Compounds and Formulations for Protective Coatings

Abstract

The present disclosure relates to protective coatings, for example on produce, that may include glycerophospholipid bilayer structures formed on the surface of the produce.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Patent Application No. 63 / 241,991, filed September 8, 2021, the disclosure of which is incorporated by reference in its entirety.

[0002] This invention relates to protective coatings for agricultural produce and methods of application and use thereof. [Background technology]

[0003]

[0003] Common agricultural products are susceptible to deterioration and spoilage (e.g., spoilage) when exposed to the environment. Such produce may include, for example, eggs, fruits, vegetables, crops, seeds, nuts, flowers, and / or whole plants (including their processed and semi-processed forms). Edible non-agricultural products (e.g., vitamins, candies, etc.) are also susceptible to deterioration when exposed to the ambient environment. Deterioration of agricultural products and other edible products can occur through abiotic media as a result of transpirational water loss from the exterior surface of the product to the ambient air, oxidation by oxygen diffusing into the product from the environment, mechanical damage to the surface, and / or light-induced degradation (e.g., photolysis). Biotic stressors such as bacteria, fungi, viruses, and / or pests can also infest and spoil the product.

[0004]

[0004] The cells forming the above-ground surface of most plants (such as higher plants) contain an integument or cuticle, which provides protection from water loss, oxidation, mechanical damage, photodegradation, and / or biotic stressors to varying degrees depending on the plant species and plant organ (e.g., fruit, seed, bark, flower, leaf, stem, etc.). Cutin, a biopolymer derived from cellular lipids, forms the main component of the cuticle and serves to protect the plant from environmental stressors (both abiotic and biotic stressors). The thickness, density, and composition of cutin (i.e., the different types of monomers that form cutin and their relative proportions) can vary from plant species to plant organs within the same or different plant species, and with the maturation stage of the plant. Cutin-containing parts of plants can also contain additional compounds (e.g., extracuticular waxes, phenolics, antioxidants, coloring compounds, proteins, polysaccharides, etc.). This variation in cutin composition and the thickness and density of the cutin layer between plant species, plant organs and / or between different stages of maturity of a given plant may result in different degrees of resistance between plant species or plant organs to attack by environmental stressors (i.e., water loss, oxidation, mechanical damage, and light) and / or biotic stressors (e.g., fungi, bacteria, viruses, insects, etc.).

[0005]

[0005] Conventional approaches to prevent deterioration, maintain quality, and extend the life of produce include specialized packaging and / or refrigeration. Refrigeration requires capital-intensive equipment, requires continuous energy consumption, can cause damage or loss of quality to the product if not carefully controlled, must be actively managed, and its benefits are lost when the temperature-controlled supply chain is interrupted. Produce mass loss (e.g., moisture loss) during storage increases humidity, which requires careful maintenance of relative humidity levels (e.g., with coolers) to avoid negative effects during storage (e.g., condensation, microbial growth, etc.). Furthermore, produce respiration is an exothermic process that releases heat to the surrounding air. During transportation and storage in shipping containers, heat generated by produce respiration, as well as heat generated from external environmental conditions and mechanical processes (e.g., motors), requires active cooling of the storage container to maintain the appropriate temperature for storage, which is a major cost driver for shipping companies. Slowing the rate of deterioration, reducing heat generation during storage and transportation, and extending the shelf life of produce has direct value to key investors throughout the supply chain.

[0006]

[0006] New, more cost-effective approaches are needed to prevent deterioration, reduce heat and moisture generation, maintain quality, and extend the life of produce. Such approaches may require less or no refrigeration, special packaging, etc. Summary of the Invention

[0007]

[0007] Described herein are compositions and formulations for forming protective coatings and methods of making and using the coatings. The components of the coating form a glycerophospholipid bilayer structure on the surface of the substrate (e.g., produce) on which the coating is placed, thereby forming a protective barrier. In some embodiments, the protective barrier exhibits low water and gas permeability. For example, the lattice formation adopted by the molecules of the lamellae and the intermolecular forces between the lamellae can reduce the loss of water or gas from the substrate. In some embodiments, the water and gas permeability of the coatings described herein can be altered, for example, by (1) modifying the components (e.g., coating agent) or the amount of components in the composition applied to the substrate, and (2) modifying the method used to form the coating (e.g., the temperature or rate at which the mixture containing the coating agent on the substrate is dried, and / or the concentration of the coating agent in the mixture applied to the substrate). In some embodiments, the coating agent and / or the coating formed comprises glycerophospholipid. In some embodiments, the coatings described herein are more effective barriers to water and gas than, for example, conventional wax coatings. In some such embodiments, the thickness of the coating is less than the thickness of conventional wax coatings.

[0008]

[0008] Also described herein is a method of reducing the rate of ripening of produce, the method including applying a solution comprising glycerophospholipids to a surface of the produce, and drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0009]

[0009] The disclosed concepts of the present invention include those defined in the appended claims, but it should be understood that the concepts of the present invention can also be defined according to the following embodiments.

[0010]

[0010] In addition to the embodiments in the accompanying claims and described above, the following numbered embodiments are also innovative.

[0011]

[0011] Embodiment 1 is a method for reducing the rate of ripening of produce, comprising: applying a solution comprising one or more glycerophospholipids to a surface of the produce, wherein the temperature of the solution is from about 10° C. to about 80° C.; and drying the solution on the surface of the produce under an air stream having a temperature of about 20°C to about 100°C to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0012]

[0012] Embodiment 2 is a method according to embodiment 1, wherein the one or more glycerophospholipids include one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

[0013]

[0013] Embodiment 3 is a method for preparing a glycerophospholipid comprising administering to a patient a composition comprising the steps of: [ka] comprising the formula: R 1 is -H or one of the following fragments: [ka] R 2 and R 3 each occurrence independently represents -H or Formula II: [ka] is a fragment represented by the formula: R 4 , R 5 , R 8 , R 9 , R 12 , R13 , R 14 , R 15 and R 16 Each occurrence of is independently -H, -OH, -OR 17 or C1-C6 alkyl; R 6 , R 7 , R 10 , and R 11 Each occurrence of is independently -H, -OR 17 or C1-C6 alkyl; and / or R 4 and R 5 may combine with the carbon atom to which they are attached to form C=O; and / or R 8 and R 9 may combine with the carbon atom to which they are attached to form C=O; and / or R 12 and R 13 may combine with the carbon atom to which they are attached to form C=O; R 17 is C1-C6 alkyl at each occurrence; symbol [ka] represents a single bond or a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; The method of embodiment 1 or embodiment 2, wherein r is 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0014]

[0014] Embodiment 4 is a fragment represented by formula II: [ka] [ka] [ka] [ka] [ka] 4. The method according to embodiment 3, which is one of the methods described above.

[0015]

[0015] Embodiment 5 is a method according to any one of embodiments 1 to 4, wherein the one or more glycerophospholipids include phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.

[0016]

[0016] Embodiment 6 is a method described in embodiment 5, wherein the one or more glycerophospholipids comprise about 20% to about 40% by weight phosphatidylcholine, about 20% to about 40% by weight phosphatidylethanolamine, and about 20% to about 40% by weight phosphatidylinositol.

[0017]

[0017] Embodiment 7 is a method according to embodiment 5 or embodiment 6, wherein the one or more glycerophospholipids further comprise phosphatidylserine.

[0018]

[0018] Embodiment 8 is a method according to embodiment 7, wherein the one or more glycerophospholipids contain less than about 5% by weight phosphatidylserine.

[0019]

[0019] Embodiment 9 is a method according to any one of embodiments 1 to 8, wherein the solution further comprises a plant sterol.

[0020]

[0020] Embodiment 10 is a method according to embodiment 9, wherein the weight ratio of plant sterol to the total amount of glycerophospholipid is less than about 0.05.

[0021]

[0021] Embodiment 11 is a method according to any one of embodiments 1 to 10, wherein the total concentration of one or more glycerophospholipids in the solution is from about 10 g / L to about 200 g / L.

[0022]

[0022] Embodiment 12 is a method according to any one of embodiments 1 to 11, wherein the total concentration of one or more glycerophospholipids in the solution is from about 50 g / L to about 150 g / L.

[0023]

[0023] Embodiment 13 is a method according to any one of embodiments 1 to 10, wherein the total concentration of one or more glycerophospholipids in the solution is from about 80 g / L to about 120 g / L.

[0024]

[0024] Embodiment 14 is a method according to any one of embodiments 1 to 10, wherein the total concentration of one or more glycerophospholipids in the solution is from about 90 g / L to about 110 g / L.

[0025]

[0025] Embodiment 15 is the method of any one of embodiments 1 to 14, wherein the solution is an aqueous solution.

[0026]

[0026] Embodiment 16 is the method of any one of embodiments 1 to 15, wherein the solution does not contain an added surfactant.

[0027]

[0027] Embodiment 17 is the method of any one of embodiments 1 to 16, wherein the temperature of the air is about 50°C to about 100°C.

[0028]

[0028] Embodiment 18 is a method according to any one of embodiments 1 to 17, wherein the glycerophospholipid layer comprises one or more open bilayers.

[0029]

[0029] Embodiment 19 is the method of embodiment 18, wherein one or more of the open bilayers is lamellar.

[0030]

[0030] Embodiment 20 is a method according to any one of embodiments 1 to 17, wherein the glycerophospholipid layer comprises one or more closed bilayers.

[0031]

[0031] Embodiment 21 is the method of embodiment 20, wherein one or more of the closed bilayers is cylindrical.

[0032]

[0032] Embodiment 22 is the method of embodiment 20, wherein one or more of the closed bilayers is spherical.

[0033]

[0033] Embodiment 23 is the method of any one of embodiments 1 to 22, wherein the layer thickness is less than about 2 microns.

[0034]

[0034] Embodiment 24 is the method of any one of embodiments 1-22, wherein the layer thickness is less than about 1 micron.

