to which they are attached form ethylene oxide. In some embodiments of Formula IA-i or Formula IA-ii, two pairs, one pair, or none of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 on adjacent carbon atoms and each occurrence of R 10A , R 10B , R 11A and R 11B form a double bond together with the carbon atoms to which they are attached. In some embodiments of Formula IA-i or Formula IA-ii, R 1 , R 2, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 A pair or none of them and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atom to which they are attached, they form ethylene oxide. In some embodiments of Formula IA-i or Formula IA-ii, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Two, one, or none of the R 10A , R 10B , R 11A and R 11B For OH.

[0225] In some embodiments of Formula IA-i or Formula IA-ii, the sum of o and p is 0 to 13, 0 to 11, 0 to 9, 0 to 7, 5 to 17, 5 to 13, 5 to 11, 5 to 9, 5 to 7, 7 to 17, 7 to 13, 7 to 11, 7 to 9, 9 to 17, 9 to 13, 9 to 11, 11 to 17, or 11 to 13.

[0226] In some embodiments, the monoglycerides include one or more 1-monoglycerides or 2-monoglycerides, for example, the 2,3-dihydroxypropyl-1-yl esters or 1,3-dihydroxypropyl-2-yl esters of heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, 9-hydroxyhexadecanoic acid, 10-hydroxyhexadecanoic acid, 9,10-dihydroxyhexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, 9,10,16-trihydroxyhexadecanoic acid, 9,10-epoxyhexadecanoic acid, (9Z)-hexadec-9-enoic acid, (9E)-hexadec-9-enoic acid, 9,10-epoxy-16-hydroxyhexadecanoic acid, 16-hydroxy-(9Z)-hexadec-9-enoic acid, 16-hydroxy-(9E)-hexadec-9-enoic acid, 9-hydroxyoctadecanoic acid, 10-hydroxyoctadecanoic acid, 9,10-dihydroxyoctadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, 9,10,18-trihydroxyoctadecanoic acid, 9,10-epoxyoctadecanoic acid, (9Z)-octadec-9-enoic acid, (9E)-octadec-9-enoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, 18-hydroxy-(9E)-octadec-9-enoic acid, (13Z)-docos-13-enoic acid, or (13E)-docos-13-enoic acid.

[0227] C 4 –C 28 Salts of fatty acids

[0228] The compositions described in the present application comprise one or more C 4 –C 28 Salts of fatty acids. In some embodiments, the composition comprises one C 4 –C 28 Salts of fatty acids. In some embodiments, the composition comprises two, three, or more C 4 –C 28 Salts of fatty acids, such as two C 4 –C 28 Salts of fatty acids. In some embodiments, the salts include one or more salts of naturally occurring fatty acids.

[0229] In some embodiments, the salts include one or more C 6 –C 28 fatty acids, C 8 –C 28 fatty acids, C 4 –C 24 fatty acids, C 6–C 24 Fatty acids, C 12 –C 24 Fatty acids, C 4 –C 22 Fatty acids, C 6 –C 22 Fatty acids or C 12 –C 22 In some embodiments, the one or more salts include unsubstituted side chains, such as unsubstituted C 12 –C 22 In some embodiments, the one or more salts include linear side chains, such as linear C 12 –C 22 In some embodiments, the one or more salts include saturated side chains, such as saturated C 12 –C 22 Sidechain.

[0230] In some embodiments, the salt comprises one or more compounds of Formula II

[0231]

[0232] in:

[0233] R H C 3 –C 27 Sidechains; and

[0234] X n+ It is the cationic part having a formal charge n.

[0235] In some embodiments, each of the one or more salts independently comprises a compound of Formula II. In some embodiments of Formula II, X n+ Selected from Li + 、Na + , K + , Cs + Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + , where each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C 3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, and wherein each C1 –C 6 The alkyl group is optionally substituted with 1 to 3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 In some embodiments, X n+ for (R D ) 4 N + , and one or more R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 In some embodiments of Formula II, X n+ Selected from Na + , K + , Ca 2+ Mg 2+ and Zn 2+ In some embodiments of Formula II, R H is a saturated side chain. In some embodiments of Formula II, R H is an unsubstituted side chain. In some embodiments of Formula II, R H is a linear side chain. In some embodiments of Formula II, R H C 5 –C 17 In some embodiments of Formula II, R H C 11 –C 21 Sidechain.

[0236] In some embodiments, the salt comprises one or more compounds of Formula IIA

[0237]

[0238] in:

[0239] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6Alkoxy;

[0240] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy;

[0241] R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached may form a double bond, a 3- to 6-membered heterocycloalkyl ring, or a C 3 –C 6 Cycloalkyl;

[0242] o is an integer from 0 to 17;

[0243] p is an integer from 0 to 17;

[0244] The sum of o and p is from 0 to 17; and

[0245] X n+ It is the cationic part having a formal charge n.

[0246] In some embodiments, each of the one or more salts independently comprises a compound of Formula IIA. In some embodiments of Formula IIA, X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + , where each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, and wherein each C 1 –C 6 The alkyl group is optionally substituted with 1 to 3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 In some embodiments, X n+ for (R D ) 4 N + , and one or more R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 In some embodiments of Formula II, X n+ Selected from Na + , K + , Ca 2+ Mg 2+ and Zn 2+ .

[0247] In some embodiments of Formula IIA, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each of the R 10A , R 10B , R 11A and R 11B Each occurrence of is independently selected from H and OH. In some embodiments of Formula IIA, R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached together form ethylene oxide. In some embodiments of Formula IIA, R on adjacent carbon atoms 1, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Two pairs, one pair or none and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atoms to which they are attached, they form a double bond. In some embodiments of Formula IIA, R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 A pair or none of them and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atom to which they are attached, they form ethylene oxide. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Two, one, or none of them and each occurrence of R 10A , R 10B , R 11A and R 11B For OH.

