Coating compositions containing co-surfactants

Abstract

The present disclosure relates to compositions comprising monoglycerides and co-surfactants. Exemplary embodiments include compositions comprising from about 40% to about 99% by weight of one or more C4-C6 monoglycerides. 28 Monoglycerides of fatty acids, from about 0.1% to about 20% by weight of one or more C4-C 28 salts of fatty acids, and about 0.1% to about 20% by weight of one or more zwitterions.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of priority to U.S. patent application Ser. No. 63 / 401,934, filed Aug. 29, 2022, the contents of which are expressly incorporated herein by reference.

[0002] Technical Field

[0002] The present disclosure relates to coatings for agricultural products. [Background technology]

[0003] background

[0003] Common agricultural products are susceptible to decomposition and spoilage (i.e., spoilage) when exposed to the environment. Such agricultural products can include, for example, eggs, fruits, vegetables, crops, seeds, nuts, flowers, and / or whole plants (including their processed and semi-processed forms). Non-agricultural products (e.g., vitamins, candy, etc.) are also vulnerable to degradation when exposed to the ambient environment. Decomposition of agricultural products can occur through abiotic means, such as water loss from the exterior surface of the produce through evaporation into the atmosphere, and / or oxidation by oxygen diffusing into the produce from the environment, and / or physical damage to the surface, and / or light-induced degradation (i.e., photolysis). Additionally, biotic stressors, such as bacteria, fungi, viruses, and / or pests, can also infest and decompose agricultural products. Summary of the Invention [Problem to be solved by the invention]

[0004]

[0004] Conventional approaches to preventing decomposition, maintaining quality, and increasing the shelf life of produce include refrigeration and / or special packaging. Refrigeration requires capital-intensive equipment, demands constant energy expenditure, can result in damage or loss of quality to the produce if not carefully controlled, and must be actively managed. Additionally, any interruption in the temperature-controlled supply chain negates the benefits of refrigeration. Special packaging also requires expensive equipment, consumes packaging materials, increases shipping costs, and can require active management. Despite the benefits that refrigeration and special packaging can enable, handling and transporting produce can result in surface abrasions or scratches that are aesthetically unpleasing to consumers and can serve as entry points for bacteria and fungi. Furthermore, the expenses associated with such approaches can increase the cost of the produce. [Means for solving the problem]

[0005] overview

[0005] Provided herein are one or more C4-C6 olefins present in a total amount of about 40% to about 99% by weight of the composition. 28 Monoglycerides of fatty acids, one or more C4-C present in a total amount of 0.1% to about 20% by weight of the composition 28 A composition comprising a salt of a fatty acid and one or more zwitterions present in a total amount of 0.1% to about 20% by weight of the composition.

[0006] Also provided herein are one or more C4 to C 28 Monoglycerides of fatty acids, one or more C4-C 28 A composition comprising a salt of a fatty acid and one or more zwitterions, wherein the ratio of the total number of moles of one or more monoglycerides to the total number of moles of one or more salts and one or more zwitterions is about 100:1 to about 4:1.

[0007] Also provided herein are mixtures of the compositions and solvents described herein.

[0008]

[0008] Also provided herein is a coated agricultural product comprising an agricultural product and a layer disposed on a surface of the agricultural product, the layer comprising a composition described herein.

[0009] Also provided herein is a method of coating agricultural produce, the method comprising contacting the surface of the agricultural produce with a mixture comprising a coating agent and a solvent, removing at least a portion of the solvent, and forming a coating on the surface of the agricultural produce. The coating agent may be one or more C4-C 28 Monoglycerides of fatty acids, one or more C4-C 28 The coating agent comprises a salt of a fatty acid and one or more zwitterions, and 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 one or more zwitterions present in the coating agent is from about 100:1 to about 4:1.

[0010]

[0010] Also provided herein is a method for coating agricultural produce, the method comprising contacting the surface of the agricultural produce with a mixture described herein, removing at least a portion of the solvent, and forming a coating on the surface of the agricultural produce.

[0011]

[0011] The disclosed inventive concept includes those defined in the appended claims, but it should be understood that the inventive concept can also be defined according to the following embodiments.

[0012]

[0012] In addition to the embodiments in the accompanying claims and the embodiments described above, the following numbered embodiments are also innovative.

[0013]

[0013] Embodiment 1 is One or more C4-C6 28 Monoglycerides of fatty acids; One or more C4-C628 Salts of fatty acids; and One or more zwitterions present in a total amount of 0.1% to about 20% by weight of the composition A composition comprising:

[0014]

[0014] Embodiment 2 is the composition of embodiment 1, wherein the one or more monoglycerides are present in a total amount from about 70% to about 99% by weight.

[0015] Embodiment 3 is the composition of embodiment 1, wherein the one or more monoglycerides are present in a total amount from about 80% to about 98% by weight.

[0016]

[0016] Embodiment 4 is the composition of any of Embodiments 1-3, wherein the one or more salts are present in a total amount of about 1% to about 10% by weight of the composition.

[0017]

[0017] Embodiment 5 is the composition of any of embodiments 1-3, wherein the one or more salts are present in a total amount of about 2% to about 10% by weight of the composition.

[0018]

[0018] Embodiment 6 is the composition of any of embodiments 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.

[0019]

[0019] Embodiment 7 is the composition of any of embodiments 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.

[0020]

[0020] Embodiment 8 is the composition of any of embodiments 1-7, further comprising an inorganic salt.

[0021]

[0021] Embodiment 9 is the composition of embodiment 8, wherein the one or more inorganic salts comprise sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any combination thereof.

[0022]

[0022] Embodiment 10 is One or more C4-C 28 Monoglycerides of fatty acids; One or more C4-C 28 Salts of fatty acids; and One or more zwitterions A composition comprising: Here, the ratio of the total number of moles of one or more monoglycerides to the total number of moles of one or more salts and one or more zwitterions is about 100:1 to about 4:1.

[0023]

[0023] Embodiment 11 is a composition of embodiment 10, wherein the ratio of the total number of moles of one or more monoglycerides to the total number of moles of one or more salts and one or more zwitterions is about 100:1: to about 6:1.

[0024]

[0024] Embodiment 12 is a composition of embodiment 10, wherein the ratio of the total number of moles of one or more monoglycerides to the total number of moles of one or more salts and one or more zwitterions is about 50:1: to about 8:1.

[0025]

[0025] Embodiment 13 is a composition of any of embodiments 10 to 12, wherein the ratio of the total number of moles of one or more salts to the total number of moles of one or more zwitterions is from about 10:1 to about 1:10.

[0026]

[0026] Embodiment 14 is a composition of any of embodiments 10 to 12, wherein the ratio of the total number of moles of one or more salts to the total number of moles of one or more zwitterions is from about 1:1 to about 1:10.

[0027]

[0027] Embodiment 15 is a composition of any of embodiments 10 to 14, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions constitute at least about 80% by weight of the composition.

[0028]

[0028] Embodiment 16 is the composition of any of embodiments 1-15, wherein the composition comprises a lecithin or hydrolyzed lecithin comprising at least one zwitterion.

[0029] Embodiment 17 is the composition of any of embodiments 1-16, wherein at least one of the zwitterions is: positively charged groups, including quaternary ammonium or phosphonium groups; and Negatively charged groups, including phosphate, sulfonate, or carboxylate groups Includes.

[0030]

[0030] Embodiment 18 is the composition of any of embodiments 1-16, wherein at least one of the zwitterions comprises a betaine, a phosphatidylcholine, a lysophosphatidylcholine, a hydroxysultaine, or an amphoacetate.

[0031] Embodiment 19 is the composition of any of embodiments 1-18, wherein at least one of the zwitterions comprises a compound of Formula III-i or Formula III-ii: [ka] In the formula: R B1 , R B2 , and R B3 is C1~C 22 Alkyl and (C1-C6 alkyl)-NR B4 C(O)R H are each independently selected from R B4 is independently at each occurrence H or C1-C6 alkyl; R H Each time it appears, C3~C 21 It is a side chain.

[0032] Embodiment 20 is the composition of embodiment 19, wherein R B1 and R B2are each C1 to C6 alkyl.

[0033] Embodiment 21 is the composition of embodiment 19 or embodiment 20, wherein R B3 is C 10 ~C 20 It is alkyl.