[0035]

[0035] Embodiment 25 is a method for reducing the respiration rate of agricultural produce, comprising: applying a solution comprising one or more glycerophospholipids to a surface of the produce, wherein the temperature of the solution is from about 10° C. to about 80° C.; and drying the solution on the surface of the produce under an air stream having a temperature of about 20°C to about 100°C to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0036]

[0036] Embodiment 26 is a method for reducing mass loss rate of produce, comprising: applying a solution comprising one or more glycerophospholipids to a surface of the produce, wherein the temperature of the solution is from about 10° C. to about 80° C.; and drying the solution on the surface of the produce under an air stream having a temperature of about 20°C to about 100°C to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0037]

[0037] Embodiment 27 is a method of preparing a produce having a coating disposed thereon, comprising: applying a solution comprising one or more glycerophospholipids to a surface of the produce, wherein the temperature of the solution is from about 10° C. to about 80° C.; and drying the solution on the surface of the produce under an air stream having a temperature of about 20°C to about 100°C to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0038]

[0038] Embodiment 28 is Agricultural products; and Coating on the surface of agricultural products 1. A coated agricultural product comprising: One or more glycerophospholipids, and The coated produce comprises a plurality of glycerophospholipid bilayers on a surface of the produce.

[0039]

[0039] Embodiment 29 is a coated produce described in embodiment 28, wherein the one or more glycerophospholipids include one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

[0040]

[0040] Embodiment 30 is a method for preparing a glycerophospholipid comprising administering to a patient a composition comprising one or more glycerophospholipids selected from the group consisting of one or more compounds of formula I: [ka] comprising the formula: R 1 is -H or one of the following fragments: [ka] R 2 and R 3 each occurrence independently represents -H or Formula II: [ka] is a fragment represented by the formula: R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 and R 16 Each occurrence of is independently -H, -OH, -OR 17 or C1-C6 alkyl; R 6 , R 7 , R 10 , and R 11 Each occurrence of is independently -H, -OR 17 or C1-C6 alkyl; and / or R 4 and R 5 may combine with the carbon atom to which they are attached to form C=O; and / or R 8 and R 9 may combine with the carbon atom to which they are attached to form C=O; and / or R 12 and R 13 may combine with the carbon atom to which they are attached to form C=O; R 17 is C1-C6 alkyl at each occurrence; symbol [ka] represents a single bond or a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; The coated produce of embodiment 28 or embodiment 29, wherein r is 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0041]

[0041] Embodiment 31 is an embodiment in which the fragment represented by formula II is [ka] [ka] [ka] [ka] The coated produce of embodiment 30, wherein the coated produce is one of

[0042]

[0042] Embodiment 32 is a coated produce described in any one of embodiments 28 to 31, wherein the one or more glycerophospholipids include phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.

[0043]

[0043] Embodiment 33 is a coated agricultural product described in embodiment 32, wherein the one or more glycerophospholipids comprise 20% to 40% by weight of phosphatidylcholine, 20% to 40% by weight of phosphatidylethanolamine, and 20% to 40% by weight of phosphatidylinositol.

[0044]

[0044] Embodiment 34 is a coated agricultural product described in embodiment 32 or embodiment 33, wherein the one or more glycerophospholipids further comprise phosphatidylserine.

[0045]

[0045] Embodiment 35 is a coated produce described in embodiment 34, wherein the one or more glycerophospholipids contain less than 5% by weight of phosphatidylserine.

[0046]

[0046] Embodiment 36 is a coated produce described in any one of embodiments 28 to 35, wherein the plurality of glycerophospholipid bilayers comprises one or more open bilayers.

[0047]

[0047] Embodiment 37 is a coated produce described in embodiment 36, wherein one or more of the open bilayers is layered.

[0048]

[0048] Embodiment 38 is a coated produce described in any one of embodiments 28 to 35, wherein the plurality of glycerophospholipid bilayers comprises one or more closed bilayers.

[0049]

[0049] Embodiment 39 is a coated produce described in embodiment 38, wherein one or more of the closing bilayers is cylindrical.

[0050]

[0050] Embodiment 40 is a coated produce described in embodiment 38, wherein one or more of the closing bilayers is spherical.

[0051]

[0051] Embodiment 41 is the coated produce of any one of embodiments 28-40, wherein the coating thickness is less than 2 microns.

[0052]

[0052] Embodiment 42 is the coated produce of any one of embodiments 28-40, wherein the coating has a thickness of less than 1 micron.

[0053]

[0053] The details of one or more embodiments of the presently disclosed subject matter are set forth in the accompanying drawings and the specification. Other features, aspects, and advantages of the subject matter will become apparent from the specification, drawings, and claims. [Brief description of the drawings]

[0054] [Figure 1]

[0054] Plots of mass loss factor (MLF) for untreated produce, produce coated with a coating comprising one or more monoglycerides, and produce coated with a coating comprising one or more glycerophospholipids are shown. [Diagram 2]

[0055] 1 shows plots of respiration rates for untreated produce, produce coated with a coating comprising one or more monoglycerides, and produce coated with a coating comprising one or more glycerophospholipids. [Diagram 3]

[0056] 1 shows a plot of intensity versus q (Å −1 ) from an X-ray scattering image of a coating on a polystyrene substrate. [Figure 4]

[0057] 1 shows a plot of mass loss coefficient for produce treated with various coatings. [Diagram 5]

[0058] 1 shows plots of respiration rates for produce treated with various coatings. [Figure 6]

[0059] 1 shows plots of intensity versus q (Å −1 ) from X-ray scattering images of coatings applied at various concentrations onto a polystyrene substrate. [Figure 7]

[0060] 1 shows plots of intensity versus q (Å −1 ) from X-ray scattering images of coatings applied at various concentrations onto a polystyrene substrate. [Figure 8]

[0061] 1 shows plots of intensity versus q (Å −1 ) from out-of-plane (⊥) and in-plane (||) X-ray scattering images of a coating applied on a polystyrene substrate. [Figure 9]

[0062] 1 shows a plot of mass loss coefficient for produce treated with various coatings. [Figure 10]

[0063] 1 shows a plot of intensity versus q (Å −1 ) from X-ray scattering images of non-hydrogenated phosphatidylcholine (PC) and hydrogenated phosphatidylcholine coatings applied onto a polystyrene substrate. [Figure 11]

[0064] 1 shows a plot of intensity versus q (Å −1 ) from an X-ray scattering image of a hydrogenated phosphatidylcholine coating applied onto a polystyrene substrate. [Figure 12]

[0065] 1 shows a plot of intensity versus q (Å −1 ) from an X-ray scattering image of a non-hydrogenated phosphatidylcholine coating applied onto a polystyrene substrate. [Figure 13]

[0066] 1 shows a plot of intensity versus q (Å −1 ) from an X-ray scattering image of a coating applied onto a polystyrene substrate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0055] definition

[0067] As used herein, the term "plant material" refers to any part of a plant, including, for example, fruits (botanically, including fruit skins and juice sacs), vegetables, leaves, stems, bark, seeds, flowers, peels, or roots. Plant material includes pre-harvested plants or parts thereof as well as post-harvested plants or parts thereof (including, for example, harvested fruits and vegetables, harvested roots and berries, and picked flowers).

[0056]

[0068] As used herein, "coating agent" refers to a composition that includes a compound or group of compounds that can form a protective coating.

[0057]

[0069] As used herein, "mass loss rate" refers to the rate at which a product loses mass (e.g., by releasing water and other volatile compounds). Mass loss rate is typically expressed as a percentage of the original mass per unit time (e.g., percent per day).

[0058]

[0070] As used herein, the term "mass loss coefficient" is defined as the ratio of the average mass loss rate of an uncovered crop (measured for a control group) to the average mass loss rate of a corresponding test crop (e.g., a covered crop) over a given time period. Thus, a larger mass loss coefficient for a covered crop corresponds to a larger reduction in the average mass loss rate for the covered crop.

[0059]

[0071] As used herein, the term "respiration rate" refers to the rate at which a product releases a gas, such as CO2. This rate may be determined from the volume of gas (e.g., CO2) released per unit time per unit mass of product (at standard temperature and pressure). Respiration rate may be expressed as ml gas / kg·h. The respiration rate of a product may be measured by placing the product in a sealed container of known volume equipped with a sensor, such as a CO2 sensor, that records the gas concentration in the container as a function of time, and then calculating the rate of gas release required to obtain a measured concentration value.

[0060]

[0072] As used herein, the term "respiration coefficient" is defined as the ratio of the average gas diffusion (e.g., CO2 emission) of an uncovered crop (measured for a control group) to the average gas diffusion of a corresponding test crop (e.g., a covered crop) over a given time period. Thus, a larger respiration coefficient for a covered crop corresponds to a larger reduction in gas diffusion / respiration for the covered crop.

[0061]

[0073] As used herein, the term "contact angle" of a liquid on a solid surface refers to the angle of the exterior surface of a droplet of the liquid measured when the gas-liquid interface meets the liquid-solid interface. The contact angle quantifies the wettability of a solid surface by a liquid.

[0062]

[0074] As used herein, the terms "wetting agent" and "surfactant" refer to a compound that, when added to a solvent, suspension, colloid, or solution, respectively, reduces the difference in surface energy between the solvent / suspension / colloid / solution and the solid surface on which the solvent / suspension / colloid / solution is placed.

[0063]

[0075] As used herein, "lipid bilayer" or "bilayer structure" refers to a structure that includes two consecutive sublayers, each of which includes molecules of glycerophospholipids aligned adjacent to each other in the longitudinal direction, with the hydrophilic ends forming a hydrophilic surface and the hydrophobic ends forming a hydrophobic surface; the molecular arrangement defines a repeating lattice structure. The hydrophobic surfaces of each sublayer in the lipid bilayer face each other, and the hydrophilic surfaces of each layer face away from each other. A lipid bilayer can be an "open bilayer" in which each sublayer is arranged in parallel sheets. For example, an open bilayer can have a layered structure. A lipid bilayer can also be a "closed bilayer" in which each sublayer is arranged in a ring structure. For example, a closed bilayer can have a spherical or cylindrical structure.