[0248] In some embodiments of Formula IIA, the sum of o and p is 0 to 13, 0 to 11, 0 to 9, 0 to 7, 5 to 17, 5 to 13, 5 to 11, 5 to 9, 5 to 7, 7 to 17, 7 to 13, 7 to 11, 7 to 9, 9 to 17, 9 to 13, 9 to 11, 11 to 17, or 11 to 13.

[0249] In some embodiments, the salt comprises a salt of one or more saturated, linear, unsubstituted fatty acids, such as sodium, potassium, silver, calcium, magnesium or zinc salts. In some embodiments, the salt comprises a salt of one or more heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, octadecanoic acid, 19decanoic acid, eicosanoic acid, heneicosanoic acid or docosanoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadecanoic acid or 18-hydroxy-(9E)-octadecanoic acid, such as sodium, potassium, silver, calcium, magnesium or zinc salts.

[0250] Zwitterions

[0251] The compositions described in the present application include one or more zwitterions. In some embodiments, the composition includes one zwitterion. In some embodiments, the composition includes two, three or more zwitterions, for example, two zwitterions. In some embodiments, one or more of the zwitterions cannot be converted to a neutral, uncharged form. For example, in some embodiments, each of the zwitterions cannot be converted to a neutral, uncharged form.

[0252] In some embodiments, one or more of the zwitterions include a positively charged group, including a quaternary ammonium group or a phosphonium group. In some embodiments, one or more of the zwitterions include a negatively charged group, including a phosphate group, a sulfonate group, or a carboxylate group. In some embodiments, one or more of the zwitterions include a quaternary ammonium group and a negatively charged group, including a phosphate group, a sulfonate group, or a carboxylate group.

[0253] In some embodiments, the zwitterions include betaine, phosphatidylcholine, lysophosphatidylcholine, phosphatidylserine, lysophosphatidylserine, hydroxysultaine, amphoacetate, or any combination thereof. In some embodiments, betaine, phosphatidylcholine, lysophosphatidylcholine, phosphatidylserine, lysophosphatidylserine, hydroxysultaine, and amphoacetate account for at least about 50 wt %, at least about 60 wt %, at least about 70 wt %, at least about 75 wt %, at least about 80 wt %, at least about 85 wt %, at least about 90 wt %, or at least about 95 wt % of the zwitterions present in the composition.

[0254] In some embodiments, the composition comprises lecithin or hydrolyzed lecithin, including one or more zwitterions. In some embodiments, the composition comprises lecithin or hydrolyzed lecithin (lysolecithin), including one or more zwitterions glycerophospholipids, for example, such as, phosphatidylcholine or lysophosphatidylcholine. In some embodiments, the lecithin or hydrolyzed lecithin contains at least about 10wt% or at least about 15wt% or at least about 20wt% zwitterions. In some embodiments, the composition comprises lecithin, and the lecithin includes about 15wt% to about 35wt% zwitterions, including, for example, phosphatidylcholine or phosphatidylserine. In some embodiments, the composition comprises lysolecithin, and the lysolecithin includes about 15 wt% to about 35 wt% zwitterions, including, for example, lysophosphatidylcholine or lysophosphatidylserine.

[0255] In some embodiments, the zwitterion comprises one or more compounds of Formula III-i:

[0256]

[0257] in:

[0258] R B1 , R B2 and R B3 Each independently selected from C 1 –C 22 Alkyl and (C 1 –C 6 Alkyl)-NR B4 C(O)R H ;

[0259] Each occurrence of R B4 are independently H or C 1 –C 6 alkyl; and

[0260] Each occurrence of R H Independently for C 3 –C 21 Sidechain.

[0261] In some embodiments, the zwitterion comprises one or more compounds of Formula III-ii:

[0262]

[0263] in:

[0264] R B1 , R B2 and R B3 Each independently selected from C 1 –C22 Alkyl and (C 1 –C 6 Alkyl)-NR B4 C(O)R H ;

[0265] Each occurrence of R B4 are independently H or C 1 –C 6 alkyl; and

[0266] Each occurrence of R H Independently for C 3 –C 21 Sidechain.

[0267] In some embodiments of Formula III-i or Formula III-ii, R B1 and R B2 Each is C 1 In some embodiments of Formula III-i or Formula III-ii, R B3 C 1 –C 6 In some embodiments of Formula III-i or Formula III-ii, R B3 C 10 –C 20 In some embodiments of Formula III-i or Formula III-ii, R B3 For (C 1 –C 6 Alkyl)-NR B4 C(O)R H , and R B4 is H. In some embodiments of Formula III-i or Formula III-ii, R H C 6 –C 21 Sidechain.

[0268] In some embodiments, the zwitterion comprises one or more compounds of Formula IIIA-i:

[0269]

[0270] in:

[0271] R B1 and R B2 Each independently selected from C 1 –C 6 alkyl;

[0272] R B4 H or C 1 –C 6 alkyl; and

[0273] R H C 3 –C 21 Sidechain.

[0274] In some embodiments, the zwitterion comprises one or more compounds of Formula IIIA-ii:

[0275]

[0276] in:

[0277] R B1 and R B2 Each independently selected from C 1 –C 6 alkyl;

[0278] R B4 H or C 1 –C 6 alkyl; and

[0279] R H C 3 –C 21 Sidechain.