[0034] Embodiment 22 is the composition of any of embodiments 1-21, wherein at least one of the zwitterions comprises a compound of Formula IIIA-i or Formula IIIA-ii: [ka] During the ceremony: R B1 and R B2 are each independently selected from C1-C6 alkyl; R B4 is H or C1-C6 alkyl; R H is C3~C 21 It is a side chain.

[0035] Embodiment 23 is the composition of embodiment 22, wherein R B4 is H.

[0036] Embodiment 24 is the composition of any of embodiments 1-23, wherein at least one of the zwitterions comprises a compound of formula IV: [ka] During the ceremony: R C1 , R C2 , and R C3 are each independently selected from C1-C6 alkyl; R C4 and R C5 is H and C(O)R H are each independently selected from R H Each time it appears, C3~C 21is a side chain; R C4 and R C5 At least one of them is not H.

[0037] Embodiment 25 is the composition of embodiment 24, wherein R C4 and R C5 are each independently C(O)R H is.

[0038] Embodiment 26 is the composition of embodiment 24 or embodiment 25, wherein R C4 is H and R C5 is C(O)R H is.

[0039] Embodiment 27 is the composition of any of embodiments 1-26, wherein each of the one or more monoglycerides independently comprises a compound of Formula Ii or Formula I-ii: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 It is a side chain.

[0040] Embodiment 28 is the composition of embodiment 27, wherein R A1 and R A2 are H, respectively.

[0041] Embodiment 29 is the composition of embodiment 27 or embodiment 28, wherein R H is a saturated unsubstituted side chain.

[0042] Embodiment 30 is the composition of any of embodiments 27-29, wherein R H is C 11 ~C 21It is a side chain.

[0043] Embodiment 31 is the composition of any of embodiments 1-26, wherein each of the one or more monoglycerides independently comprises a compound of formula IA-i or formula IA-ii: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 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 can be taken together with the carbon atoms to which they are attached to form a double bond, a 3-6 membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17.

[0044] Embodiment 32 is the composition of embodiment 31, wherein R A1 and R A2 are H, respectively.

[0045] Embodiment 33 is the composition of any of embodiments 1-32, wherein each of the one or more salts independently comprises a compound of Formula II: [ka] During the ceremony: R H is C3~C 27 is a side chain; X n+ is a cationic moiety with formal charge n.

[0046] Embodiment 34 is the composition of embodiment 33, wherein: X n+ Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + Selected from; R D each occurrence is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; Each C1-C6 alkyl is selected from 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E is optionally replaced by; Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

[0047] Embodiment 35 is the composition of embodiment 33 or embodiment 34, wherein R H is a saturated unsubstituted side chain.

[0048] Embodiment 36 is the composition of any of embodiments 1-32, wherein each of the one or more salts independently comprises a compound of formula IIA: [ka] During the ceremony: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 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 can be taken together with the carbon atoms to which they are attached to form a double bond, a 3-6 membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17; X n+is a cationic moiety with formal charge n.

[0049] Embodiment 37 is the composition of embodiment 36, wherein: X n+ Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + Selected from; R D each occurrence is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; Each C1-C6 alkyl is selected from 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E is optionally replaced by; Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

[0050]

[0050] Embodiment 38 is The composition of any of embodiments 1 to 37; and It is a mixture containing a solvent.

[0051]

[0051] Embodiment 39 is the mixture of embodiment 38 comprising from about 30% to about 99.9% by weight of the composition.

[0052]

[0052] Embodiment 40 is the mixture of embodiment 38 comprising about 90% to about 99.5% by weight of the composition.

[0053]

[0053] Embodiment 41 is a mixture of any of embodiments 38 to 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.

[0054]

[0054] Embodiment 42 is a coated produce comprising a produce and a layer disposed on a surface of the produce, wherein the layer comprises the composition of any of embodiments 1-37.

[0055] Embodiment 43 is the coated produce of embodiment 42, wherein the layer is disposed on a cuticular surface of the produce.

[0056]

[0056] Embodiment 44 is the coated produce of embodiment 42 or embodiment 43, wherein the layer thickness is from about 0.1 μm to about 20 μm.

[0057] Embodiment 45 is the coated produce of embodiment 42 or embodiment 43, wherein the layer thickness is from about 0.1 μm to about 10 μm.

[0058]

[0058] Embodiment 46 is a method of coating produce, the method comprising: contacting the surface of the produce with a mixture containing a coating agent and a solvent; (The coating agent is One or more C4-C 28 Monoglycerides of fatty acids; One or more C4-C 28 Salts of fatty acids; and One or more zwitterions Includes; 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 one or more zwitterions is from about 100:1 to about 4:1; and removing at least a portion of the solvent to form a coating on the surface of the produce.

[0059]

[0059] Embodiment 47 is the method of embodiment 46, wherein the surface is a cuticular surface of produce.

[0060] Embodiment 48 is the method of embodiment 46 or embodiment 47, wherein contacting the surfaces comprises: spraying the mixture onto a surface; or Immersing produce in the mixture Includes.

[0061] Embodiment 49 is the method of any of embodiments 46-48, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

[0062]

[0062] Embodiment 50 is any of the methods of embodiments 46 to 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.

[0063]

[0063] Embodiment 51 is the method of any of embodiments 46-50, wherein the concentration of the coating agent in the mixture is from about 1 mg / mL to about 200 mg / mL.

[0064]

[0064] Embodiment 52 is the method of any of embodiments 46-50, wherein the concentration of the coating agent in the mixture is from about 50 mg / mL to about 200 mg / mL.

[0065]

[0065] Embodiment 53 is the method of any of embodiments 46-52, wherein the coating agent further comprises one or more inorganic salts.

[0066] Embodiment 54 is the method of embodiment 53, wherein the one or more inorganic salts comprise sodium chloride, potassium chloride, sodium bromide, potassium bromide, or any mixture thereof.

[0067]

[0067] Embodiment 55 is the method of embodiment 53 or embodiment 54, wherein the concentration of the total amount of one or more inorganic salts in the mixture is from about 5 ppm to about 500 ppm, calculated on a weight basis.

[0068] Embodiment 56 is the method of any of embodiments 46-55, wherein: the one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the coating; the one or more salts are present in a total amount of about 1% to about 10% by weight of the coating; The one or more zwitterions are present in a total amount of about 1% to about 10% by weight of the coating.

[0069] Embodiment 57 is the method of any of embodiments 46-56, wherein: 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 one or more zwitterions is from about 100:1 to about 6:1; The ratio of the total number of moles of the one or more salts to the total number of moles of the one or more zwitterions is about 10:1 to about 1:10.

[0070]

[0070] Embodiment 58 is a method of any of embodiments 46 to 57, wherein the one or more monoglycerides, one or more salts, and one or more zwitterions constitute at least about 80% by weight of the coating agent.

[0071]

[0071] Embodiment 59 is the method of any of embodiments 46-58, wherein the coating agent and solvent comprise at least about 95% by weight of the mixture.

[0072]

[0072] Embodiment 60 is the method of any of embodiments 46-59, wherein the coating agent comprises lecithin, hydrolyzed lecithin, or a combination thereof, comprising at least one zwitterion.

[0073]

[0073] Embodiment 61 is the method of embodiment 60, wherein the coating agent comprises about 1% to about 10% by weight of lecithin, hydrolyzed lecithin, or a combination thereof.

[0074] Embodiment 62 is the method of any of embodiments 46-61, wherein at least one of the zwitterions is: positively charged groups, including quaternary ammonium or phosphonium groups; and Negatively charged groups, including phosphate, sulfonate, or carboxylate groups Includes.

[0075]

[0075] Embodiment 63 is the method of any of embodiments 46-62, wherein at least one of the zwitterions comprises a betaine, a phosphatidylcholine, a lysophosphatidylcholine, a hydroxysultaine, or an amphoacetate.

[0076]

[0076] Embodiment 64 is a method of coating produce, the method comprising: contacting a surface of produce with a mixture of any of embodiments 38-41; and removing at least a portion of the solvent to form a coating on the surface of the produce.