[0064]

[0076] As used herein, a "lamellar structure" refers to a structure that includes lamellae that are stacked vertically adjacent to each other and held together by intermolecular forces. As used herein, a "lamella" refers to one lamella or two or more lamellae, i.e., one or more individual layers of molecules each. In some embodiments, the molecules present in a lamella are ordered (e.g., aligned as in an open bilayer). The distance between the surface of a lamella and the surface of an adjacent lamella that faces in the same direction is referred to herein as the "interlayer spacing" or "periodic spacing". The interlayer spacing between two lamellae is determined by (1) acquiring an out-of-plane X-ray scattering image of the coating, (2) determining the scattering vector (q) of the peak corresponding to the lamellar structure, and (3) determining the interlayer spacing (d) using the following Bragg equation: d=2π / q peak (1)

[0065]

[0077] As used herein, "grain" refers to a region in a polycrystalline structure where the lattice formation is continuous and has one orientation. The boundaries between grains in a polycrystalline structure are lattice formation defects where the continuity of the lattice formation and / or the orientation of the molecules forming the lattice formation are interrupted. The "grain size" of the grains forming a coating is determined by (1) obtaining an in-plane X-ray scattering image of the coating; (2) determining the full width at half maximum (FWHM) of the peaks corresponding to the molecules in the coating; and (3) calculating the grain size (D) using the following Scherrer equation: D=2πb / FWHM (2) where b=about 0.95 for a two-dimensional crystal.

[0066]

[0078] Without being bound by theory, grain size is inversely correlated with grain boundaries. Thus, the larger the grain size, the fewer grain boundaries; and the smaller the grain size, the more grain boundaries there are. It is further understood that the fewer grain boundaries in a coating, the lower the mass loss rate and / or respiration rate of the coated produce, since there are fewer paths for water and / or gases to pass through the coating.

[0067]

[0079] As used herein, "mosaicity" refers to the probability that the orientation of crystal planes in a polycrystalline structure (e.g., a coating) deviates from a plane substantially parallel to the plane of the substrate (e.g., produce) surface. Deviations of crystal planes from a plane substantially parallel to the plane of the substrate surface are understood to be a type of crystal defect that increases the permeability of the coating to air and water, thereby increasing the rate of mass loss and respiration when the coating is placed on produce.

[0068]

[0080] As used herein, "substrate" refers to the article to which the coating is applied. In some embodiments, the substrate is an agricultural product (e.g., a crop), a silicon substrate, a polystyrene substrate, or a substrate comprising a polysaccharide (e.g., cellulose).

[0069] Protective Coating

[0081] Described herein are solutions, suspensions, or colloids containing compositions (e.g., coating agents) in a solvent that can be used to form protective coatings on substrates such as plant material, produce, or food. The protective coatings can, for example, prevent or reduce moisture loss and gas diffusion from the substrate, oxidation of the substrate, and / or protect the substrate from threats such as bacteria, fungi, viruses, and the like. The coatings can also protect the substrate from physical damage (e.g., bruising) and light damage. Thus, the coating agents, solutions / suspensions / colloids, and coatings formed can be used to help store produce or other food products for extended periods of time without damage. In some cases, the coatings and coating agents formed therein can allow food to remain fresh in the absence of refrigeration. The coating agents and coatings described herein can also be edible (i.e., the coating agents and coatings can be non-toxic for human consumption). In some particular implementations, the solutions / suspensions / colloids include wetting agents or surfactants that allow the solution / suspensions / colloids to better spread across the surface of the substrate during application, thereby improving the surface coverage and overall performance of the resulting coating. In some particular implementations, the solution / suspension / colloid includes an emulsifier that improves the solubility of the coating agent in the solvent and / or suspends or disperses the coating agent in the solvent. The wetting agent and / or the emulsifier may each be a component of the coating agent or may be added separately to the solution / suspension / colloid. In some embodiments, the coating includes a layered structure formed on the surface of the substrate (e.g., produce) on which the coating is disposed. In some embodiments, the coating includes a cylindrical structure formed on the surface of the substrate (e.g., produce) on which the coating is disposed.

[0070]

[0082] Plant material (e.g., produce) and other degradable articles can be protected from deterioration due to biotic or abiotic stressors by forming a protective coating on the exterior surface of the product. The coating can be formed by adding the components of the coating (collectively herein "coating agent") to a solvent (e.g., water and / or ethanol) to form a mixture (e.g., a solution, suspension, or colloid), applying the mixture to the exterior surface of the product to be coated, e.g., by immersing the product in the mixture or by brushing or spraying the mixture on the surface of the product, and then removing the solvent from the surface of the product, e.g., by evaporating the solvent, thereby forming a coating from the coating agent on the surface of the product. The coating agent can be formulated such that the resulting coating provides a barrier to water and / or oxygen migration, thereby preventing moisture loss from the coated product and / or oxidation of the coated product. The coating agent can additionally or alternatively be formulated such that the resulting coating provides a barrier to CO2, ethylene, and / or other gas migration.

[0071]

[0083] Coating agents containing glycerophospholipids can be used as coating agents to form coatings that can be safe for human consumption and are effective in slowing the rate of ripening and reducing mass loss and oxidation in a variety of agricultural produce.

[0072] Coatings and coating compositions

[0084] In some embodiments, the composition (e.g., coating agent or coating) comprises one or more glycerophospholipids. Exemplary types of glycerophospholipids include phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid. In some embodiments, the one or more glycerophospholipids comprise one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

[0073]

[0085] In certain embodiments, the one or more glycerophospholipids comprise one or more compounds of formula I, wherein formula I is: [ka] wherein: R 1 is -H or one of the following fragments: [ka] R 2 and R 3 is each independently at each occurrence -H or a fragment represented by formula II, where formula II is: [ka] wherein: R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 and R 16 Each occurrence of is independently -H, -OH, -OR 17 or C1-C6 alkyl; R 6 , R 7 , R 10 , and R 11 Each occurrence of is independently -H, -OR 17 or C1-C6 alkyl; and / or R 4 and R 5 may combine with the carbon atom to which they are attached to form C=O; and / or R 8 and R 9 may combine with the carbon atom to which they are attached to form C=O; and / or R 12 and R 13 may combine with the carbon atom to which they are attached to form C=O; R 17 is C1-C6 alkyl at each occurrence; symbol [ka] represents a single bond or a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0074]

[0086] In some embodiments, the composition (e.g., coating agent or coating) comprises the following fragment of formula II: [ka] [ka] [ka] [ka] The lipid composition comprises one or more glycerophospholipids, including one or more of the following:

[0075]

[0087] In one embodiment, the compound of formula I is a compound of formula Ia: [ka] It is.

[0076]

[0088] In one embodiment, the compound of formula I is a compound of formula Ib: [ka] It is.

[0077]

[0089] In certain embodiments, the one or more glycerophospholipids comprise a racemic mixture of compounds of Formula Ia and Formula Ib.

[0078]

[0090] In some embodiments, the one or more glycerophospholipids comprise a phosphatidylcholine. In some embodiments, the phosphatidylcholine is a compound of formula I, where R 1 but, [ka] In certain embodiments, the one or more glycerophospholipids comprise from about 1% to about 99% by weight of phosphatidylcholine, for example, from about 5% to about 75%, from about 10% to about 65%, from about 15% to about 50%, or from about 20% to about 40% by weight of phosphatidylcholine.

[0079]

[0091] In some embodiments, the one or more glycerophospholipids comprise a phosphatidylethanolamine. In some embodiments, the phosphatidylethanolamine is a compound of formula I, where R 1 but, [ka] In certain embodiments, the one or more glycerophospholipids contain about 1% to about 50% by weight of phosphatidylethanolamine, for example, about 5% to about 50%, about 10% to about 45%, about 15% to about 40%, or about 20% to about 40% by weight of phosphatidylethanolamine.

[0080]

[0092] In some embodiments, the one or more glycerophospholipids comprise a phosphatidylinositol. In some embodiments, the phosphatidylinositol is a compound of formula 1, where R 1 but, [ka] In certain embodiments, the one or more glycerophospholipids contain about 1% to about 50% by weight of phosphatidylinositol, for example, about 5% to about 50%, about 10% to about 45%, about 15% to about 40%, or about 20% to about 40% by weight of phosphatidylinositol.

[0081]

[0093] In some embodiments, the one or more glycerophospholipids include phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol. In some embodiments, the one or more glycerophospholipids include about 20% to about 40% by weight of phosphatidylcholine, about 20% to about 40% by weight of phosphatidylethanolamine, and about 20% to about 40% by weight of phosphatidylinositol.

[0082]

[0094] In some embodiments, the one or more glycerophospholipids comprise a phosphatidylserine. In some embodiments, the phosphatidylserine is a compound of formula I, where R 1 but, [ka] In certain embodiments, the one or more glycerophospholipids contain less than about 25% by weight phosphatidylserine, e.g., less than about 15%, less than about 10%, or less than about 5% phosphatidylserine by weight.

[0083]

[0095] In some embodiments, the one or more glycerophospholipids comprise a phosphatidylglycerol. In some embodiments, the phosphatidylglycerol is a compound of formula I, where R 1 but, [ka] In certain embodiments, the one or more glycerophospholipids contain less than about 25% phosphatidylglycerol by weight, e.g., less than about 15%, less than about 10%, or less than about 5% phosphatidylglycerol by weight.

[0084]

[0096] In some embodiments, the one or more glycerophospholipids include phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylglycerol, and phosphatidylserine. In some embodiments, the one or more glycerophospholipids include about 20% to about 40% by weight of phosphatidylcholine, about 20% to about 40% by weight of phosphatidylethanolamine, about 20% to about 40% by weight of phosphatidylinositol, and less than about 5% by weight of phosphatidylserine.

[0085]

[0097] In some embodiments, the coating agent further comprises a plant sterol, hi some embodiments, the weight ratio of the plant sterol to the total amount of the one or more glycerophospholipids is less than about 0.2, e.g., less than about 0.15, 0.1, or 0.05.

[0086] Coating mixture

[0098] In some embodiments, the composition (e.g., coating agent) may be dissolved, mixed, dispersed, or suspended in a solvent to form a mixture (e.g., a solution, a suspension, or a colloid). Examples of solvents that may be used include water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, and combinations thereof. In one example, the solvent is water. In one example, the solvent is ethanol. In some embodiments, the composition is dissolved or suspended in water to form an aqueous solution.

[0087]

[0099] In one embodiment, the concentration of the composition (e.g., coating agent) in the solution or mixture (e.g., solution, suspension, or colloid) is about 10 mg / mL to about 200 mg / mL, for example, about 10 to about 150 mg / mL, about 10 to about 120 mg / mL, about 10 to about 100 mg / mL, about 20 to about 200 mg / mL, about 20 to about 175 mg / mL, about 20 to about 150 mg / mL, about 20 about 100 mg / mL, about 30 to about 175 mg / mL, about 30 to about 200 mg / mL, about 30 to about 175 mg / mL, about 30 to about 150 mg / mL, about 30 to about 120 mg / mL, about 30 to about 100 mg / mL, about 40 to about 175 mg / mL, about 50 mg / mL to about 150 mg / mL, about 80 mg / mL to about 120 mg / mL, or about 90 mg / mL to about 110 mg / mL. In one example, the concentration of the composition (e.g., coating agent) in the mixture (e.g., solution, suspension, or colloid) is about 100 mg / mL.