[0280] In some embodiments of Formula IIIA-i or Formula IIIA-ii, R B1 and R B2 Each is C 1 In some embodiments of Formula IIIA-i or Formula IIIA-ii, R B4 is H. In some embodiments of Formula IIIA-i or Formula IIIA-ii, R H C 6 –C 21 Sidechain.

[0281] In some embodiments, the zwitterion comprises one or more compounds of Formula IV:

[0282]

[0283] in:

[0284] R C1 , R C2 and R C3 Each independently selected from C 1 –C 6 alkyl;

[0285] R C4 and R C5 are each independently selected from H and C(O)R H ;

[0286] Each RH Independently for C 3 –C 21 side chains; and

[0287] R C4 and R C5 At least one of them is not H.

[0288] In some embodiments of Formula IV, R C1 , R C2 and R C3 Each is C 1 In some embodiments, R C4 H and R C5 C(O)R H In some embodiments, each occurrence of R H Independently for C 6 –C 21 Sidechain.

[0289] In some embodiments, compounds of Formula III-i, Formula III-ii, Formula IIIA-i, Formula IIIA-ii, and Formula IV comprise at least about 50 weight %, at least about 60 weight %, at least about 70 weight %, at least about 75 weight %, at least about 80 weight %, at least about 85 weight %, at least about 90 weight %, or at least about 95 weight % of the zwitterions present in the composition.

[0290] Additional components

[0291] The compositions described in the present application may include one or more additional components, such as components that are non-toxic and safe for human and / or animal consumption. For example, the compositions may include direct or indirect food additives or food contact substances approved by the U.S. Food and Drug Administration (FDA), components that meet FDA regulatory requirements for use as food additives or food contact substances, or components that are generally recognized as safe (GRAS) by the FDA.

[0292] In some embodiments, the compositions described herein further include one or more fatty acids, such as C 4 –C 22 Fatty acids, or esters thereof, such as C 1 –C 6 In some embodiments, the composition comprises less than about 10 wt%, such as less than about 5 wt%, less than about 2 wt%, less than about 1 wt%, or is free of one or more triglycerides, diglycerides, acetylated monoglycerides, lactated monoglycerides, succinate monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenes, alkaloids, alcohols, alkanes, aldehydes, and any salts thereof.

[0293] mixture

[0294] The application also provides a mixture comprising the composition described in the application and a solvent. In some embodiments, the mixture includes a dispersion of the composition described in the application in a solvent. In some embodiments, the solvent includes water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, ether, methyl tert-butyl ether or any combination thereof. In some embodiments, the solvent includes water, ethanol or a combination thereof.

[0295] In some embodiments, the mixture comprises about 30% to about 99.9% by weight, about 30% to about 99.5% by weight, about 30% to about 99% by weight, about 50% to about 99.9% by weight, about 50% to about 99.5% by weight, about 50% to about 99% by weight, about 90% to about 99.9% by weight, about 90% to about 99.5% by weight, or about 90% to about 99% by weight of solvent.

[0296] In some embodiments, the concentration of the composition in the mixture is about 1 mg / mL to about 200 mg / mL, about 1 mg / mL to about 150 mg / mL, about 1 mg / mL to about 125 mg / mL, about 1 mg / mL to about 100 mg / mL, about 25 mg / mL to about 200 mg / mL, about 25 mg / mL to about 150 mg / mL, about 25 mg / mL to about 125 mg / mL, about 25 mg / mL to about 100 mg / mL, about 50 mg / mL to about 200 mg / mL, about 50 mg / mL to about 150 mg / mL, about 50 mg / mL to about 125 mg / mL, or about 50 mg / mL to about 100 mg / mL.

[0297] In some embodiments, the composition comprises an inorganic salt as described herein, and the inorganic salt is present in the mixture at a concentration of about 1 ppm to about 1,000 ppm, about 1 ppm to about 500 ppm, about 1 ppm to about 250, about 25 ppm to about 1,000 ppm, about 25 ppm to about 500 ppm, about 25 ppm to about 250 ppm, about 50 ppm to about 1,000 ppm, about 50 ppm to about 500 ppm, about 50 ppm to about 250 ppm.

[0298] Coating

[0299] The application also provides coated agricultural products, including agricultural products and a layer formed by the composition described in the application, and the layer is disposed on the surface of the agricultural product. In some embodiments, the agricultural product is edible agricultural products, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, agricultural products, meat, eggs, dairy products, seafood, cereals or any other consumable items. In other embodiments, the agricultural product is inedible agricultural products, including, for example, inedible flowers, seeds, twigs, stems, leaves, whole plants, etc. In some embodiments, the layer is disposed on the outer surface (for example, cuticle surface) of the agricultural product.

[0300] In some embodiments, the layer has a thickness of about 0.1 micrometer to about 20 micrometers, for example, about 0.1 micrometer to about 15 micrometers, about 0.1 micrometer to about 10 micrometers, about 0.5 micrometer to about 20 micrometers, about 0.5 micrometer to about 15 micrometers, about 0.5 micrometer to about 10 micrometers, about 1 micrometer to about 20 micrometers, about 1 micrometer to about 15 micrometers, or about 1 micrometer to about 10 micrometers.

[0301] Coating method

[0302] The present application also provides a method for coating agricultural products, the method comprising contacting the surface of the agricultural product with a mixture comprising a coating material and a solvent, and removing at least a portion of the solvent to form a coating on the surface of the agricultural product. The coating material comprises one or more C 4 –C 28 Monoglycerides of fatty acids, one or more C 4 –C 28 In some embodiments, the coating material is a composition as described herein. For example, in some embodiments, the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more salts and the one or more zwitterions is about 100:1 to about 4:1. In some embodiments, the coating material comprises one or more C 4 –C 28 monoglycerides of fatty acids (total content of about 40% to about 99% by weight of the coating material), one or more C 4 –C 28 Salts of fatty acids (total content 0.1% to about 20% by weight of the composition) and one or more zwitterions (total content 0.1% to about 20% by weight of the coating material).