[0077] The details of one or more embodiments of the presently disclosed subject matter are set forth in the accompanying drawings and description. Other features, aspects, and advantages of the subject matter will be apparent from the description, drawings, and claims. [Brief explanation of the drawings]

[0078] BRIEF DESCRIPTION OF THE DRAWINGS [Figure 1]

[0078] Figure 1 is a graph illustrating the viscoelastic properties of certain mixtures described herein. [Figure 2]

[0079] 1 is a graph showing the respiration production of California avocados coated with certain compositions described herein. [Figure 3]

[0080] 1 is a graph showing the respiration production of California avocados coated with certain compositions described herein. DETAILED DESCRIPTION OF THE INVENTION

[0079] Detailed Description

[0081] The present disclosure relates to compositions comprising monoglycerides and co-surfactants. In particular, the compositions described herein can be coated onto produce to provide, for example, an improved barrier to gas or water. Such coatings can better limit mass loss and / or CO2 production from produce compared to those lacking the co-surfactant. Furthermore, the solvent mixtures of the compositions described herein can have physical properties suitable for application to produce, for example, by spray coating or dip coating.

[0080]

[0082] Reference will now be made in detail to particular 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.

[0081]

[0083] definition

[0084] The terms "a," "an," and "the" are used herein to include one or more unless the context clearly dictates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise indicated. The statement "at least one of A and B" has the same meaning as "A, B, or A and B." Furthermore, it should be understood that phraseology or terminology used in this disclosure and not otherwise defined is for purposes of description only and not of limitation. The use of section headings is intended to aid in the reading of the document and should not be construed as limiting; information associated with a section heading may appear within or outside that particular section.

[0082]

[0085] Values ​​expressed in range format should be interpreted in an open manner to include not only the numerical values ​​explicitly recited as limits of the range, but also all individual numerical values ​​or subranges subsumed within that range, as if each numerical value and subrange were explicitly recited. 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 recited range. The statement "about X to Y" has the same meaning as "about X to about Y" unless otherwise indicated. Similarly, the statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z" unless otherwise indicated.

[0083]

[0086] As used herein, the term "about" allows for variability in a value or range within 10% of the stated value or stated range limit.

[0084]

[0087] In the methods described herein, acts can be performed in any order, except when a chronological or operational order is explicitly recited. Furthermore, certain acts can be performed concurrently unless express claim language recites them being performed separately. For example, a claimed act of doing X and a claimed act of doing Y can be performed simultaneously in a single operation, and the resulting process would fall within the literary scope of the claimed process.

[0085]

[0088] As used herein, the term "monoglyceride" refers to the condensation product of one glycerol molecule and one fatty acid, i.e., a glycerol group attached to one fatty acid via an ester linkage. Monoglycerides can, but do not necessarily, result from a condensation reaction. For example, monoglycerides can be obtained by an esterification reaction between glycerol and a fatty acid, by transesterification of a triglyceride with glycerol (glycerolysis), etc. Monoglycerides can also be referred to as glyceryl monoalkanoates. When the glycerol group is attached to the ester linkage at the 1-position (e.g., as in 2,3-dihydroxypropan-1-yl octadecanoate), the monoglyceride can be referred to as a 1-monoglyceride or 1-glyceryl alkanoate (e.g., as in 1-glyceryl octadecanoate). When the glycerol group is attached to the ester linkage at the 2-position (e.g., as in 1,3-dihydroxypropan-2-yl hexadecanoate), the monoglyceride can be referred to as a 2-monoglyceride or a 2-glyceryl alkanoate (e.g., as in 2-glyceryl hexadecanoate). The glycerol group of the monoglyceride can be unsubstituted (e.g., as in 2,3-dihydroxypropanon-1-yl alkanoate) or can be further substituted with one or more groups other than fatty acids (e.g., as in 1,3-dialkoxypropan-2-yl alkanoates).

[0086]

[0089] As used herein, the term "fatty acid" refers to a carboxylic acid having an aliphatic side chain. Fatty acids can be naturally occurring or non-naturally occurring, and can contain side chains that are branched or unbranched (e.g., linear), substituted or unsubstituted, and saturated or unsaturated.

[0087]

[0090] As used herein, the term "side chain" refers to the aliphatic portion of a fatty acid, or a portion thereof. Unless otherwise indicated, the side chain of a given fatty acid includes the carbon of the carboxylic acid group. For example, dodecanoic acid is a linear saturated C 12 It can be described as including a side chain, and R H -C(O)OH(wherein, R H is a linear saturated C 11 The side chain can be present in a compound other than a fatty acid, e.g., an ester or amide, and can be, but need not be, derived from a fatty acid. For example, dodecanamide can be described as an amide of a fatty acid, regardless of whether the compound is actually derived from dodecanoic acid.

[0088]

[0091] The term "salt" as used in connection with the disclosed compounds (e.g., fatty acids) refers to derivatives of the compounds in which the compounds are modified by converting an acid or base moiety into their salt form. Examples of such salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines, alkali or organic salts of acidic residues such as carboxylic acids, etc.

[0089]

[0092] When particular features of the compounds described herein are disclosed in groups or ranges, such disclosure includes each and every individual subcombination of the members of such groups and ranges. For example, the term "C1-C6 alkyl" includes (but is not limited to) methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0090]

[0093] As used herein, the term "n-membered" (where n is an integer) typically 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-tetrahydro-naphthalene is an example of a 10-membered cycloalkyl group.

[0091]

[0094] As used herein, the term "substituted" means that an atom or group of atoms formally replaces hydrogen as a "substituent" attached to another group. "Substituted" refers to any level of substitution, e.g., mono-, di-, tri-, tetra-, or penta-substitution, unless otherwise indicated, where such substitution is permitted. Substituents are independently selected, and substitution can be at any chemically accessible position. Substitution at a given atom is limited by valency. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent, e.g., oxo, can replace two hydrogen atoms.

[0092]

[0095] As used herein, the term "C n ~C m " indicates an inclusive range, where n and m are integers and indicate the number of carbons. Examples include C1-C4, C1-C6, etc.

[0093]

[0096] As used herein, the term "alkyl" refers to a saturated hydrocarbon group which may be straight-chained or branched. n ~C m"Alkyl" refers to an alkyl group having n to m carbon atoms. An alkyl group formally corresponds to an alkane with one C-H bond replaced by the point of attachment of the alkyl group to the remainder 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 homologs such as 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, and the like.

[0094]

[0097] As used herein, the term "alkenyl" refers to a straight-chain or branched hydrocarbon group corresponding to an alkyl group having one or more double carbon-carbon bonds. An alkenyl group formally corresponds to an alkene with one C-H bond replaced by the point of attachment of the alkenyl group to the remainder 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.

[0095]

[0098] As used herein, the term "alkoxy" refers to a group of formula -O-alkyl, where the alkyl group is as defined above. n ~C m "Alkoxy" refers to an alkoxy group, the alkyl group of which has n to m carbons. Examples of alkoxy groups include methoxy, ethoxy, propoxy (e.g., n-propoxy and isopropoxy), t-butoxy, and the like.

[0096]

[0099] As used herein, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic, or polycyclic), including cyclic alkyl and alkenyl groups. n ~C m"Cycloalkyl" refers to a cycloalkyl having n to m ring carbon atoms. Cycloalkyl groups can include fused, bridged and / or spiro bicyclic or polycyclic ring systems. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcarnyl, bicyclo[1.1.0]butanyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.0]pentanyl, bicyclo[2.2.0]hexanyl, bicyclo[3.1.0]hexanyl, bicyclo[3.2.0]heptanyl, and bicyclo[3.3.0]octanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.1]heptanyl, and bicyclo[1.1.1]pentanyl.