[0088]

[0100] In certain embodiments, the concentration of the composition is less than 200 mg / mL, or less than 175 mg / mL. In some instances, phase separation and / or precipitation can occur at concentrations greater than 200 mg / mL, which can affect the appearance and applicability of the coating.

[0089]

[0101] As described above, the coating agent may be formed primarily from various combinations of glycerophospholipids. Also, as described above, the coating agent may be formed primarily from various combinations of fatty acid derivatives. Also, as described above, the coating may be formed on the exterior surface of the produce by dissolving, suspending, or dispersing the coating agent in a solvent to form a mixture, applying the mixture to the surface of the produce (e.g., by spray coating the product, by dipping the product in the mixture, or by brushing the mixture onto the surface of the produce), and then removing the solvent (e.g., by evaporating the solvent). The solvent may include any polar, non-polar, protic, or aprotic solvent (including any combination thereof). Examples of solvents that may be used include water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, any other suitable solvent, and combinations thereof. If the coating is to be applied to a plant or other edible product, it may be preferable to use a solvent that is safe for consumption, such as water, ethanol, or combinations thereof. Depending on the solvent used, the solubility limit of the coating agent in the solvent may be less than necessary for a particular application.

[0090]

[0102] The coating agent may further include an emulsifier to improve the solubility of the coating agent in the solvent or to allow the coating agent to be suspended or dispersed in the solvent. If the coating is to be formed on a plant or other edible product, it may be preferable that the emulsifier is safe for consumption. Furthermore, it is also preferable that the emulsifier is not incorporated into the coating, or if the emulsifier is incorporated into the coating, it does not impair the performance of the coating.

[0091]

[0103] As described above, the coating agent may be added to a solvent or dissolved, suspended, or dispersed in the solvent to form a colloid, suspension, or solution. The various components of the coating agent (e.g., one or more glycerophospholipids) may be combined before being added to the solvent and then added to the solvent together. Alternatively, the components of the coating agent may be kept separate from each other and then added to the solvent sequentially (or at different times).

[0092]

[0104] In some embodiments, the coating solution / suspension / colloid may further include a wetting agent that serves to reduce the contact angle between the solution / suspension / colloid and the surface of the substrate to be coated. The wetting agent may be included as a component of the coating agent and thus may be added to the solvent at the same time as the other components of the coating agent. Alternatively, the wetting agent may be separate from the coating agent and may be added to the solvent before, after, or at the same time as the coating agent. Alternatively, the wetting agent may be separate from the coating agent and may be applied to the surface before the coating agent to prime the surface.

[0093]

[0105] In some embodiments, the coating (solution / suspension / colloid) does not contain added wetting agents or surfactants.

[0094]

[0106] In some embodiments, the mixture or composition (e.g., coating or coating agent) includes one or more (e.g., 1, 2, or 3) preservatives. In some embodiments, the one or more preservatives include one or more antioxidants, one or more antimicrobial agents, one or more chelating agents, or any combination thereof. Exemplary preservatives include, but are not limited to, vitamin E, vitamin C, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), sodium benzoate, disodium ethylenediaminetetraacetate (EDTA), citric acid, benzyl alcohol, benzalkonium chloride, butylparaben, chlorobutanol, metacresol, chlorocresol, methylparaben, phenylethyl alcohol, propylparaben, phenol, benzonic acid, sorbic acid, methylparaben, propylparaben, bronidol, and propylene glycol.

[0095]

[0107] Any of the coating solutions / suspensions / colloids described herein may further include an antimicrobial agent, such as ethanol or citric acid. In some embodiments, the antimicrobial agent is part of the solvent or is a component of the solvent. Any of the coating solutions described herein may further include other components or additives, such as sodium bicarbonate.

[0096]

[0108] Any of the coatings described herein may further include additional materials, which may also be transported to the surface with the coating or deposited separately and then encapsulated by the coating (e.g., the coating is formed at least partially around the additional material), or deposited separately and then supported by the coating (e.g., the additional material is affixed to the outer surface of the coating). Examples of such additional materials may include cells, biosignaling molecules, vitamins, minerals, pigments, fragrances, enzymes, catalysts, antifungal agents, antibacterial agents, and / or sustained release drugs. The additional materials may be non-reactive with the surface and / or coating of the coated product, or alternatively, may be reactive with the surface and / or coating.

[0097]

[0109] In some embodiments, the coating may include additives configured to, for example, modify the viscosity, vapor pressure, surface tension, or solubility of the coating. The additives may be configured, for example, to increase the chemical stability of the coating. For example, the additives may be antioxidants configured to inhibit oxidation of the coating. In some embodiments, the additives may reduce or increase the melting temperature or glass transition temperature of the coating. In some embodiments, the additives may be configured to reduce the diffusivity of water vapor, oxygen, CO2, or ethylene through the coating, or to allow the coating to absorb more ultraviolet (UV) light, for example, to protect produce (or any of the other products described herein). In some embodiments, the additives may be configured to impart an intended scent, for example, a flavor (e.g., floral, fruity, botanical scent, freshness, fragrance, etc.). In some embodiments, the additives may be configured to impart color, for example, a dye or a color additive approved by the US Food and Drug Administration (FDA).

[0098]

[0110] Any of the coating agents described herein or the coatings formed therefrom may have no flavor or a high flavor threshold, for example, greater than 500 ppm, and may have no flavor or a high odor threshold. In some embodiments, the materials included in any of the coatings described herein may be substantially transparent. For example, the coating agents, solvents, and / or any other additives included in the coating may be selected so that they have substantially the same or similar refractive index. By matching their refractive indexes, they may optionally be adapted to reduce light scattering and improve light transmission. For example, a coating with substantially transparent properties may be formed by using materials with similar refractive indexes and clear, transparent properties.

[0099]

[0111] Any of the coatings described herein may be disposed on the exterior surface of produce or other substrates using any suitable means. For example, the substrate may be dip coated in a bath of the coating formulation (e.g., aqueous or mixed aqueous-organic or organic solution). The deposited coating may form a thin layer on the surface of the produce, which may protect the produce from biotic stressors, water loss, respiration, and / or oxidation. In some embodiments, the deposited coating may have a thickness of less than about 20 microns, 10 microns, 9 microns, 8 microns, 7 microns, 6 microns, 5 microns, 4 microns, 3 microns, 2 microns, or 1.5 microns. In some embodiments, the deposited coating may have a thickness of about 100 nm to about 20 microns, about 100 nm to about 2 microns, about 700 nm to about 1.5 microns, about 700 nm to about 1 micron, about 1 micron to about 1.6 microns, about 1.2 microns to about 1.5 microns. In some embodiments, the coating is transparent to the naked eye.

[0100]

[0112] In some embodiments, the deposited coating may be substantially uniformly deposited on the substrate and may be free of defects and / or pinholes. In some embodiments, the dip coating process may include continuous coating of the produce in a bath of coating precursors that may self-assemble or covalently bond on the produce to form the coating. In some embodiments, the coating may be deposited on the produce by passing the produce under a stream of coating solution / suspension / colloid (e.g., a waterfall of coating solution / suspension / colloid). For example, the produce may be placed on a conveyor that passes through a stream of coating solution / suspension / colloid. In some embodiments, the coating may be sprayed, evaporated or dry evaporated onto the surface of the produce. In some embodiments, the coating solution / suspension / colloid may be mechanically applied to the surface of the produce to be coated, for example, by brushing it onto the surface. In some embodiments, the coating may be configured to be fixed to the surface of the produce by UV crosslinking or by exposure to a reactive gas, such as oxygen.

[0101]

[0113] In some embodiments, the coating solution / suspension / colloid can be spray coated onto the produce. Commercially available sprayers can be used to spray the coating solution / suspension / colloid onto the produce. In some embodiments, the coating formulation can be charged in the sprayer prior to spray coating onto the produce, such that the deposited coating electrostatically and / or covalently bonds to the exterior surface of the produce.

[0102]

[0114] In some embodiments, the coating formed from the coating agent described herein on the produce can be configured to change the surface energy of the produce. Various properties of the coating described herein can be adjusted by adjusting the crosslink density of the coating, its thickness, or its chemical composition. This can be used, for example, to control the ripening of fruits or produce after harvest. For example, a coating formed from a coating agent that mainly contains difunctional or polyfunctional monomer units can have a higher crosslink density than, for example, one that contains monofunctional monomer units. Thus, a coating formed from difunctional or polyfunctional monomer units can, in some cases, result in a slower ripening rate compared to a coating formed from monofunctional monomer units.

[0103]

[0115] As mentioned above, coatings formed from the coating agents described herein can be configured to prevent water loss or other moisture loss from the covered part of the plant, retard ripening, and / or prevent oxygen diffusion into the covered part of the plant, for example, to reduce oxidation of the covered part of the plant. The coating can also act as a barrier against the diffusion of carbon dioxide and / or ethylene to or from the plant or produce. The coating can also protect the covered part of the plant from biotic stressors, such as bacteria, fungi, viruses, and / or pests, which may invade and spoil the covered part of the plant, for example. Because bacteria, fungi, and pests all identify food sources by recognizing certain molecules on the surface of the produce, coating the produce with a coating agent can deposit molecularly contrasting molecules on the surface of the plant part, thereby making the produce unrecognizable. Additionally, the coating can also change the physical and / or chemical environment of the surface of the produce, making it unfavorable for bacteria, fungi, or pests to grow on. Coatings may also be formulated to protect the surface of the plant part from abrasion, bruising, or other mechanical damage and / or to protect the plant part from photodegradation. Plant parts may include, for example, leaves, stems, shoots, flowers, fruits, roots, etc.

[0104]

[0116] Any of the coatings described herein may be used to reduce moisture generated by produce (e.g., fresh produce) due to mass loss (e.g., moisture loss) during transportation and storage by reducing the rate of mass loss of the produce (e.g., fresh produce).