[0303] In some embodiments of the coating method, the agricultural product is an edible agricultural product, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, agricultural products, meats, eggs, dairy products, seafood, grains, or any other consumable items. In other embodiments of the coating method, the agricultural product is an inedible agricultural product, including, for example, inedible flowers, seeds, twigs, stems, leaves, whole plants, etc. In some embodiments, the method includes contacting the outer surface (e.g., cuticle surface) of the agricultural product with a mixture containing a coating material.

[0304] In some embodiments of the coating method, contacting the surface of the agricultural product includes spraying the mixture onto the surface of the agricultural product. For example, the mixture can be sprayed by a commercially available sprayer. In some embodiments, the mixture is sprayed onto the surface of the agricultural product in the form of an aerosol. In some embodiments of the coating method, contacting the surface of the agricultural product includes dipping the agricultural product in the mixture. In other embodiments of the coating method, the mixture can be brushed, dripped, drop-casted, rolled, patted or poured onto the surface of the agricultural product.

[0305] In some embodiments of the coating method, removing at least a portion of the solvent comprises evaporating at least a portion of the solvent. In some embodiments, evaporation can be passive. In other embodiments, evaporation can be active, for example, as in convection drying. In some embodiments of the coating method, the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, ether, methyl tert-butyl ether or its any combination. In some embodiments of the coating method, the solvent comprises water, ethanol or its combination.

[0306] In some embodiments of the coating method, the concentration of the coating material in the mixture is about 1 mg / mL to about 200 mg / mL, about 1 mg / mL to about 150 mg / mL, about 1 mg / mL to about 125 mg / mL, about 1 mg / mL to about 100 mg / mL, about 25 mg / mL to about 200 mg / mL, about 25 mg / mL to about 150 mg / mL, about 25 mg / mL to about 125 mg / mL, about 25 mg / mL to about 100 mg / mL, about 50 mg / mL to about 200 mg / mL, about 50 mg / mL to about 150 mg / mL, about 50 mg / mL to about 125 mg / mL, or about 50 mg / mL to about 100 mg / mL.

[0307] In some embodiments of the coating method, the coating material includes an inorganic salt as described herein, and the inorganic salt is present in the mixture at a concentration of about 1 ppm to about 1,000 ppm, about 1 ppm to about 500 ppm, about 1 ppm to about 250, about 25 ppm to about 1,000 ppm, about 25 ppm to about 500 ppm, about 25 ppm to about 250 ppm, about 50 ppm to about 1,000 ppm, about 50 ppm to about 500 ppm, about 50 ppm to about 250 ppm.

[0308] In some embodiments of the coating method, the total content of the one or more monoglycerides is about 70% to about 99% by weight, or about 80% to about 98% by weight of the coating material, the total content of the one or more salts is about 1% to about 10% by weight, or about 2% to about 10% by weight of the coating material, and the total content of the one or more zwitterions is about 1% to about 10% by weight of the coating material. In some embodiments of the coating method, the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is about 100:1 to about 4:1, about 100:1 to about 6:1, or about 50:1 to about 8:1, and the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is about 10:1 to about 1:10 or about 1:1 to about 1:10. In some embodiments, the monoglyceride includes a compound of Formula Ii, Formula I-ii, Formula IA-i, or Formula IA-ii described herein. In some embodiments, the salt comprises a compound of Formula II or Formula IIA described herein. In some embodiments, the zwitterion comprises a compound of Formula III-i, Formula III-ii, Formula IIIA-i, Formula IIIA-ii or Formula IV described herein.

[0309] In some embodiments of the coating method, the one or more monoglycerides, one or more salts, and one or more zwitterions account for at least about 80% by weight of the coating material, for example, at least about 85% by weight, at least about 90% by weight, at least about 95% by weight, at least about 97.5% by weight, at least about 98% by weight, or at least about 99% by weight of the coating material. In some embodiments, the coating material and solvent account for at least about 95% by weight of the mixture, for example, at least about 97.5% by weight, at least about 98% by weight, at least about 99% by weight, at least about 99.5% by weight, or at least about 99.9% by weight.

[0310] In some embodiments of the coating method, the coating material includes lecithin or hydrolyzed lecithin, and the lecithin or hydrolyzed lecithin includes at least one of the zwitterions. For example, in some embodiments of the coating method, the coating material includes about 1% to about 10% by weight, about 1% to about 8% by weight, about 1% to about 6% by weight, about 2% to about 10% by weight, about 2% to about 8% by weight, about 2% to about 6% by weight, about 4% to about 10% by weight, about 4% to about 8% by weight, or about 4% to about 6% by weight of lecithin, hydrolyzed lecithin, or a combination thereof. In some embodiments of the coating method, at least one of the zwitterions includes a positively charged group, including a quaternary ammonium group or a phosphonium group, such as a quaternary ammonium group, and a negatively charged group, including a phosphate group, a sulfonate group, or a carboxylate group. In some embodiments of the coating method, at least one of the zwitterions comprises betaine, phosphatidylcholine, lysophosphatidylcholine, phosphatidylserine, lysophosphatidylserine, hydroxysulfobetaine, or amphoacetate. Example

[0311] Example 1. Coated citrus

[0312] Coating material A and coating material B having the compositions shown in Table 1 were prepared.