[0097]

[0100] As used herein, 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 having at least one heteroatom ring member independently selected from nitrogen, sulfur, oxygen, and phosphorus. The term "nm- to m-membered heterocycloalkyl" refers to a heterocycloalkyl having nm to m ring-forming atoms. Ring-forming carbon atoms and heteroatoms of a heterocycloalkyl group can be optionally oxidized to form oxo or sulfido groups or other oxidized linkages (e.g., C(O), S(O), C(S), S(O), N-oxide, etc.), or the nitrogen atom can be quaternized. A heterocycloalkyl group can be attached via a ring-forming carbon atom or ring-forming heteroatom. A heterocycloalkyl group can contain double bonds, for example, up to three double bonds. Examples of heterocycloalkyl groups include, but are not limited to, azetidinyl, dihydrofuranyl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrofuranyl, tetrahydrotriazinyl, tetrahydropyrazolyl, tetrahydrooxazinyl, tetrahydropyrimidinyl, octahydrobenzofuranyl, octahydrobenzimidazolyl, octahydrobenzothiazolyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydropyranyl, tetrahydrothiazinyl, tetrahydrothiadiazinyl, tetrahydro- oxazolyl, morpholinyl, oxetanyl, dioxetanyl, dioxolanyl, dioxanyl, oxapanyl, dioxapanyl, oxacanyl, dioxacanyl, tetrahydrodiazinyl, oxazinyl, oxathiazinyl, quinuclidinyl, chromanyl, isochromanyl, dihydrobenzodioxinyl, benzodioxolyl, benzoxazinyl, indolinyl, dihydrobenzofuranyl, tetrahydroquinolyl, isochromyl, dihydro-1H-isoindolyl, 2-azabicyclo[2.2.1]heptanonyl, 3-azabicyclo[3.1.0]hexanyl, 3-azabicyclo[4.1.0]heptanyl, and the like.Further examples of heterocycloalkyl groups 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, and the like. yl, 1,4-oxazepan-1-yl, isothiazolidinyl, 1,3-thiazolidin-3-yl, 1,2-pyrazolidin-2-yl, 1,2-tetrahydrothiazin-2-yl, 1,3-thiazinan-3-yl, 1,2-tetrahydrodiazin-2-yl, 1,3-tetrahydrodiazin-1-yl, 1,4-oxazin-4-yl, oxazolidinonyl, 2-oxo-piperidinyl (e.g., 2-oxo-piperidin-1-yl), and the like.

[0098]

[0101] composition

[0102] Provided herein are one or more C4-C 28 Monoglycerides of fatty acids, one or more C4-C 28 A composition comprising a salt of a fatty acid and one or more zwitterions. As described herein, the zwitterionic compound (e.g., in conjunction with the fatty acid salt) can act as a co-surfactant to reduce the difference in surface energy between the suspension, colloid, or solution and the solid surface on which the suspension, colloid, or solution is disposed.

[0099]

[0103] In some embodiments, the one or more monoglycerides are present in a total amount of about 40% to about 99% by weight of the composition, e.g., about 40% to about 98% by weight, about 40% to about 96% by weight, about 70% to about 99% by weight, about 70% to about 98% by weight, about 70% to about 96% by weight, about 80% to about 99% by weight, about 80% to about 98% by weight, or about 80% to about 96% by weight of the composition. In some embodiments, the one or more salts are present in a total amount of about 0.1% to about 20% by weight of the composition, e.g., about 0.1% to about 15%, about 0.1% to about 10%, about 1% to about 20%, about 1% to about 15%, about 1% to about 10%, about 2% to about 20%, about 2% to about 15%, or about 2% to about 10% by weight of the composition. In some embodiments, the one or more zwitterions are present in a total amount of about 0.1% to about 20% by weight of the composition, e.g., about 0.1% to about 15% by weight, about 0.1% to about 10% by weight, about 1% to about 20% by weight, about 1% to about 15% by weight, about 1% to about 10% by weight, about 2% to about 20% by weight, about 2% to about 15% by weight, or about 2% to about 10% by weight of the composition.

[0100]

[0104] In some embodiments, the composition further comprises an inorganic salt. In some embodiments, the composition comprises up to about 1 wt. % of the inorganic salt, e.g., about 0.01 wt. % to about 1 wt. %, about 0.01 wt. % to about 0.75 wt. %, about 0.01 wt. % to about 0.5 wt. %, about 0.05 wt. % to about 1 wt. %, about 0.05 wt. % to about 0.75 wt. %, about 0.05 wt. % to about 0.5 wt. %, about 0.1 wt. % to about 1 wt. %, about 0.1 wt. % to about 0.75 wt. %, or 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.

[0101]

[0105] 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 one or more zwitterions is an amount of 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.

[0102]

[0106] In some embodiments, the ratio of the total number of moles of the one or more salts to the total number of 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.

[0103]

[0107] 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.

[0104]

[0108] C4~C 28 Monoglycerides of fatty acids

[0109] The compositions described herein may comprise one or more C4-C 28 In some embodiments, the composition comprises one C4-C monoglyceride of a fatty acid. 28 In some embodiments, the composition comprises two, three, or more C4-C6 monoglycerides of fatty acids. 28 Monoglycerides of fatty acids, e.g., two C4-C 28 Monoglycerides of Fatty Acids In some embodiments, the monoglyceride comprises one or more monoglycerides of naturally occurring fatty acids.

[0105]

[0110] The monoglycerides can 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-dihydroxypropan-1-yl esters of fatty acids, one or more 1,3-dihydroxypropan-2-yl esters of fatty acids, or mixtures thereof. In some embodiments, the 1-monoglycerides constitute at least about 50%, at least about 60%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95%, or about 100% by weight of the monoglycerides present in the composition. In some embodiments, the 1-monoglyceride comprises about 70% to about 100% by weight, about 70% to about 95% by weight, about 70% to about 90% by weight, about 75% to about 100% by weight, about 75% to about 95% by weight, about 75% to about 90% by weight, about 80% to about 100% by weight, about 80% to about 95% by weight, or about 80% to about 90% by weight of the monoglycerides present in the composition.

[0106]

[0111] In some embodiments, the monoglyceride is a C6-C 28 fatty acids, C8~C 28 Fatty acids, C4~C 24 Fatty acids, C6~C 24 fatty acids, C 12 ~C 24 Fatty acids, C4~C 22 Fatty acids, C6~C 22 Fatty acids, or C 12 ~C 22 In some embodiments, one or more of the monoglycerides comprises one or more monoglycerides of fatty acids. In some embodiments, one or more of the monoglycerides comprises an unsubstituted side chain, e.g., an unsubstituted C 12 ~C 22 In some embodiments, one or more of the monoglycerides comprises a linear side chain, e.g., a linear C 12 ~C 22 In some embodiments, one or more of the monoglycerides comprises a saturated side chain, e.g., a saturated C 12 ~C 22Contains side chains.

[0107]

[0112] In some embodiments, the monoglyceride comprises one or more compounds of formula Ii: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 It is a side chain.

[0108]

[0113] In some embodiments, the monoglyceride comprises one or more compounds of formula I-ii: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 It is a side chain.

[0109]

[0114] 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 are each 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 is C5~C 17 In some embodiments of Formula Ii or Formula I-ii, R H is C 11 ~C 21It is a side chain.

[0110]

[0115] In some embodiments, the monoglyceride comprises one or more compounds of formula IA-i: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 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 can be taken together with the carbon atoms to which they are attached to form a double bond, a 3-6 membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17.

[0111]

[0116] In some embodiments, the monoglyceride comprises one or more compounds of formula IA-ii: [ka] During the ceremony: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 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 can be taken together with the carbon atoms to which they are attached to form a double bond, a 3-6 membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17.

[0112]

[0117] In some embodiments, each of the one or more monoglycerides independently comprises 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, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 occurs for each occurrence, and R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H and OH. In some embodiments of Formula IA-i or Formula IA-ii, 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 In some embodiments of Formula IA-i or Formula IA-ii, any two of R on adjacent carbon atoms together form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 Two pairs, one pair, or none of R 10A , R 10B , R 11A , and R 11B Each occurrence of R, together with the carbon atom to which it is attached, forms a double bond. In some embodiments of Formula IA-i or Formula IA-ii, R on adjacent carbon atoms 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 A pair or none of and R 10A , R 10B , R 11A , and R 11B Each occurrence of R, together with the carbon atom to which they are attached, forms an oxirane. 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 above, as well as R 10A , R 10B , R 11A , and R 11B Each occurrence of is OH.

[0113]

[0118] 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.