[0105]

[0117] In some embodiments, the produce is coated with a composition that reduces the rate of mass loss by at least about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to measurements of the untreated product. In some embodiments, treating the produce with any of the coatings described herein results in a mass loss factor of at least about 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.2, 2.4, 2.6, 2.8, or 3.0. In some embodiments, treating produce with any of the coatings described herein may reduce humidity generated during storage by at least about 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to untreated products. In some embodiments, a reduction in the rate of mass loss of the produce may reduce the energy required to maintain the relative humidity at a given level (e.g., below about 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, or 45% relative humidity) during storage or transport. In certain embodiments, the energy required to maintain relative humidity at a predetermined level (e.g., any of the predetermined levels listed above) during storage or transportation can be reduced by at least about 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to an untreated product.

[0106]

[0118] Any of the coatings described herein can be used to reduce the heat generated by produce (e.g., fresh produce) through respiration during transport and storage by slowing the respiration rate of the produce (e.g., fresh produce). In some embodiments, the product is coated with a composition that reduces the respiration rate by at least about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to an untreated product (measured as described above). In some embodiments, the reduction in heat generated by the produce can reduce the energy required to maintain a temperature (e.g., a given temperature) during storage or transport. In certain embodiments, the heat generated may be reduced by at least about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more for a coated product compared to an untreated product. In certain embodiments, the energy required to maintain a coated product at a predetermined temperature (e.g., at or below about 25°C, 23°C, 20°C, 18°C, 15°C, 13°C, 10°C, 8°C, 5°C, or 3°C) may be reduced by at least about 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or more compared to an untreated product.

[0107]

[0119] Estimates of respiration rates for various types of produce (eg, fresh produce) are shown in Table 1.

[0108] [Table 1]

[0109]

[0120] In some embodiments, the methods and compositions described herein are used to treat produce (e.g., fresh produce) stored and / or transported in a refrigerated container or "refrigerator". Heat from the respiration of the produce contributes to the overall heat within the refrigerated container. In some embodiments, the methods and compositions described herein may reduce the respiration rate of the treated produce (e.g., fresh produce) to reduce the heat generated by the respiration of the produce (e.g., fresh produce) in the refrigerated container or "refrigerator". In some embodiments, the methods and compositions described herein may reduce the mass loss rate of the treated produce (e.g., fresh produce) to reduce the moisture generated by mass loss (e.g., moisture loss) of the produce (e.g., fresh produce) in the refrigerated container or "refrigerator".

[0110]

[0121] The methods and compositions described herein can also be used to minimize or reduce temperature or humidity gradients resulting from assembling produce (e.g., fresh produce) on stacks or pallets to prevent uneven ripening. Processed produce (e.g., fresh produce) can be stacked linearly during storage or stacked in other formats (e.g., cross-stacked) to increase circulation around the produce (e.g., fresh produce). Within the produce supply chain, boxes of produce can be rearranged from linear stacks, which may be preferred during transportation, to cross-stacks, which may be used during storage to increase air circulation and prevent uneven ripening.

[0111]

[0122] In some embodiments, treating the produce with a respiration reducing coating may reduce the rate at which the temperature rises in the stack (e.g., after removal from cold storage) by at least about 0.5° C. per day, such as at least 1.0° C., 1.5° C., 2.0° C., 2.5° C., 3.0° C., 3.5° C., 4.0° C., 4.5° C., or 5° C. per day, compared to an untreated stack. In some embodiments, treating the produce with a respiration reducing coating may reduce the equilibrium temperature difference between the atmosphere and the average temperature of the stack by at least about 0.5° C., 1.0° C., 1.5° C., 2.0° C., 2.5° C., 3.0° C., 3.5° C., 4.0° C., 4.5° C., or 5° C.

[0112]

[0123] Any of the coatings described herein may be used to protect any agricultural produce. In some embodiments, the coating may be coated on edible agricultural produce, such as fruits, vegetables, edible seeds and nuts, herbs, spices, produce, meat, eggs, dairy products, seafood, grains, or any other consumable item. In such embodiments, the coating may include ingredients that are non-toxic and safe for consumption by humans and / or animals. For example, the coating may include ingredients that are US Food and Drug Administration (FDA) approved direct or indirect food additives, FDA approved food contact substances, meet FDA regulatory requirements for use as food additives or food contact substances, and / or are generally recognized as safe (GRAS) materials by the FDA. Examples of such materials may be found in the FDA Code of Federal Regulations Title 21 at www.accessdata.fda.gov / scripts / cdrh / cfdocs / cfcfr / cfrsearch.cfm. In some embodiments, the coating components may include dietary supplements or dietary supplement ingredients. The coating components may also include FDA approved food additives or color additives. In some embodiments, the coating may include naturally occurring ingredients, as described herein. In some embodiments, the coating may be flavorless or have a high flavor threshold of less than 500 ppm, odorless or have a high odor threshold, and / or be substantially transparent. In some embodiments, the coating may be configured to be washed off of edible produce, for example, with water.

[0113]

[0124] In some embodiments, the coatings described herein may be formed on non-edible produce. Such non-edible produce may include, for example, non-edible flowers, seeds, shoots, stems, leaves, whole plants, and the like. In such embodiments, the coating may include ingredients that are non-toxic but whose threshold levels of non-toxicity may be higher than those prescribed for edible products. In such embodiments, the coating may include FDA approved food contact substances, FDA approved food additives, or FDA approved drug ingredients, such as any ingredient included in the FDA's database of approved drugs found at http: / / www.accessdata.fda.gov / scripts / cder / drugsatfda / index.cfm. In some embodiments, the coating may include materials that meet FDA requirements for use in drugs or are listed in the FDA's National Drug Discovery Code Directory, www.accessdata.fda.gov / scripts / cder / ndc / default.cfm. In certain embodiments, the material may include inactive drug ingredients of approved drugs listed in the FDA database, www.accessdata.fda.gov / scripts / cder / ndc / default.cfm.

[0114]

[0125] The embodiments of the coatings described herein provide several advantages, including, for example: (1) the coatings can protect produce from biotic stressors, i.e., bacteria, viruses, fungi, or pests; (2) the coatings can prevent water evaporation and / or diffusion of oxygen, carbon dioxide, and / or ethylene; (3) the coatings can help extend the shelf life of produce, e.g., post-harvest produce, without refrigeration; (4) the coatings can introduce mechanical stability to the surface of produce, while eliminating the need for expensive packaging designed to prevent bruising that accelerates spoilage; (5) the use of agricultural waste to obtain the coatings can help eliminate the breeding environment for bacteria, fungi, and pests; (6) the coatings can be used in place of pesticides to protect plants, thereby minimizing the harmful effects of pesticides on human health and the environment; and (7) the coatings can be naturally derived and therefore safe for human consumption. In some cases, such coatings can be made at a relatively low cost because the components of the coatings described herein are obtained from agricultural waste. Thus, the coatings may be particularly suitable for smallholder farmers, for example, by reducing the costs required to protect crops from pesticides and reduce post-harvest losses of agricultural produce due to spoilage due to biological and / or environmental stressors.

[0115] solvent

[0126] The solvent to which the coating agent and wetting agent (if separate from the coating agent) are added to form a solution / suspension / colloid can be, for example, water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, alcohol, any other suitable solvent, or combinations thereof. The resulting solution, suspension, or colloid can be suitable for forming a coating on the produce. For example, the solution, suspension, or colloid can be applied to the surface of the produce and then the solvent can be removed (e.g., by evaporation or convection drying) leaving a protective coating formed from the coating agent on the surface of the produce.

[0116]

[0127] While some of the solvents mentioned above (especially water and ethanol) can be safely and effectively used in solutions / suspensions / colloids applied to edible products such as produce or other agricultural products, it can often be advantageous to use either water or a solvent that is at least about 40% water by volume (often more). This is because water is typically less expensive than other suitable solvents and can also be safer to work with than solvents with higher volatility and / or lower flash points (e.g., acetone or alcohols, such as isopropanol or ethanol). In some embodiments, the solvent comprises water. For example, the solvent can be water. Thus, for any of the solutions / suspensions / colloids described herein, the solvent or solution / suspension / colloid can be at least about 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 99% water by weight or volume. In certain embodiments, the solvent or solution / suspension / colloid comprises a combination of water and ethanol, optionally being at least about 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 99% water by volume. In certain embodiments, the solvent is, by mass or volume, about 40% to about 100%, about 40% to about 99%, about 40% to about 95%, about 40% to about 90%, about 40% to about 85%, about 40% to about 80%, about 50% to about 100%, about 50% to about 99%, about 50% to about 95%, about 50% to about 90%, about 50% to about 85%, about 50% to about 80%, about 60% to about 100%, about 60% to about 99%, about 60% to about 95%, about 60% to about 90%, about 60% to about 85%, about 60% to about 8 The aqueous solution may be 0%, about 70% to about 100%, about 70% to about 99%, about 70% to about 95%, about 70% to about 90%, about 70% to about 85%, about 80% to about 100%, about 80% to about 99%, about 80% to about 97%, about 80% to about 95%, about 80% to about 93%, about 80% to about 90%, about 85% to about 100%, about 85% to about 99%, about 85% to about 97%, about 85% to about 95%, about 90% to about 100%, about 90% to about 99%, about 90% to about 98%, or about 90% to about 97% water.

[0117]

[0128] In view of the above, in some applications, the solvent may be a low wetting solvent (i.e., a solvent that exhibits a large contact angle with the surface to which it is applied). For example, in the absence of any added wetting agents or other surfactants, the contact angle between the solvent and any of (a) carnauba wax, (b) candelilla wax, (c) paraffin wax, or (d) no-wax lemon surfaces may be at least about 70°, e.g., at least about 75°, 80°, 85°, or 90°. The addition of any of the wetting agents described herein to a solvent, alone or in combination with other compounds or coating agents, can result in a contact angle between the resulting solution / suspension / colloid and any of (a) carnauba wax, (b) candelilla wax, (c) paraffin wax, or (d) no-wax lemon surfaces that is less than about 85°, such as less than about 80°, 75°, 70°, 65°, 60°, 55°, 50°, 45°, 40°, 35°, 30°, 25°, 20°, 15°, 10°, 5°, or 0°.