[0313] Table 1. Coating material composition

[0314] A B Glyceryl Monostearate* 95% by weight 95% by weight Sodium stearate 5 wt% 4 wt% Cocoamidopropyl Betaine - 1% by weight

[0315] *Equilibrium mixture of 2,3-dihydroxyprop-1-yl octadecanoate and 1,3-dihydroxyprop-2-yl octadecanoate (molar ratio of about 90:10)

[0316] Mixture 1, Mixture 2, and Mixture 3 of coating material A and coating material B dispersed in water at the concentrations shown in Table 2 were prepared. For each of Mixture 1, Mixture 2, and Mixture 3, 120 unwaxed citrus fruits of the same size, mass, maturity, packaging date, and orchard were coated by dipping each citrus into a bowl of the mixture and then drying in a rolling translation heat tunnel at 65–70°C for 100 seconds. The mass loss of the coated citrus and the uncoated citrus control group was then measured. The results are shown in Table 2.

[0317] Table 2. Composition of mixture and mass loss of citrus

[0318] Coating materials concentration Mass loss multiple* Mixture 1 A 50 g / L 1.42 Mixture 2 B 50 g / L 1.62 Mixture 3 B 100 g / L 1.83 Untreated - - 1

[0319] *Ratio of the average mass loss rate of the untreated control to the average mass loss rate of the corresponding tested agricultural product over a given period of time

[0320] As shown in Table 2, coatings formed from coating materials comprising fatty acid salts and zwitterions reduced mass loss of the produce better than coatings lacking zwitterions.

[0321] Example 2. Coated citrus

[0322] Coating material C and coating material D having the compositions shown in Table 3 were prepared.

[0323] Table 3. Coating material composition

[0324] C D Glyceryl Monostearate 94.8% by weight 94.8% by weight Sodium stearate 5 wt% 4 wt% Cocoamidopropyl Betaine - 1% by weight Sodium chloride 0.2 wt% 0.2 wt%

[0325] Mixtures 4-7 of coating material A, coating material C, and coating material D dispersed in water at the concentrations shown in Table 4 were prepared. For each of mixtures 4-7, groups of 120 unwaxed citrus of the same size, mass, maturity, packaging date, and orchard were coated by dipping each citrus into a bowl of the mixture and then drying in a rolling translational heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated citrus and a control group of uncoated citrus were then measured. The results are shown in Table 4.

[0326] Table 4. Composition of mixture and mass loss of citrus

[0327] Coating materials concentration Quality loss multiple Mixture 4 A 50 g / L 1.90 Mixture 5 C 50.1 g / L 1.95 Mixture 6 C 100.2 g / L 2.60 Mixture 7 D 100.2 g / L 3.27 Untreated - - 1

[0328] As shown in Table 4, coatings formed from coating materials comprising fatty acid salts, zwitterions, and inorganic salts reduced mass loss of produce better than coatings lacking zwitterions and / or inorganic salts.

[0329] Example 3. Viscoelastic properties of dispersions

[0330] Coating material E and coating material F having the compositions shown in Table 5 were prepared.

[0331] Table 5. Coating material composition

[0332] E F Glyceryl Monostearate 94.97% by weight 94.92% by weight Sodium stearate 5 wt% 5 wt% Sodium chloride 0.03 wt% 0.08 wt%

[0333] Mixtures 8-10 of coating material A, coating material E, and coating material F dispersed in water at the concentrations shown in Table 6 were prepared.

[0334] Table 6. Mixture composition

[0335] mixture Coating materials concentration 8 A 60 g / L 9 E 60 g / L 10 F 60 g / L

[0336] The storage modulus G' and loss modulus G" of each of the mixtures 8-10 were measured as a function of angular frequency (rad / s) using the solution scanned at 55°C with an oscillating strain of 0.2%. The results are shown in FIG. Figure 1 as shown in .

[0337] Mixture 10 appears to be a viscoelastic fluid, while mixture 8 appears to be a gel. Figure 1 As shown in , this change in viscoelasticity as a function of NaCl concentration can provide improved mixing and enable higher concentrations of the coating material to be achieved.

[0338] Example 4. Coated citrus

[0339] Coating materials GJ having the compositions shown in Table 7 were prepared.

[0340] Table 7. Coating material composition

[0341] G H I J Glyceryl Monostearate 95% by weight 95% by weight 95% by weight 95% by weight Sodium stearate 2 wt% 2 wt% 2 wt% 2 wt% Phosphatidylcholine* 3 wt% - - - Lysophosphatidylcholine - 3 wt% - - Lecithin - - 3 wt% Lysolecithin - - - 3 wt%

[0342] * (Lipoid LLC, Newark, NJ)

[0343] Mixtures 11–15 of coating material A and coating materials G–J dispersed in water at the concentrations shown in Table 8 were prepared. For each of mixtures 11–15, groups of 120 unwaxed citrus of identical size, mass, maturity, packaging date, and orchard were coated by dipping each citrus into a bowl of the mixture and then drying in a rolling translational heat tunnel at 65–70°C for 100 seconds. The mass loss of the coated citrus and a control group of uncoated citrus were then measured. The results are shown in Table 8.

[0344] Table 8. Composition of mixture and mass loss of citrus

[0345] Coating materials concentration Quality loss multiple Mixture 11 A 50 g / L 2.83 Mixture 12 G 50 g / L 3.10 Mixture 13 H 50 g / L 3.57 Mixture 14 I 50 g / L 3.21 Mixture 15 J 50 g / L 3.70 Untreated - - 1

[0346] As shown in Table 8, coatings formed from coating materials comprising fatty acid salts and zwitterions reduced mass loss of the produce better than coatings lacking zwitterions.