[0114]

[0119] In some embodiments, the monoglyceride is selected from the group consisting 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 or docosanoic acid, 9-hydroxyhexadecanoic acid, 10-hydroxyhexadecanoic acid, 9,10-dihydroxyhexadecanoic acid, 16-hydroxyhexadecanoic acid, 17-hydroxyhexadecanoic acid, 18-hydroxyhexadecanoic acid, 19-hydroxyhexadecanoic acid, 20-hydroxyhexadecanoic acid, 21-hydroxyhexadecanoic acid, 22-hydroxyhexadecanoic acid, 23-hydroxyhexadecanoic acid, 24-hydroxyhexadecanoic acid, 25-hydroxyhexadecanoic acid, 26-hydroxyhexadecanoic acid, 27-hydroxyhexadecanoic acid, 28-hydroxyhexadecanoic acid, 29-hydroxyhexadecanoic acid, 30-hydroxyhexadecanoic acid, 31-hydroxyhexadecanoic acid, 32-hydroxyhexadecanoic acid, 33-hydroxyhexadecanoic acid, 34-hydroxyhexadecanoic acid, 35-hydroxyhexadecanoic acid, 36-hydroxyhexadecanoic acid, 37-hydroxyhexadecanoic acid, 38-hydroxyhexadecanoic acid, 39-hydroxyhexadecanoic acid, 40-hydroxyhexadecanoic acid, 41-hydroxyhexadecanoic acid, 42-hydroxyhexadecanoic acid, 43-hydroxyhexadecanoic acid, 44-hydroxyhexadecanoic acid, Decanoic 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)-hexadeca-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- Include one or more 1- or 2-monoglycerides of 9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, 18-hydroxy-(9E)-octadec-9-enoic acid, (13Z)-docosa-13-enoic acid, or (13E)-docosa-13-enoic acid, such as 2,3-dihydroxypropan-1-yl ester or 1,3-dihydroxypropan-2-yl ester.

[0115]

[0120] C4~C 28 Salts of fatty acids

[0121] The compositions described herein may comprise one or more C4-C 28 In some embodiments, the composition comprises a salt of a fatty acid. 28 In some embodiments, the composition comprises two, three, or more C4-C6 fatty acid salts.28 Salts of fatty acids, e.g., two C4-C 28 Salts of Fatty Acids In some embodiments, the salts comprise one or more salts of naturally occurring fatty acids.

[0116]

[0122] In some embodiments, the salt is a C-C 28 fatty acids, C8~C 28 Fatty acids, C4~C 24 Fatty acids, C6~C 24 fatty acids, C 12 ~C 24 Fatty acids, C4~C 22 Fatty acids, C6~C 22 Fatty acids, or C 12 ~C 22 In some embodiments, one or more of the salts comprises a fatty acid having an unsubstituted side chain, e.g., an unsubstituted C 12 ~C 22 In some embodiments, one or more of the salts comprises a linear side chain, e.g., a linear C 12 ~C 22 In some embodiments, one or more of the salts comprises a saturated side chain, e.g., a saturated C 12 ~C 22 Contains side chains.

[0117]

[0123] In some embodiments, the salt comprises one or more compounds of formula II: [ka] During the ceremony: R H is C3~C 27 is a side chain; X n+ is a cationic moiety with formal charge n.

[0118]

[0124] 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+ Li + , Na + , K. + , Cs + , Ag+ , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + where R D each occurrence is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, and each C1-C6 alkyl is followed by 1-3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E In some embodiments, X n+ is (R D )4N + and R D together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, X n+ 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 is C5~C 17 In some embodiments of Formula II, R H is C 11 ~C 21 It is a side chain.

[0119]

[0125] In some embodiments, the salt comprises one or more compounds of formula IIA: [ka] During the ceremony: R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 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 can be taken together with the carbon atoms to which they are attached to form a double bond, a 3-6 membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17; X n+ is a cationic moiety with formal charge n.

[0120]

[0126] 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+ Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N +where R D each occurrence is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, and each C1-C6 alkyl is followed by 1-3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E In some embodiments, X n+ is (R D )4N + and R D together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, X n+ Na + , K. + , Ca 2+ , Mg 2+ , and Zn 2+ is selected from.

[0121]

[0127] 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 and 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 11BIn some embodiments of Formula IIA, any two of R on adjacent carbon atoms together form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 Two pairs, one pair, or none of R 10A , R 10B , R 11A , and R 11B Each occurrence of R, together with the carbon atom to which it is attached, forms 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 and R 10A , R 10B , R 11A , and R 11B Each occurrence of R, together with the carbon atom to which they are attached, forms an oxirane. 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 Two, one, or none of the above, as well as R 10A , R 10B , R 11A , and R 11B Each occurrence of is OH.

[0122]

[0128] In some embodiments of Formula IIA, the sum of o and p is 0-13, 0-11, 0-9, 0-7, 5-17, 5-13, 5-11, 5-9, 5-7, 7-17, 7-13, 7-11, 7-9, 9-17, 9-13, 9-11, 11-17, or 11-13.

[0123]

[0129] In some embodiments, the salt comprises one or more salts of saturated, straight-chain, unsubstituted fatty acids, such as sodium, potassium, silver, calcium, magnesium, or zinc salts. In some embodiments, the salt comprises one or more salts 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, or docosanoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, or 18-hydroxy-(9E)-octadec-9-enoic acid, such as sodium, potassium, silver, calcium, magnesium, or zinc salts.

[0124]

[0130] Zwitterions

[0131] The compositions described herein comprise one or more zwitterions. In some embodiments, the compositions comprise one zwitterion. In some embodiments, the compositions comprise two, three, or more zwitterions, e.g., 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.

[0125]

[0132] In some embodiments, one or more of the zwitterions comprise a positively charged group, including a quaternary ammonium group or a phosphonium group. In some embodiments, one or more of the zwitterions comprise a negatively charged group, including a phosphate group, a sulfonate group, or a carboxylate group. In some embodiments, one or more of the zwitterions comprise a quaternary ammonium group and a negatively charged group, including a phosphate group, a sulfonate group, or a carboxylate group.

[0126]

[0133] In some embodiments, the zwitterion comprises betaine, phosphatidylcholine, lysophosphatidylcholine, phosphatidylserine, lysophosphatidylserine, hydroxylsultaine, amphoacetate, or any combination thereof, In some embodiments, the betaine, phosphatidylcholine, lysophosphatidylcholine, phosphatidylserine, lysophosphatidylserine, hydroxylsultaine, and amphoacetate constitute at least about 50%, at least about 60%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95% by weight of the zwitterions present in the composition.

[0127]

[0134] In some embodiments, the composition comprises a lecithin or hydrolyzed lecithin comprising one or more zwitterions. In some embodiments, the composition comprises a lecithin or hydrolyzed lecithin (lysolecithin) comprising one or more zwitterionic glycerophospholipids, such as phosphatidylcholine or lysophosphatidylcholine. In some embodiments, the lecithin or hydrolyzed lecithin contains at least about 10% by weight, or at least about 15% by weight, or at least about 20% by weight of zwitterions. In some embodiments, the composition comprises a lecithin, wherein the lecithin comprises from about 15% to about 35% by weight of a zwitterion, such as phosphatidylcholine or phosphatidylserine. In some embodiments, the composition comprises a lysolecithin, wherein the lysolecithin comprises from about 15% to about 35% by weight of a zwitterion, such as lysophosphatidylcholine or lysophosphatidylserine.

[0128]

[0135] In some embodiments, the zwitterion comprises one or more compounds of formula III-i: [ka] During the ceremony: R B1 , R B2 , and R B3 is C1~C 22Alkyl and (C1-C6 alkyl)-NR B4 C(O)R H are each independently selected from R B4 is independently at each occurrence H or C1-C6 alkyl; R H Each time it appears, C3~C 21 It is a side chain.

[0129]

[0136] In some embodiments, the zwitterion comprises one or more compounds of formula III-ii: [ka] During the ceremony: R B1 , R B2 , and R B3 is C1~C 22 Alkyl and (C1-C6 alkyl)-NR B4 C(O)R H are each independently selected from R B4 is independently at each occurrence H or C1-C6 alkyl; R H Each time it appears, C3~C 21 It is a side chain.

[0130]

[0137] In some embodiments of Formula III-i or Formula III-ii, R B1 and R B2 are each C alkyl. In some embodiments of Formula III-i or Formula III-ii, R B3 is C1-C6 alkyl. In some embodiments of Formula III-i or Formula III-ii, R B3 is C 10 ~C 20 In some embodiments of Formula III-i or Formula III-ii, R B3 is (C1-C6 alkyl)-NR B4 C(O)R H and R B4 is H. In some embodiments of Formula III-i or Formula III-ii, RH is C6~C 21 It is a side chain.

[0131]

[0138] In some embodiments, the zwitterion comprises one or more compounds of formula IIIA-i: [ka] During the ceremony: R B1 and R B2 are each independently selected from C1-C6 alkyl; R B4 is H or C1-C6 alkyl; R H is C3~C 21 It is a side chain.