[0118]

[0129] The coating agent that is added to or dissolved, suspended, or dispersed in the solvent to form the coating solution / suspension / colloid can be any compound or combination of compounds capable of forming a protective coating on the substrate to which the solution / suspension / colloid is applied. The coating agent can be formulated such that the resulting coating protects the substrate from biotic and / or abiotic stressors. For example, the coating can prevent or inhibit the transfer of oxygen and / or water, thereby preventing the substrate from oxidizing and / or preventing water loss through transpiration / permeation / evaporation. If the substrate is perishable and / or edible, for example, if the substrate is a plant, agricultural product, or part of an agricultural crop, the coating agent is preferably composed of non-toxic compounds that are safe for consumption.

[0119] Coated agricultural products and methods of preparation and use thereof

[0130] In some embodiments, when the components of the coating agent (e.g., one or more glycerophospholipids) are mixed with a solvent, they form microstructures, such as, for example, vesicles in the solvent. In some embodiments, when this mixture contacts a surface, such as an agricultural product (e.g., a crop), the microstructures may adsorb to the surface and form an open bilayer (e.g., a thin layer), or a series of stacked open bilayers to form an open bilayer structure (e.g., a lamellar structure) on the surface. In some embodiments, after removal of the solvent or drying, the open bilayer structure splits into grains, and the boundaries between the grains are crystalline defects. In some embodiments, when this mixture contacts a surface, such as an agricultural product (e.g., a crop), the microstructures may adsorb to the surface and form a closed bilayer (e.g., a sphere or cylinder), or a series of closed bilayers to form a closed bilayer structure (e.g., a spherical or cylindrical structure) on the surface. In some embodiments, after removal of the solvent or drying, the closed bilayer structure splits into grains, and the boundaries between the grains are crystalline defects.

[0120]

[0131] In some embodiments, the advantage of the open bilayer (e.g., lamella) structure is its low permeability. Without being bound by theory, when water passes through the coating, it passes through the grain boundary and migrates between the open bilayer structure if the outer surface of the open bilayer structure is sufficiently hydrophilic (e.g., when the lamella is a lipid bilayer). In some embodiments, the open bilayer structure composed of lipid bilayers formed from one or more glycerophospholipids in the coating increases the hydrophilicity of the outer surface of the lipid bilayers that compose the coating, thus allowing more water to insert between the lipid bilayers, thus increasing the water permeability of the coating and resulting in an increased mass loss rate.

[0121]

[0132] In some embodiments, the advantage of a closed bilayer structure (e.g., a spherical or cylindrical structure) is its low permeability. Without being bound by theory, when water passes through the coating, it moves through the grain boundaries and between the closed bilayer structures if the outer surface of the closed bilayer structure is sufficiently hydrophilic (e.g., when the spherical or cylindrical structure is a lipid bilayer). In some embodiments, a closed bilayer structure composed of a lipid bilayer formed from one or more glycerophospholipids in the coating increases the hydrophilicity of the outer surface of the lipid bilayer that constitutes the coating, thus allowing more water to insert between the lipid bilayers, thus increasing the water permeability of the coating and resulting in an increased mass loss rate.

[0122]

[0133] In certain embodiments, by increasing the concentration of the coating agent in the mixture, the thickness of the coating is increased, which may, for example, decrease the water permeability (which may reduce mass loss when the coating is placed on produce) and decrease the gas diffusivity (which may reduce the respiration rate when the coating is placed on produce).

[0123]

[0134] In some embodiments, higher temperatures of drying can result in larger grain sizes in the coating and lower mosaicity (a measure of the probability that the orientation of the crystal planes in the coating deviates from a plane substantially parallel to that of the substrate surface, recognized as a type of crystal defect), which can result in fewer grain boundaries and imperfections for water and / or gas to pass through. In some embodiments, this can result in lower water and gas permeability, which can lead to lower mass loss rates and lower respiration rates, for example, when the coating is placed on produce.

[0124]

[0135] In some embodiments, heating the coating (or coated produce) from a first temperature to a second temperature higher than the first temperature but below the melting point (i.e., phase transition temperature) of the coating and then cooling the coating can increase the grain size in the coating, which can result in lower mass loss rates, lower gas diffusion rates, and lower respiration rates.

[0125] Coated produce

[0136] In one aspect, the present invention describes a coated substrate comprising a substrate and a coating comprising a glycerophospholipid layer having an open or closed glycerophospholipid bilayer structure formed on the substrate, wherein the coating has a thickness of less than about 20 microns.For example, the coating can have a thickness of less than about 10 microns, 5 microns, 2 microns, or 1 micron.

[0126]

[0137] In certain embodiments, the glycerophospholipid layer comprises one or more open bilayers. For example, the open bilayer can be lamellar.

[0127]

[0138] In certain embodiments, the glycerophospholipid layer comprises one or more closed bilayers, For example, each of the one or more closed bilayers can be independently cylindrical or spherical.

[0128]

[0139] In another aspect, described herein is a coated substrate comprising a substrate and a coating comprising a layered structure formed on the substrate, the coating comprising a plurality of grains. In another aspect, described herein is a coated substrate comprising a substrate and a coating comprising a spherical structure formed on the substrate, the coating comprising a plurality of grains. In another aspect, described herein is a coated substrate comprising a substrate and a coating comprising a cylindrical structure formed on the substrate, the coating comprising a plurality of grains.

[0129]

[0140] In certain embodiments, the substrate is an agricultural product, a silicon substrate, a polystyrene substrate, or a substrate comprising a polysaccharide (e.g., cellulose). For example, the substrate can be an agricultural product.

[0130]

[0141] In another aspect, described herein is a coated agricultural product comprising a produce and a coating comprising layered structures formed on the produce, wherein the coating has a thickness of less than about 20 microns. In another aspect, described herein is a coated agricultural product comprising a produce and a coating comprising spherical structures formed on the produce, wherein the coating has a thickness of less than about 20 microns. In another aspect, described herein is a coated agricultural product comprising a produce and a coating comprising cylindrical structures formed on the produce, wherein the coating has a thickness of less than about 20 microns.

[0131]

[0142] In another aspect, described herein is a coated agricultural product comprising an agricultural product and a coating comprising a layered structure formed on the agricultural product, the coating comprising a plurality of grains. In another aspect, described herein is a coated agricultural product comprising an agricultural product and a coating comprising a cylindrical structure formed on the agricultural product, the coating comprising a plurality of grains. In another aspect, described herein is a coated agricultural product comprising an agricultural product and a coating comprising a spherical structure formed on the agricultural product, the coating comprising a plurality of grains.

[0132]

[0143] In certain embodiments (e.g., when the lamina is a lipid bilayer, such as a lipid bilayer comprising one or more glycerophospholipids), the lattice formation is defined by a hexagonal unit cell. The distance between each adjacent molecule in the unit cell (referred to as "a") is about 0.2 nm to about 2 nm, e.g., about 0.2 to about 0.7 nm, about 0.2 to about 1.2 nm, about 0.2 nm to about 0.4 nm, about 0.3 nm to about 0.5 nm, about 0.4 nm to about 0.6 nm, about 0.43 nm to about 0.5 nm, or about 0.47 nm to about 0.48 nm. In certain embodiments, the lattice formation is defined by an orthorhombic unit cell. In certain embodiments, the lattice formation is defined by a tetragonal unit cell. In certain embodiments, the lattice formation is defined by a monoclinic unit cell.

[0133]

[0144] In some embodiments, the layered structure includes a plurality of thin layers. The distance between the surface of a thin layer and the surface of an adjacent thin layer facing the same direction is referred to herein as the "periodic interval". In some embodiments, the interlayer interval of the thin layers is about 1.0 to about 20 nm. For example, it is about 1 to about 20 nm, about 2 to about 13 nm, about 3 to about 10 nm, about 3 to about 7 nm, about 3 to about 6 nm, about 3 to about 5 nm, about 5 to about 7 nm, about 4 to about 6 nm, about 4 to about 5 nm, about 5 to about 6 nm, or about 5.0 to about 5.8 nm.

[0134]

[0145] In some embodiments, the coating comprises a plurality of grains.

[0135]

[0146] In one embodiment, the grain size is about 2 nm to about 100 nm, for example, about 4 nm to about 100 nm, about 7 nm to about 100 nm, about 6 nm to about 100 nm, about 6 nm to about 80 nm, about 6 nm to about 60 nm, about 6 nm to about 40 nm, about 6 nm to about 25 nm, about 9 nm to about 22 nm, about 9 nm to about 15 nm, about 13 nm to about 25 nm, about 8 nm to about 25 nm, about 11 nm to about 17 nm, about 11 nm to about 14 nm, about 13 nm to about 17 nm, and the like. m, about 12nm to about 16nm, about 15nm to about 17nm, about 9nm to about 13nm, about 13nm to about 17nm, about 17nm to about 25nm, about 2nm to about 10nm, 5nm to about 10nm, about 8nm to about 9nm, about 8.5nm about 9.5 nm, about 9 nm to about 10 nm, about 8 nm, about 9 nm, about 10 nm, about 11 nm, about 12 nm, about 13 nm, about 14 nm, about 15 nm, about 16 nm, about 17 nm, about 19 nm, about 21 nm, or about 22 nm.

[0136] Method of Use and Application

[0147] In one embodiment, there is provided a method of coating a substrate, comprising the steps of: applying a solution comprising one or more glycerophospholipids to a surface of the produce; and drying the solution on the surface of the produce under a forced air stream to form a glycerophospholipid layer on the produce; where: the glycerophospholipid layer comprises a plurality of glycerophospholipid bilayers; Described herein are methods wherein the glycerophospholipid layer has a thickness of less than about 2 microns.

[0137]

[0148] In another aspect, there is provided a method of coating a substrate, comprising the steps of: applying a solution comprising one or more glycerophospholipids to a surface of the produce; and drying the solution on the surface of the produce under a forced air flow at a temperature above about 50° C. to form a glycerophospholipid layer on the produce; where: the glycerophospholipid layer comprises a plurality of glycerophospholipid bilayers; Described herein are methods in which each of the glycerophospholipid bilayers comprises a plurality of grains.

[0138]

[0149] In one embodiment, the temperature of the solution is about 10°C to about 80°C, for example, about 10°C to about 70°C, about 20°C to about 80°C, about 20°C to about 60°C, or about 40°C to about 70°C.

[0139]

[0150] In one embodiment, the temperature of the air is from about 20°C to about 120°C, for example, from about 20°C to about 100°C, from about 40°C to about 120°C, or from about 50°C to about 100°C.