[0347] Example 5. Coated Avocado

[0348] Coating material KM having the composition shown in Table 9 was prepared.

[0349] Table 9. Coating material composition

[0350] K L M Glyceryl Monostearate 95% by weight 95% by weight 95% by weight Sodium stearate 4 wt% 2.5 wt% 1% by weight Phosphatidylcholine 1% by weight 2.5 wt% 4 wt%

[0351] Mixtures 16-19 of coating material A and coating materials K-M dispersed in water at the concentrations shown in Table 10 were prepared. For each of mixtures 16-19, groups of 120 California avocados of identical size, mass, maturity, packaging date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying in a rolling translational heat tunnel at 65-70°C for 100 seconds. The mass loss and respiration production of the coated avocados and a control group of uncoated avocados were then measured. The results are shown in Tables 10 and Figure 2 as shown in .

[0352] Table 10. Mixture composition, mass loss of avocado

[0353] Coating materials concentration Quality loss multiple Mixture 16 A 30 g / L 1.41 Mixture 17 K 30 g / L 1.49 Mixture 18 L 30 g / L 1.68 Mixture 19 M 30 g / L 1.90 Untreated - - 1

[0354] As shown in Table 10 and Figure 2 As shown in , coatings formed from coating materials comprising increasing proportions of zwitterionic fatty acid salts better reduce mass loss and respiration of produce.

[0355] Example 6. Coated Avocado

[0356] Mixtures 20-25 of coating material A and coating material J dispersed in water at the concentrations shown in Table 11 were prepared. For each of mixtures 20-25, groups of 120 California avocados of identical size, mass, maturity, packaging date, and orchard were coated by spraying the solution onto each avocado on a brush bed and then drying in a rolling translational heat tunnel at 65-70°C for 100 seconds. The mass loss and respiration production of the coated avocados and a control group of uncoated avocados were then measured. The results are shown in Tables 11 and Figure 3 as shown in .

[0357] Table 11. Mixture composition, mass loss of avocado

[0358] Coating materials concentration Quality loss multiple Mixture 20 A 15 g / L 1.65 Mixture 21 A 30 g / L 1.99 Mixture 22 A 45 g / L 2.26 Mixture 23 J 15 g / L 1.87 Mixture 24 J 30 g / L 2.40 Mixture 25 J 45 g / L 2.69 Untreated - - 1

[0359] As shown in Table 11 and Figure 3 As shown in , a coating formed from a coating material comprising 3 wt % lysolecithin, applied over a range of coating material concentrations, reduces mass loss and respiration of the produce.

[0360] Example 7. Coated lime

[0361] Coating material NR having the composition shown in Table 12 was prepared.

[0362] Table 12. Coating material composition

[0363] N O P Q R Glyceryl Monostearate 91.2% by weight 91.2% by weight 91.2% by weight 92.4% by weight 92.4% by weight Glyceryl Monolaurate* 4 wt% 4 wt% 4 wt% 2.7 wt% 2.7 wt% Sodium stearate 4.8 wt% 1.9 wt% 1.9 wt% 4.9 wt% 2 wt% Lysolecithin - 2.9 wt% - - 2.9 wt% Lysophosphatidylcholine - - 2.9 wt% - -

[0364] *Equilibrium mixture of 2,3-dihydroxyprop-1-yl dodecanoate and 1,3-dihydroxyprop-2-yl dodecanoate (molar ratio of about 90:10)

[0365] Mixtures 26-33 of coating material A, coating material J, and coating materials N-R dispersed in water at the concentrations shown in Table 13 were prepared. For each of mixtures 26-33, groups of 120 limes of identical size, mass, maturity, packaging date, and orchard were coated by dipping each lime into a bowl of the mixture and then drying in a rolling translation heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated limes and a control group of uncoated limes was then measured. The results are shown in Table 13.

[0366] Table 13. Mixture composition, mass loss of lime

[0367]

[0368]

[0369] As shown in Table 13, the coating formed of the coating material comprising fatty acid salt, zwitterion and monolaurin better reduced the mass loss and respiration generation of the produce.

[0370] Example 8. Coated tangerines

[0371] Coating materials SU having the compositions shown in Table 14 were prepared.

[0372] Table 14. Coating material composition

[0373] S T U Glyceryl Monostearate 95% by weight 90% by weight 85% by weight Sodium stearate 3 wt% 5 wt% 5 wt% Lysolecithin 2 wt% 5 wt% 10% by weight

[0374] Mixtures 34-38 of coating material A, coating material J, and coating materials S-U dispersed in water at the concentrations shown in Table 15 were prepared. For each of mixtures 34-38, groups of 120 unwaxed mandarins of the same size, mass, maturity, packaging date, and orchard were coated by dipping each mandarin into a bowl of the mixture and then drying in a rolling translation heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated mandarins and the uncoated mandarin control group was then measured. The results are shown in Table 15.

[0375] Table 15. Mixture composition and mass loss of red mandarin oranges

[0376]

[0377]

[0378] As shown in Table 15, for a given ratio of fatty acid salt to zwitterionic monoglyceride, coatings formed from coating materials including increasing ratios of zwitterionic fatty acid salt better reduced mass loss and respiration of the produce.

[0379] Although the present disclosure contains many specific implementation details, these details should not be interpreted as limitations on the scope of the subject matter or the scope that can be claimed, but should be interpreted as descriptions of features that may be specific to a particular implementation. Certain features described in the context of separate embodiments in the present disclosure may also be implemented in combination in a single embodiment. Conversely, the various features described in the context of a single embodiment may also be implemented individually or in any suitable sub-combination in multiple embodiments. In addition, although the previously described features may be described as working in certain combinations and even initially claimed as such, in some cases, one or more features in the combination may be deleted from the claimed combination, and the claimed combination may involve sub-combinations or variations of sub-combinations.