[0132]

[0139] In some embodiments, the zwitterion comprises one or more compounds of formula IIIA-ii: [ka] During the ceremony: R B1 and R B2 are each independently selected from C1-C6 alkyl; R B4 is H or C1-C6 alkyl; R H is C3~C 21 It is a side chain.

[0133]

[0140] In some embodiments of Formula IIIA-i or Formula IIIA-ii, R B1 and R B2 and each is C alkyl. 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 is C6~C 21 It is a side chain.

[0134]

[0141] In some embodiments, the zwitterion comprises one or more compounds of formula IV: [ka] During the ceremony: R C1 , R C2 , and R C3 are each independently selected from C1-C6 alkyl; R C4 and R C5 is H and C(O)R H are each independently selected from Each R H are independently, C3~C 21 is a side chain; R C4 and R C5 At least one of them is not H.

[0135]

[0142] In some embodiments of Formula IV, R C1 , R C2 , and R C3 are each C alkyl. In some embodiments, R C4 is H and R C5 is C(O)R H In some embodiments, R H Each time it appears, it is assigned independently to C6~C 21 It is a side chain.

[0136]

[0143] In some embodiments, the compounds of Formula III-i, Formula III-ii, Formula IIIA-i, Formula IIIA-ii, and Formula IV constitute at least about 50%, at least about 60%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95% by weight of the zwitterions present in the composition.

[0137]

[0144] Further components

[0145] The compositions described herein can 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 can include a direct or indirect food additive or food contact substance approved by the U.S. Food and Drug Administration (FDA), a component that meets FDA regulatory standards for use as a food additive or food contact substance, or a component that is generally recognized as safe (GRAS) by the FDA.

[0138]

[0146] In some embodiments, the compositions described herein may comprise one or more fatty acids, such as C4 to C6 22 In some embodiments, the composition further comprises a fatty acid or an ester thereof, e.g., a C1-C6 alkyl ester thereof. In some embodiments, the composition comprises less than about 10% by weight, e.g., less than about 5% by weight, less than about 2% by weight, less than about 1% by weight, of one or more of: triglycerides, diglycerides, acetylated monoglycerides, lactylated monoglycerides, succinylated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and any salts thereof, or is free of these.

[0139]

[0147] mixture

[0148] Also provided herein is a mixture comprising a composition described herein and a solvent. In some embodiments, the mixture comprises a dispersion of a composition described herein in a solvent. In some embodiments, the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof. In some embodiments, the solvent comprises water, ethanol, or a combination thereof.

[0140]

[0149] In some embodiments, the mixture comprises about 30% to about 99.9%, about 30% to about 99.5%, about 30% to about 99%, about 50% to about 99.9%, about 50% to about 99.5%, about 50% to about 99%, about 90% to about 99.9%, about 90% to about 99.5%, or about 90% to about 99% solvent by weight.

[0141]

[0150] 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.

[0142]

[0151] In some embodiments, the composition comprises an inorganic salt as described herein, wherein the inorganic salt is present in the mixture at a concentration of from about 1 ppm to about 1,000 ppm, from about 1 ppm to about 500 ppm, from about 1 ppm to about 250, from about 25 ppm to about 1,000 ppm, from about 25 ppm to about 500 ppm, from about 25 ppm to about 250 ppm, from about 50 ppm to about 1,000 ppm, from about 50 ppm to about 500 ppm, or from about 50 ppm to about 250 ppm.

[0143]

[0152] coating

[0153] Also provided herein are coated produce comprising produce and a layer formed from the composition described herein disposed on the surface of the produce. In some embodiments, the produce is edible produce, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, crops, meat, eggs, dairy products, seafood, grains, or any other consumable product. In other embodiments, the produce is non-edible produce, including, for example, non-edible flowers, seeds, shoots, stems, leaves, whole plants, etc. In some embodiments, the layer is disposed on the exterior surface (e.g., cuticle surface) of the produce.

[0144]

[0154] In some embodiments, the layer has a thickness of about 0.1 μm to about 20 μm, e.g., about 0.1 μm to about 15 μm, about 0.1 μm to about 10 μm, about 0.5 μm to about 20 μm, about 0.5 μm to about 15 μm, about 0.5 μm to about 10 μm, about 1 μm to about 20 μm, about 1 μm to about 15 μm, or about 1 μm to about 10 μm.

[0145]

[0155] Coating Method

[0156] Also provided herein are methods for coating agricultural produce, the methods comprising contacting the surface of the agricultural produce with a mixture comprising a coating agent and a solvent, removing at least a portion of the solvent, and forming a coating on the surface of the agricultural produce. The coating agent may be one or more C4-C 28 Monoglycerides of fatty acids, one or more C4-C 28 and one or more zwitterions. In some embodiments, the coating agent is a composition described herein. For example, 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 one or more zwitterions is about 100:1 to about 4:1. In some embodiments, the coating agent comprises one or more C4-C6 fatty acid salts present in a total amount of about 40% to about 99% by weight of the coating agent. 28 Monoglycerides of fatty acids, one or more C4-C present in a total amount of 0.1% to about 20% by weight of the composition 28The coating comprises a salt of a fatty acid and one or more zwitterions present in a total amount of from 0.1% to about 20% by weight of the coating.

[0146]

[0157] In some embodiments of the coating method, the produce is edible produce, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, crops, meat, eggs, dairy products, seafood, grains, or any other consumable product. In other embodiments of the coating method, the produce is non-edible produce, including, for example, inedible flowers, seeds, shoots, stems, leaves, whole plants, etc. In some embodiments, the method includes contacting an exterior surface (e.g., cuticle surface) of the produce with a mixture containing a coating agent.

[0147]

[0158] In some embodiments of the coating method, contacting the surface of the produce comprises spraying the mixture onto the surface of the produce. The mixture can be sprayed, for example, from a commercially available sprayer. In some embodiments, the mixture is an aerosol that is sprayed onto the surface of the produce. In some embodiments of the coating method, contacting the surface of the produce comprises dipping the produce in the mixture. In other embodiments of the coating method, the mixture can be brushed, dripped, drop-cast, rolled, pressed, or poured onto the surface of the produce.

[0148]

[0159] 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, the evaporation can be passive. In other embodiments, the evaporation can be active, such as in convective drying. In some embodiments of the coating method, the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof. In some embodiments of the coating method, the solvent comprises water, ethanol, or a combination thereof.

[0149]

[0160] In some embodiments of the coating method, the concentration of the coating agent 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.

[0150]

[0161] In some embodiments of the coating method, the coating agent comprises an inorganic salt as described herein, and the inorganic salt is present in the mixture at a concentration of from about 1 ppm to about 1,000 ppm, from about 1 ppm to about 500 ppm, from about 1 ppm to about 250, from about 25 ppm to about 1,000 ppm, from about 25 ppm to about 500 ppm, from about 25 ppm to about 250 ppm, from about 50 ppm to about 1,000 ppm, from about 50 ppm to about 500 ppm, or from about 50 ppm to about 250 ppm.

[0151]

[0162] In some embodiments of the coating method, the one or more monoglycerides are present in a total amount of about 70% to about 99% or about 80% to about 98% by weight of the coating, the one or more salts are present in a total amount of about 1% to about 10% or about 2% to about 10% by weight of the coating, and the one or more zwitterions are present in a total amount of about 1% to about 10% by weight of the coating. In some embodiments of the coating method, 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, about 100:1 to about 6:1, or about 50:1 to about 8:1, and the ratio of the total number of moles of the one or more salts to the total number of 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 comprises 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.

[0152]

[0163] In some embodiments of the coating method, the one or more monoglycerides, the one or more salts, and the one or more zwitterions comprise at least about 80% by weight of the coating agent, 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 coating agent. In some embodiments, the coating agent and solvent comprise at least about 95% by weight of the mixture, e.g., at least about 97.5%, at least about 98%, at least about 99%, at least about 99.5%, or at least about 99.9% by weight.