[0140]

[0151] In another aspect, there is provided a method of coating a substrate, comprising the steps of: applying a mixture comprising a coating agent and a solvent to a substrate; removing the solvent to form a coating on the substrate; heating the coated produce from a first temperature to a second temperature, the second temperature being greater than the first temperature and less than the melting point of the coating; and cooling the coated substrate from the second temperature to a third temperature, the third temperature being less than the second temperature; where: the coating comprises a plurality of glycerophospholipid bilayers; Described herein are methods in which each of the glycerophospholipid bilayers comprises a plurality of grains.

[0141]

[0152] In one embodiment, the first temperature is about 0° C. to about 50° C., for example, about 10° C. to about 40° C., about 20° C. to about 30° C., about 23° C. to about 27° C., or about 25° C. In one embodiment, the first temperature is higher than the temperature of the surrounding outside air. In one embodiment, the first temperature is lower than the temperature of the surrounding outside air.

[0142]

[0153] In some embodiments, the second temperature is from about 40°C to about 65°C, e.g., from about 45°C to about 65°C, from about 50°C to about 65°C, from about 55°C to about 65°C, from about 57°C to about 63°C, or about 60°C. In some embodiments, the second temperature is higher than the temperature of the surrounding air. In some embodiments, the second temperature is lower than the temperature of the surrounding air. In some embodiments, the coated produce is heated with air having a temperature higher than the temperature of the produce. In some embodiments, the air in which the coated produce is heated is higher than the second temperature. In some embodiments, the air in which the coated produce is heated is higher than the melting point of the coating.

[0143]

[0154] In certain embodiments, when a coating is heated at or above its melting temperature (e.g., about 65° C. to about 70° C., or about 70° C.), the lattice formation of the crystal planes (e.g., lamellae) in the coating may be disrupted, the constituent molecules may adopt random orientations, and the coating may liquefy.

[0144]

[0155] In one embodiment, the third temperature is about 0° C. to about 50° C., for example, about 10° C. to about 40° C., about 20° C. to about 30° C., about 23° C. to about 27° C., or about 25° C. In one embodiment, the third temperature is higher than the temperature of the surrounding outside air. In one embodiment, the third temperature is lower than the temperature of the surrounding outside air.

[0145]

[0156] In certain embodiments, the second temperature is maintained for about 5 seconds to about 10 hours. For example, the second temperature can be maintained for about 5 seconds to about 7 hours, about 5 seconds to about 3 hours, about 5 seconds to about 1.5 hours, about 5 seconds to about 60 minutes, about 30 seconds to about 45 minutes, about 5 minutes to about 60 minutes, about 10 minutes to about 45 minutes, about 20 minutes to about 40 minutes, about 25 minutes to about 35 minutes, about 30 seconds to about 10 minutes, about 30 seconds to about 7 minutes, about 30 seconds to about 3 minutes, about 3 minutes to about 7 minutes, about 30 seconds to about 1 minute, or about 1 minute to about 5 minutes.

[0146]

[0157] In some embodiments, the grain size of the coated agricultural product after cooling from the second temperature to the third temperature is larger than the grain size of the coated agricultural product before heating from the first temperature to the second temperature. In some embodiments, the grain size of the coating before heating from the first temperature to the second temperature is about 2 nm to about 10 nm. For example, it is about 5 nm to about 10 nm, about 8 nm to about 9 nm, about 8.5 nm to about 9.5 nm, or about 9 nm to about 10 nm. For example, the grain size of the coating after cooling from the second temperature to the third temperature can be about 7 nm to about 100 nm (e.g., about 8 nm to about 25 nm, about 11 nm to about 17 nm, about 11 nm to about 14 nm, about 13 nm to about 17 nm, about 12 nm to about 16 nm, or about 15 nm to about 17 nm).

[0147]

[0158] In another aspect, there is provided a method for reducing mass loss rate in produce, comprising the steps of: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0148]

[0159] In another aspect, there is provided a method for reducing the respiration rate of produce, comprising: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0149]

[0160] In some embodiments, the mixture is dried at a temperature of about 20° C. to about 100° C., e.g., about 25° C. to about 80° C., about 25° C. to about 70° C., about 30° C. to about 65° C., about 40° C. to about 65° C., 50° C. to about 65° C., about 55° C. to about 65° C., about 60° C. to about 65° C., about 55° C., about 60° C., or about 65° C. In some embodiments, the mixture is partially dried. In some embodiments, the drying removes more than about 5% of the solvent, e.g., more than about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% of the solvent. In some embodiments, a bilayer structure is formed when the mixture is partially dried. In certain embodiments, the bilayer structure is formed after at least 5% of the solvent has been removed, e.g., after at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% of the solvent has been removed.

[0150]

[0161] In some embodiments, faster solvent removal and / or drying can improve the performance of the coating. For example, faster solvent removal and / or drying can result in thicker and more uniform coatings. In some embodiments, solvent removal or mixture drying is performed in less than about 2 hours, for example, less than about 1.5 hours, 1 hour, 45 minutes, 30 minutes, 25 minutes, 20 minutes, 15 minutes, 10 minutes, 5 minutes, 4 minutes, 2 minutes, 1 minute, 30 seconds, 15 seconds, 10 seconds, 5 seconds, or 3 seconds.

[0151]

[0162] In another aspect, there is provided a method of coating produce, comprising the steps of: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0152]

[0163] In another aspect, there is provided a method of preparing a produce having a coating disposed thereon, comprising the steps of: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0153]

[0164] In another aspect, there is provided a method of reducing the water permeability of a coating on a substrate, comprising the steps of: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0154]

[0165] In another aspect, there is provided a method for reducing a gas diffusivity of a coating on a substrate, comprising the steps of: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0155]

[0166] In certain embodiments, the substrate is an agricultural product, a silicon substrate, a polystyrene substrate, or a substrate comprising a polysaccharide (e.g., cellulose). For example, the substrate can be an agricultural product.

[0156]

[0167] In another aspect, a method for reducing a mass loss rate of produce having a coating disposed thereon, comprising: applying a solution comprising one or more glycerophospholipids and a solvent to a surface of the produce; and Methods are described herein that include drying the solution on the surface of the produce under a forced air flow to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

[0157] Coating thickness and mass loss factor / rate

[0168] In certain embodiments, for coatings formulated to prevent moisture loss from or oxidation of a coated substrate, such as an agricultural crop, a thicker coating will be less permeable to water and oxygen than a thinner coating formed from the same coating agent, and therefore should result in a lower rate of mass loss compared to the thinner coating. Thicker coatings can be formed by increasing the concentration of the coating agent in the solution / suspension / colloid and applying a similar volume of the solution / suspension / colloid to each piece of the crop (of similar size). EXAMPLES

[0158]

[0169] The following examples describe the effect of various coating agents and solutions / suspensions / colloids on various substrates, as well as some characterizations of various coating agents and solutions / suspensions / colloids. These examples are for illustrative purposes only and are not intended to limit the scope of the present disclosure. In each of the following examples, unless otherwise specified, all reagents and solvents were purchased and used without further purification.

[0159] Example 1: Effect of a coating made with glycerophospholipids on the mass loss rate and respiration rate of produce.

[0170] FIG. 1 is a graph showing the mass loss coefficient of Hass avocados treated with various coating agents suspended in water. "Untreated" corresponds to untreated produce. "MAG / FAS(95 / 5)" corresponds to a coating agent formed from 95% monoglycerides (of which about 90% is glycerol monostearate) and 5% sodium stearate at a concentration of 30 g / L. "Soy Lecithin" corresponds to a coating agent formed from glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol, where the coating agent is lecithin derived from soybeans. The total concentration of glycerophospholipids was 100 g / L.

[0160]

[0171] All coatings were formed by bowl dipping the produce in their respective solutions and drying the produce under forced air flow at a temperature of 70° C. As can be seen in FIG. 1, the mass loss factor for the produce corresponding to the glycerophospholipid coating was 1.58, the mass loss factor for the produce corresponding to the MAG / FAS (95 / 5) coating was 1.44, and the mass loss factor for the untreated produce was 1.00.

[0161]

[0172] As can be seen in FIG. 2, the respiration rate for the untreated produce was higher than the respiration rate for the produce coated with the monoglyceride coating, and both of these were higher than the respiration rates for the glycerophospholipid coating.

[0162] Example 2: Structure of the glycerophospholipid coating as determined by X-ray scattering.

[0173] The coatings were applied to the surface of a silicon substrate, which acts as a hydrophilic surface when exposed to air. X-ray scattering images of the applied coatings were acquired to characterize the coatings.

[0163]

[0174] A coating containing phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol (glycerophospholipid at 100 g / L) was applied to the surface of a polystyrene substrate, and X-ray scattering images of the applied coat were obtained and analyzed to determine the properties of the coating based on the scattering patterns.

[0164]

[0175] As shown in FIG. 3, as determined by the scattering pattern, the coating has a hexagonal cylindrical phase (HCP) structure that includes repeating cylindrical units arranged in a hexagonal close-packed lattice at the surface of the substrate.

[0165] Example 3: The effect of coatings formed from glycerophospholipids on mass loss rate and respiration rate of produce applied at different concentrations.

[0118] Figure 4 is a graph showing the mass loss coefficient of produce treated with various coatings suspended in water. "Untreated" corresponds to untreated produce. "MAG / FAS (30 g / L)" corresponds to a coating formed from monoglycerides at a concentration of 30 g / L. "Lecithin" corresponds to a coating formed from glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol. The total concentration of glycerophospholipids varies from 30 to 150 g / L, where coatings applied at higher concentrations result in an increase in MLF.

[0166] As can be seen in Figure 5 and Table 2, the respiration rates for untreated produce were higher than the respiration rates for produce coated with the monoglyceride coating, both of which were higher than the respiration rates for the glycerophospholipid coating. Additionally, the respiration rates of the coatings applied at higher concentrations were lower than the coatings applied at lower concentrations.

[0167] [Table 2]

[0168] Example 4: Structure of glycerophospholipid coatings applied at different concentrations as determined by X-ray scattering.

[0120] The coatings were applied to the surface of a polystyrene substrate, which acts as a hydrophobic surface when exposed to air. X-ray scattering images of the applied coatings were obtained to characterize the coatings.

[0169]

[0121] As shown in Figure 6, coatings applied at concentrations ranging from 30 to 150 g / L exhibit a periodic spacing of 4.9 nm as determined by scattering patterns. The primary peak used in this calculation is labeled with an arrow (black).