[0380] Specific embodiments of the subject matter have been described. Other embodiments, variations and permutations of the described embodiments will be apparent to those skilled in the art and are within the scope of the following claims. Although operations are described in a particular order in the drawings or claims, this should not be understood as requiring that the operations be performed in the particular order shown or in sequential order, or that all illustrated operations (some operations may be deemed optional) be performed to achieve the desired results.

[0381] Therefore, the example embodiments described above do not define or limit the present disclosure. Other changes, substitutions, and alterations are also possible without departing from the spirit and scope of the present disclosure.

Claims

1. A composition comprising: One or more C 4 -C 28 Monoglycerides of fatty acids are present in a total amount of from about 40% to about 99% by weight of the composition. One or more C 4 -C 28 Salts of fatty acids present in a total amount of from about 0.1% to about 20% by weight of the composition; and One or more zwitterions are present in a total amount of 0.1% to about 20% by weight of the composition.

2. The composition of claim 1, wherein the one or more monoglycerides are present in an amount of about 70% to about 99% by weight.

3. The composition of claim 1, wherein the one or more monoglycerides are present in an amount of about 80% to about 98% by weight.

4. The composition of any one of claims 1-3, wherein the total amount of the one or more salts is from about 1% to about 10% by weight of the composition.

5. The composition of any one of claims 1-3, wherein the total amount of the one or more salts is from about 2% to about 10% by weight of the composition.

6. The composition of any one of claims 1-5, wherein the one or more zwitterions are present in a total amount of about 1% to about 10% by weight of the composition.

7. The composition of any one of claims 1-5, wherein the one or more zwitterions are present in a total amount of about 2% to about 10% by weight of the composition.

8. The composition of any one of claims 1 to 7, further comprising an inorganic salt.

9. The composition of claim 8, wherein the one or more inorganic salts comprises sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any combination thereof.

10. A composition comprising: One or more C 4 –C 28 Monoglycerides of fatty acids; One or more C 4 –C 28 Salts of fatty acids; and one or more zwitterions; wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:

1.

11. The composition of claim 10, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 6:

1.

12. The composition of claim 10, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 50:1 to about 8:

1.

13. The composition of any one of claims 10-12, wherein the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 10:1 to about 1:

10.

14. The composition of any one of claims 10-12, wherein the ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 1:1 to about 1:

10.

15. The composition of any one of claims 10-14, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions comprise at least about 80 wt% of the composition.

16. The composition of any one of claims 1 to 15, wherein the composition comprises lecithin or hydrolyzed lecithin containing at least one of the zwitterions.

17. The composition of any one of claims 1 to 16, wherein at least one of the zwitterions include: Positively charged groups, including quaternary ammonium groups or phosphonium groups; as well as Negatively charged groups include phosphate groups, sulfonate groups or carboxylate groups.

18. The composition of any one of claims 1-16, wherein at least one of the zwitterions comprises betaine, phosphatidylcholine, lysophosphatidylcholine, hydroxysulfobetaine, or amphoacetate.

19. The composition of any one of claims 1-18, wherein at least one of the zwitterions comprises a compound of formula III-i or formula III-ii: in: R B1 , R B2 and R B3 Each independently selected from C 1 –C 22 Alkyl and (C 1 –C 6 Alkyl)-NR B4 C(O)R H ; Each occurrence of R B4 are independently H or C 1 –C 6 alkyl; and Each occurrence of R H Independently for C 3 –C 21 Sidechain.

20. The composition of claim 19, wherein R B1 and R B2 Each is C 1 -C 6 alkyl.

21. The composition of claim 19 or claim 20, wherein R B3 C 10 -C 20 alkyl.

22. The composition of any one of claims 1-21, wherein at least one of the zwitterions comprises a compound of Formula IIIA-i or Formula IIIA-ii: in: R B1 and R B2 Each independently selected from C 1 –C 6 alkyl; R B4 H or C 1 –C 6 alkyl; and R H C 3 –C 21 Sidechain.

23. The composition of claim 22, wherein R B4 It's H.

24. The composition of any one of claims 1-23, wherein at least one of the zwitterions comprises a compound of formula IV: in: R C1 , R C2 and R C3 Each independently selected from C 1 –C 6 alkyl; R C4 and R C5 are each independently selected from H and C(O)R H ; Each occurrence of R H Independently for C 3 –C 21 side chains; and R C4 and R C5 at least one of which is not H.

25. The composition of claim 24, wherein R C4 and R C5 Each is independently C(O)R H .

26. The composition of claim 24 or claim 25, wherein R C4 H and R C5 C(O)R H .

27. The composition of any one of claims 1 to 26, wherein each of the one or more monoglycerides independently comprises a compound of Formula Ii or Formula I-ii: in: R A1 and R A2 Each independently selected from H and C 1 –C 6 Alkyl; and R H C 3 –C 27 Sidechain.

28. The composition of claim 27, wherein R A1 and R A2 Each is H.

29. The composition of claim 27 or claim 28, wherein R H is a saturated, unsubstituted side chain.

30. The composition of any one of claims 27-29, wherein R H It is C 11 -C 21 Sidechain.

31. The composition of any one of claims 1-26, wherein each of the one or more monoglycerides independently comprises a compound of Formula IA-i or Formula IA-ii: in: R A1 and R A2 Each independently selected from H and C 1 –C 6 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy; Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy; R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of the carbon atoms to which they are attached may form a double bond, a 3- to 6-membered heterocycloalkyl or a C 3 –C 6 Cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; and The sum of o and p is 0 to 17.