[0153]

[0164] In some embodiments of the coating method, the coating agent comprises lecithin or hydrolyzed lecithin, and the lecithin or hydrolyzed lecithin comprises at least one zwitterion. For example, in some embodiments of the coating method, the coating agent comprises about 1% to about 10%, about 1% to about 8%, about 1% to about 6%, about 2% to about 10%, about 2% to about 8%, about 2% to about 6%, about 4% to about 10%, about 4% to about 8%, 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 comprises a positively charged group, including a quaternary ammonium group or a phosphonium group, e.g., 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, hydroxylsultaine, or amphoacetate. [Example]

[0154]

[0165] Example

[0166] Example 1. Coated Mandarin Oranges

[0167] Coating agents A and B having the compositions shown in Table 1 were prepared.

[0155]

[0168] [Table 1]

[0156]

[0169] Mixtures 1, 2, and 3 were prepared of coating agents A and B dispersed in water at the concentrations shown in Table 2. For each of Mixtures 1, 2, and 3, groups of 120 unwaxed mandarins of the same size, quality, maturity, packing date, and orchard were coated by dipping each mandarin into a bowl of the mixture and then drying it in a rotating, moving heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated mandarins and a comparison group of uncoated mandarins was then measured. The results are shown in Table 2.

[0157]

[0170] [Table 2]

[0158]

[0171] As shown in Table 2, coatings formed from coatings containing fatty acid salts and zwitterions reduced mass loss from crops better than coatings lacking zwitterions.

[0159]

[0172] Example 2. Coated Mandarin Oranges

[0173] Coating agents C and D having the compositions shown in Table 3 were prepared.

[0160]

[0174] [Table 3]

[0161]

[0175] Mixtures 4-7 were prepared of coating agents A, C, and D dispersed in water at the concentrations shown in Table 4. For each of Mixtures 4-7, groups of 120 unwaxed mandarins of the same size, quality, maturity, packing date, and orchard were coated by dipping each mandarin into a bowl of the mixture and then drying it in a rotating, moving heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated mandarins and a comparison group of uncoated mandarins was then measured. The results are shown in Table 4.

[0162]

[0176] [Table 4]

[0163]

[0177] As shown in Table 4, coatings formed from coating agents containing fatty acid salts, zwitterions, and inorganic salts reduced mass loss from crops better than coatings lacking zwitterions and / or inorganic salts.

[0164]

[0178] Example 3. Dispersion Viscoelasticity

[0179] Coatings E and F having the compositions shown in Table 5 were prepared.

[0165]

[0180] [Table 5]

[0166]

[0181] Mixtures 8 to 10 of coating agents A, E, and F dispersed in water at the concentrations shown in Table 6 were prepared.

[0167]

[0182] [Table 6]

[0168]

[0183] The storage modulus G' and loss modulus G'' of each of Mixtures 8 to 10 were measured as a function of angular frequency (rad / s) sweeping at 0.2% oscillatory strain at 55°C along with the solution. The results are shown in Figure 1.

[0169]

[0184] Mixture 10 appeared to be a viscoelastic liquid, while Mixture 8 appeared to be a gel. This viscoelastic shift as a function of NaCl concentration can lead to improved mixing and the attainment of higher coating concentrations, as shown in Figure 1.

[0170]

[0185] Example 4. Coated Mandarin Oranges

[0186] Coating agents G to J having the compositions shown in Table 7 were prepared.

[0171]

[0187] [Table 7]

[0172]

[0188] Mixtures 11-15 were prepared of coating agents A and G-J dispersed in water at the concentrations shown in Table 8. For each of Mixtures 11-15, a group of 120 unwaxed mandarins of the same size, quality, maturity, packing date, and orchard was coated by dipping each mandarin into a bowl of the mixture and then drying it for 100 seconds at 65-70°C in a rotating, moving heat tunnel. The mass loss of the coated mandarins and a comparison group of uncoated mandarins was then measured. The results are shown in Table 8.

[0173]

[0189] [Table 8]

[0174]

[0190] As shown in Table 8, coatings formed from coatings containing fatty acid salts and zwitterions reduced mass loss from crops better than coatings lacking zwitterions.

[0175]

[0191] Example 5. Coated avocado

[0192] Coating agents K to M having the compositions shown in Table 9 were prepared.

[0176]

[0193] [Table 9]

[0177]

[0194] Mixtures 16-19 were prepared of coating agents A and K-M dispersed in water at the concentrations shown in Table 10. For each of Mixtures 16-19, a group of 120 California avocados of the same size, quality, maturity, packing date, and orchard was coated by dipping each avocado into a bowl of the mixture and then drying it for 100 seconds at 65-70°C in a rotating, moving heat tunnel. Mass loss and respiration production of the coated avocados and a comparison group of uncoated avocados were then measured. The results are shown in Table 10 and Figure 2.

[0178]

[0195] [Table 10]

[0179]

[0196] As shown in Table 10 and Figure 2, coatings formed from coatings containing increased ratios of zwitterion to fatty acid salts were better able to reduce mass loss and respiration production from the crop.

[0180]

[0197] Example 6. Coated Avocado

[0198] Mixtures 20-25 were prepared of coating agents A and J dispersed in water at the concentrations shown in Table 11. For each of Mixtures 20-25, groups of 120 California avocados of the same size, quality, maturity, packing date, and orchard were coated by spraying the solution onto each avocado on a brush bed and then drying for 100 seconds at 65-70°C in a rotating, moving heat tunnel. Mass loss and respiration production of the coated avocados and a comparison group of uncoated avocados were then measured. The results are shown in Table 11 and Figure 3.

[0181]

[0199] [Table 11]

[0182]

[0200] As shown in Table 11 and Figure 3, coatings formed from coatings containing 3 wt% lysolecithin applied at a range of coating concentrations reduced mass loss and respiration production from the crop.

[0183]

[0201] Example 7. Coated Limes

[0202] Coating agents N to R having the compositions shown in Table 12 were prepared.

[0184]

[0203] [Table 12]

[0185]

[0204] Mixtures 26-33 were prepared of coating agents A, J, and N-R dispersed in water at the concentrations shown in Table 13. For each of Mixtures 26-33, groups of 120 limes of the same size, quality, maturity, packing date, and orchard were coated by dipping each lime into a bowl of the mixture and then drying it in a rotating, moving 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.

[0186]

[0205] [Table 13]

[0187]

[0206] As shown in Table 13, coatings formed from coatings containing fatty acid salts, zwitterions, and glyceryl monolaurate were better at reducing mass loss and respiration production from crop plants.

[0188]

[0207] Example 8. Coated Tangerines

[0208] Coating agents S to U having the compositions shown in Table 14 were prepared.

[0189]

[0209] [Table 14]

[0190]

[0210] Mixtures 34-38 were prepared of coating agents A, J, and S-U dispersed in water at the concentrations shown in Table 15. For each of Mixtures 34-38, a group of 120 unwaxed tangerines of the same size, quality, maturity, packing date, and orchard were coated by dipping each tangerine into a bowl of the mixture and then drying it in a rotating, moving heat tunnel at 65-70°C for 100 seconds. The mass loss of the coated tangerines and a comparison group of uncoated tangerines was then measured. The results are shown in Table 15.

[0191]

[0211] [Table 15]

[0192]

[0212] As shown in Table 15, for a given ratio of fatty acid salt and zwitterion to monoglyceride, coatings formed from coatings containing increasing ratios of zwitterion to fatty acid salt better reduced mass loss and respiration production from the crop.

[0193]

[0213] While the present disclosure includes details of many specific embodiments, these should not be construed as limitations on the scope of the subject matter or the scope of what may be claimed, but rather as descriptions of features that may be specific to particular embodiments. Certain features described in this disclosure in the context of separate embodiments can also be implemented in combination in a single embodiment. Conversely, various features described in the context of a single embodiment can also be implemented in multiple embodiments separately or in any suitable subcombination. Furthermore, although previously described features may be described as being implemented in a particular combination, and even may be initially claimed as such, one or more features from a claimed combination can, in some cases, be deleted from the combination, and the claimed combination may be directed to subcombinations or variations of the subcombination.

[0194]

[0214] Specific embodiments of the subject matter have been described. Other embodiments, modifications, and permutations of the described embodiments, as will be apparent to those skilled in the art, are within the scope of the following claims. While operations are shown in a particular order in the drawings or claims, this should not be understood as requiring such operations to be performed in the particular order shown, or in sequential order, or that all illustrated operations be performed (although some operations may be considered optional) to achieve desirable results.