[0170]

[0122] As shown in Figure 7, coatings applied at concentrations ranging from 30 to 150 g / L exhibit hexagonally packed cylinder structures (HCPs) regardless of concentration, which contain repeating cylindrical units arranged in a hexagonally close-packed lattice at the surface of the substrate, as determined by scattering patterns. The peaks used to identify the characteristic HCP ratios are labeled with arrows.

[0171] As shown in Figure 8, as determined by scattering patterns, coatings applied at concentrations ranging from 30 to 150 g / L exhibit hexagonally packed cylinder (HCP) structures aligned perpendicular to the substrate surface as indicated by significant out-of-plane (⊥) scattering. Negligible scattering is observed in the in-plane (||) direction, further suggesting alignment of the cylinders.

[0172] Example 5: Effect of coatings formed from hydrogenated and non-hydrogenated glycerophospholipids on mass loss rate and respiration rate of produce.

[0124] All coatings were formed by bowl dipping the produce in their relevant solutions and drying the produce under forced air flow at a temperature of 70° C. As seen in Figure 9, the mass loss factor for the produce corresponding to the soy-derived glycerophospholipid coating was 1.27, the mass loss factor for the produce corresponding to the non-hydrogenated phosphatidylcholine (PC) was 1.44, the mass loss factor for the produce corresponding to the hydrogenated phosphatidylcholine (PC) was 1.33, the mass loss factor for the produce corresponding to the MAG / FAS coating was 1.41, and the mass loss factor for the untreated produce was 1.00.

[0173] Example 6: Structure of hydrogenated and non-hydrogenated glycerophospholipid coatings as determined by X-ray scattering.

[0125] The coatings were applied to the surface of a polystyrene substrate, which acts as a hydrophobic surface when exposed to air. X-ray scattering images of the applied coatings were obtained to characterize the coatings.

[0174]

[0126] As shown in Figure 10, the coatings containing non-hydrogenated phosphatidylcholine and hydrogenated phosphatidylcholine show periodic intervals of 3.8-4.5 nm and 6.2 nm, respectively. As shown in Figure 11, the coatings show a layered structure composed of alternating bilayers at the surface of the substrate as determined by the scattering pattern. As shown in Figure 12, the coatings show a mixed morphology of lamellae and hexagonally packed cylinders at the surface of the substrate as determined by the scattering pattern. The peaks used for analysis are labeled with arrows.

[0175] Example 7: Structure of the coating as determined by X-ray scattering.

[0176] A solution of 100 g / L lysolecithin was prepared by mixing the ingredients in a mixer in deionized water at 85° C. until uniform. The solution was cooled to room temperature (20° C.) and 0.1 mL was drop cast onto a substrate and allowed to dry at ambient conditions. Figure 13 shows the q (Å) distribution from X-ray scattering images of the lysolecithin coating and the 50 g / L MAG / FAS coating. -1 ) plot of intensity against

[0176]

[0177] While various compositions and methods have been described above, it should be understood that they are presented by way of example only and not by way of limitation. Where the methods and steps described above show certain events occurring in a particular order, the order of the steps may be altered, and such alterations are in accordance with variations of the invention. Furthermore, some of the steps may not only be performed sequentially as described above, but may also be performed simultaneously in a parallel process, if possible. Although various implementations have been specifically shown and described, it will be understood that various changes in form and details may be made. Accordingly, other implementations are within the scope of the following claims.

[0177]

[0178] Although the present disclosure includes details of many specific embodiments, these should not be construed as limitations on the scope of the subject matter or what may be claimed, but rather as descriptions of features that may be specific to particular embodiments. Certain features described in the present disclosure in the context of separate embodiments may also be implemented in combination in a single embodiment. Conversely, various features described in the context of a single embodiment may also be implemented in multiple embodiments separately or in any suitable subcombination. Furthermore, although the features described above may be described as functioning in a combination, and even initially claimed as such, one or more features from the claimed combination may, in some cases, be deleted from the combination, and the claimed combination may be directed to a subcombination or a variation of the subcombination.

[0178]

[0179] Specific embodiments of the subject matter have been described. As will be apparent to those skilled in the art, other embodiments, modifications, and permutations of the described embodiments are within the scope of the following claims. Although operations are depicted in the drawings or claims in a particular order, this should not be understood as requiring such operations to be performed in the particular order or sequential order depicted, or that all of the depicted operations be performed, to achieve desirable results (some operations may be considered optional).

[0179]

[0180] Therefore, the example embodiments described above do not define or limit this disclosure. Other modifications, substitutions, and alterations are also possible without departing from the spirit and scope of this disclosure.

Claims

1. 1. A method for reducing the rate of ripening of agricultural produce, comprising: applying a solution comprising one or more glycerophospholipids to the surface of the produce, wherein the solution has a temperature of from 10°C to 80°C; and drying the solution on the surface of the produce under a stream of air having a temperature of between 20°C and 100°C to promote self-assembly of a plurality of glycerophospholipid bilayers on the surface of the produce, thereby forming a glycerophospholipid layer on the produce.

2. 2. The method of claim 1, wherein the one or more glycerophospholipids comprise one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

3. The one or more glycerophospholipids are one or more compounds of formula I: 【Chemistry 50】 comprising the formula: R １ is -H or one of the following fragments: 【Chemistry 51】 R ２ and R ３ is each independently at each occurrence -H or Formula II: 【Chemistry 52】 wherein: R ４ , R ５ , R ８ , R ９ , R １２ , R １３ , R １４ , R １５ and R １６ are respectively Each occurrence is replaced with -H, -OH, or -OR. １７ or C １ ~C ６ is alkyl; R ６ , R ７ , R １０ , and R １１ Each occurrence of is independently -H, -O R １７ , or C １ ~C ６ is alkyl; and / or R ４ and R ５ may combine with the carbon atom to which they are attached to form C═O; and / or R ８ and R ９ may combine with the carbon atom to which they are attached to form C═O; and / or R １２ and R １３ combine with the carbon atom to which they are attached to form C=O Gain; R １７ But each time it appears, C １ ~C ６ is alkyl, The above symbol 【Chemistry 53】 represents a single bond or a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7, or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; 2. The method of claim 1, wherein r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

4. The fragment represented by formula II is 【Chemical Formula 54】 【Chemistry 55】 【Chemical 56】 【Chemical 57】 The method of claim 3, wherein the method is one of:

5. 5. The method of claim 1, wherein the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.

6. 6. The method of claim 5, wherein the one or more glycerophospholipids comprise 20% to 40% by weight phosphatidylcholine, 20% to 40% by weight phosphatidylethanolamine, and 20% to 40% by weight phosphatidylinositol.

7. The method of claim 5 , wherein the one or more glycerophospholipids further comprise phosphatidylserine.

8. 8. The method of claim 7, wherein the one or more glycerophospholipids contain less than 5% by weight of phosphatidylserine.

9. The method of any one of claims 1 to 4, wherein the solution further comprises a plant sterol.

10. 10. The method of claim 9, wherein the weight ratio of the plant sterol to the total amount of the one or more glycerophospholipids is less than 0.

05.

11. 5. The method of claim 1, wherein the total concentration of the one or more glycerophospholipids in the solution is from 50 g / L to 150 g / L.

12. The method according to any one of claims 1 to 4, wherein the solution is an aqueous solution.

13. The method of any one of claims 1 to 4, wherein the solution does not contain an added surfactant.

14. The method according to any one of claims 1 to 4, wherein the temperature of the air is between 50°C and 100°C.

15. The method of any one of claims 1 to 4, wherein the glycerophospholipid layer comprises one or more open bilayers.

16. The method of any one of claims 1 to 4, wherein the glycerophospholipid layer comprises one or more closed bilayers.

17. The method of any one of claims 1 to 4, wherein the layer has a thickness of less than 2 microns.

18. agricultural products and; a coating on the surface of the produce; and 1. A coated agricultural product comprising: one or more glycerophospholipids, and a plurality of glycerophospholipid bilayers on the surface of said produce Coated produce, including

19. 20. The coated produce of claim 18, wherein the one or more glycerophospholipids comprise one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

20. The one or more glycerophospholipids are one or more compounds of formula I: 【Chemistry 58】 comprising the formula: R １ is -H or one of the following fragments: 【Chemical Formula 59】 R ２ and R ３ is each independently at each occurrence -H or Formula II: 【Chemistry 60】 wherein: R ４ , R ５ , R ８ , R ９ , R １２ , R １３ , R １４ , R １５ and R １６ each occurrence independently represents -H, -OH, -OR １７ Or C １ ~C ６ is alkyl; R ６ , R ７ , R １０ , and R １１ each independently at each occurrence is -H, -OR １７ , or C １ ~C ６ is alkyl; and / or R ４ and R ５ may combine with the carbon atom to which they are attached to form C═O; and / or R ８ and R ９ may combine with the carbon atom to which they are attached to form C═O; and / or R １２ and R １３ may combine with the carbon atom to which they are attached to form C═O; R １７ But each time it appears, C １ ~C ６ is alkyl, The above symbol 【Hua 61】 represents a single bond or a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7, or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; 20. The coated produce of claim 18, wherein r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

21. The fragment represented by formula II is 【Hua 62】 【Chemistry 63】 【Hua 64】 【Chemistry 65】 21. The coated produce of claim 20, wherein the coated produce is one of:

22. 22. The coated produce of any one of claims 18 to 21, wherein the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.

23. 23. The coated produce of claim 22, wherein the one or more glycerophospholipids comprise 20% to 40% by weight phosphatidylcholine, 20% to 40% by weight phosphatidylethanolamine, and 20% to 40% by weight phosphatidylinositol.

24. 23. The coated produce of claim 22, wherein the one or more glycerophospholipids further comprise phosphatidylserine.

25. 25. The coated produce of claim 24, wherein the one or more glycerophospholipids contain less than 5% by weight of phosphatidylserine.

26. 22. The coated produce of any one of claims 18 to 21, wherein the plurality of glycerophospholipid bilayers comprises one or more open bilayers.

27. 22. The coated produce of any one of claims 18 to 21, wherein the plurality of glycerophospholipid bilayers comprises one or more closed bilayers.

28. 22. The coated produce of any one of claims 18 to 21, wherein the coating has a thickness of less than 2 microns.

Images