32. The composition of claim 31, wherein R A1 and R A2 Each is H.

33. The composition of any one of claims 1-32, wherein each of the one or more salts independently comprises a compound of formula II: in: R H C 3 –C 27 side chains; and X n+ It is the cationic part having a formal charge n.

34. The composition of claim 33, wherein X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + ;and Each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C 3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, wherein Each C 1 –C 6 The alkyl group is optionally substituted with 1-3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 heterocycloalkyl, aryl and heteroaryl; and Optionally, one or more R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 Heterocycloalkyl.

35. The composition of claim 33 or claim 34, wherein R H is a saturated, unsubstituted side chain.

36. The composition of any one of claims 1-32, wherein each of the one or more salts independently comprises a compound of Formula IIA: in: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy; Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C 1 –C 6 Alkyl, C 2 –C 6 Alkenyl and C 1 –C 6 Alkoxy; R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A and R 11B Any two of them may form a double bond, a 3- to 6-membered heterocycloalkyl or a C 3 –C 6 Cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is from 0 to 17; and X n+ It is the cationic part having a formal charge n.

37. The composition of claim 36, wherein X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D ) 4 N + ;and Each occurrence of R D Selected from H, C 1 –C 6 Alkyl, C 3 –C 6 Cycloalkyl, C 3 –C 6 Heterocycloalkyl, aryl and heteroaryl, wherein Each C 1 –C 6 The alkyl group is optionally substituted with 1-3 R E Replacement, R E Independently selected from C 3 –C 6 Cycloalkyl, C 3 –C 6 heterocycloalkyl, aryl and heteroaryl; and Optionally, one or more R D Together with the nitrogen atom to which they are attached, they form C 3 –C 6 Heterocycloalkyl.

38. A mixture comprising: The composition of any one of claims 1 to 37; and Solvent.

39. The mixture of claim 38 comprising from about 30% to about 99.9% by weight of the composition.

40. The mixture of claim 38, comprising from about 90% to about 99.5% by weight of the composition.

41. The mixture of any one of claims 38-40, wherein the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof.

42. A coated agricultural product comprising an agricultural product and a layer disposed on a surface of the agricultural product, wherein the layer comprises the composition of any one of claims 1-37.

43. The coated agricultural product of claim 42, wherein the layer is disposed on a stratum corneum surface of the agricultural product.

44. The coated agricultural product of claim 42 or claim 43, wherein the layer has a thickness of about 0.1 microns to about 20 microns.

45. The coated agricultural product of claim 42 or claim 43, wherein the layer has a thickness of about 0.1 microns to about 10 microns.

46. ​​A method of coating agricultural products, the method include: The surface of the agricultural product is contacted with a mixture comprising a coating material and a solvent, wherein the coating material comprises One or more C 4 –C 28 Monoglycerides of fatty acids; One or more C 4 –C 28 Salts of fatty acids; and one or more zwitterions; wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 4:1; and At least a portion of the solvent is removed to form a coating on the surface of the agricultural product.

47. The method of claim 46, wherein the surface is a cuticle surface of the produce.

48. The method of claim 46 or claim 47, wherein contacting the surface include: spraying the mixture onto the surface; or The produce is dipped in the mixture.

49. The method of any one of claims 46-48, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

50. The method of any one of claims 46-49, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

51. The method of any one of claims 46-50, wherein the concentration of the coating material in the mixture is about 1 mg / mL to about 200 mg / mL.

52. The method of any one of claims 46-50, wherein the concentration of the coating material in the mixture is about 50 mg / mL to about 200 mg / mL.

53. The method of any one of claims 46-52, wherein the coating material further comprises one or more inorganic salts.

54. The method of claim 53, wherein the one or more inorganic salts comprises sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any mixture thereof.

55. The method of claim 53 or claim 54, wherein the total amount of the one or more inorganic salts in the mixture has a concentration of about 5 ppm to about 500 ppm calculated on a weight basis.

56. The method of any one of claims 46 to 55, in: The one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the coating material. The total content of the one or more salts is from about 1% to about 10% by weight of the coating material; and The total content of the one or more zwitterions is from about 1% to about 10% by weight of the coating material.

57. The method of any one of claims 46 to 56, in: The ratio of the total moles of the one or more monoglycerides to the total moles of the one or more salts and the one or more zwitterions is from about 100:1 to about 6:1; and The ratio of the total moles of the one or more salts to the total moles of the one or more zwitterions is from about 10:1 to about 1:

10.

58. The method of any one of claims 46-57, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions comprise at least about 80% by weight of the coating material.

59. The method of any one of claims 46-58, wherein the coating material and solvent comprise at least about 95% by weight of the mixture.

60. The method of any one of claims 46-59, wherein the coating material comprises lecithin, hydrolyzed lecithin, or a combination thereof, which comprises at least one of the zwitterions.

61. The method of claim 60, wherein the coating material comprises about 1 wt% to about 10 wt% lecithin, hydrolyzed lecithin, or a combination thereof.

62. The method of any one of claims 46-61, wherein at least one of the zwitterions comprises Positively charged groups, including quaternary ammonium groups or phosphonium groups; and Negatively charged groups include phosphate groups, sulfonate groups or carboxylate groups.

63. The method of any one of claims 46-62, wherein at least one of the zwitterions comprises betaine, phosphatidylcholine, lysophosphatidylcholine, hydroxysulfobetaine, or amphoacetate.

64. A method of coating agricultural products, the method include: contacting the surface of the agricultural product with the mixture of any one of claims 38-41; and At least a portion of the solvent is removed to form a coating on the surface of the agricultural product.

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