[0195]

[0215] Therefore, the exemplary embodiments set forth above do not define or constrain this disclosure. Other changes, substitutions, and alterations are also possible without departing from the spirit and scope of this disclosure.

Claims

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

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

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

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

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

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

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

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

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

10. 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 A composition comprising: a ratio of the total number of moles of said one or more monoglycerides to the total number of moles of said one or more salts and said one or more zwitterions is from about 100:1 to about 4:

1.

11. 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. 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 50:1 to about 8:

1.

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

10.

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

10.

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

16. 16. The composition of any of claims 1 to 15, comprising a lecithin or hydrolyzed lecithin comprising at least one of said zwitterions.

17. At least one of the zwitterions is positively charged groups, including quaternary ammonium or phosphonium groups; and Negatively charged groups, including phosphate, sulfonate, or carboxylate groups The composition of any one of claims 1 to 16, comprising:

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

19. At least one of the zwitterions comprises a compound of formula III-i or III-ii: 【Chemical 1】 During the ceremony: R Ｂ１ , R Ｂ２ , and R Ｂ３ But C １ ~C ２２ Alkyl and (C １ ~C ６ alkyl)-NR Ｂ４ C(O)R Ｈ are each independently selected from: R Ｂ４ Each occurrence of is independently H or C １ ~C ６ is alkyl; R Ｈ For each occurrence of, independently, C ３ ~C ２１ The composition according to any one of claims 1 to 18, wherein the compound is a side chain.

20. R Ｂ１ and R Ｂ２ However, each １ ~C ６ 20. The composition of claim 19, wherein the alkyl is alkyl.

21. R Ｂ３ But C １０ ~C ２０ 21. The composition of claim 19 or claim 20, wherein the alkyl is alkyl.

22. At least one of the zwitterions comprises a compound of Formula IIIA-i or Formula IIIA-ii: 【Chemistry 2】 During the ceremony: R Ｂ１ and R Ｂ２ But C １ ~C ６ are independently selected from alkyl; R Ｂ４ is H or C １ ~C ６ is alkyl; R Ｈ But C ３ ~C ２１ The composition according to any one of claims 1 to 21, which is a side chain.

23. R Ｂ４ The composition of claim 22, wherein is H.

24. At least one of the zwitterions comprises a compound of Formula IV: 【Chemistry 3】 During the ceremony: R Ｃ１ , R Ｃ２ , and R Ｃ３ But C １ ~C ６ are independently selected from alkyl; R Ｃ４ and R Ｃ５ is H and C(O)R Ｈ are each independently selected from: R Ｈ For each occurrence of, independently, C ３ ~C ２１ is a side chain; R Ｃ４ and R Ｃ５ The composition of any one of claims 1 to 23, wherein at least one of is not H.

25. R Ｃ４ and R Ｃ５ are each independently C(O)R Ｈ 25. The composition of claim 24, wherein:

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

27. Each of the one or more monoglycerides independently comprises a compound of Formula I-i or Formula I-ii: 【Chemistry 4】 During the ceremony: R Ａ１ and R Ａ２ However, H and C １ ~C ６ are independently selected from alkyl; R Ｈ But C ３ ~C ２７ The composition according to any one of claims 1 to 26, which is a side chain.

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

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

30. R Ｈ But C １１ ~C ２１ The composition according to any one of claims 27 to 29, which is a side chain.

31. Each of the one or more monoglycerides independently comprises a compound of formula IA-i or formula IA-ii: 【Chemistry 5】 During the ceremony: R Ａ１ and R Ａ２ However, H and C １ ~C ６ are independently selected from alkyl; R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , and R ９ But H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, and C １ ~C ６ are each independently selected from alkoxy; R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ Each time it appears, H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, and C １ ~C ６ independently selected from alkoxy; R on the adjacent carbon atom 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 these together with the carbon atoms to which they are attached form a double bond, a 3- to 6-membered heterocycloalkyl, or C ３ ~C ６ can form a cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; The composition according to any one of claims 1 to 26, wherein the sum of o and p is 0 to 17.

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

33. Each of the one or more salts independently comprises a compound of Formula II: 【Chemistry 6】 During the ceremony: R Ｈ But C ３ ~C ２７ is a side chain; X ｎ＋ The composition of any of claims 1 to 32, wherein is a cationic moiety having a formal charge n.

34. X ｎ＋ But Li ＋ , Na ＋ , K. ＋ , Cs ＋ , Ag ＋ , Ca ２＋ , Mg ２＋ , Zn ２＋ , Cu ２＋ , and (R Ｄ ) ４ N ＋ Selected from: R Ｄ appears, H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ selected from heterocycloalkyl, aryl, and heteroaryl; Each C １ ~C ６ The alkyl is C ３ ~C ６ Cycloalkyl, C ３ ~C ６ 1 to 3 R independently selected from heterocycloalkyl, aryl, and heteroaryl; Ｅ optionally substituted with; Optionally, R Ｄ together with the nitrogen atom to which they are attached form C ３ ~C ６ 34. The composition of claim 33, which forms a heterocycloalkyl.

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

36. Each of the one or more salts independently comprises a compound of formula IIA: 【Chemistry 7】 During the ceremony: R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , and R ９ But H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, and C １ ~C ６ are each independently selected from alkoxy; R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ Each time it appears, H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, and C １ ~C ６ independently selected from alkoxy; R on the adjacent carbon atom 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 these together with the carbon atoms to which they are attached form a double bond, a 3- to 6-membered heterocycloalkyl, or C ３ ~C ６ can form a cycloalkyl; o is an integer from 0 to 17; p is an integer from 0 to 17; the sum of o and p is 0 to 17; X ｎ＋ The composition of any of claims 1 to 32, wherein is a cationic moiety having a formal charge n.

37. X ｎ＋ But Li ＋ , Na ＋ , K. ＋ , Cs ＋ , Ag ＋ , Ca ２＋ , Mg ２＋ , Zn ２＋ , Cu ２＋ , and (R Ｄ ) ４ N ＋ Selected from: R Ｄ appears, H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ selected from heterocycloalkyl, aryl, and heteroaryl; Each C １ ~C ６ The alkyl is C ３ ~C ６ Cycloalkyl, C ３ ~C ６ 1 to 3 R independently selected from heterocycloalkyl, aryl, and heteroaryl; Ｅ optionally substituted with; Optionally, R Ｄ together with the nitrogen atom to which they are attached form C ３ ~C ６ 37. The composition of claim 36, which forms a heterocycloalkyl.

38. A composition according to any one of claims 1 to 37; and A mixture containing a solvent.

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

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

41. 41. The mixture of any 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. 38. A coated produce comprising an agricultural product and a layer disposed on a surface of the agricultural product, the layer comprising a composition according to any one of claims 1 to 37.

43. 43. The coated produce of claim 42, wherein the layer is disposed on a cuticular surface of the produce.

44. 44. The coated produce of claim 42 or claim 43, wherein the layer has a thickness of from about 0.1 μm to about 20 μm.

45. 44. The coated produce of claim 42 or claim 43, wherein the layer has a thickness of from about 0.1 μm to about 10 μm.

46. 1. A method for coating produce, comprising: contacting a surface of the produce with a mixture comprising a coating agent and a solvent; (The coating agent is 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 Including; the ratio of the total number of moles of said one or more monoglycerides to the total number of moles of said one or more salts and said one or more zwitterions is from about 100:1 to about 4:1; removing at least a portion of the solvent to form a coating on the surface of the produce; and A method comprising:

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

48. contacting the surfaces spraying the mixture onto the surface; or immersing said produce in said mixture.

48. The method of claim 46 or claim 47, comprising:

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

50. 50. The method of any 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, methyl tert-butyl ether.

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

52. 51. The method of any of claims 46 to 50, wherein the concentration of the coating agent in the mixture is from about 50 mg / mL to about 200 mg / mL.

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

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

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

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

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

10.

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

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

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

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

62. At least one of the zwitterions is positively charged groups, including quaternary ammonium or phosphonium groups; and Negatively charged groups, including phosphate, sulfonate, or carboxylate groups 62. The method of any one of claims 46 to 61, comprising:

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

64. 1. A method for coating produce, comprising: contacting the surface of the agricultural product with a mixture according to any one of claims 38 to 41; removing at least a portion of the solvent to form a coating on the surface of the produce; A method comprising:

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